3-(4-Fluorobenzoyl)propionic acid

HCID 101359
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Basic information

CAS
366-77-8
Standard SMILES
O=C(O)CCC(=O)c1ccc(F)cc1
InChIKey
WUYWHIAAQYQKPP-UHFFFAOYSA-N
Molecular formula
C10H9FO3
Average molar mass
196.17 g/mol
Monoisotopic mass
196.05357237

Overview

4-(4-Fluorophenyl)-4-oxobutanoic acid is an aromatic ketone.

Names & identifiers

Preferred name
3-(4-Fluorobenzoyl)propionic acid
IUPAC
4-(4-fluorophenyl)-4-oxobutanoic acid
English name
3-(4-Fluorobenzoyl)propionic acid
Molecular formula
C10H9FO3
Molecular weight
196.18

Names & synonyms

3-(4-Fluorobenzoyl)propionic acid366-77-8V2Z6N6JC9Zbeta-(4-Fluorobenzoyl)propionic acidDTXSID30190084RefChem:1191604-FBPADTXCID40112575206-679-14-(4-Fluorophenyl)-4-oxobutanoic acid3-(4-Fluorobenzoyl)propanoic acidMFCD00002793
Show more names
R 11302AKOS BBS-00006441LABOTEST-BB LT00233221HALOPERIDOL METABOLITE III4-Fluoro-oxo-benzenebutanoic acid4-Fluoro-γ-oxobenzenebutyric acidβ-(p-Fluorobenzoyl)propionic acid4-(4-fluorophenyl)-4-oxobutanoate
4-(4-Fluorophenyl)-4-oxobutyric acid4-fluorobenzoylpropionic acid4-(4-fluorophenyl)-4-oxo-butanoic acid3-(p-fluorobenzoyl)propionic acid3-(4-Fluorobenzoyl) propionic acidEINECS 206-679-13-(p-Fluorobenzoyl)-propionic acid3-(4-fluorobenzoyl)-propionic acid

Database identifiers

CAS
366-77-8
PubChem CID
101359
DTXSID
DTXSID30190084
ChEMBL
CHEMBL3544869
ChEBI
CHEBI:194800
UNII
V2Z6N6JC9Z
EC Number
206-679-1
Nikkaji
J76.352G

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
54.4 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
4
Heavy atoms
14

Experimental & physicochemical properties

DrugsPharmaceuticals -> Metabolite of Pipamperone

Physicochemical properties

Melting point
100 · 100-102 °C (lit.)
Boiling point
374.4 · 374.4±22.0 °C(Predicted)
Density
1.2441 · 1.2441 (estimate)
storage temp.
Sealed in dry,Room Temperature
solubility
Chloroform (Slightly), Methanol (Slightly)
form
powder to crystal

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (88.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationBenzenebutanoic acid, 4-fluoro-.gamma.-oxo-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 4 (88.9%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
hs_code
29183000
risk_code
36/37/38-20/21/22-22
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Pharmacology

Metabolism/MetabolitesP-Fluorobenzoylpropionic acid and 4-(4-chlorophenyl)-4-hydroxypiperidine is a known human metabolite of haloperidol.
Applications · 2 items

Uses7-Fluoro-1-tetralone was prepared from 3-(4-fluorobenzoyl)-propionic acid by Wolff-Kishner reduction followed by ring closure with polyphosphoric acid and other substituted 1-tetralones where commercially available. Reduction of 3-(4-fluorobenzoyl)propionic acid with an excess of tert-butylamine borane (TBAB) in the presence of AlCl3 provided 4-(4-fluorophenyl)-1-butanol (87) in 63% yield for the synthesis of LM-1507 sodium salt. Penfluridol 1-[4,4-bis(4-fluorophenyl)butyl]-4-(4-chloro-3-trifluoromethylphenyl)- 4-hydroxypiperidine, C 28 H 27 ClF 5 NO, M r 523.99, mp 105 - 107°C, is obtained by reducing the ketone of 3-(4-fluorobenzoyl)propionic acid into a lactone.

General Description3-(4-Fluorobenzoyl)propionic acid is a metabolite of haloperidol, a dopamine D2 receptor blocker.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
北京福源坊科技有限公司010-57903446 15869909019 · [email protected]
毕佳索（上海毕得医药科技股份有限公司）400-6005915 · [email protected]

Additional notes

DefinitionChEBI: 4-(4-Fluorophenyl)-4-oxobutanoic acid is an aromatic ketone.

Related reactions

73 records
New reaction record

Compound notes

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