Mesitylacetic acid

Base Information

• Chemical Name: Mesitylacetic acid
• CAS No.: 4408-60-0
• Molecular Formula: C11H14O2
• Molecular Weight: 178.231
• Hs Code.: 29163990
• European Community (EC) Number: 224-556-0
• NSC Number: 11348
• UNII: 3D4D9H5LJW
• DSSTox Substance ID: DTXSID40196032
• Nikkaji Number: J205.788C
• Wikidata: Q72514239
• Mol file: 4408-60-0.mol

Synonyms:Mesitylacetic acid;4408-60-0;2-Mesitylacetic acid;2,4,6-Trimethylphenylacetic acid;2-(2,4,6-trimethylphenyl)acetic acid;(2,4,6-Trimethylphenyl)acetic acid;Benzeneacetic acid, 2,4,6-trimethyl-;2,4,6-Trimethylbenzeneacetic Acid;Mesityleneacetic Acid;2-Mesityleneacetic acid;3D4D9H5LJW;2,4,6-Trimethulphenylacetic acid;EINECS 224-556-0;MFCD00014368;NSC-11348;(2,4,6-Trimethyl-phenyl)-acetic acid;Mesitylessigsaure;Mesityl acetic acid;Mesityl-acetic acid;Mesitylacetic acid, 97%;UNII-3D4D9H5LJW;SCHEMBL509440;2,4,6-Trimethyl-a-toluic acid;DTXSID40196032;NSC11348;STR05126;NSC 11348;STK114884;AKOS001476152;CS-W017323;NCGC00336955-01;AC-23598;BP-12803;SY014079;TS-02482;AM20060777;BB 0248969;FT-0604577;M1218;EN300-125462;AB01330109-02;A826483;J-507087

Chemical Property of Mesitylacetic acid

Chemical Property:

• Vapor Pressure: 0.000219mmHg at 25°C
• Melting Point: 167-171 °C(lit.)
• Refractive Index: 1.5090 (estimate)
• Boiling Point: 312.886 °C at 760 mmHg
• PKA: 4.40±0.10(Predicted)
• Flash Point: 209.967 °C
• PSA: 37.30000
• Density: 1.076 g/cm³
• LogP: 2.23890
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 177

Purity/Quality:

98%,99%, ^*data from raw suppliers

Mesitylacetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37-26

MSDS Files:

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC1=CC(=C(C(=C1)C)CC(=O)O)C
• Uses: Mesitylacetic acid may be used to synthesize 2,4,6-trimethvlbenzyl mesitylacetate.

Technology Process of Mesitylacetic acid

There total 38 articles about Mesitylacetic 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: 91.0%

2-ethynyl-1,3,5-trimethylbenzene (769-26-6) → 2-mesitylacetic acid (4408-60-0)

Guidance literature:

2-ethynyl-1,3,5-trimethylbenzene; With 1-methyl-pyrrolidin-2-one; C₁₇H₁₁ClF₆N₂Ru⁽¹⁺⁾; In water; at 25 ℃; for 24h; Inert atmosphere;

With [bis(acetoxy)iodo]benzene; at 25 ℃; for 1h;

DOI:10.1021/acs.joc.5b01220

Reference yield: 82.0%

carbon monoxide (201230-82-2) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → 2-mesitylacetic acid (4408-60-0)

Guidance literature:

carbon monoxide; With C₂₈H₂₂CoN₄O₆; In butan-1-ol; at 60 ℃; for 2h; under 760.051 Torr; Glovebox; High pressure; Green chemistry;

2-chloromethyl-1,3,5-trimethylbenzene; With tetra-(n-butyl)ammonium iodide; sodium hydroxide; In butan-1-ol; at 60 ℃; for 22h; under 760.051 Torr; regioselective reaction; Glovebox; High pressure; Green chemistry;

DOI:10.1016/j.tet.2013.06.083

Reference yield: 76.0%

C13H15Cl3O2 (1255911-42-2) → 2,4,6-trimethylphenylacetic acid 2-deuterio-2,2-dichloroethyl ester (1255911-53-5) + 2-mesitylacetic acid (4408-60-0)

Guidance literature:

With indium; deuterated ammonium chloride; In tetrahydrofuran-d8; water-d2; at 20 ℃; for 40h; chemoselective reaction; Reflux;

DOI:10.1016/j.tetlet.2010.09.039

upstream raw materials:

mesitylacetonitrile

2,4,6-Trimethylacetophenone

2,4,6-trimethylmandelic acid

mesitylglyoxylic acid

Downstream raw materials:

N-Hydroxy-N-methyl-2-(2,4,6-trimethyl-phenyl)-acetamide

3-(Dimethylamino)-2-(2,4,6-trimethylphenyl)propenal

Dimethyl-[(E)-2-(2,4,6-trimethyl-phenyl)-vinyl]-amine

4-[(E)-2-(2,4,6-Trimethyl-phenyl)-vinyl]-morpholine

Refernces

• 1、 Bazzi, Sakna,Schulz, Emmanuelle,Mellah, Mohamed. "Electrogenerated Sm(II)-Catalyzed CO2 Activation for Carboxylation of Benzyl Halides". supporting information. p. 10033 - 10037. Retrieved 2019/12/24.
• 2、 -. "A 2, 4, 6-Trimethylbenzene acetyl chloride synthesis process". Paragraph 0065. . Retrieved 2017/02/09.