22901-09-3

Basic information

• Product Name: 2-(2-Bromoethyl)benzaldehyde
• Synonyms: o-(2-Bromoethyl)benzaldehyde;2-(2-BROMOETHYL)BENZALDEHYDE;1-FORMYL-2(2-BROMOETHYL)BENZENE;2-BROMOETHYL BENZALDEHYDE;1-ForMyl-2(2-broMoethyl)benzene/2-(2-broMoethyl)benzaldehyde
• CAS NO: 22901-09-3
• Molecular Formula: C₉H₉BrO
• Molecular Weight: 213.07
• Mol File: 22901-09-3.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 2743°C
• Flash Point: 81°C
• Appearance: /
• Density: 1.448
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.5858
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 2-(2-Bromoethyl)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Bromoethyl)benzaldehyde(22901-09-3)
• EPA Substance Registry System: 2-(2-Bromoethyl)benzaldehyde(22901-09-3)

Safety Data

• Hazardous Substances Data: 22901-09-3(Hazardous Substances Data)

Usage

General Description

2-(2-Bromoethyl)benzaldehyde is a chemical compound often used in organic synthesis. Its molecular formula is C9H9BrO. The primary feature of this compound is its aromatic structure combined with its bromine and aldehyde functional groups, which allows it to participate in a range of chemical reactions. Its properties include a molecular weight of approximately 227.07 g/mol and a heavy atom count of 11. Safety precautions must be followed while handling, as it can cause skin, eye and respiratory irritations. This chemical is often used in scientific research as a reagent.

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

Upstream product

• 81616-92-4 1-(2-methoxyethoxy)methoxy-2-phenylethane 
• 19275-61-7 bis(3,4-dihydro-1H-benzopyran-1-yl) ether 
• 10035-10-6 hydrogen bromide 
• 50683-32-4 1-Bromoisochromane 
• 493-05-0 isochromane 
• 103-82-2 phenylacetic acid 
• 54673-12-0 (2-(methoxymethoxy)ethyl)benzene 
• 60-12-8 2-phenylethanol 
• 34818-49-0 1-methoxyisochromane 

Downstream Products

• 75802-22-1 1-ethoxyisochromane 
• 5811-08-5 2,3,4,6,7,11b-hexahydro-[1,3]oxazino[2,3-a]isoquinoline 
• 22901-10-6 3-<2'-(β-Bromethyl)-phenyl>-3-hydroxypropansaeureethylester 
• 145083-93-8 o-(Azidoethyl)benzonitrile 
• 145083-94-9 C₁₀H₁₂N₄S 
• 145083-95-0 5-(o-cyano)phenethylamino-1,2,3,4-thiatriazole 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 37939-38-1 o-(1-hydroxyethyl)phenethyl bromide 
• 42046-26-4 benzoyl(3,4-dihydroisoquinolinium-2-yl)azanide 

Relevant articles and documents

Asymmetric synthesis of tetrahydroisoquinoline derivatives through 1, 3-dipolar cycloaddition of C, N-cyclic azomethine imines with allyl alkyl ketones

[3 + 2] A 1, 3-Dipolar cycloaddition of C, N-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with good diastereoselectivities and enantioselectivities (up to >25:1 dr, >95% ee). Moreover, the absolute configuration of the product was previously determined by using the quantum electronic circular dichroism calculation and ECD spectrum method.

Studies on Cu-catalyzed asymmetric alkynylation of tetrahydroisoquinoline derivatives

Enantioselective C-C bond formations between the sp3 C-H bond of prochiral CH2 and terminal alkynes via the cross-dehydrogenative coupling (CDC) reaction were studied. Efficient asymmetric syntheses of alkynyl tetrahydroisoquinoline derivatives were achieved by using a catalytic amount of CuOTf together with PyBox chiral ligand. When dihydroisoquinolinium salts were used as electrophiles, the combination of CuBr/QUINAP provided the best results for asymmetric syntheses of alkynyl tetrahydroisoquinoline derivatives. The factors influencing the enantioselectivity were studied.

Hydrogen-Bonding-Promoted Cascade Rearrangement Involving the Enlargement of Two Rings: Efficient Access to Polycyclic Quinoline Derivatives

An efficient cascade reaction of tryptamine-derived isocyanides with C,N-cyclic azomethine imines is described. The polycyclic pyrrolo[2,3-c]quinoline derivatives, which benefited from rearrangement process driven by hydrogen bonding, could be directly assembled in moderate to good yields (40–87 %) under metal-free and mild conditions. This transformation involved four new heterocyclic rings formations and uniquely, ring opening of indole as well as ring expansion of C,N-cyclic azomethine imine. Both experimental and DFT studies provided guidance on the in-depth insight into the reaction pathways and hydrogen bonding was identified to lower the free energy barrier in transition states. This work constitutes a rare example of tryptamine-derived isocyanide-based cascade reactions, and potentially could be a powerful synthetic strategy for accessing polycyclic analogues involved in natural products.

Enantioselective synthesis of tetrahydroisoquinoline derivatives via chiral-at-metal rhodium complex catalyzed [3+2] cycloaddition

An asymmetric [3+2] cycloaddition of C,N-cyclic azomethine imines with α,β-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal rhodium complex has been developed. The corresponding C-1-substituted tetrahydroisoquinoline derivatives were obtained in high yields (>90%) with excellent stereoselectivities (up to 99% ee and >20?:?1 dr). The reaction can be conducted on a gram-scale using a low catalyst loading (0.5 mol%) with high yield and selectivity.