4-Bromo-2-hydroxybenzoic acid CAS 1666-28-0

Introduction：Basic information about 4-Bromo-2-hydroxybenzoic acid CAS 1666-28-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

4-Bromo-2-hydroxybenzoic acid Basic information

• Product Name: 4-Bromo-2-hydroxybenzoic acid
• Synonyms: 4-BROMOSALICYLIC ACID;4-BROMO-2-HYDROXYBENZOIC ACID;4-Bromo-2-Hydroxybenzoic Acid 2-Hydroxy-4-Bromobenzoic Acid;2-Hydroxy-4-bromobenzoicacid;4-Bromo-2-hydroxybenzoic acid 98%;4-Bromosalicyclic acid;4-Bromosalicylic acid, 5-Bromo-2-carboxyphenol;4-Bromosalicylic acid, >=98%
• CAS: 1666-28-0
• MF: C7H5BrO3
• MW: 217.02
• EINECS: 624-267-3
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Acids & Esters;Bromine Compounds
• Mol File: 1666-28-0.mol

4-Bromo-2-hydroxybenzoic acid Chemical Properties

• Melting point: 164-165°C
• Boiling point: 330.2±32.0 °C(Predicted)
• density: 1.861±0.06 g/cm3(Predicted)
• storage temp.: Keep in dark place,Inert atmosphere,Room temperature
• form: powder
• pka: 2.71±0.10(Predicted)
• color: Orange
• InChI: InChI=1S/C7H5BrO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,(H,10,11)
• InChIKey: FYAKLZKQJDBBKW-UHFFFAOYSA-N
• SMILES: C(O)(=O)C1=CC=C(Br)C=C1O
• CAS DataBase Reference: 1666-28-0(CAS DataBase Reference)

Safety Information

• Hazard Codes: Xi,Xn
• Risk Statements: 22-52/53
• Safety Statements: 22-24/25-61
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• HS Code: 2918290090
• Storage Class: 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
• Hazard Classifications: Acute Tox. 3 Oral

4-Bromo-2-hydroxybenzoic acid Usage And Synthesis

Structure

4-Bromo-2-hydroxybenzoic acid is almost planar (r.m.s. deviation for the non-H atoms = 0.035 Å) and an intra­molecular O—H⋯O hydrogen bond closes an S(6) ring. The plane defined by the non-H atoms of the carboxyl group is twisted slightly by 4.8 (4)° to the mean plane of the phenyl ring. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate (8) loops. Short Br⋯Br contacts [3.4442 (5) Å] between the mol­ecules of the adjacent (8) dimers leads to a one-dimensional architecture.

Chemical Properties

4-Bromo-2-hydroxybenzoic acid is a solid at normal temperature and pressure. It is stable at normal temperature and decomposes into phenol and carbon dioxide after rapid heating. It has some acidic properties.

Uses

2-Hydroxy-4-bromobenzoic acid is used as an anti-scorch agent in drug molecules and rubber industry, as well as an intermediate in the production of ultraviolet absorbers and foaming agents.

Synthesis

Under nitrogen atmosphere, add copper (II) bromide (8.8 g, 39.4 mmol, 1.2 equivalents), acetonitrile (50 ml), and 4-aminosalicylic acid (5.1 g, 49.5 mmol) to the vacuum-dried reaction flask, 1.5 equivalent). The reaction mixture was cooled to 0°C, and 2-hydroxy-4-bromobenzoic acid precursor (5.0 g, 32.6 mmol, 1.0 equiv) was added portion-wise. Additional acetonitrile (25 mL) was added to the mixture and stirred at 0 °C for 2 h. The organic extracts were combined and washed with 20% aqueous hydrochloric acid, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was dissolved in diethyl ether, and the resulting solution was extracted with 15% sodium hydroxide aqueous solution. The aqueous solution was washed with diethyl ether, acidified to pH 1 with 6N hydrochloric acid aqueous solution, and the mixture was extracted with diethyl ether. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was treated with chloroform, and the precipitate collected by filtration was 4-Bromo-2-hydroxybenzoic acid.

References

[1] Patent: EP1424336, 2004, A1. Location in patent: Page 136
[2] Patent: WO2006/44775, 2006, A2. Location in patent: Page/Page column 16
[3] Nippon Kagaku Zasshi, 1957, vol. 78, p. 1608,1612
[4] Chem.Abstr., 1959, p. 21342
[5] Journal of Medicinal Chemistry, 1992, vol. 35, # 4, p. 734 - 740

4-Bromo-2-hydroxybenzoic acid Preparation Products And Raw materials

• Raw materials: 2-Acetamidophenol-->2-Bromo-6-hydroxybenzoic acid-->4-Bromo-2-hydroxybenzaldehyde-->4-BROMO-2-METHOXYBENZOIC ACID-->3-Hydroxybenzoic acid-->Phenol-->Carbon dioxide-->2-Nitrophenol-->2-Aminophenol-->Potassium bicarbonate-->Salicylic acid
• Preparation Products: 2-hydroxy-4-(4-pyridyl)benzoic acid-->3,3'-dihydroxy-[1,1'-biphenyl]-4,4'-dicarboxylic acid-->METHYL 4-BROMO-2-HYDROXYBENZOATE-->4-formyl-3-methoxybenzonitrile