75056-97-2

Basic information

• Product Name: 4-Hydroxy-2,6-dimethylbenzoic acid
• Synonyms: RARECHEM AL BO 0854;2,6-dimethyl-4-hydroxybenzoic acid;4-HYDROXY-2,6-DIMETHYLBENZOIC ACID
• CAS NO: 75056-97-2
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• Product Categories: pharmacetical
• Mol File: 75056-97-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 178°C
• Boiling Point: 345oC at 760 mmHg
• Flash Point: 176.6oC
• Appearance: /
• Density: 1.249g/cm3
• Vapor Pressure: 2.41E-05mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.12±0.37(Predicted)
• CAS DataBase Reference: 4-Hydroxy-2,6-dimethylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-2,6-dimethylbenzoic acid(75056-97-2)
• EPA Substance Registry System: 4-Hydroxy-2,6-dimethylbenzoic acid(75056-97-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 75056-97-2(Hazardous Substances Data)

Usage

General Description

4-Hydroxy-2,6-dimethylbenzoic acid, also known as homoveratric acid, is a chemical compound with the molecular formula C9H10O4. It is a derivative of benzoic acid and contains a hydroxyl group and two methyl groups attached to the benzene ring. 4-Hydroxy-2,6-dimethylbenzoic acid is found in various natural sources such as certain plant species and is used in the synthesis of pharmaceuticals and other organic compounds. It has been studied for its potential antioxidant and antimicrobial properties, and its structure makes it a valuable building block in organic chemistry.

InChI:InChI=1/C9H10O3/c1-5-3-7(10)4-6(2)8(5)9(11)12/h3-4,10H,1-2H3,(H,11,12)

Upstream product

• 124-38-9 carbon dioxide 
• 95741-44-9 1-((4-bromo-3,5-dimethylphenoxy)methyl)benzene 
• 378185-88-7 tert-butyl(4-iodo-3,5-dimethylphenoxy)dimethylsilane 
• 80826-86-4 4-iodo-3,5-dimethylphenol 
• 95741-45-0 4-(benzyloxy)-2,6-dimethylbenzoic acid 
• 28924-92-7 4-(benzyloxy)-2,6-dimethylbenzaldehyde 
• 378185-89-8 4-(tert-butyldimethylsilanyloxy)-2,6-dimethylbenzaldehyde 
• 19447-00-8 4-methoxy-2,6-dimethylbenzylaldehyde 
• 70547-87-4 2,6-dimethyl-4-hydroxybenzaldehyde 
• 87513-48-2 2,4-dinitrophenyl 4-hydroxy-2,6-dimethylbenzoate 
• 76139-75-8 N-(5-ethyl-2-methyl-1-oxido-4-pyridyl)-2-acetyl-3,5-dimethylphenol-4-carboxamide 
• 37934-89-7 2,6-Dimethyl-4-methoxybenzoic acid 
• 75056-98-3 ethyl 4-hydroxy-2,6-dimethyl benzoate 

Downstream Products

• 83194-70-1 methyl 4-hydroxy-2,6-dimethylbenzoate 
• 1351163-93-3 4-(acetyloxy)-2,6-dimethylbenzoic acid 
• 1351163-96-6 methyl {4-chloro-3-[(4-hydroxy-2,6-dimethylbenzoyl)amino]phenyl}acetate 
• 1351163-95-5 methyl (3-{[4-(acetyloxy)-2,6-dimethylbenzoyl]amino}-4-chlorophenyl)acetate 
• 1351163-94-4 4-(chlorocarbonyl)-3,5-dimethylphenyl acetate 
• 1356963-69-3 C₂₇H₂₆ClNO₆ 
• 760162-74-1 C₂₉H₃₈F₃N₃O₂ 
• 306296-06-0 C₃₅H₄₂F₃N₃O₃ 

Relevant articles and documents

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Reactivity in the Para Oxo Ketene Route of Ester Hydrolysis. The Effect of Internal Nucleophilicity and the Irrelevance of B Strain

The hydrolysis of 2,4-dinitrophenyl (DNP) esters of substituted 4-hydroxybenzoic acids obeys the equation kobsd = (ka + kb->)/(1 + +>/Ka) and involves a para oxo ketene intermediate.The ka term fits a Broensted equation against the pK of the 4-hydroxybenzoate (log ka = 1.15pKa - 11.71) provided the 2,6-positions of the benzoate are free.The ka term for the 2,6-dimethyl-4-hydroxybenzoate ester is 1015-fold larger than that for the parent 4-hydroxybenzoate ester.An electronic effect due to different hydroxyl pKa's may be calculated from the above linear free energy relationship to contribute 1.6percent of the discrepancy.The other component of the discrepancy is ascribed to a preferred alignment of the ester in the 2,6-dimethyl case perpendicular to the plane of the aromatic ring. The fused ketene in the microscopic reverse reaction has a LUMO acceptor orbital perpendicular to the plane of the ring, in agreement with our conclusions.Force-field calculations of nonbonding interactions indicate no strain release in the elimination mechanism giving rise to ka.The dramatic (107-fold) enhancement of the apparent second-order rate constant for alkaline hydrolysis of the 2,6-dimethyl ester compared with that of the corresponding 2',4'-dinitrophenyl 4-methoxy-2,6-dimethylbenzoate is due mostly to the steric strain imposed in the tetrahedral transition state for the latter reaction.This strain is not sufficient, however, to cause the normal BAc2 mechanism in the alkaline hydrolysis of mesitoates to change to a "square planar" concerted process.

Syntheses of 4-Hydroxy-2,6-dimethylbenzoic Acid and Its Higher Homologues

Syntheses of 4-hydroxy-2,6-dimethylbenzoic acid (2a) and its higher homologues, viz 4-hydroxy-2,6-dimethylphenylacetic acid (2b), 3-(4-hydroxy-2,6-dimethylphenyl)propanoic acid (2c) and 4-(4-hydroxy-2,6-dimethylphenyl)butanoic acid (2d) are described.