CAS 619-66-9 4-Formylbenzoic acid (HCID 12088)

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Basic information

CAS: 619-66-9
Standard SMILES: O=Cc1ccc(C(=O)O)cc1
InChIKey: GOUHYARYYWKXHS-UHFFFAOYSA-N
Molecular formula: C8H6O3
Average molar mass: 150.13 g/mol
Monoisotopic mass: 150.03169405

Overview

4-formylbenzoic acid is a member of the class of benzoic acids that is benzoic acid substituted by a formyl group at position 4. It has a role as a plant metabolite. It is a member of benzaldehydes, a member of benzoic acids and a monocarboxylic acid. It is a conjugate acid of a 4-formylbenzoate.

Names & identifiers

Preferred name: 4-Formylbenzoic acid
IUPAC: 4-formylbenzoic acid
English name: 4-Formylbenzoic acid
Molecular formula: C8H6O3
Molecular weight: 150.13

Names & synonyms

4-FORMYLBENZOIC ACID4-Carboxybenzaldehyde619-66-9Terephthalaldehydic acidBenzoic acid, 4-formyl-p-Formylbenzoic acidp-CarboxybenzaldehydeTerephthaldehydic acidpara-carboxybenzaldehydeDTXSID3027249p-benzoic acid aldehydeUES4QRK36E

Show more names

4-Formylbenzoic acid Vetec(TM) reagent grade, 97%4-FormyLCarboxybenzaldehydeNSC 15797AKOS BBS-00003246ForMylbenzoic aci

NSC-15797TEREPHTHALALDEHYDE ACIDCHEBI:191179RefChem:1113398210-607-4MFCD000069514-Formyl-benzoic acidHSDB 5719

Database identifiers

CAS: 619-66-9
PubChem CID: 12088
DTXSID: DTXSID3027249
ChEMBL: CHEMBL113897
ChEBI: CHEBI:191179
UNII: UES4QRK36E

Properties

Computed structural properties

XLogP: 1.8
Topological polar surface area: 54.4 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 11
Formal charge: 0
Complexity: 157

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Benzoic Acid Derivatives

SolubilitySLIGHTLY SOLUBLE IN HOT WATER; VERY SOLUBLE IN ALCOHOL; SOLUBLE IN ETHER AND IN CHOLROFORM

Boiling PointSUBLIMES BEFORE REACHING BOILING POINT

Melting Point256 °C

Vapor Pressure0.000375 [mmHg]

Physical DescriptionWhite powder; [MSDSonline]

Physicochemical properties

Melting point: 247 °C · 247 °C(lit.)
Boiling point: 231.65 °C · 231.65°C (rough estimate)
Density: 1.2645 · 1.2645 (rough estimate)
bulk density: 396 kg/m3 · 396kg/m3
refractive index: 1.45 · 1.4500 (estimate)
storage temp.

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): 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 54 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 20-01-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/18952

Benzoic acid, 4-formyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryAn irritant; [MSDSonline]

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Toxicology

Non-Human Toxicity Excerpts · 1 item

INTERACTIONS OF P-CARBOXYBENZALDEHYDE WITH RAT LIVER MITOCHONDRIA WAS EXAMINED IN VITRO. ALTHOUGH PYRUVATE/MALEATE- & SUCCINATE-MEDIATED RESPIRATION, AS WELL AS THAT MEDIATED BY OTHER CITRIC ACID CYCLE INTERMEDIATES, WERE INHIBITED, CYTOCHROME C OXIDASE WAS NOT INHIBITED.

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
rtecs: WZ0440000
hs_code: 29183000

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationBenzoic acid, 4-formyl-: ACTIVE

Applications · 4 items

Description4-Formylbenzoic acid, also known as 4-Carboxybenzaldehyde, is a white crystalline powder with a molecular formula of C8H5O3. It is insoluble in water but can be dissolved in DMF. This compound has the ability to undergo esterification reactions and alcohol-aldehyde condensation reactions with alcohols. 4-Formylbenzoic acid is a metabolite of aldehydes. It is an important intermediate for organic synthesis, widely used in medicine, pesticides, coatings, liquid crystal raw materials, polymer materials and perfume raw materials.

Uses4-Carboxybenzaldehyde is an important intermediate in the synthesis of terepthalic acid. It has been used as reagent during esterification of 2,2,6,6-tetramethyl-4-oxopiperidinyl-1-oxyl to yield 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl 4-formylbenzoate.

Uses4-Formylbenzoic acid is usually used as reagent during esterification of 2,2,6,6-tetramethyl-4-oxopiperidinyl-1-oxyl to yield 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl 4-formylbenzoate.

General Description4-Formylbenzoic acid is an important intermediate in the synthesis of terepthalic acid. It reacts with barium carbonate to yield two-dimensional barium(II) coordination polymer.