ChemicalBook > CAS DataBase List > 1-Chloroethyl chloroformate

1-Chloroethyl chloroformate

Product Name
1-Chloroethyl chloroformate
CAS No.
50893-53-3
Chemical Name
1-Chloroethyl chloroformate
Synonyms
ACE-CL;1-Chloroethyl carbonochloridate;α-Chloroethyl Chloroformate;RELU-012;a-Chloroethoxycarbonyl chloride;1-ChL;1-Chlorethylchlorformiat;Isavuconazole Impurity 36;Isavuconazole Impurity 54;1-Chlorothyl chloroformate
CBNumber
CB5320341
Molecular Formula
C3H4Cl2O2
Formula Weight
142.97
MOL File
50893-53-3.mol
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1-Chloroethyl chloroformate Property

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

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
F 
10-19-21
TSCA 
No
HazardClass 
6.1
PackingGroup 
II
HS Code 
29159000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H226Flammable liquid and vapour

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
301485
Product name
1-Chloroethyl chloroformate
Purity
98%
Packaging
5g
Price
$38.7
Updated
2024/03/01
Sigma-Aldrich
Product number
301485
Product name
1-Chloroethyl chloroformate
Purity
98%
Packaging
25g
Price
$109
Updated
2024/03/01
Alfa Aesar
Product number
L14197
Product name
1-Chloroethyl chloroformate, 98%
Packaging
5g
Price
$27.65
Updated
2024/03/01
Alfa Aesar
Product number
L14197
Product name
1-Chloroethyl chloroformate, 98%
Packaging
25g
Price
$93
Updated
2024/03/01
TRC
Product number
C366060
Product name
α-ChloroethylChloroformate
Packaging
100g
Price
$130
Updated
2021/12/16
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1-Chloroethyl chloroformate Chemical Properties,Usage,Production

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

Raw materials

Preparation Products

N-Boc-Nortropinone Cefpodoxime proxetil
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1-Chloroethyl chloroformate Suppliers

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View Lastest Price from 1-Chloroethyl chloroformate manufacturers

Guangzhou Tosun Pharmaceutical Ltd
Product
1-Chloroethyl chloroformate 50893-53-3
Price
US $0.00-0.00/mg
Min. Order
5mg
Purity
95%+
Supply Ability
1000mg
Release date
2025-02-14
Guangzhou Tosun Pharmaceutical Ltd
Product
Isavuconazole Impurity 54
Price
US $0.00-0.00/mg
Min. Order
5mg
Purity
95%+
Supply Ability
1000mg
Release date
2025-02-14
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
1-Chloroethyl chloroformate 50893-53-3
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-24

50893-53-3, 1-Chloroethyl chloroformateRelated Search:

Benzyl chloroformate Benzyl benzoate Diisononyl phthalate Diethyl azodicarboxylate Urethane Triethyl orthoformate Dimethyl phthalate Diethyl phthalate Ethyl formate POLYURETHANE Isavuconazole Impurity 35 Efinaconazole Impurity 13 (2R,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-2-Methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyraMide Ethyl chloroformate BIS(CHLOROMETHYL)ETHER b-Chloroethyl chloroformate,2-CHLOROETHYL CHLOROFORMATE Polyol benzoate Chloromethyl chloroformate

  • 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
  • 1-Chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane
  • 1-ChL
  • 1-Chlorocarbonyloxy-1-chloroethane
  • α-Chloroethoxycarbonyl Chloride
  • 1-Chloroethyl chloroforMate,99%
  • 1-Chlorothyl chloroformate
  • 1-Chloroethyl chloridocarbonate
  • Carbonochloridic acid, 1-chloroethyl ester
  • 1-CHLOROETHYL CHLOROFORMATE
  • ACE-CL
  • Ethyl chloroforMate-1- chloride
  • 1 - chlorine ethyl chloride acid ester
  • Chloroformic Acid 1-Chloroethyl Ester ACE-Cl
  • CHLOROFORMIC ACID 1-CHLOROETHYL ESTER
  • 1-Chloroethylchloroformate,98%
  • 1-Chloroethyl chloroformate (JCC)
  • 1-CHLOROETHYL CHLOROFORMATE 99%
  • 1-Chloroethyl carbonochloridate
  • 1-Chloroethyl Chlorofomate
  • 1-Chlorethylchlorformiat
  • Isavuconazole Impurity 36
  • 1-Chloroethyl Chloroformate &gt
  • Chloroformic Acid 1-Chloroethyl Ester,>98%
  • α-Chloroethyl Chloroformate
  • Isavuconazole Impurity 54
  • 1-Chloroethyl chloroformate (1-CECF)
  • 1-Chloroethyl Chloroformate, ≥ 98.0%
  • 50893-53-3
  • 50593-53-3
  • 50893-53-4
  • CH3CHClOCOCl
  • Carbonyl Compounds
  • Building Blocks
  • Synthetic Reagents
  • Protecting and Derivatizing Reagents
  • Protection and Derivatization
  • Others
  • Organic Building Blocks
  • Acid Halides
  • Acid Halides
  • Building Blocks
  • Carbonyl Compounds
  • Chemical Synthesis
  • Organic Building Blocks
  • CHLOROFORMATES
  • 50893-53-3