Triphosgene

Base Information

• Chemical Name: Triphosgene
• CAS No.: 32315-10-9
• Deprecated CAS: 1026306-50-2
• Molecular Formula: C3Cl6O3
• Molecular Weight: 296.749
• Hs Code.: 29209010
• European Community (EC) Number: 250-986-3
• UNII: 2C0677Q3B2
• DSSTox Substance ID: DTXSID00865631
• Nikkaji Number: J24.122I
• Wikipedia: Triphosgene
• Wikidata: Q421346
• Mol file: 32315-10-9.mol

Synonyms:bis(trichloromethyl) carbonate;triphosgene

Chemical Property of Triphosgene

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0.263mmHg at 25°C
• Melting Point: 78-82 °C
• Refractive Index: 1.532
• Boiling Point: 204.5 °C at 760 mmHg
• Flash Point: 53.3 °C
• PSA: 35.53000
• Density: 1.898 g/cm³
• LogP: 3.79500
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: practically insoluble
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 295.794910
• Heavy Atom Count: 12
• Complexity: 150

Purity/Quality:

99.5%, ^*data from raw suppliers

Triphosgene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+, Xn
• Hazard Codes: T+,Xn,T
• Statements: 26-34-29-36/37/38-20/21/22-23/24/25
• Safety Statements: 36/37/39-45-9-26-36-7/9

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(=O)(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl
• 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.
• Uses: An efficient carbonylating agent for liquid and solid-phase aza-peptide synthesis. 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. 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.

Technology Process of Triphosgene

There total 9 articles about Triphosgene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

carbonic acid dimethyl ester (616-38-6) → bis(trichloromethyl) carbonate (32315-10-9)

Guidance literature:

With chlorine; In tetrachloromethane; for 18h; Irradiation;

DOI:10.1080/00397919308012605

Reference yield:

→ bis(trichloromethyl) carbonate (32315-10-9) + N-methylheptylamine (36343-05-2)

Guidance literature:

Reference yield:

chlorothio-trichloro-methane (594-42-3) → bis(trichloromethyl) carbonate (32315-10-9)

Guidance literature:

With sulfur dioxide; In dichloromethane; water; at 10 ℃; for 4h;

upstream raw materials:

carbonic acid chloromethyl ester-dichloromethyl ester

methyl 1,1,1-trichloromethyl carbonate

methyl chloroformate

carbonic acid dimethyl ester

Downstream raw materials:

phosgene

carbonochloridic acid 3-methyl-butyl ester

Cholesteryl chloroformate

acetic anhydride

Refernces

• 1、 Madhukar Nalavde,Joshi. "Synthesis of new fluorine substituted hydrazinecarboxamides and hydrazine carbothioamides having antitubercular and fungicidal activity". . p. 634 - 637. Retrieved 2007/10/03.
• 2、 Falb,Nudelman,Hassner. "A convenient synthesis of chiral oxazolidin-2-ones and thiazolidin-2-ones and an improved preparation of triphosgene". . p. 2839 - 2844. Retrieved 2007/10/02.