2-Hydroxy-6-methylbenzoic acid
- Iupac Name：2-hydroxy-6-methylbenzoic acid
- CAS No.: 567-61-3
- Molecular Weight：152.14732
- Modify Date.: 2022-11-29 07:14
- Introduction:
White solid
6-methylsalicylic acid is a monohydroxybenzoic acid that is salicylic acid in which the hydrogen ortho to the carboxylic acid group is substituted by a methyl group. It has a role as a Penicillium metabolite and a plant metabolite. It derives from a salicylic acid. It is a conjugate acid of a 6-methylsalicylate.
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1. Names and Identifiers
- 1.1 Name
- 2-Hydroxy-6-methylbenzoic acid
- 1.2 Synonyms
2,6-Cresotic acid 2,6-cresoticacid 2-HYDROXY-6-METHYLBENZOIC ACID 6-Hydroxy-2-methylbenzoic acid 6-Hydroxy-o-toluic acid 6-Methylsalicylic acid 6-Methylsalicylic acid, 2-Carboxy-3-hydroxytoluene, 2-Carboxy-3-methylphenol 6-ms 6-msa Benzoic acid, 2-hydroxy-6-methyl- NSC 403256
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- 1.3 CAS No.
- 567-61-3
- 1.4 CID
- 11279
- 1.5 Molecular Formula
- C8H8O3 (isomer)
- 1.6 Inchi
- InChI=1S/C8H8O3/c1-5-3-2-4-6(9)7(5)8(10)11/h2-4,9H,1H3,(H,10,11)
- 1.7 InChIkey
- HCJMNOSIAGSZBM-UHFFFAOYSA-N
- 1.8 Canonical Smiles
- CC1=C(C(=CC=C1)O)C(=O)O
- 1.9 Isomers Smiles
- CC1=C(C(=CC=C1)O)C(=O)O
2. Properties
- 2.1 Density
- 1.304
- 2.1 Melting point
- 173.0 °C
- 2.1 Boiling point
- 300.4 °C at 760 mmHg
- 2.1 Refractive index
- 1.6
- 2.1 Flash Point
- 149.7 °C
- 2.1 PSA
- 57.53000
- 2.1 logP
- 1.39880
- 2.1 Chemical Properties
- White solid 2-Hydroxy-6-methylbenzoic acid Preparation Products And Raw materials Raw materials
- 2.2 pKa
- pK1:3.32 (25°C)
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- General procedure: Thionyl chloride (1.46 mL, 20.0 mmol) was added to a suspension of salicylic acid (4.0 mmol) in DCM (20 mL), followed by a catalytic amount of DMF (0.80 mmol). The reaction mixture was stirred overnight at room temperature. The solvent and residual thionyl chloride were removed under reduced pressure and the crude residue was used immediately without further purification. The crude was resuspended in DCM (20 mL), 4-aminobenzonitrile (945 mg, 8.0 mmol) was added and the reaction mixture was stirred overnight at room temperature. The mixture was diluted with DCM, washed with 1M HCl solution, brine, dried (MgSO4) and evaporated to dryness under reduced pressure. Chromatography (hexanes in ethyl acetate 0-100%) afford the salicylamides.
4. Safety and Handling
- 4.1 Specification
-
6-Methylsalicylic acid , its CAS NO. is 567-61-3, the synonyms are 2-Hydroxy-6-methylbenzoic acid ; 4-10-00-00594 (Beilstein Handbook Reference) ; 6-Hydroxy-o-toluic acid ; 6-MS ; 6-MSA ; BRN 2208693 ; NSC 403256 ; 2,6-Cresotic acid ; Benzoic acid, 2-hydroxy-6-methyl- (9CI) .
- 4.2 Toxicity
-
| Organism |
Test Type |
Route |
Reported Dose (Normalized Dose) |
Effect |
Source |
| mouse |
LD50 |
oral |
250mg/kg (250mg/kg) |
|
Acta Pharmaceutica Suecica. Vol. 7, Pg. 289, 1970. |
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5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
no data available
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | no data available |
| Signal word | no data available |
| Hazard statement(s) | no data available |
| Precautionary statement(s) | |
| Prevention | no data available |
| Response | no data available |
| Storage | no data available |
| Disposal | no data available |
2.3 Other hazards which do not result in classification
no data available
6. Synthesis Route
567-61-3Total: 23 Synthesis Route
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Literatures:
Nippon Nogei Kagaku Kaishi, , vol. 9, p. 1059,1061 Chem.Abstr., , p. 1073 Nippon Nogei Kagaku Kaishi, , vol. 10, p. 703,709 Chem.Abstr., , p. 160 Bulletin of the Agricultural Chemical Society of Japan, , vol. 9, p. 148,149
Yield: ~%
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7. Other Information
- 7.0 Mesh Entry Terms
- 6-methylsalicylic acid
- 7.1 Use Classification
- Polyketides [PK] -> Aromatic polyketides [PK13] -> Monocyclic aromatic polyketides [PK1301]
8. Computational chemical data
- Molecular Weight: 152.14732g/mol
- Molecular Formula: C8H8O3
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 152.047344113
- Monoisotopic Mass: 152.047344113
- Complexity: 155
- Rotatable Bond Count: 1
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 57.5
- Heavy Atom Count: 11
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBwMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAACAAADASAmAAyDoAAAgCIAiDSCAACAAAkIAAIiAEGCMgIJzaCFRKAcUAl4BEImQeIyLCOgAABAAAYAAAAAAIAADAAAAAAAAAAAA==
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10. Realated Product Infomation
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