Cas no 943-14-6 (2-Bromo-5-nitrobenzoic acid)

2-Bromo-5-nitrobenzoic acid is a brominated and nitrated aromatic carboxylic acid, primarily utilized as an intermediate in organic synthesis and pharmaceutical research. Its key structural features—a carboxylic acid group, bromo substituent, and nitro group at the 2- and 5-positions, respectively—make it a versatile building block for constructing complex molecules. The bromo group facilitates further functionalization via cross-coupling reactions, while the nitro group can be reduced to an amine for additional derivatization. This compound is particularly valuable in the development of agrochemicals, dyes, and active pharmaceutical ingredients (APIs), where precise substitution patterns are critical. Its high purity and stability ensure reliable performance in synthetic applications.
2-Bromo-5-nitrobenzoic acid structure
2-Bromo-5-nitrobenzoic acid structure
Product Name:2-Bromo-5-nitrobenzoic acid
CAS No:943-14-6
MF:C7H4BrNO4
MW:246.014961242676
MDL:MFCD00134558
CID:83241
PubChem ID:160871070
Update Time:2025-06-22

2-Bromo-5-nitrobenzoic acid Chemical and Physical Properties

Names and Identifiers

    • 2-Bromo-5-nitrobenzoic acid
    • 2-Bromo-5-nitrobenzoic acid (ACI)
    • NSC 52211
    • STK498191
    • 943-14-6
    • BP-13028
    • B3841
    • 2-Bromo-5-nitrobenzoicacid
    • SCHEMBL136718
    • NSC52211
    • NS00125827
    • AC-23548
    • Benzoic acid, 2-bromo-5-nitro-
    • EN300-59031
    • J-508409
    • CS-11276
    • 2-bromo-5-nitro benzoic acid
    • DTXSID40287691
    • Z277540502
    • AKOS000283684
    • 2-Bromo-5-nitrobenzic acid
    • SY013438
    • NSC-52211
    • BR1601
    • AO-801/41077413
    • CS-W002414
    • DTXCID70238838
    • 2-Bromo-5-nitro-benzoic acid
    • MFCD00134558
    • 2-Bromo-5-nitrobenzoic acid, 98%
    • MDL: MFCD00134558
    • Inchi: 1S/C7H4BrNO4/c8-6-2-1-4(9(12)13)3-5(6)7(10)11/h1-3H,(H,10,11)
    • InChI Key: UVFWYVCDRKRAJH-UHFFFAOYSA-N
    • SMILES: O=C(C1C(Br)=CC=C([N+](=O)[O-])C=1)O
    • BRN: 980242

Computed Properties

  • Exact Mass: 244.93200
  • Monoisotopic Mass: 244.932
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 227
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 83.1A^2
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing

Experimental Properties

  • Color/Form: Not determined
  • Density: 2.0176 (rough estimate)
  • Melting Point: 180.0 to 184.0 deg-C
  • Boiling Point: 370.5 °C at 760 mmHg
  • Flash Point: 177.8℃
  • Refractive Index: 1.6200 (estimate)
  • PSA: 83.12000
  • LogP: 2.57870
  • Solubility: Not determined

2-Bromo-5-nitrobenzoic acid Security Information

2-Bromo-5-nitrobenzoic acid Pricemore >>

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2-Bromo-5-nitrobenzoic acid Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Sulfuric acid ,  Nitric acid Solvents: Water ;  cooled; 1 h, < 5 °C
Reference
Donor-acceptor biaryl lactones: pH induced molecular switches with intramolecular charge transfer modulation
Carlson, Erik J.; Riel, Asia Marie S.; Dahl, Bart J., Tetrahedron Letters, 2012, 53(46), 6245-6249

Production Method 2

Reaction Conditions
1.1 Reagents: Sulfuric acid ,  Nitric acid Solvents: Water ;  < 5 °C; 1 h, < 5 °C
1.2 Reagents: Water ;  cooled
Reference
Preparation of pyrrolidinylchromenones as inhibitors of cyclin-dependent kinases
, United States, , ,

Production Method 3

Reaction Conditions
Reference
Benzamide derivatives with pharmacological properties
, Spain, , ,

Production Method 4

Reaction Conditions
1.1 Reagents: Sulfuric acid ,  Nitric acid Solvents: Water ;  < 5 °C; 1 h, < 5 °C
Reference
Preparation of pyrrolidinylchromenones as inhibitors of cyclin-dependent kinases.
, World Intellectual Property Organization, , ,

Production Method 5

Reaction Conditions
1.1 Reagents: Sulfuric acid ,  Permanganic acid (HMnO4), potassium salt (1:1)
Reference
Synthesis of lysergic acid. I. Derivatives of indole
Barltrop, J. A.; Taylor, D. A. H., Journal of the Chemical Society, 1954, 3399, 3399-3403

Production Method 6

Reaction Conditions
1.1 Reagents: Bromine ,  Potassium bromide
Reference
Syntheses of naphthoic mercury compounds and their reaction with nucleophilic reagents
Takahashi, Teruo, Yakugaku Zasshi, 1978, 98(3), 358-65

Production Method 7

Reaction Conditions
1.1 Reagents: Sodium bicarbonate ,  Permanganic acid (HMnO4), potassium salt (1:1) Solvents: Water ;  overnight, rt
Reference
Tandem copper catalyzed regioselective N-arylation-amidation: synthesis of angularly fused dihydroimidazoquinazolinones and the anticancer agent TIC10/ONC201
Honnanayakanavar, Jyoti M.; Nanubolu, Jagadeesh Babu; Suresh, Surisetti, Organic & Biomolecular Chemistry, 2021, 19(39), 8497-8501

Production Method 8

Reaction Conditions
Reference
The discovery of novel small molecule allosteric activators of aldehyde dehydrogenase 2
Tian, Wei; Guo, Jiapeng; Zhang, Qingsen; Fang, Shaoyu; Zhou, Ruolan; et al, European Journal of Medicinal Chemistry, 2021, 212,

Production Method 9

Reaction Conditions
Reference
Method for preparing 5-amino-2-bromobenzoic acid
, China, , ,

2-Bromo-5-nitrobenzoic acid Raw materials

2-Bromo-5-nitrobenzoic acid Preparation Products

Additional information on 2-Bromo-5-nitrobenzoic acid

Introduction to 2-Bromo-5-nitrobenzoic acid (CAS No. 943-14-6)

2-Bromo-5-nitrobenzoic acid (CAS No. 943-14-6) is a versatile organic compound with significant applications in various fields, including pharmaceuticals, chemical synthesis, and materials science. This compound is characterized by its unique molecular structure, which includes a bromine atom and a nitro group attached to a benzoic acid backbone. These functional groups contribute to its reactivity and potential utility in a wide range of chemical reactions and biological processes.

The molecular formula of 2-Bromo-5-nitrobenzoic acid is C7H4BrNO4, and its molecular weight is approximately 237.01 g/mol. The compound is a white to off-white crystalline solid at room temperature and is soluble in polar solvents such as water, methanol, and dimethyl sulfoxide (DMSO). Its physical and chemical properties make it an attractive candidate for various synthetic transformations and as a building block in the development of new materials and pharmaceuticals.

In the realm of pharmaceutical research, 2-Bromo-5-nitrobenzoic acid has garnered attention due to its potential as an intermediate in the synthesis of bioactive compounds. Recent studies have explored its use in the development of novel drugs targeting specific biological pathways. For instance, researchers have investigated the compound's ability to modulate enzyme activity and its potential as an inhibitor of certain enzymes involved in disease processes.

A study published in the Journal of Medicinal Chemistry highlighted the use of 2-Bromo-5-nitrobenzoic acid as a key intermediate in the synthesis of a series of novel anti-inflammatory agents. The compounds derived from this intermediate showed promising activity in reducing inflammation in vitro and in animal models. This research underscores the importance of 2-Bromo-5-nitrobenzoic acid as a valuable starting material for the development of new therapeutic agents.

Beyond pharmaceutical applications, 2-Bromo-5-nitrobenzoic acid has also found utility in materials science. Its unique electronic properties make it suitable for use in the synthesis of conductive polymers and other advanced materials. Researchers have explored its role in the development of organic semiconductors, which have potential applications in electronic devices such as organic light-emitting diodes (OLEDs) and solar cells.

In the context of chemical synthesis, 2-Bromo-5-nitrobenzoic acid serves as a versatile building block for constructing complex molecules. Its reactivity with various functional groups allows chemists to introduce multiple substituents at specific positions on the aromatic ring, leading to a wide array of structurally diverse compounds. This versatility has made it a popular choice for synthetic chemists working on the development of new materials and pharmaceuticals.

The safety profile of 2-Bromo-5-nitrobenzoic acid is an important consideration for its use in research and industrial applications. While it is generally considered safe when handled properly, standard laboratory safety protocols should be followed to minimize any potential risks. Proper storage conditions, such as keeping the compound away from heat sources and incompatible materials, are essential to ensure its stability and prevent any unintended reactions.

In conclusion, 2-Bromo-5-nitrobenzoic acid (CAS No. 943-14-6) is a multifaceted compound with significant potential across various scientific disciplines. Its unique molecular structure and reactivity make it an invaluable tool for researchers working on new drug development, materials science, and chemical synthesis. As ongoing research continues to uncover new applications and properties, the importance of this compound is likely to grow further.

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