(R)-2-Hydroxy-4-phenylbutyric acid

Base Information

• Chemical Name: (R)-2-Hydroxy-4-phenylbutyric acid
• CAS No.: 29678-81-7
• Molecular Formula: C10H12O3
• Molecular Weight: 180.203
• Hs Code.: 2918199090
• European Community (EC) Number: 608-394-1
• UNII: 668UBN3XYA
• DSSTox Substance ID: DTXSID40952135
• Nikkaji Number: J57.297G
• Wikidata: Q72480998
• Mol file: 29678-81-7.mol

Synonyms:(R)-2-hydroxy-4-phenylbutyric acid;2-HPBA;2-hydroxy-4-phenylbutanoate;2-hydroxy-4-phenylbutyrate;2-hydroxy-4-phenylbutyric acid

Chemical Property of (R)-2-Hydroxy-4-phenylbutyric acid

Chemical Property:

• Vapor Pressure: 1.03E-05mmHg at 25°C
• Melting Point: 114-117 °C(lit.)
• Refractive Index: 1.564
• Boiling Point: 356.9 °C at 760 mmHg
• PKA: 3.79±0.10(Predicted)
• Flash Point: 183.9 °C
• PSA: 57.53000
• Density: 1.219 g/cm³
• LogP: 1.06470
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Methanol
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 180.078644241
• Heavy Atom Count: 13
• Complexity: 162

Purity/Quality:

99% ^*data from raw suppliers

(αR)-Hydroxy-benzenebutanoicAcid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCC(C(=O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)CC[C@H](C(=O)O)O
• Uses: (R)-2-Hydroxy-4-phenylbutyric acid is used in the preparation of intermediates of angiotensin converting enzyme inhibitors. Reactant used in the preparation of intermediates of angiotensin converting enzyme inhibitors.

Technology Process of (R)-2-Hydroxy-4-phenylbutyric acid

There total 65 articles about (R)-2-Hydroxy-4-phenylbutyric 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: 99.0%

2-oxo-4-phenylbutyric acid (710-11-2) → (R)-2-hydroxy4-phenylbutanoic acid (29678-81-7,111611-91-7)

Guidance literature:

With formic acid; triethylamine; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine; In methanol; at 20 - 40 ℃; for 3.5h;

Reference yield: 98.1%

(S)-3-methyl-2-phenylbutylammonium (R)-2-hydroxy-4-phenylbutanoate (267013-77-4) → (R)-2-hydroxy4-phenylbutanoic acid (29678-81-7,111611-91-7)

Guidance literature:

With sodium hydroxide; In water;

DOI:10.1021/op010081z

Reference yield: 92.0%

C10H10O3 (128573-54-6) → (R)-2-hydroxy4-phenylbutanoic acid (29678-81-7,111611-91-7)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; at 20 ℃; under 760.051 Torr; Temperature;

upstream raw materials:

R-2-hydroxy-4-phenylbutyric acid L-menthyl ester

(2R,3E)-2-hydroxy-4-phenyl-3-butenenitrile

n-hexanoic anhydride

2-hydroxy-4-phenylbutanoic acid

Downstream raw materials:

(2R)-2-Hydroxy-4-phenylbutyric acid methyl ester

ethyl (R)-2-hydroxy-4-phenylbutyrate

(S)-2-hydroxy-4-phenylbutanoic acid

benzhydryl (2R)-hydroxy-4-phenylbutyrate

Refernces

• 1、 Hirose, Takuji,Kodama, Koichi,Shitara, Hiroaki,Yi, Meng. "Chirality switching in the enantioseparation of 2-hydroxy-4-phenylbutyric acid: Role of solvents in selective crystallization of the diastereomeric salt". . . Retrieved 2020/03/04.
• 2、 Eskici, Mustafa,Karanfil, Abdullah,?zer, M. Sabih,Kabak, Yal??n,Durucasu, ?nci. "Asymmetric synthesis of (S)-dihydrokavain from l-malic acid". . p. 2382 - 2390. Retrieved 2018/10/20.