22532-62-3

Basic information

• Product Name: 4-Bromo-2-hydroxybenzaldehyde
• Synonyms: 4-BROMO-2-HYDROXY-BENZALDEHYDE;4-Bromosalicylaldehyde;2-Hydroxy-4-Bromobenzaldehyde;4-Bromo-2-hydroxybenaldehyde;D1404;4-Bromosalicylaldehyde, 5-Bromo-2-formylphenol;4-BroMo-2-hydroxybenzaldheyde;Benzaldehyde,4-broMo-2-hydroxy-
• CAS NO: 22532-62-3
• Molecular Formula: C₇H₅BrO₂
• Molecular Weight: 201.02
• EINECS: 1806241-263-5
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 22532-62-3.mol
• Article Data: 35

Chemical Properties

• Melting Point: 50-54 °C
• Boiling Point: 256.23 °C at 760 mmHg
• Flash Point: 110 °C
• Appearance: /
• Density: 1.737 g/cm³
• Vapor Pressure: 0.01mmHg at 25°C
• Refractive Index: 1.657
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in methanol.
• PKA: 7.21±0.10(Predicted)
• CAS DataBase Reference: 4-Bromo-2-hydroxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-hydroxybenzaldehyde(22532-62-3)
• EPA Substance Registry System: 4-Bromo-2-hydroxybenzaldehyde(22532-62-3)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 22-50
• Safety Statements: 60
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 22532-62-3(Hazardous Substances Data)

Usage

Description

4-Bromo-2-hydroxybenzaldehyde is an organic compound that belongs to the class of substituted salicylaldehydes. It is characterized by its off-white powder appearance and is known for its significant role in various chemical and pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
4-Bromo-2-hydroxybenzaldehyde is used as a key intermediate in the synthesis of pharmaceutical compounds. One notable example is its use in the production of BIIB042, a γ-secretase modulator, which is an important compound in the development of treatments for various neurological disorders.
Used in Organic Synthesis:
4-Bromo-2-hydroxybenzaldehyde serves as an essential raw material in organic synthesis, where it is utilized to create a wide range of chemical products. Its unique structure allows for the formation of various derivatives, making it a versatile building block in the synthesis of complex organic molecules.
Used in Agrochemicals:
4-Bromo-2-hydroxybenzaldehyde is also used as an intermediate in the development of agrochemicals, which are chemicals specifically designed to benefit crop production and control pests. Its incorporation in these products contributes to the effectiveness of agrochemicals in protecting crops and enhancing agricultural productivity.
Used in Dye Industry:
In the dye industry, 4-Bromo-2-hydroxybenzaldehyde is employed as a crucial intermediate for the synthesis of various dyes and pigments. Its chemical properties enable the creation of a diverse array of colorants that are used in different applications, such as textiles, plastics, and printing inks.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 35, p. 734, 1992 DOI: 10.1021/jm00082a014

InChI:InChI=1/C7H5BrO2/c8-6-2-1-5(4-9)7(10)3-6/h1-4,10H

Upstream product

• 59278-65-8 2-amino-4-bromobenzaldehyde 
• 67-66-3 chloroform 
• 591-20-8 3-Bromophenol 
• 50-00-0 formaldehyd 
• 16394-40-4 N-(4-bromo-2-hydroxyphenyl)acetamide 
• 108-95-2 phenol 
• 88-75-5 2-hydroxynitrobenzene 
• 95-55-6 2-amino-phenol 
• 614-80-2 2-(acetylamino)phenol 
• 106-41-2 4-bromo-phenol 
• 43192-33-2 4-bromo-2-methoxybenzaldehyde 
• 194163-04-7 4-Bromo-2-methoxymethoxy-benzoic acid ethyl ester 
• 314240-85-2 ethyl 4-bromo-2-hydroxybenzoate 
• 1666-28-0 4-bromosalicylic acid 

Downstream Products

• 127693-56-5 4-(2-Methyl-imidazo[1,2-a]pyridin-3-ylazo)-benzoic acid [1-(4-bromo-2-hydroxy-phenyl)-meth-(E)-ylidene]-hydrazide 
• 133900-95-5 1-(4-{[1-(4-Bromo-2-hydroxy-phenyl)-meth-(Z)-ylidene]-amino}-benzoyl)-1,3-dicyclohexyl-urea 
• 791068-96-7 C₁₆H₁₀O₄ 
• 888728-15-2 ethyl 4-(2-formyl-5-bromophenoxy)but-2(E)-enoate 
• 439107-94-5 6-bromo-1-benzofuran-2-carboxylic acid 
• 907945-62-4 6-bromo-2-benzofurancarboxylic acid ethyl ester 
• 1220702-33-9 3,7-dibromo-2H-chromen-2-one 
• 1210226-82-6 C₁₃H₁₃BrO₃ 
• 1282516-69-1 9-bromo-2-iodo-5,6-dihydrobenzo[f ]imidazo[1,2-d][1,4]oxazepine 
• 1282516-67-9 9-bromo-5,6-dihydrobenzo[f ]imidazo[1,2-d][1,4]oxazepine 
• 1282516-68-0 9-bromo-2,3-diiodo-5,6-dihydrobenzo[f ]imidazo[1,2-d][1,4]oxazepine 
• 1282516-74-8 9-bromo-5,6-dihydrobenzo[f]imidazo[1,2-d]-[1,4]oxazepine-2-carboxylic acid 
• 1070503-97-7 C₂₇H₃₅N₃O₆ 
• 1070503-98-8 C₂₇H₃₅N₃O₆ 

Relevant articles and documents

Expedient Approach to 6-Bromo-2-isopropylidenecoumaranone, a Potential Intermediate for the Synthesis of TMC-120B, Pseudodeflectusin, and Their Congeners

A straightforward approach toward 6-bromo-2-isopropylidenecoumaranone, a potential intermediate toward alkaloid TMC 120-B, pseudodeflectusin, and other natural products, was reported. The synthetic sequence involved the reaction of 3-bromosalicylaldehyde with chloroacetone and cyclization of the resulting ether to a 2-acetylcoumaranol intermediate. This was followed by sequential methyl Grignard addition and Jones' oxidation to the corresponding coumaranone, which was dehydrated to the final product with the methanesulfonyl chloride/pyridine reagent. The protection of the coumaranol as the corresponding THP-ether resulted in improved product yields.

Divergent Synthesis of Dihydroxanthene-Hemicyanine Fused Near-Infrared Fluorophores through the Late-Stage Amination of a Bifunctional Precursor

A late-stage amination of a bifunctional dihydroxanthene (DHX) scaffold is reported to access a wide variety of new near-infrared (NIR) chromophores/fluorophores. The divergent approach allows the coupling of aliphatic and aromatic amines and readily provides molecular diversity shedding light on the structure-fluorescence relationship of this emerging class of NIR fluorophores.

A Facile Synthesis of Ligands for the von Hippel-Lindau E3 Ligase

The proteolysis-targeting chimeras (PROTACs) have become an integral part of different stages of drug discovery. This growing field, therefore, benefits from advancements in all segments of the design of these compounds. Herein, an efficient and optimized synthetic protocol to various von Hippel-Lindau (VHL) ligands is presented, which enables easy access to multigram quantities of these essential PROTAC building blocks. Moreover, the elaborated synthesis represents a straightforward approach to further explore the chemical space of VHL ligands.

Phosphine-Catalyzed [3+2] Annulation of β-Sulfonamido-Substituted Enones with Sulfamate-Derived Cyclic Imines

Phosphine-catalyzed [3+2] annulation of β-sulfonamido-substituted enones and sulfamate-derived cyclic imines has been developed, giving a series of imidazoline derivatives in moderate to excellent yields with good to excellent diastereoselectivities. A scale-up reaction worked well under mild reaction conditions. A possible mechanism was proposed on the basis of the results obtained.

Enantioselective Construction of Tetrahydroquinazoline Motifs via Palladium-Catalyzed [4 + 2] Cycloaddition of Vinyl Benzoxazinones with Sulfamate-Derived Cyclic Imines

A palladium-catalyzed enantioselective [4 + 2] cycloaddition reaction of vinyl benzoxazinones with sulfamate-derived cyclic imines is described, affording the tetrahydroquinazolines bearing several functional rings in high yields (up to 99% yield) with good to excellent diastereoselectivities and excellent enantioselectivities (up to 96% ee). This reaction represents the first Pd-catalyzed asymmetric decarboxylative cycloaddition of vinyl benzoxazinones with imines.