23261

Sigma-Aldrich

Trichloromethyl chloroformate

≥97.0% (GC)

Synonym(s):
di-Phosgene, TCF, Diphosgene
Linear Formula:
ClCOOCCl3
CAS Number:
Molecular Weight:
197.83
Beilstein/REAXYS Number:
970225
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

assay

≥97.0% (GC)

refractive index

n20/D 1.458

bp

20 °C/10 mmHg (lit.)

density

1.639 g/mL at 20 °C

storage temp.

2-8°C

SMILES string

ClC(=O)OC(Cl)(Cl)Cl

InChI

1S/C2Cl4O2/c3-1(7)8-2(4,5)6

InChI key

HCUYBXPSSCRKRF-UHFFFAOYSA-N

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Application

Reactant for preparation of:
  • Cyclic carbamimidates using a monophosphine gold(i) catalyst
  • N-Alkenyl and cycloalkyl carbamates as dual acting histamine H3 and H4 receptor ligands
  • Prostate-specific membrane antigen-targeted anticancer prodrugs
  • Potential west nile virus protease inhibitors
  • Antibody-drug conjugates (ADCs)
  • Erythromycin A derivatives
Trichloromethyl chloroformate (TCF) is an effective alternative to phosgene. It can react with amines, amino acids and amino alcohols to give the corresponding isocyanates, isocyanato acid chlorides and isocyanato chloroformates.
TCF can also be used:
  • To synthesize N-carboxy α-amino acid anhydrides.
  • As an acylating agent to synthesize oxazolidinones from α-amino alcohols.
  • As a dehydrating agent to synthesize aromatic diisocyanides in the presence of triethylamine.

Packaging

10, 50 mL in glass bottle

Other Notes

Easy to handle substitute for phosgene; In-situ charcoal-catalyzed decomposition to phosgene and reaction with amino acids to N-carboxy anhydrides

Pictograms

CorrosionSkull and crossbones

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3277 8(6.1) / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Trichloromethyl chloroformate. Reaction with amines, amino acids, and amino alcohols.
Kurita K, et al.
The Journal of Organic Chemistry, 41(11), 2070-2071 (1976)
L.N. Pridgen et al.
The Journal of Organic Chemistry, 54, 3231-3231 (1989)
Topics in Inorganic and General Chemistry, 24, 535-541 (1996)
Synthesis of some aromatic diisocyanides with trichloromethyl chloroformate.
Efraty A, et al.
The Journal of Organic Chemistry, 45(20), 4059-4061 (1980)
K. Kunita et al.
Organic Syntheses, 59, 195-195 (1980)

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