Triphosgene
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Names | ||||
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Preferred IUPAC name
Bis(trichloromethyl) carbonate | ||||
Other names
BTC
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Identifiers | ||||
3D model (JSmol)
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ChemSpider | ||||
ECHA InfoCard | 100.046.336 | |||
PubChem CID
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CompTox Dashboard (EPA)
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Properties | ||||
C3Cl6O3 | ||||
Molar mass | 296.748 g/mol | |||
Appearance | white crystals | |||
Density | 1.780 g/cm3 | |||
Melting point | 80 °C (176 °F; 353 K) | |||
Boiling point | 206 °C (403 °F; 479 K) | |||
Reacts | ||||
Solubility | *soluble in dichloromethane[1] | |||
Hazards | ||||
GHS labelling: | ||||
class="wikitable collapsible" style="min-width: 50em;" | ||||
Pictogram | Code | Symbol description | Image link | |
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GHS01 | {{GHS exploding bomb}} | Image:GHS-pictogram-explos.svg | Explosive |
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GHS02 | {{GHS flame}} | Image:GHS-pictogram-flamme.svg | |
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GHS03 | {{GHS flame over circle}} | Image:GHS-pictogram-rondflam.svg | |
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GHS04 | {{GHS gas cylinder}} | Image:GHS-pictogram-bottle.svg | |
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GHS05 | {{GHS corrosion}} | Image:GHS-pictogram-acid.svg | Corrosive |
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GHS06 | {{GHS skull and crossbones}} | Image:GHS-pictogram-skull.svg | Accute Toxic |
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GHS07 | {{GHS exclamation mark}} | Image:GHS-pictogram-exclam.svg | Irritant |
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GHS08 | {{GHS health hazard}} | Image:GHS-pictogram-silhouette.svg | Health Hazard |
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GHS09 | {{GHS environment}} | Image:GHS-pictogram-pollu.svg | Environment |
See also
- {{H-phrases}}
- {{P-phrases}}
- ‹The template Category link is being considered for merging.› Category:GHS templates
Pictogram | Code | Symbol description | Image link | |
---|---|---|---|---|
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GHS01 | {{GHS exploding bomb}} | Image:GHS-pictogram-explos.svg | Explosive |
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GHS02 | {{GHS flame}} | Image:GHS-pictogram-flamme.svg | |
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GHS03 | {{GHS flame over circle}} | Image:GHS-pictogram-rondflam.svg | |
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GHS04 | {{GHS gas cylinder}} | Image:GHS-pictogram-bottle.svg | |
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GHS05 | {{GHS corrosion}} | Image:GHS-pictogram-acid.svg | Corrosive |
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GHS06 | {{GHS skull and crossbones}} | Image:GHS-pictogram-skull.svg | Accute Toxic |
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GHS07 | {{GHS exclamation mark}} | Image:GHS-pictogram-exclam.svg | Irritant |
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GHS08 | {{GHS health hazard}} | Image:GHS-pictogram-silhouette.svg | Health Hazard |
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GHS09 | {{GHS environment}} | Image:GHS-pictogram-pollu.svg | Environment |
See also
- {{H-phrases}}
- {{P-phrases}}
- ‹The template Category link is being considered for merging.› Category:GHS templates[5]
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| Danger
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| H314, H330[5]
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| P260, P280, P284, P305+P351+P338, P310[5]
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| Safety data sheet (SDS) | SDS Triphosgene |-
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Triphosgene (bis(trichloromethyl) carbonate (BTC), C3Cl6O3) is a chemical compound that is used as a safer substitute for phosgene, because, at room temperature, it is a solid crystal, as opposed to phosgene, which is a gas.[6] Triphosgene crystals decompose above 200 °C.[7]
Preparation
This compound is commercially available. It is prepared by exhaustive free radical chlorination of dimethyl carbonate:[6]
- CH3OCO2CH3 + 6 Cl2 → CCl3OCO2CCl3 + 6 HCl
Triphosgene can be easily recrystallized from boiling hexanes to yield pure white crystals.
Uses
Triphosgene is used as a reagent in organic synthesis and is a less hazardous substitute for phosgene for a variety of chemical transformations including to bond one carbonyl group to two alcohols, and to convert an amine group into isocyanate.[6]
Safety
The toxicity of triphosgene is the same as phosgene since it decomposes to phosgene on heating and upon reaction with nucleophiles. Even trace moisture leads to formation of phosgene. Therefore, this reagent can be safely handled if one takes all the precautions as for phosgene.[8]
See also
References
- ^ Michelle A. Ouimet, Nicholas D. Stebbins, Kathryn E. Uhrich (2013). "Biodegradable Coumaric Acid-Based Poly(anhydride-ester) Synthesis and Subsequent Controlled Release". Macromol. Rapid Commun. 34 (15): 1231–1236. doi:10.1002/marc.201300323. PMC 3789234. PMID 23836606.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ Tang, Shouwan; Ikai, Tomoyuki; Tsuji, Masashi; Okamoto, Yoshio (2010). "Immobilization and chiral recognition of 3,5-dimethylphenylcarbamates of cellulose and amylose bearing 4-(trimethoxysilyl)phenylcarbamate groups". Chirality. 22 (1): 165–172. doi:10.1002/chir.20722. PMID 19455617.
- ^ Zhou, Yuhan; Gong, Runjun; Miao, Weirong (2006-09-01). "New Method of Synthesizing N‐Alkoxycarbonyl‐N‐arylamide with Triphosgene". Synthetic Communications. 36 (18): 2661–2666. doi:10.1080/00397910600764675. ISSN 0039-7911.
- ^ a b "Globally Harmonized System of Classification and Labelling of Chemicals" (pdf). 2021. Annex 3: Codification of Statements and Pictograms (pp 268–385).
- ^ a b c Sigma-Aldrich Co., Triphosgene. Retrieved on 2018-06-12.
- ^ a b c Dr. Heiner Eckert; Dr. Barbara Forster (1987). "Triphosgene, a Crystalline Phosgene Substitute". Angew. Chem. Int. Ed. Engl. 26 (9): 894–895. doi:10.1002/anie.198708941.
- ^ Dr. Heiner Eckert (2011). "Phosgenation Reactions with Phosgene from Triphosgene". Chim. Oggi Chem. Today. 29 (6): 40–46.
- ^ Suresh B. Damle (1993-02-08). "Safe handling of diphosgene, triphosgene". Chemical & Engineering News. 71 (6): 4.