23261
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
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
EC Number:
207-965-9
Beilstein/REAXYS Number:
970225
MDL number:
Assay:
≥97.0% (GC)
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
Application
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:
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.
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
Other Notes
Easy to handle substitute for phosgene; In-situ charcoal-catalyzed decomposition to phosgene and reaction with amino acids to N-carboxy anhydrides
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Danger
hcodes
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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R. Katakai et al.
The Journal of Organic Chemistry, 50, 715-715 (1985)
K. Kunita et al.
Organic Syntheses, 59, 195-195 (1980)
Synthesis of some aromatic diisocyanides with trichloromethyl chloroformate.
Efraty A, et al.
The Journal of Organic Chemistry, 45(20), 4059-4061 (1980)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 23261-50ML | 04061838135094 |
| 23261-10ML | 04061838783592 |