formaldehyd
bis-(2-chloroethyl)amine hydrochloride
mechlorethamine hydrochloride
Conditions | Yield |
---|---|
With formic acid at 100 - 120℃; for 3.33333h; | 100% |
With formic acid In water at 100 - 120℃; for 3.33333h; Heating / reflux; | 100% |
With formic acid In water at 100 - 120℃; for 3.33333h; | 100% |
With formic acid In water 1a.) 100 deg C, 3 h, 1b.) 120 deg C, 20 min; Yield given; |
2-[2-hydroxyethyl(methyl)amino]ethanol hydrochloride
mechlorethamine hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride In chloroform for 2h; Chlorination; Heating; | 99% |
formaldehyd
formic acid
bis-(2-chloroethyl)amine hydrochloride
mechlorethamine hydrochloride
Conditions | Yield |
---|---|
In water at 100℃; for 3h; Reflux; | 99% |
Conditions | Yield |
---|---|
With thionyl chloride In chloroform at 20℃; for 2h; | 96% |
With thionyl chloride In dichloromethane at 0 - 20℃; for 24h; | 92% |
With thionyl chloride In dichloromethane at 20℃; for 48h; Cooling with ice; | 85% |
formic acid
bis-(2-chloroethyl)amine hydrochloride
mechlorethamine hydrochloride
Conditions | Yield |
---|---|
In water at 100 - 120℃; | 92% |
mechlorethamine hydrochloride
p-methoxybenzylnitrile
4-(4-methoxyphenyl)-1-methylpiperidine-4-carbonitrile
Conditions | Yield |
---|---|
With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 60℃; for 24h; | 100% |
With tetra(n-butyl)ammonium hydrogensulfate In sodium hydroxide | 20% |
mechlorethamine hydrochloride
1-methyl-4-(4-butoxybenzenesulfonyl)piperidine-4-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In acetone for 16h; Heating; | 98% |
3-methoxy-4-hydroxybenzonitrile
mechlorethamine hydrochloride
1,5-bis(4-cyano-2-methoxyphenoxy)-N-methyl-3-azapentane
Conditions | Yield |
---|---|
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 115℃; for 3h; | 98% |
potassium tetrachloroplatinate(II)
mechlorethamine hydrochloride
Conditions | Yield |
---|---|
In water aq. soln. mechlorethamine hydrochloride and K2PtCl4 was heated at 50-60°C for 3 h; soln. was left at room temp. for 2 days, ppt. was filtered off, washed with EtOH and air-dried; elem. anal.; | 95% |
mechlorethamine hydrochloride
p-chlorobenzyl cyanide
4-(4-chlorophenyl)-1-methylpiperidine-4-carbonitrile
Conditions | Yield |
---|---|
With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 60℃; for 24h; | 92% |
With tetra(n-butyl)ammonium hydrogensulfate In sodium hydroxide |
4-Bromophenylacetonitrile
mechlorethamine hydrochloride
4-(4-bromophenyl)-1-methylpiperidine-4-carbonitrile
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20 - 60℃; for 19h; | 90% |
mechlorethamine hydrochloride
thiourea
bis-(2-carbamimidoylmercapto-ethyl)-methyl-amine; trihydrochloride
Conditions | Yield |
---|---|
In ethanol for 5h; Condensation; Heating; | 88% |
In ethanol at 80℃; for 5h; | 65% |
In ethanol Reflux; |
Conditions | Yield |
---|---|
With hydrazine hydrate | 87% |
Conditions | Yield |
---|---|
With hydrazine hydrate at 50℃; for 2h; | A 2% B 87% |
4-fluorophenylacetonitrile
mechlorethamine hydrochloride
4-(4-fluorophenyl)-1-methylpiperidine-4-carbonitrile
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0 - 60℃; for 24h; | 82% |
With sodium hydride In DMF (N,N-dimethyl-formamide) at 60℃; for 24h; | 82% |
With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 60℃; for 24h; | 82% |
With tetra(n-butyl)ammonium hydrogensulfate In sodium hydroxide |
mechlorethamine hydrochloride
3,4-dichloro-benzeneacetonitrile
4-(3,4-dichlorophenyl)-1-methylpiperidine-4-carbonitrile
Conditions | Yield |
---|---|
With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 60℃; for 24h; | 82% |
With sodium hydroxide; cetyltributylphosphonium bromide at 100℃; for 1h; | |
With sodium hydroxide; tributyl pentadecylphosphonium bromide In water at 100℃; for 1h; |
mechlorethamine hydrochloride
4-cyanophenol
4,4'-[1,5-(N-methyl-3-azapentanediylbis(oxy))]bisbenzonitrile
Conditions | Yield |
---|---|
With potassium carbonate In various solvent(s) at 130℃; for 16h; | 82% |
mechlorethamine hydrochloride
6-bromo-2,3-dihydro-1H-indole-2-one
6-bromo-1'-methyl-spiro [indole-3,4'-piperidin]-2 (1H)-one
Conditions | Yield |
---|---|
Stage #1: 6-bromo-2,3-dihydro-1H-indole-2-one With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: mechlorethamine hydrochloride In tetrahydrofuran at -78 - 20℃; for 48.5h; | 82% |
Stage #1: 6-bromo-2,3-dihydro-1H-indole-2-one With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: mechlorethamine hydrochloride In tetrahydrofuran at -78 - 20℃; | 31% |
mechlorethamine hydrochloride
[4-(4-chlorophenoxy)benzenesulfonyl]acetic acid ethyl ester
4-[4-(4-chlorophenoxy)benzenesulfonyl]-1-methylpiperidine-4-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In acetone for 16h; Heating; | 81% |
5-bromo-2-indolin-2-one
mechlorethamine hydrochloride
5-bromo-1'-methyl-spiro[indoline-3,4'-piperidine]-2-one
Conditions | Yield |
---|---|
Stage #1: 5-bromo-2-indolin-2-one With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: mechlorethamine hydrochloride In tetrahydrofuran at -78 - 20℃; for 48.5h; | 78% |
diphenyl(2-hydroxyphenylmethyl)phosphine oxide
mechlorethamine hydrochloride
methylamine
Conditions | Yield |
---|---|
With caesium carbonate In 1,4-dioxane for 14h; Heating; | 76% |
2-(4-methoxybenzenesulfonyl)acetic acid ethyl ester
mechlorethamine hydrochloride
1-methyl-4-(4-methoxy-benzenesulfonyl)-piperidine-4-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In acetone for 16h; Heating; | 75% |
3,5-dimethoxy-4-hydroxybenzonitrile
mechlorethamine hydrochloride
1,5-bis(4-cyano-2,6-dimethoxyphenoxy)-N-methyl-3-azapentane
Conditions | Yield |
---|---|
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 1.5h; | 74% |
di-isopropylphosphine
mechlorethamine hydrochloride
Conditions | Yield |
---|---|
Stage #1: di-isopropylphosphine With n-butyllithium In tetrahydrofuran for 1h; Schlenk technique; Reflux; Stage #2: mechlorethamine hydrochloride With n-butyllithium In tetrahydrofuran Schlenk technique; Reflux; | 73% |
Stage #1: di-isopropylphosphine With n-butyllithium In diethyl ether; hexane at -78℃; for 4h; Schlenk technique; Reflux; Inert atmosphere; Stage #2: mechlorethamine hydrochloride With n-butyllithium In diethyl ether; hexane at -78℃; for 2h; Schlenk technique; Inert atmosphere; Reflux; |
2-hydroxybromobenzene
mechlorethamine hydrochloride
N-methylbis<2-(o-bromophenoxy)ethyl>amine
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 3h; Heating; | 72% |
3-nitro-(4-piperidin-1-yl)aniline
mechlorethamine hydrochloride
1-methyl-4-(3-nitro-4-piperidin-1-yl-phenyl)-piperazine
Conditions | Yield |
---|---|
With potassium carbonate In ethanol for 48h; | 71% |
lithium di-tert-butylphosphide
mechlorethamine hydrochloride
bis(2-(di-t-butylphosphino)ethyl)methylamine
Conditions | Yield |
---|---|
Stage #1: mechlorethamine hydrochloride With n-butyllithium In diethyl ether; hexane at -78 - 20℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: lithium di-tert-butylphosphide In diethyl ether; hexane at -78 - 60℃; Inert atmosphere; Schlenk technique; Reflux; | 69% |
Stage #1: mechlorethamine hydrochloride With n-butyllithium In tetrahydrofuran; hexane at 0℃; Inert atmosphere; Schlenk technique; Stage #2: lithium di-tert-butylphosphide In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Schlenk technique; | 3.8 g |
mechlorethamine hydrochloride
diphenylphosphane
N-methyl (bis(2-(diphenylphosphanyl)ethyl))amine
Conditions | Yield |
---|---|
Stage #1: diphenylphosphane With n-butyllithium In tetrahydrofuran; hexane Stage #2: mechlorethamine hydrochloride With n-butyllithium In tetrahydrofuran | 68% |
Stage #1: diphenylphosphane With n-butyllithium In diethyl ether; hexane at -78℃; for 4h; Inert atmosphere; Schlenk technique; Reflux; Stage #2: mechlorethamine hydrochloride In diethyl ether; hexane at -78℃; Inert atmosphere; Schlenk technique; Reflux; | 0.6538 g |
mechlorethamine hydrochloride
Conditions | Yield |
---|---|
With sodium hydroxide; sodium iodide; sodium hydrogencarbonate In water; acetonitrile | 67% |
mechlorethamine hydrochloride
ethyl 2-oxindoline-5-carboxylate
ethyl 1'-methyl-2-oxospiro[indoline-3,4'-piperidine]-5-carboxylate
Conditions | Yield |
---|---|
Stage #1: ethyl 2-oxindoline-5-carboxylate With sodium hydride In N,N-dimethyl-formamide for 0.166667h; cooling; Stage #2: mechlorethamine hydrochloride In N,N-dimethyl-formamide for 5.16667h; Further stages.; | 65% |
Product Name: Bis(2-chloroethyl)methylaminehydrochloride (CAS NO.55-86-7)
IUPAC Name: 2-chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride
CAS: 55-86-7
Molecular Formula: C5H12Cl3N
Molecular Weight: 192.51
EINECS: 200-246-0
Melting point: 108-111 °C(lit.)
Storage temp.: -20°C
Merck: 13,5798
Enthalpy of Vaporization: 34.9 kJ/mol
Vapour Pressure: 23.9 mmHg at 25°C
Product Categories: Aliphatics; Amines
Bis(2-chloroethyl)methylaminehydrochloride (CAS NO.55-86-7) is mainly prototype anticancer chemotherapeutic drug which is formerly used as a war gas.
1. | sln-dmg-orl 5 mmol/L | MUREAV Mutation Research. 95 (1982),237. | ||
2. | dni-hmn:hla 1 µmol/L | MUREAV Mutation Research. 92 (1982),427. | ||
3. | msc-mus:lym 20 µg/L | FCTOD7 Food and Chemical Toxicology. 23 (1985),115. | ||
4. | ivn-hmn TDLo:400 µg/kg:CNS,BLD | CLPTAT Clinical Pharmacology and Therapeutics. 6 (1965),50. | ||
5. | orl-rat LD50:10 mg/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 91 (1947),224. | ||
6. | scu-rat LD50:1900 µg/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 91 (1947),224. | ||
7. | ivn-rat LD50:1100 µg/kg | MEIEDD Merck Index. 10 (1983),822. | ||
8. | par-rat LD50:1700 µg/kg | RRCRBU Recent Results in Cancer Research. 52 (1975),76. | ||
9. | orl-mus LD50:20 mg/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 91 (1947),224. | ||
10. | ipr-mus LD50:2900 µg/kg | NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. 62 (1966),96. | ||
NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2A IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man 7 (1987),p. 269.(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. 193.(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.
Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Deadly poison by ingestion, intravenous, subcutaneous, intraperitoneal, and parenteral routes. Experimental teratogenic and reproductive effects. Human systemic effects by intravenous route: nausea or vomiting, reduction in the number of white blood cells and blood platelets. Other experimental reproductive effects. Human mutation data reported.
Safety Information of Bis(2-chloroethyl)methylaminehydrochloride (CAS NO.55-86-7):
Hazard Codes: T+
Risk Statements: 45-46-28-34-42/43
R45:May cause cancer.
R46:May cause heritable genetic damage.
R28:Very toxic if swallowed.
R34:Causes burns.
R42/43:May cause sensitization by inhalation and skin contact.
Safety Statements: 53-36/37/39-45
S53:Avoid exposure - obtain special instructions before use. |
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
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 2
WGK Germany: 3
HazardClass: 6.1(a)
PackingGroup: II
Bis(2-chloroethyl)methylaminehydrochloride (CAS NO.55-86-7) is also named as Chlormethine hydrochloride ; 1,5-Dichloro-3-methyl-3-azapentanehydrochloride ; 2-Chloro-n-(2-chloroethyl)-n-methylethanaminehydrochlroide ; 2-Chloro-n-(2-chloroethyl)-n-methyl-ethanaminhydrochloride ; Antimit ; Azotoyperite ; Beta,beta'-dichlorodiethyl-n-methylaminehydrochloride ; C6866 ; Caryolysine and so on. Bis(2-Chloroethyl)Methylamine Hydrochloride is usually white to off-white crystals or powder with a fishy odor.
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