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23261

Sigma-Aldrich

Trichloromethyl chloroformate

≥97.0% (GC)

Synonym(s):

TCF, Diphosgene, di-Phosgene

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About This Item

Linear Formula:
ClCOOCCl3
CAS Number:
Molecular Weight:
197.83
Beilstein:
970225
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

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

functional group

chloro

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.

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

Skull and crossbonesCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Skin Corr. 1B

Storage Class Code

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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K. Kunita et al.
Organic Syntheses, 59, 195-195 (1980)
R. Katakai et al.
The Journal of Organic Chemistry, 50, 715-715 (1985)
Synthesis of some aromatic diisocyanides with trichloromethyl chloroformate.
Efraty A, et al.
The Journal of Organic Chemistry, 45(20), 4059-4061 (1980)
An improved rapid method for the synthesis of N-carboxy. alpha.-amino acid anhydrides using trichloromethyl chloroformate.
Katakai R and Iizuka Y
The Journal of Organic Chemistry, 50(5), 715-716 (1985)
Trichloromethyl chloroformate. Reaction with amines, amino acids, and amino alcohols.
Kurita K, et al.
The Journal of Organic Chemistry, 41(11), 2070-2071 (1976)

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