2,3-Dihydroxybenzoic acid

Base Information

• Chemical Name: 2,3-Dihydroxybenzoic acid
• CAS No.: 303-38-8
• Molecular Formula: C7H6O4
• Molecular Weight: 154.122
• Hs Code.: 29182900
• European Community (EC) Number: 206-139-5
• NSC Number: 27435
• UNII: 70D5FBB392
• DSSTox Substance ID: DTXSID70858712
• Nikkaji Number: J79.590I
• Wikipedia: 2,3-Dihydroxybenzoic_acid
• Wikidata: Q2823200
• Metabolomics Workbench ID: 37234
• ChEMBL ID: CHEMBL1432
• Mol file: 303-38-8.mol

Synonyms:2,3-dihydroxy benzoic acid;2,3-dihydroxybenzoate;2,3-dihydroxybenzoic acid;2-pyrocatechuic acid;2-pyrocatechuic acid, sodium salt;dihydroxybenzoic acid;ferri-2,3-dihydroxybenzoic acid;o-pyrocatechuic acid

Chemical Property of 2,3-Dihydroxybenzoic acid

Chemical Property:

• Appearance/Colour: pale brownish to red brownish crystalline powder
• Vapor Pressure: 6.85E-06mmHg at 25°C
• Melting Point: 204-206 °C(lit.)
• Refractive Index: 1.6400 (estimate)
• Boiling Point: 362.5 °C at 760 mmHg
• PKA: pK1:2.98;pK2:10.14 (30°C)
• Flash Point: 187.2 °C
• PSA: 77.76000
• Density: 1.559 g/cm³
• LogP: 0.79600
• Storage Temp.: 2-8°C
• Solubility.: methanol: soluble50mg/mL, clear to faintly hazy, orange
• Water Solubility.: Soluble in water, methanol and dimethyl sulfoxide.
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 154.02660867
• Heavy Atom Count: 11
• Complexity: 157

Purity/Quality:

99% ^*data from raw suppliers

2,3-Dihydroxybenzoic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Benzoic Acid Derivatives
• Canonical SMILES: C1=CC(=C(C(=C1)O)O)C(=O)O
• Uses: 2,3-Dihydroxybenzoic Acid is a selected phenol as MMP (Matrix Metalloproteinase) inhibitor. 2,3-Dihydroxybenzoic acid was used to study the complexes of manganese with aliphatic and aromatic polyhydroxy ligands in basic media by electrochemical, spectrophotometric and magnetic methods. It was used in isolation of new siderophore named vulnibactin from low iron cultures of Vibrio vulnificus, a human pathogen. It was used as cocrystal former to study the influence of position isomerism on the co-crystals formation and physicochemical properties of piracetam.

Technology Process of 2,3-Dihydroxybenzoic acid

There total 59 articles about 2,3-Dihydroxybenzoic 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: 9.0%

benzoic acid (65-85-0,8013-63-6) → 2,3-Dihydroxybenzoic acid (303-38-8) + 2,5-dihydroxybenzoic acid. (490-79-9) + 3-Carboxyphenol (99-06-9) + 4-hydroxy-benzoic acid (99-96-7)

Guidance literature:

With oxygen; iron(II) sulfate; In water; at 40 ℃; for 3h; Further byproducts given;

Reference yield: 4.0%

benzoic acid (65-85-0,8013-63-6) → 2,3-Dihydroxybenzoic acid (303-38-8) + 2,5-dihydroxybenzoic acid. (490-79-9) + 3-Carboxyphenol (99-06-9) + salicylic acid (69-72-7,25496-36-0,8052-31-1) + 4-hydroxy-benzoic acid (99-96-7)

Guidance literature:

With oxygen; iron(II) sulfate; In water; at 40 ℃; for 3h; Product distribution; pH 6.8 buffer;

Reference yield:

benzoic acid (65-85-0,8013-63-6) → 2,3-Dihydroxybenzoic acid (303-38-8) + 2,5-dihydroxybenzoic acid. (490-79-9) + 2,3,4-trihydroxybenzoic acid (610-02-6) + 3-Carboxyphenol (99-06-9) + salicylic acid (69-72-7,25496-36-0,8052-31-1) + 4-hydroxy-benzoic acid (99-96-7)

Guidance literature:

With hydrogenchloride; oxygen; iron(III) chloride; In water; Product distribution; Rate constant; Mechanism; hydroxylation by electrochemical Fenton reaction at pH=1, reaction time dependence;

DOI:10.1021/j100038a029

upstream raw materials:

3-formylsalicylic acid

2-hydroxy-3-iodobenzoic acid

3-methoxysalicylic acid

2,3-dimethoxybenzoic acid

Downstream raw materials:

benzo[1,3]dioxole-4-carboxylic acid

2,3-dihydroxybenzoicacid ethylester

Tetrabromocatechol

2,3-dihydroxy-5-bromobenzoic acid

Refernces

• 1、 Peralta,Roa,Hernandez-Servin,Romero,Balderas,Natividad. "Hydroxyl Radicals quantification by UV spectrophotometry". . p. 137 - 141. Retrieved 2014.
• 2、 Gao, Lijuan,Li, Jinyou,Qi, Jianhua. "Gentisides A and B, two new neuritogenic compounds from the traditional Chinese medicine Gentiana rigescens Franch". . p. 2131 - 2134. Retrieved 2010.
• 3、 Cason,Dyke. "". . p. 621. Retrieved 1950.
• 4、 Lang, Kamil,Brodilova, Jirina,Lunak, Stanislav. "Photochemical hydroxylation of salicylic acid with hydrogen peroxide; mechanistic study of substrate sensitized reaction". . p. 1729 - 1737. Retrieved 1996.
• 5、 Plodinec, Milivoj,Gr?i?, Ivana,Willinger, Marc G.,Hammud, Adnan,Huang, Xing,Pan?i?, Ivana,Gajovi?, Andreja. "Black TiO2 nanotube arrays decorated with Ag nanoparticles for enhanced visible-light photocatalytic oxidation of salicylic acid". . p. 883 - 896. Retrieved 2018/11/10.
• 6、 Nyúl, Eszter,Kuzma, Mónika,Mayer, Mátyás,Lakatos, Sándor,Almási, Attila,Perjési, Pál. "HPLC study on Fenton-reaction initiated oxidation of salicylic acid. Biological relevance of the reaction in intestinal biotransformation of salicylic acid". . p. 1040 - 1051. Retrieved 2018/10/24.