2-BROMO-3-HYDROXY-4-METHOXYBENZALDEHYDE

Base Information

• Chemical Name: 2-BROMO-3-HYDROXY-4-METHOXYBENZALDEHYDE
• CAS No.: 2973-58-2
• Molecular Formula: C8H7 Br O3
• Molecular Weight: 231.046
• Hs Code.: 2913000090
• European Community (EC) Number: 628-234-4
• NSC Number: 139143,12212
• DSSTox Substance ID: DTXSID70279307
• Nikkaji Number: J420.769F
• Wikidata: Q72445960
• Mol file: 2973-58-2.mol

Synonyms:Isovanillin,2-bromo- (6CI); p-Anisaldehyde, 2-bromo-3-hydroxy- (7CI,8CI);2-Bromo-3-formyl-6-methoxyphenol; 2-Bromo-3-hydroxy-4-methoxybenzaldehyde;2-Bromo-3-hydroxy-p-anisaldehyde; 2-Bromoisovanillin; Bromovanin; NSC 12212;NSC 139143

Chemical Property of 2-BROMO-3-HYDROXY-4-METHOXYBENZALDEHYDE

Chemical Property:

• Vapor Pressure: 0.00126mmHg at 25°C
• Melting Point: 202-207oC(lit.)
• Boiling Point: 289.5°Cat760mmHg
• PKA: 7.71±0.15(Predicted)
• Flash Point: 128.9°C
• PSA: 46.53000
• Density: 1.653g/cm³
• LogP: 1.97580
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Dichloromethane, Ethyl Acetate
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 229.95786
• Heavy Atom Count: 12
• Complexity: 162

Purity/Quality:

97% ^*data from raw suppliers

Bromovanin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C(=C(C=C1)C=O)Br)O
• Uses: 2-Bromo-3-hydroxy-4-methoxybenzaldehyde (2-Bromo-isovanillin) may be used in the preparation of:2-hydroxy-3-methoxybenzaldehyde semicarbazone (HMBS)2-cyclopentyl-7-methoxy-1-benzofuran-4-carbaldehyde3-(benzyloxy)-2-bromo-4-methoxybenzaldehydeIt may also be used as a starting material in the total synthesis of the following natural products:pareitroponedenbinobin(±)-codeine

Technology Process of 2-BROMO-3-HYDROXY-4-METHOXYBENZALDEHYDE

There total 16 articles about 2-BROMO-3-HYDROXY-4-METHOXYBENZALDEHYDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

isovanillin (621-59-0) → 2-bromoisovanillin (2973-58-2)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1055/s-0036-1589147

Reference yield:

(S)-(-)-methyl 6-(2-bromo-3-formyl-6-methoxyphenoxy)-cyclohex-1-enecarboxylate (312920-40-4) → 2-bromoisovanillin (2973-58-2)

Guidance literature:

With palladium diacetate; (iPr)NEt; triphenylphosphine; In acetonitrile; at 100 ℃;

DOI:10.1021/ja054449+

Reference yield:

2-Bromo-3-[1,3]dithian-2-yl-6-methoxy-phenol → 2-bromoisovanillin (2973-58-2)

Guidance literature:

With mercury(II) perchlorate; In methanol; chloroform;

upstream raw materials:

isovanillin

2-bromo-3,4-dimethoxybenzylaldehyde

3-benzyloxy-4-methoxybenzaldehyde

bromine

Downstream raw materials:

2-bromo-3,4-dimethoxybenzylaldehyde

2-bromo-3-<(2-methylprop-2-enyl)oxy>-4-methoxybenzaldehyde

3-(benzyloxy)-2-bromo-4-methoxybenzaldehyde

2-Bromo-3-(cyclohexan-2-en-1-oxy)-4-methoxy-benzaldehyde

Refernces

Synthesis and bactericidal activity of 6-H(nitro)-9- arylidenedeoxyvasicinones and their perchlorates

10.1007/s10600-008-9105-0

The research focuses on the synthesis and bactericidal activity of 6-H(nitro)-9-arylidenedeoxyvasicinones and their perchlorates. Deoxyvasicinone and 6-nitrodeoxyvasicinone were reacted with various aromatic aldehydes, including 3,4-dimethoxybenzaldehyde, isovanillin, 2-bromoisovanillin, 5-bromovanillin, and furfurol, in glacial acetic acid to produce a series of target compounds (2a-e and 3a-i). These compounds were characterized by IR, PMR, and mass spectra. The study also involved the preparation of perchlorates (4a-i) by heating the synthesized compounds in acetic acid in the presence of concentrated HClO4. The synthesized compounds were tested for their bactericidal properties against various gram-positive and gram-negative bacterial strains, showing moderate to low activity.

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