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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

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.

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
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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

23261-VAR:
23261-50ML:
23261-10ML:
23261-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Topics in Inorganic and General Chemistry, 24, 535-541 (1996)
L.N. Pridgen et al.
The Journal of Organic Chemistry, 54, 3231-3231 (1989)
Trichloromethyl chloroformate. Reaction with amines, amino acids, and amino alcohols.
Kurita K, et al.
The Journal of Organic Chemistry, 41(11), 2070-2071 (1976)
H. Ogura et al.
Bulletin of the Chemical Society of Japan, 56, 2485-2485 (1983)
Single-pot reductive conversion of amino acids to their respective 2-oxazolidinones employing trichloromethyl chloroformate as the acylating agent: A multigram synthesis.
Pridgen L N, et al.
The Journal of Organic Chemistry, 54(13), 3231-3233 (1989)
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