{{chembox| Verifiedfields = changed| Watchedfields = changed| verifiedrevid = 470617146| ImageFile = Triphosgen Strukturformel.svg| ImageFile1 =Triphosgene-3D-spacefill.png| ImageSize = | PIN = Bis(trichloromethyl) carbonate| OtherNames = BTC|Section1={{Chembox Identifiers

correct|chemspider}}| ChemSpiderID = 85216| InChI = 1/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9| InChIKey = UCPYLLCMEDAXFR-UHFFFAOYAA

correct|chemspider}}| StdInChI = 1S/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9

correct|chemspider}}| StdInChIKey = UCPYLLCMEDAXFR-UHFFFAOYSA-N

correct|CAS}}| CASNo = 32315-10-9

correct|FDA}}| UNII = 2C0677Q3B2| PubChem = 94429| SMILES = ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl}}|Section2={{Chembox Properties| Formula = C3Cl6O3| MolarMass = 296.748 g/mol| Appearance = white solid| Density = 1.780 g/cm3| MeltingPtC = 80| BoilingPtC = 206| Solubility = Reacts| SolubleOther =

soluble in dichloromethaneJOURNAL, Ouimet MA, Stebbins ND, Uhrich KE, Biodegradable coumaric acid-based poly(anhydride-ester) synthesis and subsequent controlled release, Macromolecular Rapid Communications, 34, 15, 1231â€“1236, August 2013, 23836606, 3789234, 10.1002/marc.201300323,
soluble in THFJOURNAL, Tang S, Ikai T, Tsuji M, Okamoto Y, Immobilization and chiral recognition of 3,5-dimethylphenylcarbamates of cellulose and amylose bearing 4-(trimethoxysilyl)phenylcarbamate groups, Chirality, 22, 1, 165â€“172, January 2010, 19455617, 10.1002/chir.20722,
soluble in tolueneJOURNAL, Zhou Y, Gong R, Miao W, September 2006, New Method of Synthesizing N-Alkoxycarbonyl-N-arylamide with Triphosgene, Synthetic Communications, 36, 18, 2661â€“2666, 10.1080/00397910600764675, 98578315, }}|Section3={{Chembox Hazards| ExternalSDS =SDS Triphosgene| FlashPt = | AutoignitionPt =

id=330752

access-date=2018-06-12}}| GHSSignalWord = Danger

314|330}}

260

284

310}}}}}}Triphosgene (bis(trichloromethyl) carbonate (BTC) is a chemical compound with the formula OC(OCCl3)2. It is used as a solid substitute for phosgene, which is a gas and diphosgene, which is a liquid.BOOK, 10.1002/047084289X.rb200, Bis(trichloromethyl) Carbonate, Encyclopedia of Reagents for Organic Synthesis, 2001, Roestamadji, Juliatiek, Mobashery, Shahriar, 0471936235, JOURNAL, Heiner Eckert, Barbara Forster, 1987, Triphosgene, a Crystalline Phosgene Substitute, Angew. Chem. Int. Ed. Engl., 26, 9, 894â€“895, 10.1002/anie.198708941, Triphosgene is stable up to 200 Â°C. Triphosgene is used in a variety of halogenation reactions.

Preparation

This compound is commercially available. It is prepared by exhaustive free radical chlorination of dimethyl carbonate:

CH3OCO2CH3 + 6 Cl2 â†’ CCl3OCO2CCl3 + 6 HCl

Triphosgene can be easily recrystallized from hot hexanes.

Uses

Triphosgene is used as a reagent in organic synthesis as a source of CO2+. It behaves like phosgene, to which it cracks thermally:

Alcohols are converted to carbonates. Primary and secondary amines are converted to ureas and isocyanates.JOURNAL, Akiba T, Tamura O, Terashima S, 10.15227/orgsyn.075.0045, (4R,5S)-4,5-Diphenyl-3-Vinyl-2-Oxazolidinone, Organic Syntheses, 75, 45, 1998, JOURNAL, Tsai JH, Takaoka LR, Powell NA, Nowick JS, 10.15227/orgsyn.078.0220, Synthesis of Amino Acid Ester Isocyanates: Methyl (S)-2-Isocyanato-3-Phenylpropanoate, Organic Syntheses, 78, 220, 2002, JOURNAL, Du H, Zhao B, Shi Y, 10.15227/orgsyn.086.0315, Pd(0)-Catalyzed Diamination of Trans-1-Phenyl-1,3-Butadiene with Di-tert-Butyldiaziridinone as Nitrogen Source, Organic Syntheses, 86, 315, 2009, free, Triphosgene has been used to synthesize chlorides.JOURNAL, Ganiu MO, Nepal B, Van Houten JP, Kartika R, A decade review of triphosgene and its applications in organic reactions, Tetrahedron, 76, 47, 131553, November 2020, 33883783, 8054975, 10.1016/j.tet.2020.131553, Some Alkyl chlorides are prepared by treating alcohols with a mixture of triphosgene and pyridine. Alkyl dichlorides and trichlorides can similarly be synthesized using triphosgene. Vinyl chlorides are synthesized from ketones using triphosgene and DMF to form a Vilsmeier reagent, followed by a ring opening by chloride ions. Aryl chlorides can also be produced using a Vilsmeier reagent from triphosgene and DMF.

Safety

Triphosgene's low vapor pressure makes it possible for it to reach concentrations that are considered toxicologically unsafe.JOURNAL, Cotarca L, Geller T, RÃ©pÃ¡si J, 2017-09-15, Bis(trichloromethyl)carbonate (BTC, Triphosgene): A Safer Alternative to Phosgene?, Organic Process Research & Development, en, 21, 9, 1439â€“1446, 10.1021/acs.oprd.7b00220, free, While several properties of triphosgene are not yet readily available, it is known that it is very toxic if inhaled. A toxic gas is emitted if it comes in contact with water.WEB, 2009, Material Safety Data Sheet: Triphosgene,weblink February 17, 2022, Acros Organics, There is a lack of information and variability regarding the proper handling of triphosgene. It is assumed to have the same risks as phosgene.JOURNAL, Damle SB, Safe handling of diphosgene, triphosgene., Chemical & Engineering News, February 1993, 71, 6, 4,weblink JOURNAL, Pauluhn J, Phosgene inhalation toxicity: Update on mechanisms and mechanism-based treatment strategies, Toxicology, 450, 152682, February 2021, 33484734, 10.1016/j.tox.2021.152682, 231693591, free,

References

External links

- content above as imported from Wikipedia
- "Triphosgene" does not exist on GetWiki (yet)
- time: 10:34pm EDT - Thu, Apr 25 2024

[ this remote article is provided by Wikipedia ]

CONNECT

GetWiki

Triphosgene

Preparation

Uses

Safety

See also

References

External links