(2E,4E)-5-(4-(Dimethylamino)phenyl)penta-2,4-dienal

Base Information

• Chemical Name: (2E,4E)-5-(4-(Dimethylamino)phenyl)penta-2,4-dienal
• CAS No.: 20432-36-4
• Molecular Formula: C13H15NO
• Molecular Weight: 201.268
• European Community (EC) Number: 857-299-3
• Nikkaji Number: J823.183D,J307.739J
• Mol file: 20432-36-4.mol

Synonyms:20432-36-4;(2E,4E)-5-(4-(Dimethylamino)phenyl)penta-2,4-dienal;(2E,4E)-5-[4-(dimethylamino)phenyl]penta-2,4-dienal;83073-86-3;5-(4-(Dimethylamino)phenyl)penta-2,4-dienal;SCHEMBL1044097;AKOS006227671;BS-50079;F72651;EN300-9248475;(2E,4E)-5-[4-(dimethylamino)phenyl]-2,4-pentadienal;Z1198147337

Chemical Property of (2E,4E)-5-(4-(Dimethylamino)phenyl)penta-2,4-dienal

Chemical Property:

• Melting Point: 155-156?°C(lit.)
• PSA: 20.31000
• LogP: 2.52090
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 201.115364102
• Heavy Atom Count: 15
• Complexity: 235

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC=C(C=C1)C=CC=CC=O
• Isomeric SMILES: CN(C)C1=CC=C(C=C1)/C=C/C=C/C=O

Technology Process of (2E,4E)-5-(4-(Dimethylamino)phenyl)penta-2,4-dienal

There total 10 articles about (2E,4E)-5-(4-(Dimethylamino)phenyl)penta-2,4-dienal 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: 92.0%

3-(4-dimethylamino-phenyl)-propenal (20432-35-3,6203-18-5) + (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide (52509-14-5) → s-trans-((2trans-4trans)-5-(4-dimethylaminophenyl)phenyl)penta-2,4-dienal (20432-36-4)

Guidance literature:

3-(4-dimethylamino-phenyl)-propenal; (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide; With 18-crown-6 ether; sodium hydride; In tetrahydrofuran; at 20 ℃;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1081/SCC-120015766

Reference yield: 61.0%

3-(4-dimethylamino-phenyl)-propenal (20432-35-3,6203-18-5) + α,α-bis(trimethylsilyl)-tert-butylacetaldehyde imine (127896-07-5) → s-trans-((2trans-4trans)-5-(4-dimethylaminophenyl)phenyl)penta-2,4-dienal (20432-36-4)

Guidance literature:

3-(4-dimethylamino-phenyl)-propenal; α,α-bis(trimethylsilyl)-tert-butylacetaldehyde imine; With zinc dibromide; In tetrahydrofuran; at 20 ℃; for 2h;

With zinc(II) chloride; In diethyl ether; at 20 ℃; for 1h;

DOI:10.1515/HC.2001.7.4.331

Reference yield: 40.0%

C24H26O2P(1+)*Br(1-) + 4-dimethylamino-benzaldehyde (100-10-7) → s-trans-((2trans-4trans)-5-(4-dimethylaminophenyl)phenyl)penta-2,4-dienal (20432-36-4)

Guidance literature:

C₂₄H₂₆O₂P⁽¹⁺⁾*Br^(1-); With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

4-dimethylamino-benzaldehyde; In tetrahydrofuran; at 0 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.analchem.1c02289

upstream raw materials:

3-(4-dimethylamino-phenyl)-propenal

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

α,α-bis(trimethylsilyl)-tert-butylacetaldehyde imine

(1,3-dioxolan-2-ylmethyl)tributylphosphonium bromide

Refernces

• 1、 Plazuk, Damian,Janowska, Izabela,Klys, Arkadiusz,Hameed, Asia,Zakrzewski, Janusz. "A convenient synthesis of conjugated ω-arylpolyenals via Wittig reaction with (1,3-dioxan-2-yl-methyl)triphenylphosphonium bromide/sodium hydride". . p. 381 - 385. Retrieved 2003.
• 2、 Tillotson, John P.,Bogdanov, Georgii,Jucov, Evgheni V.,Khrustalev, Victor N.,Rigin, Sergei,Hales, Joel M.,Perry, Joseph W.,Timofeeva, Tatiana V.. "Synthesis, structure, linear and nonlinear properties of tricyanofuran–terminated merocyanine dyes". . p. 146 - 154. Retrieved 2019/04/26.
• 3、 Ono, Masahiro,Doi, Yuki,Watanabe, Hiroyuki,Ihara, Masafumi,Ozaki, Akihiko,Saji, Hideo. "Structure-activity relationships of radioiodinated diphenyl derivatives with different conjugated double bonds as ligands for α-synuclein aggregates". . p. 44305 - 44312. Retrieved 2016/06/09.