3,5-Dibromobenzonitrile

Base Information

• Chemical Name: 3,5-Dibromobenzonitrile
• CAS No.: 97165-77-0
• Molecular Formula: C7H3Br2N
• Molecular Weight: 260.916
• Hs Code.: 29269090
• European Community (EC) Number: 806-988-7
• DSSTox Substance ID: DTXSID80383944
• Nikkaji Number: J3.002.927E
• Wikidata: Q72463880
• Mol file: 97165-77-0.mol

Synonyms:3,5-dibromobenzonitrile;97165-77-0;Benzonitrile, 3,5-dibromo-;MFCD00178770;Maybridge1_007794;3,5-dibromo-benzonitrile;SCHEMBL200313;HMS563K06;DTXSID80383944;QUJGDNCWTBTBQD-UHFFFAOYSA-N;TD1139;AKOS005259306;CS-W021811;PS-7363;AC-28542;SY032188;AM20050019;D5049;FT-0614511;EN300-221297;Z1269138219

Chemical Property of 3,5-Dibromobenzonitrile

Chemical Property:

• Vapor Pressure: 0.0117mmHg at 25°C
• Melting Point: 98 °C
• Refractive Index: 1.662
• Boiling Point: 261.2 °C at 760 mmHg
• Flash Point: 111.8 °C
• PSA: 23.79000
• Density: 2.06 g/cm³
• LogP: 3.08328
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 260.86117
• Heavy Atom Count: 10
• Complexity: 150

Purity/Quality:

99% ^*data from raw suppliers

3,5-Dibromobenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39-36-23-22-4

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C=C1Br)Br)C#N

Technology Process of 3,5-Dibromobenzonitrile

There total 14 articles about 3,5-Dibromobenzonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

3,5-dibromobenzaldehyde (56990-02-4) → 3,5-dibromobenzonitrile (97165-77-0)

Guidance literature:

3,5-dibromobenzaldehyde; With hydroxylamine hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 0.0833333h;

With potassium hydrogen difluoride; 3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate; In water; at 20 ℃; for 3h;

DOI:10.1002/chem.201805175

Reference yield: 77.3%

(3,5-dibromophenyl)methanol (145691-59-4) → 3,5-dibromobenzamide (175205-85-3) + 3,5-dibromobenzonitrile (97165-77-0)

Guidance literature:

With ammonia; oxygen; In tert-Amyl alcohol; water; at 100 ℃; for 5.5h; under 3750.38 Torr; Overall yield = > 99 percent; Autoclave; High pressure;

DOI:10.1021/acscatal.0c00485

Reference yield: 75.0%

1,3,5-trisbromobenzene (626-39-1) → 3,5-dibromobenzonitrile (97165-77-0)

Guidance literature:

1,3,5-trisbromobenzene; With isopropylmagnesium chloride; lithium chloride; In tetrahydrofuran; at -15 ℃; for 0.25h;

With N,N-dimethyl-formamide; In tetrahydrofuran; at 0 ℃; for 2h;

With ammonia; iodine; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2012.12.022

upstream raw materials:

3,5-dibromoaniline

3,5-dibromoanthranilonitrile

anthranilic acid nitrile

3,5-dibromobenzoyl chloride

Downstream raw materials:

3-(2-(2-methylthiazol-4-yl)ethynyl)-5-bromobenzonitrile

3-(2-(5-methylpyridin-2-yl)ethynyl)-5-bromobenzonitrile

Refernces

• 1、 Gates, Bruce C.,Guan, Erjia,Meng, Xiangju,Wang, Chengtao,Wang, Hai,Wang, Liang,Wang, Sai,Xiao, Feng-Shou,Xu, Dongyang,Xu, Hua,Yang, Bo,Zhang, Jian. "Atomically Dispersed Ru on Manganese Oxide Catalyst Boosts Oxidative Cyanation". . p. 6299 - 6308. Retrieved 2020/07/21.
• 2、 Ishii, Genki,Harigae, Ryo,Moriyama, Katsuhiko,Togo, Hideo. "Practical one-pot conversion of aryl bromides and β-bromostyrenes into aromatic nitriles and cinnamonitriles". . p. 1462 - 1469. Retrieved 2013/02/25.