M-Toluic acid

Base Information

• Chemical Name: M-Toluic acid
• CAS No.: 99-04-7
• Molecular Formula: C8H8O2
• Molecular Weight: 136.15
• Hs Code.: 29163900
• European Community (EC) Number: 202-723-9
• NSC Number: 2214
• UNII: 1UA7K8EEXT
• DSSTox Substance ID: DTXSID1021617
• Nikkaji Number: J47.804K
• Wikipedia: M-Toluic_acid
• Wikidata: Q1241221
• Metabolomics Workbench ID: 53540
• ChEMBL ID: CHEMBL67450
• Mol file: 99-04-7.mol

Synonyms:3-methylbenzoic acid;3-toluic acid;3-toluic acid, barium salt;3-toluic acid, cadmium salt;3-toluic acid, zinc salt;m-toluate;m-toluic acid

Chemical Property of M-Toluic acid

Chemical Property:

• Appearance/Colour: off-white crystalline solid
• Vapor Pressure: 0.00506mmHg at 25°C
• Melting Point: 108 °C
• Refractive Index: 1.509
• Boiling Point: 263.8 °C at 760 mmHg
• PKA: 4.27(at 25℃)
• Flash Point: 120 °C
• PSA: 37.30000
• Density: 1.151 g/cm³
• LogP: 1.69320
• Storage Temp.: Store below +30°C.
• Solubility.: Soluble in alcohol and ether.
• Water Solubility.: <0.1 g/100 mL at 19℃
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 136.052429494
• Heavy Atom Count: 10
• Complexity: 131

Purity/Quality:

99% ^*data from raw suppliers

m-Toluic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC1=CC(=CC=C1)C(=O)O
• Description: m-toluic acid (MTA) , also known as 3-Methylbenzoic acid or m-Toluate, is a benzoic acid derivative having a floral honey odour. Benzoic acids are organic Compounds containing a benzene ring which bears at least one carboxyl group. Benzoic acid occurs naturally in many plants and its name was also derived from a plant source i.e. Gum benzoin. Although it is used as precursor to plasticizers, preservatives such as sodium benzoate, it also has wide application in many pharmaceutical preparations meant for treatment of fungal skin diseases, topical antiseptics, expectorants, analgesics and decongestants. The benzoic acid derivatives are also very useful due to their bacteriostatic and fragrant properties. MTA is used as intermediate in various chemical reactions, MTA is used as a chemical intermediate in manufacturing of insect repellent and plastic stabilizer in the chemical industry. It is also used in the production of various chemicals like 3-carboxybenzaldehyde, 3-benzoylphenylacetic acid, 3-methylbenzophenone, and N,N-diethyl- 3-methylbenzamide etc.. It is a main component of N,N-diethylm-toluamide, commonly known as DEET, which is first insect repellent that can be applied to skin or clothing and provide protection against mosquitoes and other biting insects.
• Uses: m-Toluic acid is used as a reagent in the preparation of hybrid molecules containing oxadiazole and thiadiazole bearing Schiff base moiety as it has antitumor activities. Organic synthesis, to form N,N-diethyl-mtoluamide, a broad-spectrum insect repellent.

Technology Process of M-Toluic acid

There total 270 articles about M-Toluic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

m-xylene (108-38-3,104809-90-7) → isophthalic acid (121-91-5) + m-formylphenyl benzoic acid (619-21-6) + m-Toluic acid (99-04-7)

Guidance literature:

With dihydrogen peroxide; In dimethyl sulfoxide; at 70 ℃; for 10h; Reagent/catalyst; Overall yield = > 99 %; Catalytic behavior;

DOI:10.1039/c5cc00351b

Reference yield: 81.0%

m-tolyl aldehyde (620-23-5) → 3-methylbenzyl alcohol (587-03-1) + (3'-methylbenzyl) 3-methylbenzoate (17145-12-9) + m-Toluic acid (99-04-7)

Guidance literature:

With aluminum (III) chloride; triethylamine; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1007/s00706-021-02785-9

Reference yield: 60.0%

carbon monoxide (201230-82-2) + 3-Iodotoluene (625-95-6) → 3,3'-dimethyl-biphenyl (612-75-9) + 3,3'-dimethylbenzophenone (2852-68-8) + toluene (108-88-3,15644-74-3,16713-13-6) + m-Toluic acid (99-04-7)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; dicobalt octacarbonyl; iron pentacarbonyl; In water; benzene; at 65 ℃; for 24h;

DOI:10.1016/0022-328X(90)87066-M

upstream raw materials:

dipropargylacetic acid

methyl hydrogen all-trans-6,6'-diapocarotene-6,6'-dioate

ethyl 2-acetyl-2-(prop-2-ynyl)pent-4-ynoate

1-chloro-3-methylbenzene

Downstream raw materials:

3'-Methylpropiophenone

2-methyl-1-(3-methylphenyl)propan-1-one

isophthalic acid

5-methyl-2-nitrobenzoic acid

Refernces

A highly efficient large-scale asymmetric direct intermolecular aldol reaction employing L-prolinamide as a recoverable catalyst

10.1002/adsc.201000355

The research focuses on the development of a highly efficient, large-scale asymmetric direct intermolecular aldol reaction using l-prolinamide as a recoverable catalyst. The purpose of this study was to create a simple, bifunctional, recoverable, and reusable organocatalyst that promotes aldol reactions with a high level of enantioselectivity. The catalyst was effective with a wide range of aromatic and heteroaromatic aldehydes with cyclic and acyclic ketones, yielding anti-aldol products with up to 99:1 anti/syn ratio and 98% ee. The catalyst could be easily recovered and reused with only a slight decrease in enantioselectivity over five cycles. The study concluded that l-prolinamide 1b is a robust and effective catalyst for highly enantioselective aldol reactions, and its application can be scaled up while maintaining the same level of enantioselectivity, offering significant potential for industrial applications. Key chemicals used in the process include l-prolinamide derivatives as catalysts, 3-methylbenzoic acid as a cocatalyst, and various aldehydes and ketones as substrates.