6609-54-7

Basic information

• Product Name: 2-(METHYLTHIO)BENZONITRILE
• Synonyms: 2-(METHYLTHIO)BENZONITRILE;2-Cyanothioanisole~2-(Methylmercapto)benzonitrile;o-(Methylthio)benzonitrile;2-(Methylmercapto)benzonitrile;2-Cyanothioanisole;2-(METHYLTHIO)BENZONITRILE / 2-CYANOTHIOANISOLE;Benzonitrile, 2-(Methylthio)-
• CAS NO: 6609-54-7
• Molecular Formula: C₈H₇NS
• Molecular Weight: 149.21
• EINECS: -0
• Mol File: 6609-54-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 37-39°C
• Boiling Point: 116-117°C 5mm
• Flash Point: 116-117°C/5mm
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 0.00999mmHg at 25°C
• Refractive Index: 1.589
• Water Solubility: Insoluble in water.
• BRN: 2207135
• CAS DataBase Reference: 2-(METHYLTHIO)BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(METHYLTHIO)BENZONITRILE(6609-54-7)
• EPA Substance Registry System: 2-(METHYLTHIO)BENZONITRILE(6609-54-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 36/37
• RIDADR: 3439
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 6609-54-7(Hazardous Substances Data)

Usage

Uses

2-(Methylthio)benzonitrile is used as pharmaceutical intermediate.

InChI:InChI=1/C8H7NS/c1-10-8-5-3-2-4-7(8)6-9/h2-5H,1H3

Synthetic route

2-Chlorobenzonitrile (873-32-5) + sodium thiomethoxide (5188-07-8) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
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) + sodium thiomethoxide (5188-07-8) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
In acetonitrile at 60℃; Inert atmosphere;	99%

[(Z)-Hydroxyimino]-(2-methylsulfanyl-phenyl)-acetic acid methyl ester → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
With acetic anhydride In pyridine for 24h; Heating;	83%

N-cyano-N-phenyl-p-toluenesulfonamide (55305-43-6) + 2-bromo-1-(methylsulfanyl)benzene (19614-16-5) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
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) + 2-(methylthio)iodobenzene (33775-94-9) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
With C18H14CuIN4 In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; UV-irradiation;	72%

Dimethyldisulphide (624-92-0) + 1-(methylsulfonyl)-2-(2-cyanophenyl)diazene → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
In acetonitrile at 20℃; for 12h; UV-irradiation;	72%

Dimethyldisulphide (624-92-0) + 2-fluorobenzonitrile (394-47-8) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
With potassium tert-butylate In acetonitrile at 50℃; for 6h; Sealed tube;	63%

2-fluorobenzonitrile (394-47-8) + dimethyl sulfoxide (67-68-5) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In water at 189℃; for 24h;	62%

2-chlorothioanisole (17733-22-1) + dicyanozinc (557-21-1) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
bis(tri-t-butylphosphine)palladium(0); zinc In N,N-dimethyl acetamide at 95℃; for 5h;	56.1%

methyl magnesium iodide (917-64-6) + diethyl ether (60-29-7) + o-cyanophenyl thiocyanate (34263-66-6) → 2-cyanothioanisole (6609-54-7)

methyl magnesium iodide (917-64-6) + o-cyanophenyl thiocyanate (34263-66-6) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
With diethyl ether

o-cyanophenyl thiocyanate (34263-66-6) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
With potassium hydroxide; zinc nachfolgend Behandlung mit Dimethylsulfat;

2-methylsulfanyl-benzamide (54705-16-7) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
With diphosphorus pentasulfide; xylene
With phosphorus pentaoxide; xylene

2-(Methylthio)aniline (2987-53-3) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
Diazotization.man setzt die Diazoniumsalzloesung bei 60-70grad mit Kaliumkupfercyanuer um;

2-cyanothiophenol (34761-11-0) + methyl iodide (74-88-4) → 2-cyanothioanisole (6609-54-7)

benzo-[b]thiophene-2,3-dione (493-57-2) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
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-cyanothioanisole (6609-54-7)

Conditions	Yield
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) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
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) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
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) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
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-cyanothioanisole (6609-54-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether; ammonia 2: phosphorus pentoxide; xylene View Scheme

2-(methylthio)benzoic acid (3724-10-5) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
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) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
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) + methylthiol (74-93-1) + chlorobenzene (108-90-7) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide; sodium In water

2-cyano-benzenediazonium tetrafluoroborate (55165-45-2) → 2-cyanothioanisole (6609-54-7)

Conditions	Yield
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) + phthalonitrile (91-15-6) → 2-cyanothioanisole (6609-54-7) + benzonitrile (100-47-0)

Conditions	Yield
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.

2-cyanothioanisole (6609-54-7) → 1,2-benzisothiazolin-3-one (2634-33-5)

Conditions	Yield
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) + 2-cyanothioanisole (6609-54-7) → N-tert-butyl-o-(methylthio)benzamide (79054-71-0)

Conditions	Yield
With sulfuric acid at 42℃; for 6h;	90%

2-cyanothioanisole (6609-54-7) + isopropyl alcohol (67-63-0) → 2-isopropoxybenzonitrile (90921-35-0)

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;	86%

(1S,2R,5S)-(+)-menthol (15356-60-2) + 2-cyanothioanisole (6609-54-7) → 2-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)benzonitrile

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;	83%

2-cyanothioanisole (6609-54-7) + 4-phenylcyclohexan-1-d-1-ol (109337-60-2) → 2-((4-phenylcyclohexyl-1-d)oxy)benzonitrile

Conditions	Yield
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) + 2-cyanothioanisole (6609-54-7) → ((2-cyanophenyl)thio)methyl acetate

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

cyclobutanemethanol (4415-82-1) + 2-cyanothioanisole (6609-54-7) → 2-(cyclobutylmethoxy)benzonitrile

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;	78%

n-Pent-4-enyl alcohol (821-09-0) + 2-cyanothioanisole (6609-54-7) → 2-(pent-4-en-1-yloxy)benzonitrile

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;	77%

2-cyanothioanisole (6609-54-7) + benzylamine (100-46-9) → N-benzyl-2-(methylthio)benzimidamide

Conditions	Yield
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) + 2-cyanothioanisole (6609-54-7) → 2-(4-phenylbutoxy)benzonitrile

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;	75%

(2S)-2-methyl-1-butanol (1565-80-6) + 2-cyanothioanisole (6609-54-7) → (S)-(+)-2-(2-methylbutyloxy)benzonitrile

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;	71%

2-cyanothioanisole (6609-54-7) + ethyl acetoacetate (141-97-9) → ethyl (Z)-2-(amino(2-(methylthio)phenyl)methylene)-3-oxobutanoate

Conditions	Yield
With titanium tetrachloride In toluene for 2h; Reflux;	70.8%

(S)-valinol (2026-48-4) + 2-cyanothioanisole (6609-54-7) → (4S)-4-Isopropyl-2-<2-(methylsulfanyl)phenyl>-4,5-dihydro-1,3-oxazole (154132-42-0)

Conditions	Yield
zinc(II) chloride In chlorobenzene for 48h; Heating;	69%
With zinc(II) chloride In chlorobenzene for 48h; Heating;	56%

2-cyanothioanisole (6609-54-7) + N-Cyanoguanidine (127099-85-8, 780722-26-1) → 6-(2-(methylthio)phenyl)-1,3,5-triazine-2,4-diamine

Conditions	Yield
With potassium hydroxide In 2-ethoxy-ethanol at 130 - 135℃; for 10h;	68%

(S)-Alaninol (2749-11-3) + 2-cyanothioanisole (6609-54-7) → (4S)-2-((2-methylthio)phenyl)-4-methyl-1,3-oxazoline

Conditions	Yield
With zinc(II) chloride In chlorobenzene for 48h; Heating;	60%
zinc(II) chloride In chlorobenzene for 48h; Heating;	60%

2-cyanothioanisole (6609-54-7) + (2S)-2-phenylglycinol (20989-17-7) → (4S)-2-[2-(methylsulfanyl)phenyl]-4-phenyl-4,5-dihydro-1,3-oxazole (154132-43-1)

Conditions	Yield
With zinc(II) chloride In chlorobenzene for 48h; Heating;	58%
zinc(II) chloride In chlorobenzene for 48h; Heating;	58%

2-cyanothioanisole (6609-54-7) + (1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → [(4S,5S)-2-(2-Methylsulfanyl-phenyl)-5-phenyl-4,5-dihydro-oxazol-4-yl]-methanol (160246-26-4)

Conditions	Yield
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) → 5-bromo-2-fluorobenzonitrile (391200-05-8)

Conditions	Yield
With N-Bromosuccinimide; tetrafluoroboric acid dimethyl ether complex In acetonitrile	55%

2-cyanothioanisole (6609-54-7) + (S)-tert-leucinol (112245-13-3) → (4S)-4-tert-butyl-2-((2-methylthio)phenyl)-1,3-oxazoline

Conditions	Yield
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) + 2-cyanothioanisole (6609-54-7) → 2-(hex-4-yn-1-yloxy)benzonitrile

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;	50%

2-cyanothioanisole (6609-54-7) + L-Phenylalaninol (3182-95-4) → (4S)-4-benzyl-2-((2-methylthio)phenyl)-1,3-oxazoline

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

Upstream product

• 2987-53-3 2-(Methylthio)aniline 
• 873-32-5 2-Chlorobenzonitrile 
• 74-93-1 methylthiol 
• 108-90-7 chlorobenzene 
• 5188-07-8 sodium thiomethoxide 
• 773837-37-9 sodium cyanide 
• 33775-94-9 2-(methylthio)iodobenzene 
• 917-64-6 methyl magnesium iodide 
• 34263-66-6 o-cyanophenyl thiocyanate 
• 60-29-7 diethyl ether 
• 100-68-5 methyl-phenyl-thioether 
• 91-15-6 phthalonitrile 
• 624-92-0 Dimethyldisulphide 
• 394-47-8 2-fluorobenzonitrile 

Downstream Products

• 79054-71-0 N-tert-butyl-o-(methylthio)benzamide 
• 2634-33-5 1,2-benzisothiazolin-3-one 
• 184169-44-6 2-cyanobenzenesulfenyl bromide 
• 5188-07-8 sodium thiomethoxide 
• 90921-35-0 2-isopropoxybenzonitrile 
• 766-92-7 [(methylthio)methyl]-benzene 
• 3724-10-5 2-(methylthio)benzoic acid 
• 52369-06-9 2-methylsulfanyl-thiobenzoic acid amide 
• 34825-99-5 2-(diphenylphosphanyl)benzonitrile 
• 7716-66-7 3-chloro-1,2-benzisothiazole 

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