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

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

Uses

Used in Organic Synthesis:
2-(2-Bromoethyl)benzaldehyde is used as a reagent in organic synthesis for its ability to participate in a range of chemical reactions, making it a valuable component in the creation of various organic compounds.
Used in Scientific Research:
In the field of scientific research, 2-(2-Bromoethyl)benzaldehyde is used as a research reagent, contributing to the development and understanding of new chemical processes and compounds. Its unique structure and reactivity make it an important tool for researchers in chemistry and related fields.

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

Upstream product

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

Downstream Products

• 75802-22-1 1-ethoxyisochromane 
• 3230-65-7 3,4-dihydroisoquinoline 
• 24423-87-8 3,4-dihydro-isoquinoline 2-oxide 
• 14692-38-7 2,3,6,10b-tetrahydro-5H-thiazolo[2,3-a]isoquinoline 
• 5811-08-5 2,3,4,6,7,11b-hexahydro-[1,3]oxazino[2,3-a]isoquinoline 
• 132283-65-9 (1'R)-2-(2-hydroxy-1-phenylethyl)-3,4-dihydroisoquinolinium bromide 
• 145083-91-6 2-(2-azidoethyl)benzaldehyde 
• 87992-85-6 2-(2-Methoxy-phenyl)-3,4-dihydro-isoquinolinium; bromide 
• 41852-28-2 N-p-Tolyl-3,4-dihydro-isochinoliniumbromid 
• 55662-90-3 2-(4-methoxyphenyl)-3,4-dihydroisoquinolinium bromide 
• 41852-30-6 2-(4-nitrophenyl)-3,4-dihydroisoquinolin-2-ium bromide 
• 87992-87-8 2-(3-Chloro-phenyl)-3,4-dihydro-isoquinolinium; bromide 
• 87992-88-9 2-(3-nitrophenyl)-3,4-dihydroisoquinolin-2-ium bromide 
• 62753-44-0 2-Methyl-3,4-dihydroisoquinolinium bromide 

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.

Dihydroisoquinolinium salts: Catalysts for asymmetric epoxidation

A range of dihydroisoquinolinium salts were prepared and tested as asymmetric epoxidation catalysts. The factors affecting enantioselectivity of catalytic asymmetric epoxidation process were also discussed. The asymmetric epoxidation reaction employed alkaline hydrogen peroxide and a chiral polypeptide derived from a naturally occurring amino acid, leucine.

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.

Ytterbium-Catalyzed Intramolecular [3 + 2] Cycloaddition based on Furan Dearomatization to Construct Fused Triazoles

The 1,2,3-triazole-containing polycyclic architecture widely exists in a broad spectrum of synthetic bioactive molecules, and the development of expeditious methods to synthesize these skeletons remains a challenging task. In this work, the catalytic cyclization of biomass-derived 2-furylcarbinols with an azide to form fused triazoles is described. This approach takes advantage of a single catalyst Yb(OTf)3 and operates via a furfuryl-cation-induced intramolecular [3 + 2] cycloaddition/furan ring-opening cascade.

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.

An Intramolecular Cycloaddition Approach to the Kauranoid Family of Diterpene Metabolites

Synthetic studies toward the ent-kauranoid family of diterpene natural products are reported. An intramolecular (4 + 3) cycloaddition allows the direct elaboration of diverse natural product frameworks, encompassing a challenging bicyclo[3.2.1]octane core. The established routes comprise only a few synthetic operations (3-5 steps), transforming a range of simple starting materials into the tetracyclic scaffolds that are commonly found in many ent-kaurene metabolites.

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.

A rhodium-catalysed three-component reaction to access C1-substituted tetrahydroisoquinolines

A rhodium-catalyzed three-component reaction of diazo compounds, anilines and C,N-cyclic azomethine imines via trapping of transient ammonium ylides was developed. This reaction provided a simple and convenient approach for the synthesis of pharmaceutically intriguing tetrahydroisoquinoline derivatives in moderate to good yields (36-85%) with good diastereoselectivities (up to 95 : 5 dr) under mild reaction conditions.

USE OF DIHYDROISOQUINOLINIUM SALTS FOR TREATING KERATIN MATERIALS, COMPOSITIONS AND IMPLEMENTATION PROCESSES

Use of dihydroisoquinolinium salts for treating keratin materials, compositions and implementation processes The present invention relates to the use of one or more dihydroisoquinolinium salts for treating keratin materials, in particular keratin fibres, especially human keratin fibres such as the hair. The invention also relates to a process for treating keratin materials using said salts and optionally in the presence of one or more chemical oxidizing agents. A subjectof the invention is also a composition for lightening keratin materials, comprising one or more dihydroisoquinolinium salts as defined below and one or more chemical oxidizing agents.

Reactions Catalysed by a Binuclear Copper Complex: Relay Aerobic Oxidation of N-Aryl Tetrahydroisoquinolines to Dihydroisoquinolones with a Vitamin B1 Analogue

N-Aryl tetrahydroisoquinolines were oxidised to dihydroisoquinolones through the relay catalysis of a binuclear paddle-wheel copper complex and a vitamin B1 analogue with oxygen as oxidant. Mechanistic studies revealed that the copper catalyst oxidises amines to the corresponding iminium salts, which are then oxygenated to lactam products by catalysis of the vitamin B1 analogue.