Under the appropriate conditions it undergoes hazardous reactions with Al, tert-butyl azido formate, 2,4-hexadiyn-1,6-diol, isopropyl alcohol, K, Na, sodium azide, hexafluoroisopropylideneamino lithium, lithium. When heated to decomposition or on contact with water or steam it will react to produce toxic and corrosive fumes of CO and Cl−. Caution: Arrangements should be made for monitoring its use.
Analytical Methods:
For occupational chemical analysis use OSHA: #ID-61.
Conditions | Yield |
---|---|
With catalyst: charcoal in laboratorium, at ambient temp., in a glas tube filled with charcoal; | 100% |
pyrographite at 40 - 85℃; under 1050.11 - 5250.53 Torr; Product distribution / selectivity; Continuous process; | |
pyrographite at 45 - 93.5℃; under 1500.15 - 3750.38 Torr; Shell-and-tube reactor; |
bis(trichloromethyl) carbonate
A
tetrachloromethane
B
phosgene
C
carbon dioxide
Conditions | Yield |
---|---|
With copper phthalocyanine at 90℃; for 0.583333h; Mechanism; Reagent/catalyst; Temperature; Time; | A n/a B 100% C n/a |
2,2,3,3,4,4,5,5-octafluoropentan-1-ol
bis(trichloromethyl) carbonate
A
phosgene
B
2,2,3,3,4,4,5,5-octafluoropentyl chloroformate
C
bis(2,2,3,3,4,4,5,5-octafluoropentyl) carbonate
Conditions | Yield |
---|---|
Stage #1: bis(trichloromethyl) carbonate With pyridine In pentane at -15℃; for 1h; Stage #2: 2,2,3,3,4,4,5,5-octafluoropentan-1-ol In pentane at -15℃; for 6h; | A n/a B 95% C 5% |
bis(trichloromethyl) carbonate
(2,3,4,5,6-pentafluorophenyl)methanol
A
phosgene
B
2,3,4,5,6-pentafluorobenzyl chloroformate
Conditions | Yield |
---|---|
Stage #1: bis(trichloromethyl) carbonate With pyridine In pentane at -15℃; for 1h; Stage #2: (2,3,4,5,6-pentafluorophenyl)methanol In pentane at -15 - 0℃; for 6h; | A n/a B 92% C 8% |
Conditions | Yield |
---|---|
With water; antimony(V) chloride In water reaction at 60°C on addn. of 0.1 mol SbCl5;; | 90% |
With water; Gallium trichloride In water reaction at 60°C on addn. of 0.1 mol GaCl3;; | 89% |
With air; fired clay fragments |
bis(trichloromethyl) carbonate
2-(pentafluorophenoxy)ethanol
A
phosgene
Conditions | Yield |
---|---|
Stage #1: bis(trichloromethyl) carbonate With pyridine In pentane at -15℃; for 1h; Stage #2: 2-(pentafluorophenoxy)ethanol In pentane at -15 - 20℃; for 6h; | A n/a B 86% C 11% |
tert-butyl 2-bromopropionate
ethylene dibromide
phosgene
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; ammonium chloride In tetrahydrofuran | 73% |
Conditions | Yield |
---|---|
With sulfur dioxide In neat (no solvent) reaction of CCl4 with SO2 on heating to 200°C;; | A n/a B 72% |
Conditions | Yield |
---|---|
With CO In thionyl chloride AuCl3 suspended in SOCl2 under N2, reaction flask evacuated, filled with CO at atm. pressure, stirred at 20.1°C until Au2Cl6 disappeared(36 h); filtration, drying in vac.; | A n/a B 67% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane In tetrahydrofuran | 63% |
oxalyl dichloride
ethanedinitrile
A
phosgene
B
carbon dioxide
C
2,3,7,8-tetrachloro-5H,10H-diimidazo<1,2-a:1',2'-d>pyrazine-5,10-dione
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogenchloride; NR4Cl (Adogen) In dichloromethane at 70 - 120℃; for 72h; Further byproducts given; | A n/a B n/a C 60% |
iron pentacarbonyl
phosgene
Conditions | Yield |
---|---|
With tetrachloromethane; oxygen In tetrachloromethane Irradiation (UV/VIS); Irradiation λ >350 nm, CCl4 satd. with dry air;; detected by IR sepctra;; | 50% |
Conditions | Yield |
---|---|
In neat (no solvent) condensing HCl onto N,N'-carbonyldiimidazole at -196°C, warming to -63°C, condensing excess HCl into a trap held at -196°C; contains some HCl; | 49.8% |
Conditions | Yield |
---|---|
In dichloromethane N2-atmosphere; slight molar excess of Au(I), 1.5 h; | A n/a B 42% |
In thionyl chloride N2-atmosphere; molar ratio Au(III):Au(I)=3:1 to 1:1, 3-28 h; filtration (under Ar), drying (vac.); elem. anal.; yield depending on molar ratio of educts, amt. of solvent and reaction time; | A n/a B 24% |
tetrafluorohydrazine
oxalyl dichloride
A
phosgene
B
chlorodifluoroamine
C
dinitrogen difluoride
D
fluoroformyl chloride
E
difluorocarbamoyl chloride
Conditions | Yield |
---|---|
other Radiation; UV photolysis, 6h, ratio of educts: (ClCO)2 112 Torr, N2F4 168 Torr; fractionated condensation, gaschromy.; | A n/a B n/a C n/a D n/a E 40% |
other Radiation; UV photolysis, 6h, ratio of educts: (ClCO)2 112 Torr, N2F4 168 Torr; fractionated condensation, gaschromy.; | A n/a B n/a C n/a D n/a E 40% |
perfluoro(N,N-diethylcarbamoyl fluoride)
A
tetrachloromethane
B
phosgene
Conditions | Yield |
---|---|
With aluminium trichloride at 100℃; for 100h; | A 0.03 g B 0.02 g C 38.7% |
Conditions | Yield |
---|---|
With chlorine at 510 - 700℃; | A 35% B n/a |
Conditions | Yield |
---|---|
Irradiation (UV/VIS); with Cl2 sensibilized photochemical oxidn., 80 to 100°C; | A 20% B n/a |
Chlorodifluoromethane
A
phosgene
B
Carbonyl fluoride
C
fluoroformyl chloride
Conditions | Yield |
---|---|
With oxygen for 0.5 - 4.5h; Product distribution / selectivity; UV-irradiation (500 W); | A 0.04% B 15.6% C 0.24% |
pyridine
bis(trichloromethyl) oxalate
chlorobenzene
A
phosgene
B
oxalyl dichloride
Conditions | Yield |
---|---|
With chlorine monoxide |
Conditions | Yield |
---|---|
With aluminium trichloride |
Conditions | Yield |
---|---|
With aluminium trichloride |
tetrachloromethane
(4-nitro-phenyl)-carbamic acid trichloromethyl ester
A
phosgene
B
4-Nitrophenyl isocyanate
tetrachloromethane
methylammonium carbonate
phosgene
Conditions | Yield |
---|---|
With pumice stone at 350℃; |
tetrachloromethane
A
phosgene
B
methylammonium carbonate
Conditions | Yield |
---|---|
With zinc(II) oxide at 200℃; |
Conditions | Yield |
---|---|
With ozone | |
In gas byproducts: Cl; Irradiation (UV/VIS); with Cl2 sensibilized photochemical oxidn.; |
phosgene
Conditions | Yield |
---|---|
bei laengerem Aufbewahren; |
Conditions | Yield |
---|---|
With air | |
With oxygen | |
an der Luft; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 3h; Inert atmosphere; | 100% |
With triethylamine In tetrahydrofuran at 0℃; | 74% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 40℃; for 1.5h; | 100% |
In tetrahydrofuran at 40℃; for 5h; | 99.7% |
In tetrahydrofuran; toluene at 50 - 60℃; for 4h; | 96% |
phosgene
2-(4-nitrophenyl)ethanol
2-(4-nitrophenyl)ethoxycarbonyl chloride
Conditions | Yield |
---|---|
In dichloromethane; toluene 1.) r.t., 1 h; 2.) 50 deg C, 5 h; | 100% |
In dichloromethane; toluene for 1h; Ambient temperature; | 98% |
phosgene
2,4,6-tri-tert-butylphenoxol
2,4,6-tri(tert-butyl)phenyl carbonochloridate
Conditions | Yield |
---|---|
With n-butyllithium at 0℃; | 100% |
With n-butyllithium In 1,2-dimethoxyethane at 0℃; | 98% |
Stage #1: 2,4,6-tri-tert-butylphenoxol With sodium hydride In tetrahydrofuran Metallation; Stage #2: phosgene With N,N-dimethyl-aniline In toluene at 0 - 20℃; for 2.5h; Acylation; | 75% |
Conditions | Yield |
---|---|
In tetrahydrofuran; toluene at 20℃; for 18h; | 100% |
In tetrahydrofuran; toluene for 21h; Esterification; | 99% |
In 1,4-dioxane for 24h; Ambient temperature; |
Conditions | Yield |
---|---|
With pyridine In chloroform at 23℃; for 17h; | 100% |
phosgene
(2S,3R,4S)-1-amino-4-<<(tertbutyloxy)carbonyl>amino>-5-cyclohexyl-2-hydroxy-3-(methoxymethoxy)pentane
(1'R,2'S,5S)-5-<2'-<<(tertbutyloxy)carbonyl>amino>-3'-cyclohexyl-1'-(methoxymethoxy)propyl>oxazolidin-2-one
Conditions | Yield |
---|---|
With triethylamine In dichloromethane; toluene 1.) a) 0 deg C, 1 h, b) RT, 1 h; | 100% |
phosgene
(-)-8-phenylmenthol
(1R,2S,5R)-(-)-8-phenylmenthyl chloroformate
Conditions | Yield |
---|---|
With quinoline In toluene for 16h; Ambient temperature; | 100% |
With quinoline In toluene at 0 - 20℃; for 16.5h; | |
With quinoline In toluene at 0 - 20℃; for 16.5h; |
phosgene
2-(1-methyl-1-p-phenoxyphenylethyl)-5-methylcyclohexanol
(1R,2S,5R)-8-(4-phenoxyphenyl)menthyl chloroformate
Conditions | Yield |
---|---|
With quinoline In toluene for 16h; Ambient temperature; | 100% |
phosgene
methyl 4-(2-hydroxyethyl)-3-nitrobenzoate
2-(4-(methoxycarbonyl)-2-nitrophenyl)ethyl chloroformate
Conditions | Yield |
---|---|
100% | |
In dichloromethane; toluene a) 4 deg C, 30 min, b) room temperature, 3 h; | 87% |
phosgene
2,4,5-Trichlorophenyl 4'-(2-hydroxyethyl)-3'-nitrobenzoate
C16H9Cl4NO6
Conditions | Yield |
---|---|
100% | |
In dichloromethane; toluene a) 4 deg C, 30 min., b) room temperature, 3 h; | 92% |
phosgene
2-Oxa-3-azabicyclo<2.2.2>oct-5-ene hydrochloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 12h; | 100% |
phosgene
[1-Phenyl-1-(3H-[1,2,3]triazol-4-yl)-meth-(Z)-ylidene]-hydrazine
4-phenyl-6H-<1,2,3>triazolo<1,5-d><1,2,4>triazin-7-one
Conditions | Yield |
---|---|
In 1,4-dioxane; toluene for 5h; Ambient temperature; | 100% |
phosgene
N-(pyridin-2-yl)-1H-benzo[d]imidazol-2-amine
Conditions | Yield |
---|---|
With triethylamine In toluene for 6h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With pyridine In toluene at 0℃; for 1h; | 100% |
Conditions | Yield |
---|---|
In ethyl acetate at 45℃; | 100% |
phosgene
(2S,3S)-Dimethyl N-(9'-phenylfluoren-9'-yl)-3-hydroxyaspartate
(4S,5S)-2-Oxo-3-(9-phenyl-9H-fluoren-9-yl)-oxazolidine-4,5-dicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With pyridine; dmap In toluene at 75℃; for 0.416667h; | 100% |
phosgene
(Z)-(R)-9-Benzylamino-3,4,5,6,9,10-hexahydro-thiecin-2-one
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 3.5h; | 100% |
phosgene
(4S,5S)-4-[(3R,3aR,5aS,6R,7R,9aS,9bS)-6-(2,2-Dimethoxy-ethyl)-3-((R)-1,5-dimethyl-hexyl)-3a,6-dimethyl-dodecahydro-cyclopenta[a]naphthalen-7-yl]-6,6,8-trimethyl-1,3-dioxa-spiro[4.5]decane-2,7-dione
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0℃; | 100% |
With pyridine In dichloromethane at 0℃; Yield given; |
phosgene
Conditions | Yield |
---|---|
In dichloromethane; toluene at 0℃; for 3h; | 100% |
phosgene
12,14-diaminodehydroabietic acid methyl ester
(1R,4aS,10aR)-6,8-Diisocyanato-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester
Conditions | Yield |
---|---|
In toluene for 0.5h; Ambient temperature; | 100% |
2,3;4,5-di-O-isopropylidene-β-D-fructopyranose
phosgene
2,3:4,5-di-O-isopropylidene-β-D-fructopyranose-10-chloroformate
Conditions | Yield |
---|---|
In diethyl ether; toluene Ambient temperature; | 100% |
phosgene
2-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]phenylamine
tert-butyl(2-isocyanatobenzyloxy)dimethylsilane
Conditions | Yield |
---|---|
In toluene at 110℃; | 100% |
In toluene at 60℃; for 1h; |
phosgene
(2-Cyano-ethyl)-(2-phenylamino-ethyl)-carbamic acid tert-butyl ester
C17H22ClN3O3
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In dichloromethane; water; toluene for 0.5h; Acylation; | 100% |
phosgene
Conditions | Yield |
---|---|
With TEA In dichloromethane | 100% |
phosgene
Conditions | Yield |
---|---|
With TEA In dichloromethane | 100% |
phosgene
(9H-fluoren-9-yl)methyl1-methylhydrazinecarboxylate
2-(chlorocarbonyl)-1-Fmoc-methylhydrazine
Conditions | Yield |
---|---|
In 1,4-dioxane at 10 - 20℃; Acylation; | 100% |
phosgene
(9H-fluoren-9-yl)methyl 2-methylhydrazine-1-carboxylate
1-chlorocarbonyl-2-(9H-fluoren-9-methoxycarbonylamino)-1-methylhydrazine
Conditions | Yield |
---|---|
In 1,4-dioxane at 10 - 20℃; Acylation; | 100% |
With sodium hydrogencarbonate In dichloromethane; water for 0.5h; | 97% |
With sodium hydrogencarbonate In dichloromethane; water; toluene for 0.5h; | 97% |
In 1,4-dioxane; toluene at 20℃; for 2h; | |
In dichloromethane; toluene at 0℃; |
Conditions | Yield |
---|---|
With pyridine In diethyl ether; toluene at -78 - 20℃; Acylation; | 100% |
phosgene
[2,7-di-(tert-butyl)-9H-fluoren-9-yl]methanol
2,7-di-tert-butyl-9-fluorenylmethoxycarbonyl chloride
Conditions | Yield |
---|---|
In dichloromethane; toluene at 20℃; for 72h; chloroacylation; | 100% |
In toluene |
Uses of phosgene(75-44-5) include the manufacture of toluene diisocyanate, methylone diisocyanate, and polycarbonate resins.
Phosgene(75-44-5) is manufactured by reacting chlorine gas and carbon monoxide in the presence of activated carbon.
CO + Cl2 → O=CCl2
1. | ihl-hmn LC50:3200 mg/m3 | SCJUAD Science Journal. 4 (1967),33. | ||
2. | ihl-hmn TCLo:25 ppm/30M:PUL | 29ZWAE Practical Toxicology of Plastics Lefaux, R.,Cleveland, OH.: Chemical Rubber Company,1968,207. | ||
3. | ihl-man LCLo:360 mg/m3/30M | 85GMAT Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,99. | ||
4. | ihl-mam LCLo:50 ppm/5M | AEPPAE Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 138 (1928),65. | ||
5. | ihl-cat LCLo:190 mg/m3/15M | 85GMAT Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,99. | ||
6. | ihl-uns LCLo:50 ppm/5M | AEPPAE Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 138 (1928),65. | ||
7. | ihl-uns LCLo:11 mg/m3/30M | TABIA2 Tabulae Biologicae. 3 (1933),231. |
Under the appropriate conditions it undergoes hazardous reactions with Al, tert-butyl azido formate, 2,4-hexadiyn-1,6-diol, isopropyl alcohol, K, Na, sodium azide, hexafluoroisopropylideneamino lithium, lithium. When heated to decomposition or on contact with water or steam it will react to produce toxic and corrosive fumes of CO and Cl−. Caution: Arrangements should be made for monitoring its use.
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