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
• Article Data: 8

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

Description

5-Bromo-2,4-dimethoxybenzaldehyde is an organic compound characterized by its bromine atom at the 5th position, and methoxy groups at the 2nd and 4th positions on a benzene ring. It is an important intermediate in the synthesis of various organic compounds and has potential applications in different industries due to its unique chemical properties.

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 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 6615-24-3 2-hydroxy-4-methoxy-5-nitrobenzaldehyde 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 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 

Downstream Products

• 82040-68-4 (E)-5-bromo-2,4-dimethoxy-β-nitrostyrene 
• 24988-36-1 4,6-dibromo-1,3-dimethoxybenzene 
• 32246-20-1 5-bromo-2,4-dimethoxybenzoic acid 
• 33084-03-6 2,4-Dimethoxy-5-brom-4'-cyan-chalkon 
• 33083-95-3 2,4-Dimethoxy-5-brom-3'-cyan-chalkon 
• 131509-74-5 1S,5R,1'S-1-(5-bromo-2,4-dimethoxyphenyl)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ene)ethanol 
• 131509-83-6 1S,5R,1'R-1-(5-bromo-2,4-dimethoxyphenyl)-2-(6,6-dimethylbicyclo<3.1.1>hept-2-ene)ethanol 
• 19345-87-0 1-Bromo-2,4-dimethoxy-5-methylbenzene 
• 154377-22-7 5-bromo-2,4-dimethoxyphenol 
• 37162-75-7 1-Bromo-2,4-dimethoxy-5-((E)-2-nitro-propenyl)-benzene 
• 181819-62-5 5-bromo-2,4-dimethoxybenzyl alcohol 
• 383175-97-1 5-(benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde 
• 19676-63-2 5-ethyl-2,4-dimethoxy-benzaldehyde 
• 552845-81-5 2,4-dimethoxy-5-(5-methyl-thien-2-yl)-benzaldehyde 

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.

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.

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.