29539-21-7

Basic information

• Product Name: 3-METHYL-ISOCHROMEN-1-ONE
• Synonyms: 3-METHYL-ISOCHROMEN-1-ONE
• CAS NO: 29539-21-7
• Molecular Formula: C₁₀H₈O₂
• Molecular Weight: 160.16932
• Mol File: 29539-21-7.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-METHYL-ISOCHROMEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-ISOCHROMEN-1-ONE(29539-21-7)
• EPA Substance Registry System: 3-METHYL-ISOCHROMEN-1-ONE(29539-21-7)

Safety Data

• Hazardous Substances Data: 29539-21-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 5298, 1993 DOI: 10.1021/jo00072a004

Upstream product

• 88-67-5 2-Iodobenzoic acid 
• 53915-69-8 allenyltributylstannane 
• 10282-57-2 2-bromobenzanilide 
• 123-54-6 acetylacetone 
• 15310-01-7 benodanil 
• 93-91-4 1-phenylbutan-1,3-dione 
• 6833-13-2 2-chlorobenzanilide 
• 61260-15-9 dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate 
• 63830-81-9 2-(2-oxopropyl)benzaldehyde 
• 7647-01-0 hydrogenchloride 
• 7114-78-5 2,3-Dimethyl-1-oxo-1,2-dihydroisoquinoline 
• 113125-50-1 (1-Acetyl-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-phosphonic acid dimethyl ester 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 78-95-5 chloroacetone 

Downstream Products

• 101640-65-7 1-(2-acetylphenyl)propane-2-one 
• 93645-90-0 1-(2-benzoylphenyl)propan-2-one 
• 78868-57-2 3-Phenoxymethylisocoumarin 
• 29428-84-0 trans-artemidin 
• 34328-51-3 1-oxo-1H-isochromene-3-carbaldehyde 
• 27107-35-3 5-Methyl-s-triazolo<3,4-a>isochinolin 
• 7115-16-4 1-chloro-3-methyl-isoquinoline 
• 7114-80-9 3-methylisoquinolone 
• 93361-24-1 2-(3-methyl-1-oxoisoquinolin-2(1H)-yl)benzonitrile 
• 7115-14-2 2-(2-hydroxyimino-propyl)-benzoic acid 
• 2852-91-7 (2-carboxyphenyl)acetone 
• 7114-80-9 3-methylisoquinolin-1-ol 
• 93361-25-2 methyl 2-(3-methyl-1-oxoisoquinolin-2(1H)-yl)benzoate 
• 93361-26-3 2-(2-carbamoylphenyl)-3-methylisocarbostyril 

Relevant articles and documents

Reaction of arynes with trifluoroacetylated β-diketones: Novel formation of isocoumarins and phenanthrenes

Polysubstituted isocoumarins were synthesized by the reaction of substituted 2-(trimethylsilyl)aryl triflates with trifluoromethylated β-diketones in the presence of CsF. The reaction proceeded through carbon-carbon bond insertion of aryne and intramolecular cyclization to form intermediates of alcohol anions, which extruded trifluoromethyl anion to afford isocoumarins. By using CuBr as a catalyst, 2 eq. of aryne reacted with β-diketones to afford phenanthrenes and 1,2-diarylethanones. Although reaction of 2-(trimethylsilyl)phenyl triflate with 1,1,1-trifluoro-4′-methylbenzoylacetone in the presence of CsF gave 3-(4′-methylphenyl)isocoumarin in 67% yield, addition of 0.2 eq. of CuCN resulted in the formation of 9-(4-methylbenzoyl)-10-trifluoromethylphenanthrene in 35% yield.

Ortho-Induced transition-metal-free C-arylation cyclization reaction for the synthesis of polysubstituted isocoumarins

A new protocol for the synthesis of polysubstituted isocoumarins from 2-iodobenzoic acid and β-diketone compounds has been developed. The occurrence of C-arylation cyclization reaction in transition-metal-free systems and ortho-induced substrates has been exploited. Reactions using these inexpensive conditions have displayed high functional group tolerance and excellent yields.

Synthesis of isocoumarins and α-pyrones via tandem Stille reaction/heterocyclization

A general route to α-pyrones and 3-substituted isocoumarins from (Z)-iodovinylic acids 1a-f or 2-iodobenzoic acids 4a-c is described, including compounds bearing a substituent on the aromatic ring. Treatment of (Z)-β-iodovinylic acids 1a-f or 2-iodobenzoic acids 4a-c with various allenyl-tributyltin reagents in the presence of palladium acetate, triphenylphosphine, and tetrabutylammonium bromide in dimethylformamide provided good yields of the corresponding α-pyrones 3a-k or 3-substituted isocoumarins 5a-g via tandem Stille reaction and 6-endo-dig oxacyclization.