1943-83-5

Basic information

• Product Name: 2-Chloroethyl isocyanate
• Synonyms: 2-CHLOROETHYL ISOCYANATE;1-CHLORO-2-ISOCYANATO-ETHANE;ISOCYANIC ACID 2-CHLOROETHYL ESTER;1-chloro-2-isocyanato-ethan;2-chlorethylisokyanat;nsc87418;2-CHLOROETHYL ISOCYANATE, LOW HCL, 97%;2-Chloroethyl isocyanate 97%
• CAS NO: 1943-83-5
• Molecular Formula: C₃H₄ClNO
• Molecular Weight: 105.52
• EINECS: 217-734-4
• Product Categories: Organics;Aliphatics;Isocyanates;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Pyrrolidines ,Pyrroles
• Mol File: 1943-83-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 144-145 °C
• Boiling Point: 141-142 °C(lit.)
• Flash Point: 135 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.237 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.88mmHg at 25°C
• Refractive Index: n20/D 1.447(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: reacts
• Sensitive: Lachrymatory
• Stability: Stable, but moisture sensitive. Combustible. Incompatible with water, moisture, strong oxidizing agents, strong bases, acids, al
• BRN: 1071429
• CAS DataBase Reference: 2-Chloroethyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloroethyl isocyanate(1943-83-5)
• EPA Substance Registry System: 2-Chloroethyl isocyanate(1943-83-5)

Safety Data

• Hazard Codes: Xn,T,C
• Statements: 20/21/22-36/37/38-42-34-23/24/25
• Safety Statements: 26-36-45-38-36/37/39-28A-23-7/9
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: NQ8450000
• F: 10-19
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 1943-83-5(Hazardous Substances Data)

Usage

Chemical Properties

liquid

Uses

2-Chloroethyl isocyanate may be used in the synthesis of:8-carbamoyl-3-(2-chloroethyl)imidazo[5,1-d]-l,2,3,5-tetrazin-4(3H)-one1-(2-chloroethyl)-3-(2-hydroxyethyl) urea3-substituted 1-(2-chloroethyl)-3-β-glycosylureas1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea (CCNU)(2-chloroethyl)-4-acetoxybenzyl ester

Synthesis Reference(s)

The Journal of Organic Chemistry, 32, p. 1508, 1967 DOI: 10.1021/jo01280a045

InChI:InChI=1/C3H4ClNO/c4-1-2-5-3-6/h1-2H2

Synthetic route

C3H4ClN3O (98384-97-5) → 2-chloroethyl isothiocyanate (1943-83-5)

Conditions	Yield
Heating;	100%

2-chloropropionyl chloride (625-36-5) → 2-chloroethyl isothiocyanate (1943-83-5)

Conditions	Yield
With sodium azide In benzene for 5h; Heating;	52%

phosgene (75-44-5) + 2-chloroethanamine hydrochloride (870-24-6) → 2-chloroethyl isothiocyanate (1943-83-5)

Conditions	Yield
With 1,2,3-trichlorobenzene at 140℃;

ethyleneimine (151-56-4) + phosgene (75-44-5) → 2-chloroethyl isothiocyanate (1943-83-5)

Conditions	Yield
(i) CCl4, (ii) (heating); Multistep reaction;
With triethylamine In diethyl ether

dimethylenecyclourethane (497-25-6) → 2-chloroethyl isothiocyanate (1943-83-5)

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride

<2-chloro-ethyl>-uretane → 2-chloroethyl isothiocyanate (1943-83-5)

Conditions	Yield
With phosphorus trichloride zuletzt auf dem Dampfbad;

<2-hydroxy-ethyl>-urethane → 2-chloroethyl isothiocyanate (1943-83-5)

Conditions	Yield
With phosphorus trichloride zuletzt auf dem Dampfbad;

ethyl N-(2-chloroethyl)carbamate (6329-26-6) + phosphorus pentachloride (10026-13-8, 874483-75-7) → 2-chloroethyl isothiocyanate (1943-83-5)

carbon dioxide (124-38-9) + 2-chloroethanamine hydrochloride (870-24-6) → 2-chloroethyl isothiocyanate (1943-83-5)

Conditions	Yield
Stage #1: carbon dioxide; 2-chloroethanamine hydrochloride With 1,1,1,3,3,3-hexamethyl-disilazane In toluene at 80 - 90℃; for 3h; Stage #2: at 200℃; Further stages.;

chloropropionic acid (107-94-8) → 2-chloroethyl isothiocyanate (1943-83-5)

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine In toluene at 20 - 80℃; for 1.25h; Inert atmosphere;

2-chloroethyl isothiocyanate (1943-83-5) + aniline (62-53-3) → 1-(2-chloroethyl)-3-phenylurea (7144-13-0)

Conditions	Yield
In dichloromethane at 20℃; for 20h; Inert atmosphere;	100%
In dichloromethane at 25℃; for 24h; Cooling with ice; Inert atmosphere;	99%
In dichloromethane at 0 - 25℃;	99%

2-chloroethyl isothiocyanate (1943-83-5) + Cyclopentamine (1003-03-8) → 1-(2-chloroethyl)-3-cyclopentylurea (13908-08-2)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃;	100%
In acetonitrile at 20℃; for 2h;	34.97%
In chloroform
In water Heating;

4-aminopyridine (504-24-5) + 2-chloroethyl isothiocyanate (1943-83-5) → N-(2-chloroacetyl)-N'-(4-pyridyl)urea (62491-96-7)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃;	100%
In toluene at 0 - 12℃; for 12h;	94%
In toluene at 20℃; for 6h;	87%

2-chloroethyl isothiocyanate (1943-83-5) + 2-carbomethoxyaniline (134-20-3) → methyl 2-<3-(2-chloroethyl)ureido>benzoate (77093-92-6)

Conditions	Yield
for 16h; Ambient temperature;	100%

2-chloroethyl isothiocyanate (1943-83-5) + 3-Iodoaniline (626-01-7) → 1-(2-chloro-ethyl)-3-(3-iodo-phenyl)-urea

Conditions	Yield
In dichloromethane at 0 - 20℃; for 20h;	100%
In dichloromethane at 0 - 20℃; for 20h;	100%
at 20℃;	95%

2-chloroethyl isothiocyanate (1943-83-5) + but-3-yn-1-amine (14044-63-4) → 1-but-3-ynyl-3-(2-chloroethyl)urea (928830-20-0)

Conditions	Yield
In diethyl ether for 0.5h;	100%

2-chloroethyl isothiocyanate (1943-83-5) + tert-butyl (3R,4R)-4-amino-3-(3,4-dichlorophenyl)piperidine-1-carboxylate p-toluenesulfonate (1160260-04-7) → tert-butyl (3R,4R)-4-{[(2-chloroethyl)carbamoyl]amino}-3-(3,4-dichlorophenyl)piperidine-1-carboxylate (1218764-57-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 10 - 35℃; for 4h;	100%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 2-chloroethyl isothiocyanate (1943-83-5) → tert-butyl (3R)-3-{[(2-chloroethyl)carbamoyl]amino}piperidine-1-carboxylate

Conditions	Yield
With triethylamine In dichloromethane for 4.41667h;	100%
With triethylamine In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; for 4h;	81.5%
With triethylamine In dichloromethane for 4.41667h;

2-chloroethyl isothiocyanate (1943-83-5) + 3-aminopropyltriethoxysilane (919-30-2) → (EtO)3Si-CH2CH2CH2-NH-CO-NH-CH2CH2-Cl

Conditions	Yield
In pentane Solvent;	100%
In pentane at -78 - 20℃; for 4.5h;	100%
In ethanol at -78 - 50℃; for 2.5h;	90.8%
In ethanol at -78 - -68℃; for 1.75h;

2-chloroethyl isothiocyanate (1943-83-5) + 2-[2-(2-aminoethoxy)-4-(trifluoromethyl)phenyl]-8-chlorochromen-4-one → 1-(2-chloroethyl)-3-[2-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]ethyl]urea

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 20℃; for 2h;	100%

2-chloroethyl isothiocyanate (1943-83-5) + (S)-3-(4-Amino-phenyl)-2-formylamino-propionic acid (94976-10-0) → Nα-Formyl-4-(N'-2-chloroethylureido)-L-phenylalanine (94976-27-9)

Conditions	Yield
In N,N-dimethyl-formamide at 0 - 5℃; for 4h;	99%

2-chloroethyl isothiocyanate (1943-83-5) + N-methyl-4-amino-2,2,6,6-tetramethylpiperidinyl-1-oxyl (42585-33-1) → C13H25ClN3O2 (97579-77-6)

Conditions	Yield
In diethyl ether at 20℃; for 3h;	99%

2-chloroethyl isothiocyanate (1943-83-5) + 4--2,2,6,6-tetramethylpiperidinoxylamin → C14H27ClN3O3

Conditions	Yield
In diethyl ether at 20℃; for 3h;	99%

2-chloroethyl isothiocyanate (1943-83-5) + p-cyclohexylaniline (6373-50-8) → 4-cyclohexyl-[3-(2-chloroethyl)ureido]benzene (74746-36-4)

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere;	99%
at 20℃;	63%
for 6h; Ambient temperature;
In toluene at 20℃;

2-chloroethyl isothiocyanate (1943-83-5) + 5-acetyl-4-methylthiazole-2-amine (30748-47-1) → 1-(5-acetyl-4-methylthiazol-2-yl)imidazolidin-2-one (1072805-54-9)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 45h; Heating / reflux;	99%
With triethylamine In tetrahydrofuran at 20℃; for 45h; Reflux;	99%

2-chloroethyl isothiocyanate (1943-83-5) + 4-aminophenyl-4-toluenesulfonic acid ester (3899-93-2) → 4-[3-(2-chloroethyl)ureido]phenyl 4-methylbenzenesulfonate (1311946-59-4)

Conditions	Yield
In dichloromethane at 20℃; for 216h; Inert atmosphere; Cooling with ice;	99%

2-chloroethyl isothiocyanate (1943-83-5) + 4-(tert-butyldimethylsilyloxy)phenyl 4-aminobenzenesulfonate (1328953-61-2) → 4-(tert-butyldimethylsilyloxy)phenyl 4-[3-(2-chloroethyl)ureido]benzenesulfonate (1328953-79-2)

Conditions	Yield
With pyridine In acetonitrile at 20℃; for 168h; Inert atmosphere;	99%

2-chloroethyl isothiocyanate (1943-83-5) + diphenylphosphane (829-85-6) → C15H15ClNOP

Conditions	Yield
In neat (no solvent) at 20℃; for 1h; Schlenk technique; Inert atmosphere;	99%

2-chloroethyl isothiocyanate (1943-83-5) + <(methyl-2 amino-2 propyl)-1 dimethyl-2,6 pyridinylidene-4 yl>-2 indanedione-1,3 (95835-40-8) → (chloro-2 ethyl)-1 (<(indanedione-1,3 ylidene-2 yl)-4 dimethyl-2,6 dihydro-1,4 pyridinyl-1>-3 methyl-2 propyl-2)-3 uree (95835-21-5)

Conditions	Yield
In chloroform for 23h; Ambient temperature;	98.1%

pyridin-3-ylamine (462-08-8) + 2-chloroethyl isothiocyanate (1943-83-5) → 1-(2-chloro-ethyl)-3-pyridin-3-yl-urea (13908-58-2)

Conditions	Yield
In toluene at 0 - 20℃; for 5.5h;	98%
In toluene at 0 - 20℃; for 5.5h;	98%
In tetrahydrofuran for 1.5h; Ambient temperature;	81%

2-chloroethyl isothiocyanate (1943-83-5) + 5-amino-3-morpholino-1H-1,2,4-triazole (51420-46-3) → 5-Amino-3-morpholin-4-yl-[1,2,4]triazole-1-carboxylic acid (2-chloro-ethyl)-amide (116986-41-5)

Conditions	Yield
In 1,4-dioxane at 25℃; for 12h;	98%

2-chloroethyl isothiocyanate (1943-83-5) + 4-(aminomethyl)-2,2,6,6-tetramethyl-1-oxy-piperidin-4-yl (56674-44-3) → C13H25ClN3O2 (172325-48-3)

Conditions	Yield
In diethyl ether at 20℃; for 3h;	98%

2-chloroethyl isothiocyanate (1943-83-5) + NN'-Bis-(2-aminoethyl)-NNN'N'-tetramethylhexanediammonium dibromide dihydrochloride (114728-26-6) → NN'-Bis-<2-<3-(2-chloroethyl)ureido>ethyl>-NNN'N'-tetramethyhexanediammonium dibromide (114728-28-8)

Conditions	Yield
With triethylamine In methanol at 0℃; for 1h;	98%

2-chloroethyl isothiocyanate (1943-83-5) + benzenemethanol, 2-[(tetrahydro-2H-pyran-2-yl)oxy]- (130413-06-8) → carbamic acid, (2-chloroethyl)-2-[(tetrahydro-2H-pyran-2-yl)oxy]benzyl ester (267664-74-4)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 48h; Addition;	98%

2-chloroethyl isothiocyanate (1943-83-5) + 3-(benzyloxy)aniline (1484-26-0) → 1-(3-benzyloxy-phenyl)-3-(2-chloro-ethyl)-thiourea (1007864-55-2)

Conditions	Yield
In dichloromethane at 20℃;	98%

2-chloroethyl isothiocyanate (1943-83-5) + 3-(4-methylcyclohexyloxy)benzenamine (1063655-95-7) → C16H23ClN2O2 (1063656-56-3)

Conditions	Yield
In dichloromethane at 20℃;	98%

2-chloroethyl isothiocyanate (1943-83-5) + 6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-amine (51490-15-4) → C14H19ClN2O (1063656-17-6)

Conditions	Yield
In dichloromethane at 20℃;	98%

2-chloroethyl isothiocyanate (1943-83-5) + 4-chloro-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole → N-(2-chloroethyl)-4-chloro-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide

Conditions	Yield
With triethylamine In ethyl acetate at 20℃; for 8h;	97.6%

2-chloroethyl isothiocyanate (1943-83-5) + 1,2-diamino-benzene (95-54-5) → 1,1'-(1,2-phenylene)bis(3-(2-chloroethyl)urea) (13908-65-1)

Conditions	Yield
In tetrahydrofuran; dichloromethane at 0 - 20℃; for 6h;	97%
In chloroform

Upstream product

• 151-56-4 ethyleneimine 
• 75-44-5 phosgene 
• 625-36-5 2-chloropropionyl chloride 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 689-98-5 chloroethylamine 
• 98384-97-5 C₃H₄ClN₃O 
• 124-38-9 carbon dioxide 
• 870-24-6 2-chloroethanamine hydrochloride 
• 6329-26-6 ethyl N-(2-chloroethyl)carbamate 
• 10026-13-8 phosphorus pentachloride 
• 497-25-6 dimethylenecyclourethane 
• 107-94-8 chloropropionic acid 

Downstream Products

• 60984-02-3 N-(4-ethoxy-phenyl)-N'-(2-chloro-ethyl)-urea 
• 13908-40-2 N-(2-chloro-ethyl)-N'-(2,6-dimethyl-phenyl)-urea 
• 13908-02-6 1-(tert-butyl)-3-(2-chloroethyl)urea 
• 33082-80-3 1-(2-chloroethyl)-3-(α,α-dimethylphenethyl)-urea 
• 65536-40-5 N-(2-chloro-ethyl)-N'-(4-methoxy-phenyl)-urea 
• 13908-48-0 N-(4-acetyl-phenyl)-N'-(2-chloro-ethyl)-urea 
• 13908-11-7 N-(2-chloroethyl)-N'-cyclohexylurea 
• 2214-72-4 1,3-bis(2-chloroethyl)urea 
• 24665-93-8 4,5-dihydro-oxazol-2-ylamine 
• 97027-10-6 N-(2-chloro-ethyl)-N'-(4-chloro-[1]naphthyl)-urea 
• 91767-01-0 N-(2-chloro-ethyl)-N'-(4-propionyl-phenyl)-urea 
• 94501-12-9 N-(2-chloro-ethyl)-N'-(3-chloro-benzhydryl)-urea 
• 92194-61-1 N-(2-chloro-ethyl)-N'-[1]naphthylmethyl-urea 
• 77093-92-6 methyl 2-<3-(2-chloroethyl)ureido>benzoate 

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