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167037

Sigma-Aldrich

3-Methylsalicylic acid

96.0%

Synonym(s):

2-Hydroxy-3-methylbenzoic acid, o-Cresotic acid

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About This Item

Linear Formula:
CH3C6H3(OH)CO2H
CAS Number:
83-40-9
Molecular Weight:
152.15
Beilstein:
2086811
EC Number:
201-473-8
MDL number:
MFCD00002448
UNSPSC Code:
12352100
PubChem Substance ID:
24850191
NACRES:
NA.22

Assay

96.0%

mp

163-165 °C (lit.)

solubility

methanol: soluble 5%, clear to slightly hazy (colorlessto faint brown)

SMILES string

Cc1cccc(C(O)=O)c1O

InChI

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

InChI key

WHSXTWFYRGOBGO-UHFFFAOYSA-N

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General description

3-Methylsalicylic acid reacts with WOCl4 to yield tungsten(VI) oxo-salicylate complexes.

Application

3-Methylsalicylic acid was used in the synthesis of:
  • 8-methyl-2-thioxo-2,3-dihydro-4H-1,3-benzoxazin-4-one
  • 7-hydroxy-8-methyl-2-thioxo-2,3-dihydro-4H-1,3-benzoxazin-4-one
  • (R)-, (S)- and (RS)-hydroxymethylmexiletine

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H318,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Krithika Delhiraja et al.
Environmental monitoring and assessment, 192(7), 432-432 (2020-06-17)
Emerging contaminants (ECs) have become an increasing area of concern due to the likely impacts of these compounds on human health and the environment. Generally, products which are used for households and personal care activities contribute to major percentage of
Generalized Method for the Production of 1, 3-Benzoxazine, 1, 3-Benzothiazine, and Quinazoline Derivatives from 2-(Hydroxy, Thio, or Amino) Aromatic Acids Using Triphenylphosphine Thiocyanogen.
Pritchard KM, et al.
Synthetic Communications, 35(!2), 1601-1611 (2005)
Warren B Cross et al.
Dalton transactions (Cambridge, England : 2003), (7)(7), 1287-1293 (2005-03-23)
Tungsten(VI) oxo-salicylate complexes were prepared in moderate yield (47 to 63%) by the reactions of WOCl4 and two equivalents of either 3-methylsalicylic acid (MesaliH2) or 3,5-di-isopropylsalicylic acid (di-i-PrsaliH2). Performing the reaction in refluxing toluene afforded the two analogous ditungsten complexes
Synthesis of (R)-, (S)-, and (RS)-hydroxymethylmexiletine, one of the major metabolites of mexiletine.
Cavalluzzi MM, et al.
Tetrahedron Asymmetry, 18(20), 2409-2417 (2007)
On structure-related properties of synthetic organic clot-dissolving (thrombolytic) compounds.
K N von Kaulla et al.
Biochemical pharmacology, 16(6), 1023-1034 (1967-06-01)
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