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

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

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 
• 67-56-1 methanol 
• 105-13-5 4-Methoxybenzyl alcohol 
• 104-46-1 anethole 
• 2973-78-6 3-bromo-4-hydroxybenzylaldehyde 
• 77-78-1 dimethyl sulfate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 38493-59-3 (3-bromo-4-methoxy-phenyl)-methanol 
• 35450-37-4 methyl 3-bromo-4-methoxybenzoate 

Downstream Products

• 171917-89-8 5,5'-diformyl-2,2'-dimethoxydiphenyl ether 
• 70400-19-0 (E)-2-bromo-1-methoxy-4-(2-nitrovinyl)benzene 
• 1080-07-5 (E)-3-(3-bromo-4-methoxy-phenyl)prop-2-enoic acid 
• 110050-68-5 1-(4-bromo-1-hydroxy-[2]naphthyl)-3t-(3-bromo-4-methoxy-phenyl)-propenone 
• 109251-45-8 3-bromo-2'-hydroxy-4-methoxy-3'-methyl-5'-nitro-trans-chalcone 
• 37864-65-6 (3-bromo-4-methoxyphenyl)(phenyl)methanol 
• 38493-59-3 (3-bromo-4-methoxy-phenyl)-methanol 
• 41001-29-0 (3-bromo-4-methoxy-benzyliden)-aniline 
• 32045-83-3 3-bromo-4-methoxy-4'-methyl-trans-chalcone 
• 29973-99-7 4-(3-bromo-4-methoxy-benzylidene)-2-phenyl-4H-oxazol-5-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 258267-66-2 2-(3-bromo-4-methoxyphenyl)oxirane 
• 139962-92-8 3-Bromo-4-methoxybenzaldehyde diethyl acetal 
• 918492-64-5 (3-bromo-4-methoxyphenyl)-methylidene(2,2-dimethoxyethyl)amine 

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).

Aggregation-induced emission enhancement in halochalcones

A family of push-pull fluorophores, consisting of a chalcone core decorated with electron-donating substituents and halogen atoms, was designed and synthesized. Luminescence studies were performed in solution, aggregate form and in the solid state. Although some compounds are only weakly fluorescent in solution, all are emissive in the solid state showing aggregation-induced emission enhancement. In the crystalline state, the halogen atoms are not involved in halogen bonds but their presence strongly influences the aggregation-induced emission properties of the fluorophores.

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.

Dehydroxymethyl Bromination of Alkoxybenzyl Alcohols by Using a Hypervalent Iodine Reagent and Lithium Bromide

We describe the dehydroxymethylbromination of alkoxybenzyl alcohol by using a hypervalent iodine reagent and lithium bromide in F 3 CCH 2 OH at room temperature. Selective monobromination or dibromination was possible by adjusting the molar ratios of hypervalent iodine reagent and lithium bromide.

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.

Mechanistic study on iodine-catalyzed aromatic bromination of aryl ethers by N-Bromosuccinimide

Although iodine-catalyzed reaction has rapid advances in recent years, examples on iodine-catalyzed bromination are rare and the mechanism of these reactions remains unclear. Herein, we reported an I2-catalyzed aromatic bromination of aryl ethers by NBS and presented the details of the mechanistic study including kinetic study and the study of kinetic isotope effects. The study revealed that the reaction was actually catalyzed by IBr formed in the induction period, and the rate-determining step was the HBr-elimination of the Wheland intermediate assisted by IBr.

Regioselective monobromination of aromatics via a halogen bond acceptor-donor interaction of catalytic thioamide and N-bromosuccinimide

Regioselective monobromination of various aromatics was achieved at room temperature using N-bromosuccinimide and 5 mol% of thioamides in acetonitrile. With thiourea as catalyst, activated aromatics, such as anisole, acetanilide, benzamide and phenol analogues containing electron donating or withdrawing groups, were brominated with high regioselectivity. Room temperature brominations of weakly activated aromatics and deactivated 9-fluorenone were accomplished by 5 mol% thioacetamide, higher substrates concentrations and longer reaction times. A backbonding of the bromine lone pairs with the π*of C[dbnd]S group and a halogen bond between the halogen bond donor bromine and the halogen bond acceptor sulfur of the thioamide are thought to be the principal interactions and cause of N-bromosuccinimide activation.

Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions

An environmentally benign, metal-free synthesis of sulfonyl chlorides and bromides from thiols in the presence of ammonium nitrate, an aqueous solution of HCl and HBr and oxygen as a terminal oxidant was developed. The reactivity of various substituted thiophenols, benzylic-, aliphatic- and heteroaromatic thiols was examined. Ammonium nitrate served as a source of nitrogen oxides (NO/NO2), which are the crucial players in a redox-catalytic cycle. Sulfonyl chlorides and bromides were isolated without extraction and "filtered" over a short pad of silica gel; the use of solvents was greatly reduced in comparison with traditional isolation and purification. A "one-pot" protocol for the conversion of thiol into sulfonamide is also demonstrated. Scale-up experiments on the preparation of sulfonyl chloride and bromide are shown. A possible reaction pathway is discussed.

Novel synthetic process of isovanillin

The invention discloses a novel synthetic process of isovanillin, and relates to the field of organic synthesis technology. The method comprises: reacting 4-hydroxybenzaldehyde as a raw material with bromine to obtain 3-bromo 4-hydroxybenzaldehyde, reacting with methyl iodide to obtain 3-bromo-4-methoxy benzaldehyde, and then performing hydrolysis to obtain the isovanillin under the action of sodium hydroxide and cuprous chloride. The method adopts cheap and easily obtained 4-hydroxybenzaldehyde as the starting material, the isovanillin is obtained under mild reaction conditions, and the economic efficiency of a process is improved while the cost is reduced. The total yield of the product, isovanillin, obtained by using the optimum process is up to 64.1%, the conversion rates of the raw materials in each step are significantly increased, and the method is suitable for industrial production.