6337-33-3

Basic information

• Product Name: 2,3-dihydro-2,2-dimethylbenzofuran
• Synonyms: 2,3-dihydro-2,2-dimethylbenzofuran;2,2-dimethyl-2,3-dihydro-1-benzofuran;2,2-dimethyl-2,3-dihydrobenzofuran;2,2-dimethyl-3H-1-benzofuran;2,2-dimethyl-3H-benzofuran;Benzofuran, 2,3-dihydro-2,2-dimethyl-
• CAS NO: 6337-33-3
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.20168
• EINECS: 228-724-4
• Mol File: 6337-33-3.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 202.2 °C at 760 mmHg
• Flash Point: 68.2 °C
• Appearance: /
• Density: 1.001 g/cm³
• Vapor Pressure: 0.422mmHg at 25°C
• Refractive Index: 1.516
• CAS DataBase Reference: 2,3-dihydro-2,2-dimethylbenzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dihydro-2,2-dimethylbenzofuran(6337-33-3)
• EPA Substance Registry System: 2,3-dihydro-2,2-dimethylbenzofuran(6337-33-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 6337-33-3(Hazardous Substances Data)

Usage

Uses

2,2-dimethyl-2,3-dihydro-1-benzofuran (cas# 6337-33-3) is used as a reagent in the preparation of heteroaryl compounds as kynurenine-3-monooxygenase inhibitors for treatment of neurodegenerative disorders.

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 6939, 1993 DOI: 10.1016/S0040-4039(00)91836-7Synthesis, p. 950, 1984 DOI: 10.1055/s-1984-31033

InChI:InChI=1/C10H12O/c1-10(2)7-8-5-3-4-6-9(8)11-10/h3-6H,7H2,1-2H3

Upstream product

• 153529-64-7 7-(2'-hydroxy-2'-methylpropyl)-1H-benzotriazol-1-amine 
• 344296-29-3 1-bromo-2-(tert-butoxy)benzene 
• 100-86-7 2-Methyl-1-phenyl-2-propanol 
• 1286762-99-9 C₁₂H₁₇NO₄S 
• 1563-38-8 2,3-dihydro-2,2-dimethylbenzofuran-7-ol 
• 81634-60-8 1-tert-butoxy-2-chlorobenzene 
• 108-95-2 phenol 
• 90-02-8 salicylaldehyde 
• 78023-79-7 2,2-dimethyl-4H-benzo[d][1,3]dioxin 
• 90-01-7 salicylic alcohol 
• 153529-55-6 [7-(2-Hydroxy-2-methyl-propyl)-benzotriazol-1-yl]-carbamic acid tert-butyl ester 
• 20944-88-1 2-(methylallyl)phenol 
• 33316-80-2 1-(2-hydroxyphenyl)-2-methyl-2-propanol 
• 930-68-7 cyclohexenone 

Downstream Products

• 5337-94-0 5-Bromo-2,2-dimethyl-2,3-dihydrobenzo[b]furan 
• 38002-88-9 2,3-dihydro-2,2-dimethylbenzofuran-7-carboxaldehyde 
• 1232221-50-9 N-(2,2-dimethyl-2,3-dihydro-benzofuran-7-yl-methyl-idene)-N'-(7-morpholin-4-yl-2-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)hydrazine 
• 42327-95-7 2,3-Dihydro-2,2-dimethyl-7-benzofurancarbonsaeure 

Relevant articles and documents

Nickel-Catalyzed Hydrodeoxygenation of Aryl Sulfamates with Alcohols as Mild Reducing Agents

The nickel-catalyzed hydrodeoxygenation of aryl sulfamates has been developed with alcohols as mild reductants. A variety of functional groups and heterocycles were tolerated in this reaction system to give the desired products in high yields. In addition, the gram-scale process and stepwise cine-substitution were also achieved with high efficiency.

Dihydrobenzofuran production from catalytic tandem Claisen rearrangement-intramolecular hydroaryloxylation of allyl phenyl ethers in subcritical water

We herein report a mild method for the preparation of dihydrobenzofurans through hydrothermal catalytic tandem Claisen rearrangement-intramolecular hydroaryloxylation of allyl phenyl ethers. This reaction provides a new method for constructing dihydrobenzofurans, a process that is potentially applicable to natural product synthesis. SBA-15, TS-1, HZSM-5 were chosen as catalysts in a hydrothermal reaction medium between 200 and 320 °C. HZSM-5 catalyst showed the highest catalytic activity, and the effects of molar ratio of allyl phenyl ether-water, time, pressure, temperature and catalyst on the Claisen hydroaryloxylation in hydrothermal condition were investigated. The latter two process variables had the greatest influence on the product yields and distribution. A series of allyl phenyl ether derivatives were also treated in hydrothermal condition with HZSM-5 catalyst to offer high yield of corresponding dihydrobenzofurans.

Intramolecular palladium-catalyzed alkane C-H arylation from aryl chlorides

The first examples of efficient and general palladium-catalyzed intramolecular C(sp3)-H arylation of (hetero)aryl chlorides, giving rise to a variety of valuable cyclobutarenes, indanes, indolines, dihydrobenzofurans, and indanones, are described. The use of aryl and heteroaryl chlorides significantly improves the scope of C(sp3)-H arylation by facilitating the preparation of reaction substrates. Careful optimization studies have shown that the palladium ligand and the base/solvent combination are crucial to obtaining the desired class of product in high yields. Overall, three sets of reaction conditions employing PtBu3, PCyp3, or PCy3 as the palladium ligand and K 2CO3/DMF or Cs2CO3/pivalic acid/mesitylene as the base/solvent combination allowed five different classes of products to be accessed using this methodology. In total, more than 40 examples of C-H arylation have been performed successfully. When several types of C(sp3)-H bond were present in the substrate, the arylation was found to occur regioselectively at primary C-H bonds vs secondary or tertiary positions. In addition, in the presence of several primary C-H bonds, selectivity trends correlate with the size of the palladacyclic intermediate, with five-membered rings being favored over six- and seven-membered rings. Regio- and diastereoselectivity issues were studied computationally in the prototypal case of indane formation. DFT(B3PW91) calculations demonstrated that C-H activation is the rate-determining step and that the creation of a C-H agostic interaction, increasing the acidity of a geminal C-H bond, is a critical factor for the regiochemistry control.