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, 98% ^*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

Studies on quinazolines IX:¹ Fluorination versus 1,2-migration in the reaction of 1,3-bifunctionalized amino-2-propanol with DAST

10.1016/S0040-4039(98)01905-4

The research aimed to introduce a fluorine atom into the structure of 3-[2-hydroxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]quinazolin-2,4-(1H, 3H)-dione (4), a compound of interest due to its partial structure similar to previously studied compounds with pharmacological activities. The study explored the reaction of 4 with diethylaminosulfur trifluoride (DAST), expecting a straightforward fluorination. However, instead of the desired product, a 1,2-migration occurred, leading to the formation of N-[2-fluoro-3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]phthalimide (11a) in 13% yield and N-[2-fluoromethyl-2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]phthalimide (11b) in 73% yield. The reaction was proposed to proceed through a spiro-aziridinium intermediate, resulting in an unexpected migration. This discovery provides a practical approach for the preparation of 1-fluoroethylamine derivatives and contributes to the understanding of DAST-induced migrations in chemical synthesis. Key chemicals used in the process included DAST, phthalimide, glycidol, 2-methoxyphenylpiperazine, hydrazine monohydrate, isatoic anhydride, and triphosgene.

Selective kainate receptor (GluK1) ligands structurally based upon 1H-cyclopentapyrimidin-2,4(1 H,3 H)-dione: Synthesis, molecular modeling, and pharmacological and biostructural characterization

10.1021/jm2004078

This research focuses on the development of selective kainate receptor (GluK1) ligands based on the structure of 1H-cyclopentapyrimidin-2,4(1H,3H)-dione. The purpose of the study was to synthesize new thiophene-based GluK1 agonists and antagonists to better understand the physiological functions of GluK1 in the central nervous system, which is implicated in various neurological diseases such as depression, pain, neurodegeneration, and epilepsy. The researchers synthesized a series of compounds, including 6a–c and 7a–d, and evaluated their pharmacological properties. The most significant finding was that compound 7b was the most subtype-selective ligand reported to date for GluK1 versus GluK3. The antagonist 7a was cocrystallized with the GluK1 ligand binding domain, revealing the largest flexibility in GluK1 ligand binding domain opening upon binding of a ligand seen to date. These results provide new insights into the molecular mechanism of GluK1 receptor ligand binding and could lead to the development of new tool compounds for studying kainate receptor function. Some of the key chemicals used in the synthesis process include triphosgene, sodium methoxide, sodium isocyanate, and various amino acid derivatives.