Product Name

  • Name

    2-(METHYLTHIO)BENZONITRILE

  • EINECS -0
  • CAS No. 6609-54-7
  • Article Data19
  • CAS DataBase
  • Density 1.14 g/cm3
  • Solubility Insoluble in water.
  • Melting Point 37-39 °C
  • Formula C8H7NS
  • Boiling Point 263.9 °C at 760 mmHg
  • Molecular Weight 149.216
  • Flash Point 113.4 °C
  • Transport Information
  • Appearance
  • Safety 36/37
  • Risk Codes 20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 6609-54-7 (2-(METHYLTHIO)BENZONITRILE)
  • Hazard Symbols R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.;
  • Synonyms Benzonitrile,o-(methylthio)- (7CI,8CI);2-(Methylthio)benzonitrile;2-Cyanophenyl methylsulfide;2-Methylsulfanylbenzonitrile;Methyl o-cyanophenyl sulfide;
  • PSA 49.09000
  • LogP 2.28018

Synthetic route

2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
With tetrabutylammomium bromide In water; chlorobenzene at 60 - 65℃; for 17h; Inert atmosphere;99%
With tetrabutylammomium bromide In water; chlorobenzene at 70 - 75℃; for 15h; Inert atmosphere;98%
2-fluorobenzonitrile
394-47-8

2-fluorobenzonitrile

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
In acetonitrile at 60℃; Inert atmosphere;99%
[(Z)-Hydroxyimino]-(2-methylsulfanyl-phenyl)-acetic acid methyl ester

[(Z)-Hydroxyimino]-(2-methylsulfanyl-phenyl)-acetic acid methyl ester

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
With acetic anhydride In pyridine for 24h; Heating;83%
N-cyano-N-phenyl-p-toluenesulfonamide
55305-43-6

N-cyano-N-phenyl-p-toluenesulfonamide

2-bromo-1-(methylsulfanyl)benzene
19614-16-5

2-bromo-1-(methylsulfanyl)benzene

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
Stage #1: 2-bromo-1-(methylsulfanyl)benzene With magnesium; lithium chloride In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: N-cyano-N-phenyl-p-toluenesulfonamide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;		75%
sodium cyanide
773837-37-9

sodium cyanide

2-(methylthio)iodobenzene
33775-94-9

2-(methylthio)iodobenzene

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
With C18H14CuIN4 In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; UV-irradiation;72%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

1-(methylsulfonyl)-2-(2-cyanophenyl)diazene

1-(methylsulfonyl)-2-(2-cyanophenyl)diazene

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
In acetonitrile at 20℃; for 12h; UV-irradiation;72%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

2-fluorobenzonitrile
394-47-8

2-fluorobenzonitrile

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
With potassium tert-butylate In acetonitrile at 50℃; for 6h; Sealed tube;63%
2-fluorobenzonitrile
394-47-8

2-fluorobenzonitrile

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In water at 189℃; for 24h;62%
2-chlorothioanisole
17733-22-1

2-chlorothioanisole

dicyanozinc
557-21-1

dicyanozinc

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
bis(tri-t-butylphosphine)palladium(0); zinc In N,N-dimethyl acetamide at 95℃; for 5h;56.1%
methyl magnesium iodide
917-64-6

methyl magnesium iodide

diethyl ether
60-29-7

diethyl ether

o-cyanophenyl thiocyanate
34263-66-6

o-cyanophenyl thiocyanate

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

...Expand
methyl magnesium iodide
917-64-6

methyl magnesium iodide

o-cyanophenyl thiocyanate
34263-66-6

o-cyanophenyl thiocyanate

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
With diethyl ether
o-cyanophenyl thiocyanate
34263-66-6

o-cyanophenyl thiocyanate

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
With potassium hydroxide; zinc nachfolgend Behandlung mit Dimethylsulfat;
2-methylsulfanyl-benzamide
54705-16-7

2-methylsulfanyl-benzamide

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
With diphosphorus pentasulfide; xylene
With phosphorus pentaoxide; xylene
2-(Methylthio)aniline
2987-53-3

2-(Methylthio)aniline

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
Diazotization.man setzt die Diazoniumsalzloesung bei 60-70grad mit Kaliumkupfercyanuer um;
2-cyanothiophenol
34761-11-0

2-cyanothiophenol

methyl iodide
74-88-4

methyl iodide

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

benzo-[b]thiophene-2,3-dione
493-57-2

benzo-[b]thiophene-2,3-dione

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: aq. sodium hydroxide (20percent) / 0.5 h
2: concentrated sulfuric acid / neat (no solvent) / 672 h
3: 90 percent / hydroxylamine hydrochloride / ethanol; pyridine / 4 h / Heating
4: 83 percent / acetic anhydride / pyridine / 24 h / Heating
View Scheme
(2-Methylsulfanyl-phenyl)-oxo-acetic acid

(2-Methylsulfanyl-phenyl)-oxo-acetic acid

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: concentrated sulfuric acid / neat (no solvent) / 672 h
2: 90 percent / hydroxylamine hydrochloride / ethanol; pyridine / 4 h / Heating
3: 83 percent / acetic anhydride / pyridine / 24 h / Heating
View Scheme
methyl 2-(2-methylthiophenyl)-2-oxoacetate
117136-70-6

methyl 2-(2-methylthiophenyl)-2-oxoacetate

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / hydroxylamine hydrochloride / ethanol; pyridine / 4 h / Heating
2: 83 percent / acetic anhydride / pyridine / 24 h / Heating
View Scheme
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 15 percent / potassium tert-butoxide / liquid ammonia / 90 h / Irradiation
View Scheme
Multi-step reaction with 2 steps
1: 100 percent Spectr. / potassium tert-butoxide / liquid ammonia / 60 h / Irradiation
View Scheme
Multi-step reaction with 2 steps
1: 85 percent / potassium tert-butoxide / liquid ammonia / 2 h / Irradiation
View Scheme
methyl 2-nitrophenyl sulfide
3058-47-7

methyl 2-nitrophenyl sulfide

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: zinc; concentrated hydrochloric acid
2: Diazotization.man setzt die Diazoniumsalzloesung bei 60-70grad mit Kaliumkupfercyanuer um
View Scheme
2-methylsulfanyl-benzoyl chloride
1442-03-1

2-methylsulfanyl-benzoyl chloride

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether; ammonia
2: phosphorus pentoxide; xylene
View Scheme
2-(methylthio)benzoic acid
3724-10-5

2-(methylthio)benzoic acid

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride
2: diethyl ether; ammonia
3: phosphorus pentoxide; xylene
View Scheme
anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Diazotization.Eintragen der Diazoloesung in eine Suspension von Kupfer(I)-rhodanid in Kaliumrhodanid-Loesung
2: alcoholic KOH-solution; zinc dust / nachfolgend Behandlung mit Dimethylsulfat
View Scheme
Multi-step reaction with 2 steps
1: Diazotization.Eintragen der Diazoloesung in eine Suspension von Kupfer(I)-rhodanid in Kaliumrhodanid-Loesung
2: diethyl ether
View Scheme
2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

methylthiol
74-93-1

methylthiol

chlorobenzene
108-90-7

chlorobenzene

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide; sodium In water
...Expand
2-cyano-benzenediazonium tetrafluoroborate
55165-45-2

2-cyano-benzenediazonium tetrafluoroborate

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane / 0 - 20 °C
2: acetonitrile / 12 h / 20 °C / UV-irradiation
View Scheme
methyl-phenyl-thioether
100-68-5

methyl-phenyl-thioether

phthalonitrile
91-15-6

phthalonitrile

A

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

B

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); 1,2-bis-(dicyclohexylphosphino)ethane In o-xylene at 140℃; for 24h;A n/a
B 7 %Chromat.
...Expand
2-cyanothioanisole
6609-54-7

2-cyanothioanisole

1,2-benzisothiazolin-3-one
2634-33-5

1,2-benzisothiazolin-3-one

Conditions
ConditionsYield
Stage #1: 2-cyanothioanisole With chlorine In water; chlorobenzene at 45 - 70℃; for 5h;
Stage #2: With water; sodium hydroxide In chlorobenzene at 65 - 70℃; Concentration; Time;		99%
Stage #1: 2-cyanothioanisole With hydrogenchloride; water; chlorine In chlorobenzene at 45 - 70℃; for 3h;
Stage #2: With water; sodium hydroxide In chlorobenzene at 65 - 70℃;		98%
Stage #1: 2-cyanothioanisole With chlorine In chlorobenzene at 40 - 80℃;
Stage #2: With sodium hydroxide In water at 60 - 70℃; pH=10 - 12;
Stage #3: With hydrogenchloride In water at 20 - 30℃; for 1h; pH=4 - 6;		90%
With hydrogenchloride; chlorine In water; chlorobenzene at 25 - 65℃; for 1.5h;90.8%
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

N-tert-butyl-o-(methylthio)benzamide
79054-71-0

N-tert-butyl-o-(methylthio)benzamide

Conditions
ConditionsYield
With sulfuric acid at 42℃; for 6h;90%
2-cyanothioanisole
6609-54-7

2-cyanothioanisole

isopropyl alcohol
67-63-0

isopropyl alcohol

2-isopropoxybenzonitrile
90921-35-0

2-isopropoxybenzonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;86%
(1S,2R,5S)-(+)-menthol
15356-60-2

(1S,2R,5S)-(+)-menthol

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

2-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)benzonitrile

2-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)benzonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;83%
2-cyanothioanisole
6609-54-7

2-cyanothioanisole

4-phenylcyclohexan-1-d-1-ol
109337-60-2

4-phenylcyclohexan-1-d-1-ol

2-((4-phenylcyclohexyl-1-d)oxy)benzonitrile

2-((4-phenylcyclohexyl-1-d)oxy)benzonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;81%
[bis(acetoxy)iodo]benzene
3240-34-4

[bis(acetoxy)iodo]benzene

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

((2-cyanophenyl)thio)methyl acetate

((2-cyanophenyl)thio)methyl acetate

Conditions
ConditionsYield
With (triphenylphosphine)gold(I) chloride In 1,2-dichloro-ethane at 130℃; Schlenk technique;80%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

2-(cyclobutylmethoxy)benzonitrile

2-(cyclobutylmethoxy)benzonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;78%
n-Pent-4-enyl alcohol
821-09-0

n-Pent-4-enyl alcohol

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

2-(pent-4-en-1-yloxy)benzonitrile

2-(pent-4-en-1-yloxy)benzonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;77%
2-cyanothioanisole
6609-54-7

2-cyanothioanisole

benzylamine
100-46-9

benzylamine

N-benzyl-2-(methylthio)benzimidamide

N-benzyl-2-(methylthio)benzimidamide

Conditions
ConditionsYield
With bis(trimethylaluminum)–1,4-diazabicyclo[2.2.2]octane adduct In tetrahydrofuran at 130℃; for 0.2h; Microwave irradiation; Inert atmosphere; Sealed tube;76%
4-phenyl-butan-1-ol
3360-41-6

4-phenyl-butan-1-ol

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

2-(4-phenylbutoxy)benzonitrile

2-(4-phenylbutoxy)benzonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;75%
(2S)-2-methyl-1-butanol
1565-80-6

(2S)-2-methyl-1-butanol

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

(S)-(+)-2-(2-methylbutyloxy)benzonitrile

(S)-(+)-2-(2-methylbutyloxy)benzonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;71%
2-cyanothioanisole
6609-54-7

2-cyanothioanisole

ethyl acetoacetate
141-97-9

ethyl acetoacetate

ethyl (Z)-2-(amino(2-(methylthio)phenyl)methylene)-3-oxobutanoate

ethyl (Z)-2-(amino(2-(methylthio)phenyl)methylene)-3-oxobutanoate

Conditions
ConditionsYield
With titanium tetrachloride In toluene for 2h; Reflux;70.8%
(S)-valinol
2026-48-4

(S)-valinol

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

(4S)-4-Isopropyl-2-<2-(methylsulfanyl)phenyl>-4,5-dihydro-1,3-oxazole
154132-42-0

(4S)-4-Isopropyl-2-<2-(methylsulfanyl)phenyl>-4,5-dihydro-1,3-oxazole

Conditions
ConditionsYield
zinc(II) chloride In chlorobenzene for 48h; Heating;69%
With zinc(II) chloride In chlorobenzene for 48h; Heating;56%
2-cyanothioanisole
6609-54-7

2-cyanothioanisole

N-Cyanoguanidine
127099-85-8, 780722-26-1

N-Cyanoguanidine

6-(2-(methylthio)phenyl)-1,3,5-triazine-2,4-diamine

6-(2-(methylthio)phenyl)-1,3,5-triazine-2,4-diamine

Conditions
ConditionsYield
With potassium hydroxide In 2-ethoxy-ethanol at 130 - 135℃; for 10h;68%
(S)-Alaninol
2749-11-3

(S)-Alaninol

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

(4S)-2-((2-methylthio)phenyl)-4-methyl-1,3-oxazoline

(4S)-2-((2-methylthio)phenyl)-4-methyl-1,3-oxazoline

Conditions
ConditionsYield
With zinc(II) chloride In chlorobenzene for 48h; Heating;60%
zinc(II) chloride In chlorobenzene for 48h; Heating;60%
2-cyanothioanisole
6609-54-7

2-cyanothioanisole

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

(4S)-2-[2-(methylsulfanyl)phenyl]-4-phenyl-4,5-dihydro-1,3-oxazole
154132-43-1

(4S)-2-[2-(methylsulfanyl)phenyl]-4-phenyl-4,5-dihydro-1,3-oxazole

Conditions
ConditionsYield
With zinc(II) chloride In chlorobenzene for 48h; Heating;58%
zinc(II) chloride In chlorobenzene for 48h; Heating;58%
2-cyanothioanisole
6609-54-7

2-cyanothioanisole

(1S,2S)-2-amino-1-phenyl-1,3-diol
28143-91-1

(1S,2S)-2-amino-1-phenyl-1,3-diol

[(4S,5S)-2-(2-Methylsulfanyl-phenyl)-5-phenyl-4,5-dihydro-oxazol-4-yl]-methanol
160246-26-4

[(4S,5S)-2-(2-Methylsulfanyl-phenyl)-5-phenyl-4,5-dihydro-oxazol-4-yl]-methanol

Conditions
ConditionsYield
With potassium carbonate In ethylene glycol; glycerol at 110℃; for 17h;55%
With potassium carbonate In ethylene glycol; glycerol at 115℃; for 18h;47%
2-cyanothioanisole
6609-54-7

2-cyanothioanisole

5-bromo-2-fluorobenzonitrile
391200-05-8

5-bromo-2-fluorobenzonitrile

Conditions
ConditionsYield
With N-Bromosuccinimide; tetrafluoroboric acid dimethyl ether complex In acetonitrile55%
2-cyanothioanisole
6609-54-7

2-cyanothioanisole

(S)-tert-leucinol
112245-13-3

(S)-tert-leucinol

(4S)-4-tert-butyl-2-((2-methylthio)phenyl)-1,3-oxazoline

(4S)-4-tert-butyl-2-((2-methylthio)phenyl)-1,3-oxazoline

Conditions
ConditionsYield
With zinc(II) chloride In chlorobenzene for 48h; Heating;53%
zinc(II) chloride In chlorobenzene for 48h; Heating;53%
4-hexyn-1-ol
928-93-8

4-hexyn-1-ol

2-cyanothioanisole
6609-54-7

2-cyanothioanisole

2-(hex-4-yn-1-yloxy)benzonitrile

2-(hex-4-yn-1-yloxy)benzonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;50%
2-cyanothioanisole
6609-54-7

2-cyanothioanisole

L-Phenylalaninol
3182-95-4

L-Phenylalaninol

(4S)-4-benzyl-2-((2-methylthio)phenyl)-1,3-oxazoline

(4S)-4-benzyl-2-((2-methylthio)phenyl)-1,3-oxazoline

Conditions
ConditionsYield
With zinc(II) chloride In chlorobenzene for 48h; Heating;42%
zinc(II) chloride In chlorobenzene for 48h; Heating;42%

Benzonitrile,2-(methylthio)- Specification

The Benzonitrile,2-(methylthio)-, with the CAS registry number 6609-54-7, is also known as 2-(Methylthio)benzonitrile. This chemical's molecular formula is C8H7NS and molecular weight is 149.21288. Its IUPAC name is called 2-methylsulfanylbenzonitrile.

Physical properties of Benzonitrile,2-(methylthio)-: (1)ACD/LogP: 2.34; (2)ACD/LogD (pH 5.5): 2.34; (3)ACD/LogD (pH 7.4): 2.34; (4)ACD/BCF (pH 5.5): 35.41; (5)ACD/BCF (pH 7.4): 35.41; (6)ACD/KOC (pH 5.5): 447.2; (7)ACD/KOC (pH 7.4): 447.2; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.589; (11)Molar Refractivity: 43.95 cm3; (12)Molar Volume: 130.3 cm3; (13)Surface Tension: 48.3 dyne/cm; (14)Density: 1.14 g/cm3; (15)Flash Point: 113.4 °C; (16)Enthalpy of Vaporization: 50.18 kJ/mol; (17)Boiling Point: 263.9 °C at 760 mmHg; (18)Vapour Pressure: 0.00999 mmHg at 25°C.

Preparation: this chemical can be prepared by hydroxyimino-(2-methylsulfanyl-phenyl)-acetic acid methyl ester. This reaction will need reagent acetic anhydride and solvent pyridine. The reaction time is 24 hours. The yield is about 83%.

Uses of Benzonitrile,2-(methylthio)-: it can be used to produce (4S)-2-((2-methylthio)phenyl)-4-methyl-1,3-oxazoline by heating. This reaction will need reagent ZnCl2 and solvent chlorobenzene with reaction time of 48 hours. The yield is about 60%.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. Whenever you will contact it, please wear suitable protective clothing and gloves.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CSC1=CC=CC=C1C#N
(2)InChI: InChI=1S/C8H7NS/c1-10-8-5-3-2-4-7(8)6-9/h2-5H,1H3
(3)InChIKey: PXZSANDJGNKIIA-UHFFFAOYSA-N

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