Diphosgene is an organic chemical compound with the formula ClCO2CCl3. This colorless liquid is a valuable reagent in the synthesis of organic compounds. Diphosgene is related to phosgene and has comparable toxicity, but is more conveniently handled because it is a liquid, whereas phosgene is a gas.
With α-amino acids diphosgene gives the acid chloride-isocyanates, OCNCHRCOCl, or N-carboxy-amino acid anhydrides depending on the conditions.[3]
It hydrolyzes to release HCl in humid air.
Diphosgene is used in some laboratory preparations because it is easier to handle than phosgene.
Role in warfareedit
Diphosgene was originally developed as a pulmonary agent for chemical warfare, a few months after the first use of phosgene. It was used as a poison gas in artillery shells by Germany during World War I. The first recorded battlefield use was in May 1916.[4] Diphosgene was developed because the vapors could destroy the filters in gas masks in use at the time.
Safetyedit
Diphosgene has a relatively high vapor pressure of 10 mm Hg (1.3 kPa) at 20 °C and decomposes to phosgene around 300 °C. Exposure to diphosgene is similar in hazard to phosgene.
^Keisuke Kurita and Yoshio Iwakura (1979). "Trichloromethyl Chloroformate as a Phosgene Equivalent: 3-Isocyanatopropanoyl Chloride". Organic Syntheses. 59: 195; Collected Volumes, vol. 6, p. 715.
^Lohs, K. H.: Synthetische Gifte; Berlin (east), 1974 (German).
^Kurita, K. "Trichloromethyl Chloroformate" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X.
^Jones, Simon; Hook, Richard (2007). World War I Gas Warfare Tactics and Equipment. Osprey Publishing. ISBN978-1-84603-151-9.
External linksedit
medical care guide.
, includes treatment advice
material safety data sheet (PDF, for phosgene and diphosgene treated as one).
MSDS for diphosgene specifically
January 01, 1970
diphosgene, organic, chemical, compound, with, formula, clco2ccl3, this, colorless, liquid, valuable, reagent, synthesis, organic, compounds, related, phosgene, comparable, toxicity, more, conveniently, handled, because, liquid, whereas, phosgene, names, prefe. Diphosgene is an organic chemical compound with the formula ClCO2CCl3 This colorless liquid is a valuable reagent in the synthesis of organic compounds Diphosgene is related to phosgene and has comparable toxicity but is more conveniently handled because it is a liquid whereas phosgene is a gas Diphosgene Names Preferred IUPAC name Trichloromethyl carbonochloridate Other names Trichloromethyl chloroformate surpalite Identifiers CAS Number 503 38 8 Y 3D model JSmol Interactive image ChemSpider 21154424 Y ECHA InfoCard 100 007 242 EC Number 207 965 9 PubChem CID 10426 RTECS number LQ7350000 UNII PO4Q4R80LV CompTox Dashboard EPA DTXSID60862065 InChI InChI 1S C2Cl4O2 c3 1 7 8 2 4 5 6 YKey HCUYBXPSSCRKRF UHFFFAOYSA N YInChI 1 C2Cl4O2 c3 1 7 8 2 4 5 6Key HCUYBXPSSCRKRF UHFFFAOYAO SMILES ClC O OC Cl Cl Cl Properties Chemical formula C2Cl4O2 Molar mass 197 82 g mol Appearance liquid at room temperature Density 1 65 g cm3 Melting point 57 C 71 F 216 K Boiling point 128 C 262 F 401 K Solubility in water insoluble reacts Hazards Occupational safety and health OHS OSH Main hazards highly toxic maybe corrosive asphyxiant GHS labelling Pictograms Signal word Danger Hazard statements H300 H301 H314 H330 Precautionary statements P260 P264 P270 P271 P280 P284 P301 P310 P301 P330 P331 P303 P361 P353 P304 P340 P305 P351 P338 P310 P320 P321 P330 P363 P403 P233 P405 P501 Flash point 32 C 90 F 305 K Related compounds Related compounds COCl2 Cl2 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Production and uses 2 Role in warfare 3 Safety 4 See also 5 References 6 External linksProduction and uses editDiphosgene is prepared by radical chlorination of methyl chloroformate under UV light 1 Cl CO OCH3 3 Cl2 hv Cl CO OCCl3 3 HCl Another method is the radical chlorination of methyl formate 2 H CO OCH3 4 Cl2 hv Cl CO OCCl3 4 HCl Diphosgene converts to phosgene upon heating or upon catalysis with charcoal It is thus useful for reactions traditionally relying on phosgene For example it convert amines into isocyanates secondary amines into carbamoyl chlorides carboxylic acids into acid chlorides and formamides into isocyanides Diphosgene serves as a source of two equivalents of phosgene 2 RNH2 ClCO2CCl3 2 RNCO 4 HCl With a amino acids diphosgene gives the acid chloride isocyanates OCNCHRCOCl or N carboxy amino acid anhydrides depending on the conditions 3 It hydrolyzes to release HCl in humid air Diphosgene is used in some laboratory preparations because it is easier to handle than phosgene Role in warfare editDiphosgene was originally developed as a pulmonary agent for chemical warfare a few months after the first use of phosgene It was used as a poison gas in artillery shells by Germany during World War I The first recorded battlefield use was in May 1916 4 Diphosgene was developed because the vapors could destroy the filters in gas masks in use at the time Safety editDiphosgene has a relatively high vapor pressure of 10 mm Hg 1 3 kPa at 20 C and decomposes to phosgene around 300 C Exposure to diphosgene is similar in hazard to phosgene See also editPhosgene Triphosgene CarbonyldiimidazoleReferences edit Keisuke Kurita and Yoshio Iwakura 1979 Trichloromethyl Chloroformate as a Phosgene Equivalent 3 Isocyanatopropanoyl Chloride Organic Syntheses 59 195 Collected Volumes vol 6 p 715 Lohs K H Synthetische Gifte Berlin east 1974 German Kurita K Trichloromethyl Chloroformate in Encyclopedia of Reagents for Organic Synthesis Ed L Paquette 2004 J Wiley amp Sons New York doi 10 1002 047084289X Jones Simon Hook Richard 2007 World War I Gas Warfare Tactics and Equipment Osprey Publishing ISBN 978 1 84603 151 9 External links editmedical care guide NATO guide includes treatment advice material safety data sheet PDF for phosgene and diphosgene treated as one MSDS for diphosgene specifically Retrieved from https en wikipedia org w index php title Diphosgene amp oldid 1210435579, wikipedia, wiki, book, books, library,
