6948-30-7

Basic information

• Product Name: 5-BROMOVERATRALDEHYDE
• Synonyms: 3,4-diMethyoxyl-5-broMo-benzaldehyde;5-Bromoveratraldehyde 98%;Benzaldehyde, 3-bromo-4,5-dimethoxy-;3,4-DIMETHOXY-5-BROMOBENZALDEHYDE;AKOS BBS-00008218;AKOS B004803;3-BROMO-4,5-DIMETHOXYBENZALDEHYDE;5-BROMOVERATRALDEHYDE
• CAS NO: 6948-30-7
• Molecular Formula: C₉H₉BrO₃
• Molecular Weight: 245.07
• EINECS: 230-113-2
• Product Categories: Aromatic Aldehydes & Derivatives (substituted)
• Mol File: 6948-30-7.mol
• Article Data: 53

Chemical Properties

• Melting Point: 63-64 °C(lit.)
• Boiling Point: 313.8 °C at 760 mmHg
• Flash Point: 143.6 °C
• Appearance: /
• Density: 1.482 g/cm³
• Vapor Pressure: 0.000485mmHg at 25°C
• Refractive Index: 1.567
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-BROMOVERATRALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMOVERATRALDEHYDE(6948-30-7)
• EPA Substance Registry System: 5-BROMOVERATRALDEHYDE(6948-30-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 6948-30-7(Hazardous Substances Data)

Usage

Description

5-BROMOVERATRALDEHYDE, also known as 3-Bromo-4,5-dimethoxybenzaldehyde, is an organic compound that serves as a crucial reagent in the synthesis of various compounds with potential applications in different industries. It is characterized by its unique chemical structure, which includes a bromine atom and two methoxy groups attached to a benzene ring.

Uses

Used in Pharmaceutical Industry:
5-BROMOVERATRALDEHYDE is used as a reagent for the synthesis of aromatic vinyl sulfones, which are compounds that act as inhibitors of HIV-1. This application is significant in the development of new treatments and therapies for HIV/AIDS.
Used in Natural Product Synthesis:
In the field of natural product synthesis, 5-BROMOVERATRALDEHYDE is used as a reagent to synthesize (-)-Tejedine, a secobisbenzylisoquinoline compound that naturally occurs in Barberry, a medicinal plant. This application highlights the compound's role in the development of new drugs and therapeutic agents derived from natural sources.
Used in Chemical Research:
5-BROMOVERATRALDEHYDE is also used in the preparation of 1-phenyl-2-(4-aryl-1,3,4,5-tetrahydropyrido[2,3-b][1,4]diazepin-2-ylidene)-ethanones, which are complex organic molecules with potential applications in various fields, including pharmaceuticals and materials science. This use demonstrates the versatility of 5-BROMOVERATRALDEHYDE as a reagent in chemical research and development.

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

Upstream product

• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 16414-34-9 3-bromo-4,5-dihydroxybenzaldehyde 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 121-33-5 vanillin 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 23354-30-5 3-bromo-4-methoxy-5-hydroxybenzaldehyde 
• 91-16-7 1,2-dimethoxybenzene 

Downstream Products

• 141613-46-9 1-(3-bromo-4,5-dimethoxyphenyl)ethanone 
• 52783-74-1 (3-bromo-4,5-dimethoxyphenyl)methanol 
• 54737-25-6 (E)-3-bromo-4,5-dimethoxy-1-(2-nitrovinyl)benzene 
• 854822-41-6 3,3'-dibromo-4,5,4',5'-tetramethoxy-benzil 
• 51314-72-8 5-bromo-3.4-dimethoxy-trans-cinnamic acid 
• 68278-85-3 3-bromo-4,5-dimethoxy-toluene 
• 20731-48-0 3-bromo-4,5-dimethoxybenzoic acid 
• 61203-46-1 3-bromo-4,5-dihydroxybenzoic acid 
• 70625-29-5 2,3-dibromo-4,5-dimethoxybenzaldehyde 
• 20357-26-0 3-bromo-4,5-dimethoxy-2-nitrobenzaldehyde 
• 54291-71-3 4-(5-formyl-2,3-dimethoxy-phenoxy)-benzoic acid methyl ester 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 86750-47-2 5,5'-Diformyl-2,2',3-trimethoxydiphenylether 

Relevant articles and documents

Antidiabetic activity in vitro and in vivo of BDB, a selective inhibitor of protein tyrosine phosphatase 1B, from Rhodomela confervoides

Background and Purpose: Protein tyrosine phosphatase (PTP) 1B (PTP1B) plays a critical role in the regulation of obesity, Type 2 diabetes mellitus and other metabolic diseases. However, drug candidates exhibiting PTP1B selectivity and oral bioavailability are currently lacking. Here, the enzyme inhibitory characteristics and pharmacological benefits of 3-bromo-4,5-bis(2,3-dibromo-4,5-dihydroxybenzyl)-1,2-benzenediol (BDB) were investigated in vitro and in vivo. Experimental Approach: Surface plasmon resonance (SPR) assay was performed to validate the direct binding of BDB to PTP1B, and Lineweaver–Burk analysis of the enzyme kinetics was used to characterise the inhibition by BDB. Both in vitro enzyme-inhibition assays and SPR experiments were also conducted to study the selectivity exhibited by BDB towards four other PTP-family proteins: TC-PTP, SHP-1, SHP-2, and LAR. C2C12 myotubes were used to evaluate cellular permeability to BDB. Effects of BDB on insulin signalling, hypoglycaemia and hypolipidaemia were investigated in diabetic BKS db mice, after oral gavage. The beneficial effects of BDB on pancreatic islets were examined based on insulin and/or glucagon staining. Key Results: BDB acted as a competitive inhibitor of PTP1B and demonstrated high selectivity for PTP1B among the tested PTP-family proteins. Moreover, BDB was cell-permeable and enhanced insulin signalling in C2C12 myotubes. Lastly, oral administration of BDB produced effective antidiabetic effects in spontaneously diabetic mice and markedly improved islet architecture, which was coupled with an increase in the ratio of β-cells to α-cells. Conclusion and Implications: BDB application offers a potentially practical pharmacological approach for treating Type 2 diabetes mellitus by selectively inhibiting PTP1B.

Design, synthesis and biological evaluation of bromophenol-thiazolylhydrazone hybrids inhibiting the interaction of translation initiation factors eIF4E/eIF4G as multifunctional agents for cancer treatment

The eukaryotic initiation factor 4E (eIF4E)is an emerging anticancer drug target for specific anticancer therapy as a promising approach to overcome drug resistance and promote chemotherapy antitumor efficacy. A series of bromophenol-thiazolylhydrazone hybrids were designed, synthesized and evaluated for their antitumor activities. Among of them, the most potent compound 3e (EGPI-1)could inhibit the eIF4E/eIF4G interaction. Further mechanism study demonstrated EGPI-1 played an antitumor role in multiple modes of action including regulating the activity of eIF4E by inhibiting the phosphorylation of eIF4E and 4EBP1, disrupting mitochondrial function through the mTOR/4EBP1 signaling pathway, and inducing autophagy, apoptosis and ROS generation. Moreover, EGPI-1 showed good safety and favorable pharmacokinetic properties in vivo. These observations demonstrate that EGPI-1 may serve as an excellent lead compound for the development of new anticancer drugs that target the eIF4E/eIF4G interface and as a chemical genetic probe to investigate the role of the eIF4E in biological processes and human diseases.

Full-synthetic method of racemic tetrandrine

The invention discloses a full-synthetic method of racemic tetrandrine, and belongs to the technical field of drug synthesis. The full-synthetic method of the racemic tetrandrine comprises the steps that a synthetic route adopts a convergence synthesis method, a 5-bromovanillin, namely a compound 1 and 3-hydroxy-4-methoxyphenylacetic acid, namely a compound 5 are taken as starting materials to obtain a compound 4 and a compound 6 respectively, then the compound 4 and the compound 6 are taken as raw materials to synthesize a compound 11, a compound 19 is synthesized from the compound 11, and finally, the compound 11 reacts with the compound 19. The full-synthetic method of the racemic tetrandrine has the advantages that the synthetic efficiency is higher, the yield is higher, and the cost is lower; the reaction conditions are milder, the operation is simple and convenient, the industrial value is higher, and a reference is provided for the full-synthetic method of optical voidness tetrandrine.