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Merck
CN

23261

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

Key Documents

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Product Name

Trichloromethyl chloroformate, ≥97.0% (GC)

InChI key

HCUYBXPSSCRKRF-UHFFFAOYSA-N

InChI

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

SMILES string

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

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

Quality Level

100

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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

Storage Class

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

ppe

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

Regulatory Information

监管及禁止进口产品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCN7777
BCCN2072
BCCM1276
BCCK6163
BCCG3835

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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)
Topics in Inorganic and General Chemistry, 24, 535-541 (1996)
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)
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