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Triphosgene

Triphosgene Structure
CAS No.
32315-10-9
Chemical Name:
Triphosgene
Synonyms
BIS(TRICHLOROMETHYL) CARBONATE;TRIPHOSGEN;Triphosg;Triphosgene, BTC;BIS(TRICHLOROMETHYL) CARBONATE FOR SYNTH;Triphosgene, 98% [Bis-(trichloromethyl)-carbonat];TRIPHOSGENE;triphosqene;Triphosgene98+%;Triphosgene,99%
CBNumber:
CB2420273
Molecular Formula:
C3Cl6O3
Molecular Weight:
296.73
MOL File:
32315-10-9.mol
MSDS File:
SDS
Modify Date:
2024/8/21 22:41:43

Triphosgene Properties

Melting point 79-83 °C (lit.)
Boiling point 203-206 °C (lit.)
Density 1.78
vapor pressure 16 hPa (90 °C)
Flash point 203-206°C
storage temp. 2-8°C
solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form Crystalline Powder, Crystals and/or Chunks
color White to off-white
Water Solubility practically insoluble
Sensitive Moisture Sensitive
BRN 1787583
InChIKey UCPYLLCMEDAXFR-UHFFFAOYSA-N
CAS DataBase Reference 32315-10-9(CAS DataBase Reference)
EPA Substance Registry System Methanol, trichloro-, carbonate (2:1) (32315-10-9)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS05,GHS06
Signal word  Danger
Hazard statements  H314-H330
Precautionary statements  P260-P271-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Hazard Codes  T+,Xn,T
Risk Statements  26-34-29-36/37/38-20/21/22-23/24/25
Safety Statements  36/37/39-45-9-26-36-7/9
RIDADR  UN 2928 6.1/PG 2
WGK Germany  2
10-19-21
TSCA  Yes
HazardClass  6.1
PackingGroup  II
HS Code  29209010
NFPA 704
1
4 0
W

Triphosgene price More Price(17)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 8.14283 Bis(trichloromethyl) carbonate for synthesis 32315-10-9 5G ₹2990 2022-06-14 Buy
Sigma-Aldrich(India) 8.14283 Bis(trichloromethyl) carbonate for synthesis 32315-10-9 25G ₹6880 2022-06-14 Buy
Sigma-Aldrich(India) 8.14283 Bis(trichloromethyl) carbonate for synthesis 32315-10-9 100G ₹8650 2022-06-14 Buy
Sigma-Aldrich(India) 8.14283 Bis(trichloromethyl) carbonate for synthesis 32315-10-9 1KG ₹15290 2022-06-14 Buy
Sigma-Aldrich(India) 330752 Triphosgene reagent grade, 98% 32315-10-9 5G ₹3344.93 2022-06-14 Buy
Product number Packaging Price Buy
8.14283 5G ₹2990 Buy
8.14283 25G ₹6880 Buy
8.14283 100G ₹8650 Buy
8.14283 1KG ₹15290 Buy
330752 5G ₹3344.93 Buy

Triphosgene Chemical Properties,Uses,Production

Description

Triphosgene is also known as solid phosgene. Its chemical name is bis (Trichloromethyl) carbonate, and its English name is bisgriehloromethyl) carbonate or triphosgene, abbreviated as BTC. Triphosgene is a white crystal, similar to the smell of phosgene. It is mainly used to synthesize chloroformate, isocyanate, polycarbonate and acyl chloride. It is widely used as an intermediate in plastics, medicine, herbicides and pesticides.

Chemical Properties

White solid

Uses

Triphosgene is used as a carbonylating agent for aza-peptide synthesis. It reacts with several alfa-amino acids to give the corresponding N-carboxyanhydrides. It is involved in the preparation of the esterification coupling reagent, di-2-thienyl carbonate from 2(5H)-thiophenone. Further, it is used as a reagent in organic synthesis and converts an amino group into isocyanate. In addition to this, it is employed in the preparation of 2-chloronicotinaldehydes through cyclization of the corresponding enamides. It is considered as a useful substitute for phosgene.

Reactions

The Triphosgene reaction is quenched very carefully by dropwise addition of 75 mL of saturated aqueous sodium sulfate solution  (Notes 5 and 6). The resulting white granular precipitate or slurry is  removed by vacuum filtration through Celite, and the filter cake is  washed with three portions of 75 mL of chloroform .

General Description

Triphosgene [Bis(trichloromethyl)carbonate] is a versatile organic reagent used in organic synthesis alternative to phosgene. A catalytic amount of triphosgene is particularly used in chloroformylations, carbonylations, chlorinations, and dehydration reactions.

Safety

Triphosgene's low vapor pressure makes it possible for it to reach concentrations that are considered toxicologically unsafe. While several properties of triphosgene are not yet readily available, it is known that it is extremely toxic if inhaled. A toxic gas is emitted if it comes in contact with water. There is a lack of information and variability regarding the proper handling of triphosgene. It is assumed to have the same risks as phosgene.

Synthesis

Triphosgene is synthesized by exhaustive free radical chlorination of dimethyl carbonate:
CH3OCO2CH3 + 6 Cl2 → CCl3OCO2CCl3 + 6 HCl
Triphosgene can be easily recrystallized from hot hexanes. 

Purification Methods

It is a good solid substitute for phosgene (using a third mol per mol). Crystallise it from pet ether (b 60-80o), wash it with anhydrous cold Et2O, de-gas it at 200mm then dry at 0.1mm (over H2SO4). It has IR: max 900 and 1900 cm-1 . It is a lachrymator, is TOXIC and should be handled with gloves and in an efficient fume hood. [Hales et al. J Chem Soc 620 1957, Eckert & Forster Angew Chem, Int Ed Engl 26 894 1987, Aldrichimica Acta 21 47 1988, Beilstein 3 H 17, 3 I 8, 3 II 16, 3 III 36, 3 IV 33.]

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