22445-42-7

Basic information

• Product Name: 3,5-Dimethylbenzonitrile
• Synonyms: 3,5-DIMETHYLBENZONITRILE;Benzonitrile, 3,5-dimethyl-;3,5-DIMETHYLBENZONITRILE 98%;3,5-dimethylbenzenecarbonitrile;3,5-dimethylphenyl carbonitrile;1,3-Dimethyl-5-cyanobenzene
• CAS NO: 22445-42-7
• Molecular Formula: C₉H₉N
• Molecular Weight: 131.17
• EINECS: 245-001-9
• Mol File: 22445-42-7.mol

Chemical Properties

• Melting Point: 42-43°C
• Boiling Point: 243.1 °C at 760 mmHg
• Flash Point: 100.8 °C
• Appearance: /
• Density: 0.99 g/cm³
• Vapor Pressure: 0.0327mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3,5-Dimethylbenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dimethylbenzonitrile(22445-42-7)
• EPA Substance Registry System: 3,5-Dimethylbenzonitrile(22445-42-7)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22
• Safety Statements: 26-36/37/39
• RIDADR: 3276
• HazardClass: IRRITANT-HARMFUL
• Hazardous Substances Data: 22445-42-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Dimethylbenzonitrile is used as a precursor for the synthesis of various pharmaceuticals, contributing to the development of new medications and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 3,5-Dimethylbenzonitrile is utilized as a starting material for the production of agrochemicals, which are essential for enhancing crop protection and yield.
Used in Specialty Chemicals Production:
3,5-Dimethylbenzonitrile serves as a building block in the synthesis of specialty chemicals, which are used in a wide range of applications due to their unique properties.
Used in Dyes and Pigments Industry:
3,5-Dimethylbenzonitrile is used as an intermediate in the production of dyes and pigments, which are crucial for coloring various materials in industries such as textiles, plastics, and printing inks.
Used in Plastics Industry:
3,5-Dimethylbenzonitrile is employed in the manufacturing process of plastics, where it helps in creating specific properties required for different applications.
Used in Perfume and Flavoring Industry:
As a component in the synthesis of organic compounds, 3,5-Dimethylbenzonitrile is used in the perfume and flavoring industry to create distinctive scents and tastes.
It is important to handle 3,5-dimethylbenzonitrile with care due to its potential health hazards and environmental risks, as it is considered harmful if swallowed, inhaled, or in contact with skin. Proper safety measures should be taken during its use to mitigate any risks associated with this chemical compound.

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

Upstream product

• 5692-35-3 3,5-dimethylbenzamide 
• 108-69-0 3,5-dimethylaminoaniline 
• 499-06-9 3,5-dimethylbenzoic acid 
• 151-50-8 potassium cyanide 
• 675-09-2 4,6-Dimethyl-2-pyron 
• 920-37-6 2-Chloroacrylonitrile 
• 108-67-8 1,3,5-trimethyl-benzene 
• 22445-41-6 3,5-dimethylphenyl iodide 
• 556-96-7 5-bromo-1,3-xylene 
• 143-33-9 sodium cyanide 
• 557-21-1 dicyanozinc 
• 108-68-9 3,5-Dimethylphenol 
• 120-72-9 indole 
• 110-70-3 N,N`-dimethylethylenediamine 

Downstream Products

• 5379-16-8 3,5-dimethylacetophenone 
• 188984-18-1 3-chloromethyl-5-methyl-benzonitrile 
• 124289-23-2 3-(bromomethyl)-5-methylbenzonitrile 
• 74163-48-7 3,5-bis(bromomethyl)benzonitrile 
• 25843-55-4 3,5-Bis(trichloromethyl)benzonitrile 
• 39718-07-5 5-methylbenzene-1,3-dicarbonitrile 
• 10365-94-3 1,3,5-tricyanobenzene 
• 172369-18-5 N,3,5-trimethylbenzamide 
• 3858-80-8 3,5-dimethylbenzylamine hydrochloride 
• 107146-56-5 1,2-bis(3,5-dimethylphenyl)acetylene 
• 348621-27-2 3,5-bis(dimethyl phosphonatemethyl)benzonitrile 
• 348621-30-7 3,5-bis[2'-4(dibuthylaminophenyl)vinyl]benzaldehyde 
• 348621-28-3 3,5-bis[2'-4(dibutylaminophenyl)vinyl]benzonitrile 
• 348621-32-9 3,5-bis{2'[3,5-bis[2'-(4-dibutylaminophenyl)vinyl]]}benzonitrile 

Relevant articles and documents

Method for converting aromatic aldehyde into aromatic nitrile by using sulfur powder promoted inorganic ammonium as nitrogen source (by machine translation)

The invention discloses a method for converting aromatic aldehyde into aromatic nitrile. The method is conversion of high yield of aromatic aldehyde one-pot reaction of sulfur powder promoted inorganic ammonium as a nitrogen source into aromatic nitrile. The method has the advantages of no need of metal participation, no need of strong oxide, compatibility of reaction to air, easiness in amplification to a gram scale and the like, and overcomes the problems of harsh reaction conditions, complex operation, low functional group compatibility and the like in the prior art. (by machine translation)

Zn-catalyzed cyanation of aryl iodides

We report the first example of zinc-catalyzed cyanation of aryl iodides with formamide as the cyanogen source. The transformation was promoted by the bisphosphine Nixantphos ligand. Under optimized conditions, a variety of electron-donating and electron-withdrawing aryl iodides were converted into nitrile products in good to excellent yields. This approach is an exceedingly simple and benign method for the synthesis of aryl nitriles and is likely to proceed via a dinuclear Zn-concerted catalysis.

Dual Ligand-Enabled Nondirected C-H Cyanation of Arenes

Aromatic nitriles are key structural units in organic chemistry and, therefore, highly attractive targets for C-H activation. Herein, the development of an arene-limited, nondirected C-H cyanation based on the use of two cooperatively acting commercially available ligands is reported. The reaction enables the cyanation of arenes by C-H activation in the absence of directing groups and is therefore complementary to established approaches.

Ligand-Promoted Non-Directed C?H Cyanation of Arenes

This article reports the first example of a 2-pyridone accelerated non-directed C?H cyanation with an arene as the limiting reagent. This protocol is compatible with a broad scope of arenes, including advanced intermediates, drug molecules, and natural products. A kinetic isotope experiment (kH/kD=4.40) indicates that the C?H bond cleavage is the rate-limiting step. Also, the reaction is readily scalable, further showcasing the synthetic utility of this method.

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.

Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile: Via C-CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine

We developed a non-toxic cyanation reaction of various aryl halides and triflates in acetonitrile using a catalyst system of [Ni(MeCN)6](BF4)2, 1,10-phenanthroline, and 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine (Si-Me4-DHP). Si-Me4-DHP was found to function as a reductant for generating nickel(0) species and a silylation reagent to achieve the catalytic cyanation via C-CN bond cleavage.

Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides to Form Nitriles

A palladium(II) catalyst, in the presence of Selectfluor, enables the efficient and chemoselective transformation of primary amides into nitriles. The amides can be attached to aromatic rings, heteroaromatic rings, or aliphatic side chains, and the reactions tolerate steric bulk and electronic modification. Dehydration of a peptaibol containing three glutamine groups afforded structure-activity relationships for each glutamine residue. Thus, this dehydration can act similarly to an alanine scan for glutamines via synthetic mutation.

Stable palladium nanoparticles catalyzed synthesis of benzonitriles using K4[Fe(CN)6]

A stable palladium nanocatalyst is used in the synthesis of benzonitriles by cyanation of aryl iodides. A nontoxic and economic potassium hexacyanoferrate was used as a safe cyanide source. A variety of benzonitriles are efficiently synthesized using the stable nanocatalyst. The catalyst was quantitatively recovered and reused without any apparent loss in the catalytic activity.

Cobalt-Catalyzed Electrophilic Cyanation of Arylzinc Halides with N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS)

The cobalt-catalyzed cross-coupling of organozinc bromides with N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) is described. The same cobalt catalyst, cobalt(II) bromide, was used for both the synthesis of the organozinc species and the cross-coupling reaction. However in this case, a catalytic amount of zinc dust is necessary in the second step to release the low-valent cobalt. Under these mild conditions, moderate to excellent yields of different benzonitriles were obtained.

Iodine-catalyzed ammoxidation of methyl arenes

The development of organic transformation using cheap and readily available substrates under mild conditions will be pivotal for green and sustainable synthetic organic chemistry. Concerning our continued interest in the cyanation reaction, a metal-free direct ammoxidation of readily available methyl arenes leading to nitriles was established under mild conditions. A series of aryl methanes especially heteroaryl methanes (30 examples) were applicable in moderate to good yields with good functionality tolerance.