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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:
503-38-8
Molecular Weight:
197.83
Beilstein:
970225
EC Number:
207-965-9
MDL number:
MFCD00015553
UNSPSC Code:
12352108
PubChem Substance ID:
57648028
NACRES:
NA.22
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Quality Level

100

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.[1] It can react with amines, amino acids and amino alcohols to give the corresponding isocyanates, isocyanato acid chlorides and isocyanato chloroformates.[2]
TCF can also be used:
  • To synthesize N-carboxy α-amino acid anhydrides.[3]
  • As an acylating agent to synthesize oxazolidinones from α-amino alcohols.[4]
  • As a dehydrating agent to synthesize aromatic diisocyanides in the presence of triethylamine.[5]

Other Notes

Easy to handle substitute for phosgene[6][7][8]; In-situ charcoal-catalyzed decomposition to phosgene and reaction with amino acids to N-carboxy anhydrides[9]

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H302,H314,H330

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCM1276
BCCK6163
BCCG3835
BCCD6668
BCCC5567

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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)
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)
Synthesis of some aromatic diisocyanides with trichloromethyl chloroformate.
Efraty A, et al.
The Journal of Organic Chemistry, 45(20), 4059-4061 (1980)
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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