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23181

Sigma-Aldrich

Chloromethyl chloroformate

≥98.0% (GC)

Linear Formula:
ClCOOCH2Cl
CAS Number:
Molecular Weight:
128.94
Beilstein:
506426
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥98.0% (GC)

refractive index

n20/D 1.428

bp

107-108 °C (lit.)

density

1.450 g/mL at 20 °C

storage temp.

2-8°C

SMILES string

ClCOC(Cl)=O

InChI

1S/C2H2Cl2O2/c3-1-6-2(4)5/h1H2

InChI key

JYWJULGYGOLCGW-UHFFFAOYSA-N

Related Categories

Application

Chloromethyl chloroformate was used as key reactant in the synthesis of:
  • novel aminocarbonyloxymethyl esters of diclofenac and flufenamic acid
  • highly water-soluble monomethoxypoly(ethyleneglycol) prodrugs of cyclosporin A
  • series of 3-acyloxymethyloxycarbonyl-1-aryl-3-methyltriazenes

Packaging

10, 50 mL in glass bottle

Pictograms

CorrosionSkull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Inhalation - Skin Corr. 1B

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK Germany

WGK 3

Flash Point(F)

203.0 °F - closed cup

Flash Point(C)

95 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Lina Ribeiro et al.
Archiv der Pharmazie, 340(1), 32-40 (2007-01-09)
Aminocarbonyloxymethyl ester prodrugs are known to undergo rearrangement in aqueous solutions to form the corresponding N-acylamine side product via an O-->N intramolecular acyl transfer from the carbamate conjugate base. Novel aminocarbonyloxymethyl esters of diclofenac and flufenamic acid containing amino acid...
Hoon Cho et al.
Archives of pharmacal research, 27(6), 662-669 (2004-07-31)
The highly water-soluble monomethoxypoly(ethyleneglycol) (mPEG) prodrugs of cyclosporin A (CsA) were synthesized. These prodrugs were prepared by initially preparing intermediate in the form of carbonate at the 3'-positions of CsA with chloromethyl chloroformate, in the presence of a base to...
Keivan Sadrerafi et al.
Drug design, development and therapy, 12, 987-995 (2018-05-08)
Our previous study indicated that carborane containing small-molecule 1-(hydroxymethyl)-7-(4'-(trans-3″-(3'″-pyridyl)acrylamido)butyl)-1,7-dicarbadodecaborane (hm-MC4-PPEA), was a potent inhibitor of nicotinamide phosphoribosyltransferase (Nampt). Nampt has been shown to be upregulated in most cancers and is a promising target for the treatment of many different types...
E Carvalho et al.
Bioorganic & medicinal chemistry, 8(7), 1719-1725 (2000-09-08)
A series of 3-acyloxymethyloxycarbonyl-1-aryl-3-methyltriazenes 5 was synthesised by the sequential reaction of 1-aryl-3-methyltriazenes with (i) chloromethyl chloroformate, (ii) NaI in dry acetone, and (iii) either the silver carboxylate or the carboxylic acids in the presence of silver carbonate. The hydrolysis...

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