CAS 42019-78-3 4-Hydroxy-4'-chlorobenzophenone (HCID 123504)

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Basic information

CAS: 42019-78-3
Standard SMILES: O=C(c1ccc(O)cc1)c1ccc(Cl)cc1
InChIKey: RUETVLNXAGWCDS-UHFFFAOYSA-N
Molecular formula: C13H9ClO2
Average molar mass: 232.66 g/mol
Monoisotopic mass: 232.02910721

Names & identifiers

Preferred name: 4-Hydroxy-4'-chlorobenzophenone
IUPAC: (4-chlorophenyl)-(4-hydroxyphenyl)methanone
English name: 4-Chloro-4'-hydroxybenzophenone
Molecular formula: C13H9ClO2
Molecular weight: 232.66

Names & synonyms

4-Chloro-4'-hydroxybenzophenone42019-78-3(4-Chlorophenyl)(4-hydroxyphenyl)methanone4-Hydroxy-4'-chlorobenzophenone4-(4-chlorobenzoyl)phenol4-p-ChlorobenzoylphenolDTXSID4047961Methanone, (4-chlorophenyl)(4-hydroxyphenyl)-FF9YB926A3EINECS 255-627-4DTXCID0027937EC 255-627-4

Show more names

4-CHLORO-4-HYDROXYBENZOPHENONENSC4056NSC 4056NSC-40564-Chloro-4'-4-Chloro-4'EP-A /USP RC A4-Chloro-4'-hydroxyb-hydroxybenzophenone

1-(4-CHLOROPHENYL)-1-(4-HYDROXYPHENYL)METHANONERefChem:523858BENZOPHENONE, 4-CHLORO-4'-HYDROXY-BENZOPHENONE, 4-CHLORO-4'-HYDROXY-(6CI)255-627-4(4-chlorophenyl)-(4-hydroxyphenyl)methanoneMFCD00002357CBMicro_020566

Database identifiers

CAS: 42019-78-3
PubChem CID: 123504
DTXSID: DTXSID4047961
ChEMBL: CHEMBL1438628

Properties

Computed structural properties

XLogP: 3.7
Topological polar surface area: 37.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 2
Heavy atoms: 16
Formal charge: 0
Complexity: 238

Experimental & physicochemical properties

LogP4.0

Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point: 177 · 177-181 °C
Boiling point: 257 °C · 257 °C (13 mmHg)
Density: 1.2082 · 1.2082 (rough estimate)
refractive index: 1.5434 · 1.5434 (estimate)
Flash point: 100 °C · 100 °C
storage temp.: Inert atmosphere,Room Temperature
solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
pka: 7.68 · 7.68±0.15(Predicted)
form: solid
color: Pale Beige to Light Brown
BRN: 2049956 · 2049956
Major Application: pharmaceutical small molecule

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 5.3% (3 of 57) of reports.

Warning

H315 (93%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Aggregated GHS information provided per 57 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 23-02-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17952

Hazard Classes and CategoriesSkin Irrit. 2 (93%)

Safety data

wgk: WGK 3
hs_code: 29144000
risk_code: 36/37/38-20/21/22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi,Xn
hazard_note: Irritant
safety_code: 24/25-37/39-26-36
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
REACH Registrations: Active
Precautionary statements: P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P305+P351+P338-P261-P280a-P304+P340-P405-P501a

Chemistry & industry

Applications · 1 item

Uses4-Chloro-4’-hydroxybenzophenone (Fenofibrate EP Impurity A; Fenofibrate USP Related Compound A) the impurity of Fenofibric acid (42017-89-0), the active metabolite of fenofibrate which increases Apolipoprotein A-I–Mediated High-Density Lipoprotein Biogenesis by enhancing transcription of ATP-Binding cassette transporter A1 gene in a liver X receptor–dependent manner.

Preparation methods · 1 item

PreparationPreparation by Fries rearrangement of phenyl p-chloro-benzoate, in the presence of aluminium chloride, without solvent, at 160° for 5 min, between 120° and 160° (good yield) or at 130° for 1 h, then at 160° for 1 h (10%) or in refluxing chlorobenzene for 10 h (52%); in the presence of trifluoromethanesulfonic acid at 45–55° (94%).