(S)-2-(4-Methylphenyl)propionic acid

Base Information

• Chemical Name: (S)-2-(4-Methylphenyl)propionic acid
• CAS No.: 124709-72-4
• Molecular Formula: C10H12O2
• Molecular Weight: 164.204
• Hs Code.: 2918300090
• UNII: U2ZQO15R5B
• DSSTox Substance ID: DTXSID501290980
• Nikkaji Number: J608.398F
• Wikidata: Q27290609
• Mol file: 124709-72-4.mol

Synonyms:124709-72-4;(S)-2-(4-Methylphenyl)propionic acid;(S)-2-(4-Methylphenyl)propanoic acid;(2S)-2-(4-methylphenyl)propanoic acid;2-(4-Methylphenyl)propionic acid, (S)-;UNII-U2ZQO15R5B;U2ZQO15R5B;(+)-2-(4-Methylphenyl)propionic acid;Benzeneacetic acid, -alpha-,4-dimethyl-, (-alpha-S)- (9CI);Benzeneacetic acid, alpha,4-dimethyl-, (S)-;Benzeneacetic acid, alpha,4-dimethyl-, (alphaS)-;SCHEMBL597882;(S)-2-(p-Tolyl)propanoic acid;DTXSID501290980;CS-0498831;EN300-717287;Q27290609;BENZENEACETIC ACID, .ALPHA.,4-DIMETHYL-, (S)-;BENZENEACETIC ACID, .ALPHA.,4-DIMETHYL-, (.ALPHA.S)-

Chemical Property of (S)-2-(4-Methylphenyl)propionic acid

Chemical Property:

• PSA: 37.30000
• LogP: 2.18310
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 164.083729621
• Heavy Atom Count: 12
• Complexity: 157

Purity/Quality:

(2S)-2-(4-METHYLPHENYL)PROPANOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(C)C(=O)O
• Isomeric SMILES: CC1=CC=C(C=C1)[C@H](C)C(=O)O

Technology Process of (S)-2-(4-Methylphenyl)propionic acid

There total 24 articles about (S)-2-(4-Methylphenyl)propionic 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: 98.0%

α-(4-methylphenyl)acrylic acid (66616-85-1) → (S)-(+)-2-(4'-methylphenyl)propanoic acid (124709-72-4)

Guidance literature:

With C₄₈H₅₀Cl₄N₂O₂P₂Ru₃; hydrogen; sodium hydrogencarbonate; In methanol; at 20 ℃; for 24h; under 3750.38 Torr; enantioselective reaction; Autoclave;

DOI:10.1021/acs.orglett.6b00748

Reference yield: 93.0%

1-ethenyl-4-methylbenzene (622-97-9,24936-41-2) + carbon monoxide (201230-82-2) → (S)-(+)-2-(4'-methylphenyl)propanoic acid (124709-72-4)

Guidance literature:

With water; hydrogen iodide; C₅₂H₅₂NO₃P; palladium dichloride; In tetrahydrofuran; at 20 ℃; for 72h; under 34202.3 Torr; enantioselective reaction; Autoclave;

DOI:10.1002/anie.202107856

Reference yield: 90.0%

(4R,2'S)-3-[2'-(4-methylphenyl)propionyl]-4-phenyl-oxazolidin-2-one → (4R)-phenyl-2-oxazolidinone (90319-52-1,7480-32-2) + (S)-(+)-2-(4'-methylphenyl)propanoic acid (124709-72-4)

Guidance literature:

(4R,2'S)-3-[2'-(4-methylphenyl)propionyl]-4-phenyl-oxazolidin-2-one; With lithium hydroxide monohydrate; dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃; for 12h; Inert atmosphere;

With hydrogenchloride; In water; pH=3; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.02.021

upstream raw materials:

4-methylisopropylbenzene

2-(4-methylphenyl)propanoic acid ethyl ester

(+/-)-2-(4'-methylphenyl)-propionitrile

(R,S)-2-(4'-methylphenyl) propionic acid

Downstream raw materials:

methyl (S)-2-(4-methylphenyl)propionate

(S,S)-2-(4-methylphenyl)propionic anhydride

Refernces

• 1、 Guan, Zheng-Hui,Ren, Zhi-Hui,Wang, Yuan,Yang, Hui-Yi,Yao, Ya-Hong,Zou, Xian-Jin. "Palladium-Catalyzed Asymmetric Markovnikov Hydroxycarbonylation and Hydroalkoxycarbonylation of Vinyl Arenes: Synthesis of 2-Arylpropanoic Acids". supporting information. p. 23117 - 23122. Retrieved 2021/09/18.
• 2、 Mandrelli, Francesca,Blond, Aurélie,James, Thomas,Kim, Hyejin,List, Benjamin. "Deracemizing α-Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis-Silyl Ketene Acetals with Water or Methanol". supporting information. p. 11479 - 11482. Retrieved 2019/07/18.