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1-Chloroethyl chloroformate

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1-Chloroethyl chloroformate Basic information

Product Name:
1-Chloroethyl chloroformate
Synonyms:
  • 1-Chloroethyl carbonochloridoate
  • a-Chloroethoxycarbonyl chloride
  • 1-CHLOROETHYL CHLOROFORMATE, 97+%
  • 1-Chloroethyl chloroformate,Carbonochloridic acid
  • 1-Chlotoethyl chloroformate
  • Chloroethyl 1-chloroformate
  • 1 - chlorine ethyl chloride acid es
  • RELU-012
CAS:
50893-53-3
MF:
C3H4Cl2O2
MW:
142.97
EINECS:
256-834-2
Product Categories:
  • Acid Halides
  • Building Blocks
  • CHLOROFORMATES
  • Carbonyl Compounds
  • Chemical Synthesis
  • Organic Building Blocks
  • 50893-53-3
Mol File:
50893-53-3.mol
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1-Chloroethyl chloroformate Chemical Properties

Melting point:
-65°C
Boiling point:
118-119 °C (lit.)
Density 
1.325 g/mL at 25 °C (lit.)
vapor pressure 
3.25 psi ( 20 °C)
refractive index 
n20/D 1.422(lit.)
Flash point:
105 °F
storage temp. 
2-8°C
solubility 
Miscible with most organic solvents.
form 
Liquid
color 
Clear colorless
Sensitive 
Moisture Sensitive
BRN 
1747601
Stability:
Hygroscopic, Moisture Sensitive
InChIKey
QOPVNWQGBQYBBP-UHFFFAOYSA-N
CAS DataBase Reference
50893-53-3(CAS DataBase Reference)
NIST Chemistry Reference
«ALPHA»-chloroethyl chloroformate(50893-53-3)
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Safety Information

Hazard Codes 
T
Risk Statements 
10-22-23-34
Safety Statements 
26-36/37/39-45
RIDADR 
UN 2742 6.1/PG 2
WGK Germany 
3
10-19-21
TSCA 
No
HazardClass 
6.1
PackingGroup 
II
HS Code 
29159000

MSDS

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1-Chloroethyl chloroformate Usage And Synthesis

Chemical Properties

Clear and colorless liquid

Uses

Reagent for the selective N-dealkylation of tertiary amines in high yields.

Uses

1-Chloroethyl chloroformate was used:

  • for N-demethylation reaction during determination of multiple drugs of abuse in biological fluids using capillary electrophoresis with native fluorescence and laser-induced fluorescence detection
  • as catalyst in chemoselective desilylation of silyl-protected alcohols
  • as reagent in N-demethylation of tertiary amines to produce drug metabolite reference material for forensic toxicological applications
  • as reagent to cleave benzhydryl groups from amines

Preparation

1-Chloroethyl chloroformate is obtained by stirring phosgene and acetaldehyde in the presence of benzyltributylammonium chloride, followed by distillation (96% yield).

Reactivity Profile

1-chloroethyl chloroformate was found to be the potential reagent of choice for the N-demethylation of tertiary amines. The reaction was performed by refluxing in dry 1,2-dichloroethane under nitrogen, and the carbamate intermediate was hydrolysed by treatment with methanol[1].

The debenzylation conditions were mediated by 1-chloroethyl chloroformate (green), which gave the expected secondary amine 3 (blue) an excellent yield. The debenzylation proceeds presumably via a carbamate intermediate following the reaction of the starting material 6 with 1-chloroethyl chloroformate and loss of benzyl chloride. Subsequent decarboxylation, promoted by excess methanol and reflux conditions, produced the desired secondary amine 3.

Synthesis

An initiator solution was formed by dissolving 0.33 gram of 2,2'-azobis(2-methylpropanenitrile) in 61 grams of ethyl chloroformate. The initiator solution was charged to the syringe. The flask was charged with 590 grams of ethyl chloroformate. The flask was then heated to obtain close to maximum reflux without flooding. The syringe pump was set to feed approximately 5 millilitres of the initiator solution per hour. The introduction of molecular chlorine gas through the first inlet at 0.47 gram per minute was then begun. During the reaction, the condenser functioned as a total reflux condenser. The chlorine introduction was terminated twelve hours later, and the reaction mixture was allowed to cool. The final reaction product weighed 806 grams. Gas chromatographic analysis of the reaction product showed it to contain 18.8 area percent of ethyl chloroformate, 45.4 area percent of 1-chloroethyl chloroformate, 34.7 area percent of 2-chloroethyl chloroformate, and 1.06 area percent of dichlorinated ethyl chloroformate.

References

[1] Anna Pelander, Tapio A. Hase, Ilkka Ojanper? . “Preparation of N-demethylated drug metabolites for analytical purposes using 1-chloroethyl chloroformate.” Forensic science international 85 3 (1997): Pages 193-198.
[2] Katrina A Badiola. “Efficient Synthesis and Anti-Tubercular Activity of a Series of Spirocycles: An Exercise in Open Science.” PLoS ONE (2014): e111782.

1-Chloroethyl chloroformate Preparation Products And Raw materials

Preparation Products

1-Chloroethyl chloroformateSupplier

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