23181

Sigma-Aldrich

Chloromethyl chloroformate

≥98.0% (GC)

Linear Formula:
ClCOOCH2Cl
CAS Number:
Molecular Weight:
128.94
Beilstein/REAXYS Number:
506426
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

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

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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

T

Risk Statement

23-34

Safety Statement

26-36/37/39-45

RIDADR

UN 2745 8(6.1) / PGII

WGK Germany

WGK 3

Flash Point(F)

203.0 °F - closed cup

Flash Point(C)

95 °C - closed cup

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...
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...
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...
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...

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