480-67-1

Basic information

• Product Name: 2,6-DIHYDROXY-4-METHYLBENZOIC ACID
• Synonyms: 2,6-dihydroxy-4-methyl-benzoicaci;4-methyl-2,6-dihydroxybenzoicacid;4-methyl-gamma-resorcylicaci;p-osellinicacid;2,6-DIHYDROXY-P-TOLUIC ACID;2,6-DIHYDROXY-4-METHYLBENZENECARBOXYLIC ACID;2,6-DIHYDROXY-4-METHYLBENZOIC ACID;P-ORCELLINIC ACID
• CAS NO: 480-67-1
• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.15
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid
• Mol File: 480-67-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 175.5 °C
• Boiling Point: 257.07°C (rough estimate)
• Flash Point: 188.5 °C
• Appearance: /
• Density: 1.3037 (rough estimate)
• Vapor Pressure: 5.9E-06mmHg at 25°C
• Refractive Index: 1.5090 (estimate)
• PKA: 1.46±0.14(Predicted)
• CAS DataBase Reference: 2,6-DIHYDROXY-4-METHYLBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIHYDROXY-4-METHYLBENZOIC ACID(480-67-1)
• EPA Substance Registry System: 2,6-DIHYDROXY-4-METHYLBENZOIC ACID(480-67-1)

Safety Data

• Hazard Codes: Xi
• RTECS: VH3709600
• HazardClass: IRRITANT
• Hazardous Substances Data: 480-67-1(Hazardous Substances Data)

Usage

General Description

2,6-Dihydroxy-4-Methylbenzoic Acid is a chemical compound that belongs to the family of benzoic acids and derivatives. These are organic compounds containing a benzene ring which bears at least one carboxyl group. This specific compound is unique because it has two hydroxy groups and one methyl group attached to its benzene ring along with the carboxyl group. Due to these substituent groups, this chemical exhibits unique physical and chemical properties which make it useful in various industrial and chemical procedures. While there isn't exhaustive information available about its uses, benzoic acids and their derivatives are typically utilized in a wide variety of chemical and industrial processes including serving as intermediates in the production of other chemicals.

InChI:InChI=1/C8H8O4/c1-4-2-5(9)7(8(11)12)6(10)3-4/h2-3,9-10H,1H3,(H,11,12)/p-1

Upstream product

• 504-15-4 orcinol 
• 15719-64-9 methylammonium carbonate 
• 13444-19-4 2,4-diacetyl-5-methyl-resorcinol 
• 519-57-3 sulochrin 
• 526-37-4 atranol 
• 541-41-3 chloroformic acid ethyl ester 
• 67-64-1 acetone 
• 124-38-9 carbon dioxide 
• 7732-18-5 water 
• 7664-93-9 sulfuric acid 
• 20982-28-9 5-methylbenzene-1,3-diyl diacetate 
• 298-14-6 potassium hydrogencarbonate 

Downstream Products

• 54130-89-1 2,6-dimethoxy-4-methyl-benzoic acid methyl ester 
• 57439-16-4 methyl 2-hydroxy-6-methoxy-4-methylbenzoate 
• 16846-10-9 methyl 2,6-dihydroxy-4-methylbenzoate 
• 51786-54-0 2,5-Dimethyl-7-hydroxy-chromon-8-carbonsaeure 
• 99986-98-8 3-dimethylaminomethyl-2,6-dihydroxy-4-methyl-benzoic acid 
• 106522-11-6 2,6-dihydroxy-4-methyl-3-phenylazo-benzoic acid 
• 504-15-4 orcinol 
• 33188-70-4 2,6-dimethoxy-3,4-dimethyl-benzoic acid methyl ester 
• 124-38-9 carbon dioxide 
• 488-87-9 2,5-dimethyl-1,3-benzenediol 
• 114561-50-1 acide hydroxy-2-methoxy-6-methyl-4-benzoique 

Relevant articles and documents

Design, Synthesis, and Herbicidal Activity of Pyrimidine-Biphenyl Hybrids as Novel Acetohydroxyacid Synthase Inhibitors

The issue of weed resistance to acetohydroxyacid synthase (EC 2.2.1.6, AHAS) inhibitors has become one of the largest obstacles for the application of this class of herbicides. In a continuing effort to discover novel AHAS inhibitors to overcome weed resistance, a series of pyrimidine-biphenyl hybrids (4aa-bb and 5aa-ah) were designed and synthesized via a scaffold hopping strategy. Among these derivatives, compounds 4aa (Ki = 0.09 μM) and 4bb (Ki = 0.02 μM) displayed higher inhibitory activities against Arabidopsis thaliana AHAS than those of the controls bispyribac (Ki = 0.54 μM) and flumetsulam (Ki = 0.38 μM). Remarkably, compounds 4aa, 4bb, 5ah, and 5ag exhibited excellent postemergence herbicidal activity and a broad spectrum of weed control at application rates of 37.5-150 g of active ingredient (ai)/ha. Furthermore, 4aa and 4bb showed higher herbicidal activity against AHAS inhibitor-resistant Descurainia sophia, Ammannia arenaria, and the corresponding sensitive weeds than that of bispyribac at 0.94-0.235 g ai/ha. Therefore, the pyrimidine-biphenyl motif and lead compounds 4aa and 4bb have great potential for the discovery of novel AHAS inhibitors to combat AHAS-inhibiting herbicide-resistant weeds.

An efficient method for syntheses of functionalized 6-bulkysubstituted salicylates under microwave irradiation

As an important fragment and synthetic intermediate, functionalized 6-arylsalicylate substructure widely exist in pharmacologically relevant natural products and bioactive compounds. In our recent works, we discovered two highly potent inhibitors for combating mutants of acetohydroxyacid synthase (AHAS), an important target for herbicide discovery. These two inhibitors contain 6-arylsalicylate skeleton. Previously, we have explored a new method to synthesize position-6 aryl substituted salicylic acid fragment. However, this method failed to synthesize 4-methyl-6-aryl salicylic acids. Herein, we developed a new efficient method for the synthesis of functionalized 4-methyl-6-bulkyarylsalicylates via a microwave-promoted Suzuki cross-coupling. This method has obvious advantages, such as a wide range of substrates, smooth and rapid reaction, moderate to excellent yields. Due to its superiority to the traditional available methods, this protocol could be utilized to synthesize pyrimidinyl(thio)salicylic acid and its derivatives.