(S)-3-Phenylbutyric acid

Base Information

• Chemical Name: (S)-3-Phenylbutyric acid
• CAS No.: 772-15-6
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.204
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID60357380
• Nikkaji Number: J70.852F
• Wikidata: Q27460225
• Mol file: 772-15-6.mol

Synonyms:(S)-3-Phenylbutyric acid;772-15-6;(3S)-3-phenylbutanoic acid;(S)-3-Phenylbutanoic acid;3-Phenylbutanoic acid #;MFCD00077842;(S)-3-Phenylbutanoicacid;SCHEMBL1149768;(S)-3-PHENYLBUTYRICACID;DTXSID60357380;(S)-beta-Methylhydrocinnamic acid;AC6792;AKOS015840314;AKOS015890816;AS-58165;CS-0106072;Benzenepropanoic acid, .beta.-methyl-, (S)-;EN300-108269;A914434;Q27460225;(S)-3-Phenylbutyric acid, >=99.0% (sum of enantiomers, HPLC)

Chemical Property of (S)-3-Phenylbutyric acid

Chemical Property:

• Refractive Index: n20/D 1.518
• Boiling Point: 94-95 °C0.3 mm Hg(lit.)
• PKA: 4.67±0.10(Predicted)
• PSA: 37.30000
• Density: 1.069 g/mL at 20 °C(lit.)
• LogP: 2.26480
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 164.083729621
• Heavy Atom Count: 12
• Complexity: 148

Purity/Quality:

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

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CC(=O)O)C1=CC=CC=C1
• Isomeric SMILES: C[C@@H](CC(=O)O)C1=CC=CC=C1
• Uses: (S)-3-Phenylbutyric Acid is used as a sole carbon and energy source in the isolation of Rhodococcus rhodochrous PB1 from compost soil.Also, it is used in the design and synthesis of 2-Acylaminopyridin-4-ylimidazoles as p38 MAP kinase inhibitors in the treatment of many inflammatory disorders.

Technology Process of (S)-3-Phenylbutyric acid

There total 83 articles about (S)-3-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: 98.0%

(E)-3-phenyl-2-butenoic acid (704-80-3) → (S)-2-phenylbutanoic acid (4593-90-2,772-15-6)

Guidance literature:

With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R,R)-f-spiroPhos; hydrogen; In dichloromethane; at -15 - 20 ℃; for 6h; under 7600.51 Torr; Solvent; enantioselective reaction; Autoclave;

DOI:10.1021/acs.joc.6b00018

Reference yield: 97.0%

(S)-N-((1R,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-3-phenyl-butyramide (88563-99-9) → (S)-2-phenylbutanoic acid (4593-90-2,772-15-6)

Guidance literature:

With sulfuric acid; In acetic acid;

DOI:10.1021/jo00177a047

Reference yield: 91.0%

N-benzyl-N-methyl-3-phenylbutanamide → (S)-2-phenylbutanoic acid (4593-90-2,772-15-6)

Guidance literature:

With sulfuric acid; acetic acid; In water; at 150 ℃; for 21h; Inert atmosphere; Sealed tube; Schlenk technique;

DOI:10.1021/acs.orglett.0c02064

upstream raw materials:

dibutyl ether

(-)-O-(3-Phenyl-cis-crotonoyl)-menthol

3-phenylbutyric acid

(S)-1-phenyl-ethylamine

Downstream raw materials:

(R)-(-)-3-phenylbutyric acid methyl ester

C₁₅H₂₀O₃

(S)-3-phenyl butyric acid chloride

C₁₅H₂₀O₃

Refernces

• 1、 Link, Achim,Zhou, Yujing,Buchwald, Stephen L.. "CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids". . p. 5666 - 5670. Retrieved 2020/07/24.
• 2、 Drienovská, Ivana,Gajdo?, Matú?,Kindler, Alexia,Takhtehchian, Mahsa,Darnhofer, Barbara,Birner-Gruenberger, Ruth,D?rr, Mark,Bornscheuer, Uwe T.,Kourist, Robert. "Folding Assessment of Incorporation of Noncanonical Amino Acids Facilitates Expansion of Functional-Group Diversity for Enzyme Engineering". supporting information. p. 12338 - 12342. Retrieved 2020/09/07.