7335-63-9

Basic information

• Product Name: 3-methoxy-3-phenyl-2-benzofuran-1(3H)-one
• Synonyms: 3-Methoxy-3-phenyl-3H-isobenzofuran-1-one
• CAS NO: 7335-63-9
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.254
• Mol File: 7335-63-9.mol

Chemical Properties

• Boiling Point: 405.2°C at 760 mmHg
• Flash Point: 171.6°C
• Density: 1.26g/cm³
• Vapor Pressure: 8.91E-07mmHg at 25°C
• Refractive Index: 1.62
• CAS DataBase Reference: 3-methoxy-3-phenyl-2-benzofuran-1(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methoxy-3-phenyl-2-benzofuran-1(3H)-one(7335-63-9)
• EPA Substance Registry System: 3-methoxy-3-phenyl-2-benzofuran-1(3H)-one(7335-63-9)

Safety Data

• Hazardous Substances Data: 7335-63-9(Hazardous Substances Data)

Usage

General Description

3-Methoxy-3-phenyl-2-benzofuran-1(3H)-one, also known as apiole, is a naturally occurring organic compound with a chemical structure consisting of a benzofuran ring with a phenyl group and a methoxy group attached. It is commonly found in plants such as parsley and dill, and has been used in traditional medicine for its sedative and anticonvulsant properties. Apiole has also been investigated for its potential as an insecticide and as a precursor for the synthesis of other compounds with medicinal or pharmacological applications. However,

Upstream product

• 67-56-1 methanol 
• 85-52-9 2-Benzoylbenzoic acid 
• 18852-53-4 3-chloro-3-phenylphthalide 

Downstream Products

• 606-28-0 methyl o-benzoylbenzoate 
• 7500-78-9 o-benzoylbenzamide 
• 84-65-1 9,10-phenanthrenequinone 

Relevant articles and documents

Pseudoacids. II. 2-Acylbenzoic Acid Derivatives

Structures of derivatives of cyclic o-acylbenzoic acids, including the chloride, endo- and exocyclic amides, esters and anhydrides, are examined. 3-Chloro-1(3H)-isobenzofuranone (1), orthorhombic, Pbca, a = 11.616 (5), b = 8.120 (3), c = 15.640 (9) A; 3-methoxy-3-phenyl-1(3H)-isobenzofuranone (3), orthorhombic, P212121, a = 6.923 (2), b = 8.291 (4), c = 21.551 (8) A; 3-hydroxy-3-phenyl-N-propyl-1(3H)-isoindolone (4), orthorhombic, P212121, a = 8.662 (4), b = 9.551 (7), c = 17.649 (14) A; 3-(N-morpholino)-1(3H)-isobenzofuranone (5), triclinic, P1, a = 6.172 (4), b = 11.163 (7), c = 17.33 (2) A, α = 105.91 (6), β = 99.85 (6), γ = 97.57 (5)°; 3-(2′-benzoylbenzoyloxy)-3-phenyl-1(3H)-isobenzofuranone (7), triclinic, P1, a = 9.694 (3), b = 10.505 (4), c = 11.163 (4) A°, α = 80.58 (3), β = 80.41 (3), γ = 76.49 (3)°; bis[1(3H)-isobenzofuranone-3-yl]ether (8), monoclinic, I2/a, a = 15.31 (2), b = 6.111 (12), c = 28.30 (5) A, β = 101.61 (12)°. An open oxoacid tertiary amide is also described: N-morpholino 2′-benzoylbenzamide (6): monoclinic, P21/c, a = 6.844 (4), b = 15.696 (8), c = 14.154 (7) A, β = 99.43 (4)°. Pseudoacid derivatives form planar isobenzofuran and isoindole rings, and the former aldehyde/ketone carbon-heteroatom endocyclic and exocyclic bond distances show bond length variations which correlate with the relative basicities of the attached groups. Structures of both endocyclic and exocyclic nitrogen pseudoamides are reported as well as examples of the normal-pseudoanhydride and the dipseudoanhydride.

Aspects of Tautomerism: Part 14 - Alcoholysis of A-ring Substituted ortho-Benzoylbenzoyl Chlorides: Evidence for Solvent Involvement in Determining Nature of Transition State.

Rates of alcoholysis of A-ring substituted o-benzoylbenzoic acid chlorides with 10percent methanol, 10percent ethanol, 50percent isopropanol and 50percent cyclohexanol in acetone medium have been measured.The Hammett ρ-values range from -2.2 to -0.76.These results have been interpreted as evidence for transition states which vary gradually in their degree of charge separation and have features of both SN1 and SN2 reactions.