4-Phenylbutyric acid

Base Information

• Chemical Name: 4-Phenylbutyric acid
• CAS No.: 1821-12-1
• Molecular Formula: C10H12O2
• Molecular Weight: 164.204
• Hs Code.: 29163900
• European Community (EC) Number: 217-341-8
• NSC Number: 295
• UNII: 7WY7YBI87E
• DSSTox Substance ID: DTXSID2037631
• Nikkaji Number: J101.512E
• Wikidata: Q27088364
• NCI Thesaurus Code: C63699
• RXCUI: 1546447
• Metabolomics Workbench ID: 37302
• ChEMBL ID: CHEMBL1469
• Mol file: 1821-12-1.mol

Synonyms:Butyricacid, 4-phenyl- (8CI);Butyric acid, g-phenyl- (3CI);4-Phenyl-n-butyric acid;Benzenebutanoic acid;Benzenebutyric acid;NSC 295;g-Phenylbutanoic acid;g-Phenylbutyric acid;w-Phenylbutanoic acid;

Chemical Property of 4-Phenylbutyric acid

Chemical Property:

• Appearance/Colour: white to slightly yellowish crystalline powder
• Vapor Pressure: 0.000934mmHg at 25°C
• Melting Point: 49-51 °C(lit.)
• Refractive Index: 1.534
• Boiling Point: 290.7 °C at 760 mmHg
• PKA: 4.76(at 25℃)
• Flash Point: 187.9 °C
• PSA: 37.30000
• Density: 1.095 g/cm³
• LogP: 2.09390
• Storage Temp.: Store below +30°C.
• Solubility.: 5.3g/l
• Water Solubility.: 5.3 g/L at 40 ºC
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 164.083729621
• Heavy Atom Count: 12
• Complexity: 137

Purity/Quality:

99% ^*data from raw suppliers

4-Phenylbutyric Acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Drug Classes: Urea Cycle Disorder Agents
• Canonical SMILES: C1=CC=C(C=C1)CCCC(=O)O
• Recent ClinicalTrials: PBA Use for Treatment of ATF6-/- Patients
• Recent EU Clinical Trials: A Phase IIIb, Open Label Extension Study Evaluating The Safety And Tolerability of AMX0035 Up To 108 Weeks In Adult Participants with Amyotrophic Lateral Sclerosis (ALS) Previously Enrolled In Study A35-004 (PHOENIX)
• Uses: 4-Phenylbutyric acid is used as a chemical chaperone involved in protein-folding disorders. It is involved in the synthesis of dyes and an active pharmaceutical ingredient intermediate.

Technology Process of 4-Phenylbutyric acid

There total 195 articles about 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: 95.0%

succinylbenzene (2051-95-8) → 4-Phenylbutyric acid (1821-12-1)

Guidance literature:

succinylbenzene; With hydrazine hydrate; In diethylene glycol; at 25 ℃; for 0.5h;

With potassium hydroxide; In diethylene glycol; at 120 - 245 ℃; for 4.5h;

DOI:10.1039/c8ob00227d

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + hydrocinnamic acid chloride (645-45-4) → 4-Phenylbutyric acid (1821-12-1)

Guidance literature:

With diethyl ether; Eintragen einer Loesung des erhaltenen Diazoketons in Dioxan in eine Suspension von Silberoxid in wss. Natriumthiosulfat-Loesung bei 70grad;

DOI:10.1039/jr9380001997

Reference yield:

pyridine (110-86-1) + bromo-phenethyl-malonic acid (959055-65-3) → 4-Phenylbutyric acid (1821-12-1)

Guidance literature:

at 160 - 180 ℃;

upstream raw materials:

Acetic acid 1-cyano-4-phenyl-1-(pyridin-2-ylsulfanyl)-butyl ester

Trifluoro-acetic acid 1-cyano-4-phenyl-1-(pyridin-2-ylsulfanyl)-butyl ester

1,3-dimethyl-2-(3-phenylpropyl)-1H-imidazolium iodide

7-phenylheptane-1,2,3,4-tetraol

Downstream raw materials:

2-(3-phenyl-propyl)-5,6-dihydro-4H-[1,3]thiazine

5-Chloro-N-(2-diethylamino-ethyl)-2-methoxy-4-(4-phenyl-butyrylamino)-benzamide

(+/-)-2-<4-Phenyl-butanoxy>-buttersaeure

5-phenyl-2-pentanone

Refernces

• 1、 Truce,Olson. "-". . p. 4721. Retrieved 1952.
• 2、 Yang, Heng-Pan,Lin, Qing,Zhang, Han-Wen,Li, Guo-Dong,Fan, Liang-Dong,Chai, Xiao-Yan,Zhang, Qian-Ling,Liu, Jian-Hong,He, Chuan-Xin. "Platinum/nitrogen-doped carbon/carbon cloth: A bifunctional catalyst for the electrochemical reduction and carboxylation of CO2 with excellent efficiency". . p. 4108 - 4111. Retrieved 2018.
• 3、 Asinger et al.. "-". . p. 825. Retrieved 1967.
• 4、 Pfennig, Victoria S.,Villella, Romina C.,Nikodemus, Julia,Bolm, Carsten. "Mechanochemical Grignard Reactions with Gaseous CO2 and Sodium Methyl Carbonate**". supporting information. . Retrieved 2022/01/22.
• 5、 Corbin, Nathan,Lazouski, Nikifar,Manthiram, Karthish,Steinberg, Katherine,Yang, Deng-Tao. "Suppressing carboxylate nucleophilicity with inorganic salts enables selective electrocarboxylation without sacrificial anodes". . p. 12365 - 12376. Retrieved 2021/10/08.