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36801-01-1

Basic Information
CAS No.: 36801-01-1
Name: 4-CYANOTHIOPHENOL
Article Data: 16
Molecular Structure:
Molecular Structure of 36801-01-1 (4-CYANOTHIOPHENOL)
Formula: C7H5NS
Molecular Weight: 135.189
Synonyms: 4-Cyanobenzenethiol;4-Cyanothiophenol;4-Mercaptobenzonitrile;p-Cyanobenzenethiol;p-Cyanothiophenol;4-sulfanylbenzonitrile;
Density: 1.18 g/cm3
Melting Point: 51-52℃
Boiling Point: 264.4 °C at 760 mmHg
Flash Point: 113.7 °C
PSA: 62.59000
LogP: 1.84698
Synthetic route
623-00-7

4-bromobenzenecarbonitrile

36801-01-1

4-cyanobenzenethiol

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
19290-43-8

4-cyanophenyl-S,N,N-dimethyl thiocarbamate

36801-01-1

4-cyanobenzenethiol

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
1194-02-1

4-fluorobenzonitrile

36801-01-1

4-cyanobenzenethiol

Conditions
ConditionsYield
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
ConditionsYield
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%

ethyl 4-cyanophenyl xanthate

36801-01-1

4-cyanobenzenethiol

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water30%
Downstream Products
19290-43-8
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  • 4-sulfanylbenzonitrile

  • Casno:

    36801-01-1

    4-sulfanylbenzonitrile

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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