182949-90-2

Basic information

• Product Name: 6-BROMOISOCHROMAN
• Synonyms: 6-BROMOISOCHROMAN;1H-2-Benzopyran, 6-bromo-3,4-dihydro;6-broMo-3,4-dihydro-1H-isochroMene;6-broMo-3,4-dihydro-1H-2-benzopyran
• CAS NO: 182949-90-2
• Molecular Formula: C9H9BrO
• Molecular Weight: 213.08
• Mol File: 182949-90-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 279.369°C at 760 mmHg
• Flash Point: 110.571°C
• Appearance: /
• Density: 1.485g/cm³
• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 6-BROMOISOCHROMAN(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMOISOCHROMAN(182949-90-2)
• EPA Substance Registry System: 6-BROMOISOCHROMAN(182949-90-2)

Safety Data

• Hazardous Substances Data: 182949-90-2(Hazardous Substances Data)

Usage

Uses

6-Bromoisochroman is a useful reagent in the study of manganese dioxide-methanesulfonic acid promoted dehydrogenative alkylation of sp3 C-H bonds adjacent to heteroatom.

InChI:InChI=1/C9H9BrO/c10-9-2-1-8-6-11-4-3-7(8)5-9/h1-2,5H,3-4,6H2

Upstream product

• 846037-84-1 1-bromo-3-(2-((2-methoxyethoxy)methoxy)ethyl)benzene 
• 3970-21-6 2-Methoxyethoxymethyl chloride 
• 28229-69-8 2-(3-bromophenyl)ethan-1-ol 
• 1878-67-7 3-Bromophenylacetic acid 
• 389090-87-3 C₁₀H₁₃BrO₂ 
• 444588-39-0 6-amino-3,4-dihydro-1H-2-benzopyran 

Downstream Products

• 1338236-51-3 C₁₈H₁₅BrO 
• 1428485-02-2 2-(6-bromoisochroman-1-yl)-1-phenylethanone 
• 1219468-18-4 N-benzoylimino-6-bromo-3,4-dihydroisoquinolinium betaine 
• 1219468-12-8 4-bromo-2-(2-bromoethyl)benzaldehyde 

Relevant articles and documents

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.

Manganese dioxide-methanesulfonic acid promoted direct dehydrogenative alkylation of sp3 C-H bonds adjacent to a heteroatom

A manganese dioxide (MnO2)-methanesulfonic acid (CH 3SO3H) oxidation system has been developed to efficiently promote direct coupling of benzylic ethers and carbamates with simple ketones via oxidative C-H bond activation.

Copper-catalyzed enantioselective additions to oxocarbenium ions: Alkynylation of isochroman acetals

We have developed an enantioselective, copper(I)-catalyzed addition of terminal alkynes to racemic isochroman acetals. This method is one of the first transition-metal-catalyzed approaches to enantioselective additions to prochiral oxocarbenium ions. In this reaction, TMSOTf is used to form the oxocarbenium ion in situ under conditions compatible with simultaneous formation of the chiral copper acetylide. By using a bis(oxazoline) ligand, good yields and enantioselectivities are observed for a variety of enantioenriched 1-alkynyl isochromans.