Triphosgene

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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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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

Henan Fengda Chemical Co., Ltd

Product: Triphosgene 32315-10-9
Price: US $50.00-1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: g-kg-tons, free sample is available
Release date: 2023-12-22

32315-10-9, TriphosgeneRelated Search:

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TRIPHOSGENE

BIS(TRICHLOROMETHYL) CARBONATE

CARBONIC ACID BISTRICHLOR METHYL ESTER

TriphosgeneForSynthesis

Triphosgene98+%

Triphosgene, 98% [Bis-(trichloromethyl)-carbonat]

Methanol, trichloro-, carbonate (2:1)

TRICHLOROMETHANOLCARBONATE

TRIPHOSGENE (BIS-(TRICHLOROMETHYL)CARBONATE)

TRIPHOSGEN

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

Bis(trichlormethyl)carbonat

Trichloromethoxyformic acid trichloromethyl ester

Triphosgene,99%

Triphosgene (Technical grade)

BIS(TRICHLOROMETHYL) CARBONATE FOR SYNTH

Triphosgene, BTC

Bis(trichloromethyl)carbonat

triphosqene

Triphosgene, 99% 10GR

Triphosgene, 99% 5GR

Triphosg

Methanol, 1,1,1-trichloro-, 1,1'-carbonate

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

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32315-10-9