1689-09-4

Basic information

• Product Name: 3,3-dimethylphthalide
• Synonyms: 3,3-dimethylphthalide;3,3-Dimethyl-1,3-dihydroisobenzofuran-1-one;3,3-Dimethyl-2-benzofuran-1(3H)-one;3,3-dimethyl-1(3H)-Isobenzofuranone;1(3H)-Isobenzofuranone, 3,3-dimethyl-;3,3-dimethyl-2-benzofuran-1-one
• CAS NO: 1689-09-4
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.1852
• EINECS: 216-878-5
• Mol File: 1689-09-4.mol
• Article Data: 32

Chemical Properties

• Melting Point: 69-70℃
• Boiling Point: 291.1°Cat760mmHg
• Flash Point: 117.8°C
• Appearance: /
• Density: 1.122g/cm³
• Vapor Pressure: 0.00199mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: 3,3-dimethylphthalide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-dimethylphthalide(1689-09-4)
• EPA Substance Registry System: 3,3-dimethylphthalide(1689-09-4)

Safety Data

• Hazardous Substances Data: 1689-09-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 68, p. 9423, 2003 DOI: 10.1021/jo0350763

InChI:InChI=1/C10H10O2/c1-10(2)8-6-4-3-5-7(8)9(11)12-10/h3-6H,1-2H3

Upstream product

• 85-44-9 phthalic anhydride 
• 917-64-6 methyl magnesium iodide 
• 84-66-2 Diethyl phthalate 
• 676-58-4 methylmagnesium chloride 
• 544-97-8 dimethyl zinc(II) 
• 88-95-9 Phthaloyl dichloride 
• 75-16-1 methylmagnesium bromide 
• 60-29-7 diethyl ether 
• 7664-93-9 sulfuric acid 
• 797806-02-1 1,1-dimethyl-3-methylene-phthalan 
• 74-88-4 methyl iodide 
• 98-01-1 furfural 
• 7073-69-0 2-(2-bromophenyl)propanol 
• 201230-82-2 carbon monoxide 

Downstream Products

• 3609-46-9 2-(prop-1-en-2-yl)benzoic acid 
• 2438-04-2 2-isopropylbenzoic acid 
• 61490-94-6 2-(α-hydroxy-isopropyl)-benzoic acid ; potassium salt 
• 40066-10-2 E-1-(phenylethenyl)-3,3-dimethyl-1,3-dihydro-1-isobenzofuranol 
• 1023-91-2 2-(1-hydroxy-1-methyl-ethyl)-benzophenone cyclohemiacetal 
• 1719-16-0 1-[2-(1-hydroxy-1-methyl-ethyl)-phenyl]-3-phenyl-propynone cyclohemiacetal 
• 54537-56-3 1-Benzyl-1-hydroxy-3,3-dimethylphthalan 
• 32724-05-3 3-(4-bromo-phenyl)-1-[2-(1-hydroxy-1-methyl-ethyl)-phenyl]-propynone cyclohemiacetal 
• 32724-04-2 3-(4-chloro-phenyl)-1-[2-(1-hydroxy-1-methyl-ethyl)-phenyl]-propynone cyclohemiacetal 
• 40066-15-7 3,3-Dimethyl-1-phenethyl-1-phthalanol 
• 40066-14-6 3,3-Dimethyl-1-cis-styryl-1-phthalanol 
• 1521-94-4 1,3,3-Trimethyl-1,3-dihydro-1-isobenzofuranol 
• 55549-01-4 α,α-dimethyl-o-xylene α,α'-diol 
• 14308-16-8 1-methoxy-1-(4-methoxyphenyl)-3,3-dimethyl-1,3-dihydroisobenzofuran 

Relevant articles and documents

Lactone Formation in the Oxidation of Diols with N-Iodosuccinimide and Silver Acetate

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A new ring enlargement reaction of γ-lactones to seven-membered cyclic ethers via intramolecular endo-mode cyclisation of the ω-hydroxy allenyl ketone intermediates in situ

Phthalides 1a-f were treated with prop-2-ynylmagnesium bromide followed by treatment with 20% HCl in one pot to give the corresponding seven-membered cyclic ethers, benzoxepins 4a-f.

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Electron-Transfer-Induced Intramolecular Heck Carbonylation Reactions Leading to Benzolactones and Benzolactams

A metal-catalyst-free intramolecular Heck carbonylation reaction of benzyl alcohols and benzyl amines with carbon monoxide under heating at 250 °C affords the corresponding benzolactones and benzolactams in good to excellent yields. A hybrid radical/ionic chain mechanism, involving electron transfer from radical anions generated by nucleophilic attack of alcohols or amines on intermediate acyl radicals, is proposed.

Phthalide synthesis through dehydrogenated lactonization of the C(sp3)-H bond by photoredox catalysis

A practical and efficient method is established for the direct oxidative lactonization of the C(sp3)-H bonds relying on visible-light-induced photoredox catalysis. This protocol expediently allows the delivery of diverse phthalides using oxygen as the sole terminal oxidant under metal-free conditions at room temperature. Notably, the choice of an appropriate hydrogen atom transfer (HAT) cocatalyst is revealed to be critical for the success of this process.

Copper-catalyzed aerobic double functionalization of benzylic C(sp3)-H bonds for the synthesis of 3-hydroxyisoindolinones

A copper-catalyzed aerobic 3-hydroxyisoindolinone synthesis was developed via the benzylic double C(sp3)-H functionalization of 2-alkylbenzamides. In this reaction, molecular oxygen was used as both an oxidant for C(sp3)-H functionalization and an oxygen source. Our method can be extended to diverse benzylic C(sp3)-H bonds and shows excellent functional group tolerance. This journal is