4-Dimethylaminostilbene

Base Information

• Chemical Name: 4-Dimethylaminostilbene
• CAS No.: 838-95-9
• Molecular Formula: C16H17 N
• Molecular Weight: 223.318
• Hs Code.: 2921430090
• European Community (EC) Number: 678-388-1
• NSC Number: 30991
• UNII: 1V7P79915N
• DSSTox Substance ID: DTXSID401020720
• Nikkaji Number: J48.668J,J3.334K
• Wikidata: Q27252942
• Pharos Ligand ID: HSH5XYAKLKX6
• ChEMBL ID: CHEMBL83880
• Mol file: 838-95-9.mol

Synonyms:4-dimethylaminostilbene;4-dimethylaminostilbene, (cis)-isomer;4-dimethylaminostilbene, (trans)-isomer;trans-4-dimethylaminostilbene

Chemical Property of 4-Dimethylaminostilbene

Chemical Property:

• Melting Point: 150°C
• Refractive Index: 1.7020 (estimate)
• Boiling Point: 354.61°C (rough estimate)
• PSA: 3.24000
• Density: 1.0477 (rough estimate)
• LogP: 3.92300
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 223.136099547
• Heavy Atom Count: 17
• Complexity: 230

Purity/Quality:

4-(Dimethylamino)stilbene ^*data from reagent suppliers

Safty Information:

• Safety Statements: Poison by ingestion and subcutaneous routes. Questionable carcinogen with experimental carcinogenic and tumo"> x." target="_blank">Poison by ingestion and subcutaneous routes. Questionable carcinogen with experimental carcinogenic and tumo

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC=C(C=C1)C=CC2=CC=CC=C2
• Isomeric SMILES: CN(C)C1=CC=C(C=C1)/C=C/C2=CC=CC=C2

Technology Process of 4-Dimethylaminostilbene

There total 58 articles about 4-Dimethylaminostilbene 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: 99.0%

benzyl-triethylphosphonium bromide (7016-55-9) + 4-dimethylamino-benzaldehyde (100-10-7) → (E)-N,N-dimethyl-4-styrylbenzenamine (838-95-9)

Guidance literature:

benzyl-triethylphosphonium bromide; In water; at 20 ℃; for 0.25h;

With sodium hydroxide; In water; for 0.0333333h;

4-dimethylamino-benzaldehyde; In water; at 70 ℃; for 3h; optical yield given as %de; stereoselective reaction;

DOI:10.1002/ejoc.200900634

Reference yield: 99.0%

C13H23P*BrH + 4-dimethylamino-benzaldehyde (100-10-7) → (E)-N,N-dimethyl-4-styrylbenzenamine (838-95-9)

Guidance literature:

With sodium hydroxide; In water; at 70 ℃; for 3h; stereoselective reaction;

DOI:10.1080/10426507.2014.980907

Reference yield: 97.0%

N,N-dimethyl-4-(phenylethynyl)aniline (14301-08-7) → (E)-N,N-dimethyl-4-styrylbenzenamine (838-95-9)

Guidance literature:

With ethanol; Ru(η(2)-2-(2'-pyridyl)phenyl)Cl(CO)(PPh3)2; sodium t-butanolate; at 110 ℃; for 1h; stereoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.organomet.0c00074

upstream raw materials:

ethanol

1-[4-(dimethylamino)phenyl]-2-phenylethanol

benzylidene dibromide

4-dimethylamino-benzaldehyde

Downstream raw materials:

cis-[(2,2':6',2''-terpyridine)OsCl2(η2-(C,N)-PhCH=N=CH[C6H4NMe2])]PF6

cis-stilben

(E)-1,2-diphenyl-ethene

(Z)-1-[4-N,N-(dimethylamino)phenyl]-2-phenylethene

Refernces

• 1、 Fukazawa, Mizuki,Nogi, Keisuke,Sasamori, Takahiro,Takahashi, Fumiya,Yorimitsu, Hideki. "Reductive Difunctionalization of Aryl Alkenes with Sodium Metal and Reduction-Resistant Alkoxy-Substituted Electrophiles". supporting information. . Retrieved 2020/03/13.
• 2、 Chen, Dafa,Gong, Dawei,Hu, Bowen,Kong, Degong,Xia, Haiping,Yang, Weiwei. "A Bidentate Ru(II)-NC Complex as a Catalyst for Semihydrogenation of Alkynes to (E)-Alkenes with Ethanol". . . Retrieved 2020/03/19.