38002-88-9

Basic information

• Product Name: 2,2-DIMETHYL-2,3-DIHYDRO-1-BENZOFURAN-7-CARBALDEHYDE
• Synonyms: 2,2-DIMETHYL-2,3-DIHYDRO-1-BENZOFURAN-7-CARBALDEHYDE;2,2-Dimethyl-2,3-dihydro-1-benzofurane-7-carbaldehyde;2,3-Dihydro-2,2-dimethylbenzo[b]furan-7-carboxaldehyde;2,2-dimethyl-2,3-dihydrobenzofuran-7-carbaldehyde;2,2-DIMETHYL-2,3-DIHYDRO-1-BENZOFURAN-7-CARBALDEHYDE(WXC09893)
• CAS NO: 38002-88-9
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21
• Mol File: 38002-88-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 81 °C
• Boiling Point: 278.4°C at 760 mmHg
• Flash Point: 121.8°C
• Appearance: /
• Density: 1.103g/cm³
• Vapor Pressure: 0.00426mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: 2,2-DIMETHYL-2,3-DIHYDRO-1-BENZOFURAN-7-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIMETHYL-2,3-DIHYDRO-1-BENZOFURAN-7-CARBALDEHYDE(38002-88-9)
• EPA Substance Registry System: 2,2-DIMETHYL-2,3-DIHYDRO-1-BENZOFURAN-7-CARBALDEHYDE(38002-88-9)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 38002-88-9(Hazardous Substances Data)

Usage

General Description

2,2-DIMETHYL-2,3-DIHYDRO-1-BENZOFURAN-7-CARBALDEHYDE is a chemical compound that belongs to the class of aldehydes. It is a colorless liquid with a strong, sweet odor and is commonly used in the manufacture of fragrances and flavorings. 2,2-DIMETHYL-2,3-DIHYDRO-1-BENZOFURAN-7-CARBALDEHYDE is a versatile building block in organic synthesis and is often used in the production of pharmaceuticals, agrochemicals, and organic compounds. It is also used as a fragrance ingredient in various personal care products and perfumes. The compound has potential applications in the development of new drugs due to its unique structure and properties.

InChI:InChI=1/C11H12O2/c1-11(2)6-8-4-3-5-9(7-12)10(8)13-11/h3-5,7H,6H2,1-2H3

Upstream product

• 38002-87-8 O-methallylsalicylaldehyde 
• 6337-33-3 2,2-dimethyl-2,3-dihydro-1-benzofuran 
• 109-72-8 n-butyllithium 
• 308110-31-8 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl trifluoromethasulfonate 
• 99517-60-9 methyl 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate 
• 1563-38-8 2,3-dihydro-2,2-dimethylbenzofuran-7-ol 
• 38002-89-0 2,3-dihydro-2,2-dimethylbenzofuran-7-ylmethanol 
• 162971-77-9 2-(β-methylallyl)phenol-6-carbaldehyde 

Downstream Products

• 308110-32-9 4-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)(hydroxy)methyl]-N,N-diethylbenzamide 
• 38002-89-0 2,3-dihydro-2,2-dimethylbenzofuran-7-ylmethanol 
• 1312470-13-5 C₂₃H₂₃NO₂ 
• 868755-46-8 (2,2-dimethyl-2,3-dihydro-benzofuran-7-ylmethyl)-methyl-amine 
• 308110-33-0 4-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)(1-piperazinyl)methyl]-N,N-diethylbenzamide 

Relevant articles and documents

New diarylmethylpiperazines as potent and selective nonpeptidic δ opioid receptor agonists with increased in vitro metabolic stability

Nonpeptide δ opioid agonists are analgesics with a potentially improved side-effect and abuse liability profile, compared to classical opioids. Andrews analysis of the NIH nonpeptide lead SNC-80 suggested the removal of substituents not predicted to contribute to binding. This approach led to a simplified lead, N,N-diethyl-4-[phenyl(1-piperazinyl)methyl]benzamide (1), which retained potent binding affinity and selectivity to the human δ receptor (IC50 = 11 nM, μ/δ = 740, κ/δ > 900) and potency as a full agonist (EC50 = 36 nM) but had a markedly reduced molecular weight, only one chiral center, and increased in vitro metabolic stability. From this lead, the key pharmacophore groups for δ receptor affinity and activation were more clearly defined by SAR and mutagenesis studies. Further structural modifications on the basis of 1 confirmed the importance of the N,N-diethylbenzamide group and the piperazine lower basic nitrogen for δ binding, in agreement with mutagenesis data. A number of piperazine N-alkyl substituents were tolerated. In contrast, modifications of the phenyl group led to the discovery of a series of diarylmethylpiperazines exemplified by N,N-diethyl-4-[1-piperazinyl(8-quinolinyl)-methyl]benzamide (56) which had an improved in vitro binding profile (IC50 = 0.5 nM, μ/δ = 1239, EC50 = 3.6 nM) and increased in vitro metabolic stability compared to SNC-80.

ONE-POT SYNTHESES OF 2,3-DIHYDRO-2,2-DIMETHYLBENZOFURAN DERIVATIVES

A tandem Claisen rearrangement-cyclization reaction of aryl methallyl ethers afforded the corresponding 2,3-dihydro-2,2-dimethylbenzofuran derivatives at -70 deg C with aluminium chloride.