Toxicity
ChemicalBook > CAS DataBase List > Triphosgene

Triphosgene

Toxicity
Product Name
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
Formula Weight
296.73
MOL File
32315-10-9.mol
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Triphosgene Property

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)
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Safety

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
F 
10-19-21
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
II
HS Code 
29209010
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

H330Fatal if inhaled

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.14283
Product name
Bis(trichloromethyl) carbonate
Purity
for synthesis
Packaging
25g
Price
$153
Updated
2024/03/01
Sigma-Aldrich
Product number
8.14283
Product name
Bis(trichloromethyl) carbonate
Purity
for synthesis
Packaging
1kg
Price
$240
Updated
2024/03/01
Sigma-Aldrich
Product number
8.14283
Product name
Bis(trichloromethyl) carbonate
Purity
for synthesis
Packaging
100g
Price
$252
Updated
2024/03/01
Sigma-Aldrich
Product number
15217
Product name
Bis(trichloromethyl) carbonate
Purity
purum, ≥99.0% (AT)
Packaging
10g
Price
$117
Updated
2024/03/01
Sigma-Aldrich
Product number
15217
Product name
Bis(trichloromethyl) carbonate
Purity
purum, ≥99.0% (AT)
Packaging
50g
Price
$388
Updated
2024/03/01
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Triphosgene Chemical Properties,Usage,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

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

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

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.

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.]

Triphosgene Preparation Products And Raw materials

Raw materials

2,2'-Azobis-(2,4-dimethylvaleronitrile) (V-65) Chlorine Formaldehyde

Preparation Products

Ritonavir 4-Cyanophenyl isocyanate 3-Bromophenyl isocyanate 3-METHOXYPHENYL ISOCYANATE 2-CHLOROBENZYL CHLOROFORMATE 1-CHLORO-2-METHYLPROPYL CHLOROFORMATE Fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate 2,2,2-Trichloroethyl chloroformate 4-DIMETHYLAMINOPHENYL ISOCYANATE 2-Methoxyphenyl isocyanate N-Boc-N'-(2-chlorobenzyloxycarbonyl)-L-lysine BIS(4-NITROPHENYL) CARBONATE Pentyl isocyanate Phenyl chloroformate 4-Methylbenzyl isocyanate H-LYS(2-CL-Z)-OH (S)-3-TERT-BUTYL-2,5-PIPERAZINEDIONE 5-FLUORO-2H-3,1-BENZOXAZINE-2,4(1H)-DIONE 2-(TRIFLUOROMETHYL)PHENYL ISOCYANATE 4-(2-KETO-1-BENZIMIDAZOLINYL)PIPERIDINE 2-Chlorophenyl isocyanate (S)-(-)-4-tert-Butyloxazolidine-2,5-dione DIRECT YELLOW 50 3-(Trifluoromethyl)phenyl isocyanate 4-Methoxyphenyl isocyanate 3,5-DIMETHYLISOXAZOL-4-YL ISOCYANATE 2-FLUOROPHENYL ISOCYANATE 2-CHLORO-5-(TRIFLUOROMETHYL)PHENYL ISOCYANATE 1-Naphthyl isocyanate 3,4-(METHYLENEDIOXY)PHENYL ISOCYANATE 5-Bromothiophene-2-carbaldehyde 4-Fluorophenyl isocyanate (1-METHYL-1H-PYRROL-2-YL)METHYLAMINE 2-NAPHTHYL ISOCYANATE Direct Red 75 tetrasodium salt 1,5-Diphenylcarbazide 4-Methoxybenzyl isocyanate 3-FLUOROPHENYL ISOCYANATE 3,4-(METHYLENEDIOXY)PHENYL ISOCYANATE
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Triphosgene Suppliers

Belgium 4 Canada 3 China 305 China Hong Kong 1 Czech Republic 1 Europe 3 France 1 Germany 9 India 57 Japan 11 Poland 1 Russia 1 Slovakia 1 South Korea 1 Switzerland 5 The Netherlands 1 United Kingdom 16 United States 54 Global 475
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View Lastest Price from Triphosgene manufacturers

Gansu Jinyuantai New Material Co., Ltd.
Product
Triphosgene 32315-10-9
Price
US $0.00/KG/Tin
Min. Order
1000Kg/Drum
Purity
99.5
Supply Ability
10000
Release date
2021-10-12
Jinan Finer Chemical Co., Ltd
Product
Triphosgene 32315-10-9
Price
US $0.00/KG
Min. Order
1KG
Purity
≥99.5%
Supply Ability
2000mt/year
Release date
2023-06-29
Hebei Weibang Biotechnology Co., Ltd
Product
Triphosgene 32315-10-9
Price
US $10.00/kg
Min. Order
1kg
Purity
99.5%
Supply Ability
100 TON
Release date
2024-10-25

32315-10-9, TriphosgeneRelated Search:

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  • Triphosgene,99%
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  • BIS(TRICHLOROMETHYL) CARBONATE FOR SYNTH
  • Triphosgene, BTC
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  • TriphosGmene,98%
  • Ritalin Impurity 13
  • Triphosgene, ≥ 98.0%
  • 32315-10-9
  • C3O3Cl6
  • Cl3COCOOCCl3
  • CCl3O2CO
  • C3Cl6O3
  • Building Blocks
  • Carbonyl Compounds
  • Carbonates
  • Organic Building Blocks
  • Coupling
  • Phosgene Derivatives
  • Synthetic Reagents
  • Aliphatics
  • Other Reagents
  • 32315-10-9