trichloromethyl chloroformate

• ChemBase ID: 123315
• Molecular Formular: C2Cl4O2
• Molecular Mass: 197.8322
• Monoisotopic Mass: 195.86523996
• SMILES: C(OC(=O)Cl)(Cl)(Cl)Cl
• Canonical SMILES: ClC(=O)OC(Cl)(Cl)Cl
• InChI: InChI=1S/C2Cl4O2/c3-1(7)8-2(4,5)6
• InChIKey: HCUYBXPSSCRKRF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trichloromethyl chloroformate; chloro(trichloromethoxy)methanone
• IUPAC Traditional name: trichloromethyl chloroformate; diphosgene
• Synonyms: trichloromethyl carbonochloridate; Diphosgene; trichloromethyl chloroformate; Diphosgene; di-Phosgene; Trichloromethyl chloroformate; Chloroformic acid trichloromethyl ester; 双光气; 氯代甲酸三氯甲酯; 氯甲酸三氯甲酯

Database IDs

• CAS Number: 503-38-8
• EC Number: 207-965-9
• MDL Number: MFCD00015553
• Beilstein Number: 970225
• Merck Index: 143334
• PubChem SID: 24853917; 162217668
• PubChem CID: 10426
• Chemspider ID: 21154424
• Wikipedia Title: Diphosgene

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.3808258
• LogD (pH = 7.4): 3.3808258
• Log P: 3.3808258
• Molar Refractivity: 14.7329 cm^3
• Polarizability: 13.222563 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: insol. in water
• Apperance: liquid at room temperature
• Melting Point: -57 °C; -57°C
• Boiling Point: 128 °C; 128°C; 20 °C/10 mmHg(lit.)
• Flash Point: >110°C(230°F); 32°C
• Density: 1.639 g/mL at 20 °C; 1.640; 1.65 g/cm^3
• Refractive Index: 1.4570; n20/D 1.458

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: LQ7350000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3277; UN3390
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; I
• Risk Statements: 26/28-34; 26-34
• Safety Statements: 26-27/28-36/37/39-45; 26-28-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• Main Hazard: toxic
• GHS Hazard statements: H300-H314-H330; H330-H314-H318
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P305 + P351 + P338; P280-P303+P361+P353-P305+P351+P338-P304+P340-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3277 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 98%
• Linear Formula: ClCOOCCl3

DETAILS

Sigma Aldrich - 23261

Other Notes
Easy to handle substitute for phosgene7,8,9; In-situ charcoal-catalyzed decomposition to phosgene and reaction with amino acids to N-carboxy anhydrides10
Packaging
10, 50 mL in glass bottle
Application
Reactant for preparation of:
• Cyclic carbamimidates using a monophosphine gold(i) catalyst1
• N-Alkenyl and cycloalkyl carbamates as dual acting histamine H3 and H4 receptor ligands2
• Prostate-specific membrane antigen-targeted anticancer prodrugs3
• Potential west nile virus protease inhibitors4
• Antibody-drug conjugates (ADCs)5
• Erythromycin A derivatives6

REFERENCES

• Convenient replacement for phosgene in many reactions, for example:
• Conversion of amines to isocyanates: J. Org. Chem., 41, 2070 (1976); Org. Synth. Coll ., 6, 715 (1988). For aliphatic amines, best results were obtained in the presence of the hindered amine 1,8-Bis(dimethylamino)naphthalene, L00313: J. Org. Chem., 61, 3883 (1996).
• Dehydration of N-monosubstituted formamides to isocyanides: Angew. Chem. Int. Ed., 16, 259 (1977).
• Formation of nitriles from oximes Synthesis, 1037 (1986); or carboxamides: Tetrahedron Lett., 27, 2203 (1986).
• See also Triphosgene, A14932, and Oxalyl chloride, A18012.