14562-04-0

Basic information

• Product Name: Cyanomethyl p-toluenesulfonate
• Synonyms: (tosyloxy)acetonitrile;Cyanomethyl p-toluenesulphonate;CyanomethylP-Toluenesulfonate;[[(4-Methylphenyl)sulfonyl]oxy]acetonitrile;Cyanomethyl 4-methylbenzenesulfonate
• CAS NO: 14562-04-0
• Molecular Formula: C₉H₉NO₃S
• Molecular Weight: 211.24
• EINECS: 238-604-3
• Product Categories: COOR
• Mol File: 14562-04-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 47 °C
• Boiling Point: 393.6 °C at 760 mmHg
• Flash Point: 191.9 °C
• Appearance: Colorless and transparent liquid
• Density: 1.29 g/cm³
• Vapor Pressure: 2.1E-06mmHg at 25°C
• Refractive Index: 1.537
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Cyanomethyl p-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Cyanomethyl p-toluenesulfonate(14562-04-0)
• EPA Substance Registry System: Cyanomethyl p-toluenesulfonate(14562-04-0)

Safety Data

• Hazardous Substances Data: 14562-04-0(Hazardous Substances Data)

Usage

General Description

Cyanomethyl p-toluenesulfonate is a chemical compound with the formula C9H10NO3S. It is an organic compound that is commonly used as a reagent in organic synthesis and pharmaceutical research. Cyanomethyl p-toluenesulfonate is a clear, colorless to pale yellow liquid with a pungent odor. It is highly reactive and has been found to be an effective reagent in the synthesis of various organic compounds. Additionally, cyanomethyl p-toluenesulfonate is used as a coupling agent in peptide and protein chemistry, and as a reagent for the protection of hydroxyl groups in organic synthesis. It is important to handle this compound with caution as it is toxic and can cause irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C9H9NO3S/c1-8-2-4-9(5-3-8)14(11,12)13-7-6-10/h2-5H,7H2,1H3

Synthetic route

formaldehyd (50-00-0) + potassium cyanide (151-50-8) → toluene-4-sulfonic acid cyanomethyl ester (14562-04-0)

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

ethanedinitrile (460-19-5) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid cyanomethyl ester (14562-04-0)

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

toluene-4-sulfonic acid cyanomethyl ester (14562-04-0) → fluoroacetonitrile (503-20-8)

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

Tetrahydrothiopyran-4-one (1072-72-6) + toluene-4-sulfonic acid cyanomethyl ester (14562-04-0) → tetrahydro-2H-thiopyrane-4-carbonitrile (195503-40-3)

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

5-iodo-2-isopropyl-4-methoxy-phenol (927887-21-6) + toluene-4-sulfonic acid cyanomethyl ester (14562-04-0) → (5-iodo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile (927887-22-7)

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%

toluene-4-sulfonic acid cyanomethyl ester (14562-04-0) + 2-hydroxynitrobenzene (88-75-5) → 2-(2-nitrophenoxy)acetonitrile (31507-30-9)

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

2-amino-4-nitro-6-hydroxy(isopropylbenzene) + toluene-4-sulfonic acid cyanomethyl ester (14562-04-0) → (2-isopropyl-4-methoxy-5-nitro-phenoxy)-acetonitrile (865305-39-1)

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

2-isopropyl-4-methoxy-5-nitro-phenol (865305-37-9) + toluene-4-sulfonic acid cyanomethyl ester (14562-04-0) → (2-isopropyl-4-methoxy-5-nitro-phenoxy)-acetonitrile (865305-39-1)

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

5-Chloro-2-(1-hydroxy-1-methyl-ethyl)-4-methoxy-phenol (865305-44-8) + toluene-4-sulfonic acid cyanomethyl ester (14562-04-0) → C12H14ClNO3 (865305-45-9)

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%

N-cyanomethyl-β-alanine nitrile (16728-82-8) + toluene-4-sulfonic acid cyanomethyl ester (14562-04-0) → 3-(bis-cyanomethyl-amino)-propionitrile; compound with toluene-4-sulfonic acid

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

toluene-4-sulfonic acid cyanomethyl ester (14562-04-0) + m-Hydroxyaniline (591-27-5) → 2-(3-aminophenoxy)acetonitrile (219312-01-3)

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) + 3-amino-4-chloro-2-methyl-phenol + toluene-4-sulfonic acid cyanomethyl ester (14562-04-0) → (3-amino-4-chloro-2-methylphenoxy)acetonitrile

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

isopropanolic-HCl + toluene-4-sulfonic acid cyanomethyl ester (14562-04-0) + 2-Amino-1-phenylethanol (7568-93-6) → dl-[(2-hydroxy-2-phenylethyl)amino]acetonitrile, hydrochloride (78443-54-6)

Conditions	Yield
In diethyl ether; ethyl acetate

2-iso-propyl-4-methoxyphenol (13522-86-6) + toluene-4-sulfonic acid cyanomethyl ester (14562-04-0) → 2-(2-isopropyl-4-methoxyphenoxy)acetonitrile

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;

toluene-4-sulfonic acid cyanomethyl ester (14562-04-0) + C20H17NO5S → C29H25NO5S2 + C29H25NO5S2

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

Upstream product

• 460-19-5 ethanedinitrile 
• 98-59-9 p-toluenesulfonyl chloride 
• 50-00-0 formaldehyd 
• 151-50-8 potassium cyanide 

Downstream Products

• 927887-22-7 (5-iodo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile 
• 31507-30-9 2-(2-nitrophenoxy)acetonitrile 
• 865305-39-1 (2-isopropyl-4-methoxy-5-nitro-phenoxy)-acetonitrile 
• 195503-40-3 tetrahydro-2H-thiopyrane-4-carbonitrile 
• 927872-64-8 2-(2-isopropyl-4-methoxyphenoxy)acetonitrile 
• 78443-54-6 dl-[(2-hydroxy-2-phenylethyl)amino]acetonitrile, hydrochloride 
• 219312-01-3 2-(3-aminophenoxy)acetonitrile 
• 503-20-8 fluoroacetonitrile 
• 865305-45-9 C₁₂H₁₄ClNO₃ 

Relevant articles and documents

Method of protecting plants from pathogens with cyanomethyl aryl sulfonates

Fungi or bacteria pathogenic to plants are inhibited by applying to the locus to be protected therefrom a biocidally effective amount of a cyanomethyl arylsulfonate represented by the formula RSO3 CH2 CN where R is STR1