2973-78-6

Basic information

• Product Name: 3-BROMO-4-HYDROXYBENZALDEHYDE
• Synonyms: 3-BROMO-4-HYROXYBENZALDEHYDE;3-BROMO-4-HYDROXYBENZALDEHYDE;AKOS B029029;ASISCHEM N48923;4-Hydroxy-3-bromobenzaldehyde;3-Bromo-4-hydroxybenzaldehyde, 98+%;3-Bromo-4-hydroxybenzaldehyde, 97+%;2-Bromo-4-formylphenol
• CAS NO: 2973-78-6
• Molecular Formula: C₇H₅BrO₂
• Molecular Weight: 201.02
• EINECS: -0
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Adehydes, Acetals & Ketones;Bromine Compounds;Phenols;Aldehydes;C7;Carbonyl Compounds
• Mol File: 2973-78-6.mol
• Article Data: 56

Chemical Properties

• Melting Point: 130-135 °C(lit.)
• Boiling Point: 261.252 °C at 760 mmHg
• Flash Point: 111.802 °C
• Appearance: /
• Density: 1.737 g/cm³
• Vapor Pressure: 0.00718mmHg at 25°C
• Refractive Index: 1.657
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 6.24±0.18(Predicted)
• Water Solubility: Soluble in water 1.33 g/L.
• Sensitive: Air Sensitive
• BRN: 2205318
• CAS DataBase Reference: 3-BROMO-4-HYDROXYBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-4-HYDROXYBENZALDEHYDE(2973-78-6)
• EPA Substance Registry System: 3-BROMO-4-HYDROXYBENZALDEHYDE(2973-78-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 2973-78-6(Hazardous Substances Data)

Usage

Uses

3-Bromo-4-hydroxybenzaldehyde is an intermediate in organic syntheses, it is used to produce other chemicals like 5-Brom-4-hydroxy-b-nitrostyrol.

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

Upstream product

• 50-00-0 formaldehyd 
• 95-56-7 2-hydroxybromobenzene 
• 67-66-3 chloroform 
• 75-25-2 Bromoform 
• 7726-95-6 bromine 
• 123-08-0 4-hydroxy-benzaldehyde 
• 34841-06-0 3-bromo-4-methoxybenzylaldehyde 
• 6627-55-0 2-bromo-p-cresol 
• 107-21-1 ethylene glycol 
• 67-56-1 methanol 
• 106-44-5 p-cresol 
• 7465-16-9 p-hydroxybenzaldehyde diethyl acetal 
• 162269-90-1 3-bromo-4-(methoxymethoxy)benzaldehyde 
• 29922-56-3 2-bromo-4-(hydroxymethyl)phenol 

Downstream Products

• 69455-12-5 4-benzyloxy-3-bromobenzaldehyde 
• 937678-86-9 4-(4-methoxybenzyloxy)-3-bromobenzaldehyde 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 99-96-7 4-hydroxy-benzoic acid 
• 162269-90-1 3-bromo-4-(methoxymethoxy)benzaldehyde 
• 882687-25-4 3-[4-(3-benzyloxycarbonylaminopropoxy)-3-bromophenyl]-2-(4-methoxybenzyloxyimino)propanoic acid 
• 882687-16-3 methyl 3-[4-(3-benzyloxycarbonylaminopropoxy)-3-bromophenyl]-2-(4-methoxybenzyloxyimino)propanoate 

Relevant articles and documents

Solvolytic Elimination and Hydrolysis promoted by an Aromatic Hydroxy-group. Part 2. The Hydrolysis of 2-Bromo-4-dibromomethylphenol in 95percent 1,4-Dioxane

The reaction of 2-bromo-4-dibromomethylphenol with water in slightly aqueous (95percent) 1,4-dioxane has been examined kinetically by using u.v. spectroscopy, which provides evidence for the transient formation of the quinone methide, 2-bromo-4-bromomethylenecyclohexa-2,5-dienone, during the hydrolysis.The final product is 3-bromo-4-hydroxybenzaldehyde.The rate of disappearance of starting material is independent of acidity, but is reduced by added or developing bromide ion.The rate of the loss of bromide ion from the phenol is very much greater than that of the corresponding reaction of 2-bromo-4-dibromomethylanisole under the same conditions.An estimate of the value of ?p-OH+ (-1.36), made by using these relative rates, is larger than the value (-0.92) based on relative rates of aromatic electrophilic substitution.Solvent kinetic isotope effects on these reactions are reported; the theoretical implications of variation in the substituent parameter for the hydroxy-group is discussed in terms of solvent effects on H-O hyperconjugation.

Ni-NiO heterojunctions: a versatile nanocatalyst for regioselective halogenation and oxidative esterification of aromatics

Herein, we report a facile method for the synthesis of Ni-NiO heterojunction nanoparticles, which we utilized for the nuclear halogenation reaction of phenol and substituted phenols usingN-bromosuccinimide (NBS). A remarkablepara-selectivity was achieved for the halogenated products under semi-aqueous conditions. Interestingly, blocking of thepara-position of phenol offeredortho-selective halogenation. In addition, the Ni-NiO nanoparticles catalyzed the oxidative esterification of carbonyl compounds with alcohol, diol or dithiol in the presence of a catalytic amount of NBS. It was observed that the aromatic carbonyls substituted with an electron-donating group favoured nuclear halogenation, whereas an electron-withdrawing group substitution in carbonyl compounds facilitated the oxidation reaction. In addition, the catalyst was magnetically separated and recycled 10 times. The tuned electronic structure at the Ni-NiO heterojunction controlled selectivity and activity as no suchpara-selectivity was observed with commercially available NiO or Ni nanoparticles.

Structure-Activity-Relationship-Aided Design and Synthesis of xCT Antiporter Inhibitors

The xCT antiporter is a cell membrane protein involved in active counter-transportation of glutamate (outflux) with cystine (influx) over the human cell membrane. This feature makes the xCT antiporter a crucial element of the biosynthesis of the vital free radical scavenger glutathione. The prodrug sulfasalazine, a medication for the treatment of ulcerative colitis, was previously proven to inhibit the xCT antiporter. Starting from sulfasalazine, a molecular scaffold jumping followed by SAR-assisted design and synthesis provided a series of styryl hydroxy-benzoic acid analogues that were biologically tested in vitro for their ability to decrease intracellular glutathione levels using four different cancer cell lines: A172 (glioma), A375 (melanoma), U87 (glioma) and MCF7 (breast carcinoma). Depletion of glutathione levels varied among the compounds as well as among the cell lines. Flow cytometry using propidium iodide and the annexin V marker demonstrated minimal toxicity in normal human astrocytes for a promising candidate molecule (E)-5-(2-([1,1′-biphenyl]-4-yl)vinyl)-2-hydroxybenzoic acid.

Preparation method of 3-bromo-4-hydroxybenzaldehyde

The invention discloses a preparation method of 3-bromo-4-hydroxybenzaldehyde. The preparation method comprises the following steps: (1) carrying out a bromination reaction on p-hydroxybenzene methylal and bromine to obtain 3-bromo-4-hydroxybenzene methylal; and (2) carrying out a hydrolysis reaction on the 3-bromo-4-hydroxybenzene methylal obtained in the step (1), and carrying out post-treatmentafter the reaction is finished to obtain the 3-bromo-4-hydroxybenzaldehyde. According to the preparation method, aldehyde is replaced with acetal for the bromination reaction, so that generation of adibromo product is effectively avoided, the yield and purity of a monobromo product are improved, and industrialization is facilitated.