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106-45-6 Usage

Chemical Properties

White or colorless solid melt

Uses

p-Thiocresol is used as a pharmaceutical intermediate.

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 1235, 1980 DOI: 10.1016/S0040-4039(00)71380-3

Safety Profile

Poison by intraperitoneal route. A flammable liquid. When heated to decomposition it emits toxic fumes of SOx. See also a- TOLUENETHIOL and MERCAPTANS.

Purification Methods

Crystallise the thiol from pet ether (b 40-70o). The 2,4-dinitrophenyl thioether has m 103o (from EtOH), and the 2,4-dinitrophenyl sulfone has m 190o (from EtOH). [Beilstein 6 IV 2153.]

Check Digit Verification of cas no

The CAS Registry Mumber 106-45-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 106-45:
(5*1)+(4*0)+(3*6)+(2*4)+(1*5)=36
36 % 10 = 6
So 106-45-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H8S/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3/p-1

106-45-6 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (B24970)  p-Thiocresol, 98%   

  • 106-45-6

  • 25g

  • 362.0CNY

  • Detail
  • Alfa Aesar

  • (B24970)  p-Thiocresol, 98%   

  • 106-45-6

  • 100g

  • 690.0CNY

  • Detail
  • Alfa Aesar

  • (B24970)  p-Thiocresol, 98%   

  • 106-45-6

  • 500g

  • 2431.0CNY

  • Detail
  • Aldrich

  • (T28525)  4-Methylbenzenethiol  98%

  • 106-45-6

  • T28525-5G

  • 318.24CNY

  • Detail
  • Aldrich

  • (T28525)  4-Methylbenzenethiol  98%

  • 106-45-6

  • T28525-100G

  • 1,095.12CNY

  • Detail
  • Aldrich

  • (T28525)  4-Methylbenzenethiol  98%

  • 106-45-6

  • T28525-500G

  • 3,106.35CNY

  • Detail

106-45-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name p-Toluenethiol

1.2 Other means of identification

Product number -
Other names p-Tolyl Mercaptan

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:106-45-6 SDS

106-45-6Synthetic route

4-tolyl iodide
624-31-7

4-tolyl iodide

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 90℃; for 20h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;99%
With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 90℃; for 20h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;97%
With sodiumsulfide nonahydrate; copper; ethane-1,2-dithiol In dimethyl sulfoxide at 100℃; for 20h; Inert atmosphere; Sealed tube;97%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With potassium sulfide; acetic acid; triphenylphosphine; zinc In chloroform; water at 60℃; for 0.5h; Solvent; Reagent/catalyst;97.5%
With ISOPROPYLAMIDE; dimethylsilicon dichloride; zinc In 1,2-dichloro-ethane at 75℃; for 1.5h;96%
With formic acid; 6% Pd/C; triphenylphosphine at 60℃; for 8h;92%
di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With indium; ammonium chloride In ethanol for 1h; Reduction; Heating;96%
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 35℃; for 0.25h; Reduction;95%
With ammonia; aluminium; sodium chloride at 25℃; for 1h;94%
1-pentyl tosylate
4450-76-4

1-pentyl tosylate

A

amyl iodide
628-17-1

amyl iodide

B

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With iodine; triphenylphosphine In benzene for 0.166667h; Heating;A 90%
B 95%
(4-methylpyridyl)(4-methylphenyl)sulfide
128916-30-3

(4-methylpyridyl)(4-methylphenyl)sulfide

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With magnesium In methanol at 20℃; for 4h;92%
4-methylphenyl methylsulfide
623-13-2

4-methylphenyl methylsulfide

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; diethylamine In xylene for 6h; Heating;90%
With sodium methylselenide In N,N-dimethyl-formamide for 8h; Heating;55%
di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

triphenylphosphine
603-35-0

triphenylphosphine

A

para-thiocresol
106-45-6

para-thiocresol

B

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

Conditions
ConditionsYield
In benzene for 23.5h; Product distribution; Mechanism; Heating; further reaction partners - various diaryl disulfides, diphenyl diselenide, tetrabutylammonium iodide, tributylphosphine;A 90%
B 90%
sodium 4-methylbenzenesulfinate
824-79-3

sodium 4-methylbenzenesulfinate

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With iodine; triphenylphosphine In 1,4-dioxane; benzene for 2h; Heating;88%
With hydrogenchloride; tin In water for 24h; Heating;81%
Multi-step reaction with 2 steps
1: iodine; triphenylphosphine / ethanol / 2 h / Reflux; Green chemistry
2: indole; iodine; triphenylphosphine / ethanol / 2 h / Reflux; Green chemistry
View Scheme
Multi-step reaction with 2 steps
1: sulfur dioxide / water / 9.5 h / 110 °C / Inert atmosphere
2: sodium tetrahydroborate; sodium hydroxide / water; tetrahydrofuran / 3 h / 65 - 67 °C / Inert atmosphere
View Scheme
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With 6% Pd/C; iodine; triphenylphosphine; isopropyl alcohol for 6h; Reflux;88%
With triphenylphosphine; iodine In benzene for 2.5h; Heating;89 % Chromat.
With diphosphorus pentasulfide; lithium aluminium tetrahydride 1.) sulfolane, 90 deg C for 24 h 2.) ether, room temperature for 30 min; Yield given. Multistep reaction;
3,5-diphenyl-5-(p-tolylthio)oxazolidine-2,4-dione

3,5-diphenyl-5-(p-tolylthio)oxazolidine-2,4-dione

A

2-oxo-N,2-diphenylacetamide
4732-66-5

2-oxo-N,2-diphenylacetamide

B

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With potassium hydroxide In 1,4-dioxane Schlenk technique; Inert atmosphere;A 83%
B 75%
para-chlorotoluene
106-43-4

para-chlorotoluene

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
Stage #1: para-chlorotoluene With water; palladium diacetate; caesium carbonate; sodium thiosulfate; XPhos In toluene; tert-butyl alcohol at 80℃; for 24h; Inert atmosphere;
Stage #2: With hydrogenchloride; zinc In water for 1h; Cooling with ice;
82%
With sodium hydroxide; 1-thiopropane 1) N-methyl-2-pyrrolidone, removal of water by toluene reflux, 2) reflux (ca. 186 deg C), 20 h; other reagent: n-butyl mercaptan; Yield given. Multistep reaction;
With pumice stone; hydrogen sulfide; thorium dioxide at 700℃;
With hydrogen sulfide at 700℃;
para-bromotoluene
106-38-7

para-bromotoluene

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
Stage #1: para-bromotoluene With water; caesium carbonate; sodium thiosulfate; bis(dibenzylideneacetone)-palladium(0); XPhos In toluene; tert-butyl alcohol at 80℃; for 24h; Inert atmosphere;
Stage #2: With hydrogenchloride; zinc In water for 1h; Cooling with ice;
81%
With sodium thiomethoxide In N,N-dimethyl acetamide at 150℃;
With sodiumsulfide nonahydrate; copper; ethane-1,2-dithiol In dimethyl sulfoxide at 100℃; for 20h; Inert atmosphere; Green chemistry;14 %Chromat.
4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
Stage #1: 4-methylphenylboronic acid With copper (II)-fluoride; sulfur In dimethyl sulfoxide at 100℃; for 12h; Chan-Lam Coupling; Inert atmosphere;
Stage #2: With sodium tetrahydroborate In dimethyl sulfoxide at 40℃; for 5h; Inert atmosphere;
79%
p-toluenesulfonic acid monohydrate
6192-52-5

p-toluenesulfonic acid monohydrate

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

A

S-(trifluoroacetyl)-p-methylthiophenol
75072-07-0

S-(trifluoroacetyl)-p-methylthiophenol

B

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide In dichloromethane for 20h; Product distribution; Ambient temperature;A 78%
B 11%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide 1.) CH2Cl2, 20h, room temp.; 2.) MeOH, 30 min, room temp.; Yield given. Multistep reaction. Further byproducts given;
With sodium hydroxide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; tetra-(n-butyl)ammonium iodide 1.) CH2Cl2, 20h, room temp.; 2.) 0 deg C; Yield given. Multistep reaction. Further byproducts given;
1-<α-(p-tolylsulfonyl)ethyl>-4-methoxybenzene
122948-71-4

1-<α-(p-tolylsulfonyl)ethyl>-4-methoxybenzene

methylmagnesium bromide
75-16-1

methylmagnesium bromide

A

(4,4'-dimethyl-1,1'-biphenyl)
613-33-2

(4,4'-dimethyl-1,1'-biphenyl)

B

4-Methylbiphenyl
644-08-6

4-Methylbiphenyl

C

4-methylphenyl methylsulfide
623-13-2

4-methylphenyl methylsulfide

D

1-isopropenyl-4-methoxybenzene
1712-69-2

1-isopropenyl-4-methoxybenzene

E

1-methoxy-4-(1-methylethyl)benzene
4132-48-3

1-methoxy-4-(1-methylethyl)benzene

F

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) diiodide; tricyclohexylphosphine; phenylboronic acid In tetrahydrofuran at 70℃; Kumada Cross-Coupling; Inert atmosphere;A 11%
B 31%
C 12%
D 78%
E 10%
F 7%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With ammonium formate at 100 - 200℃; for 7h; neat (no solvent);77%
With phosphorus; phosphoric acid; potassium iodide
With phosphonium iodide; hydrogen iodide at 75 - 100℃;
With diphosphorus pentasulfide; lithium aluminium tetrahydride 1.) sulfolane, 90 deg C for 60 h 2.) ether, room temperature for 30 min; Yield given. Multistep reaction;
1-phenyl-2-(p-tolylthio)ethanone
33046-45-6

1-phenyl-2-(p-tolylthio)ethanone

A

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

B

para-thiocresol
106-45-6

para-thiocresol

C

acetophenone
98-86-2

acetophenone

Conditions
ConditionsYield
With electrolysis on Pt electrode In acetonitrile Product distribution; other electrode (Hg), other solvent (aq. ethanol), influence of phenol;A n/a
B n/a
C 72%
3-[(4-methylphenyl)sulfanyl]-1-propanol
3147-28-2

3-[(4-methylphenyl)sulfanyl]-1-propanol

A

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

B

4-methylphenyl propyl sulfide
24599-52-8

4-methylphenyl propyl sulfide

C

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
PPA In carbon disulfide for 40h; Ambient temperature;A 72%
B 21%
C 4%
sodium tosylate
657-84-1

sodium tosylate

A

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

B

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With sulfuric acid; triphenylphosphine In water at 20℃; for 10h;A 30%
B 68%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

A

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

B

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran for 4h; Heating;A 60.2%
B 27%
With sodium tetrahydroborate In tetrahydrofuran for 2h; Heating;A 30.9%
B 27%
With sodium tetrahydroborate In tetrahydrofuran Product distribution; Heating; effect of reaction time;
With water; triphenylphosphine In tetrahydrofuran at 20℃;
γ-chloropropyl 4-methylphenyl sulphide
3147-30-6

γ-chloropropyl 4-methylphenyl sulphide

A

6-Methyl-3,4-dihydro-2H-1-benzothiopyran
71153-74-7

6-Methyl-3,4-dihydro-2H-1-benzothiopyran

B

4-methylphenyl propyl sulfide
24599-52-8

4-methylphenyl propyl sulfide

C

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
aluminium trichloride In carbon disulfide for 3h; Heating;A 60%
B 15%
C 9%
p-Tolyl-thionitrit
64732-71-4

p-Tolyl-thionitrit

methyllithium
917-54-4

methyllithium

A

4-methylphenyl methylsulfide
623-13-2

4-methylphenyl methylsulfide

B

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

C

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
In diethyl ether at -70℃; for 0.05h;A 57%
B n/a
C n/a
p-Tolyl-thionitrit
64732-71-4

p-Tolyl-thionitrit

phenylmagnesium bromide

phenylmagnesium bromide

A

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

B

4-tolyl phenyl sulfide
3699-01-2

4-tolyl phenyl sulfide

C

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
In diethyl ether at -70℃; for 0.05h;A n/a
B 57%
C n/a
2-(p-tolylthio)-ethanol
13290-16-9

2-(p-tolylthio)-ethanol

A

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

B

p-methyl-2-phenylethyl chloride
32327-68-7

p-methyl-2-phenylethyl chloride

C

1,2-bis(p-tolylthio)ethane
3238-95-7

1,2-bis(p-tolylthio)ethane

D

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
aluminium trichloride; nitromethane In carbon disulfide for 40h; Ambient temperature;A 2.1%
B 54%
C 43%
D 0.3%
4-(phenyldisulfanyl)toluene
29627-34-7

4-(phenyldisulfanyl)toluene

diphenyldisulfane
882-33-7

diphenyldisulfane

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With triphenylphosphine In 1,4-dioxane; water53%
sodium tosylate
657-84-1

sodium tosylate

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With 18-crown-6 ether; iodine; triphenylphosphine In benzene for 5h; Heating;50%
With triphenylphosphine; 18-crown-6 ether; iodine In benzene for 30.5h; Heating;85 % Chromat.
With diphosphorus pentasulfide; lithium aluminium tetrahydride 1.) sulfolane, 90 deg C for 24 h 2.) ether, room temperature for 30 min; Yield given. Multistep reaction;
N-(4-methylphenylthiomethyl)benzamide
103603-53-8

N-(4-methylphenylthiomethyl)benzamide

A

benzonitrile
100-47-0

benzonitrile

B

2-phenyl-6-methyl-4H-1,3-benzothiazine
124778-69-4

2-phenyl-6-methyl-4H-1,3-benzothiazine

C

para-thiocresol
106-45-6

para-thiocresol

D

2,8-dimethyl-6H,12H-dibenzo<1,5>dithiocin

2,8-dimethyl-6H,12H-dibenzo<1,5>dithiocin

Conditions
ConditionsYield
With trichlorophosphate for 1h; Heating;A 49%
B 9.8%
C 16%
D 11%
4-(phenyldisulfanyl)toluene
29627-34-7

4-(phenyldisulfanyl)toluene

diphenyldisulfane
882-33-7

diphenyldisulfane

A

phenyl toluene-4-thiosulfonate
3541-14-8

phenyl toluene-4-thiosulfonate

B

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With PPEA 4%
B 46%
3-[(4-methylphenyl)sulfanyl]-1-propanol
3147-28-2

3-[(4-methylphenyl)sulfanyl]-1-propanol

A

ethyl p-tolyl sulfide
622-63-9

ethyl p-tolyl sulfide

B

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

C

para-thiocresol
106-45-6

para-thiocresol

D

4-Methyl-2-propyl-1-p-tolyldisulfanyl-benzene

4-Methyl-2-propyl-1-p-tolyldisulfanyl-benzene

Conditions
ConditionsYield
sulfuric acid In carbon disulfide for 40h; Ambient temperature;A 4%
B 45%
C 3%
D 42%
sulfuric acid In carbon disulfide for 40h; Product distribution; Ambient temperature; further catalysts;A 4%
B 45%
C 3%
D 42%
sulfuric acid In carbon disulfide for 40h; Ambient temperature;A 4%
B 45%
C 3%
D 42%
sodium tosylate
657-84-1

sodium tosylate

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

A

S-(trifluoroacetyl)-p-methylthiophenol
75072-07-0

S-(trifluoroacetyl)-p-methylthiophenol

B

para-thiocresol
106-45-6

para-thiocresol

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide In dichloromethane for 19h; Product distribution; Ambient temperature;A 44%
B 26%
With sodium hydroxide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; tetra-(n-butyl)ammonium iodide 1.) CH2Cl2, 22h, room temp.; 2.) 0 deg C; Yield given. Multistep reaction. Further byproducts given;
allyl bromide
106-95-6

allyl bromide

para-thiocresol
106-45-6

para-thiocresol

allyl (p-tolyl)sulfide
1516-28-5

allyl (p-tolyl)sulfide

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃;100%
Stage #1: para-thiocresol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h;
Stage #2: allyl bromide In tetrahydrofuran; mineral oil for 0.4h;
95%
With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 4.33333h;95%
para-thiocresol
106-45-6

para-thiocresol

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

Conditions
ConditionsYield
With bis dichromate In dichloromethane at 0 - 5℃; for 1h;100%
With bromine; potassium hydrogencarbonate In dichloromethane100%
With N-phenyltriazolinedione In toluene at 20℃; for 0.166667h;100%
1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

para-thiocresol
106-45-6

para-thiocresol

γ-chloropropyl 4-methylphenyl sulphide
3147-30-6

γ-chloropropyl 4-methylphenyl sulphide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃;100%
With sodium hydroxide In ethanol at 100℃;65%
With potassium hydroxide
methyl vinyl ketone
78-94-4

methyl vinyl ketone

para-thiocresol
106-45-6

para-thiocresol

4-(p-tolylthio)butan-2-one
6110-02-7

4-(p-tolylthio)butan-2-one

Conditions
ConditionsYield
With zirconium In acetonitrile Michael Addition; Electrolysis; diastereoselective reaction;100%
With triethylammonium acetate at 25℃; for 0.0166667h; Thia-Michael reaction; chemoselective reaction;99%
Mg-La mixed oxides In N,N-dimethyl-formamide at 24.85℃; for 0.45h; Michael addition;97%
(methoxycarbonyl)disulfanyl chloride
88766-29-4

(methoxycarbonyl)disulfanyl chloride

para-thiocresol
106-45-6

para-thiocresol

Methoxycarbonyl 4-methylphenyl trisulfane
94839-62-0

Methoxycarbonyl 4-methylphenyl trisulfane

Conditions
ConditionsYield
In dichloromethane at -78℃; for 1h;100%
4-tosylacetonitrile
16192-07-7

4-tosylacetonitrile

para-thiocresol
106-45-6

para-thiocresol

3-p-tolylsulphonyl-2-p-tolylthiopropene
97479-48-6

3-p-tolylsulphonyl-2-p-tolylthiopropene

Conditions
ConditionsYield
With triethylamine In methanol for 1.75h; Ambient temperature;100%
With triethylamine In benzene for 2h; Ambient temperature;65%
With triethylamine In benzene for 18h; Ambient temperature;55%
With triethylamine In benzene
p-toluene(N-phenylsulfonyl)iminosulfinyl chloride
33840-84-5

p-toluene(N-phenylsulfonyl)iminosulfinyl chloride

para-thiocresol
106-45-6

para-thiocresol

A

benzenesulfonamide
98-10-2

benzenesulfonamide

B

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

Conditions
ConditionsYield
In benzene at 20℃; for 2.5h; Mechanism;A 100%
B 95%
2,3-dicyanobenzaldehyde
129221-76-7

2,3-dicyanobenzaldehyde

para-thiocresol
106-45-6

para-thiocresol

3-Oxo-1-p-tolylsulfanyl-2,3-dihydro-1H-isoindole-4-carbonitrile
129221-84-7

3-Oxo-1-p-tolylsulfanyl-2,3-dihydro-1H-isoindole-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In chloroform at 20℃; for 4h;100%
(methoxy)diphenyl-λ6-sulfanenitrile
127022-75-7

(methoxy)diphenyl-λ6-sulfanenitrile

para-thiocresol
106-45-6

para-thiocresol

A

4-methylphenyl methylsulfide
623-13-2

4-methylphenyl methylsulfide

B

S,S-diphenylsulphoximine
22731-83-5

S,S-diphenylsulphoximine

Conditions
ConditionsYield
In benzene at 30℃; for 6h; Rate constant; Product distribution;A 77%
B 100%
In benzene at 30℃; for 6h; Yields of byproduct given;A 77%
B n/a
vinylidene-1,1-diphosphonic acid
34162-79-3

vinylidene-1,1-diphosphonic acid

para-thiocresol
106-45-6

para-thiocresol

(1-Phosphono-2-p-tolylsulfanyl-ethyl)-phosphonic acid
87774-69-4

(1-Phosphono-2-p-tolylsulfanyl-ethyl)-phosphonic acid

Conditions
ConditionsYield
With acetic acid; triethylamine at 110℃; for 15h;100%
p-toluene(N-benzoyl)iminosulfinyl chloride
70925-53-0

p-toluene(N-benzoyl)iminosulfinyl chloride

para-thiocresol
106-45-6

para-thiocresol

A

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

B

benzamidene hydrochloride
15934-46-0

benzamidene hydrochloride

Conditions
ConditionsYield
In benzene at 20℃; for 2.5h; Mechanism;A 90%
B 100%
para-thiocresol
106-45-6

para-thiocresol

4-(4-fluorophenyl)-4-oxo-n-butyl chloride
3874-54-2

4-(4-fluorophenyl)-4-oxo-n-butyl chloride

1-(4-fluorophenyl)-4-(p-tolylthio)butan-1-one
132427-90-8

1-(4-fluorophenyl)-4-(p-tolylthio)butan-1-one

Conditions
ConditionsYield
100%
With triethylamine In tetrahydrofuran for 16h; Ambient temperature;99%
para-thiocresol
106-45-6

para-thiocresol

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

Conditions
ConditionsYield
With dinitrogen tetraoxide In tetrachloromethane; diethyl ether for 2.5h; Ambient temperature;100%
With dihydrogen peroxide; trichlorophosphate In water at 80℃; for 1.16667h; Micellar solution;95%
With HOF* CH3CN In dichloromethane at 0℃;90%
With dihydrogen peroxide; methyltrioxorhenium(VII) In acetonitrile at 20℃;87%
Multi-step reaction with 2 steps
1: pyridine / acetonitrile / Heating
2: hydrogenchloride; water / 40 °C
View Scheme
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

para-thiocresol
106-45-6

para-thiocresol

(3-phenylpropyl)(p-tolyl)sulfane
38644-97-2

(3-phenylpropyl)(p-tolyl)sulfane

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 12h;100%
With potassium hydroxide
With potassium carbonate In acetone at 45℃;
Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃;100%
With trifluorormethanesulfonic acid In dichloromethane at 0℃; for 2.5h; Molecular sieve; Inert atmosphere; stereoselective reaction;88%
With boron trifluoride diethyl etherate In dichloromethane87%
1-iodo-2,4-dimethylbenzene
4214-28-2

1-iodo-2,4-dimethylbenzene

para-thiocresol
106-45-6

para-thiocresol

(2,4‑dimethylphenyl)(4‑methylphenyl) sulfide
16704-46-4

(2,4‑dimethylphenyl)(4‑methylphenyl) sulfide

Conditions
ConditionsYield
With 1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2λ5,4λ5-catenadi(phosphazene); copper(I) bromide In toluene Substitution; Heating;100%
Stage #1: para-thiocresol With potassium hydroxide In methanol at 70℃; for 0.25h; Inert atmosphere; Schlenk technique; Green chemistry;
Stage #2: 1-iodo-2,4-dimethylbenzene With copper(l) iodide In methanol at 110℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;
3,5-dimethylphenyl iodide
22445-41-6

3,5-dimethylphenyl iodide

para-thiocresol
106-45-6

para-thiocresol

(3,5‑dimethylphenyl)(4‑methylphenyl) sulfide

(3,5‑dimethylphenyl)(4‑methylphenyl) sulfide

Conditions
ConditionsYield
Stage #1: para-thiocresol With potassium hydroxide In methanol at 70℃; for 0.25h; Inert atmosphere; Schlenk technique; Green chemistry;
Stage #2: 3,5-dimethylphenyl iodide With copper(l) iodide In methanol at 110℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;
100%
With 1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2λ5,4λ5-catenadi(phosphazene); copper(I) bromide In toluene Substitution; Heating;92%
With copper(l) iodide; 1,10-Phenanthroline In 1-methyl-pyrrolidin-2-one; methanol at 25℃; for 36h; Inert atmosphere;50%
With C15H16N3Ni(1+)*BF4(1-); sodium t-butanolate In acetonitrile at 100℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique;0.20 g
sodium ethanolate
141-52-6

sodium ethanolate

ethylene dibromide
106-93-4

ethylene dibromide

para-thiocresol
106-45-6

para-thiocresol

(2-ethoxyethyl)-para-thiocresol
57023-03-7

(2-ethoxyethyl)-para-thiocresol

Conditions
ConditionsYield
Stage #1: para-thiocresol With sodium ethanolate In ethanol at 20℃; Metallation;
Stage #2: ethylene dibromide In ethanol at 20℃; Alkylation;
Stage #3: sodium ethanolate In ethanol Substitution; Heating;
100%
para-thiocresol
106-45-6

para-thiocresol

2-chloro-ethanol
107-07-3

2-chloro-ethanol

(2-chloro-ethyl)-p-tolyl sulfide
20761-71-1

(2-chloro-ethyl)-p-tolyl sulfide

Conditions
ConditionsYield
Stage #1: para-thiocresol With sodium ethanolate In ethanol at 20℃; for 0.5h; Metallation;
Stage #2: 2-chloro-ethanol In ethanol for 3.5h; Alkylation; Heating;
Stage #3: With hydrogenchloride In ethanol; water Chlorination; 15 h, r.t., 4.5 h, reflux;
100%
N-(2-bromo-ethyl)-ethylenediamine; dihydrobromide
23545-41-7

N-(2-bromo-ethyl)-ethylenediamine; dihydrobromide

para-thiocresol
106-45-6

para-thiocresol

S-2-(2-aminoethylamino)ethyl 4-tolyl sulfide
115335-17-6

S-2-(2-aminoethylamino)ethyl 4-tolyl sulfide

Conditions
ConditionsYield
With triethylamine In chloroform at 0 - 5℃; for 3h;100%
N-(2-bromo-ethyl)-butanediyldiamine; dihydrobromide
23545-43-9

N-(2-bromo-ethyl)-butanediyldiamine; dihydrobromide

para-thiocresol
106-45-6

para-thiocresol

S-2-(4-aminobutylamino)ethyl 4-tolyl sulfide

S-2-(4-aminobutylamino)ethyl 4-tolyl sulfide

Conditions
ConditionsYield
With triethylamine In chloroform at 0 - 5℃; for 3h;100%
dibromohydrate du N-(bromoethyl-2)diamino-1,3 propane
23545-42-8

dibromohydrate du N-(bromoethyl-2)diamino-1,3 propane

para-thiocresol
106-45-6

para-thiocresol

S-2-(3-aminopropylamino)ethyl 4-tolyl sulfide

S-2-(3-aminopropylamino)ethyl 4-tolyl sulfide

Conditions
ConditionsYield
With triethylamine In chloroform at 0 - 5℃; for 3h;100%
2-phenyl-1,2-benzoisoselenazol-3(2H)-one
60940-34-3

2-phenyl-1,2-benzoisoselenazol-3(2H)-one

para-thiocresol
106-45-6

para-thiocresol

C20H17NOSSe

C20H17NOSSe

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h;100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

para-thiocresol
106-45-6

para-thiocresol

4-[(4-methylphenyl)thio]benzamide

4-[(4-methylphenyl)thio]benzamide

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With SPPSLRAM SynPhase Lanterns(R); N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 45℃; for 15h;
Stage #2: para-thiocresol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: With trifluoroacetic acid In dichloromethane
100%
4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

para-thiocresol
106-45-6

para-thiocresol

4-[(4-methylphenyl)thio]benzoic acid
22494-64-0

4-[(4-methylphenyl)thio]benzoic acid

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid With dmap; SPPSLHMP SynPhase Lanterns(R); dacarbazine In dichloromethane; N,N-dimethyl-formamide at 50℃; for 15h;
Stage #2: para-thiocresol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: With trifluoroacetic acid In dichloromethane
100%
3-iodo-4-toluic acid
82998-57-0

3-iodo-4-toluic acid

para-thiocresol
106-45-6

para-thiocresol

4-methyl-3-[(4-methylphenyl)thio]benzoic acid

4-methyl-3-[(4-methylphenyl)thio]benzoic acid

Conditions
ConditionsYield
Stage #1: 3-iodo-4-toluic acid With dmap; SPPSLHMP SynPhase Lanterns(R); dacarbazine In dichloromethane; N,N-dimethyl-formamide at 50℃; for 15h;
Stage #2: para-thiocresol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: With trifluoroacetic acid In dichloromethane
100%
4-iodo-3-methylbenzoic acid
52107-87-6

4-iodo-3-methylbenzoic acid

para-thiocresol
106-45-6

para-thiocresol

3-methyl-4-[(4-methylphenyl)thio]benzoic acid

3-methyl-4-[(4-methylphenyl)thio]benzoic acid

Conditions
ConditionsYield
Stage #1: 4-iodo-3-methylbenzoic acid With dmap; SPPSLHMP SynPhase Lanterns(R); dacarbazine In dichloromethane; N,N-dimethyl-formamide at 50℃; for 15h;
Stage #2: para-thiocresol With borohydride polymer supported Amberlite(R) IRA400; bis(bipyridine)nickel(II) bromide In tetrahydrofuran; ethanol at 70℃; for 15h;
Stage #3: With trifluoroacetic acid In dichloromethane
100%
crotonic acid methyl ester
623-43-8

crotonic acid methyl ester

para-thiocresol
106-45-6

para-thiocresol

4-(4-mercapto-phenyl)-3-methyl-butyric acid methyl ester

4-(4-mercapto-phenyl)-3-methyl-butyric acid methyl ester

Conditions
ConditionsYield
With magnesium oxide In toluene at 20℃; for 0.5h; Michael addition;100%
acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

para-thiocresol
106-45-6

para-thiocresol

3-(4-methylphenylsulfanyl)propionic acid methyl ester

3-(4-methylphenylsulfanyl)propionic acid methyl ester

Conditions
ConditionsYield
With sodium acetate In tetrahydrofuran; water at 25℃; for 18h;100%
With phosphotungstic acid In water at 20℃; for 2.5h; Michael addition;98%
In water at 30 - 35℃; for 0.25h; thia-Michael addition;95%
2-(4-bromophenyl)benzo[d][1,2]selenazol-3(2H)-one
944719-58-8

2-(4-bromophenyl)benzo[d][1,2]selenazol-3(2H)-one

para-thiocresol
106-45-6

para-thiocresol

C20H16NOSSeBr

C20H16NOSSeBr

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h;100%

106-45-6Relevant articles and documents

Palladium catalyzed synthesis of aryl thiols: Sodium thiosulfate as a cheap and nontoxic mercapto surrogate

Yi, Jun,Fu, Yao,Xiao, Bin,Cui, Wei-Chen,Guo, Qing-Xiang

, p. 205 - 208 (2011)

A Pd-catalyzed coupling reaction of ArBr/ArCl/ArOTf with sodium thiosulfate takes place in presence of Cs2CO3 at 80 °C. The reaction mixture is directly treated with Zn/HCl to afford aryl thiols in good to excellent yields.

-

Rudinger et al.

, p. 2216,2218 (1973)

-

Non-aqueous reduction of aromatic sulfonyl chlorides to thiols using a dichlorodimethylsilane-zinc-dimethylacetamide system

Uchiro, Hiromi,Kobayashi, Susumu

, p. 3179 - 3182 (1999)

A new and efficient method for the non-aqueous reduction of sulfonyl chlorides to affored the corresponding thiols by use of a dichlorodimethylsilane-zinc-dimethylacetamide system was successfully developed. Various aromatic thiols were prepared in high yield by easy operation. Continuous reactions with the above reduction using the prepared thiol were also demonstrated.

-

Troeger,Pape

, p. 217 (1926)

-

Copper-Catalyzed Direct Synthesis of Aryl Thiols from Aryl Iodides Using Sodium Sulfide Aided by Catalytic 1,2-Ethanedithiol

Xue, Hongyu,Jing, Bing,Liu, Shasha,Chae, Junghyun,Liu, Yajun

, p. 2272 - 2276 (2017)

A copper-catalyzed direct and effective synthesis of aryl thiols from aryl iodides using readily available Na 2 S·9H 2 O and 1,2-ethanedithiol was described. A variety of aryl thiols were readily obtained in yields of 76-99%. In this protocol, Na 2 S·9H 2 O was used as ultimate sulfur source, and 1,2-ethanedithiol functioned as an indispensable catalytic reagent.

Copper-catalyzed coupling of thiourea with aryl iodides: The direct synthesis of aryl thiols

Qiao, Shu,Xie, Kun,Qi, Junsheng

, p. 1441 - 1443 (2010)

A general, economical and efficient protocol for the direct copper-catalyzed coupling of thiourea with aryl iodides is developed and it will be potentially applied in large-scale industry as a preferred process.

IODINE CATALYZED REDUCTION OF ARENESULFONIC ACID TO THE ARENETHIOL WITH TRIPHENYLPHOSPHINE

Fujimori, Ken,Togo, Hideo,Oae, Shigeru

, p. 4921 - 4924 (1980)

Arenesulfonic acids, its sodium salts, and alkyl arenesulfonates were reduced readily to the corresponding arenethiols quantitatively with triphenylphosphine in the presence of iodine.

Catalytic transfer hydrogenation of aryl sulfo compounds

Chen, Xinzhi,Zhou, Shaodong,Qian, Chao

, p. 179 - 185 (2012)

A new method to reduce aryl sulfo compounds via transfer hydrogenation was investigated, using Pd/C as a catalyst, and 2-propanol or formic acid as hydrogen sources. This new process is simple and clean.

Thermal reactions of chloroarenes with hydrogen sulfide in the presence of methanol

Deryagina,Sukhomasova,Levanova,Papernaya,Korchevin

, p. 1624 - 1630 (2005)

Gas-phase reactions of chloroarenes (ClC6H4X, X = H, 4-CH3, 4-OH, 4-Cl, 4-CF3) with hydrogen sulfide or its precursors were investigated in the presence of methanol, which was a stronger H-donor than hydrogen sulfide. Introducing methanol increased the selectivity of arenethiols formation at X = H and 4-CH3 and did not affect the reaction selectivity at acceptor X. The efficiency of methanol influence was considered from the viewpoint of free-radical reaction mechanism and the stability of the arenethiyl radicals. 2005 Pleiades Publishing, Inc.

Metal–organic framework MOF-199-catalyzed direct and one-pot synthesis of thiols, sulfides and disulfides from aryl halides in wet polyethylene glycols (PEG 400)

Soleiman-Beigi, Mohammad,Sadeghizadeh, Fatemeh,Basereh, Ali

, p. 572 - 583 (2017)

A highly porous metal–organic frame work Cu3 BTC2 (copper(II)-benzene-1,3,5-tricarboxylate) that is known as MOF-199 was synthesized from the reaction of 1,3,5-benzenetricarboxylic acid and Cu(OAc)2·H2O by a solvothermal method and characterized by several techniques including FT-IR, XRD, EDX and scanning electron microscopy. The MOF-199 used as an efficient catalyst for one-pot synthesis of thiols by domino reactions of aryl halides and thiourea, and subsequently conversion to aryl alkyl sulfides and diaryl disulfides in polyethylene glycols (PEGs). A variety of aryl alkyl sulfides can be obtained in good to excellent yields in a relatively short reaction time and in the presence of the trace amount of catalyst. Also, the catalyst can be separated from the reaction mixture by decanting, and be reused without significant degradation in catalytic activity.

Synthesis method of substituted thiophenol (by machine translation)

-

Paragraph 0047-0049, (2020/06/09)

The invention provides a method for synthesizing substituted thiophenol, which comprises the following steps of preparing compound V compound and NaHSO3 Or KHHSO3 Reaction synthesis IV compound, compound of formula IV and SO2 Reaction-synthesis III compounds of formula III are passed NaBH in NaOH solution. 4 Of formula II is reduced and the compound of formula II is acidified to give a compound of formula I. The method for synthesizing the substituted thiophenol has the advantages of greenness, high efficiency, easiness in industrial application and the like. (by machine translation)

SINGLE-STEP SYNTHESIS METHOD OF ARYL THIOL AND APPLICATION THEREOF

-

Paragraph 0032; 0033; 0056-0060, (2017/09/02)

The present invention relates to a single-step synthesis method of aryl thiol, and more specifically, to a method of synthesizing aryl thiol in a single-step by making aryl halide react with alkane dithiol in the presence of a transition metal catalyst. According to the present invention, a single-step synthesis method using the transition metal catalyst, the synthesis method which is capable of synthesizing aryl thiol from aryl halide at a high yield, can be provided. Various aryl halides may be applied to the synthesis method. Further, the synthesis method has advantages that an easily usable reagent may be used, operations are simple, and reactions can be performed under mild conditions. In addition, the synthesized aryl thiol may be used in the synthesis of advanced molecules such as diaryl sulfides and benzothiophenes.COPYRIGHT KIPO 2017

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