4-Hydroxy-3-nitrobenzoic acid

Base Information

• Chemical Name: 4-Hydroxy-3-nitrobenzoic acid
• CAS No.: 616-82-0
• Molecular Formula: C7H5NO5
• Molecular Weight: 183.12
• Hs Code.: 2916.39 DERIVATION
• European Community (EC) Number: 210-494-1
• NSC Number: 78436
• UNII: 8SL84Q8B6C
• DSSTox Substance ID: DTXSID20210609
• Nikkaji Number: J95.687B
• Wikidata: Q72480674
• Metabolomics Workbench ID: 112994
• Mol file: 616-82-0.mol

Synonyms:4-HYDROXY-3-NITROBENZOIC ACID;616-82-0;3-Nitro-4-hydroxybenzoic acid;Benzoic acid, 4-hydroxy-3-nitro-;3-Nitro-4-hydrobenzoic acid;4-hydroxy-3-nitro-benzoic acid;8SL84Q8B6C;EINECS 210-494-1;MFCD00007119;NSC 78436;NSC-78436;4-Hydroxy-3-nitrobenzoicacid;NSC78436;UNII-8SL84Q8B6C;3,4-Nitrohydroxybenzoic acid;SCHEMBL106249;QRYSWXFQLFLJTC-UHFFFAOYSA-;DTXSID20210609;STL197510;4-Hydroxy-3-nitrobenzoic acid, 98%;AKOS003382446;CS-W017067;AC-10247;AS-12419;AM20040866;FT-0618646;H0910;EN300-53840;A833361;Q-200478;Z385458396

Chemical Property of 4-Hydroxy-3-nitrobenzoic acid

Chemical Property:

• Appearance/Colour: yellow to light brown powder
• Vapor Pressure: 1.24E-05mmHg at 25°C
• Melting Point: 183-186 °C(lit.)
• Refractive Index: 1.6280 (estimate)
• Boiling Point: 354.304 °C at 760 mmHg
• PKA: 3.94±0.10(Predicted)
• Flash Point: 162.528 °C
• PSA: 103.35000
• Density: 1.632 g/cm³
• LogP: 1.52180
• Storage Temp.: -20°C
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 183.01677226
• Heavy Atom Count: 13
• Complexity: 223

Purity/Quality:

98% ^*data from raw suppliers

4-Hydroxy-3-nitrobenzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C(=O)O)[N+](=O)[O-])O
• Uses: Standard in chymotrypsin assays

Technology Process of 4-Hydroxy-3-nitrobenzoic acid

There total 55 articles about 4-Hydroxy-3-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: 98.0%

4-chloro-3-nitrobenzoate (96-99-1) → 3-nitro-4-hydroxybenzoic acid (616-82-0)

Guidance literature:

With water; sodium hydroxide; at 100 ℃;

Reference yield: 98.0%

4-hydroxy-benzoic acid (99-96-7) → 3-nitro-4-hydroxybenzoic acid (616-82-0)

Guidance literature:

With magnesium(II) nitrate hexahydrate; AMA; at 20 ℃; for 1.5h; regioselective reaction; Neat (no solvent);

DOI:10.3184/030823408X390181

Reference yield: 93.0%

3-nitro-4-fluorobenzoic acid (453-71-4) → 3-nitro-4-hydroxybenzoic acid (616-82-0)

Guidance literature:

With acetylhydroxamic acid; potassium carbonate; In dimethyl sulfoxide; at 80 ℃; for 1h; Sealed tube;

DOI:10.1021/acs.orglett.6b00876

upstream raw materials:

3,4-Dihydroxybenzoic acid

1-methyl-4-nitrosobenzene

3,4-dinitrobenzoic acid

4-methoxycarbonylmethoxy-3-nitro-benzoic acid

Downstream raw materials:

4-butoxy-3-nitro benzoic acid

4-carboxy-2-nitrophenyl heptanoate

4-carboxy-2-nitrophenyl propanoate

3-nitro-4-(octanoyloxy)benzoic acid

Refernces

• 1、 Taniguchi et al.. "". . p. 829,830, 831. Retrieved 1978.
• 2、 Fier, Patrick S.,Maloney, Kevin M.. "Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions". supporting information. p. 2244 - 2247. Retrieved 2016/06/01.
• 3、 Potter, Garrett T.,Jayson, Gordon C.,Miller, Gavin J.,Gardiner, John M.. "Amyl nitrite-mediated conversion of aromatic and heteroaromatic primary amides to carboxylic acids". supporting information. p. 5153 - 5156. Retrieved 2015/08/19.