4-Amino-3-bromobenzonitrile

Base Information

• Chemical Name: 4-Amino-3-bromobenzonitrile
• CAS No.: 50397-74-5
• Molecular Formula: C7H5BrN2
• Molecular Weight: 197.034
• Hs Code.: 29269090
• European Community (EC) Number: 626-815-7
• DSSTox Substance ID: DTXSID10363931
• Nikkaji Number: J1.281.657J
• Wikidata: Q72438414
• Mol file: 50397-74-5.mol

Synonyms:4-Amino-3-bromobenzonitrile;50397-74-5;3-Bromo-4-aminobenzonitrile;2-Bromo-4-cyanoaniline;benzonitrile, 4-amino-3-bromo-;4-Amino-3-bromo-benzonitrile;4-amino-3-brombenzonitrile;MFCD01861386;4-amino-3-bromobenzonitile;4-amino-3-bromobenzo-nitrile;SCHEMBL616196;DTXSID10363931;4-Amino-3-bromobenzonitrile, 97%;AKOS001466128;AC-1795;AM61569;CS-W002840;PS-5927;4-azanyl-3-bromanyl-benzenecarbonitrile;NCGC00341249-01;SY018639;A1723;FT-0639896;EN300-30639;AB01153928-03;A828100;J-640248;J-800247;Z315898992

Chemical Property of 4-Amino-3-bromobenzonitrile

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00113mmHg at 25°C
• Melting Point: 106-110 °C(lit.)
• Refractive Index: 1.652
• Boiling Point: 300.3 °C at 760 mmHg
• PKA: -0.34±0.10(Predicted)
• Flash Point: 135.4 °C
• PSA: 49.81000
• Density: 1.68 g/cm³
• LogP: 2.48418
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: soluble in Methanol
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 195.96361
• Heavy Atom Count: 10
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

4-Amino-3-bromobenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-43-36/37/38-20/21/22
• Safety Statements: 36/37-36/37/39-26-22

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C#N)Br)N

Technology Process of 4-Amino-3-bromobenzonitrile

There total 5 articles about 4-Amino-3-bromobenzonitrile 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: 97.0%

4-Aminobenzonitrile (873-74-5) → 2-bromo-4-cyanoaniline (50397-74-5)

Guidance literature:

With phosphotungstic acid; N-bromosaccharin; In acetonitrile; at 0 ℃; for 0.0166667h; regioselective reaction;

DOI:10.1080/00397910903395268

Reference yield: 78.0%

→ 2-bromo-4-cyanoaniline (50397-74-5)

Guidance literature:

With hydrogen bromide; 2-methylpyridinium nitrate; at 90 ℃; for 8h; Green chemistry;

Reference yield: 69.0%

3-bromo-4-(trifluoroacetylamino)benzonitrile (143321-91-9) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → 2-bromo-4-cyanoaniline (50397-74-5) + (E)-3-(2-Bromo-4-cyano-phenylamino)-4,4,4-trifluoro-but-2-enoic acid ethyl ester

Guidance literature:

In toluene; Heating;

upstream raw materials:

4-Aminobenzonitrile

3-bromo-4-(trifluoroacetylamino)benzonitrile

ethyl (triphenylphosphoranylidene)acetate

4-nitrobenzonitrile

Downstream raw materials:

N-(2-bromo-4-cyanophenyl)-1H-pyrrole-2-carboxamide

6-amino-4'-fluoro-[1,1'-biphenyl]-3-carbonitrile

4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(1H-tetrazol-5-yl)-phenyl]-amide

Refernces

• 1、 Henry, Martyn C.,McGrory, Rochelle,Faggyas, Réka J.,Mostafa, Mohamed A. B.,Sutherland, Andrew. "One-pot ortho-amination of aryl C-H bonds using consecutive iron and copper catalysis". . p. 4629 - 4639. Retrieved 2019/05/17.
• 2、 Panyam, Pradeep Kumar Reddy,Gandhi, Thirumanavelan. "Palladium(II)/N-Heterocyclic Carbene-Catalyzed Regioselective Heteroannulation of Tertiary Propargyl Alcohols and o-Haloanilines to form 2-Alkenylindoles". supporting information. p. 1144 - 1151. Retrieved 2017/04/13.