2-Bromo-4-methoxy-5-(benzyloxy)benzaldehyde

Base Information

• Chemical Name: 2-Bromo-4-methoxy-5-(benzyloxy)benzaldehyde
• CAS No.: 6451-86-1
• Molecular Formula: C15H13BrO3
• Molecular Weight: 321.17
• Hs Code.: 2913000090
• DSSTox Substance ID: DTXSID60447831
• Wikidata: Q72446140
• Mol file: 6451-86-1.mol

Synonyms:6451-86-1;2-bromo-4-methoxy-5-(benzyloxy)benzaldehyde;5-Benzyloxy-2-bromo-4-methoxybenzaldehyde;5-(benzyloxy)-2-bromo-4-methoxybenzaldehyde;2-bromo-4-methoxy-5-phenylmethoxybenzaldehyde;2-BROMO-4-METHOXY-5-BENZYLOXYBENZALDEHYDE;5-benzyloxy-2-bromo-4-methoxy-benzaldehyde;Benzaldehyde, 2-bromo-4-methoxy-5-(phenylmethoxy)-;6-Bromobenzyl isovanillin;SCHEMBL1318429;DTXSID60447831;RUBXMEDWBCBLEZ-UHFFFAOYSA-N;AMY31592;MFCD00666893;AKOS015889657;AB06713;AC-14432;DS-11718;CS-0187100;FT-0602479;C76022;3-BENZYLOXY-4-METHOXY-6-BROMOBENZALDEHYE;A834796;AN-652/43285749;A1-00586;2-bromo-4-methoxy-5-(benzyloxy)benzaldehyde, AldrichCPR

Chemical Property of 2-Bromo-4-methoxy-5-(benzyloxy)benzaldehyde

Chemical Property:

• Vapor Pressure: 1.63E-07mmHg at 25°C
• Melting Point: 142.4-143.3 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• Refractive Index: 1.611
• Boiling Point: 427.5 °C at 760 mmHg
• Flash Point: 212.3 °C
• PSA: 35.53000
• Density: 1.421 g/cm³
• LogP: 3.84920
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 320.00481
• Heavy Atom Count: 19
• Complexity: 279

Purity/Quality:

98%min ^*data from raw suppliers

2-Bromo-4-methoxy-5-benzyloxybenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C(=C1)Br)C=O)OCC2=CC=CC=C2
• Uses: 6-Bromobenzylisovanillin is an intermediate in the synthesis of 3,8-Dihydroxy-9-methoxy-6H-Dibenzo[b,d]pyran-6-one (D455545) which has been used in anti-wrinkle agents and is known as a collagen production promoter, MMP-1 production inhibitor and elastase activity inhibitor containing urolithin.

Technology Process of 2-Bromo-4-methoxy-5-(benzyloxy)benzaldehyde

There total 20 articles about 2-Bromo-4-methoxy-5-(benzyloxy)benzaldehyde 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: 98.0%

2-bromoisovanillin (2973-59-3) + benzyl bromide (100-39-0) → 5-benzyloxy-2-bromo-4-methoxybenzaldehyde (6451-86-1)

Guidance literature:

In N,N-dimethyl-formamide; at 25 ℃; for 5h; Inert atmosphere;

Reference yield: 90.0%

2-bromoisovanillin (2973-59-3) + benzyl chloride (100-44-7) → 5-benzyloxy-2-bromo-4-methoxybenzaldehyde (6451-86-1)

Guidance literature:

2-bromoisovanillin; With potassium carbonate; In N,N-dimethyl-formamide; for 0.5h;

benzyl chloride; In N,N-dimethyl-formamide; at 60 ℃; for 18h;

DOI:10.1002/adsc.202100547

Reference yield: 87.0%

[5-(benzyloxy)-2-bromo-4-methoxyphenyl]methanol (13397-01-8) → 5-benzyloxy-2-bromo-4-methoxybenzaldehyde (6451-86-1)

Guidance literature:

With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline; In 1,4-dioxane; at 80 ℃; Solvent; Time; Schlenk technique;

DOI:10.1080/00397911.2013.879389

upstream raw materials:

2-bromoisovanillin

benzyl chloride

3-benzyloxy-6-bromo-4-hydroxybenzaldehyde

dimethyl sulfate

Downstream raw materials:

5-Benzyloxy-4-methoxy-2-methylsulfanyl-benzaldehyde

5-benzyloxy-2-bromo-4,β-dimethoxystyrene

[5-(benzyloxy)-2-bromo-4-methoxyphenyl]methanol

2-bromoisovanillin

Refernces

• 1、 Cailly, Thomas,Dubost, Emmanuelle,Fabis, Frédéric,Fossé, Pierre,Vigier, Clément. "Controlled Access to C1-Symmetrical Cyclotriveratrylenes (CTVs) by Using a Sequential Barluenga Boronic Coupling (BBC) Approach". supporting information. p. 3756 - 3761. Retrieved 2021/07/14.
• 2、 -. "DIMERIC COMPOUNDS AS STING AGONISTS". Paragraph 553. . Retrieved 2021/06/11.