Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 2h; | 99% |
With sodium hydroxide In dichloromethane at 20℃; for 2h; | 88.4% |
Stage #1: bis(trichloromethyl) carbonate With sodium carbonate; N,N-dimethyl-formamide In toluene at 0℃; for 0.5h; Stage #2: phenol In toluene at 0℃; for 8.5h; | 66% |
Conditions | Yield |
---|---|
With CoCl2 In triphenylphosphine | 91.5% |
With water Behandeln mit Phosgen und Trichloraethylen; |
Conditions | Yield |
---|---|
91% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 100℃; Temperature; | 89.4% |
With sodium hydroxide; water; toluene at 30℃; bis:>40 degreeC.; | |
With N,N-dimethyl-aniline; benzene |
5-tert-Butoxycarbonylamino-3-methyl-thiophene-2-carboxylic acid ethyl ester
phenyl chloroformate
Conditions | Yield |
---|---|
Stage #1: 5-tert-Butoxycarbonylamino-3-methyl-thiophene-2-carboxylic acid ethyl ester With trifluoroacetic acid In dichloromethane at 0℃; for 2h; Stage #2: With sodium hydroxide; water In ethyl acetate Product distribution / selectivity; | 89% |
S-methyl O-phenyl carbonothioate
phenyl chloroformate
Conditions | Yield |
---|---|
With sulfuryl dichloride at 20℃; for 1h; | 78% |
Conditions | Yield |
---|---|
at 30℃; | |
With toluene |
carbonic acid phenyl ester-trichloromethyl ester
A
phosgene
B
phenyl chloroformate
Conditions | Yield |
---|---|
at 180 - 210℃; |
Conditions | Yield |
---|---|
at 140 - 150℃; im geschlossenen Rohr; | |
at 140 - 150℃; |
Conditions | Yield |
---|---|
With water |
1-trifluoromethoxybenzene
A
bis(phenyl) carbonate
B
phenyl fluoroformate
C
phenyl chloroformate
D
phenol
Conditions | Yield |
---|---|
With aluminium trichloride In fluorobenzene at 90℃; for 0.0833333h; |
3-chloro-3-phenyl-3H-diazirine
A
benzoyl chloride
B
phenyl chloroformate
Conditions | Yield |
---|---|
With oxygen In solid matrix at -263.2℃; Irradiation; |
3-chloro-3-phenyl-3H-diazirine
A
carbon dioxide
B
carbon monoxide
C
chlorophenyldiazomethane
D
benzoyl chloride
E
phenyl chloroformate
F
1-chlorocyclohepta-1,2,4,6-tetraene
Conditions | Yield |
---|---|
With oxygen In solid matrix at -263.2℃; Product distribution; Mechanism; Irradiation; different O2 concentrations and wavelengths of irradiation; |
water
phenol
trichloromethyl chloroformate
phenyl chloroformate
Conditions | Yield |
---|---|
Reaktion von Natriumphenolat (2 Mol); |
trichloromethyl chloroformate
A
bis(phenyl) carbonate
B
phenyl chloroformate
Conditions | Yield |
---|---|
je nach den angewandten Mengenverhaeltnissen; |
3-chloro-3-phenyl-3H-diazirine
A
benzoyl chloride
B
chlorobenzene
C
phenyl chloroformate
Conditions | Yield |
---|---|
With oxygen at -247.2℃; under 150 - 200 Torr; Product distribution; Mechanism; Irradiation; study of the oxygen trapping of phenylchlorocarbene intermediate formed from phenylchlorodiazirine in oxigen-doped matrix by irradiation, mechanism is discussed; |
Conditions | Yield |
---|---|
With pyrographite; triethylamine In tetrahydrofuran at 120℃; for 3h; Condensation; | |
With dmap In toluene at 20℃; for 24h; | |
With dmap In toluene at 20℃; for 24h; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: DBU / tetrahydrofuran / 1 h / 20 °C / 750.06 Torr 1.2: 25 percent / tetrahydrofuran / 2 h / 20 °C / 750.06 Torr 2.1: 78 percent / SO2Cl2 / 1 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: S; DBU / tetrahydrofuran / 6 h / 80 °C / 7500.6 Torr 1.2: 49 percent / tetrahydrofuran / 16 h / 20 °C / 750.06 Torr 2.1: 78 percent / SO2Cl2 / 1 h / 20 °C View Scheme |
phosgene
hypophosphorous acid
phenol
A
bis(phenyl) carbonate
B
phenyl chloroformate
Conditions | Yield |
---|---|
In Diphenylmethane |
phenyl oxalyl chloride
2-amino-5-trifluoromethyl-1,3,4-thiadiazole
phenyl chloroformate
Conditions | Yield |
---|---|
With triethylamine | |
With triethylamine |
phenyl carbonic acid
phenyl chloroformate
Conditions | Yield |
---|---|
With thionyl chloride for 2h; Reflux; Cooling with ice; | |
With thionyl chloride In toluene for 1h; Reflux; |
2-oxo-2-(pyren-1-yl)ethyl phenyl carbonate
phenyl chloroformate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: water / acetonitrile / pH 7.5 / Photolysis; Inert atmosphere 2: sodium carbonate / toluene / 6 h / 0 °C View Scheme |
4-methoxy-aniline
phenyl chloroformate
(4-methoxyphenyl)carbamic acid phenyl ester
Conditions | Yield |
---|---|
With pyridine In ethyl acetate at 20℃; for 1h; | 100% |
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 0.0833333h; | 97% |
With sodium carbonate In tetrahydrofuran; water; ethyl acetate at 0 - 20℃; | 92% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 23℃; for 4h; Inert atmosphere; | 100% |
With pyridine In dichloromethane for 3h; | 90% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 3h; | 100% |
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h; | 100% |
With triethylamine In dichloromethane at 0℃; for 0.5h; | 100% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 16h; Inert atmosphere; | 100% |
With pyridine In dichloromethane at 23℃; Cooling with ice; Inert atmosphere; | 99% |
With pyridine; dmap In dichloromethane at 0 - 20℃; for 13.5h; | 95% |
benzoic acid hydrazide
phenyl chloroformate
1-benzoyl-2-phenoxycarbonylhydrazine
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran 1) -10 deg C, 30 min, 2) 1 h, room temperature; | 100% |
In benzene |
1-methyl-1-phenylethyl alcohol
phenyl chloroformate
2-phenylisopropyloxycarbonyl phenyl carbonate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -5 - 0℃; | 100% |
With pyridine In dichloromethane |
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 20℃; for 1h; | 100% |
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 0℃; for 2h; | 75% |
With sodium hydride In N,N-dimethyl-formamide at 70℃; for 20h; | 52% |
6,7-Dimethoxy-1-(3-pentyl)-3,4-dihydroisoquinoline
phenyl chloroformate
Phenyl 6,7-Dimethoxy-1-(3-pentylidene)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane; benzene Heating; | 100% |
2-hydroxy-2-methylpropanenitrile
phenyl chloroformate
1-cyano-1-methyl-ethylphenylcarbonate
Conditions | Yield |
---|---|
With pyridine for 0.5h; | 100% |
L-valine
phenyl chloroformate
(2S)-3-Methyl-2-(phenoxycarbonyl)aminobutyric acid
Conditions | Yield |
---|---|
With sodium hydroxide; potassium hydrogencarbonate for 1.5h; Ambient temperature; | 100% |
With aluminum oxide; lithium chloride; lithium hydroxide In water at -20 - -10℃; for 5h; pH=9.5 - 10.2; Schotten-Baumann Reaction; Inert atmosphere; | 92% |
Stage #1: L-valine; phenyl chloroformate With sodium hydroxide In water at 0℃; for 5h; Stage #2: With hydrogenchloride In water pH=2; | 75.9% |
2,2,2-trifluoroethanol
phenyl chloroformate
2,2,2-trifluoroethyl phenyl carbonate
Conditions | Yield |
---|---|
With pyridine | 100% |
With pyridine In dichloromethane at 20℃; for 1h; |
4-(Tetradecyloxy)-benzyl alcohol
phenyl chloroformate
phenyl <4-(tetradecyloxy)phenyl>methyl carbonate
Conditions | Yield |
---|---|
With pyridine In dichloromethane 1.) 0 deg C, 15 min, 2.) RT, 30 min; | 100% |
With pyridine In dichloromethane |
(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane
phenyl chloroformate
Conditions | Yield |
---|---|
With pyridine In dichloromethane | 100% |
2'-methyl-2',3'-dihydrospiro
phenyl chloroformate
N-phenoxycarbonyl-2',3'-dihydrospiro
Conditions | Yield |
---|---|
In dichloromethane Ambient temperature; overnight; | 100% |
In dichloromethane; ethyl acetate | 2.6 g (69.7%) |
4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenylamine
phenyl chloroformate
phenyl (4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 100% |
With pyridine In dichloromethane at 0 - 20℃; for 2h; | 92.1% |
With pyridine for 3h; | 90% |
phenyl chloroformate
3-O-<<2-(dimethylamino)ethyl>carbamoyl>-2-O-methyl-1-O-(octadecylcarbamoyl)glycerol
3-O--N-(phenoxycarbonyl)carbamoyl>-2-O-methyl-1-O-(octadecylcarbamoyl)glycerol
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 4h; Ambient temperature; | 100% |
(trimethylsilyl)ethynylmagnesium bromide
phenyl chloroformate
Conditions | Yield |
---|---|
In dichloromethane at -20℃; | 100% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 22℃; | 100% |
phenyl chloroformate
(R)-2-((R)-2-Methyl-pent-4-enyl)-2,3-dihydro-1H-pyridin-4-one
(R)-2-((R)-2-Methyl-pent-4-enyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid phenyl ester
Conditions | Yield |
---|---|
With n-butyllithium | 100% |
Stage #1: (R)-2-((R)-2-Methyl-pent-4-enyl)-2,3-dihydro-1H-pyridin-4-one With n-butyllithium Inert atmosphere; Stage #2: phenyl chloroformate Inert atmosphere; | 100% |
phenyl chloroformate
3-amino-6-(3-pyridyl)pyridine
[2,3']bipyridinyl-5-yl-carbamic acid phenyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 18h; Condensation; | 100% |
phenyl chloroformate
2-chloro-3-(3-pyridyl)aniline
(2-chloro-3-pyridin-3-yl-phenyl)-carbamic acid phenyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 18h; Condensation; | 100% |
phenyl chloroformate
3-(4-methyl-3-pyridyl)aniline
[3-(4-methyl-pyridin-3-yl)-phenyl]-carbamic acid phenyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 18h; Condensation; | 100% |
phenyl chloroformate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 18h; Condensation; | 100% |
phosphonic acid diethyl ester
phenyl chloroformate
phenyl diethoxyphosphorylformate
Conditions | Yield |
---|---|
at 120℃; for 1.5h; | 100% |
phenyl chloroformate
1-amino-6,8-dimethoxy-3,4-dihydroquinolin-2(1H)-one
phenyl (6,8-dimethoxy-2-oxo-1,2,3,4-tetrahydroquinolin-1-yl)carbamate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In dichloromethane at 20℃; | 100% |
phenyl chloroformate
trans-2-(2-Vinylstyryl)pyrrole
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutyl-ammonium chloride In dichloromethane for 0.25h; | 100% |
phenyl chloroformate
3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine
[5-tert-butyl-2-(4-methylphenyl)-2H-pyrazol-3-yl]carbamic acid phenyl ester
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 100% |
With sodium hydroxide In water; ethyl acetate at 10.9 - 25.5℃; for 1h; | 95% |
With sodium carbonate In Isopropyl acetate; water at 20℃; | 88% |
phenyl chloroformate
(3R,4S,5S,6R)-4-((E)-1,5-Dimethyl-hexa-1,4-dienyl)-5-methoxy-1-oxa-spiro[2.5]octan-6-ol
Conditions | Yield |
---|---|
With dmap In dichloromethane at 0℃; | 100% |
phenyl chloroformate
1-((3R,4S,5S,6R)-6-Hydroxy-5-methoxy-1-oxa-spiro[2.5]oct-4-yl)-ethanone O-benzyl-oxime
Conditions | Yield |
---|---|
With dmap In dichloromethane at 0℃; | 100% |
2-thioxo-3H-1,3-benzothiazole
phenyl chloroformate
S-(1,3-benzothiazol-2-yl) O-phenyl thiocarbonate
Conditions | Yield |
---|---|
With triethylamine In benzene at 20℃; for 1h; | 100% |
The Phenyl chlorocarbonate, with the CAS registry number 1885-14-9 and EINECS registry number 217-547-8, has the systematic name of phenyl carbonochloridate. And the molecular formula of this chemical is C16H36ClN. It is a kind of clear liquid with a strong odor, and belongs to the following product categories: Miscellaneous; Organics; Chloroformates. In addition, it is sensitive to moisture, and should be stored in the refrigerator. Besides, it is used as reagents for organic synthesis.
The physical properties of Phenyl chlorocarbonate are as following: (1)ACD/LogP: 2.66; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.66; (4)ACD/LogD (pH 7.4): 2.66; (5)ACD/BCF (pH 5.5): 62.02; (6)ACD/BCF (pH 7.4): 62.02; (7)ACD/KOC (pH 5.5): 667.87; (8)ACD/KOC (pH 7.4): 667.87; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.532; (14)Molar Refractivity: 37.81 cm3; (15)Molar Volume: 121.9 cm3; (16)Polarizability: 14.98×10-24cm3; (17)Surface Tension: 40.4 dyne/cm; (18)Density: 1.283 g/cm3; (19)Flash Point: 79 °C; (20)Enthalpy of Vaporization: 42.28 kJ/mol; (21)Boiling Point: 186.5 °C at 760 mmHg; (22)Vapour Pressure: 0.66 mmHg at 25°C.
Preparation of Phenyl chlorocarbonate: It can be prepared by phenol and phosgene. Dissolve phenol in chloroform, and then pass phosgene. Dilute with water after addition of equimolar N,N-Dimethylaniline. Wash the oil layer with diluted hydrochloric acid and water, and then dry with anhydrous calcium chloride. Heat to get rid of chloroform, and collect the distillate in 74-75°C(1.73kPa) after reduced pressure distillation. The distillate is the product you desired. And the yield is 90%.
Uses of Phenyl chlorocarbonate: It can react with phenylhydrazine to produce 3-phenyl-carbazic acid phenyl ester. This reaction will need solvents diethyl ether and tetrahydrofuran. The reaction time is 0.5 hours with heating, and the yield is about 32%.
You should be cautious while dealing with this chemical. If contact with water, it will liberate toxic gas. It irritates skin, and has risk of serious damage to eyes. It is very toxic by inhalation, and may also cause burns. In addition, it is harmful if swallowed. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer); In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(Cl)Oc1ccccc1
(2)InChI: InChI=1/C7H5ClO2/c8-7(9)10-6-4-2-1-3-5-6/h1-5H
(3)InChIKey: AHWALFGBDFAJAI-UHFFFAOYAM
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LC | inhalation | > 800mg/m3/10M (800mg/m3) | National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. NDCrc-132, Pg. Dec, 1942. | |
rabbit | LD50 | skin | 3970uL/kg (3.97mL/kg) | American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969. | |
rat | LCLo | inhalation | 44ppm/4H (44ppm) | American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969. | |
rat | LD50 | oral | 1410uL/kg (1.41mL/kg) | American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969. |
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