5955-73-7

Basic information

• Product Name: 2-METHYLBENZOYL CYANIDE
• Synonyms: 2-METHYLBENZOYL CYANIDE;OXO-O-TOLYL-ACETONITRILE;2-methyl phenyl glyoxylonitrile;Benzeneacetonitrile, 2-Methyl-a-oxo-
• CAS NO: 5955-73-7
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• EINECS: 200-258-5
• Mol File: 5955-73-7.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 239.226 °C at 760 mmHg
• Flash Point: 98.481 °C
• Appearance: /
• Density: 1.111 g/cm³
• Vapor Pressure: 0.041mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-METHYLBENZOYL CYANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLBENZOYL CYANIDE(5955-73-7)
• EPA Substance Registry System: 2-METHYLBENZOYL CYANIDE(5955-73-7)

Safety Data

• Hazardous Substances Data: 5955-73-7(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1/C9H7NO/c1-7-4-2-3-5-8(7)9(11)6-10/h2-5H,1H3

Upstream product

• 592-04-1 mercury(II) cyanide 
• 933-88-0 ortho-toluoyl chloride 
• 544-92-3 copper(I) cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 151-50-8 potassium cyanide 
• 118-90-1 ortho-methylbenzoic acid 
• 773837-37-9 sodium cyanide 
• 22364-68-7 2-tolylmethylnitrile 
• 84452-03-9 Dichloro-o-tolyl-acetonitrile 
• 85589-34-0 2-hydroxy-2-(2-methylphenyl)acetonitrile 
• 74-90-8 hydrogen cyanide 
• 143-33-9 sodium cyanide 
• 1052175-57-1 C₉H₈BrN 
• 529-20-4 2-methylphenyl aldehyde 

Downstream Products

• 89-71-4 2-Methyl-benzoic acid methyl ester 
• 34966-54-6 methyl 2-oxo-2-(o-tolyl)acetate 
• 61001-54-5 2-methyldibenzoylmethane 
• 133409-72-0 methyl (E)-2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate 
• 120974-97-2 methyl-(E)-2-(2-tolyl)-2-methoxyiminoacetate 
• 144106-03-6 (Z)-2-(2-tolyl)-2-methoxyiminoacetic acid methyl ester 
• 118-90-1 ortho-methylbenzoic acid 

Relevant articles and documents

Preparation method of O-methylbenzoyl nitrile

The method comprises the following steps: firstly dissolving o-methylbenzoic acid in a toluene solvent, dropping the dimethyl sulfoxide to carry out reaction, and removing a small amount of unreacted dichlorosulphoxide at low temperature after the reactio

Novel synthesis method of alpha-carbonyl acid ester

The invention discloses a novel synthesis method of alpha-carbonyl acid ester. The method comprises the following steps: carrying out chlorination reaction on an alpha-methylene-containing nitrile compound and chlorine to obtain dichloronitrile, reacting the dichloronitrile product in a sulfuric acid and water system to obtain formyl cyanide, then acquiring an imino sulfate compound in the same reaction system, and finally performing esterification to obtain the target product. The adopted reaction raw materials are wide in sources and low in price, highly toxic solid sodium cyanide can be prevented from being used in the prior art, the method is environmentally friendly, and the method is easy to operate, mild in condition and easy to industrialize.

Acceptorless and Base-free Dehydrogenation of Cyanohydrin with (η6-Arene)halide(Bidentate Phosphine)ruthenium(II) Complex

Ruthenium-catalyzed dehydrogenation of cyanohydrins under acceptorless and base-free conditions was demonstrated for the first time in the synthesis of acyl cyanide. As opposed to the thermodynamically preferred elimination of hydrogen cyanide, the dehydrogenation of cyanohydrins could be kinetically controlled with ruthenium (II) bidentate phosphine complexes. The effects of the arene, phosphine ligands and counter anions were investigated in regard to catalytic activity and selectivity. Selective dehydrogenation can occur via β-hydride elimination with the experimentally observed [(alkoxide)Ru] complex. (Figure presented.).

A stretching of the intermediate O-methyl benzoyl nitrile synthetic method

The invention relates to a method for preparing a key intermediate methylbenzoyl cyanide in the process of synthesizing trifloxystrobin. The method comprises the following steps: adding o-toluoyl chloride, a solvent and a catalyst into a reaction kettle; introducing metered hydrocyanic acid gas, completely reacting under a heat insulating conditon to obtain methylbenzoyl cyanide, and carrying out back-distillation to obtain a methylbenzoyl cyanide product. The content of methylbenzoyl cyanide is over 99 percent and the yield can be over 95 percent metered in form of o-toluoyl chloride. The method is simple and convenient to operate, the utilization of the raw material o-toluoyl chloride is high; except the byproduct hydrochloric acid, almost no other wastes are generated, and atomic economic reaction is basically realized. The method is a synthesizing process with good economic prospect.

Rh-Catalyzed Asymmetric Hydrogenation of 1,2-Dicyanoalkenes

A highly efficient enantioselective hydrogenation of 1,2-dicyanoalkenes catalyzed by the complex of rhodium and f-spiroPhos has been developed. A series of 1,2-dicyanoalkenes were successfully hydrogenated to the corresponding chiral 1,2-dicyanoalkanes under mild conditions with excellent enantioselectivities (up to 98% ee). This methodology provides efficient access to the asymmetric synthesis of chiral diamines.

Synthesis and biological evaluation of kresoxim-methyl analogues as novel inhibitors of hypoxia-inducible factor (HIF)-1 accumulation in cancer cells

We designed and synthesized strobilurin analogues as hypoxia-inducible factor (HIF) inhibitors based on the molecular structure of kresoxim-methyl. Biological evaluation in human colorectal cancer HCT116 cells showed that most of the synthesized kresoxim-methyl analogues possessed moderate to potent inhibitory activity against hypoxia-induced HIF-1 transcriptional activation. Three candidates, compounds 11b, 11c, and 11d were identified as potent inhibitors against HIF-1 activation with IC50 values of 0.60–0.94?μM. Under hypoxic condition, compounds 11b, 11c, and 11d increased the intracellular oxygen contents, thereby attenuating the hypoxia-induced accumulation of HIF-1α protein.

AN IMPROVED PROCESS FOR THE SYNTHESIS OF STROBILURIN FUNGICIDES VIZ TRIFLOXYSTROBIN AND KRESOXIM-METHYL

The present invention relates to an improved process for the synthesis of E-isomer of compound of formula (5). It further relates to the conversion of formula (5), wherein R is H, to Intermediate (I) and subsequently to substantially pure Trifloxystrobin, compound of formula (I) in good yield.

METHOXYIMINO COMPOUNDS AND FUNGICIDE COMPOSITION COMPRISING SAME

The present invention provides a methoxyimino compound, and a fungicide composition comprising same as an active ingredient. The methoxyimino compound of the present invention, which has an excellent antifungal activity against a wide spectrum of fungi even at a low application rate, can be used to protect various crops.

A new convenient synthesis of aroyl cyanides via the formation of cyanohydrin nitrate intermediates

The treatment of α-bromoarylacetonitriles with AgNO3 generates cyanohydrin nitrate intermediates, which easily eliminate nitrous acid with the formation of carbonyl bond to afford aroyl cyanides in good to high yields.

AgI-PEG400-KI catalyzed environmentally benign synthesis of aroyl cyanides using potassium hexacyanoferrate(II) as the cyanating agent

A practical cyanation of aroyl chlorides with 0.2 equivalent of non-toxic cyanide source, K4[Fe(CN)6], 3 mol% AgI, 4 mol% PEG-400, and 3 mol% KI as the catalyst system is described. The reactions were performed in DMF at room temperature and provided the corresponding aroyl cyanides in 64-89% yield, typically in less than ten hours. Georg Thieme Verlag Stuttgart.