13730-09-1

Basic information

• Product Name: 2,5-DIMETHYLBENZONITRILE
• Synonyms: 2,5-dimethylbenzonitril;2,5-dimethyl-benzonitril;Benzonitrile, 2,5-dimethyl-;2,5-Dimethylbenzonitrile ,98%;2,5-DIMETHYLBENZONITRILE
• CAS NO: 13730-09-1
• Molecular Formula: C₉H₉N
• Molecular Weight: 131.17
• EINECS: 237-297-3
• Mol File: 13730-09-1.mol
• Article Data: 25

Chemical Properties

• Melting Point: 13 °C
• Boiling Point: 226.1 °C at 760 mmHg
• Flash Point: 95.7 °C
• Appearance: /
• Density: 0.99 g/cm³
• Vapor Pressure: 0.0831mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 2,5-DIMETHYLBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIMETHYLBENZONITRILE(13730-09-1)
• EPA Substance Registry System: 2,5-DIMETHYLBENZONITRILE(13730-09-1)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22
• Safety Statements: 26-36/37/39
• RIDADR: 3276
• HazardClass: IRRITANT-HARMFUL
• Hazardous Substances Data: 13730-09-1(Hazardous Substances Data)

Usage

General Description

2,5-Dimethylbenzonitrile, also known as 1,6-Dicyan-2,5-hexadiene, is a chemical compound with the molecular formula C9H9N. It is a colorless, clear liquid with a faint odor, and it is commonly used as a reagent in organic synthesis. 2,5-Dimethylbenzonitrile is also used in the production of pharmaceuticals, dyes, and other fine chemicals. While it is not known to be particularly hazardous, exposure to this chemical should be minimized due to its potential to cause irritation to the skin, eyes, and respiratory system. It should be handled with appropriate safety precautions and in a well-ventilated area.

InChI:InChI=1/C9H9N/c1-7-3-4-8(2)9(5-7)6-10/h3-5H,1-2H3

Upstream product

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• 202522-21-2 (2,5-dimethylphenyl)carboaldoxime 
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• 625-86-5 2,5-dimethylfuran 
• 107-13-1 acrylonitrile 
• 53957-33-8 2,5-dimethylbenzyl alcohol 
• 553-94-6 4-bromo-m-xylene 
• 143-33-9 sodium cyanide 
• 1122-42-5 2-iodo-p-xylene 
• 2039-89-6 2,5-dimethylstyrene 

Downstream Products

• 502930-49-6 2,5-dimethyl-α-phenylbenzenemethanimine 
• 610-72-0 2,5-dimethylbenzoic acid 
• 93-48-1 2,5-dimethylbenzylamine 
• 174534-15-7 1-amino-3,4-dihydro-3,7-dimethyl-2-naphthalenecarbonitrile 
• 30958-89-5 (CO)3Cr(NCC₆H₃(CH₃)2-2.5)3 
• 94365-02-3 pentachloro-(2,5-dimethylbenzonitrilo)-antimony 
• 872362-68-0 N'-hydroxy-2,5-dimethylbenzamidine 
• 1429642-50-1 C₁₇H₂₃NO 
• 5779-94-2 2,5-dimethylbenzaldehyde 
• 2142-73-6 1-(2,5-dimethylphenyl)-1-ethanone 
• 233604-29-0 (E)-3-[5-(2,5-Dimethylphenyl)-1,3,4-oxadiazol-2-yl]propenoic acid 

Relevant articles and documents

Nitrosation of Cyanamide: Preparation and Properties of the Elusive E- and Z-N'-Cyanodiazohydroxides

Nitrosation of cyanamide leads to unstable E/Z-cyanodiazohydroxides that easily deprotonate to E/Z-cyanodiazotates. Pursuing observations of E. Drechsel 145 years ago, the structure and reactivity of those products was determined, mainly in aqueous solution. Depending on the pH, three different thermal decomposition pathways give either N2O + HCN or N2 + HNCO. They were evaluated experimentally and by quantum mechanical calculations.

Transformation of aromatic bromides into aromatic nitriles with n-BuLi, pivalonitrile, and iodine under metal cyanide-free conditions

Various aromatic nitriles could be obtained in good yields by the treatment of aryl bromides with n-butyllithium and then pivalonitrile, followed by the treatment with molecular iodine at 70 °C, without metal cyanides under transition-metal-free conditions. The present reaction proceeds through the radical β-elimination of imino-nitrogen-centered radicals formed from the reactions of imines and N-iodoimines under warming conditions.

Sulfuryl Fluoride Mediated Conversion of Aldehydes to Nitriles

Aliphatic, aromatic, and heteroaromatic aldehydes were readily converted to corresponding nitriles in a one-pot reaction sequence with hydroxylamine and sulfuryl fluoride. The reaction proceeds at room temperature, does not require metal catalysts and special precautions, and produces nitriles in excellent yields. It is compatible with a variety of functional groups, can be performed in aqueous and organic solvents, and is readily scalable to multigram quantities. Mild conditions and high selectivity of the reaction enabled the construction of polyfunctional probes containing nitrile, alkyne, azide, and fluorosulfate groups for further orthogonal derivatization.