52783-83-2

Basic information

• Product Name: 4-ACETOXY-2-BROMO-5-METHOXYBENZALDEHYDE 98
• Synonyms: 4-ACETOXY-2-BROMO-5-METHOXYBENZALDEHYDE 98;4-Acetoxy-2-bromo-5-methoxybenzaldehyde 98%;5-bromo-4-formyl-2-methoxyphenyl acetate(SALTDATA: FREE);4-(acetyloxy)-2-broMo-5-Methoxy-Benzaldehyde;6-BroMovanillin Acetate
• CAS NO: 52783-83-2
• Molecular Formula: C₁₀H₉BrO₄
• Molecular Weight: 273.0811
• Product Categories: Aldehydes;blocks;Bromides
• Mol File: 52783-83-2.mol

Chemical Properties

• Melting Point: 110-113
• Boiling Point: 336.4 °C at 760 mmHg
• Flash Point: 157.2 °C
• Appearance: /
• Density: 1.526 g/cm³
• Vapor Pressure: 0.000113mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: Keep Cold
• Solubility: Chloroform, DCM, Ethyl Acetate
• CAS DataBase Reference: 4-ACETOXY-2-BROMO-5-METHOXYBENZALDEHYDE 98(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ACETOXY-2-BROMO-5-METHOXYBENZALDEHYDE 98(52783-83-2)
• EPA Substance Registry System: 4-ACETOXY-2-BROMO-5-METHOXYBENZALDEHYDE 98(52783-83-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 52783-83-2(Hazardous Substances Data)

Usage

Uses

6-Bromovanillin Acetate is used in the synthesis of BMS-593214, a potent, selective FVIIa inhibitor.

InChI:InChI=1/C10H9BrO4/c1-6(13)15-10-4-8(11)7(5-12)3-9(10)14-2/h3-5H,1-2H3

Upstream product

• 881-68-5 vanillin acetate 
• 121-33-5 vanillin 

Downstream Products

• 60632-40-8 6-bromovanillin 
• 161196-87-8 2-bromo-4-hydroxy-5-methoxybenzonitrile 
• 90050-65-0 2-Bromo-4-hydroxy-5-methoxybenzoic acid 
• 40705-22-4 4-benzyloxy-6-bromo-3-methoxybenzaldehyde 
• 127027-59-2 Ethyl-6-(benzyloxy)-7-methoxyindol-2-carboxylat 
• 127027-65-0 Ethyl-6-(benzyloxy)-4-bromo-7-methoxyindol-2-carboxylat 
• 127027-70-7 6-(Benzyloxy)-7-methoxy-4-nitro-1H-indol-2-carbonsaeure-ethylester 
• 127027-63-8 Ethyl-2-azido-3-hydroxy-3-<2'-bromo-4'-(benzyloxy)-5'-methoxyphenyl>propanoat 
• 499217-06-0 4-Hydroxy-5-methoxy-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde 
• 864717-15-7 2-bromo-5-methoxy-4-[(4-nitrophenyl)methoxy]benzaldehyde 
• 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 
• 1429310-01-9 C₃₈H₃₃N₃O₄ 

Relevant articles and documents

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.

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.

BORON-CONTAINING SMALL MOLECULES

Compounds, pharmaceutical formulations, and methods of treating bacterial infections are disclosed.

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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.

Discovery and gram-scale synthesis of BMS-593214, a potent, selective FVIIa inhibitor

A 6-amidinotetrahydroquinoline screening hit was driven to a structurally novel, potent, and selective FVIIa inhibitor through a combination of library synthesis and rational design. An efficient gram-scale synthesis of the active enantiomer BMS-593214 was developed, which required significant optimization of the key Povarov annulation. Importantly, BMS-593214 showed antithrombotic efficacy in a rabbit arterial thrombosis model. A crystal structure of BMS-593214 bound to FVIIa highlights key contacts with Asp 189, Lys 192, and the S2 pocket.

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.

Tetrahydroquinoline derivatives as antithrombotic agents

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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.