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

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

Used in Chemical Synthesis:
6-BROMOISOCHROMAN is used as a reagent for the study of manganese dioxide-methanesulfonic acid promoted dehydrogenative alkylation of sp3 C-H bonds adjacent to heteroatoms. This application is significant in the field of organic chemistry, as it aids in the development of new synthetic methods and the creation of complex molecular structures.

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

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

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.

A Phosphine-Catalyzed Novel Asymmetric [3+2] Cycloaddition of C,N-Cyclic Azomethine Imines with δ-Substituted Allenoates

Catalytic asymmetric [3+2] cycloadditions of C,N-cyclic azomethine imines with δ-substituted allenoates have been developed in the presence of (S)-Me-f-KetalPhos, affording functionalized tetrahydroquinoline frameworks in good yields with high diastereo- and good enantioselectivities under mild condition. The substrate scope has been also examined. This is the first time that δ-substituted allenoates have been applied as a δ,γ-C-C bond participated C 2 synthon in asymmetric synthesis. Another round: Catalytic asymmetric [3+2] cycloaddition of C,N-cyclic azomethine imines with δ-substituted allenoates have been developed in the presence of (S)-Me-f-KetalPhos, affording functionalized tetrahydroquinoline frameworks in good yields with high diastereo- and good enantioselectivities under mild conditions. This is the first example applying δ-substituted allenoates as C 2 synthons in asymmetric δ,γ-C-C bond formation.

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.

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.

Catalytic enantioselective 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with α,β-unsaturated aldehydes

(Figure Presented) A yet-unexploited class of azomethine imines, C,N-cyclic azomethine imines, could be successfully employed in highly enantioselective 1,3-dipolar cycloaddition with enals catalyzed by titanium-BINOLate to give pharmaceutically attractive tetrahydroisoquinoline and piperidine motifs. Copyright

Synthesis of chromanyl and dihydrobenzofuranyl piperazines

The synthesis of a series of regioisomeric chromanyl and dihydrobenzofuranyl piperazines is described.

PIPERAZINYLPHENALKYL LACTAM/AMINE LIGANDS FOR THE 5HT1B RECEPTOR

The present invention relates to novel derivatives, that are compounds of Formula (I), wherein R1, R2, R3, R14, X, Y, n and m are defined herein, their pharmaceutically acceptable salts, pharmaceutical compositions and methods using said compounds in treating or preventing depression, anxiety, obsessive compulsive disorder (OCD) and other disorders for which selective antagonists, inverse agonists and partial agonists of serotonin 1 (5-HT1) receptors, specifically, antagonists of 5-HT1B are useful.

New substituted isochromans

Isochromans with substituents in the aromatic ring are described. They are synthesised by cyclisation of related chloromethyl-2-phenylethyl ethers. The activated 1-position of the isochromans is essential for obtaining potential drugs.