130333-46-9

Basic information

• Product Name: 5-BROMO-2,4-DIMETHOXYBENZALDEHYDE
• Synonyms: 292516_ALDRICH;InChI=1/C9H9BrO3/c1-12-8-4-9(13-2)7(10)3-6(8)5-11/h3-5H,1-2H;SBB000845;ZINC00028461;TIMTEC-BB SBB000845;ASISCHEM R31004;5-BROMO-2,4-DIMETHOXYBENZALDEHYDE;benzaldehyde, 5-bromo-2,4-dimethoxy-
• CAS NO: 130333-46-9
• Molecular Formula: C₉H₉BrO₃
• Molecular Weight: 245.07
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;C9;Carbonyl Compounds
• Mol File: 130333-46-9.mol

Chemical Properties

• Melting Point: 140-141 °C(lit.)
• Boiling Point: 344.3°Cat760mmHg
• Flash Point: 162°C
• Appearance: /
• Density: 1.482g/cm³
• Vapor Pressure: 6.64E-05mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: 5-BROMO-2,4-DIMETHOXYBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2,4-DIMETHOXYBENZALDEHYDE(130333-46-9)
• EPA Substance Registry System: 5-BROMO-2,4-DIMETHOXYBENZALDEHYDE(130333-46-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 130333-46-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-2,4-dimethoxybenzaldehyde is used as a key intermediate for the synthesis of 1,2-dihydro-4,6-dimethoxy-3-methylbenzocyclobuten-1-ol, which may have potential applications in the development of pharmaceutical compounds. Its unique structure allows for further chemical modifications and the creation of new molecules with specific therapeutic properties.
Used in Chemical Synthesis:
In the field of organic chemistry, 5-Bromo-2,4-dimethoxybenzaldehyde is used as a starting material for the preparation of various complex organic molecules. For example, it undergoes coupling with benzo[b]thiophene-2-boronic acid in the presence of tetrakis(triphenylphosphine)palladium(0) to give 5-(benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde. 5-BROMO-2,4-DIMETHOXYBENZALDEHYDE can be further utilized in the synthesis of other organic compounds with potential applications in various industries.
While the provided materials do not explicitly mention other industries or applications, it is worth noting that 5-Bromo-2,4-dimethoxybenzaldehyde, due to its unique structure and reactivity, may have potential uses in other areas such as materials science, agrochemicals, or even as a precursor to dyes and pigments. Further research and development could reveal additional applications for this versatile compound.

InChI:InChI=1/C9H9BrO3/c1-12-8-4-9(13-2)7(10)3-6(8)5-11/h3-5H,1-2H3

Upstream product

• 42174-73-2 (E)-2,4-dimethoxycinnamic acid ethyl ester 
• 57543-36-9 5-bromo-2-hydroxy-4-methoxybenzaldehyde 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 7726-95-6 bromine 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 6615-24-3 2-hydroxy-4-methoxy-5-nitrobenzaldehyde 
• 116096-90-3 5-bromo-2,4-dihydroxy-benzaldehyde 
• 1227484-18-5 5-bromo-2-hydroxy-4-(methoxymethoxy)benzaldehyde 
• 1227484-24-3 5-bromo-2-methoxy-4-(methoxymethoxy)benzaldehyde 
• 552845-88-2 5-bromo-4-hydroxy-2-methoxy-benzaldehyde 
• 74-88-4 methyl iodide 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 

Downstream Products

• 82040-68-4 (E)-5-bromo-2,4-dimethoxy-β-nitrostyrene 
• 181819-62-5 5-bromo-2,4-dimethoxybenzyl alcohol 
• 24988-36-1 4,6-dibromo-1,3-dimethoxybenzene 
• 32246-20-1 5-bromo-2,4-dimethoxybenzoic acid 
• 383175-97-1 5-(benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde 
• 1620146-40-8 (Z)-5-(5-bromo-2, 4-dimethoxybenzylidene)thiazolidine-2,4-dione 
• 1620146-45-3 (Z)-5-(5-bromo-2, 4-dimethoxybenzylidene)-3-methylthiazolidine-2,4-dione 
• 1400303-66-3 4-(5-formyl-2,4-dimethoxyphenyl)-2-isopropyl-1,2-dimethyl-5-oxo-2,5-dihydro-1H-imidazole 3-oxide 
• 882662-13-7 1-bromo-5-(4-ethylbenzyl)-2,4-dimethoxybenzene 
• 1201649-41-3 1-(5-bromo-2,4-dimethoxyphenylmethylene)indene-3-carbaldehyde 
• 1091618-42-6 C₁₁H₁₀BrNO₃ 
• 154377-23-8 2-methoxy-5-<(phenylmethyl)amino>cyclohexa-2,5-diene-1,4-dione 
• 154377-14-7 2-amino-5-methoxycyclohexa-2,5-diene-1,4-dione 

Relevant articles and documents

Intermolecular Aryl C?H Amination through Sequential Iron and Copper Catalysis

A mild, efficient and regioselective method for para-amination of activated arenes has been developed through a combination of iron and copper catalysis. A diverse range of products were obtained from an operationally simple one-pot, two-step procedure involving bromination of the aryl substrate with the powerful Lewis acid iron(III) triflimide, followed by a copper(I)-catalysed N-arylation reaction. This two-step dehydrogenative process for the regioselective coupling of aromatic C?H bonds with non-activated amines was applicable to anisole-, phenol-, aniline- and acetanilide-type aryl compounds. Importantly, the arene substrates were used as the limiting reagent and required no protecting-group manipulations during the transformation.

Design, synthesis and docking study of 5-(substituted benzylidene) thiazolidine-2,4-dione derivatives as inhibitors of protein tyrosine phosphatase 1B

A series of novel 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives was designed, and synthesized based on our previous studies. Also their activities were evaluated as competitive inhibitors of protein tyrosine phosphatase 1B (PTP1B). Compounds 6d-6g, 7b, 7c, 7e, 7j, 7k, 7m, 14b and 14e-14f showed potent inhibitory effects against PTP1B, and compound 7e, the most potent among the series, had an IC50 of 4.6 μM. Also a Surflex-Dock docking model of 7e was studied. Compound 7e showed a negative binding energy of -7.35 kcal/mol and a high affinity to PTP1B residues (Gly220, Ala217, Arg221, Asp181, Ser216, Cys215, Phe182, Gln262 and Ile219) in the active sites, indicating that it may stabilize the open form and generate tighter binding to the catalytic sites of PTP1B.

Dicarbaporphyrinoid systems. Synthesis of oxo-adj-dibenziphlorins

A series of diformylbenzophenones were generated by sequentially reacting protected bromobenzaldehydes with n-butyllithium and ethyl N,N- dimethylcarbamate. The acetal protective groups were cleaved with refluxing formic acid. Vilsmeier-Haack formylation of 2,2′,4,4′- tetramethoxybenzophenone also afforded a related dialdehyde. MacDonald "2 + 2" condensation of three benzophenone dialdehydes with a dipyrrylmethane gave oxophlorin analogues constructed from two benzene and two pyrrole rings. The free base oxodibenziphlorins were rather unstable in solution, and in most cases these porphyrinoids were isolated as the corresponding trifluoroacetate salts. The spectroscopic properties of 6-oxo-adj-dibenziphlorins are consistent with a nonaromatic ring system. DFT calculations indicated that the macrocycles considerably diverge from planarity, particularly when methoxy substituents are present on the arene rings.

Antiangiogenic versus cytotoxic activity in analogues of aeroplysinin-1

A series of analogues of the potentially angiogenic inhibitor aeroplysinin-1 1 were synthesized and their in vitro antiangiogenic and cytotoxic activities evaluated. In the case of epoxy ketone 6 and azlactone 36 the relationship sprouting inhibition assay/cytotoxicity in BAE cells was enhanced by one order and two orders of magnitude, respectively, with respect to the reference. These results imply more specific antiangiogenic properties for the synthesized derivatives.

Pyridinium hydrobromide perbromide induces ipsobromodeformylation in o-hydroxy and o-methoxy substituted aromatic aldehydes

The reaction of o-hydroxy and o-methoxy substituted aromatic aldehydes with PHPB in pyridine gives aromatic bromination products including those arising from ipsobromodeformylation.

Solid state nuclear bromination with N-bromosuccinimide. Part 2. Experimental and theoretical studies of reactions with some substituted benzaldehydes

N-Bromosuccinimide reacts with aromatic aldehydes in the solid state to yield exclusively nuclear brominated products while a similar reaction in the solution phase produces a number of products under varied conditions. The reactivity and regioselectivity have been studied in terms of the energies of HOMO, HOMO-LUMO difference, reaction free energy, reaction conditions and crystal packing. Single crystal X-ray structural analysis of 3,4-dihydroxybenzaldehyde has been carried out. Crystal packing energies of some of the reactive and unreactive benzaldehydes indicate the importance of molecular bromine diffusion in the solid state.

The Bromination of Phenolic Methyl Ethers with Hydrogen Bromide using Sodium Tungstate and Hydrogen Peroxide as Oxidant

Sodium tungstate has been found to be an effective catalyst for the nuclear bromination of some aromatic methyl ethers using hydrogen bromide in glacial acetic acid and hydrogen peroxide as the oxidant.