4-Bromo-2-hydroxybenzaldehyde

Base Information

• Chemical Name: 4-Bromo-2-hydroxybenzaldehyde
• CAS No.: 22532-62-3
• Molecular Formula: C7H5BrO2
• Molecular Weight: 201.019
• Hs Code.: 2913000090
• European Community (EC) Number: 636-586-5
• DSSTox Substance ID: DTXSID40398953
• Nikkaji Number: J1.379.160K
• Wikidata: Q72456806
• Mol file: 22532-62-3.mol

Synonyms:4-Bromo-2-hydroxybenzaldehyde;22532-62-3;4-Bromosalicylaldehyde;4-Bromo-2-hydroxy-benzaldehyde;2-hydroxy-4-bromobenzaldehyde;MFCD06252606;BENZALDEHYDE, 4-BROMO-2-HYDROXY-;4-Bromo-2-hydroxybenaldehyde;SCHEMBL1006586;DTXSID40398953;HXTWKHXDFATMSP-UHFFFAOYSA-N;BCP00254;BBL102159;STL555958;4-Bromo-2-hydroxybenzaldehyde, 97%;AKOS005216763;AB23661;AC-5051;BG-0702;CS-W001114;SY010339;AM20030389;B3637;FT-0600809;EN300-53580;W-201939;Z405051414

Chemical Property of 4-Bromo-2-hydroxybenzaldehyde

Chemical Property:

• Vapor Pressure: 0.01mmHg at 25°C
• Melting Point: 50-54 °C
• Refractive Index: 1.657
• Boiling Point: 256.23 °C at 760 mmHg
• PKA: 7.21±0.10(Predicted)
• Flash Point: 108.765 °C
• PSA: 37.30000
• Density: 1.737 g/cm³
• LogP: 1.96720
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Soluble in methanol.
• 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

4-Bromosalicylaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, N, Xn
• Hazard Codes: Xi,N,Xn
• Statements: 22-50
• Safety Statements: 60

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1Br)O)C=O
• Uses: 4-Bromosalicylaldehyde is a substituted salicylaldehyde used in the synthesis of BIIB042, a γ-secretase modulator. It is an important raw material and intermediate used in organic synthesis, Pharmaceuticals, agrochemicals and dyestuffs.

Technology Process of 4-Bromo-2-hydroxybenzaldehyde

There total 27 articles about 4-Bromo-2-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: 89.1%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3-Bromophenol (591-20-8) → 4-bromosalicylaldehyde (22532-62-3)

Guidance literature:

3-Bromophenol; With triethylamine; magnesium chloride; In acetonitrile; at 20 ℃; for 0.333333h;

formaldehyd; In acetonitrile; for 4h; Reflux;

DOI:10.1021/acs.jmedchem.5b00440

Reference yield: 53.0%

4-bromo-2-hydroxy-N-methoxy-N-methylbenzamide → 4-bromosalicylaldehyde (22532-62-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1055/s-0040-1707400

Reference yield: 50.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-bromo-phenol (106-41-2) → 4-bromosalicylaldehyde (22532-62-3)

Guidance literature:

4-bromo-phenol; With triethylamine; magnesium chloride; In acetonitrile; at 25 ℃; for 0.333333h;

formaldehyd; In acetonitrile; for 4h; Reflux;

upstream raw materials:

chloroform

3-Bromophenol

Bromoform

2-amino-4-bromobenzaldehyde

Downstream raw materials:

5-bromo-2-formylphenyl acetate

4-(2-Methyl-imidazo[1,2-a]pyridin-3-ylazo)-benzoic acid [1-(4-bromo-2-hydroxy-phenyl)-meth-(E)-ylidene]-hydrazide

1-(4-{[1-(4-Bromo-2-hydroxy-phenyl)-meth-(Z)-ylidene]-amino}-benzoyl)-1,3-dicyclohexyl-urea

2-(allyloxy)-4-bromobenzaldehyde

Refernces

• 1、 Hodgson,Jenkinson. "". . p. 1740,3041. Retrieved 1927.
• 2、 Inoue, Seiichi,Yanai, Takayoshi,Ando, Shinji,Nakazawa, Akinori,Honda, Kiyoshi,Hoshino, Yujiro,Asai, Tomoyuki. "Synthesis and physical properties of novel liquid crystals containing pyranobenzopyrans as a core structure". . p. 4746 - 4752. Retrieved 2005.
• 3、 Bricelj, Ale?a,Gütschow, Michael,Schnakenburg, Gregor,Sosi?, Izidor,Steinebach, Christian,Voell, Sabine Anna,Vu, Lan Phuong. "A Facile Synthesis of Ligands for the von Hippel-Lindau E3 Ligase". supporting information. p. 2521 - 2527. Retrieved 2020/09/07.
• 4、 Remarchuk, Travis,Angelaud, Rémy,Askin, David,Kumar, Archana,Thompson, Andrew S.,Cheng, Hua,Reichwein, John F.,Chen, Yanping,St-Jean, Frédéric. "Manufacture of the PI3K β-Sparing Inhibitor Taselisib. Part 1: Early-Stage Development Routes to the Bromobenzoxazepine Core". supporting information. p. 775 - 782. Retrieved 2019/05/24.