6587-24-2

Basic information

• Product Name: METHYL 2-CYANOBENZOATE
• Synonyms: METHYL 2-CYANOBENZOATE;2-CYANO-BENZOIC ACID METHYL ESTER;2-(Methoxycarbonyl)benzonitrile
• CAS NO: 6587-24-2
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• Product Categories: Aromatic Esters;Esters;Phenyls & Phenyl-Het
• Mol File: 6587-24-2.mol
• Article Data: 31

Chemical Properties

• Melting Point: 49 °C
• Boiling Point: 98-100°C 0,2mm
• Flash Point: 136.2oC
• Appearance: /
• Density: 1.18g/cm3
• Vapor Pressure: 0.00149mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: METHYL 2-CYANOBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-CYANOBENZOATE(6587-24-2)
• EPA Substance Registry System: METHYL 2-CYANOBENZOATE(6587-24-2)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22
• Safety Statements: 26-36/37/39
• RIDADR: 3439
• HazardClass: IRRITANT, IRRITANT-HARMFUL
• Hazardous Substances Data: 6587-24-2(Hazardous Substances Data)

Usage

Description

METHYL 2-CYANOBENZOATE, also known as methyl o-cyanobenzoate, is a benzoic acid derivative with the molecular formula C9H7NO2. It is a colorless to pale yellow liquid characterized by a floral odor. This chemical is primarily recognized for its use as a flavoring agent in the food industry, while also serving as an intermediate in the synthesis of pharmaceuticals and agrochemicals. Due to its potential skin and eye irritation, it is crucial to handle METHYL 2-CYANOBENZOATE with care, adhering to safety protocols such as wearing personal protective equipment and maintaining proper ventilation.

Uses

Used in the Food Industry:
METHYL 2-CYANOBENZOATE is used as a flavoring agent for its distinctive floral scent, enhancing the taste and aroma of various food products.
Used in Pharmaceutical Production:
METHYL 2-CYANOBENZOATE is used as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new medications.
Used in Agrochemical Production:
METHYL 2-CYANOBENZOATE is utilized as an intermediate in the production of agrochemicals, playing a role in the creation of substances that contribute to agricultural productivity and pest control.
Safety Precautions:
When handling METHYL 2-CYANOBENZOATE, it is used with caution due to its skin and eye irritant properties. Proper safety protocols are followed, including the use of personal protective equipment and ensuring well-ventilated workspaces to minimize exposure risks.

InChI:InChI=1/C9H7NO2/c1-12-9(11)8-5-3-2-4-7(8)6-10/h2-5H,1H3

Upstream product

• 134-20-3 2-carbomethoxyaniline 
• 57031-51-3 Methyl-tert.-butylperoxyoxalat 
• 100-47-0 benzonitrile 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 151-50-8 potassium cyanide 
• 544-92-3 copper(I) cyanide 
• 88-97-1 phthalamic acid 
• 79-22-1 methyl chloroformate 
• 67-56-1 methanol 
• 95667-98-4 methyl 2-((methylsulfonyl)oxy)benzoate 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 610-96-8 methyl chlorobenzoate 
• 557-21-1 dicyanozinc 
• 74-88-4 methyl iodide 

Downstream Products

• 55-21-0 benzamide 
• 1159-86-0 o-dibenzoylbenzene 
• 480-91-1 oxisoindole 
• 4122-56-9 methyl o-formylbenzoate 
• 76010-55-4 methyl 2-(3-phenyl-1,2,4-thiadiazol-5-yl)benzoate 
• 100-47-0 benzonitrile 
• 1310689-78-1 9-methylisoindolo[1,2-b]quinazolin-12(10H)-one 
• 67199-66-0 batracylin 

Relevant articles and documents

Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp3)?H Bonds**

The metal-free activation of C(sp3)?H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the commercially available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodology, a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the scope of the method with over 50 examples including late-stage functionalization of drug molecules (celecoxib) and complex structures such as l-menthol, amino acids, and cholesterol derivatives. Furthermore, the presented synthetic protocol is applicable for gram-scale reactions. In addition to methylarenes, selected examples for the cyanation of aldehydes, alcohols and oximes are demonstrated as well. Detailed mechanistic investigations have been carried out using time-resolved luminescence quenching studies, control experiments, and NMR spectroscopy as well as kinetic studies, all supporting the proposed catalytic cycle.

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.

Methyl esters of 2-(N-hydroxycarbamimidoyl)benzoyl-substituted α-amino acids as promising building blocks in peptidomimetic synthesis: a comparative study

Abstract: An efficient and simple synthetic protocol for the synthesis of a number methyl esters of 2-(N-hydroxycarbamimidoyl)benzoyl-substituted (S)-α-amino acids via subsequent coupling and hydroxyamination of 2-cyanobenzamide derivatives has been developed. Comparative analysis of three pseudopeptide series based on 2-cyano- and 2-amidoxime-substituted benzoic acid and its pyridine and pyrazine counterparts has been provided and it has revealed a practical advantage of the benzoic acid derivatives due to their greater availability. The impact of the nitrogen atom in the aromatic ring on the trans/cis-amide equilibrium in the proline derivatives is discussed. Graphical abstract: [Figure not available: see fulltext.]