34841-06-0

Basic information

• Product Name: 3-Bromo-4-methoxybenzaldehyde
• Synonyms: Benzaldehyde, 3-bromo-4-methoxy-;p-Anisaldehyde, 3-bromo-;AKOS BBS-00003260;AKOS B004285;3-BROMO-4-METHOXYBENZALDEHYDE;3-BROMO-P-ANISALDEHYDE;ASISCHEM N43045;OTAVA-BB BB0125160184
• CAS NO: 34841-06-0
• Molecular Formula: C₈H₇BrO₂
• Molecular Weight: 215.04
• EINECS: 252-241-8
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Adehydes, Acetals & Ketones;Anisoles, Alkyloxy Compounds & Phenylacetates;Bromine Compounds;Aldehydes;Building Blocks;C8;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 34841-06-0.mol
• Article Data: 38

Chemical Properties

• Melting Point: 51-54 °C(lit.)
• Boiling Point: 108-110°C 1mm
• Flash Point: 108-110°C/1mm
• Appearance: white to beige solid
• Density: 1.5313 (rough estimate)
• Vapor Pressure: 0.00208mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform, DMSO, Ethyl Acetate
• Sensitive: Air Sensitive
• BRN: 1636939
• CAS DataBase Reference: 3-Bromo-4-methoxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-4-methoxybenzaldehyde(34841-06-0)
• EPA Substance Registry System: 3-Bromo-4-methoxybenzaldehyde(34841-06-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26
• WGK Germany: 3
• HazardClass: IRRITANT, AIR SENSITIVE
• Hazardous Substances Data: 34841-06-0(Hazardous Substances Data)

Usage

Description

3-Bromo-4-methoxybenzaldehyde is an organic compound derived from the solvent-free bromination of 4-methoxybenzaldehyde using 1,3-di-n-butylimidazolium tribromide as a brominating reagent. It is a valuable intermediate in the synthesis of various complex organic molecules and has potential applications in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
3-Bromo-4-methoxybenzaldehyde is used as a key intermediate for the asymmetric synthesis of novel β-hydroxy-α-amino acid derivatives, which are important in the development of new drugs and therapeutic agents. It plays a crucial role in the Mukaiyama aldol reaction, a widely used method for the formation of carbon-carbon bonds in organic chemistry.
Used in Chemical Synthesis:
3-Bromo-4-methoxybenzaldehyde is used as a starting reagent for the synthesis of various complex organic molecules, such as 2-(3-bromo-4-methoxyphenyl)-5-fluorobenzothiazole, 5-[(Z)-2-(3-bromo-4-methoxyphenyl)vinyl]-1,2,3-trimethoxybenzene, and (2E)-3-(3-bromo-4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one. These compounds have potential applications in various fields, including materials science, pharmaceuticals, and agrochemicals.
Used in Total Synthesis:
3-Bromo-4-methoxybenzaldehyde is also employed in the total synthesis of complex natural products, such as engelhardione, which is a bioactive compound with potential applications in the pharmaceutical industry. 3-Bromo-4-methoxybenzaldehyde serves as a versatile building block for the construction of diverse molecular frameworks and scaffolds.

Synthesis Reference(s)

Tetrahedron, 41, p. 2903, 1985 DOI: 10.1016/S0040-4020(01)96614-1

InChI:InChI=1/C8H7BrO2/c1-11-8-3-2-6(5-10)4-7(8)9/h2-5H,1H3

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 186581-53-3 diazomethane 
• 82906-07-8 2-bromo-4-dibromomethylphenol 
• 82894-82-4 2-bromo-4-(dibromomethyl)anisole 
• 101538-30-1 2-bromo-1-methoxy-4-propylbenzene 
• 35103-34-5 N-(p-methoxybenzyl)acetamide 
• 2973-78-6 3-bromo-4-hydroxybenzylaldehyde 
• 74-88-4 methyl iodide 
• 6258-60-2 p-methoxybenzylmercaptan 
• 105-13-5 4-Methoxybenzyl alcohol 
• 6399-81-1 triphenylphosphine hydrobromide 
• 223418-72-2 2-(3-bromo-4-methoxyphenyl)-1,3-dioxolane 
• 99-96-7 4-hydroxy-benzoic acid 
• 121-98-2 methyl 4-methoxybenzoate 

Downstream Products

• 41001-29-0 (3-bromo-4-methoxy-benzyliden)-aniline 
• 29973-99-7 4-(3-bromo-4-methoxy-benzylidene)-2-phenyl-4H-oxazol-5-one 
• 102151-29-1 2-(3-bromo-4-methoxyphenyl)-4-methylimidazole 
• 21962-50-5 5-formyl-2-methoxybenzonitrile 
• 1027513-90-1 (3-bromo-4-methoxyphenyl)(phenyl)methane 
• 34039-30-0 2-bromo-1-methoxy-4-vinylbenzene 
• 1331560-65-6 (E)-4-(3-Bromo-4-methoxy-phenyl)-but-3-en-2-one 
• 125872-38-0 3-carbamoyl-4-methoxy-benzaldehyde 
• 76143-20-9 5-formyl-2-hydroxy-benzamide 
• 269411-78-1 2-benzyloxy-5-formyl-benzamide 

Relevant articles and documents

Decarboxylative Generation of 2-Azaallyl Anions: 2-Iminoalcohols via a Decarboxylative Erlenmeyer Reaction

Condensation between the tetrabutylammonium salt of 2,2-diphenylglycine and aldehydes results in a decarboxylative Erlenmeyer reaction, affording 1,2-diaryl-2-iminoalcohols as a mixture of diastereomers in good yields. The diastereomeric ratio shifts over time, with the anti diastereomer and the syn oxazolidine tautomer serving as the kinetic and thermodynamic products, respectively. Addition of Lewis acids can catalyze the rates of reaction and product equilibration. The results highlight the stereochemical promiscuity of 1,2-diaryl-2-iminoalcohols in the presence of Lewis acids and Bronsted bases. (Chemical Presented).

Electricity Driven 1,3-Oxohydroxylation of Donor-Acceptor Cyclopropanes: a Mild and Straightforward Access to β-Hydroxy Ketones

An unprecedented external oxidant-free electrochemical protocol for 1, 3-oxohydroxylation of donor-acceptor cyclopropane is disclosed. The strategy encompasses the activation of the labile π-electron cloud of the aryl ring to cleave the strained Csp3?Csp3 bond of cyclopropane to afford the β-hydroxy ketones via insertion of molecular oxygen. More significantly, based on the detailed mechanistic investigations and cyclic voltammetry experiments, a plausible mechanism is proposed.

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.

Linear diarylheptanoids as potential anticancer therapeutics: synthesis, biological evaluation, and structure–activity relationship studies

In efforts to develop effective anticancer therapeutics with greater selectivity toward cancerous cell and reduced side-effects, such as emetic effects due to detrimental action of the drug toward the intestinal flora, a series of linear diarylheptanoids (LDHs) were designed and synthesized in 7 steps with good-to-moderate yields. All synthesized compounds were evaluated for their antibacterial, antiproliferative, and topoisomerase-I and -IIα inhibitory activity. Overall, all compounds showed little to no activity against the bacterial strains tested. Most of the synthesized compounds showed good antiproliferative activity against human breast cancer cell lines (T47D); specifically, the IC50 values of compounds 6a, 6d, 7j, and 7e were 0.09, 0.64, 0.67, and 0.99 μM, respectively. Among the tested compounds, 7b inhibited topo-I by 9.3% (camptothecin 68.8%), 7e and 7h inhibited topo-IIα by 38.4 and 47.4% (etoposide 76.9%), respectively, at the concentration of 100 μM. These results suggest that a set of promising anticancer agents can be obtained by reducing inhibitory actions on different microbes to provide enhanced selectivity against cancerous cells.