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Triphosgene

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
MDL Number:
MFCD00062848
MOL File:
32315-10-9.mol
MSDS File:
SDS
Last updated:2023-12-22 17:53:22

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)
FDA UNII 2C0677Q3B2
EPA Substance Registry System Methanol, trichloro-, carbonate (2:1) (32315-10-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
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(47)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.14283 Bis(trichloromethyl) carbonate for synthesis 32315-10-9 25g $153 2024-03-01 Buy
Sigma-Aldrich 8.14283 Bis(trichloromethyl) carbonate for synthesis 32315-10-9 1kg $240 2024-03-01 Buy
Sigma-Aldrich 8.14283 Bis(trichloromethyl) carbonate for synthesis 32315-10-9 100g $252 2024-03-01 Buy
Sigma-Aldrich 15217 Bis(trichloromethyl) carbonate purum, ≥99.0% (AT) 32315-10-9 10g $117 2024-03-01 Buy
Sigma-Aldrich 15217 Bis(trichloromethyl) carbonate purum, ≥99.0% (AT) 32315-10-9 50g $388 2024-03-01 Buy
Product number Packaging Price Buy
8.14283 25g $153 Buy
8.14283 1kg $240 Buy
8.14283 100g $252 Buy
15217 10g $117 Buy
15217 50g $388 Buy

Triphosgene Chemical Properties,Uses,Production

Toxicity

As a common production raw material for chemical enterprises, Sanguang gas is not listed in the list of hazardous chemicals, and its risk is not familiar and understood by many users, which often leads to decomposition and poisoning accidents. Therefore, it is of great practical significance to study the hazards and safety measures in the use of Triphosgene. Based on the characteristic identification of triphosgene, the hazards in the process of dissolution and reaction are identified and analyzed, and the corresponding safety measures in the use of Triphosgene are put forward according to the results of hazard identification and analysis. Triphosgene has gradually become the raw material for acyl chlorination in many enterprises because it is a non hazardous chemical, relatively stable material properties, easy transportation and easy treatment of tail gas. However, if the safety measures are not appropriate during the transportation, storage and use of triphosgene, it is very easy to cause poisoning accidents.

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 can be employed as a reagent to prepare:

  • Thiocarbonates from thiols and alcohols by one-pot, three-component reaction.
  • Substituted azetidin-2-ones from acids and imines via ketene–imine cycloaddition reaction.
  • Methyl (S)-2-isocyanato-3-phenylpropanoate from L-phenylalanine methyl ester hydrochloride in the presence of sodium bicarbonate.
  • Acyl azides derivatives from various carboxylic acids and sodium azide.
  • Immunosuppressant agent cyclosporin by solid-phase peptide synthesis.
  • Allyl azides from allyl alcohols and sodium azide in one pot method.
  • Esterification coupling reagent di-2-thienyl carbonate, from 2(5H)-thiophenone.
  • 2-Chloronicotinaldehydes via cyclization of the corresponding enamides.

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.

Uses

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

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.]

594-42-3
32315-10-9
Synthesis of Triphosgene from Perchloromethylmercaptan
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View Lastest Price from Triphosgene manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Triphosgene pictures 2024-03-19 Triphosgene
32315-10-9
US $0.00 / KG 1KG ≥99.5% 2000mt/year Jinan Finer Chemical Co., Ltd
Triphosgene pictures 2024-03-15 Triphosgene
32315-10-9
US $0.00 / KG/Tin 1000Kg/Drum 99.5 10000 Gansu Jinyuantai New Material Co., Ltd.
Triphosgene pictures 2023-12-23 Triphosgene
32315-10-9
US $50.00-1.00 / KG 1KG 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
  • Triphosgene pictures
  • Triphosgene
    32315-10-9
  • US $0.00 / KG
  • ≥99.5%
  • Jinan Finer Chemical Co., Ltd
  • Triphosgene pictures
  • Triphosgene
    32315-10-9
  • US $0.00 / KG/Tin
  • 99.5
  • Gansu Jinyuantai New Material Co., Ltd.
  • Triphosgene pictures
  • Triphosgene
    32315-10-9
  • US $50.00-1.00 / KG
  • 99%
  • Henan Fengda Chemical Co., Ltd
TRIPHOSGENE CARBONIC ACID BISTRICHLOR METHYL ESTER TriphosgeneForSynthesis Triphosgene98+% Methanol, trichloro-, carbonate (2:1) TRICHLOROMETHANOLCARBONATE TRIPHOSGENE (BIS-(TRICHLOROMETHYL)CARBONATE) Bis(trichloroMethyl) carbonate puruM, >=99.0% (AT) Triphosgene reagent grade, 98% Three chloroMethyl carbonate Triphosgene, 98.0%(T) tri-Phosgene, Triphosgene Carbonic acid bis(trichloromethyl) Carbonic acid bis(trichloromethyl) ester Trichloromethoxyformic acid trichloromethyl ester Triphosgene,99% Triphosgene (Technical grade) Bis(trichloromethyl)carbonat triphosqene Triphosgene, 99% 10GR Triphosgene, 99% 5GR Bis(trichlormethyl)carbonat Methanol, 1,1,1-trichloro-, 1,1'-carbonate BIS(TRICHLOROMETHYL) CARBONATE Triphosgene, 98% [Bis-(trichloromethyl)-carbonat] TRIPHOSGEN BIS(TRICHLOROMETHYL) CARBONATE FOR SYNTH Triphosgene, BTC Triphosg TriphosGmene,98% Ritalin Impurity 13 32315-10-9 Cl3COCOOCCl3 CCl3O2CO C3Cl6O3 C3O3Cl6 Building Blocks Carbonyl Compounds Carbonates Organic Building Blocks Coupling Phosgene Derivatives Synthetic Reagents Aliphatics Other Reagents 32315-10-9