4-(Dimethylamino)-2,5-dimethoxybenzaldehyde

Base Information

• Chemical Name: 4-(Dimethylamino)-2,5-dimethoxybenzaldehyde
• CAS No.: 88753-04-2
• Molecular Formula: C₁₁H₁₅NO₃
• Molecular Weight: 209.245
• NSC Number: 156547
• DSSTox Substance ID: DTXSID20303080
• Wikidata: Q82048193
• ChEMBL ID: CHEMBL1894579
• Mol file: 88753-04-2.mol

Synonyms:4-(dimethylamino)-2,5-dimethoxybenzaldehyde;88753-04-2;NSC156547;CHEMBL1894579;SCHEMBL15985695;DTXSID20303080;NSC-156547;NCGC00188246-01;NCGC00188246-02;NCGC00188246-03;AT-051/43422773

Chemical Property of 4-(Dimethylamino)-2,5-dimethoxybenzaldehyde

Chemical Property:

• Vapor Pressure: 0.000262mmHg at 25°C
• Boiling Point: 323.4°Cat760mmHg
• Flash Point: 149.4°C
• Density: 1.118g/cm³
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 209.10519334
• Heavy Atom Count: 15
• Complexity: 208

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=C(C=C(C(=C1)OC)C=O)OC

Technology Process of 4-(Dimethylamino)-2,5-dimethoxybenzaldehyde

There total 1 articles about 4-(Dimethylamino)-2,5-dimethoxybenzaldehyde 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: 78.0%

2,5-dimethoxy-N,N-dimethylaniline (4031-94-1) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2,5-dimethoxy-4-dimethylaminobenzaldehyde (88753-04-2)

Guidance literature:

With trichlorophosphate; at 0 - 65 ℃; Inert atmosphere;

DOI:10.1021/ja510602z

Reference yield: 74.0%

Methyltriphenylphosphonium bromide (1779-49-3) + 2,5-dimethoxy-4-dimethylaminobenzaldehyde (88753-04-2) → 2,5-dimethoxy-4-dimethylaminostyrene

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 0.5h; Inert atmosphere;

2,5-dimethoxy-4-dimethylaminobenzaldehyde; In tetrahydrofuran; hexane; Inert atmosphere;

DOI:10.1021/ja510602z

Reference yield:

2,5-dimethoxy-4-dimethylaminobenzaldehyde (88753-04-2) → 5-((E)-4-((E)-4-(dimethylamino)-2,5-dimethoxystyryl)styryl)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzenesulfonic acid

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: palladium diacetate; tris-(o-tolyl)phosphine; triethylamine / N,N-dimethyl-formamide / 20 h / 110 °C / Inert atmosphere; Sealed tube

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - 30 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: palladium diacetate; tris-(o-tolyl)phosphine; triethylamine / N,N-dimethyl-formamide / 18 h / 110 °C / Inert atmosphere; Sealed tube

With n-butyllithium; palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/ja510602z

upstream raw materials:

2,5-dimethoxy-N,N-dimethylaniline

N,N-dimethyl-formamide

Refernces