529-19-1

Basic information

• Product Name: o-Tolunitrile
• Synonyms: O-CYANO TOLUENE;LABOTEST-BB LT01273178;2-CYANOTOLUENE;2-TOLUNITRILE;2-METHYLBENZENECARBONITRILE;2-METHYLBENZONITRILE;2-Methylbenzonitrile/o-Tolunitrile;o-toluenenitrile
• CAS NO: 529-19-1
• Molecular Formula: C₈H₇N
• Molecular Weight: 117.15
• EINECS: 208-451-7
• Product Categories: Aromatic Nitriles
• Mol File: 529-19-1.mol
• Article Data: 257

Chemical Properties

• Melting Point: -13 °C
• Boiling Point: 205 °C(lit.)
• Flash Point: 184 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.989 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.243mmHg at 25°C
• Refractive Index: n20/D 1.5279(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Explosive Limit: 1.1-6.7%(V)
• Water Solubility: <0.1 g/100 mL at 17℃
• Merck: 14,9537
• BRN: 1857417
• CAS DataBase Reference: o-Tolunitrile(CAS DataBase Reference)
• NIST Chemistry Reference: o-Tolunitrile(529-19-1)
• EPA Substance Registry System: o-Tolunitrile(529-19-1)

Safety Data

• Hazard Codes: Xi
• Statements: 38-52/53-36/37/38
• Safety Statements: 61-37-36-26-24/25
• RIDADR: 3276
• WGK Germany: 2
• RTECS: XV0600000
• TSCA: Yes
• Hazardous Substances Data: 529-19-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Uses

o-Tolyl Cyanide, is a versatile intermediate, used in the synthesis of various pharmaceutical and biologically active compounds. It can be used in the preparation of highly efficient triarylene conjugated dyes for sensitized solar cells

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 2948, 1995 DOI: 10.1021/jo00114a060

General Description

Light blue clear liquid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Nitriles, such as o-Tolunitrile, may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Fire Hazard

o-Tolunitrile is combustible.

Purification Methods

Fractionally distil the nitrile, wash it with conc HCl or 50% H2SO4 at 60o until the smell of isonitrile has gone (this also removes any amines), then wash it with saturated NaHCO3 and dilute NaCl solutions, then dry it with K2CO3 and redistil it. [Beilstein 9 IV 1703.]

InChI:InChI=1/C8H7N/c1-7-4-2-3-5-8(7)6-9/h2-5H,1H3

Upstream product

• 4943-59-3 N-o-tolyl-formimidic acid ethyl ester 
• 614-69-7 2-tolyl isothiocyanate 
• 60-29-7 diethyl ether 
• 460-19-5 ethanedinitrile 
• 6921-34-2 benzylmagnesium chloride 
• 22627-00-5 2-methyl-benzophenone-imine 
• 64380-54-7 2-(2-methylphenyl)-1,3-dioxolane 
• 22115-41-9 2-(bromomethyl)benzonitrile 
• 89-93-0 ortho-methylbenzylamine 
• 447-60-9 2-(trifluoromethyl)benzonitrile 
• 104-85-8 para-methylbenzonitrile 
• 620-22-4 3-Methylbenzonitrile 
• 110-05-4 di-tert-butyl peroxide 
• 100-47-0 benzonitrile 

Downstream Products

• 577-16-2 2-Methylacetophenone 
• 91817-68-4 N-[(2-methylphenyl)methyl]acetamide 
• 153657-11-5 2-diacetoxymethyl-benzonitrile 
• 32959-60-7 2-(2-methylphenyl)-1,3-benzoxazole 
• 16216-13-0 2-phenyl-1-o-tolylethanone 
• 103987-46-8 2-methyl-N-thiazol-2-yl-benzamidine 
• 108897-24-1 4,4,6-trimethyl-2-o-tolyl-5,6-dihydro-4H-[1,3]oxazine 
• 69143-35-7 Aethyl-2-imino-1-methyl-2-(o-tolyl)aethylsulfon 
• 57027-68-6 2-hydroxyethyl 2-methylbenzoate 
• 132635-67-7 2-Methyl-N-pyrimidin-2-yl-benzamidine 
• 132635-70-2 N-(5-Chloro-pyrimidin-2-yl)-2-methyl-benzamidine 
• 132635-73-5 N-(5-Bromo-pyrimidin-2-yl)-2-methyl-benzamidine 
• 60695-59-2 2-cyclohexylmethyl-1-{2-[3-(2-methylbenzoyl)phenyl]propyl}piperidine 
• 132713-49-6 1-(2-benzothiazolyl)-3,5-di-(o-tolyl)-1H-s-triazole 

Relevant articles and documents

Cyanide-Free Cyanation of sp2 and sp-Carbon Atoms by an Oxazole-Based Masked CN Source Using Flow Microreactors

This work reports a cyanide-free continuous-flow process for cyanation of sp2 and sp carbons to synthesize aryl, vinyl and acetylenic nitriles from (5-methyl-2-phenyloxazol-4-yl) boronic acid [OxBA] reagent as a sole source of carbon-bound mask

Cu2O-Catalyzed Conversion of Benzyl Alcohols Into Aromatic Nitriles via the Complete Cleavage of the C≡N Triple Bond in the Cyanide Anion

Nitrogen transfer from cyanide anion to an aldehyde is emerging as a promising method for the synthesis of aromatic nitriles. However, this method still suffers from a disadvantage that a use of stoichiometric Cu(II) or Cu(I) salts is required to enable the reaction. As we report herein, we overcame this drawback and developed a catalytic method for nitrogen transfer from cyanide anion to an alcohol via the complete cleavage of the C≡N triple bond using phen/Cu2O as the catalyst. The present condition allowed a series of benzyl alcohols to be smoothly converted into aromatic nitriles in moderate to high yields. In addition, the present method could be extended to the conversion of cinnamic alcohol to 3-phenylacrylonitrile.

H3PO4 catalyzed one-pot synthesis of 1,3-diphenyl-1H-pyrazole-4-carbaldehyde to novel 1,3-diphenyl-1H-pyrazole-4-carbonitrile

Abstract: One-pot condensation of pyrazole-4-aldehydes and hydroxylamine hydrochloride to form the corresponding oxime using formic acid as a medium and further dehydration of oxime using a catalytic amount of orthophosphoric acid to afford novel pyrazole-4-carbonitrile. This protocol serves as an ortho-phosphoric acid-catalyzed one-pot conversion of aldehyde to nitrile. Most remarkable features of this method are metal-free, cost-effective, atom efficiency with excellent yield (98–99%). This process will serve as a robust and scalable tool for the synthesis of valuable and versatile precursor (nitriles). This precursor will pave the way for the synthesis of various medicinally important valuable compounds. Graphic abstract: [Figure not available: see fulltext.].