5-Bromo-2-iodobenzonitrile

Base Information

• Chemical Name: 5-Bromo-2-iodobenzonitrile
• CAS No.: 121554-10-7
• Molecular Formula: C7H3BrIN
• Molecular Weight: 307.916
• Hs Code.: 29269090
• DSSTox Substance ID: DTXSID30427307
• Nikkaji Number: J2.211.063B
• Wikidata: Q72457494
• Mol file: 121554-10-7.mol

Synonyms:5-Bromo-2-iodobenzonitrile;121554-10-7;Benzonitrile, 5-bromo-2-iodo-;MFCD00672950;2-IODO-5-BROMOBENZONITRILE;5-Bromo-2-iodo-benzonitrile;SCHEMBL142523;DTXSID30427307;JIGKPMMZNMQXDL-UHFFFAOYSA-N;AKOS015834756;AM61304;CS-W008515;DS-1630;AC-26113;SY016992;B2215;FT-0620097;A21024

Chemical Property of 5-Bromo-2-iodobenzonitrile

Chemical Property:

• Vapor Pressure: 0.000601mmHg at 25°C
• Melting Point: 120-122°C
• Refractive Index: 1.71
• Boiling Point: 310.4 °C at 760 mmHg
• Flash Point: 141.5 °C
• PSA: 23.79000
• Density: 2.31 g/cm³
• LogP: 2.92538
• Storage Temp.: Room temperature.
• Sensitive.: Light Sensitive
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 306.84936
• Heavy Atom Count: 10
• Complexity: 162

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Bromo-2-iodobenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22-36/37/38:
• Hazard Codes: R20/21/22-36/37/38:
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 5-Bromo-2-iodobenzonitrile

There total 3 articles about 5-Bromo-2-iodobenzonitrile 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: 86.0%

2-amino-5-bromobenzonitrile (39263-32-6) → 5-bromo-2-iodobenzonitrile (121554-10-7)

Guidance literature:

With tert.-butylnitrite; iodine; In acetonitrile; at 23 ℃; for 1h;

DOI:10.1021/jo026784b

Reference yield: 73.0%

3-cyanobromobenzene (6952-59-6) → 5-bromo-2-iodobenzonitrile (121554-10-7)

Guidance literature:

With N-iodo-succinimide; palladium diacetate; toluene-4-sulfonic acid; In 1,2-dichloro-ethane; at 70 ℃; for 12h; Sealed tube;

DOI:10.1021/jo302765g

Reference yield:

anthranilic acid nitrile (1885-29-6) → 5-bromo-2-iodobenzonitrile (121554-10-7)

Guidance literature:

Multi-step reaction with 2 steps

1: KBr; NaBO₃*4H₂O; (NH₄)6Mo₇O₂₄*4H₂O / acetic acid / 3 h / 20 °C

2: I₂; t-butyl nitrite / acetonitrile / 3 h / Heating

With sodium perborate; ammonium heptamolybdate; tert.-butylnitrite; iodine; potassium bromide; In acetic acid; acetonitrile;

DOI:10.1021/ol0528991

upstream raw materials:

2-amino-5-bromobenzonitrile

anthranilic acid nitrile

3-cyanobromobenzene

Downstream raw materials:

5-bromo-2-([4-(methylthio)phenyl]ethynyl)benzonitrile

5-bromo-2-([4-cyanophenyl]ethynyl)benzonitrile

5-bromo-2-trimethylsilanylethynyl-benzonitrile

5-bromo-2-p-tolylethynyl-benzonitrile

Refernces

• 1、 Yang, Xin,Kajiyama, Shingo,Fang, Jing-Kun,Xu, Feng,Uemura, Yu,Koumura, Nagatoshi,Hara, Kohjiro,Orita, Akihiro,Otera, Junzo. "Synthesis and properties of anthrylene-substituted phenyleneethynylene dyes having amino/cyano group(s) and their application to dye-sensitized solar cells". supporting information; experimental part. p. 687 - 697. Retrieved 2012/07/30.
• 2、 Ochi, Takanori,Yamaguchi, Yoshihiro,Wakamiya, Tateaki,Matsubara, Yoshio,Yoshida, Zen-Ichi. "Block modification of rod-shaped π conjugated carbon frameworks with donor and acceptor groups toward highly fluorescent molecules: Synthesis and emission characteristics". supporting information; scheme or table. p. 1222 - 1231. Retrieved 2008/10/09.