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23261 Sigma-Aldrich

Trichloromethyl chloroformate

≥97.0% (GC)

Synonym: Diphosgene, TCF, di-Phosgene

  • CAS Number 503-38-8

  • Linear Formula ClCOOCCl3

  • Molecular Weight 197.83

  •  Beilstein Registry Number 970225

  •  EC Number 207-965-9

  •  MDL number MFCD00015553

  •  PubChem Substance ID 57648028

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Properties

Related Categories Chemical Synthesis, Deprotecting Reagents, Other Deprotecting Reagents, Protection and Derivatization, Synthetic Reagents More...
InChI Key   HCUYBXPSSCRKRF-UHFFFAOYSA-N
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

Description

Other Notes

Easy to handle substitute for phosgene; In-situ charcoal-catalyzed decomposition to phosgene and reaction with amino acids to N-carboxy anhydrides

Packaging

10, 50 mL in glass bottle

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.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 3277 8(6.1) / PGII
WGK Germany 
3
RTECS 
LQ7350000
Protocols & Articles
Peer-Reviewed Papers
15

References

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