50-85-1

Basic information

• Product Name: 4-Methylsalicylic acid
• Synonyms: 2,4-cresoticacid;2-hydroxy-4-methyl-benzoicaci;4-Methyl-2-hydroxybenzoic acid;Benzoic acid, 2-hydroxy-4-methyl-;gamma-Cresotic acid;gamma-cresoticacid;m-Homosalicylic acid;m-homosalicylicacid
• CAS NO: 50-85-1
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• EINECS: 200-068-3
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Aromatics
• Mol File: 50-85-1.mol
• Article Data: 17

Chemical Properties

• Melting Point: 173-177 °C(lit.)
• Boiling Point: 234.6°C (rough estimate)
• Flash Point: 158.6 °C
• Appearance: White to grayish-beige/Powder
• Density: 1.2143 (rough estimate)
• Vapor Pressure: 0.000188mmHg at 25°C
• Refractive Index: 1.4945 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)
• PKA: pK1:3.17 (25°C)
• Water Solubility: Soluble in water 10 g/L @ 20℃.
• Merck: 14,2580
• BRN: 2208140
• CAS DataBase Reference: 4-Methylsalicylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylsalicylic acid(50-85-1)
• EPA Substance Registry System: 4-Methylsalicylic acid(50-85-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: GP3920100
• Hazardous Substances Data: 50-85-1(Hazardous Substances Data)

Usage

Chemical Properties

4-Methylsalicylic acid is white to greyish-beige powder

Uses

Different sources of media describe the Uses of 50-85-1 differently. You can refer to the following data:
1. 4-Methylsalicylic acid is similar to salicylic acid. Used in manufacturing of dyes.
2. In manufacture of dyes.
3. 4-Methylsalicylic acid was used to inhibit the medium chain acyl- CoA synthetase.

Definition

4-Methylsalicylic acid is a monohydroxybenzoic acid consisting of salicylic acid having a methyl group at the 4-position.

General Description

The heteroleptic tris-cyclometalated iridium(III) complex with 4-methylsalicylic acid (Msal) was synthesized and characterized.

Purification Methods

Crystallise the acid from water. It sublimes at 130o/11mm. [Beilstein 10 H 233, 10 II 137, 10 III 521, 10 IV 617.]

InChI:InChI=1/C8H8O3/c1-5-2-3-6(8(10)11)7(9)4-5/h2-4,9H,1H3,(H,10,11)/p-1

Upstream product

• 3098-18-8 2-hydroxy-4-methylbenzophenone 
• 5331-40-8 1-(2-hydroxy-4-methyl-phenacyl)-pyridinium; iodide 
• 75-44-5 phosgene 
• 108-39-4 3-methyl-phenol 
• 124-38-9 carbon dioxide 
• 7697-27-0 2-bromo-4-methylbenzoic acid 
• 15719-64-9 methylammonium carbonate 
• 95-87-4 2,5-Dimethylphenol 
• 583-80-2 4-methyltropolone 
• 96945-60-7 4-methyl-6-sulfobenzoic acid 
• 137937-50-9 2-chloro-1-(2-hydroxy-4-methylphenyl)-1-propanone 
• 7722-84-1 dihydrogen peroxide 
• 116557-45-0 1-(2-hydroxy-4-methylphenyl)-2-methylpropan-1-one 
• 19814-69-8 3,6-dimethylxanthen-9-one 

Downstream Products

• 4670-56-8 methyl 2-hydroxy-4-methylbenzoate 
• 40547-32-8 1,3-dihydroxy-6-methyl-9H-xanthen-9-one 
• 60770-00-5 ethyl 4-methylsalicylate 
• 117571-33-2 4-methyl-2-(phenylmethoxy)benzoic acid 
• 1027591-17-8 (S)-2-{(S)-2-[(S)-2-(2-Hydroxy-4-methyl-benzoylamino)-3-methyl-butyrylamino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid methyl ester 
• 210174-43-9 4-Bromomethyl-2-hydroxy-benzoic acid 
• 4436-02-6 4-hydroxy-6-methyl-isophthalic acid 
• 17276-91-4 2-hydroxy-4-methyl-5-nitro-benzoic acid 
• 700-38-9 2-nitro-5-methylphenol 
• 6623-36-5 3,5-dibromo-2-hydroxy-4-methyl-benzoic acid 
• 4619-74-3 2,4,6-tribromo-m-cresol 
• 29666-53-3 3,5,6-tribromotoluquinone 
• 6623-35-4 5-bromo-2-hydroxy-4-methylbenzoic acid 
• 859178-20-4 2-hydroxy-4-methyl-5-(1,2,2,2-tetrachloro-ethyl)-benzoic acid 

Relevant articles and documents

Synthesis of cresotic acids by carboxylation of cresols with sodium ethyl carbonate

Carboxylation of o-cresol, m-cresol, and p-cresol with sodium ethyl carbonate (SEC) proceeds regioselectively with the formation of cresotic acids: 2-hydroxy-3-methylbenzoic acid, 2-hydroxy-4-methylbenzoic acid, and 2-hydroxy-5-methylbenzoic acid, respectively. Optimal conditions for conducting the process have been found to be as follows: the reactants ratio of [cresol]: [sodium ethyl carbonate] = (1.5–2): 1, T = 180–185°C, PCO2 = 10 atm, and t = 6–7 h. Simple and convenient methods for the synthesis of cresotic acids, which can be used for their industrial manufacturing, have been developed.

Carboxylation of Phenols with CO2 at Atmospheric Pressure

A convenient and efficient method for the ortho-carboxylation of phenols under atmospheric CO2 pressure has been developed. This method provides an alternative to the previously reported Kolbe-Schmitt method, which requires very high pressures of CO2. The addition of a trisubstituted phenol has proved essential for the successful carboxylation of phenols with CO2 at standard atmospheric pressure, allowing the efficient preparation of a broad variety of salicylic acids.

Regioselective ortho-carboxylation of phenols catalyzed by benzoic acid decarboxylases: A biocatalytic equivalent to the Kolbe-Schmitt reaction

The enzyme catalyzed carboxylation of electron-rich phenol derivatives employing recombinant benzoic acid decarboxylases at the expense of bicarbonate as CO2 source is reported. In contrast to the classic Kolbe-Schmitt reaction, the biocatalytic equivalent proceeded in a highly regioselective fashion exclusively at the ortho-position of the phenolic directing group in up to 80% conversion. Several enzymes were identified, which displayed a remarkably broad substrate scope encompassing alkyl, alkoxy, halo and amino- functionalities. Based on the crystal structure and molecular docking simulations, a mechanistic proposal for 2,6-dihydroxybenzoic acid decarboxylase is presented.