(S)-3-Hydroxy-3-phenylpropionic acid

Base Information

• Chemical Name: (S)-3-Hydroxy-3-phenylpropionic acid
• CAS No.: 36567-72-3
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 29181998
• European Community (EC) Number: 623-755-3
• DSSTox Substance ID: DTXSID101289084
• Nikkaji Number: J61.917E
• Wikidata: Q27122298
• Metabolomics Workbench ID: 57616
• Mol file: 36567-72-3.mol

Synonyms:36567-72-3;(S)-3-HYDROXY-3-PHENYLPROPANOIC ACID;(S)-3-Hydroxy-3-phenylpropionic acid;(3S)-3-hydroxy-3-phenylpropanoic acid;(S)-(-)-3-Hydroxy-3-phenylpropionic acid;MFCD00145262;SCHEMBL904490;(?)-3-Phenylhydracrylic acid;CHEBI:51058;AYOLELPCNDVZKZ-QMMMGPOBSA-N;DTXSID101289084;AKOS015894011;AS-62947;CS-0225208;EN300-123114;Q27122298;(S)-3-Hydroxy-3-phenylpropionic acid, >=98.0% (sum of enantiomers, GC)

Chemical Property of (S)-3-Hydroxy-3-phenylpropionic acid

Chemical Property:

• Appearance/Colour: White to almost white needle-like crystals
• Vapor Pressure: 7.14E-05mmHg at 25°C
• Melting Point: 117-120 °C
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 329.4 °C at 760 mmHg
• Flash Point: 167.2 °C
• PSA: 57.53000
• Density: 1.262 g/cm³
• LogP: 1.19470
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 166.062994177
• Heavy Atom Count: 12
• Complexity: 150

Purity/Quality:

99% ^*data from raw suppliers

(S)-(-)-3-Hydroxy-3-phenylpropionic acid, 98+% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

Technology Process of (S)-3-Hydroxy-3-phenylpropionic acid

There total 88 articles about (S)-3-Hydroxy-3-phenylpropionic 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: 95.0%

(S)-3-[(S)-3-hydroxy-3-phenylpropanoyl]-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one (1375257-32-1) → (S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one (1375257-29-6) + (S)-3-hydroxy-3-phenylpropanoic acid (36567-72-3,40620-59-5)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; for 2h; Reflux;

DOI:10.1021/ol300949s

Reference yield: 95.0%

(S)-3-(3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoyl)oxazolidin-2-one (1407186-17-7) → (S)-3-hydroxy-3-phenylpropanoic acid (36567-72-3,40620-59-5)

Guidance literature:

With lithium hydroxide monohydrate; dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃; for 6h;

DOI:10.1021/ol302839d

Reference yield: 93.0%

(S)-3-hydroxy-3-phenylpropanenitrile (132203-26-0) → (S)-3-hydroxy-3-phenylpropanoic acid (36567-72-3,40620-59-5)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; at 70 - 90 ℃;

DOI:10.1002/1615-4169(200210)344:9<947::AID-ADSC947>3.0.CO;2-Z

upstream raw materials:

brucine

3-hydroxy-3-phenylpropanoic acid

pyridine

3-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)-3-oxopropanoic acid

Downstream raw materials:

methyl (S)-3-hydroxy-3-phenylpropionate

3-bromo-3-phenylpropionic acid

3-hydroxy-3-phenylpropionamide

3-chloro-3-phenylpropanoic acid

Refernces

• 1、 Kodama, Koichi,Nagata, Jun,Kurozumi, Nobuhiro,Shitara, Hiroaki,Hirose, Takuji. "Solvent-induced chirality switching in the enantioseparation of regioisomeric hydroxyphenylpropionic acids via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol". . p. 460 - 466. Retrieved 2017/03/23.
• 2、 Lorente, Adriana,Pellicena, Miquel,Romea, Pedro,Urpí, Fèlix. "Stereoselective acetate aldol reactions of α-silyloxy ketones". . p. 1023 - 1035. Retrieved 2015/01/30.