Bendamustine hydrochloride supplier

Name
Bendamustine hydrochloride
EINECS 631-540-0
CAS No. 3543-75-7
Article Data18
CAS DataBase
Density
Solubility
Melting Point 149-151 °C
Formula C₁₆H₂₂Cl₃N₃O₂
Boiling Point 585.2 °C at 760 mmHg
Molecular Weight 394.729
Flash Point 307.7 °C
Transport Information
Appearance pale brown crystals
Safety 36-37
Risk Codes 60-61-22-40
Molecular Structure
Hazard Symbols T,Xn
Synonyms 1H-Benzimidazole-2-butanoicacid, 5-[bis(2-chloroethyl)amino]-1-methyl-, monohydrochloride (9CI);2-Benzimidazolebutyric acid, 5-[bis(2-chloroethyl)amino]-1-methyl-,monohydrochloride (8CI);1H-Benzimidazole-2-butanoicacid, 5-[bis(2-chloroethyl)amino]-1-methyl-, hydrochloride (1:1);Cytostasan;IMET 3393;Ribomustin;SDX 105;ZIMET 33/93;Bendamustine HCl;
PSA 58.36000
LogP 4.06660

Synthetic route

: 4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid ethyl ester

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water for 4h; Reflux;	83%
With hydrogenchloride; water at 40℃; for 2h; Product distribution / selectivity;
With hydrogenchloride In water at 25 - 28℃; for 0.25h;

: 3543-74-6
4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Stage #1: 4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester With thionyl chloride In dichloromethane at -1 - 22℃; for 17h; Stage #2: With hydrogenchloride In water at 75℃;	76.2%
Stage #1: 4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester With thionyl chloride In chloroform at 0 - 5℃; Stage #2: With hydrogenchloride; pyrographite In water at 30℃; Reflux;	75%
Stage #1: 4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester With thionyl chloride In chloroform at 0 - 25℃; Large scale; Stage #2: With hydrogenchloride In chloroform; water Large scale;	75%

: 109882-25-9
4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid methyl ester

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride for 4h; Reflux; Large scale reaction;	76%
With hydrogenchloride; water for 4h; Reflux;
With hydrogenchloride In water at 25 - 28℃; for 0.25h;

: 1313020-25-5
bendamustine isopropyl ester

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; water at 35 - 40℃; for 1.5h; Product distribution / selectivity;	75%

: 1313020-26-6
isopropyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / water / 2 h / 70 - 75 °C 1.2: 1.5 h / 70 - 75 °C 2.1: thionyl chloride / dichloromethane / 7 h / 0 - 30 °C 3.1: hydrogenchloride; water / 1.5 h / 35 - 40 °C View Scheme
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / water / 25 - 95 °C 2.1: thionyl chloride / dichloromethane / 2 h / 25 - 60 °C 2.2: 25 - 30 °C View Scheme

: 1221157-09-0
4-(2,4-dinitrophenylcarbamoyl)butyric acid methyl ester

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / acetonitrile / 23 - 25 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 3: sodium tetrahydroborate / 1,2-dichloro-ethane / 30 - 50 °C / Large scale reaction 4: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 23 - 25 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 2.2: 2 h / 60 - 65 °C 3.1: sodium tetrahydroborate / 1,2-dichloro-ethane / 30 - 50 °C / Large scale reaction 4.1: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 23 - 25 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 2.2: 2 h / 60 - 65 °C 3.1: borane-THF / tetrahydrofuran / 30 - 50 °C / Large scale reaction 4.1: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme
Multi-step reaction with 4 steps 1: potassium carbonate / acetonitrile / 23 - 25 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 3: borane-THF / tetrahydrofuran / 30 - 50 °C / Large scale reaction 4: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme

: 1221157-10-3
4-[(2,4-dinitrophenyl)methylcarbamoyl]butyric acid methyl ester

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 2: sodium tetrahydroborate / 1,2-dichloro-ethane / 30 - 50 °C / Large scale reaction 3: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme
Multi-step reaction with 3 steps 1.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 1.2: 2 h / 60 - 65 °C 2.1: sodium tetrahydroborate / 1,2-dichloro-ethane / 30 - 50 °C / Large scale reaction 3.1: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme
Multi-step reaction with 3 steps 1.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 1.2: 2 h / 60 - 65 °C 2.1: borane-THF / tetrahydrofuran / 30 - 50 °C / Large scale reaction 3.1: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 2: borane-THF / tetrahydrofuran / 30 - 50 °C / Large scale reaction 3: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme

: 1221157-11-4
4-(5-amino-1-methyl-1H-benzoimidazol-2-yl)butyric acid methyl ester hydrochloride

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / 1,2-dichloro-ethane / 30 - 50 °C / Large scale reaction 2: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme
Multi-step reaction with 2 steps 1: borane-THF / tetrahydrofuran / 30 - 50 °C / Large scale reaction 2: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme

: 1501-26-4
methyl 4-(chlorocarbonyl)butyrate

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: toluene / 6 h / 95 - 105 °C / Large scale reaction 2: potassium carbonate / acetonitrile / 23 - 25 °C 3: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 4: sodium tetrahydroborate / 1,2-dichloro-ethane / 30 - 50 °C / Large scale reaction 5: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme
Multi-step reaction with 5 steps 1.1: toluene / 6 h / 95 - 105 °C / Large scale reaction 2.1: potassium carbonate / acetonitrile / 23 - 25 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 3.2: 2 h / 60 - 65 °C 4.1: sodium tetrahydroborate / 1,2-dichloro-ethane / 30 - 50 °C / Large scale reaction 5.1: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme
Multi-step reaction with 5 steps 1.1: toluene / 6 h / 95 - 105 °C / Large scale reaction 2.1: potassium carbonate / acetonitrile / 23 - 25 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 3.2: 2 h / 60 - 65 °C 4.1: borane-THF / tetrahydrofuran / 30 - 50 °C / Large scale reaction 5.1: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme
Multi-step reaction with 5 steps 1: toluene / 6 h / 95 - 105 °C / Large scale reaction 2: potassium carbonate / acetonitrile / 23 - 25 °C 3: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 4: borane-THF / tetrahydrofuran / 30 - 50 °C / Large scale reaction 5: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme

: 97-02-9
2,4-Dinitroanilin

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: toluene / 6 h / 95 - 105 °C / Large scale reaction 2: potassium carbonate / acetonitrile / 23 - 25 °C 3: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 4: sodium tetrahydroborate / 1,2-dichloro-ethane / 30 - 50 °C / Large scale reaction 5: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme
Multi-step reaction with 5 steps 1.1: toluene / 6 h / 95 - 105 °C / Large scale reaction 2.1: potassium carbonate / acetonitrile / 23 - 25 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 3.2: 2 h / 60 - 65 °C 4.1: sodium tetrahydroborate / 1,2-dichloro-ethane / 30 - 50 °C / Large scale reaction 5.1: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme
Multi-step reaction with 5 steps 1.1: toluene / 6 h / 95 - 105 °C / Large scale reaction 2.1: potassium carbonate / acetonitrile / 23 - 25 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 3.2: 2 h / 60 - 65 °C 4.1: borane-THF / tetrahydrofuran / 30 - 50 °C / Large scale reaction 5.1: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme
Multi-step reaction with 5 steps 1: toluene / 6 h / 95 - 105 °C / Large scale reaction 2: potassium carbonate / acetonitrile / 23 - 25 °C 3: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2068.65 Torr / Large scale reaction 4: borane-THF / tetrahydrofuran / 30 - 50 °C / Large scale reaction 5: hydrogenchloride / 4 h / Reflux; Large scale reaction View Scheme

: 2044-88-4
N-methyl-2,4-dinitroaniline

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium sulfide; sodium hydrogencarbonate / water; methanol / 25 - 80 °C 2.1: 35 - 40 °C 2.2: 80 - 85 °C 2.3: 25 - 30 °C 3.1: hydrogen / Raney nickel / methanol / 25 - 30 °C / 4654.46 - 5171.62 Torr 4.1: N-ethyl-N,N-diisopropylamine / water / 25 - 95 °C 5.1: thionyl chloride / dichloromethane / 25 - 60 °C 5.2: 55 - 60 °C View Scheme
Multi-step reaction with 5 steps 1.1: sodium sulfide; sodium hydrogencarbonate / methanol; water / 25 - 80 °C 2.1: 35 - 40 °C 2.2: 35 - 85 °C / Reflux 3.1: hydrogen / methanol / 4654.46 - 5171.62 Torr / Autoclave 4.1: N-ethyl-N,N-diisopropylamine / water / 25 - 95 °C 5.1: thionyl chloride / dichloromethane / 2 h / 25 - 60 °C 5.2: 25 - 30 °C View Scheme

: 97-00-7
1-chloro-2,4-dinitro-benzene

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: water; methanol / 0 - 30 °C 2.1: sodium sulfide; sodium hydrogencarbonate / water; methanol / 25 - 80 °C 3.1: 35 - 40 °C 3.2: 80 - 85 °C 3.3: 25 - 30 °C 4.1: hydrogen / Raney nickel / methanol / 25 - 30 °C / 4654.46 - 5171.62 Torr 5.1: N-ethyl-N,N-diisopropylamine / water / 25 - 95 °C 6.1: thionyl chloride / dichloromethane / 25 - 60 °C 6.2: 55 - 60 °C View Scheme
Multi-step reaction with 6 steps 1.1: methanol; water 2.1: sodium sulfide; sodium hydrogencarbonate / methanol; water / 25 - 80 °C 3.1: 35 - 40 °C 3.2: 35 - 85 °C / Reflux 4.1: hydrogen / methanol / 4654.46 - 5171.62 Torr / Autoclave 5.1: N-ethyl-N,N-diisopropylamine / water / 25 - 95 °C 6.1: thionyl chloride / dichloromethane / 2 h / 25 - 60 °C 6.2: 25 - 30 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: water; methanol / 0 - 30 °C
2.1: sodium sulfide; sodium hydrogencarbonate / water; methanol / 25 - 80 °C
3.1: 35 - 40 °C
3.2: 80 - 85 °C
3.3: 25 - 30 °C
4.1: hydrogen / Raney nickel / methanol / 25 - 30 °C / 4654.46 - 5171.62 Torr
5.1: N-ethyl-N,N-diisopropylamine / water / 25 - 95 °C
6.1: thionyl chloride / dichloromethane / 25 - 60 °C
6.2: 55 - 60 °C
View Scheme

Multi-step reaction with 6 steps
1.1: methanol; water
2.1: sodium sulfide; sodium hydrogencarbonate / methanol; water / 25 - 80 °C
3.1: 35 - 40 °C
3.2: 35 - 85 °C / Reflux
4.1: hydrogen / methanol / 4654.46 - 5171.62 Torr / Autoclave
5.1: N-ethyl-N,N-diisopropylamine / water / 25 - 95 °C
6.1: thionyl chloride / dichloromethane / 2 h / 25 - 60 °C
6.2: 25 - 30 °C
View Scheme

: 41939-61-1
N1-methyl-4-nitrobenzene-1,2-diamine

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 35 - 40 °C 1.2: 80 - 85 °C 1.3: 25 - 30 °C 2.1: hydrogen / Raney nickel / methanol / 25 - 30 °C / 4654.46 - 5171.62 Torr 3.1: N-ethyl-N,N-diisopropylamine / water / 25 - 95 °C 4.1: thionyl chloride / dichloromethane / 25 - 60 °C 4.2: 55 - 60 °C View Scheme
Multi-step reaction with 4 steps 1.1: 35 - 40 °C 1.2: 35 - 85 °C / Reflux 2.1: hydrogen / methanol / 4654.46 - 5171.62 Torr / Autoclave 3.1: N-ethyl-N,N-diisopropylamine / water / 25 - 95 °C 4.1: thionyl chloride / dichloromethane / 2 h / 25 - 60 °C 4.2: 25 - 30 °C View Scheme

: 1313020-24-4
isopropyl 4-(5-bis(2-hydroxyethyl)amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Stage #1: isopropyl 4-(5-bis(2-hydroxyethyl)amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate With thionyl chloride In dichloromethane at 25 - 60℃; Stage #2: With hydrogenchloride In water at 55 - 60℃;
Stage #1: isopropyl 4-(5-bis(2-hydroxyethyl)amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate With thionyl chloride In dichloromethane at 25 - 60℃; for 2h; Stage #2: With water In dichloromethane at 25 - 30℃;	16.4 g

: 1374784-01-6
isopropyl 4-(1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butanoate

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogen / Raney nickel / methanol / 25 - 30 °C / 4654.46 - 5171.62 Torr 2.1: N-ethyl-N,N-diisopropylamine / water / 25 - 95 °C 3.1: thionyl chloride / dichloromethane / 25 - 60 °C 3.2: 55 - 60 °C View Scheme
Multi-step reaction with 3 steps 1.1: hydrogen / methanol / 4654.46 - 5171.62 Torr / Autoclave 2.1: N-ethyl-N,N-diisopropylamine / water / 25 - 95 °C 3.1: thionyl chloride / dichloromethane / 2 h / 25 - 60 °C 3.2: 25 - 30 °C View Scheme

: 109882-31-7
4-{5-[bis-(2-hydroxyethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}-butanoic acid methyl ester

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trichlorophosphate / 0.25 h / Reflux 2: hydrogenchloride / water / 0.25 h / 25 - 28 °C View Scheme
Stage #1: 4-{5-[bis-(2-hydroxyethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}-butanoic acid methyl ester With thionyl chloride In dichloromethane at 20 - 30℃; for 7h; Stage #2: With hydrogenchloride In dichloromethane at 20 - 70℃;

: 3543-72-4
4‐(1‐methyl‐5‐nitro‐1H‐benzoimidazol‐2‐yl)butyric acid ethyl ester

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: iron; hydrogenchloride; ammonium chloride / methanol; water / 2 h / 60 - 65 °C 2.1: sodium carbonate; sodium iodide / 65 - 70 °C 3.1: thionyl chloride / dichloromethane / 0 °C / Reflux 3.2: 80 - 90 °C View Scheme
Multi-step reaction with 4 steps 1: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr 2: potassium carbonate / water / 13.5 h / 69 - 70 °C / pH 4.2 - 5.5 / Large scale 3: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 4: hydrogenchloride / water; acetone / 40 - 75 °C View Scheme
Multi-step reaction with 4 steps 1: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr 2: diammonium hydrogenphosphate / water / 65 - 70 °C / pH 4.2 - 5.5 3: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 4: hydrogenchloride / water; acetone / 40 - 75 °C View Scheme
Multi-step reaction with 3 steps 1.1: 5% Pd/C-iron; hydrogen / ethanol / 3000.3 Torr 2.1: potassium iodide; diammonium phosphate / water / 65 - 70 °C / pH 4.2 - 5.5 3.1: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 3.2: 75 °C View Scheme

: 3543-73-5
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium carbonate; sodium iodide / 65 - 70 °C 2.1: thionyl chloride / dichloromethane / 0 °C / Reflux 2.2: 80 - 90 °C View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / water / 13.5 h / 69 - 70 °C / pH 4.2 - 5.5 / Large scale 2: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 3: hydrogenchloride / water; acetone / 40 - 75 °C View Scheme
Multi-step reaction with 3 steps 1: diammonium hydrogenphosphate / water / 65 - 70 °C / pH 4.2 - 5.5 2: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 3: hydrogenchloride / water; acetone / 40 - 75 °C View Scheme
Multi-step reaction with 2 steps 1.1: potassium iodide; diammonium phosphate / water / 65 - 70 °C / pH 4.2 - 5.5 2.1: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 2.2: 75 °C View Scheme
Multi-step reaction with 3 steps 1: acetic acid / water / -5 - 0 °C 2: thionyl chloride / dichloromethane / 2 h / -5 - 20 °C 3: hydrogenchloride / water / 4 h / Reflux View Scheme

: 369-36-8
6-fluoro-3-nitroaniline

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: toluene / 4 h / 70 - 85 °C 2.1: water / 3 h / 75 °C 2.2: 55 - 60 °C 3.1: sulfuric acid / 10 h / Reflux 4.1: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr 5.1: potassium carbonate / water / 13.5 h / 69 - 70 °C / pH 4.2 - 5.5 / Large scale 6.1: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 7.1: hydrogenchloride / water; acetone / 40 - 75 °C View Scheme
Multi-step reaction with 7 steps 1.1: toluene / 4 h / 70 - 85 °C 2.1: water / 3 h / 75 °C 2.2: 55 - 60 °C 3.1: sulfuric acid / 10 h / Reflux 4.1: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr 5.1: diammonium hydrogenphosphate / water / 65 - 70 °C / pH 4.2 - 5.5 6.1: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 7.1: hydrogenchloride / water; acetone / 40 - 75 °C View Scheme
Multi-step reaction with 5 steps 1.1: hydrogenchloride / toluene / 4 h / 85 °C 1.2: 3 h / 75 °C 2.1: sulfuric acid / 10 h / Reflux 3.1: 5% Pd/C-iron; hydrogen / ethanol / 3000.3 Torr 4.1: potassium iodide; diammonium phosphate / water / 65 - 70 °C / pH 4.2 - 5.5 5.1: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 5.2: 75 °C View Scheme

: 108-55-4
glutaric anhydride,

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: toluene / 4 h / 70 - 85 °C 2.1: water / 3 h / 75 °C 2.2: 55 - 60 °C 3.1: sulfuric acid / 10 h / Reflux 4.1: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr 5.1: potassium carbonate / water / 13.5 h / 69 - 70 °C / pH 4.2 - 5.5 / Large scale 6.1: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 7.1: hydrogenchloride / water; acetone / 40 - 75 °C View Scheme
Multi-step reaction with 7 steps 1.1: toluene / 4 h / 70 - 85 °C 2.1: water / 3 h / 75 °C 2.2: 55 - 60 °C 3.1: sulfuric acid / 10 h / Reflux 4.1: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr 5.1: diammonium hydrogenphosphate / water / 65 - 70 °C / pH 4.2 - 5.5 6.1: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 7.1: hydrogenchloride / water; acetone / 40 - 75 °C View Scheme
Multi-step reaction with 5 steps 1.1: hydrogenchloride / toluene / 4 h / 85 °C 1.2: 3 h / 75 °C 2.1: sulfuric acid / 10 h / Reflux 3.1: 5% Pd/C-iron; hydrogen / ethanol / 3000.3 Torr 4.1: potassium iodide; diammonium phosphate / water / 65 - 70 °C / pH 4.2 - 5.5 5.1: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 5.2: 75 °C View Scheme

: 31349-48-1
4-(1-methyl-5-nitro-1H-benzimidazol-2-yl)butanoic acid

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sulfuric acid / 10 h / Reflux 2: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr 3: potassium carbonate / water / 13.5 h / 69 - 70 °C / pH 4.2 - 5.5 / Large scale 4: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 5: hydrogenchloride / water; acetone / 40 - 75 °C View Scheme
Multi-step reaction with 5 steps 1: sulfuric acid / 10 h / Reflux 2: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr 3: diammonium hydrogenphosphate / water / 65 - 70 °C / pH 4.2 - 5.5 4: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 5: hydrogenchloride / water; acetone / 40 - 75 °C View Scheme
Multi-step reaction with 4 steps 1.1: sulfuric acid / 10 h / Reflux 2.1: 5% Pd/C-iron; hydrogen / ethanol / 3000.3 Torr 3.1: potassium iodide; diammonium phosphate / water / 65 - 70 °C / pH 4.2 - 5.5 4.1: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 4.2: 75 °C View Scheme

: bendamustine hydrochloride

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water; acetone at 40 - 75℃;	225 g

: 451459-95-3
5-(2-fluoro-5-nitroanilino)-5-oxopentanoic acid

: 3543-75-7
bendamustine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: water / 3 h / 75 °C 1.2: 55 - 60 °C 2.1: sulfuric acid / 10 h / Reflux 3.1: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr 4.1: potassium carbonate / water / 13.5 h / 69 - 70 °C / pH 4.2 - 5.5 / Large scale 5.1: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 6.1: hydrogenchloride / water; acetone / 40 - 75 °C View Scheme
Multi-step reaction with 6 steps 1.1: water / 3 h / 75 °C 1.2: 55 - 60 °C 2.1: sulfuric acid / 10 h / Reflux 3.1: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr 4.1: diammonium hydrogenphosphate / water / 65 - 70 °C / pH 4.2 - 5.5 5.1: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 6.1: hydrogenchloride / water; acetone / 40 - 75 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: water / 3 h / 75 °C
1.2: 55 - 60 °C
2.1: sulfuric acid / 10 h / Reflux
3.1: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr
4.1: potassium carbonate / water / 13.5 h / 69 - 70 °C / pH 4.2 - 5.5 / Large scale
5.1: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C
6.1: hydrogenchloride / water; acetone / 40 - 75 °C
View Scheme

Multi-step reaction with 6 steps
1.1: water / 3 h / 75 °C
1.2: 55 - 60 °C
2.1: sulfuric acid / 10 h / Reflux
3.1: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr
4.1: diammonium hydrogenphosphate / water / 65 - 70 °C / pH 4.2 - 5.5
5.1: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C
6.1: hydrogenchloride / water; acetone / 40 - 75 °C
View Scheme

: 2016-57-1
1-aminodecane

: 3543-75-7
bendamustine hydrochloride

: 1609623-14-4
4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}-N-decyl-butyramide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 2.7 - 10℃; for 1.5h; Inert atmosphere;	100%

: 112-53-8
1-dodecyl alcohol

: 3543-75-7
bendamustine hydrochloride

: 1456608-94-8
4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid dodecyl ester

Conditions

Conditions	Yield
Stage #1: bendamustine hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.733333h; Inert atmosphere; Stage #2: 1-dodecyl alcohol In dichloromethane for 0.183333h; Inert atmosphere; Stage #3: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 23.5h; Reagent/catalyst;	98%

: 64-17-5
ethanol

: 3543-75-7
bendamustine hydrochloride

: 4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid ethyl ester

Conditions

Conditions	Yield
With methanesulfonic acid at 70℃; for 1h; Inert atmosphere;	97%

: 67-56-1
methanol

: 3543-75-7
bendamustine hydrochloride

: 109882-25-9
4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid methyl ester

Conditions

Conditions	Yield
With methanesulfonic acid at 65℃; for 1h; Inert atmosphere;	94%

: 3543-75-7
bendamustine hydrochloride

: 16506-27-7
bendamustine

Conditions

Conditions	Yield
With triethylamine In methanol other reagent;	89%

: 112-30-1
1-Decanol

: 3543-75-7
bendamustine hydrochloride

: 1609623-04-2
4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid decyl ester

Conditions

Conditions	Yield
Stage #1: bendamustine hydrochloride With triethylamine In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: 1-Decanol With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 20h; Reagent/catalyst; Time; Inert atmosphere;	88.6%

: 3543-75-7
bendamustine hydrochloride

: 1221157-14-7
4-(5-(bis(2-chloroethyl)amino)-1-methyl-1H-benzo[d]imidazol-2-yl)butan-1-ol

Conditions

Conditions	Yield
With borane-THF In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	86%

: 64-17-5
ethanol

: 3543-75-7
bendamustine hydrochloride

: bendamustine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride for 4h; Ambient temperature;	85%

: 3543-75-7
bendamustine hydrochloride

: bendamustine hydrazide

Conditions

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride for 12h;	82.4%

: 3543-75-7
bendamustine hydrochloride

: 109882-29-3
4-<1-Methyl-5-benzimidazolyl-(2)>butansaeure-hydrochlorid

Conditions

Conditions	Yield
With water at 95℃; for 5h;	82%

: 688009-09-8
4-amino-1-((2R,4R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3,3-difluoro-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

: 3543-75-7
bendamustine hydrochloride

: 4-(5-(bis(2-chloroethyl)amino)-1-methyl-1H-benzo[d]imidazol-2-yl)-N-(1-((2R,4R,5R)- 4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3,3-difluorotetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-butanamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 40℃; for 12h;	79%

: 112-92-5
1-octadecanol

: 3543-75-7
bendamustine hydrochloride

: 1609623-08-6
C34H57Cl2N3O2

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;	73%

: 97682-44-5, 130144-33-1
irinotecan

: 3543-75-7
bendamustine hydrochloride

: C49H57Cl2N7O7

Conditions

Conditions	Yield
Stage #1: bendamustine hydrochloride With triethylamine; dicyclohexyl-carbodiimide In chloroform at 0℃; for 0.5h; Stage #2: irinotecan With dmap In chloroform at 0 - 20℃; for 48h; Darkness;	69%

: 1068-57-1
acetic acid hydrazide

: 3543-75-7
bendamustine hydrochloride

: C18H25Cl2N5O2

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-hydroxysulfosuccinimide sodium salt In water at 20℃; for 12.5h;	66.1%

: 2491-20-5
L-alanine methyl ester hydrochloride

: 3543-75-7
bendamustine hydrochloride

: 1609623-17-7
(S)-2-(4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyrylamino)propionic acid methyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 1.9 - 20℃; for 4h; Inert atmosphere;	63.3%

: 3543-75-7
bendamustine hydrochloride

: 50-91-9
5-Fluoro-2'-deoxyuridine

: C25H30Cl2FN5O6

Conditions

Conditions	Yield
Stage #1: bendamustine hydrochloride With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 5-Fluoro-2'-deoxyuridine With dmap; triethylamine In N,N-dimethyl-formamide at 25℃; for 48h; Darkness;	61%

: 2016-42-4
tetradecylamine

: 3543-75-7
bendamustine hydrochloride

: 1609623-15-5
4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}-N-tetradecyl-butyramide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 3.3 - 20℃; for 3h; Inert atmosphere;	57.6%

: 3543-75-7
bendamustine hydrochloride

: 879126-98-4, 879126-99-5, 191732-72-6
Lenalidomide

: 4-(5-(bis(2-chloroethyl)amino)-1-methyl-1H-benzo[d]imidazol-2-yl)-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindoline-4-yl)butanamide

Conditions

Conditions	Yield
With dmap; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 40℃;	51%

: 5-hydroxymicheliolide

: 3543-75-7
bendamustine hydrochloride

: C31H39Cl2N3O5

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	48.3%

: 661-19-8
1-docosanol

: 3543-75-7
bendamustine hydrochloride

: 1609623-09-7
4-{5-[bis-(chloroethyl)amino]-1-methyl-1H-benzimidazol-2-yl}butyric acid docosyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;	43.1%

: 10203-28-8
rac-2-dodecanol

: 3543-75-7
bendamustine hydrochloride

: 1609623-10-0
4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid 2-dodecyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;	40%

: 112-72-1
1-Tetradecanol

: 3543-75-7
bendamustine hydrochloride

: 1609623-05-3
4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid tetradecyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 20h; Inert atmosphere;	36.4%

: 3543-75-7
bendamustine hydrochloride

: 108-93-0
cyclohexanol

: 1609623-12-2
4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid cyclohexyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h; Inert atmosphere;	27.9%

: 5205-34-5
decan-5-ol

: 3543-75-7
bendamustine hydrochloride

: 1609623-11-1
4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid 5-decyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In 1,2-dichloro-ethane at 75℃; for 120h; Inert atmosphere;	24.2%

: 3543-75-7
bendamustine hydrochloride

A: 109882-29-3
4-<1-Methyl-5-benzimidazolyl-(2)>butansaeure-hydrochlorid

B: 109882-26-0
4-(6-((2-chloroethyl)(2-hydroxyethyl)amino)-3-methylbenzimidazolyl(2))butyric acid hydrochloride

Conditions

Conditions	Yield
With water at 95℃; for 1h;

Bendamustine hydrochloride Chemical Properties

The molecular structure of Bendamustine hydrochloride (CAS NO.3543-75-7):

IUPAC Name: 4-[5-[Bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoic acid hydrochloride
Molecular Weight: 394.72378 g/mol
Molecular Formula: C₁₆H₂₂Cl₃N₃O₂
Melting Point: 149-151 °C
Flash Point: 307.7 °C
Enthalpy of Vaporization: 91.95 kJ/mol
Boiling Point: 585.2 °C at 760 mmHg
Vapour Pressure: 1.55E-14 mmHg at 25 °C
H-Bond Donor: 2
H-Bond Acceptor: 4
Rotatable Bond Count: 9
Tautomer Count: 2
Exact Mass: 393.07776
MonoIsotopic Mass: 393.07776
Topological Polar Surface Area: 58.4
Heavy Atom Count: 24
Canonical SMILES: CN1C2=C(C=C(C=C2)N(CCCl)CCCl)N=C1CCCC(=O)O.Cl
InChI: InChI=1S/C16H21Cl2N3O2.ClH/c1-20-14-6-5-12(21(9-7-17)10-8-18)11-13(14)19-15(20)3-2-4-16(22)23;/h5-6,11H,2-4,7-10H2,1H3,(H,22,23);1H
InChIKey: ZHSKUOZOLHMKEA-UHFFFAOYSA-N
Product Categories: API intermediates; Intermediates & Fine Chemicals; Pharmaceuticals

Bendamustine hydrochloride Uses

Bendamustine hydrochloride (CAS NO.3543-75-7) is used as an anticancer drug.

Bendamustine hydrochloride Toxicity Data With Reference

1.	orl-mus TDLo:250 mg/kg/4D-I:CAR	ARGEAR Archiv fuer Geschwulstforschung. 43 (1974),16.
2.	ipr-mus TDLo:50 mg/kg/4D-I:CAR	ARGEAR Archiv fuer Geschwulstforschung. 43 (1974),16.
3.	orl-rat LD50:200 mg/kg	ATSUDG Archives of Toxicology, Supplement. 8 (1985),504.
4.	ivn-rat LD50:40 mg/kg	ATSUDG Archives of Toxicology, Supplement. 8 (1985),504.
5.	orl-mus LD50:250 mg/kg	ARGEAR Archiv fuer Geschwulstforschung. 43 (1974),16.
6.	ipr-mus LD50:100 mg/kg	ARGEAR Archiv fuer Geschwulstforschung. 43 (1974),16.
7.	ivn-mus LD50:80 mg/kg	ATSUDG Archives of Toxicology, Supplement. 8 (1985),504.

Bendamustine hydrochloride Safety Profile

A poison by ingestion, intravenous, and intraperitoneal routes. Questionable carcinogen with experimental carcinogenic and teratogenic data. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of HCl and NO_x.

Bendamustine hydrochloride Specification

Bendamustine hydrochloride (CAS NO.3543-75-7) is also named as Bendamustin hydrochloride ; Bendamustine HCl ; CCRIS 1864 ; Cytostasan ; IMET 3393 ; NSC 138783 ; Ribomustin ; SDX 105 ; Treanda ; UNII-981Y8SX18M ; gamma(1-Methyl-5-bis(beta-chloraethyl)aminobenzimidazoyl-2)buttersaeurehydrochlorid ; gamma(1-Methyl-5-bis(beta-chloraethyl)aminobenzimidazoyl-2)buttersaeurehydrochlorid [German] . Bendamustine hydrochloride (CAS NO.3543-75-7) is pale brown crystals.

Product Name

Bendamustine hydrochloride

Synthetic route

Bendamustine hydrochloride Chemical Properties

Bendamustine hydrochloride Uses

Bendamustine hydrochloride Toxicity Data With Reference

Bendamustine hydrochloride Safety Profile

Bendamustine hydrochloride Specification

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