All Photos(1)
Synonym(s):
TCF, Diphosgene, di-Phosgene
Linear Formula:
ClCOOCCl3
CAS Number:
Molecular Weight:
197.83
Beilstein:
970225
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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
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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Related Categories
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:
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
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Skin Corr. 1B
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
监管及禁止进口产品
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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Find documentation for the products that you have recently purchased in the Document Library.
Synthesis of some aromatic diisocyanides with trichloromethyl chloroformate.
Efraty A, et al.
The Journal of Organic Chemistry, 45(20), 4059-4061 (1980)
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)
L.N. Pridgen et al.
The Journal of Organic Chemistry, 54, 3231-3231 (1989)
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