22884-95-3

Basic information

• Product Name: 3,4-Dimethylbenzonitrile
• Synonyms: 1,2-Dimethyl-4-cyanobenzene;3,4-dimethyl-benzonitril;Benzonitrile, 3,4-dimethyl-;4-CYANO-O-XYLENE;3,4-DIMETHYLBENZONITRILE;Xylylic acid nitrile;3,4-Dimethylbenzoic acid nitrile;3,4-Dimethylbenzonit
• CAS NO: 22884-95-3
• Molecular Formula: C₉H₉N
• Molecular Weight: 131.17
• EINECS: 245-293-8
• Product Categories: Aromatic Nitriles;Benzenes
• Mol File: 22884-95-3.mol

Chemical Properties

• Melting Point: 67 °C
• Boiling Point: 253.472 °C at 760 mmHg
• Flash Point: 107.137 °C
• Appearance: /
• Density: 0.992 g/cm³
• Vapor Pressure: 0.0182mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 970523
• CAS DataBase Reference: 3,4-Dimethylbenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dimethylbenzonitrile(22884-95-3)
• EPA Substance Registry System: 3,4-Dimethylbenzonitrile(22884-95-3)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36/37/39-36/37
• RIDADR: 3276
• RTECS: DI4357500
• HazardClass: IRRITANT-HARMFUL
• PackingGroup: III
• Hazardous Substances Data: 22884-95-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 28, p. 3025, 1972 DOI: 10.1016/0040-4020(72)80017-6

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

Upstream product

• 506-68-3 bromocyane 
• 95-47-6 o-xylene 
• 3862-11-1 phosphoric acid tris-(3,4-dimethyl-phenyl ester) 
• 151-50-8 potassium cyanide 
• 544-92-3 copper(I) cyanide 
• 95-64-7 4-amino-o-xylene 
• 143814-17-9 2,6-dicyanatoanthraquinone 
• 619-04-5 3,4-dimethylbenzoic acid 
• 583-71-1 4-bromo-o-xylene 
• 68-12-2 N,N-dimethyl-formamide 
• 557-21-1 zinc(II) cyanide 
• 55499-43-9 3,4-dimethyl phenylboronic acid 
• 31599-61-8 3,4-dimethyliodobenzene 
• 6966-10-5 3,4-dimethylbenzyl alcohol 

Downstream Products

• 5973-71-7 3,4-dimethylbenzaldehyde 
• 40312-15-0 3,4-dimethyl-benzamide oxime 
• 55308-45-7 ethyl 3,4-dimethylbenzimidate 
• 3637-01-2 3,4-dimethylacetophenone 
• 845-04-5 3'-Trifluormethyl-3,4-dimethyl-benzophenon 
• 5747-87-5 5-benzyl-6-chloro-2-(3,4-dimethyl-phenyl)-[1,3]oxazin-4-one 
• 102-48-7 3,4-Dimethylbenzylamin 
• 15089-77-7 2,3-dimethyl-6-nitrobenzonitrile 
• 52911-61-2 3,4-dimethyl-5-nitrobenzonitrile 
• 52911-62-3 3,4-dimethyl-2-nitrobenzonitrile 
• 19047-19-9 4-cyano-α,α,α',α'-tetrabromo-o-xylene 
• 58952-03-7 3,4-dimethyl-thiobenzamide 
• 147219-20-3 3-(3,4-Dimethylphenyl)-propensaeure 
• 3400-36-0 N,3,4-trimethylbenzamide 

Relevant articles and documents

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Pincer metal complexes exhibit superior catalytic activity in the dehydrogenation of plain alkanes, but find limited application in the dehydrogenation of functionalized organic molecules. Starting from easily accessible primary alkyl azides, here we report an efficient dehydrogenation of azides to nitriles using pincer iridium or ruthenium complexes as the catalysts. This method offers a route to cyanide-free preparation of nitriles without carbon chain elongation and without the use of strong oxidants. Both benzyl and linear aliphatic azides can be dehydrogenated with tert-butylethylene as the hydrogen acceptor to afford nitriles in moderate to high yields. Various functional groups can be tolerated, and the H?C?C?H bond dehydrogenation does not occur for linear alkyl azide substrates. Furthermore, the pincer Ir catalytic system was found to catalyze the direct azide dehydrogenation without the use of a sacrificial hydrogen acceptor.

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Cyano-containing compounds constitute important pharmaceuticals, agrochemicals and organic materials. Traditional cyanation methods often rely on the use of toxic metal cyanides which have serious disposal, storage and transportation issues. Therefore, there is an increasing need to develop general and efficient catalytic methods for cyanide-free production of nitriles. Here we report the reductive cyanation of organic chlorides using CO2/NH3 as the electrophilic CN source. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs.

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