Product Name

  • Name

    305-03-3

  • EINECS 206-162-0
  • CAS No. 305-03-3
  • Article Data38
  • CAS DataBase
  • Density 1.248 g/cm3
  • Solubility <0.01 g/100 mL at 22 °C in water
  • Melting Point 65-70 °C
  • Formula C14H19Cl2NO2
  • Boiling Point 460.09 °C at 760 mmHg
  • Molecular Weight 304.216
  • Flash Point 232.054 °C
  • Transport Information UN 2811 6.1/PG 3
  • Appearance beige powder
  • Safety 53-26-45
  • Risk Codes 45-25-36/37/38
  • Molecular Structure Molecular Structure of 305-03-3 (305-03-3)
  • Hazard Symbols ToxicT
  • Synonyms Butyricacid, 4-[p-[bis(2-chloroethyl)amino]phenyl]- (8CI);4-[Bis(2-chloroethyl)amino]benzenebutanoic acid;Ambochlorin;Amboclorin;CB 1348;Chloraminophene;Ecloril;Leukeran;Leukeran Tablets;Linfolizin;Linfolysin;Lympholysin;NCI 3088;NSC 3088;g-[p-Di(2-chloroethyl)aminophenyl]butyricacid;Chlorambucil;
  • PSA 40.54000
  • LogP 3.37790

Synthetic route

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

2-(4-(N,N-bis(2-chloroethyl)amino)phenyl)acetaldehyde
500590-36-3

2-(4-(N,N-bis(2-chloroethyl)amino)phenyl)acetaldehyde

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
With formic acid; triethylamine at 50 - 95℃; for 5h; Temperature;76.9%
4-(4-(bis(2-chloroethyl)amino)phenyl)-4-oxobutanoic acid

4-(4-(bis(2-chloroethyl)amino)phenyl)-4-oxobutanoic acid

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
With formic acid; 1,1,1,3',3',3'-hexafluoro-propanol; water at 80℃; for 2h; Sealed tube; chemoselective reaction;54%
methyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
79481-83-7

methyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
With hydrogenchloride In water at 60℃; for 1h;53.1%
With hydrogenchloride 1.) 60 deg C, 30 min, 2.) reflux, 10 min; Yield given;
With hydrogenchloride Heating;
4-(4-(bis(2-chloroethyl)amino)phenyl)-N-(quinolin-8-yl)butanamide

4-(4-(bis(2-chloroethyl)amino)phenyl)-N-(quinolin-8-yl)butanamide

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
With water; sodium hydroxide In water for 12h; Reflux;41%
oxirane
75-21-8

oxirane

methyl 4-(4-aminophenyl)butanoate
20637-09-6

methyl 4-(4-aminophenyl)butanoate

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
With acetic acid Erwaermen des Reaktionsprodukts mit POCl3 in Benzol und Erhitzen des erhaltenen Esters mit konz. wss. HCl;
methyl 4-(4-aminophenyl)butanoate
20637-09-6

methyl 4-(4-aminophenyl)butanoate

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid
2: phosphorus oxychloride / toluene / Heating
3: hydrochloric acid / Heating
View Scheme
Multi-step reaction with 3 steps
1: AcOH / tetrahydrofuran / 48 h / 110 - 120 °C
2: POCl3 / benzene / 1 h / Heating
3: concd. HCl / 1.) 60 deg C, 30 min, 2.) reflux, 10 min
View Scheme
methyl 3-<4-phenyl>butyrate
130198-76-4

methyl 3-<4-phenyl>butyrate

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: phosphorus oxychloride / toluene / Heating
2: hydrochloric acid / Heating
View Scheme
Multi-step reaction with 2 steps
1: POCl3 / benzene / 1 h / Heating
2: concd. HCl / 1.) 60 deg C, 30 min, 2.) reflux, 10 min
View Scheme
methyl 4-(4-nitrophenyl)butanoate
20637-02-9

methyl 4-(4-nitrophenyl)butanoate

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H2 / Pd/C / ethyl acetate
2: AcOH / tetrahydrofuran / 48 h / 110 - 120 °C
3: POCl3 / benzene / 1 h / Heating
4: concd. HCl / 1.) 60 deg C, 30 min, 2.) reflux, 10 min
View Scheme
(3β)-3-hydroxyandrost-5-en-17-one 4-{4-[di(2-chloroethyl)amino]phenyl}butyrate
901771-68-4

(3β)-3-hydroxyandrost-5-en-17-one 4-{4-[di(2-chloroethyl)amino]phenyl}butyrate

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
With porcine liver esterase; disodium hydrogenphosphate; sodium dihydrogenphosphate; potassium chloride; sodium chloride In ethanol; water at 37℃; for 24h; Enzymatic reaction;
(3β)-3-hydroxyandrost-5-en-17-one 4-{4-[di(2-chloroethyl)amino]-3-nitrophenyl}butyrate
1165715-35-4

(3β)-3-hydroxyandrost-5-en-17-one 4-{4-[di(2-chloroethyl)amino]-3-nitrophenyl}butyrate

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
With porcine liver esterase; disodium hydrogenphosphate; sodium dihydrogenphosphate; potassium chloride; sodium chloride In ethanol; water at 37℃; for 24h; Enzymatic reaction;
(3β)-3-hydroxypregn-5-en-20-one 4-{4-[di(2-chloroethyl)amino]phenyl}butyrate
1085269-21-1

(3β)-3-hydroxypregn-5-en-20-one 4-{4-[di(2-chloroethyl)amino]phenyl}butyrate

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
With porcine liver esterase; disodium hydrogenphosphate; sodium dihydrogenphosphate; potassium chloride; sodium chloride In ethanol; water at 37℃; for 24h; Enzymatic reaction;
(3β)-3-hydroxypregn-5-en-20-one 4-{4-[di(2-chloroethyl)amino]-3-nitro-phenyl}butyrate
1165715-39-8

(3β)-3-hydroxypregn-5-en-20-one 4-{4-[di(2-chloroethyl)amino]-3-nitro-phenyl}butyrate

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
With porcine liver esterase; disodium hydrogenphosphate; sodium dihydrogenphosphate; potassium chloride; sodium chloride In ethanol; water at 37℃; for 24h; Enzymatic reaction;
(E)-5-(4-ethoxystyryl)-2-nitrobenzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
1384982-40-4

(E)-5-(4-ethoxystyryl)-2-nitrobenzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

A

C17H15NO3

C17H15NO3

B

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
In acetonitrile Irradiation;
(E)-2-nitro-5-(4-((tetrahydro-2H-pyran-2-yl)oxy)styryl)benzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
1384982-50-6

(E)-2-nitro-5-(4-((tetrahydro-2H-pyran-2-yl)oxy)styryl)benzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C / Darkness
2: Irradiation
View Scheme
Multi-step reaction with 3 steps
1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C / Darkness
2: triethylamine / dichloromethane / 12 h / 0 °C / Darkness
3: Irradiation
View Scheme
Multi-step reaction with 3 steps
1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C / Darkness
2: potassium carbonate / acetonitrile / 5 h / 55 °C / Darkness
3: Irradiation
View Scheme
Multi-step reaction with 3 steps
1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C / Darkness
2: potassium carbonate / acetone / 6 h / 20 °C / Darkness
3: Irradiation
View Scheme
Multi-step reaction with 4 steps
1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C / Darkness
2: potassium carbonate / acetonitrile / 24 h / 20 °C / Darkness
3: trifluoroacetic acid / dichloromethane / 24 h / 20 °C / Darkness
4: Irradiation
View Scheme
(E)-5-(4-(2,2-dimethoxyethoxy)styryl)-2-nitrobenzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
1384982-53-9

(E)-5-(4-(2,2-dimethoxyethoxy)styryl)-2-nitrobenzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C / Darkness
2: Irradiation
View Scheme
(E)-5-(4-hydroxystyryl)-2-nitrobenzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
1384982-41-5

(E)-5-(4-hydroxystyryl)-2-nitrobenzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

A

C15H11NO3

C15H11NO3

B

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
Irradiation;
(E)-5-(4-hydroxystyryl)-2-nitrobenzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
1384982-41-5

(E)-5-(4-hydroxystyryl)-2-nitrobenzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / acetonitrile / 5 h / 55 °C / Darkness
2: Irradiation
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / 6 h / 20 °C / Darkness
2: Irradiation
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 12 h / 0 °C / Darkness
2: Irradiation
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / acetonitrile / 24 h / 20 °C / Darkness
2: trifluoroacetic acid / dichloromethane / 24 h / 20 °C / Darkness
3: Irradiation
View Scheme
(E)-2-nitro-5-(4-(prop-2-yn-1-yloxy)styryl)benzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
1384982-42-6

(E)-2-nitro-5-(4-(prop-2-yn-1-yloxy)styryl)benzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

A

C18H13NO3

C18H13NO3

B

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
Irradiation;
(E)-2-(4-(3-(((4-(4-(bis(2-chloroethyl)amino)phenyl)butanoyl)oxy)methyl)-4-nitrostyryl)phenoxy)acetic acid
1384982-43-7

(E)-2-(4-(3-(((4-(4-(bis(2-chloroethyl)amino)phenyl)butanoyl)oxy)methyl)-4-nitrostyryl)phenoxy)acetic acid

A

C17H13NO5

C17H13NO5

B

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
Irradiation;
C35H40Cl2N2O7

C35H40Cl2N2O7

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C / Darkness
2: Irradiation
View Scheme
(E)-5-(4-(4-bromobutoxy)styryl)-2-nitrobenzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
1384982-44-8

(E)-5-(4-(4-bromobutoxy)styryl)-2-nitrobenzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

A

C19H18BrNO3

C19H18BrNO3

B

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
Irradiation;
(E)-5-(4-(methacryloyloxy)styryl)-2-nitrobenzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

(E)-5-(4-(methacryloyloxy)styryl)-2-nitrobenzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

A

C19H15NO4

C19H15NO4

B

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
Irradiation;
(E)-2-nitro-5-(4-(2-oxoethoxy)styryl)benzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
1384982-46-0

(E)-2-nitro-5-(4-(2-oxoethoxy)styryl)benzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

A

C17H13NO4

C17H13NO4

B

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
Irradiation;
(benzo[a]acridin-12-yl)methyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
1609956-68-4

(benzo[a]acridin-12-yl)methyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
In water; acetonitrile UV-irradiation;
C31H29Cl2NO2

C31H29Cl2NO2

A

1-pyrenemethanol
24463-15-8

1-pyrenemethanol

B

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
With water at 20℃; for 0.166667h; UV-irradiation;
C31H28Cl2N2O5S

C31H28Cl2N2O5S

A

8-benzothiazoyl-7-hydroxyl-4-(hydroxymethyl)coumarin

8-benzothiazoyl-7-hydroxyl-4-(hydroxymethyl)coumarin

B

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
In methanol; water Kinetics; Quantum yield; UV-irradiation;
(E)-2-(6-(2-((3-(3,4-dihydroxyphenyl)acryloyl)oxy)acetyl)-9-ethyl-9H-carbazol-3-yl)-2-oxoethyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

(E)-2-(6-(2-((3-(3,4-dihydroxyphenyl)acryloyl)oxy)acetyl)-9-ethyl-9H-carbazol-3-yl)-2-oxoethyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

A

caffeic acid
331-39-5

caffeic acid

B

2-(9-ethyl-9H-carbazol-3-yl)-2-oxoethyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

2-(9-ethyl-9H-carbazol-3-yl)-2-oxoethyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

C

3,6-bis(hydroxyacetyl)-9-ethyl-9H-carbazole

3,6-bis(hydroxyacetyl)-9-ethyl-9H-carbazole

D

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
In water; acetonitrile for 1h; UV-irradiation;
C37H36Cl2N4O4S

C37H36Cl2N4O4S

A

C22H17N3O3S

C22H17N3O3S

B

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
In aq. phosphate buffer; acetonitrile for 1h; Kinetics; Quantum yield; UV-irradiation;
C86H84Cl2N4O8PS2(1+)

C86H84Cl2N4O8PS2(1+)

A

C67H59N3O4P(1+)

C67H59N3O4P(1+)

B

chlorambucil
305-03-3

chlorambucil

Conditions
ConditionsYield
With GLUTATHIONE at 37℃; for 6h;
chlorambucil
305-03-3

chlorambucil

C28H36Cl4N2O3

C28H36Cl4N2O3

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; under 760.051 Torr; for 12h;100%
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 12h;94%
propargyl alcohol
107-19-7

propargyl alcohol

chlorambucil
305-03-3

chlorambucil

prop-2-yn-1-yl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

prop-2-yn-1-yl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Cooling with ice; Inert atmosphere;100%
1-O-methyl-2,3,4-tri-O-trimethylsilyl-β-D-glucopyranoside
20771-10-2

1-O-methyl-2,3,4-tri-O-trimethylsilyl-β-D-glucopyranoside

chlorambucil
305-03-3

chlorambucil

4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyric acid (2R,3R,4S,5R,6R)-6-methoxy-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester
187218-13-9

4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyric acid (2R,3R,4S,5R,6R)-6-methoxy-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h;99%
N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

chlorambucil
305-03-3

chlorambucil

N-methyl-N-methoxy 4-(4-(N,N-bis(2-chloroethyl)amino)phenyl) butanamide
1256381-57-3

N-methyl-N-methoxy 4-(4-(N,N-bis(2-chloroethyl)amino)phenyl) butanamide

Conditions
ConditionsYield
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 1.08333h;97%
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 1.08333h;97%
(3aR,4S,7S,7aS)-2-(2-hydroxyethyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3-dione
68297-52-9

(3aR,4S,7S,7aS)-2-(2-hydroxyethyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3-dione

chlorambucil
305-03-3

chlorambucil

C25H30Cl2N2O4

C25H30Cl2N2O4

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 15h; Inert atmosphere;97%
methyl 4,6-O-benzylidene-2-deoxy-2-(3-hydroxypropylamino)-α-D-altropyranoside
231607-29-7

methyl 4,6-O-benzylidene-2-deoxy-2-(3-hydroxypropylamino)-α-D-altropyranoside

chlorambucil
305-03-3

chlorambucil

methyl 4,6-O-benzylidene-2-<3-(4-<4-phenyl>butanoyloxy)propylamino>-2-deoxy-α-D-altropyranoside
231607-31-1

methyl 4,6-O-benzylidene-2-<3-(4-<4-phenyl>butanoyloxy)propylamino>-2-deoxy-α-D-altropyranoside

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;96%
N(ε)-benzoyloxycarbonyl-L-lysine tert-butyl ester hydrochloride
5978-22-3

N(ε)-benzoyloxycarbonyl-L-lysine tert-butyl ester hydrochloride

chlorambucil
305-03-3

chlorambucil

6-benzyloxycarbonylamino-2-(4-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-butyrylamino)-hexanoic acid tert-butyl ester
616883-55-7

6-benzyloxycarbonylamino-2-(4-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-butyrylamino)-hexanoic acid tert-butyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;96%
ethylene glycol
107-21-1

ethylene glycol

chlorambucil
305-03-3

chlorambucil

4-{4-[bis-(2-chloroethyl)amino]phenyl}butyric acid 2-hydroxyethyl ester

4-{4-[bis-(2-chloroethyl)amino]phenyl}butyric acid 2-hydroxyethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 16h;96%
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 48h;70%
3-(bromomethyl)perylene
1160604-36-3

3-(bromomethyl)perylene

chlorambucil
305-03-3

chlorambucil

(perylen-3-yl)methyl 4-(4-(1,5-dichloropentan-3-yl)phenyl)butanoate
1374018-55-9

(perylen-3-yl)methyl 4-(4-(1,5-dichloropentan-3-yl)phenyl)butanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;96%
5-(2-bromoacetyl)-2-hydroxybenzaldehyde
115787-50-3

5-(2-bromoacetyl)-2-hydroxybenzaldehyde

chlorambucil
305-03-3

chlorambucil

C23H25Cl2NO5

C23H25Cl2NO5

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;96%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 6h;
3,6,9,12-tetraoxapentadec-14-yn-1-ol
87450-10-0

3,6,9,12-tetraoxapentadec-14-yn-1-ol

chlorambucil
305-03-3

chlorambucil

C25H37Cl2NO6

C25H37Cl2NO6

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;96%
octanol
111-87-5

octanol

chlorambucil
305-03-3

chlorambucil

CLB-CH2CH2(CH2)5CH3

CLB-CH2CH2(CH2)5CH3

Conditions
ConditionsYield
With toluene-4-sulfonic acid Heating;95.3%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;90%
methyl 4,6-O-benzylidene-2-deoxy-2-(2-hydroxyethylamino)-α-D-altropyranoside
115400-41-4

methyl 4,6-O-benzylidene-2-deoxy-2-(2-hydroxyethylamino)-α-D-altropyranoside

chlorambucil
305-03-3

chlorambucil

methyl 4,6-O-benzylidene-2-<2-(4-<4-phenyl>butanoyloxy)ethylamino>-2-deoxy-α-D-altropyranoside
231607-30-0

methyl 4,6-O-benzylidene-2-<2-(4-<4-phenyl>butanoyloxy)ethylamino>-2-deoxy-α-D-altropyranoside

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;95%
(4'-(2-(2-methoxyethoxy)ethoxy)-4-nitro-[1,1'-biphenyl]-3-yl)methanol

(4'-(2-(2-methoxyethoxy)ethoxy)-4-nitro-[1,1'-biphenyl]-3-yl)methanol

chlorambucil
305-03-3

chlorambucil

(4'-(2-(2-methoxyethoxy)ethoxy)-4-nitro-[1,1'-biphenyl]-3-yl)methyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

(4'-(2-(2-methoxyethoxy)ethoxy)-4-nitro-[1,1'-biphenyl]-3-yl)methyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;95%
Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 13h; Inert atmosphere;95%

Chlorambucil Chemical Properties

Name of Substance: Chlorambucil
CAS Registry Number: 305-03-3
Synonyms: 4-(Bis(2-chloroethyl)amino)benzenebutanoic acid ; 4-(Bis(2-chloroethyl)amino)phenylbutyric acid ; 4-(p-(Bis(2-chloroethyl)amino)phenyl)butyric acid ; 4-14-00-01715 (Beilstein Handbook Reference) ; AI3-26083 ; Ambochlorin ; Amboclorin ; BRN 0999011 ; Benzenebutanoic acid, 4-(bis(2-chloroethyl)amino)- ; Butanoic acid, 4-(bis(2-chloroethyl)amino) benzene ; Butyric acid, 4-(p-(bis(2-chloroethyl)amino)phenyl) ; CB 1348 ; CCRIS 126 ; Cb l348 ; Chloorambucol ; Chlorambucil ; Chlorambucilum ; Chlorambucilum [INN-Latin] ; Chloraminophen ; Chloraminophene ; Chlorbutin ; Chlorbutine ; Chlorbutinum ; Chloroambucil ; Chlorobutin ; Chlorobutine ; Clorambucile ; Clorambucile [DCIT] ; Clorambucilo ; Clorambucilo [INN-Spanish] ; EINECS 206-162-0 ; Ecloril ; Elcoril ; Elcorin ; HSDB 3026 ; Kyselina 4-(N,N-bis-(2-chlorethyl)-p-aminofenyl)maselna ; Kyselina 4-(N,N-bis-(2-chlorethyl)-p-aminofenyl)maselna [Czech] ; Leukeran ; Linfolizin  ; Linfolysin ; Lympholysin ; N,N-Di-2-chloroethyl-gamma-p-aminophenylbutyric acid ; N,N-Di-2-chloroethyl-gamma-para-aminophenyl butyric acid ; NCI-C03485 ; NSC 3088 ; NSC-3088 ; Phenylbuttersaeure-lost ; Phenylbuttersaeure-lost [German] ; Phenylbutyric acid nitrogen mustard ; RCRA waste number U035 ; UNII-18D0SL7309 ; gamma-(p-Bis(2-chloroethyl)aminophenyl)butyric acid ; gamma-(p-Di(2-chloroethyl)aminophenyl)butyric acid ; gamma-(p-bis(2-chloroethyl)aminophenyl)butyricacid ; p-(N,N-Di-2-chlorethylaminophenyl)butyric acid ; p-(N,N-Di-2-chloroethyl)aminophenyl butyric acid ; p-N,N-Di-(beta-chloroethyl)aminophenyl butyric acid ; para-(Di(2-chloroethyl)aminophenyl)butyric acid ; para-N,N-Di(beta-chloroethyl)aminophenyl butyric acid ; Benzenebutanoic acid, 4-(bis(2-chloroethyl)amino)- ; Butyric acid, 4-(p-bis(2-chloroethyl)aminophenyl)- 
IUPAC Name: 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoic acid 
Molecular Weight: 304.21216 [g/mol]
Molecular Formula: C14H19Cl2NO2
XLogP3: 1.7
H-Bond Donor: 1
H-Bond Acceptor: 3
Melting Point: 65-70 °C
Surface Tension: 48.7 dyne/cm
Density: 1.248 g/cm3
Flash Point: 232.1 °C Enthalpy of
Vaporization: 75.94 kJ/mol
Boiling Point: 460.1 °C at 760 mmHg
Vapour Pressure: 2.92E-09 mmHg at 25°C
Following is the molecular structure of Chlorambucil (CAS NO.305-03-3) is:

Chlorambucil Uses

 Chlorambucil (CAS NO.305-03-3) has been mainly used in the treatment of chronic lymphocytic leukemia. It has been used for treating some types of non-Hodgkin lymphoma, Waldenström macroglobulinemia, polycythemia vera, trophoblastic neoplasms, and ovarian carcinoma. Also it has been used as an immunosuppressive drug for various autoimmune and inflammatory conditions, such as nephrotic syndrome. Currenttly ,its use is mainly in chronic lymphocytic leukemia, as it is well tolerated by most patients, though chlorambucil has been largely replaced by fludarabine as first-line treatment in younger patients.

Chlorambucil Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 3mg/kg (3mg/kg) GASTROINTESTINAL: OTHER CHANGES

BLOOD: OTHER CHANGES
Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 201, 1965.
man TDLo oral 3571ug/kg (3.571mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Toxicology, Clinical Toxicology. Vol. 20, Pg. 361, 1983.
monkey LDLo intravenous 3mg/kg (3mg/kg) GASTROINTESTINAL: OTHER CHANGES

BLOOD: OTHER CHANGES
Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 201, 1965.
mouse LD50 intraperitoneal 20mg/kg (20mg/kg)   British UK Patent Application. Vol. #2028335,
mouse LD50 oral 80mg/kg (80mg/kg)   British UK Patent Application. Vol. #2028335,
mouse LD50 subcutaneous 26mg/kg (26mg/kg)   British UK Patent Application. Vol. #2028335,
rat LD50 intracrebral > 400ug/kg (0.4mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 18, Pg. 760, 1966.
rat LD50 intraperitoneal 14mg/kg (14mg/kg)   Biochemical Pharmacology. Vol. 13, Pg. 969, 1964.
rat LD50 oral 76mg/kg (76mg/kg)   Food and Chemical Toxicology. Vol. 22, Pg. 665, 1984.
rat LDLo subcutaneous 32mg/kg (32mg/kg)   European Journal of Cancer. Vol. 13, Pg. 873, 1977.
women TDLo oral 82600ug/kg (82.6mg/kg) LUNGS, THORAX, OR RESPIRATION: FIBROSIS (INTERSTITIAL)

LUNGS, THORAX, OR RESPIRATION: COUGH

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Cancer Vol. 41, Pg. 455, 1978.

Chlorambucil Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 1 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 144.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 9 , 1975,p. 125.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 , 1981,p. 115.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 , 1981,p. 115.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 9 , 1975,p. 125.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.

Chlorambucil Safety Profile

Safty information about Chlorambucil (CAS NO.305-03-3) is:
Confirmed carcinogen producing leukemia. Experimental carcinogenic and neoplastigenic data. Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Human systemic effects by ingestion: convulsions, cough, dyspnea, and interstitial fibrosis. Human reproductive effects by ingestion and possibly other routes: changes in spermatogenesis, menstrual cycle changes or disorders, and teratogenic effects of the fetal urogenital system. Experimental teratogenic and reproductive effects. Human mutation data reported. An anti-neoplastic agent. When heated to decomposition it emits very toxic fumes of Cl and NOx
Hazard Codes:
ToxicT
Risk Statements:
R45:May cause cancer. 
R25 :Toxic if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements:
S53:Avoid exposure - obtain special instructions before use. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: ES7525000
HazardClass: 6.1(b)
PackingGroup: III

Chlorambucil Specification

 Chlorambucil (CAS NO.305-03-3) is a white to pale beige crystalline or granular powder with a slight odor. And it is a chemotherapy drug , also it insoluble in water.It is an alkylating agent.

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