23261

Trichloromethyl chloroformate

≥97.0% (GC)

• Synonym(s): TCF, Diphosgene, di-Phosgene
• 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

Properties

• 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

Description

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

Safety Information

• pictograms: GHS06,GHS05
• signalword: Danger
• hcodes: H302,H314,H330
• pcodes: P260 - P280 - P301 + P312 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter