• Name

  Cyanomethyl p-toluenesulfonate

• EINECS 238-604-3
• CAS No. 14562-04-0
• Density 1.29 g/cm³
• Solubility
• Melting Point 47 °C
• Formula C9H9 N O3 S
• Boiling Point 393.6 °C at 760 mmHg
• Molecular Weight 211.241
• Flash Point 191.9 °C
• Transport Information
• Appearance Colorless and transparent liquid
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms Acetonitrile,[[(4-methylphenyl)sulfonyl]oxy]- (9CI); Glycolonitrile, p-toluenesulfonate(7CI); Glycolonitrile, p-toluenesulfonate (ester) (8CI); Cyanomethyl4-methylbenzenesulfonate; Cyanomethyl p-toluenesulfonate; Cyanomethylp-tosylate; Cyanomethyl toluenesulfonate; Cyanomethyl tosylate;Toluene-4-sulfonic acid cyanomethyl ester
• PSA 75.54000
• LogP 2.30468

Synthetic route

50-00-0

formaldehyd

151-50-8

potassium cyanide

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

Conditions

Conditions	Yield
anschliessend mit Toluol-sulfonylchlorid-(4);

460-19-5

ethanedinitrile

98-59-9

p-toluenesulfonyl chloride

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

Conditions

Conditions	Yield
With sodium hydroxide In 1,2-dimethoxyethane; water	6.8 g (64% conversion)

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

503-20-8

fluoroacetonitrile

Conditions

Conditions	Yield
With fluorosilicate In ethylene glycol at 78℃; for 4h;	97.1%
With potassium fluoride; diethylene glycol

1072-72-6

Tetrahydrothiopyran-4-one

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

195503-40-3

tetrahydro-2H-thiopyrane-4-carbonitrile

Conditions

Conditions	Yield
With potassium tert-butylate In 1,2-dimethoxyethane; tert-butyl alcohol at 0 - 20℃; for 3h;	91%

927887-21-6

5-iodo-2-isopropyl-4-methoxy-phenol

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

927887-22-7

(5-iodo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran	90%
With potassium tert-butylate In tetrahydrofuran at 6 - 20℃;	81%
Stage #1: 5-iodo-2-isopropyl-4-methoxy-phenol With potassium tert-butylate In tetrahydrofuran at 1 - 6℃; Stage #2: toluene-4-sulfonic acid cyanomethyl ester In tetrahydrofuran at 20℃;	81%

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

88-75-5

2-hydroxynitrobenzene

31507-30-9

2-(2-nitrophenoxy)acetonitrile

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 20h; Reflux;	80%

2-amino-4-nitro-6-hydroxy(isopropylbenzene)

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

865305-39-1

(2-isopropyl-4-methoxy-5-nitro-phenoxy)-acetonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h;	76%

865305-37-9

2-isopropyl-4-methoxy-5-nitro-phenol

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

865305-39-1

(2-isopropyl-4-methoxy-5-nitro-phenoxy)-acetonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h;	76%

865305-44-8

5-Chloro-2-(1-hydroxy-1-methyl-ethyl)-4-methoxy-phenol

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

865305-45-9

C12H14ClNO3

Conditions

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 16h;	69%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	69%

16728-82-8

N-cyanomethyl-β-alanine nitrile

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

3-(bis-cyanomethyl-amino)-propionitrile; compound with toluene-4-sulfonic acid

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 50℃; for 120h;

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

591-27-5

m-Hydroxyaniline

219312-01-3

2-(3-aminophenoxy)acetonitrile

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide
With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide

N,N-dimethylformamide (DMF)

N,N-dimethylformamide (DMF)

3-amino-4-chloro-2-methyl-phenol

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

(3-amino-4-chloro-2-methylphenoxy)acetonitrile

Conditions

Conditions	Yield
In tetrahydrofuran; N,N-dimethyl-formamide
In tetrahydrofuran; N,N-dimethyl-formamide

...Expand

isopropanolic-HCl

isopropanolic-HCl

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

7568-93-6

2-Amino-1-phenylethanol

78443-54-6

dl-[(2-hydroxy-2-phenylethyl)amino]acetonitrile, hydrochloride

Conditions

Conditions	Yield
In diethyl ether; ethyl acetate

...Expand

13522-86-6

2-iso-propyl-4-methoxyphenol

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

2-(2-isopropyl-4-methoxyphenoxy)acetonitrile

Conditions

Conditions	Yield
With potassium carbonate In butanone at 55 - 60℃; for 114h; Heating / reflux;
With potassium carbonate In butanone at 55 - 60℃; for 114h; Heating / reflux;
With potassium carbonate In butanone at 55 - 60℃; for 114h; Heating / reflux;
With potassium carbonate In iso-butanol at 55 - 60℃; for 114h; Heating / reflux;
With potassium carbonate In butanone at 55 - 60℃; for 114h; Heating / reflux;

14562-04-0

toluene-4-sulfonic acid cyanomethyl ester

C20H17NO5S

C29H25NO5S2

C29H25NO5S2

Conditions

Conditions	Yield
With C39H38N3O2P; potassium carbonate; silver(l) oxide at 20℃; Overall yield = 55%; enantioselective reaction;	A n/a B n/a

...Expand

Cyanomethyl p-toluenesulfonate Chemical Properties