ditrichloromethyl carbonate

• ChemBase ID: 88396
• Molecular Formular: C3Cl6O3
• Molecular Mass: 296.7483
• Monoisotopic Mass: 293.79785994
• SMILES: O(C(=O)OC(Cl)(Cl)Cl)C(Cl)(Cl)Cl
• Canonical SMILES: O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl
• InChI: InChI=1S/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9
• InChIKey: UCPYLLCMEDAXFR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ditrichloromethyl carbonate
• IUPAC Traditional name: triphosgene
• Synonyms: Bis(trichloromethyl) carbonate; Triphosgene; Triphosgene; Bis(trichloromethyl) carbonate; tri-Phosgene; Bis(trichloromethyl) carbonate; Triphosgene; 1,1,1-Trichloromethanol 1,1'-Carbonate; Carbonic Acid Bis(trichloromethyl)ester; Bis(trichloromethyl)carbonate; Triphosgene (Technical grade); BTC; 二(三氯甲基)碳酸酯; 三光气; 三光气; 固体光气; 双(三氯甲基)碳酸酯

Database IDs

• CAS Number: 32315-10-9
• EC Number: 250-986-3
• MDL Number: MFCD00062848
• Beilstein Number: 1787583
• PubChem SID: 24849208; 162075354; 24859885
• PubChem CID: 94429
• Chemspider ID: 85216
• Wikipedia Title: Triphosgene

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.4449406
• LogD (pH = 7.4): 5.4449406
• Log P: 5.4449406
• Molar Refractivity: 12.2506 cm^3
• Polarizability: 19.750893 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Reacts in water
• Apperance: White solid
• Melting Point: 75-80 °C; 77-91°C; 79-83 °C(lit.); 80°C; 80-82°C
• Boiling Point: 203-206 °C(lit.); 203-206°C; 206°C
• Density: 1.600

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• Storage Warning: Moisture Sensitive; Very Toxic/Corrosive/Keep Cold/Moisture Sensitive/Store under Argon
• European Hazard Symbols: Toxic (T); Highly toxic (T+)
• UN Number: 2928; UN2928
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 23-29-34; 26-34
• Safety Statements: 36/37/39-45; 4-7/8-9-20-26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H314-H330; H330-H314-H318
• GHS Precautionary statements: P260-P280-P284-P305 + P351 + P338-P310; P260-P303+P361+P353-P304+P340-P305+P351+P338-P320-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2928 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (AT); 98%
• Grade: purum; reagent grade
• Linear Formula: Cl3COCOOCCl3

DETAILS

InterBioScreen - BB_SC-8946

T. pl.=87,8C

Sigma Aldrich - 15217

Other Notes
Crystalline, easy-to-handle substitute for phosgene; 1 mole of the reagent corresponds in its reactivity to 3 moles phosgene1,2,3,4

Sigma Aldrich - 330752

Application
Solid phosgene substitute for a variety of applications, including the one-pot preparation of allyl azides from allyl alcohols and sodium azide,1 and the preparation of the esterification coupling reagent, di-2-thienyl carbonate, from 2(5H)-thiophenone.2
Used in the preparation of 2-chloronicotinaldehydes via cyclization of the corresponding enamides.
Useful substitute for phosgene.
Packaging
5, 25, 100, 500 g in glass bottle

Toronto Research Chemicals - T810500

An efficient carbonylating agent for liquid and solid-phase aza-peptide synthesis.

REFERENCES

• Ferrari, B., et al.: Bioorg. Med. Chem. Lett., 4, 45 (1994)
• Convenient crystalline alternative to phosgene in many reactions. See also Trichloromethyl chloroformate, A17444. Possible applications include conversion of amines to isocyanates, diols to carbonates, acids to acyl halides, etc.: Angew. Chem. Int. Ed., 26, 894 (1987). For a brief review, see: J. Prakt. Chem./ Chem. Ztg., 337, 516 (1995); for a comprehensive review: Synthesis, 553 (1996).
• In combination with triphenylphosphine, is a mild reagent for the conversions of alcohols to alkyl chlorides: Synth. Commun., 23, 711 (1993), epoxides to vicinal dichlorides: Synth. Commun., 24, 1715 (1994), and acids to acyl chlorides: Tetrahedron Lett., 38, 6489 (1997).
• Trap for titanocycle intermediates in the bicyclization of enynes using the titanocene dichloride (Bis(cyclopentadienyl)titanium dichloride, A11456) - Mg metal system: J. Org. Chem., 63, 9285 (1998):
  
• In combination with triethylamine, dehydrates formamides to isocyanides, and carboxylic acids to their anhydrides: J. Org. Chem., 58, 1646 (1993); 59, 2913 (1994).
• In combination with Dimethyl sulfoxide, A13280, has been used for the low-temperature Swern-type oxidation of alcohols to aldehydes: J. Org. Chem., 56, 5948 (1991); 58, 1646 (1993); Org. Prep. Proced. Int., 24, 363 (1992). Compare Oxalyl chloride, A18012.