270-75-7

Basic information

• Product Name: Isobenzofuran
• Synonyms: Benzo[c]furan
• CAS NO: 270-75-7
• Molecular Formula: C₈H₆O
• Molecular Weight: 118.13
• Mol File: 270-75-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 190.8°C at 760 mmHg
• Flash Point: 68.4°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 0.737mmHg at 25°C
• Refractive Index: 1.6
• CAS DataBase Reference: Isobenzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: Isobenzofuran(270-75-7)
• EPA Substance Registry System: Isobenzofuran(270-75-7)

Safety Data

• Hazardous Substances Data: 270-75-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H6O/c1-2-4-8-6-9-5-7(8)3-1/h1-6H

Upstream product

• 75802-19-6 1-Ethoxy-1,3-dihydroisobenzofuran 
• 6321-72-8 9-hydroxy-10-methyl-9-phenyl-9,10-dihydroacridine 
• 708-14-5 phthalide-3-carboxylic acid 
• 99682-60-7 9-methoxy-10-methyl-9-phenyl-9,10-dihydroacridine 

Downstream Products

• 84657-73-8 C₁₆H₁₂O₂ 
• 95641-37-5 2,4,7-trimethyl-5,6-diphenyl-1H-isoindole-1,3(2H)-dione 
• 98652-92-7 (1α,1aα,2β,7β,7aα)-1a,2,7,7a-tetrahydro-2,7-epoxy-1H-cyclopropa-naphthalene-1-carbaldehyde 
• 98717-53-4 (1α,1aα,2α,7α,7aα)-1a,2,7,7a-tetrahydro-2,7-epoxy-1H-cyclopropa-naphthalene-1-carbaldehyde 
• 98717-52-3 (1aα,1bβ,2β,7β,7bα)-1a,1b,2,7,7a,7b-hexahydro-2,7-epoxynaphto<2',3':3,4>cyclobuta<1,2-b>oxiren 
• 98652-91-6 (1aα,1bβ,2α,7α,7aβ,7bα)-1a,1b,2,7,7a,7b-hexahydro-2,7-epoxynaphtho<2',3':3,4>cyclobuta<1,2-b>oxiren 
• 84657-73-8 (5α,6β,11β,12α)-5,6,11,12-tetrahydro-5,12:6,11-diepoxydibenzocyclooctene 
• 84657-74-9 4,5,10,11-tetrahydro-5,10-epoxy-4,11-ethenobenzo<5,6>cyclo-octa<1,2-c>furan 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 198707-81-2 2-(3-bromophenethyl)benzoic acid 
• 1010391-11-3 C₂₅H₂₅NO₂ 
• 4752-10-7 1,4-dichlorophthalazine 
• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 66611-15-2 3-acetylbenzo[b]furan 

Relevant articles and documents

BENZINDENE AND ITS KATZ REACTION

A novel and very short synthesis of the useful title hydrocarbon 2 is presented.Its key step is based on a Diels-Alder reaction of isobenzofuran 4.The lithium salt of 2 gives a remarkably stable valence isomer of anthracene 1 in a reaction analogous to the indene -> benzobenzvalene transformation.

The Chemistry of Phthalide-3-carboxylic Acid. II. Decarboxylation of Salts in the Presence of Aldehydes

Salts of phthalide-3-carboxylic acid decarboxylate in the presence of aromatic aldehydes to give mixtures of the 3-(arylhydroxymethyl)phthalide (2) and the 2-aryl-3-hydroxyindenone (3).The former may be obtained exclusively in the presence of the weak proton donor, triethyl(2-phenylethyl)ammonium chloride, and the latter in the presence of crown ethers or after longer reaction times.A study of the effect of different cations allows a mechanism to be deduced.

1-Lithio- and 1,3-Dilithioisobenzofuran: Formation and Reactions with Electrophiles

The acetal 1 reacts with 1 equiv of alkyllithium in the presence of catalytic diisopropylamine to form isobenzofuran (2), which with an additional equivalent of alkyllithium gives 1-lithioisobenzofuran (3).Solutions of 3 have been treated with various electrophiles and the resulting products characterized by NMR and as cycloadducts formed on addition of dienophiles.Lithiation of 2 occurs cleanly at C-1, as shown by quenching with D2O.Both the metalation and subsequent alkylation reactions are more rapid in THF than in ether.Reaction of 3 with CH3I gives 1-methylisobenzofuran (6) as the major product, accompanied by some 1,3-dialkylated material.Further treatment of 6 with alkyllithium results in specific lithiation at C-3 to give 14, as demonstrated by deuteration and analysis of cycloadducts by 2H NMR.Ethylation of 14 gives 1-ethyl-3-methylisobenzofuran, illustrating the feasibility of a one-pot procedure for preparing unsymmetrically disubstituted isobenzofurans.Dilithiation of 2 occurs when excess base is employed in THF, and this allows the direct formation of some symmetrical 1,3-disubstituted isobenzofurans.The 1-alkyl- and 1,3-dialkylisobenzofurans are moderately stable in neutral or mildly basic solution, resembling the parent 2 in this respect.Exchange reactions demonstrate that isobenzofuran is more acidic than both furan and diisopropylamine.