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 
• 60-29-7 diethyl ether 
• 506-82-1 dimethylcadmium 
• 74-88-4 methyl iodide 
• 84-66-2 Diethyl phthalate 
• 676-58-4 methylmagnesium chloride 
• 544-97-8 dimethyl zinc(II) 
• 88-95-9 Phthaloyl dichloride 
• 55549-01-4 α,α-dimethyl-o-xylene α,α'-diol 
• 1696-17-9 N,N-diethylbenzamide 
• 67-64-1 acetone 
• 31952-55-3 α,α-dimethyl-2-carboxyphenylacetic anhydride 
• 75-16-1 methylmagnesium bromide 

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 
• 55549-01-4 α,α-dimethyl-o-xylene α,α'-diol 
• 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 
• 107552-78-3 C₁₉H₂₃N₃O₃S 
• 32724-10-0 4-[1-(4-chloro-phenyl)-2-(3,3-dimethyl-3H-isobenzofuran-1-ylidene)-ethylidene]-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 34068-83-2 4-[1-(4-bromo-phenyl)-2-(3,3-dimethyl-3H-isobenzofuran-1-ylidene)-ethylidene]-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 21190-34-1 (2-isopropylphenyl)methanol 

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.

Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp3)-H Lactonization of 2-Alkylbenzoic Acids

A mild and practical C(sp3)-H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2-alkylbenzoic acid substrate, magnesium ion, and bromate anion.

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