26164-08-9

Basic information

• Product Name: 3,4-dihydro-4-methyl-1H-2-benzopyran
• Synonyms: 3,4-dihydro-4-methyl-1H-2-benzopyran;4-Methyl-isochroman
• CAS NO: 26164-08-9
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.20168
• EINECS: 247-490-4
• Mol File: 26164-08-9.mol

Chemical Properties

• Boiling Point: 234.7 °C at 760 mmHg
• Flash Point: 91.3 °C
• Appearance: /
• Density: 1.006 g/cm³
• Vapor Pressure: 0.0797mmHg at 25°C
• Refractive Index: 1.519
• CAS DataBase Reference: 3,4-dihydro-4-methyl-1H-2-benzopyran(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dihydro-4-methyl-1H-2-benzopyran(26164-08-9)
• EPA Substance Registry System: 3,4-dihydro-4-methyl-1H-2-benzopyran(26164-08-9)

Safety Data

• Hazardous Substances Data: 26164-08-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H12O/c1-8-6-11-7-9-4-2-3-5-10(8)9/h2-5,8H,6-7H2,1H3

Upstream product

• 1217293-64-5 (+/-)-[1-[(2-methoxyethoxy)methoxy]propan-2-yl]benzene 
• 13662-20-9 PhCH(Me)CH₂OMOM 
• 1123-85-9 (RS)-2-phenyl-1-propanol 
• 87280-01-1 1-((allyloxy)methyl)-2-bromobenzene 
• 50-00-0 formaldehyd 

Downstream Products

• 409334-01-6 2-(2-bromo-1-methylethyl)benzaldehyde 
• 84810-47-9 cis-3,4-dihydro-1-phenyl-4-methyl-1H-2-benzopyran 
• 84810-46-8 trans-3,4-dihydro-1-phenyl-4-methyl-1H-2-benzopyran 
• 1352941-26-4 1-(4-methoxyphenyl)-4-methylisochroman 
• 4175-53-5 trans-1,3-dimethyl-indane 

Relevant articles and documents

A new tetradentate nitrogen ligand for organometallic catalysis: electrochemical nickel-catalyzed intramolecular cyclization

The new tetraaza-molecule, 1 has been synthesized and used as a ligand for a cationic mononuclear nickel(II) complex.This complex is an efficient catalysts for the intramolecular electrochemical cyclization of o-haloaryl compounds containing unsaturated side chains. - Keywords: Nitrogen ligand; Tetradentate; Nickel catalysis; Intramolecular cyclization

A 1H and 13C NMR Conformational Study of Methyl-Substituted Isochromanes

The 1H and the noise-decoupled 13C NMR spectra of isochromane and 13 of its methyl-substituted derivatives were recorded and analysed.The collected data were used to assign the configurations and to determine the position of the conformational equilibria based on the vicinal 1H coupling constants of the aliphatic moiety of the ring-system.In some cases the substitution site-dependent conformational energies of the methyl substituents were also used to estimate the conformer ratios.The primary and some vicinal methyl substituent effects on the 13C chemical shifts of the oxane ring carbons were derived and compared with those of 1,3-dioxanes.Their usefulness in conformational analysis is demonstrated for 1-methylisochromane.

Merging Photoredox with Br?nsted Acid Catalysis: The Cross-Dehydrogenative C?O Coupling for sp3 C?H Bond Peroxidation

A photoredox and Br?nsted acid synergistically catalyzed cross-dehydrogenative C?O coupling reaction is developed in which isochroman peroxyacetals are formed through sp3 C?H bond peroxidation. The reported method is characterized by its extremely mild reaction conditions, excellent yields, and broad substrate scope. An oxocarbenium ion p-chlorobenzenesulfonate was speculated to be the reactive intermediate. The role of hemiacetals and oxygenated dimers on the effective stabilization of the oxocarbenium ion was investigated; the presence of acid appeared to establish equilibrium between hemiacetals and oxygenated dimers with the oxocarbenium ion pairs. The broad applicability of the method highlights the potential of the protocol for molecule synthesis.

CuBr2 catalyzed bromination/oxidation of isochromans to benzaldehyde derivatives

A series of isochromans were oxidized and brominated by using 1.2 equiv of CuBr2 in CH3CN at reflux to give the corresponding bromo benzaldehydes in moderate yields. A plausible mechanism for this transformation has been suggested.

Synthesis of Chiral 3-Alkyl-3,4-dihydroisocoumarins by dynamic kinetic resolutions catalyzed by a Baeyer-Villiger Monooxygenase

"Chemical Equation Presented" Baeyer-Villiger monooxygenases have been tested, in the oxidation of racemic benzofused ketones. When employing a single mutant of phenylacetone monooxygenase (M.446G PAMO) under the proper reaction conditions, it was possible to achieve 3-substituted 3,4-dihydroisocoumarins with, high yields and optical purities through regioselective dynamic kinetic resolution processes.

Comparative study of anionic and radical cyclization for the preparation of 1,3-dimethylindans: highly stereoselective preparation of cis-1,3-disubstituted indans via intramolecular carbolithiation.

[reaction: see text] The preparation of 1,3-dimethylindans from 4-(2-bromophenyl)-1-pentene (1) and 2-(2-iodo-1-methylethyl)styrene (2) substrates via radical-mediated cyclization and intramolecular carbolithiation has been investigated. Although cyclization of the radical derived from either substrate proceeds with modest selectivity for the cis-isomer, as does cycloisomerization of the aryllithium derived from substrate 1 (cis/trans approximately 2), intramolecular cyclization of the alkyllithium derived from substrate 2 is a highly cis-selective process (cis/trans = 12).

Electrochemical Intramolecular Reductive Cyclisation Catalysed by Electrogenerated Ni(cyclam)(2+)

The intramolecular cyclisation of a series of o-halogenated aromatic compounds containing unsaturated side-chains has been developed using electrosynthesis, combined with organometallic catalysis by Ni(cyclam)Br2.