60632-40-8

Basic information

• Product Name: 6-Bromovanillin
• Synonyms: 6-BROMOVANILLIN;AKOS B004167;2-BROMO-4-HYDROXY-5-METHOXYBENZALDEHYDE;ART-CHEM-BB B004167;CHEMBRDG-BB 3004167;6-BROMOVANILLIN/2-BROMO-4-HYDROXY-5-METHOXYBENZALDEHYDE;2-bromo-4-hydroxy-5-methoxybenzaldehyde(SALTDATA: FREE);Vanillin, 6-bromo-
• CAS NO: 60632-40-8
• Molecular Formula: C₈H₇BrO₃
• Molecular Weight: 231.04
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);API intermediates
• Mol File: 60632-40-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 178 °C
• Boiling Point: 326.2 °C at 760 mmHg
• Flash Point: 151.1 °C
• Appearance: /
• Density: 1.653 g/cm³
• Vapor Pressure: 0.000115mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform, DCM, Ethyl Acetate
• PKA: 6.83±0.23(Predicted)
• CAS DataBase Reference: 6-Bromovanillin(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromovanillin(60632-40-8)
• EPA Substance Registry System: 6-Bromovanillin(60632-40-8)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 60632-40-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Bromovanillin is used as a key intermediate in the synthesis of Carbidopa (C175915), a pharmaceutical compound that functions as an inhibitor of aromatic amino acid decarboxylase. This enzyme inhibition is crucial for the treatment of Parkinson's disease and other movement disorders, as it helps regulate the levels of neurotransmitters in the brain, thereby alleviating symptoms associated with these conditions.
In the synthesis process, 6-Bromovanillin serves as a valuable building block, providing a platform for further chemical modifications and the development of new therapeutic agents. Its unique reactivity and structural features make it an essential component in the creation of novel drugs and pharmaceutical formulations.

InChI:InChI=1/C8H7BrO3/c1-12-8-2-5(4-10)6(9)3-7(8)11/h2-4,11H,1H3

Upstream product

• 881-68-5 vanillin acetate 
• 7726-95-6 bromine 
• 7553-56-2 iodine 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 121-33-5 vanillin 
• 69404-94-0 O-tert-butyldimethylsilylvanillin 
• 52783-67-2 2-bromo-4-hydroxy-5-methoxybenzyl alcohol 
• 52783-83-2 4-acetoxy-2-bromo-5-methoxybenzaldehyde 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 

Downstream Products

• 2973-75-3 5,6-dibromo-4-hydroxy-3-methoxybenzaldehyde 
• 90004-83-4 2-bromo-3-chloro-4-hydroxy-5-methoxy-benzaldehyde 
• 486994-01-8 4-benzoyloxy-2-bromo-5-methoxy-benzaldehyde 
• 40705-22-4 4-benzyloxy-6-bromo-3-methoxybenzaldehyde 
• 1350809-54-9 5-methoxy-2-methyl-4-[(4-nitrophenyl)methoxy]benzaldehyde 
• 1350809-53-8 2-ethenyl-5-methoxy-4-[(4-nitrophenyl)methoxy]benzaldehyde 
• 1350809-55-0 2-ethyl-5-methoxy-4-[(4-nitrophenyl)methoxy]benzaldehyde 
• 864717-15-7 2-bromo-5-methoxy-4-[(4-nitrophenyl)methoxy]benzaldehyde 
• 1271303-89-9 (Z)-α-(2'-bromo-4'-hydroxy-5'-methoxyphenyl)-N-benzylnitrone 
• 23149-38-4 1,3,4-triacetoxy-2-bromo-5-methoxybenzene 
• 23030-67-3 1,2,5-triacetoxy-3-methoxy-benzene 
• 214848-02-9 4-benzyloxy-2-bromo-5-methoxybenzoic acid 
• 512827-07-5 2,3-dibromo-4-hydroxy-5-methoxy-benzaldehyde-oxime 

Relevant articles and documents

Convergent First Total Synthesis of Melovinone: A Densely Substituted 3-Methoxy-4-quinolone Isolated from Melochia tomentosa L

The first total synthesis of melovinone, a nonrutaceous 3-methoxy-4-quinolone alkaloid isolated from Melochia tomentosa L., is reported. The target was acquired in a convergent fashion through the Suzuki-Miyaura cross-coupling reaction between an ortho-nitrobenzoic acid acetonyl ester derivative prepared from vanillin and potassium 5-phenyl-1-pentyltrifluoroborate, obtained from β-phenethyl bromide. The coupling was followed by a chemoselective reduction of the nitro group and a microwave-Assisted and AcOH-promoted cyclization with rearrangement of the resulting acetonyl anthranilate. This afforded a pseudane intermediate, which was selectively methylated on the 3-OH. The synthetic pathway enabled to reach the objective in 11 steps and 18% overall yield. The 1 H NMR spectra of the synthetic and natural product were in full agreement.

cGAS ANTAGONIST COMPOUNDS

Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.

Structure and biological evaluation of (E)-5-bromo-2-methoxy-4-((phenylimino)methyl)phenol derivatives as antibacterial agents

Three (E)-5-bromo-2-methoxy-4-((phenylimino)methyl)phenol derivatives (1-3) are synthesized and characterized by elemental analysis and single-crystal X-ray diffraction. The antibacterial activities of compounds 1-3 against Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, and Staphylococcus aureus are evaluated by the MTT method.

Exploring the formation and recognition of an important G-quadruplex in a HIF1α promoter and its transcriptional inhibition by a benzo[c]phenanthridine derivative

Four putative G-quadruplex sequences (PGSs) in the HIF1α promoter and the 5′UTR were evaluated for their G-quadruplex-forming potential using ESI-MS, CD, FRET, DMS footprinting, and a polymerase stop assay. An important G-quadruplex (S1) has been proven to inhibit HIF1α transcription by blocking AP2 binding. A benzo[c]phenanthridine derivative was found to target the S1 G-quadruplex and induce its conformational conversion from antiparallel to parallel orientation. The transcriptional suppression of HIF1α by this compound was demonstrated using western blotting, Q-RT-PCR, luciferase assay, and ChIP. Our new findings provided a novel strategy for HIF1α regulation and potential insight for cancer therapy.

PROPHYLACTIC OR THERAPEUTIC AGENT FOR CANCER

A compound represented by the formula (I): wherein each symbol is as described in the specification, or a salt thereof has a superior activity as an estrogen-related receptor-α modulator, and is useful as a prophylactic or therapeutic agent for cancer.

A new method for induced fit docking (genius) and its application to virtual screening of novel HCV NS3-4A protease inhibitors

Hepatitis C virus (HCV) is an etiologic agent of chronic liver disease, and approximately 170 million people worldwide are infected with the virus. HCV NS3-4A serine protease is essential for the replication of this virus, and thus has been investigated as an attractive target for anti-HCV drugs. In this study, we developed our new induced-fit docking program (genius), and applied it to the discovery of a new class of NS3-4A protease inhibitors (IC50 = 1-10 μM including high selectivity index). The new inhibitors thus identified were modified, based on the docking models, and revealed preliminary structure-activity relationships. Moreover, the genius in silico screening performance was validated by using an enrichment factor. We believe our designed scaffold could contribute to the improvement of HCV chemotherapy.

Intermolecular Diels-Alder reactions of brominated masked o-benzoquinones with electron-deficient dienophiles. A detour method to synthesize bicyclo[2.2.2]octenones from 2-methoxyphenols

Intermolecular Diels-Alder reactions of masked o-benzoquinones, i.e., 6,6-dimethoxy-2,4-cyclohexadienones 5-7 and 21-24 generated from 2-methoxyphenols 1-3 and 17-20, respectively, with electron-deficient dienophiles leading to highly functionalized bicyclo[2.2.2]octenones are described. The masked o-benzoquinones (MOBs) 5-7 underwent Diels-Alder cycloadditions with methyl acrylate, methyl methacrylate, and methyl vinyl ketone to provide bicyclo[2.2.2]octenones 13a-c to 15a-c (direct method) in low to moderate yields with the concomitant formation of considerable amounts of dimers 9-11. To retard dimerization and to improve the yields of the requisite bicyclo[2.2.2]octenones, a detour method comprised of sequential bromination of 2-methoxyphenols 1-4, oxidation and Diels-Alder reaction, and debromination has been developed. The oxidation of bromophenols 17-20 produced MOBs 21-24 which are stable enough to be isolated. The MOBs 21-24 underwent cycloaddition with electron-deficient dienophiles in a very efficient manner to afford the corresponding cycloadducts 25a-c to 28a-c in good to high yields without self-dimerization. When the cycloadducts 25a-c to 28a-c were treated with either Bu3SnH/AIBN or tributylammonium formate-palladium reagent, the corresponding debrominated products 13a-c to 16a-c were obtained in high to excellent yields. In general, the cycloadducts 13a-c to 15a-c were obtained in 20-40% higher yields via the detour method than those via the direct method. In both routes, the Diels-Alder reactions proceeded in a highly regio- and stereoselective manner to furnish a single cycloadduct in each case.

A facile and regioselective synthesis of donor-substituted 2-(2-halophenyl)acetaldehyde acetals

Starting from vanillin (5a) a facile and high yielding procedure for the preparation of the donor substituted (2-bromophenyl)- and (2-iodophenyl)-acetaldehyde acetals 13c and 16c is described. Homologization of O-benzylvanillin to obtain the phenylacetaldehyde acetal 15c succeeds by Wittig reaction with the phosphonium chloride 11 and subsequent addition of methanol. 15c is brominated with pyridinium bromide perbromide in methanol to yield the bromo acetal 13c in 65% yield from vanillin. Iodination of 15c with iodine and iodic acid leads to the iodo acetal 16c.

Stereochemistry and Mechanisms of the 3-Carboxymuconate Fungal Pathway in Neurospora SY4a

The cyclisation of cis,cis-3-carboxymuconic acid 2, catalysed by cycloisomerase enzyme of Neurospora crassa SY4a, has been shown to occur by syn addition of the 1-carboxy group to the 4,5-double bond to give (S)-(-)-carboxymuconolactone 3.Thus, the absolute configuration of the lactone 3 was determined by ozonolysis to give (S)-malic(L-malic) acid.Furthermore, incubation of trisodium cis,cis-3-carboxy-5-deuteriomuconate 9 then ozonolysis of the derived lactone 28 gave (2S,3S)-3-deuteriomalic acid 29.This evidence for syn addition was confirmed by a complementary incubation of undedeuteriated 3-carboxymuconate in deuterium oxide, giving the lactone 31 and hence (2S,3R)-3-deuteriomalic acid 32. The degradation of 3-carboxymuconolactone 3 by multifunctional enzyme complex of Neurospora, to give 3-oxoadipic acid 5, has been studied with the deuteriated trisodium muconates 27, 14 and 20.The overall transformation has been found to involve an intramolecular, suprafacial 1,3-shift of hydrogen (or deuterium) from C-4 in the lactone to C-5 in the oxoadipic acid.The location and stereochemistry of deuterium in the oxoadipic acids 44 and 45 were esteblished by conversion of these acids into the optically active 2-deuteriosuccinic acids 46 and 47, respectively.The 1,3-shift provides compelling eveidence for the formation of the enol lactone 4 as an enzyme-bound intermediate.Successive enzymic hydrolysis and decarboxylation would then complete the biosynthesis of 3-oxoadipic acid 5.