[(1E)-4,4-dicyano-3-(dimethylamino)buta-1,3-dienyl]-dimethylazanium

Base Information

• Chemical Name: [(1E)-4,4-dicyano-3-(dimethylamino)buta-1,3-dienyl]-dimethylazanium
• CAS No.: 91945-90-3
• Molecular Formula: C₁₀H₁₄N₄
• Molecular Weight: 190.248
• DSSTox Substance ID: DTXSID80426507
• Mol file: 91945-90-3.mol

Synonyms:[(1E)-4,4-dicyano-3-(dimethylamino)buta-1,3-dienyl]-dimethylazanium;2-[1,3-bis(dimethylamino)-2-propenylidene]malononitrile;ZINC02243923;DTXSID80426507

Chemical Property of [(1E)-4,4-dicyano-3-(dimethylamino)buta-1,3-dienyl]-dimethylazanium

Chemical Property:

• Vapor Pressure: 3.76E-07mmHg at 25°C
• Melting Point: 145-147°C
• Boiling Point: 416.7°Cat760mmHg
• Flash Point: 192.5°C
• PSA: 54.06000
• Density: 1.047g/cm³
• LogP: 0.92456
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 191.129671495
• Heavy Atom Count: 14
• Complexity: 325

Purity/Quality:

98%min ^*data from raw suppliers

2-[1,3-BIS(DIMETHYLAMINO)-2-PROPENYLIDENE]MALONONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[NH+](C)C=CC(=C(C#N)C#N)N(C)C
• Isomeric SMILES: C[NH+](C)/C=C/C(=C(C#N)C#N)N(C)C

Technology Process of [(1E)-4,4-dicyano-3-(dimethylamino)buta-1,3-dienyl]-dimethylazanium

There total 2 articles about [(1E)-4,4-dicyano-3-(dimethylamino)buta-1,3-dienyl]-dimethylazanium 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: 93.0%

α-Cyano-β-dimethylaminocrotononitrile (14164-26-2) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-[1,3-bis(dimethylaminoallylidene)]malononitrile (91945-90-3)

Guidance literature:

at 100 ℃; for 1.33333h;

DOI:10.1021/jm0504407

Reference yield: 70.0%

α-Cyano-β-dimethylaminocrotononitrile (14164-26-2) + N,N-dimethylformamide diethyl diacetal (1188-33-6) → 2-[1,3-bis(dimethylaminoallylidene)]malononitrile (91945-90-3)

Guidance literature:

for 1h; Heating;

Reference yield:

2-[1,3-bis(dimethylaminoallylidene)]malononitrile (91945-90-3) → 9-dimethylamino-3-(p-bromophenyl)-3H-5-thia-1,3,6-triazafluoren-4-one

Guidance literature:

Multi-step reaction with 4 steps

1.1: 98 percent / HCl(gas) / methanol / 10 h / 0 °C

2.1: NaH / tetrahydrofuran / 0 °C

2.2: tetrahydrofuran / 24 h / 20 °C

2.3: 85 percent / NaH / tetrahydrofuran / 1.83 h / Heating

3.1: 99 percent / ethanol / 4.5 h / Heating

4.1: 62 percent / p-toluenesulfonic acid / toluene / 130 °C

With hydrogenchloride; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; ethanol; toluene;

DOI:10.1021/jm0504407

upstream raw materials:

α-Cyano-β-dimethylaminocrotononitrile

N,N-dimethylformamide diethyl diacetal

N,N-dimethyl-formamide dimethyl acetal

Downstream raw materials:

2-amino-4-dimethylamino-3-cyanopyridine

2-chloro-4-(dimethylamino)nicotinonitrile

5-amino-4-dimethylaminothieno[8,9-b]pyridine-6-carboxylic acid methyl ester

9-dimethylamino-3-(4-ethylphenyl)-3H-5-thia-1,3,6-triazafluoren-4-one