Product Name

  • Name

    2-Butyl-1H-imidazole-4-carbaldehyde

  • EINECS 614-393-7
  • CAS No. 68282-49-5
  • Article Data16
  • CAS DataBase
  • Density 1.099 g/cm3
  • Solubility
  • Melting Point 118-119 oC
  • Formula C8H12N2O
  • Boiling Point 359.1 °C at 760 mmHg
  • Molecular Weight 152.196
  • Flash Point 174.8 °C
  • Transport Information
  • Appearance white solid
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 68282-49-5 (2-Butyl-1H-imidazole-4-carbaldehyde)
  • Hazard Symbols IrritantXi
  • Synonyms 1H-Imidazole-4-carboxaldehyde,2-butyl- (9CI);2-Butyl-1H-imidazole-4-carboxaldehyde;2-Butyl-1H-imidazole-5-carboxaldehyde;2-Butyl-3H-imidazole-4-carboxaldehyde;2-Butyl-4-formylimidazole;2-Butyl-5-formylimidazole;2-n-Butyl-4-formylimidazole;2-n-Butyl-4-imidazolecarboxaldehyde;2-n-Butyl-5-imidazolecarboxaldehyde;2-butyl-1H-imidazole-5-carbaldehyde;1H-imidazole-5-carboxaldehyde, 2-butyl-;
  • PSA 45.75000
  • LogP 1.56480

Synthetic route

2-butyl-5-hydroxymethyl-1H-imidazole
68283-19-2

2-butyl-5-hydroxymethyl-1H-imidazole

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

Conditions
ConditionsYield
With oxygen; 2percent V/C In various solvent(s) at 105℃; under 750.075 Torr; for 6h;100%
With manganese(IV) oxide In dichloromethane Oxidation;
bismuth
7440-69-9

bismuth

aqueous H2 O2

aqueous H2 O2

sulfuric acid
7664-93-9

sulfuric acid

pyrographite
7440-44-0

pyrographite

2-butyl-5-hydroxymethyl-1H-imidazole
68283-19-2

2-butyl-5-hydroxymethyl-1H-imidazole

platinum
7440-06-4

platinum

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

Conditions
ConditionsYield
With sodium hydroxide In water100%
With sodium hydroxide In water98.2%
With sodium hydroxide In methanol; water94.5%
...Expand
bismuth
7440-69-9

bismuth

pyrographite
7440-44-0

pyrographite

2-butyl-5-hydroxymethyl-1H-imidazole
68283-19-2

2-butyl-5-hydroxymethyl-1H-imidazole

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

platinum
7440-06-4

platinum

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

Conditions
ConditionsYield
With sodium hydroxide In dodecane; water90%
...Expand
bismuth
7440-69-9

bismuth

aqueous H2 O2

aqueous H2 O2

pyrographite
7440-44-0

pyrographite

2-butyl-5-hydroxymethyl-1H-imidazole
68283-19-2

2-butyl-5-hydroxymethyl-1H-imidazole

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

platinum
7440-06-4

platinum

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

Conditions
ConditionsYield
With sodium hydroxide In dodecane; water88.2%
...Expand
2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde
83857-96-9

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

Conditions
ConditionsYield
Stage #1: 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde With hydrogen; triethylamine; palladium 10% on activated carbon In methanol at 20 - 25℃; under 2942.29 - 3677.86 Torr; for 8 - 10h;
Stage #2: With hydrogenchloride In water at 25 - 30℃; pH=1.2;
Stage #3: With sodium carbonate In water pH=6.8 - 7.5; Product distribution / selectivity;		74%
2-n-butyl-4-(hydroxymethyl)imidazole
68283-19-2

2-n-butyl-4-(hydroxymethyl)imidazole

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

Conditions
ConditionsYield
With sodium hydroxide; bismuth(III) sulfate; dihydrogen peroxide; platinum on carbon In water at 20 - 62℃; for 3.5 - 4.5h; Product distribution / selectivity;61%
2-butyl-1H-imidazole
50790-93-7

2-butyl-1H-imidazole

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2O
2: MnO2 / CH2Cl2
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C
1.2: 2 h / 0 - 25 °C
2.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere
2.2: -78 - -50 °C / Inert atmosphere
2.3: 2 h / 0 - 25 °C
View Scheme
pentanonitrile
110-59-8

pentanonitrile

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 72 percent / hydrogen chloride / 18 h / 0 - 15 °C
2: 75 percent / NH3 / 60 °C / high pressure
3: MnO2 / CH2Cl2
View Scheme
2-butyl-3-dimethylaminomethylimidazole

2-butyl-3-dimethylaminomethylimidazole

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

Conditions
ConditionsYield
With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane; N,N-dimethyl-formamide
2-butyl-3-dimethylaminosulfonylimidazole
148454-64-2

2-butyl-3-dimethylaminosulfonylimidazole

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

Conditions
ConditionsYield
Stage #1: 2-butyl-3-dimethylaminosulfonylimidazole With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - -50℃; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0 - 25℃; for 2h;
Methyl 4-(bromomethyl)benzoate
2417-72-3

Methyl 4-(bromomethyl)benzoate

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

A

2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde
133040-03-6

2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde

B

methyl 4-[(2-butyl-4-formyl-1H-imidazol-1-yl)methyl]benzoate
159708-89-1

methyl 4-[(2-butyl-4-formyl-1H-imidazol-1-yl)methyl]benzoate

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Substitution;A 27%
B 54%
Stage #1: 2-butyl-1H-imidazole-5-carboxaldehyde With tetraethylammonium hydroxide In N,N-dimethyl-formamide for 1h; deprotonation;
Stage #2: Methyl 4-(bromomethyl)benzoate In water; N,N-dimethyl-formamide at 0 - 20℃; for 3h; Alkylation;		A 40%
B 54%
With sodium carbonate In N,N-dimethyl-formamide at 70℃; Alkylation;
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
...Expand
Methyl 4'-(bromomethyl)biphenyl-2-carboxylate
114772-38-2

Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

A

2-butyl-1-<(2'-carbomethoxy<1,1'-biphenyl>-4-yl)methyl>-1H-imidazole-5-carboxaldehyde
152147-96-1

2-butyl-1-<(2'-carbomethoxy<1,1'-biphenyl>-4-yl)methyl>-1H-imidazole-5-carboxaldehyde

B

4'-(2-butyl-4-formyl-imidazol-1-ylmethyl)-biphenyl-2-carboxylic acid methyl ester
470691-30-6

4'-(2-butyl-4-formyl-imidazol-1-ylmethyl)-biphenyl-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 25℃;A 23%
B 48%
...Expand
(1R,2R,3R,5S)-(-)-Isopinocampheylamine
69460-11-3

(1R,2R,3R,5S)-(-)-Isopinocampheylamine

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

(1R,2R,3R,5S)-N-((2-butyl-1H-imidazol-5-yl)methyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-amine hydrochloride

(1R,2R,3R,5S)-N-((2-butyl-1H-imidazol-5-yl)methyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-amine hydrochloride

Conditions
ConditionsYield
Stage #1: (1R,2R,3R,5S)-(-)-Isopinocampheylamine; 2-butyl-1H-imidazole-5-carboxaldehyde With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 1.5h; Inert atmosphere;
Stage #2: With hydrogenchloride In ethyl acetate		44%
pyrrole
109-97-7

pyrrole

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

meso-tetrakis(2-n-butylimidazol-5-yl)porphyrin

meso-tetrakis(2-n-butylimidazol-5-yl)porphyrin

Conditions
ConditionsYield
In propionic acid for 1h; Heating;26%
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde
83857-96-9

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde

Conditions
ConditionsYield
With N-chloro-succinimide Chlorination;
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

4-[2-butyl-5-(2-ethoxycarbonyl-2-phenylsulfanyl-vinyl)-imidazol-1-ylmethyl]-benzoic acid ethyl ester
220579-46-4

4-[2-butyl-5-(2-ethoxycarbonyl-2-phenylsulfanyl-vinyl)-imidazol-1-ylmethyl]-benzoic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: Na2CO3 / dimethylformamide / 70 °C
2.2: ethanol
View Scheme
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

4-[2-butyl-4-(2-ethoxycarbonyl-2-phenylsulfanyl-vinyl)-imidazol-1-ylmethyl]-benzoic acid ethyl ester
220579-42-0

4-[2-butyl-4-(2-ethoxycarbonyl-2-phenylsulfanyl-vinyl)-imidazol-1-ylmethyl]-benzoic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: Na2CO3 / dimethylformamide / 70 °C
2.2: ethanol
View Scheme
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

C24H22N2O4S(2-)*2Na(1+)

C24H22N2O4S(2-)*2Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: Na2CO3 / dimethylformamide / 70 °C
2.2: ethanol
3.1: NaOH / ethanol; H2O / Alkaline hydrolysis
View Scheme
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

C24H22N2O4S(2-)*2Na(1+)

C24H22N2O4S(2-)*2Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: Na2CO3 / dimethylformamide / 70 °C
2.2: ethanol
3.1: NaOH / ethanol; H2O / Alkaline hydrolysis
View Scheme
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

4'-[5-((Z)-2-Azido-2-methoxycarbonyl-vinyl)-2-butyl-imidazol-1-ylmethyl]-biphenyl-2-carboxylic acid methyl ester
470691-32-8

4'-[5-((Z)-2-Azido-2-methoxycarbonyl-vinyl)-2-butyl-imidazol-1-ylmethyl]-biphenyl-2-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 23 percent / potassium carbonate / dimethylformamide / 25 °C
2: 42 percent / sodium; methanol / -15 °C
View Scheme
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

4'-[4-((E)-2-Azido-2-methoxycarbonyl-vinyl)-2-butyl-imidazol-1-ylmethyl]-biphenyl-2-carboxylic acid methyl ester
470691-34-0

4'-[4-((E)-2-Azido-2-methoxycarbonyl-vinyl)-2-butyl-imidazol-1-ylmethyl]-biphenyl-2-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 48 percent / potassium carbonate / dimethylformamide / 25 °C
2: 40 percent / sodium; methanol / -15 °C
View Scheme
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

methyl 2-(n-butyl)-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]pyrrolo[2,3-d]imidazole-5-carboxylate

methyl 2-(n-butyl)-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]pyrrolo[2,3-d]imidazole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 23 percent / potassium carbonate / dimethylformamide / 25 °C
2: 42 percent / sodium; methanol / -15 °C
3: 32 percent / xylene / Heating
View Scheme
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

methyl 2-(n-butyl)-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]pyrrolo[3,2-d]imidazole-5-carboxylate
470691-39-5

methyl 2-(n-butyl)-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]pyrrolo[3,2-d]imidazole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 48 percent / potassium carbonate / dimethylformamide / 25 °C
2: 40 percent / sodium; methanol / -15 °C
3: 35 percent / xylene / Heating
View Scheme
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

α-azido-β-[2-butyl-1-(4-carbethoxybenzyl)imidazol-5-yl]acrylate

α-azido-β-[2-butyl-1-(4-carbethoxybenzyl)imidazol-5-yl]acrylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 27 percent / sodium carbonate / dimethylformamide / 24 h / 100 °C
2: 66 percent / NaOEt / tetrahydrofuran / 2 h / -10 °C
View Scheme
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

ethyl 2-butyl-1-(4-carbethoxybenzyl)pyrrolo[3,2-d]imidazole-5-carboxylate

ethyl 2-butyl-1-(4-carbethoxybenzyl)pyrrolo[3,2-d]imidazole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 54 percent / sodium carbonate / dimethylformamide / 24 h / 100 °C
2: 40 percent / NaOEt / tetrahydrofuran / 2 h / -10 °C
3: 28 percent / xylene / 2 h / Heating
View Scheme
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 27 percent / sodium carbonate / dimethylformamide / 24 h / 100 °C
2: 66 percent / NaOEt / tetrahydrofuran / 2 h / -10 °C
3: 22 percent / xylene / 2 h / Heating
View Scheme
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

α-azido-β-[2-butyl-1-(4-carbethoxybenzyl)imidazol-4-yl]acrylate
203204-02-8

α-azido-β-[2-butyl-1-(4-carbethoxybenzyl)imidazol-4-yl]acrylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 54 percent / sodium carbonate / dimethylformamide / 24 h / 100 °C
2: 40 percent / NaOEt / tetrahydrofuran / 2 h / -10 °C
View Scheme
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde
133040-03-6

2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-chlorosuccinimide
2: K2CO3 / dimethylformamide
3: H2 / Pd/C
View Scheme
2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

2-butyl-4-chloro-1-<(4-carbomethoxyphenyl)methyl>-1H-imidazole-5-carboxaldehyde
133040-02-5

2-butyl-4-chloro-1-<(4-carbomethoxyphenyl)methyl>-1H-imidazole-5-carboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-chlorosuccinimide
2: K2CO3 / dimethylformamide
View Scheme
Chloromethyl pivalate
18997-19-8

Chloromethyl pivalate

methyl (E)-3-<2-butyl-1-<(2-chlorophenyl)methyl>imidazol-5-yl>-2-<(2-thienyl)methyl>-2-propenoate
133485-47-9

methyl (E)-3-<2-butyl-1-<(2-chlorophenyl)methyl>imidazol-5-yl>-2-<(2-thienyl)methyl>-2-propenoate

2-butyl-1H-imidazole-5-carboxaldehyde
68282-49-5

2-butyl-1H-imidazole-5-carboxaldehyde

2-n-butyl-1-pivalyloxymethylimidazol-5-carboxaldehyde
133486-33-6

2-n-butyl-1-pivalyloxymethylimidazol-5-carboxaldehyde

Conditions
ConditionsYield
With manganese dioxide; potassium carbonate In N-methyl-acetamide
...Expand

2-Butyl-1H-imidazole-4-carbaldehyde Specification

The 1H-Imidazole-5-carboxaldehyde,2-butyl-, with the CAS registry number 68282-49-5, has the systematic name of 2-butyl-1H-imidazole-5-carbaldehyde. And the molecular formula of this chemical is C8H12N2O. It belongs to the product categories of Imidazol and Benzimidazole.

The physical properties of 1H-Imidazole-5-carboxaldehyde,2-butyl- are as following: (1)ACD/LogP: 0.65; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.63; (4)ACD/LogD (pH 7.4): 0.65; (5)ACD/BCF (pH 5.5): 1.74; (6)ACD/BCF (pH 7.4): 1.82; (7)ACD/KOC (pH 5.5): 51.19; (8)ACD/KOC (pH 7.4): 53.44; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 34.89 Å2; (13)Index of Refraction: 1.553; (14)Molar Refractivity: 44.34 cm3; (15)Molar Volume: 138.4 cm3; (16)Polarizability: 17.57×10-24cm3; (17)Surface Tension: 46.8 dyne/cm; (18)Density: 1.099 g/cm3; (19)Flash Point: 174.8 °C; (20)Enthalpy of Vaporization: 60.46 kJ/mol; (21)Boiling Point: 359.1 °C at 760 mmHg; (22)Vapour Pressure: 2.44E-05 mmHg at 25°C.

Uses of 1H-Imidazole-5-carboxaldehyde,2-butyl-: It can react with 2,2-dimethyl-propionic acid chloromethyl ester to produce 2,2-dimethyl-propionic acid 2-butyl-4-formyl-imidazol-1-ylmethyl ester. This reaction will need reagent K2CO3 and solvent dimethylformamide. The reaction time is 22 hours with temperature of 25°C, and the yield is about 99%. 

1H-Imidazole-5-carboxaldehyde,2-butyl- can react with 2,2-dimethyl-propionic acid chloromethyl ester to produce 2,2-dimethyl-propionic acid 2-butyl-4-formyl-imidazol-1-ylmethyl ester
 
You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=Cc1cnc(n1)CCCC
(2)InChI: InChI=1/C8H12N2O/c1-2-3-4-8-9-5-7(6-11)10-8/h5-6H,2-4H2,1H3,(H,9,10)
(3)InChIKey: PTHGVOCFAZSNNA-UHFFFAOYAB

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