Benzonitrile,4-mercapto- supplier

Name
4-CYANOTHIOPHENOL
EINECS
CAS No. 36801-01-1
Article Data16
CAS DataBase
Density 1.18 g/cm³
Solubility
Melting Point 51-52℃
Formula C₇H₅NS
Boiling Point 264.4 °C at 760 mmHg
Molecular Weight 135.189
Flash Point 113.7 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4-Cyanobenzenethiol;4-Cyanothiophenol;4-Mercaptobenzonitrile;p-Cyanobenzenethiol;p-Cyanothiophenol;4-sulfanylbenzonitrile;
PSA 62.59000
LogP 1.84698

Synthetic route

: 623-00-7
4-bromobenzenecarbonitrile

: 36801-01-1
4-cyanobenzenethiol

Conditions

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;

: 3058-39-7
4-iodobenzonitrile

: 36801-01-1
4-cyanobenzenethiol

Conditions

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%

: 59177-46-7
4-mercaptobenzamide

: 36801-01-1
4-cyanobenzenethiol

Conditions

Conditions	Yield
With trichlorophosphate In N,N-dimethyl-formamide at 0℃; for 2h;	93%

: triphenylmethyl p-cyanophenylsulfide

A: 519-73-3
triphenylmethane

B: 36801-01-1
4-cyanobenzenethiol

C: 4-tritylmercaptobenzamide

Conditions

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%

...Expand

: 19290-43-8
4-cyanophenyl-S,N,N-dimethyl thiocarbamate

: 36801-01-1
4-cyanobenzenethiol

Conditions

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

: 150993-53-6
4-(benzylsulfanyl)benzonitrile

: 36801-01-1
4-cyanobenzenethiol

Conditions

Conditions	Yield
With aluminum (III) chloride In benzene at 20℃; for 144h; Inert atmosphere;	76%

: 1194-02-1
4-fluorobenzonitrile

A: 36801-01-1
4-cyanobenzenethiol

B: 6339-51-1
bis(4-cyanophenyl)disulfane

C: 46836-99-1
bis(4-cyanophenyl)sulfide

Conditions

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%

...Expand

: 1194-02-1
4-fluorobenzonitrile

: 36801-01-1
4-cyanobenzenethiol

Conditions

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%

: 623-03-0
4-Cyanochlorobenzene

: 17356-08-0
thiourea

A: 36801-01-1
4-cyanobenzenethiol

B: 6339-51-1
bis(4-cyanophenyl)disulfane

C: 46836-99-1
bis(4-cyanophenyl)sulfide

Conditions

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%

...Expand

: ethyl 4-cyanophenyl xanthate

: 36801-01-1
4-cyanobenzenethiol

Conditions

Conditions	Yield
With potassium hydroxide In ethanol; water	30%

: 67-56-1
methanol

: 1194-02-1
4-fluorobenzonitrile

A: 6302-65-4
methyl 4-mercaptobenzoate

B: 36801-01-1
4-cyanobenzenethiol

C: 46836-99-1
bis(4-cyanophenyl)sulfide

Conditions

Conditions	Yield
With potassium sulfide; sulfuric acid; zinc Yield given. Multistep reaction;	A n/a B 5% C 9.5%

...Expand

: C12H16N3S(1+)*I(1-)

: 36801-01-1
4-cyanobenzenethiol

Conditions

Conditions	Yield
With buffer (pH=11) at 20℃;
With buffer (pH=11) at 20℃; Rate constant;

: trifluoro-acetic acid 4-cyano-phenylsulfanylmethyl ester

: 36801-01-1
4-cyanobenzenethiol

Conditions

Conditions	Yield
Stage #1: trifluoro-acetic acid 4-cyano-phenylsulfanylmethyl ester With ethanol; triethylamine Stage #2: With ammonium chloride

: 60958-04-5, 121405-10-5, 97474-48-1
4-methanesulfinylbenzonitrile

: 36801-01-1
4-cyanobenzenethiol

Conditions

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

: 21382-98-9
p-cyanophenyl methyl sulfide

: 36801-01-1
4-cyanobenzenethiol

Conditions

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

: 141212-58-0
5-p-(p-bromophenylsulphonyl)phenyl-3-mercapto-1,2,4-triazole

A: 79995-40-7
4-((4-bromophenyl)thio)benzonitrile

B: 80988-12-1
4-((4-bromophenyl)sulfonyl)benzonitrile

C: 139-66-2
diphenyl sulfide

D: 23038-36-0
1-bromo-4-(phenylsulphonyl)benzene

E: 3393-78-0
4,4'-dibromodiphenyl sulfide

F: 36801-01-1
4-cyanobenzenethiol

G: 106-53-6
para-bromobenzenethiol

Conditions

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.

...Expand

: 141212-52-4
(phenylsulphonyl)phenyl-3-mercapto-1,2,4-triazole

A: 139-66-2
diphenyl sulfide

B: 127-63-9
diphenyl sulphone

C: 28525-13-5
4-(phenylsulfonyl)benzonitrile

D: 55204-60-9
4-benzenesulfonyl-benzoic acid amide

E: 36801-01-1
4-cyanobenzenethiol

F: 108-98-5
thiophenol

Conditions

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.

...Expand

: 20994-09-6
4-cyanophenyl-O,N,N-dimethyl thiocarbamate

: 36801-01-1
4-cyanobenzenethiol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 200 °C / Inert atmosphere 2: potassium hydroxide / methanol; tetrahydrofuran / 3 h / 20 °C View Scheme

: 767-00-0
4-cyanophenol

: 36801-01-1
4-cyanobenzenethiol

Conditions

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

: methyl 3-((4-cyanophenyl)thio)propanoate

: 36801-01-1
4-cyanobenzenethiol

Conditions

Conditions	Yield
With sodium methylate In methanol; mineral oil at 0 - 20℃; for 14h;	1.79 g

: 623-03-0
4-Cyanochlorobenzene

: 36801-01-1
4-cyanobenzenethiol

Conditions

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

: 140-89-6
potassium ethyl xanthogenate

: 873-74-5
4-Aminobenzonitrile

: 36801-01-1
4-cyanobenzenethiol

Conditions

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;

: 36801-01-1
4-cyanobenzenethiol

: 2746-25-0
p-Methoxybenzyl bromide

: 1257086-86-4
4-[(4-methoxybenzyl)thio]benzonitrile

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 18h;	100%

: 36801-01-1
4-cyanobenzenethiol

: 49584-26-1
p-cyanobenzenesulfonyl chloride

Conditions

Conditions	Yield
With N-chloro-succinimide; isopropyl alcohol In dichloromethane at 0 - 20℃; for 1h;	99%

: 36801-01-1
4-cyanobenzenethiol

: 1-O-acetyl-2,6-anhydro-4-deoxy-3-O-methyl-6-thio-D-lyxo-hexospyranose

: 40cyanophenyl 3-S-(4-cyanophenyl)-2,6-thioanhydro-4-deoxy-2,3-dithio-β-D-arabino-hexopyranoside

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 0℃; for 0.5h;	97%

: 36801-01-1
4-cyanobenzenethiol

: 316376-13-3
1,3-di-O-acetyl-2,5-anhydro-4-deoxy-6-thio-α-D-xylo-hexoseptanose

: 316376-15-5
4-cyanophenyl 3-O-acetyl-2,5-anhydro-4-deoxy-1,6-dithio-α-D-xylo-hexoseptanoside

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 1h;	97%

: 36801-01-1
4-cyanobenzenethiol

: 75-26-3
isopropyl bromide

: 4-(isopropylsulfanyl)benzonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 16h;	96.85%

: 36801-01-1
4-cyanobenzenethiol

: 6339-51-1
bis(4-cyanophenyl)disulfane

Conditions

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

: 36801-01-1
4-cyanobenzenethiol

: 354150-48-4
methyl 1,3,4,5-tetra-O-acetyl-2,6-anhydro-D-mannose hemiacetal

: 3,4,5-tri-O-acetyl-2,6-anhydro-D-mannose S-4-cyanophenyl O-methyl monothiohemiacetal

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at -10℃; for 0.5h;	95%

: 111-24-0
1,5-dibromo-pentane

: 36801-01-1
4-cyanobenzenethiol

: 1,5-bis[(4-cyanophenyl)thio]pentane

Conditions

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%

: 36801-01-1
4-cyanobenzenethiol

: 100-00-5
4-chlorobenzonitrile

: 21969-10-8
4-cyanophenyl 4′-nitrophenyl sulfide

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	93%

: 36801-01-1
4-cyanobenzenethiol

: 189382-65-8
1,5-anhydro-3,4-di-O-benzoyl-5-thio-D-threo-pent-1-enitol

: 189382-68-1
4-cyanophenyl 3,4-di-O-benzoyl-2-deoxy-1,5-dithio-D-threo-pentopyranoside

Conditions

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%

: 22731-83-5
S,S-diphenylsulphoximine

: 36801-01-1
4-cyanobenzenethiol

: S,S-diphenyl-N-(4-cyanphenylthio)sulfoximine

Conditions

Conditions	Yield
With Cu(4-N,N-dimethylaminopyridine)4I; oxygen In dichloromethane at 20℃;	91%

: 36801-01-1
4-cyanobenzenethiol

: (difluoromethyl)triphenylphosphonium trifluoromethanesulfonate

: 4837-25-6
4-((difluoromethyl)thio)benzonitrile

Conditions

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%

: 36801-01-1
4-cyanobenzenethiol

: C15H6BBr5F2N2O

: C29H14BBr3F2N4OS2

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile	90%

: 36801-01-1
4-cyanobenzenethiol

: 100-51-6
benzyl alcohol

: 150993-53-6
4-(benzylsulfanyl)benzonitrile

Conditions

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%

: 36801-01-1
4-cyanobenzenethiol

: 4-(aminomethyl)benzenethiol

Conditions

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.

: 36801-01-1
4-cyanobenzenethiol

: 109-70-6
1,3-chlorobromopropane

: 4-[(3-chloropropyl)sulfanyl]benzonitrile

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;	89%

: 36801-01-1
4-cyanobenzenethiol

: 316376-25-7
1,4-di-O-acetyl-2,5-anhydro-3-O-methyl-6-thio-α-L-guloseptanose

: 316376-27-9
4-cyanophenyl 4-O-acetyl-2,5-anhydro-3-O-methyl-1,6-dithio-α-L-guloseptanoside

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 1h;	88%

: 36801-01-1
4-cyanobenzenethiol

: 59647-83-5
1-O-acetyl-2,5-anhydro-3,4-di-O-methanesulfonyl-6-thio-α-D-glucoseptanose

: 4-cyanophenyl 2,5-anhydro-3,4-di-O-methanesulfonyl-1,6-dithio-α-D-glucoseptanoside

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 1h;	88%

: 36801-01-1
4-cyanobenzenethiol

: 563-63-3
silver(I) acetate

: 603-35-0
triphenylphosphine

: Ag6(SC6H4CN)6(P(C6H5)3)6

Conditions

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%

...Expand

: S-quinolin-3-ylbenzothioate

: 36801-01-1
4-cyanobenzenethiol

: 1299398-65-4
4-(quinolin-3-ylsulfanyl)benzonitrile

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate; ethylene glycol In N,N-dimethyl acetamide at 110℃; for 48h; Inert atmosphere;	87%

: 91-01-0
1,1-Diphenylmethanol

: 36801-01-1
4-cyanobenzenethiol

: 4-(benzhydrylthio)benzonitrile

Conditions

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

: 36801-01-1
4-cyanobenzenethiol

: 5-iodo-6-(trifluoromethyl)pyrimidine-2,4-diol

: 4-((2,4-dihydroxy-6-(trifluoromethyl)pyrimidin-5-yl)thio)benzonitrile

Conditions

Conditions	Yield
With copper(I) thiophene-2-carboxylate; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 19h; Inert atmosphere;	86%

: 463-71-8
thiophosgene

: 36801-01-1
4-cyanobenzenethiol

: (p-Cyanphenyl)chlordithioformiat

Conditions

Conditions	Yield
With sodium hydroxide	85%

: 36801-01-1
4-cyanobenzenethiol

: 321157-02-2
1,5-di-O-acetyl-2,6-anhydro-3-O-(4-nitrobenzoyl)-2-thio-α-D-altrofuranose

: 4-cyanophenyl 5-O-acetyl-2,6-anhydro-3-O-(4-nitrobenzoyl)-2-thio-α-D-altrofuranoside

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 20℃; for 1h;	85%

: 36801-01-1
4-cyanobenzenethiol

: Acetic acid (2S,3R,4R,5R)-4,5-diacetoxy-2-diacetoxymethyl-tetrahydro-pyran-3-yl ester

: 3,4,5-tri-O-acetyl-2,6-anhydro-D-altrose bis(4-cyanophenyl) dithioacetal

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 24h;	85%

Benzonitrile,4-mercapto- Specification

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

Product Name

4-CYANOTHIOPHENOL

Synthetic route

Benzonitrile,4-mercapto- Specification

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