491-31-6

Basic information

• Product Name: 1H-2-Benzopyran-1-one
• Synonyms: Isocoumarin;2,1-benzopyrone;ISOCUMARINE;3,4-Dehydro-1-isochromanone;isochromen-1-one;1H-isochromen-1-one
• CAS NO: 491-31-6
• Molecular Formula: C₉H₆O₂
• Molecular Weight: 146.14274
• Mol File: 491-31-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 47°C
• Boiling Point: 286°C (estimate)
• Flash Point: 103.5°C
• Appearance: /
• Density: 1.1674 (rough estimate)
• Vapor Pressure: 0.0111mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• CAS DataBase Reference: 1H-2-Benzopyran-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-2-Benzopyran-1-one(491-31-6)
• EPA Substance Registry System: 1H-2-Benzopyran-1-one(491-31-6)

Safety Data

• Hazardous Substances Data: 491-31-6(Hazardous Substances Data)

Usage

Description

1H-2-Benzopyran-1-one, also known as 1H-isochromene, is the simplest member of the isocoumarin class. It is a chemical compound characterized by a benzopyran ring system with an oxo group substitution at position 1. This structure grants it unique properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
1H-2-Benzopyran-1-one is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
1H-2-Benzopyran-1-one serves as a versatile building block in organic chemistry, enabling the creation of a wide range of chemical compounds with diverse properties and applications.
Used in Research and Development:
Due to its unique structure and reactivity, 1H-2-Benzopyran-1-one is utilized in research and development for the exploration of new chemical reactions, mechanisms, and potential applications in various industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 5274, 1984 DOI: 10.1021/ja00330a041Journal of Heterocyclic Chemistry, 27, p. 1419, 1990 DOI: 10.1002/jhet.5570270544Tetrahedron Letters, 25, p. 4459, 1984 DOI: 10.1016/S0040-4039(01)81466-0

InChI:InChI=1/C9H6O2/c10-9-8-4-2-1-3-7(8)5-6-11-9/h1-6H

Upstream product

• 90-15-3 α-naphthol 
• 35847-40-6 1-diazo-(1H)-indene 
• 78364-23-5 4-Methoxymethylen-3,4-dihydro-1H-2-benzopyran-1,3-dion 
• 74-85-1 ethene 
• 65-85-0 benzoic acid 
• 135-19-3 β-naphthol 
• 480-90-0 1H-inden-1-one 
• 62252-26-0 JLK 6 
• 103-71-9 phenyl isocyanate 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 524-42-5 1,2-naphthoquinone 
• 105-38-4 vinyl propionate 
• 27326-43-8 2-vinylbenzoic acid 

Downstream Products

• 38752-99-7 15,16,17,18,19,20-hexahydroyohimban-21-one 
• 21201-50-3 2-Hydroxyisocarbostyril 
• 491-30-5 1-hydroxyisoquinoline 
• 90535-98-1 (2-hydroxymethyl-phenyl)-acetaldehyde 
• 96719-92-5 2-[2-(3-Methoxy-phenyl)-ethyl]-2H-isoquinolin-1-one 
• 62499-91-6 2-(formylmethyl)benzoic acid 
• 96719-94-7 2-[2-(3-Methoxy-phenyl)-ethyl]-3,4,5,6,7,8-hexahydro-2H-isoquinolin-1-one 
• 96719-93-6 2-[2-(3-Methoxy-phenyl)-ethyl]-3,4-dihydro-2H-isoquinolin-1-one 
• 96719-96-9 2-[2-(3-Methoxy-phenyl)-ethyl]-1,2,3,4,5,6,7,8-octahydro-isoquinoline; hydrochloride 
• 96719-95-8 2-[2-(3-Methoxy-phenyl)-ethyl]-1,2,3,4-tetrahydro-isoquinoline; hydrochloride 
• 3297-72-1 1-phenylisoquinoline 
• 493-05-0 isochromane 
• 6346-00-5 2-(2-hydroxyethyl)benzyl alcohol 
• 66193-87-1 2-amino-1,2-dihydroisoquinolin-1(2H)-one 

Relevant articles and documents

Ag(i)-Promoted homo-dimerization of 2-(alk-2-yn-1-onyl)-1-alkynylbenzenesviaa [4 + 2] cycloaddition of benzopyrylium ions: access to structurally unique naphthalenes

Herein we report a Ag(i)-promoted homo-dimerization of 2-(alk-2-yn-1-onyl)-1-alkynylbenzenes for the synthesis of structurally novel and functionalized naphthalene derivatives. This transformation exhibits a broad scope for the alkyl as well as aryl groups present on alkynes. Observations made from control experiments suggest the possible mechanism as (i) the homo-dimerization of thein situgenerated benzopyrylium ion intermediates through a head-tail [4 + 2] cycloaddition, followed by (ii) the competitive ring-openingvs. decarbonylative aromatization of the adduct to give formylated and deformylated naphthalenes, respectively.

Rhodium(I)-Catalyzed Decarbonylative Aerobic Oxidation of Cyclic α-Diketones: A Regioselective Single Carbon Extrusion Strategy

A rhodium-catalyzed decarbonylative aerobic oxidation of cyclic α-diketones has been developed for the first time, where the regioselective formations of α-pyrones and isocoumarins have been achieved. The current decarbonylative aerobic oxidation pathway proceeds via the C-C bond cleavage followed by a C-O bond formation, representing a biomimetic oxidation approach to unsaturated six-membered cyclic lactones. The unique ability of rhodium catalysts to induce the decarbonylative aerobic oxidation opens up a new synthetic toolbox that utilizes the "regioselective single carbon" extrusion strategy.

Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters

Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack on the silyl enol ethers. The generated leaving compound abstracts a proton to regenerate the silyl enol ether structure.