97165-77-0

Basic information

• Product Name: 3,5-DIBROMOBENZONITRILE
• Synonyms: 3,5-DIBROMOBENZONITRILE;3,5-Dibromobenzonitrile,97%;3,5-Dibromobenzonitrile 97%;Benzonitrile, 3,5-dibroMo-
• CAS NO: 97165-77-0
• Molecular Formula: C₇H₃Br₂N
• Molecular Weight: 260.91
• Product Categories: Aromatic Nitriles;Phenyls & Phenyl-Het;Nitrile;Bromine Compounds;Nitriles;Phenyls & Phenyl-Het
• Mol File: 97165-77-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 98 °C
• Boiling Point: 261.2 °C at 760 mmHg
• Flash Point: 111.8 °C
• Appearance: /
• Density: 2.06 g/cm³
• Vapor Pressure: 0.0117mmHg at 25°C
• Refractive Index: 1.662
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in Methanol
• CAS DataBase Reference: 3,5-DIBROMOBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIBROMOBENZONITRILE(97165-77-0)
• EPA Substance Registry System: 3,5-DIBROMOBENZONITRILE(97165-77-0)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39-36-23-22-4
• RIDADR: 3276
• HazardClass: IRRITANT
• Hazardous Substances Data: 97165-77-0(Hazardous Substances Data)

Usage

General Description

3,5-Dibromobenzonitrile is a chemical compound with the molecular formula C7H3Br2N. It is a white solid with a molecular weight of 248.91 g/mol. 3,5-Dibromobenzonitrile is widely used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. It is also used as a building block for the preparation of dyes, pigments, and other fine chemicals. 3,5-DIBROMOBENZONITRILE is highly toxic and may cause irritation to the skin, eyes, and respiratory system upon contact. It should be handled with proper care and stored in a well-ventilated area.

InChI:InChI=1/C7H3Br2N/c8-6-1-5(4-10)2-7(9)3-6/h1-3H

Upstream product

• 145691-59-4 (3,5-dibromophenyl)methanol 
• 56990-02-4 3,5-dibromobenzaldehyde 
• 1885-29-6 anthranilic acid nitrile 
• 68385-95-5 3,5-dibromoanthranilonitrile 
• 626-40-4 3,5-dibromoaniline 
• 58633-04-8 3,5-dibromo-4-aminobenzonitrile 
• 873-74-5 4-Aminobenzonitrile 
• 626-39-1 1,3,5-trisbromobenzene 
• 175205-85-3 3,5-dibromobenzamide 
• 618-58-6 3,5-dibromobenzoic acid 
• 23950-59-6 3,5-dibromobenzoyl chloride 

Downstream Products

• 1312924-00-7 3-(2-(5-methylpyridin-2-yl)ethynyl)-5-bromobenzonitrile 
• 1311261-28-5 3-(2'-amino-1',2,2-trimethyl-5'-oxo-1',5'-dihydrospiro[chroman-4,4'-imidazole]-6-yl)-5-bromobenzonitrile 
• 1595030-95-7 3-tributylstannyl-5-(2-pyridinylethynyl)benzonitrile 
• 1595030-96-8 3-tributylstannyl-5-((6-methylpyridin-2-yl)ethynyl)benzonitrile 
• 1312924-02-9 3-(2-(pyridin-2-yl)ethynyl)-5-iodobenzonitrile 
• 1312923-95-7 3-(2-(6-methylpyridin-2-yl)ethynyl)-5-iodobenzonitrile 
• 1595030-92-4 3-bromo-5-((6-methylpyridin-2-yl)ethynyl)benzonitrile 
• 1595030-89-9 3-bromo-5-(pyridine-2-ylethynyl)benzonitrile 
• 771580-86-0 (3,5-dibromophenyl)methanamine 

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.

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.

Potent mGluR5 antagonists: Pyridyl and thiazolyl-ethynyl-3,5-disubstituted- phenyl series

We report the synthesis of four series of 3,5-disubstituted-phenyl ligands targeting the metabotropic glutamate receptor subtype 5: (2-methylthiazol-4-yl) ethynyl (1a-j,), (6-methylpyridin-2-yl)ethynyl (2a-j), (5-methylpyridin-2-yl) ethynyl (3a-j,), and (pyridin-2-yl)ethynyl (4a-j,). The compounds were evaluated for antagonism of glutamate-mediated mobilization of internal calcium in an mGluR5 in vitro assay. All compounds were found to be full antagonists and exhibited low nanomolar to subnanomolar activity.