cycl-isopropylidene malonate
2-(4-(N,N-bis(2-chloroethyl)amino)phenyl)acetaldehyde
chlorambucil
Conditions | Yield |
---|---|
With formic acid; triethylamine at 50 - 95℃; for 5h; Temperature; | 76.9% |
chlorambucil
Conditions | Yield |
---|---|
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
chlorambucil
Conditions | Yield |
---|---|
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; |
chlorambucil
Conditions | Yield |
---|---|
With water; sodium hydroxide In water for 12h; Reflux; | 41% |
Conditions | Yield |
---|---|
With acetic acid Erwaermen des Reaktionsprodukts mit POCl3 in Benzol und Erhitzen des erhaltenen Esters mit konz. wss. HCl; |
methyl 4-(4-aminophenyl)butanoate
chlorambucil
Conditions | Yield |
---|---|
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
chlorambucil
Conditions | Yield |
---|---|
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
chlorambucil
Conditions | Yield |
---|---|
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
chlorambucil
Conditions | Yield |
---|---|
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
chlorambucil
Conditions | Yield |
---|---|
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
chlorambucil
Conditions | Yield |
---|---|
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
chlorambucil
Conditions | Yield |
---|---|
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
B
chlorambucil
Conditions | Yield |
---|---|
In acetonitrile Irradiation; |
(E)-2-nitro-5-(4-((tetrahydro-2H-pyran-2-yl)oxy)styryl)benzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
chlorambucil
Conditions | Yield |
---|---|
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
chlorambucil
Conditions | Yield |
---|---|
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
B
chlorambucil
Conditions | Yield |
---|---|
Irradiation; |
(E)-5-(4-hydroxystyryl)-2-nitrobenzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
chlorambucil
Conditions | Yield |
---|---|
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
B
chlorambucil
Conditions | Yield |
---|---|
Irradiation; |
(E)-2-(4-(3-(((4-(4-(bis(2-chloroethyl)amino)phenyl)butanoyl)oxy)methyl)-4-nitrostyryl)phenoxy)acetic acid
B
chlorambucil
Conditions | Yield |
---|---|
Irradiation; |
chlorambucil
Conditions | Yield |
---|---|
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
B
chlorambucil
Conditions | Yield |
---|---|
Irradiation; |
B
chlorambucil
Conditions | Yield |
---|---|
Irradiation; |
(E)-2-nitro-5-(4-(2-oxoethoxy)styryl)benzyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
B
chlorambucil
Conditions | Yield |
---|---|
Irradiation; |
(benzo[a]acridin-12-yl)methyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate
chlorambucil
Conditions | Yield |
---|---|
In water; acetonitrile UV-irradiation; |
Conditions | Yield |
---|---|
With water at 20℃; for 0.166667h; UV-irradiation; |
Conditions | Yield |
---|---|
In methanol; water Kinetics; Quantum yield; UV-irradiation; |
Conditions | Yield |
---|---|
In water; acetonitrile for 1h; UV-irradiation; |
Conditions | Yield |
---|---|
In aq. phosphate buffer; acetonitrile for 1h; Kinetics; Quantum yield; UV-irradiation; |
Conditions | Yield |
---|---|
With GLUTATHIONE at 37℃; for 6h; |
chlorambucil
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; under 760.051 Torr; for 12h; | 100% |
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 12h; | 94% |
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; | 99% |
N,O-dimethylhydroxylamine*hydrochloride
chlorambucil
N-methyl-N-methoxy 4-(4-(N,N-bis(2-chloroethyl)amino)phenyl) butanamide
Conditions | Yield |
---|---|
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
chlorambucil
Conditions | Yield |
---|---|
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
chlorambucil
methyl 4,6-O-benzylidene-2-<3-(4-<4-phenyl>butanoyloxy)propylamino>-2-deoxy-α-D-altropyranoside
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; | 96% |
N(ε)-benzoyloxycarbonyl-L-lysine tert-butyl ester hydrochloride
chlorambucil
6-benzyloxycarbonylamino-2-(4-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-butyrylamino)-hexanoic acid tert-butyl ester
Conditions | Yield |
---|---|
With 4-methyl-morpholine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; | 96% |
Conditions | Yield |
---|---|
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
chlorambucil
(perylen-3-yl)methyl 4-(4-(1,5-dichloropentan-3-yl)phenyl)butanoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; | 96% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 96% |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 6h; |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
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
chlorambucil
methyl 4,6-O-benzylidene-2-<2-(4-<4-phenyl>butanoyloxy)ethylamino>-2-deoxy-α-D-altropyranoside
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; | 95% |
chlorambucil
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 95% |
tetra-acetyl glucosamine
chlorambucil
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 13h; Inert atmosphere; | 95% |
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 (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.
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. |
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.
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:
T
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 (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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