4-Bromo-2-nitrobenzoic acid

Base Information

• Chemical Name: 4-Bromo-2-nitrobenzoic acid
• CAS No.: 99277-71-1
• Molecular Formula: C7H4BrNO4
• Molecular Weight: 246.017
• Hs Code.: 29163990
• European Community (EC) Number: 627-797-3
• DSSTox Substance ID: DTXSID20396250
• Nikkaji Number: J1.988.562C
• Wikidata: Q72448519
• Mol file: 99277-71-1.mol

Synonyms:4-Bromo-2-nitrobenzoic acid;99277-71-1;4-Bromo-2-nitrobenzoic acid;Benzoic acid, 4-bromo-2-nitro-;MFCD01013599;4-bromo-2-nitro-benzoic Acid;2-NITRO-4-BROMOBENZOIC ACID;SCHEMBL132963;F9995-0102;DTXSID20396250;ZIRHHEZLJGORGU-UHFFFAOYSA-N;4-Bromo-2-nitrobenzoic acid, 97%;AKOS015835481;AKOS034830327;AC-3919;CS-W002727;PS-3572;AM20060942;B3810;FT-0630198;EN300-99720;VU0549290-1;W-204186

Chemical Property of 4-Bromo-2-nitrobenzoic acid

Chemical Property:

• Vapor Pressure: 4.38E-06mmHg at 25°C
• Melting Point: 165-169 °C
• Boiling Point: 368.6 °C at 760 mmHg
• PKA: 1.97±0.25(Predicted)
• Flash Point: 176.7 °C
• PSA: 83.12000
• Density: 1.892 g/cm³
• LogP: 2.57870
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 244.93237
• Heavy Atom Count: 13
• Complexity: 227

Purity/Quality:

99% ^*data from raw suppliers

4-Bromo-2-nitrobenzoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N,Xi
• Hazard Codes: Xn,N,Xi
• Statements: 22-36/37/38-43-50
• Safety Statements: 26-36/37-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1Br)[N+](=O)[O-])C(=O)O
• Uses: 4-Bromo-2-nitrobenzoic acid is an intermediate in the synthesis of Lonafarnib (L469445), a potential anticancer agent. Undergoes Negishi-type coupling with dimethylzinc in the presence of palladium-phosphine catalysis.

Technology Process of 4-Bromo-2-nitrobenzoic acid

There total 14 articles about 4-Bromo-2-nitrobenzoic acid 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: 91.0%

4-amino-2-nitrobenzoic acid (610-36-6) → 4-bromo-2-nitrobenzoic acid (99277-71-1) + 1-tert-butyloxycarbonyl-4-trimethylstannyl-1,2,5,6-tetrahydropyridine (162046-38-0)

Guidance literature:

With sodium nitrite; copper(I) bromide; In water; hydrogen bromide;

Reference yield: 83.0%

4-bromo-2-nitrotoluene (60956-26-5) → 4-bromo-2-nitrobenzoic acid (99277-71-1)

Guidance literature:

With pyridine; tetra-n-butylammonium permanganate; at 20 ℃; for 5h;

DOI:10.1021/jm060590x

Reference yield:

4-amino-2-nitrobenzoic acid (610-36-6) → 4-bromo-2-nitrobenzoic acid (99277-71-1)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. HBr, NaNO₂ / 0 °C

2: CuBr, aq. HBr / 0 °C

With hydrogen bromide; copper(I) bromide; sodium nitrite;

DOI:10.1021/jo9622845

upstream raw materials:

4-bromo-2-nitrotoluene

4-bromo-2-nitro-benzonitrile

4-amino-2-nitrobenzoic acid

3-(1H-benzoimidazol-2-yl)-4-hydroxy-1H-[1,7]naphthyridin-2-one

Downstream raw materials:

2-amino-4-bromobenzoic acid

4-bromo-2,3-dinitro-benzoic acid

4-bromo-2,5-dinitro-benzoic acid

4-bromo-2-nitro-benzoyl chloride

Refernces

• 1、 Allison, Brett D.,Phuong, Victor K.,McAtee, Laura C.,Rosen, Mark,Morton, Magda,Prendergas, Clodagh,Barrett, Terry,Lagaud, Guy,Freedman, Jamie,Li, Na,Wu, Xiaodong,Venkatesan, Hariharan,Pippel, Marna,Woods, Craig,Rizzolio, Michèle C.,Hack, Michael,Hoey, Kenway,Deng, Xiaohu,King, Christopher,Shankley, Nigel P.,Rabinowitz, Michael H.. "Identification and optimization of anthranilic sulfonamides as novel, selective cholecystokinin-2 receptor antagonists". . p. 6371 - 6390. Retrieved 2008/04/18.
• 2、 -. "SULFONAMIDE COMPOUNDS". Page/Page column 29; 61. . Retrieved 2010/10/20.