2973-59-3

Basic information

• Product Name: 2-Bromoisovanillin
• Synonyms: 2-BROMO-5-HYDROXY-4-METHOXYBENZALDEHYDE;AKOS 235-16;5-BROMOISOVANILIN;5-BROMOISOVANILLIN;5-BROMOISOVANILLIN (2-Bromo-5-Hydroxy-p-Anisaldehyde);2-Bromo-5-Hydroxy-4-Anisaldehyde;2-Bromo-5-hydroxy-p-anisaldehyde;Bromo-5-hydroxy-p-anisaldehyde
• CAS NO: 2973-59-3
• Molecular Formula: C₈H₇BrO₃
• Molecular Weight: 231.04
• EINECS: 1592732-453-0
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);API intermediates;Benzothiazoles
• Mol File: 2973-59-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: 98-100°C
• Boiling Point: 320.8 ºC at 760 mmHg
• Flash Point: 147.8 ºC
• Appearance: /
• Density: 1.653 g/cm³
• Vapor Pressure: 0.000166mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 8.69±0.23(Predicted)
• BRN: 1942858
• CAS DataBase Reference: 2-Bromoisovanillin(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromoisovanillin(2973-59-3)
• EPA Substance Registry System: 2-Bromoisovanillin(2973-59-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 2973-59-3(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white crystalline powder

Uses

2-Bromo-5-hydroxy-4-methoxybenzaldehyde was used in the synthesis of 4-bromo-2-methoxy-5-(2-methoxyethenyl)phenol.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 26, p. 3113, 1978 DOI: 10.1248/cpb.26.3113

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

Upstream product

• 621-59-0 isovanillin 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 881-57-2 isovanillin acetate 
• 69048-79-9 4-bromo-5-formyl-2-methoxyphenyl acetate 
• 121-32-4 4-hydroxy-3-ethoxybenzaldehyde 
• 56517-30-7 2-bromo-5-ethoxy-4-methoxybenzaldehyde 
• 17348-67-3 1-(tert-butyldimethylsilyloxy)-2-propane 
• 122584-18-3 N-(4-hydroxyphenethyl)-N-(2-bromo-5-hydroxy-4-methoxybenzyl)formamide 
• 179107-93-8 N-(p-hydroxyphenylethyl)-N-(6-bromo-3-hydroxy-4-methoxybenzyl)amine 
• 67-56-1 methanol 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 120-57-0 piperonal 
• 75437-87-5 6-bromo-4-hydroxy-3-(phenoxymethoxy)benzaldehyde 

Downstream Products

• 80832-63-9 3-hydroxy-4,6-dimethoxybenzaldehyde 
• 6451-86-1 5-benzyloxy-2-bromo-4-methoxybenzaldehyde 
• 188822-63-1 N-(2-bromo-5-hydroxy-4-methoxybenzyl)-N-(4-hydroxyphenethyl)methylamine 
• 179107-93-8 N-(p-hydroxyphenylethyl)-N-(6-bromo-3-hydroxy-4-methoxybenzyl)amine 
• 252186-55-3 4-bromo-2-methoxy-5-(2-nitroethenyl)phenol 
• 655238-34-9 2-bromo-5-hydroxy-4-methoxybenzyl alcohol 
• 122584-18-3 N-(4-hydroxyphenethyl)-N-(2-bromo-5-hydroxy-4-methoxybenzyl)formamide 
• 685873-72-7 2-bromo-4-methoxy-3-(4-nitrophenoxy)benzaldehyde 
• 121936-68-3 2-bromo-5-hydroxy-4-methoxybenzoic acid 
• 1097202-13-5 6-nitro-9-(3'-hydroxy-4'-methoxy-6'-bromobenzylidene)deoxyvasicinone 
• 1429257-21-5 1-(6-bromo-3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 510-77-0 (4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one 
• 510-77-0 (-)-narwedine 
• 1953-04-4 Galantamine hydrobromide 

Relevant articles and documents

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.

Single-Step Dual Functionalization: One-Pot Bromination-Cross-Dehydrogenative Esterification of Hydroxy Benzaldehydes with CCl 3 Br - A Comparison with Selectfluor

Bromination of phenolic compounds without directly using molecular bromine possesses much importance. In this article an Ir III /CCl 3 Br-assisted single-step double functionalization of hydroxy benzaldehydes is reported. It involves simultaneous esterification of the aldehyde group and bromination of the aryl ring of phenolic aldehydes in one-pot. The reaction proceeds under mild conditions in the presence of 445 nm blue LED light to obtain highly functionalized bromo hydroxy benzoates in moderate to good yields. In comparison, Selectfluor as an oxidant gives only non-bromo phenolic esters.

Synthesis of 5 - methoxy - 4 - hydroxy - 2 - boric acid aldehyde group benzenefrequency alcohol ester (by machine translation)

The invention provides a method for synthesizing 5 - methoxy - 4 - hydroxy - 2 - boric acid aldehyde group benzenefrequency alcohol ester. In particular, the invention relates to 3, 4 - dimethoxy formaldehyde as raw materials through the bromo to obtain 3, 4 - dimethoxy - 2 - bromophenylacetic formaldehyde, then by removing methyl 5 - hydroxy - 4 - methoxy - 2 - bromophenylacetic formaldehyde, then tert-butyl diphenyl silicon to protect hydroxyl to obtain 5 - tert-butyl diphenyl siloxy - 4 - methoxy - 2 - bromophenylacetic formaldehyde, then in order to glycerol acetal protected aldehyde group, then in BuLi under the action of triisopropyl borate reaction to obtain 5 - methoxy - 4 - tert-butyl diphenyl siloxy - 2 - aldehyde group benzene boric acid, then silicon protecting group to obtain 5 - methoxy - 4 - hydroxy - 2 - boric acid aldehyde group benzene, finally with the pinacone reaction ester to obtain the target product 5 - methoxy - 4 - hydroxy - 2 - boric acid aldehyde group benzenepinacone ester. The invention raw materials are easy, low cost, high yield, easy industrialization. (by machine translation)