4-bromobenzenecarbonitrile
4-cyanobenzenethiol
Conditions | Yield |
---|---|
Stage #1: 4-bromobenzenecarbonitrile With caesium carbonate; copper(II) sulfate In dimethyl sulfoxide for 0.166667h; Inert atmosphere; Stage #2: With ethane-1,2-dithiol In dimethyl sulfoxide at 100℃; for 20h; Inert atmosphere; | 100% |
With copper(ll) sulfate pentahydrate; caesium carbonate; ethane-1,2-dithiol In dimethyl sulfoxide at 110℃; for 20h; Inert atmosphere; | 87% |
Multi-step reaction with 2 steps 1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine / toluene / 14 h / 120 °C / Inert atmosphere 2: sodium methylate / methanol; mineral oil / 14 h / 0 - 20 °C View Scheme | |
Stage #1: 4-bromobenzenecarbonitrile With TurboGrignard In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; Stage #2: With sulfur In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; |
4-iodobenzonitrile
4-cyanobenzenethiol
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; caesium carbonate; ethane-1,2-dithiol In dimethyl sulfoxide at 90℃; for 20h; Inert atmosphere; | 93% |
With copper(l) iodide; thiourea; L-proline; sodium t-butanolate In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere; | 90% |
4-mercaptobenzamide
4-cyanobenzenethiol
Conditions | Yield |
---|---|
With trichlorophosphate In N,N-dimethyl-formamide at 0℃; for 2h; | 93% |
A
triphenylmethane
B
4-cyanobenzenethiol
Conditions | Yield |
---|---|
With 2-methyl-N-cyclohexylpropanamide In N,N-dimethyl-formamide Mechanism; Rate constant; Thermodynamic data; electrolyse (Hg pool electrode); ΔG(excit.)0; other reagents (azobenzenes) with other electrode; | A 84% B 90% C 6% |
4-cyanophenyl-S,N,N-dimethyl thiocarbamate
4-cyanobenzenethiol
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 3h; | 84% |
With potassium hydroxide In tetrahydrofuran; methanol for 3h; Ambient temperature; | 81% |
With potassium hydroxide In methanol |
4-(benzylsulfanyl)benzonitrile
4-cyanobenzenethiol
Conditions | Yield |
---|---|
With aluminum (III) chloride In benzene at 20℃; for 144h; Inert atmosphere; | 76% |
4-fluorobenzonitrile
A
4-cyanobenzenethiol
B
bis(4-cyanophenyl)disulfane
C
bis(4-cyanophenyl)sulfide
Conditions | Yield |
---|---|
With potassium sulfide In N,N-dimethyl-formamide at 50 - 55℃; for 21h; | A 5% B 73% C 9.5% |
With potassium sulfide In N,N-dimethyl-formamide at 50 - 55℃; for 21h; | A 5% B 73% C 9.5% |
With potassium sulfide In N,N-dimethyl-formamide at 50 - 55℃; for 21h; | A 5% B 73% C 9.5% |
4-fluorobenzonitrile
4-cyanobenzenethiol
Conditions | Yield |
---|---|
Stage #1: 4-fluorobenzonitrile With sodium sulfide In N,N-dimethyl-formamide at 20℃; for 36h; Inert atmosphere; Stage #2: With hydrogenchloride; zinc In water Cooling with ice; Inert atmosphere; | 46% |
Stage #1: 4-fluorobenzonitrile With sodium sulfide In N,N-dimethyl-formamide at 20℃; Stage #2: With hydrogenchloride; zinc In water at 0℃; for 1h; | 18.2% |
4-Cyanochlorobenzene
thiourea
A
4-cyanobenzenethiol
B
bis(4-cyanophenyl)disulfane
C
bis(4-cyanophenyl)sulfide
Conditions | Yield |
---|---|
With 4,4'-bipyridine; potassium tert-butylate In ammonia at -40℃; Rate constant; electrochemical reaction; | A 34% B 13% C 14% |
With 4,4'-bipyridine; potassium tert-butylate In ammonia at -40℃; electrolysis; | A 34% B 13% C 14% |
4-cyanobenzenethiol
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water | 30% |
methanol
4-fluorobenzonitrile
A
methyl 4-mercaptobenzoate
B
4-cyanobenzenethiol
C
bis(4-cyanophenyl)sulfide
Conditions | Yield |
---|---|
With potassium sulfide; sulfuric acid; zinc Yield given. Multistep reaction; | A n/a B 5% C 9.5% |
4-cyanobenzenethiol
Conditions | Yield |
---|---|
With buffer (pH=11) at 20℃; | |
With buffer (pH=11) at 20℃; Rate constant; |
4-cyanobenzenethiol
Conditions | Yield |
---|---|
Stage #1: trifluoro-acetic acid 4-cyano-phenylsulfanylmethyl ester With ethanol; triethylamine Stage #2: With ammonium chloride |
4-methanesulfinylbenzonitrile
4-cyanobenzenethiol
Conditions | Yield |
---|---|
Stage #1: 4-methanesulfinylbenzonitrile With trifluoroacetic anhydride for 0.5h; Heating; Stage #2: With triethylamine In methanol | 219 mg |
Multi-step reaction with 2 steps 1.1: Heating 2.1: Et3N; EtOH 2.2: NH4Cl View Scheme |
p-cyanophenyl methyl sulfide
4-cyanobenzenethiol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: mCPBA / 0 °C 2.1: Heating 3.1: Et3N; EtOH 3.2: NH4Cl View Scheme | |
Multi-step reaction with 2 steps 1.1: meta-chloroperoxybenzoic acid / CHCl3 / 2 h / 0 °C 2.1: trifluoroacetic anhydride / 0.5 h / Heating 2.2: 219 mg / triethylamine / methanol View Scheme |
5-p-(p-bromophenylsulphonyl)phenyl-3-mercapto-1,2,4-triazole
A
4-((4-bromophenyl)thio)benzonitrile
B
4-((4-bromophenyl)sulfonyl)benzonitrile
C
diphenyl sulfide
D
1-bromo-4-(phenylsulphonyl)benzene
E
4,4'-dibromodiphenyl sulfide
F
4-cyanobenzenethiol
G
para-bromobenzenethiol
Conditions | Yield |
---|---|
at 475℃; under 2 Torr; Pyrolysis; Inert atmosphere; | A 3.6 %Chromat. B 50 %Chromat. C 1.3 %Chromat. D 11.3 %Chromat. E 15.6 %Chromat. F 2.2 %Chromat. G 5.9 %Chromat. |
(phenylsulphonyl)phenyl-3-mercapto-1,2,4-triazole
A
diphenyl sulfide
B
diphenyl sulphone
C
4-(phenylsulfonyl)benzonitrile
D
4-benzenesulfonyl-benzoic acid amide
E
4-cyanobenzenethiol
F
thiophenol
Conditions | Yield |
---|---|
at 475℃; under 2 Torr; Pyrolysis; Inert atmosphere; | A 0.4 %Chromat. B 6.4 %Chromat. C 67.1 %Chromat. D 5.7 %Chromat. E 0.6 %Chromat. F 5.9 %Chromat. |
4-cyanophenyl-O,N,N-dimethyl thiocarbamate
4-cyanobenzenethiol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 200 °C / Inert atmosphere 2: potassium hydroxide / methanol; tetrahydrofuran / 3 h / 20 °C View Scheme |
4-cyanophenol
4-cyanobenzenethiol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1,4-diaza-bicyclo[2.2.2]octane / N,N-dimethyl-formamide / 65 °C 2: 200 °C / Inert atmosphere 3: potassium hydroxide / methanol; tetrahydrofuran / 3 h / 20 °C View Scheme |
4-cyanobenzenethiol
Conditions | Yield |
---|---|
With sodium methylate In methanol; mineral oil at 0 - 20℃; for 14h; | 1.79 g |
4-Cyanochlorobenzene
4-cyanobenzenethiol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 10 °C / Inert atmosphere 1.2: 14 h / 20 °C / Inert atmosphere 2.1: aluminum (III) chloride / benzene / 144 h / 20 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Stage #1: 4-Aminobenzonitrile With hydrogenchloride In water at 0℃; for 0.166667h; Stage #2: With sodium nitrite In water at 0℃; for 1h; Stage #3: potassium ethyl xanthogenate Further stages; |
4-cyanobenzenethiol
p-Methoxybenzyl bromide
4-[(4-methoxybenzyl)thio]benzonitrile
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 18h; | 100% |
4-cyanobenzenethiol
p-cyanobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With N-chloro-succinimide; isopropyl alcohol In dichloromethane at 0 - 20℃; for 1h; | 99% |
4-cyanobenzenethiol
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 0℃; for 0.5h; | 97% |
4-cyanobenzenethiol
1,3-di-O-acetyl-2,5-anhydro-4-deoxy-6-thio-α-D-xylo-hexoseptanose
4-cyanophenyl 3-O-acetyl-2,5-anhydro-4-deoxy-1,6-dithio-α-D-xylo-hexoseptanoside
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 1h; | 97% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 16h; | 96.85% |
4-cyanobenzenethiol
bis(4-cyanophenyl)disulfane
Conditions | Yield |
---|---|
With TiO2/MoS2 (10:1 molar ratio of Ti to Mo) nanocomposite; air In ethanol at 20℃; Irradiation; Green chemistry; | 95% |
With hydrogen bromide; dimethyl sulfoxide In chloroform at 20℃; for 8h; Inert atmosphere; Schlenk technique; | 91% |
With dimethyl sulfoxide at 65℃; | 78% |
With iodine; potassium iodide | |
With iodine |
4-cyanobenzenethiol
methyl 1,3,4,5-tetra-O-acetyl-2,6-anhydro-D-mannose hemiacetal
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at -10℃; for 0.5h; | 95% |
Conditions | Yield |
---|---|
Stage #1: 4-cyanobenzenethiol With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.333333h; Williamson ether synthesis; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 130 - 140℃; Williamson ether synthesis; | 94% |
4-cyanobenzenethiol
4-chlorobenzonitrile
4-cyanophenyl 4′-nitrophenyl sulfide
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere; | 93% |
4-cyanobenzenethiol
1,5-anhydro-3,4-di-O-benzoyl-5-thio-D-threo-pent-1-enitol
4-cyanophenyl 3,4-di-O-benzoyl-2-deoxy-1,5-dithio-D-threo-pentopyranoside
Conditions | Yield |
---|---|
Stage #1: 1,5-anhydro-3,4-di-O-benzoyl-5-thio-D-threo-pent-1-enitol With hydrogen bromide In toluene at 10℃; for 0.333333h; Addition; Stage #2: With silver(I) acetate In toluene; acetonitrile at 20℃; for 2h; Substitution; Stage #3: 4-cyanobenzenethiol With trimethylsilyl trifluoromethanesulfonate In dichloromethane; toluene; acetonitrile at -10 - 20℃; for 1h; Condensation; | 91% |
S,S-diphenylsulphoximine
4-cyanobenzenethiol
Conditions | Yield |
---|---|
With Cu(4-N,N-dimethylaminopyridine)4I; oxygen In dichloromethane at 20℃; | 91% |
4-cyanobenzenethiol
4-((difluoromethyl)thio)benzonitrile
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; tris[2-phenylpyridinato-C2,N]iridium(III) In acetonitrile at 20℃; for 48h; Schlenk technique; Sealed tube; Inert atmosphere; Irradiation; | 90% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile | 90% |
Conditions | Yield |
---|---|
With nanolayered cobalt-molybdenum sulphide with Co/(Mo+Co) mole ratio 0.83 In Hexadecane; toluene at 180℃; under 2625.26 Torr; for 18h; Inert atmosphere; Autoclave; chemoselective reaction; | 90% |
4-cyanobenzenethiol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Inert atmosphere; Reflux; | 89% |
With hydrogenchloride; oxalic acid In water at 20℃; for 0.75h; Kinetics; UV-irradiation; chemoselective reaction; | 93 %Chromat. |
4-cyanobenzenethiol
1,3-chlorobromopropane
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; | 89% |
4-cyanobenzenethiol
1,4-di-O-acetyl-2,5-anhydro-3-O-methyl-6-thio-α-L-guloseptanose
4-cyanophenyl 4-O-acetyl-2,5-anhydro-3-O-methyl-1,6-dithio-α-L-guloseptanoside
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 1h; | 88% |
4-cyanobenzenethiol
1-O-acetyl-2,5-anhydro-3,4-di-O-methanesulfonyl-6-thio-α-D-glucoseptanose
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 1h; | 88% |
Conditions | Yield |
---|---|
In tetrahydrofuran AgOAc and PPh3 dissolved in THF; HSC6H4CN added; soln. stirred for 2 h; layered with hexane for 3 d; elem. anal.; | 88% |
4-cyanobenzenethiol
4-(quinolin-3-ylsulfanyl)benzonitrile
Conditions | Yield |
---|---|
With copper(l) iodide; potassium carbonate; ethylene glycol In N,N-dimethyl acetamide at 110℃; for 48h; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
With palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 16h; Sealed tube; Green chemistry; | 86% |
With dichloro bis(acetonitrile) palladium(II) In water at 120℃; for 16h; Sealed tube; | 69% |
With sulfuric acid In acetic acid |
4-cyanobenzenethiol
Conditions | Yield |
---|---|
With copper(I) thiophene-2-carboxylate; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 19h; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With sodium hydroxide | 85% |
4-cyanobenzenethiol
1,5-di-O-acetyl-2,6-anhydro-3-O-(4-nitrobenzoyl)-2-thio-α-D-altrofuranose
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 20℃; for 1h; | 85% |
4-cyanobenzenethiol
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 24h; | 85% |
The Benzonitrile,4-mercapto-, with the CAS registry number 36801-01-1, has the systematic name of 4-sulfanylbenzonitrile. It belongs to the product categories of Thiol and Aromatic Nitriles. And the molecular formula of the chemical is C7H5NS.
The characteristics of Benzonitrile,4-mercapto- are as followings: (1)ACD/LogP: 2.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.74; (4)ACD/LogD (pH 7.4): 0.03; (5)ACD/BCF (pH 5.5): 8.89; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 113.68; (8)ACD/KOC (pH 7.4): 2.23; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 49.09 Å2; (13)Index of Refraction: 1.602; (14)Molar Refractivity: 39.16 cm3; (15)Molar Volume: 114 cm3; (16)Polarizability: 15.52×10-24cm3; (17)Surface Tension: 50.6 dyne/cm; (18)Density: 1.18 g/cm3; (19)Flash Point: 113.7 °C; (20)Enthalpy of Vaporization: 50.23 kJ/mol; (21)Boiling Point: 264.4 °C at 760 mmHg; (22)Vapour Pressure: 0.00972 mmHg at 25°C.
Uses of Benzonitrile,4-mercapto-: It can react with thiocarbonyl dichloride to produce (p-Cyanphenyl)chlordithioformiat. This reaction will need reagent NaOH, and the yield is about 85%.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: N#Cc1ccc(S)cc1
(2)InChI: InChI=1/C7H5NS/c8-5-6-1-3-7(9)4-2-6/h1-4,9H
(3)InChIKey: MVPUXVBBHWUOFS-UHFFFAOYAD
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