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3543-75-7

Basic Information
CAS No.: 3543-75-7
Name: Bendamustine hydrochloride
Article Data: 18
Molecular Structure:
Molecular Structure of 3543-75-7 (Bendamustine hydrochloride)
Formula: C16H22Cl3N3O2
Molecular Weight: 394.729
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;
EINECS: 631-540-0
Melting Point: 149-151 °C
Boiling Point: 585.2 °C at 760 mmHg
Flash Point: 307.7 °C
Appearance: pale brown crystals
Hazard Symbols: T,Xn
Risk Codes: 60-61-22-40
Safety: 36-37
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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  • Bendamustine hydrochloride CAS:3543-75-7

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    CAS NO.:3543-75-7

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    Bendamustine hydrochloride 3543-75-7

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Chemistry

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

Uses

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

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.

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 NOx.

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.