2-BROMO-6-HYDROXYBENZALDEHYDE

Base Information

• Chemical Name: 2-BROMO-6-HYDROXYBENZALDEHYDE
• CAS No.: 22532-61-2
• Molecular Formula: C7H5BrO2
• Molecular Weight: 201.019
• Hs Code.: 2913000090
• European Community (EC) Number: 696-195-0
• DSSTox Substance ID: DTXSID30474659
• Nikkaji Number: J1.399.370J
• Wikidata: Q72456798
• Mol file: 22532-61-2.mol

Synonyms:Salicylaldehyde,6-bromo- (8CI);6-Bromo-2-hydroxybenzaldehyde;6-Bromosalicylaldehyde;

Chemical Property of 2-BROMO-6-HYDROXYBENZALDEHYDE

Chemical Property:

• Melting Point: 50-52 °C
• Boiling Point: 243.393 °C at 760 mmHg
• PKA: 7.21±0.10(Predicted)
• Flash Point: 101.001 °C
• PSA: 37.30000
• Density: 1.737 g/cm³
• LogP: 1.96720
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 199.94729
• Heavy Atom Count: 10
• Complexity: 127

Purity/Quality:

98% ^*data from raw suppliers

2-Bromo-6-hydroxybenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Br)C=O)O
• Uses: 2-Bromo-6-hydroxybenzaldehyde, is a substituted salicylaldehyde used in the synthesis of BIIB042, a γ-secretase modulator.

Technology Process of 2-BROMO-6-HYDROXYBENZALDEHYDE

There total 15 articles about 2-BROMO-6-HYDROXYBENZALDEHYDE 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: 94.0%

2-bromo-6-methoxybenzaldehyde (126712-07-0) → 2-bromo-6-hydroxybenzaldehyde (22532-61-2)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/ja0568852

Reference yield: 70.0%

salicylaldehyde (90-02-8) → 2-bromo-6-hydroxybenzaldehyde (22532-61-2) + 5-bromosalicyclaldehyde (1761-61-1)

Guidance literature:

With trimethylsilyl bromide; bis(4-chlorophenyl)sulfoxide; In acetonitrile; at 25 ℃; for 6h; regioselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201900794

Reference yield: 60.0%

O-3-bromophenyl N,N-diethylcarbamate (863870-72-8) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-bromo-6-hydroxybenzaldehyde (22532-61-2)

Guidance literature:

O-3-bromophenyl N,N-diethylcarbamate; N,N-dimethyl-formamide; With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; for 1.25h; Inert atmosphere;

With hydrogenchloride; In water; at 0 ℃; for 14h; Inert atmosphere;

DOI:10.1021/ol302691j

upstream raw materials:

chloroform

3-Bromophenol

2-bromo-6-methoxybenzaldehyde

ortho-anisaldehyde

Downstream raw materials:

2-(1E,3-butadienyl)-3-bromophenol

2-(benzyloxy)-6-bromobenzaldehyde

ethyl (E)-3-(2-bromo-6-hydroxyphenyl)prop-2-enoate

C₅₂H₇₄N₂O₁₀Si₃

Refernces

• 1、 Ma, Xiantao,Yu, Jing,Jiang, Mengyuan,Wang, Mengyu,Tang, Lin,Wei, Mengmeng,Zhou, Qiuju. "Mild and Regioselective Bromination of Phenols with TMSBr". supporting information. p. 4593 - 4596. Retrieved 2019/07/05.
• 2、 Geddis, Stephen M.,Hagerman, Caroline E.,Galloway, Warren R. J. D.,Sore, Hannah F.,Goodman, Jonathan M.,Spring, David R.. "(Z)-selective Takai olefination of salicylaldehydes". supporting information. p. 323 - 328. Retrieved 2017/03/14.