Coumaranone

HCID 23556

Notes Reactions

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Basic information

CAS: 7169-34-8
Standard SMILES: O=C1COc2ccccc21
InChIKey: MGKPCLNUSDGXGT-UHFFFAOYSA-N
Molecular formula: C8H6O2
Average molar mass: 134.13 g/mol
Monoisotopic mass: 134.03677943

Names & identifiers

Preferred name: Coumaranone
IUPAC: 1-benzofuran-3-one
English name: 3-Coumaranone
Molecular formula: C8H6O2
Molecular weight: 134.13

Names & synonyms

Benzofuran-3(2H)-one7169-34-83(2H)-BENZOFURANONECoumaranone1-Benzofuran-3(2H)-oneBenzofuran-3-one1-benzofuran-3-one2,3-dihydro-1-benzofuran-3-oneKZ7LS8K9LPCCRIS 3596NSC-512726DTXSID20221917

Show more names

3-Oxocoumaran3-Coumaranone,97%

NSC 512726RefChem:579298DTXCID50144408640-279-13-CoumaranoneCoumaran-3-one2H-BEZOFURAN-3-ONE2,3-Dihydrobenzo[b]furan-3-one

Database identifiers

CAS: 7169-34-8
PubChem CID: 23556
DTXSID: DTXSID20221917
ChEMBL: CHEMBL2253270
UNII: KZ7LS8K9LP
EC Number: 640-279-1
Nikkaji: J20.648B

Properties

Computed structural properties

XLogP: 1.5
Topological polar surface area: 26.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 0
Heavy atoms: 10
Formal charge: 0
Complexity: 153

Physicochemical properties

Melting point: 101 · 101-103 °C
Boiling point: 207.23 °C · 207.23°C (rough estimate)
Density: 1.1603 · 1.1603 (rough estimate)
refractive index: 1.48 · 1.4800 (estimate)
storage temp.: -20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility: Chloroform (Slightly), DMSO (Slightly)
form: Solid
pka: 8.66 · 8.66
color: Yellow to Dark Yellow
Water Solubility: Slightly miscible with water.
Sensitive: Light Sensitive
BRN: 115296 · 115296
InChI: InChI=1S/C8H6O2/c9-7-5-10-8-4-2-1-3-6(7)8/h1-4H,5H2
InChIKey: MGKPCLNUSDGXGT-UHFFFAOYSA-N
SMILES: O1C2=CC=CC=C2C(=O)C1
CAS DataBase Reference: 7169 · 7169-34-8(CAS DataBase Reference)
FDA UNII: 7 LS8K9LP · KZ7LS8K9LP
NIST Chemistry Reference: 3 · 3(2H)-benzofuranone(7169-34-8)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H332-H335
Precautionary statements: 261 · P261-P280-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi,Xn
Risk Statements: 36 · 36/37/38-20/21/22
Safety Statements: 22 · 22-24/25-36/37/39-26-36
WGK Germany: 3 · 3
F: 4.5 · 4.5-9
Hazard Note: Irritant
HS Code: 29329990 · 29329990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

F: 4.5-9
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29329990
risk_code: 36/37/38-20/21/22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi,Xn
hazard_note: Irritant
safety_code: 22-24/25-36/37/39-26-36
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H332-H335
Precautionary statements: P261-P280-P305+P351+P338

Chemistry & industry

Applications · 2 items

Uses3-Coumaranone is used in the aurones, [2-benzylidenebenzofuran-3(2H)-ones] by reacting with appropriate aldehyde. It is involved in the condensation reaction with aldehydes in the presence of morpholine acetate to prepare substituted 2-(arylidene)benzofuran-3(ZH)-ones. In Horner-Wadsworth-Emmons reaction, it reacts with diethyl cyanomethylphosphonate to give 3-(cyanomethyl)benzofurans, which is an intermediate in the synthesis of antihyperglycemic agents.

General DescriptionBenzofuran-3(2H)-one undergoes condensation with aldehydes in the presence of morpholine acetate to yield substituted 2-(arylidene)benzofuran-3(ZH)-ones. It undergoes acid- or base-catalyzed condensation with an appropriate aldehyde to yield aurones [2-benzylidenebenzofuran-3(2H)-ones].