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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/REAXYS Number:
970225
EC Number:
207-965-9
MDL number:
MFCD00015553
UNSPSC Code:
12352108
PubChem Substance ID:
57648028
NACRES:
NA.22

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

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

signalword

Danger

Hazard Classifications

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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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