alpha-[Amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)benzeneacetonitrile

Base Information

• Chemical Name: alpha-[Amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)benzeneacetonitrile
• CAS No.: 305350-87-2
• Molecular Formula: C₁₆H₁₂F₃N₃S
• Molecular Weight: 335.353
• Hs Code.: 2930909899
• European Community (EC) Number: 878-717-0
• DSSTox Substance ID: DTXSID90429549
• Wikidata: Q27084156
• Pharos Ligand ID: 4VGGBRYA2KVX
• ChEMBL ID: CHEMBL261237
• Mol file: 305350-87-2.mol

Synonyms:alpha-(amino((4-aminophenyl)thio)methylene)-2-(trifluoromethyl)benzeneacetonitrile;SL 327;SL-327;SL327 cpd

Chemical Property of alpha-[Amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)benzeneacetonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 127-128.2 °C
• Refractive Index: 1.631
• Boiling Point: 512.6°Cat760mmHg
• PKA: 3.42±0.10(Predicted)
• Flash Point: 263.8°C
• PSA: 101.13000
• Density: 1.4g/cm³
• LogP: 5.51228
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 32 mg/mL
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 335.07040306
• Heavy Atom Count: 23
• Complexity: 487

Purity/Quality:

99% ^*data from raw suppliers

SL 327 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(=C(N)SC2=CC=C(C=C2)N)C#N)C(F)(F)F
• Isomeric SMILES: C1=CC=C(C(=C1)/C(=C(\N)/SC2=CC=C(C=C2)N)/C#N)C(F)(F)F
• Description: The dual specific threonine/tyrosine kinase MEK is a key component of the RAS/RAF/MEK/ERK signaling pathway that regulates a diverse array of cellular processes. SL 327 is an inhibitor of MEK1 and MEK2 (IC50s = 0.18 and 0.22 μM), the kinases upstream of ERK1/2. It inhibits ERK1, MKK/p38, MKK4, JNK, and PKC at much higher concentrations (IC50s = >50, 21, >100, >100, >10 μM, respectively). Since SL 327 rapidly passes the blood-brain barrier, it has been used to dissect the effect of RAS/RAF/MEK/ERK signaling pathway inhibition on behavior, including long-term memory, spatial learning, and fear/operant conditioning.
• Uses: SL-327 is a selective inhibitor of MEK1 and MEK2, and ERK1, MEK-3/p38, MEK-4, JNK, and PKC at higher concentrations.

Technology Process of alpha-[Amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)benzeneacetonitrile

There total 5 articles about alpha-[Amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)benzeneacetonitrile 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: 22.0%

2-[2-[(trifluoromethyl)phenyl]]propanedinitrile (297745-44-9) + 4-aminotiophenol (1193-02-8) → Z-α-[amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)benzeneacetonitrile (305350-87-2)

Guidance literature:

With triethylamine; In tetrahydrofuran; at -78 - 20 ℃; for 21h;

DOI:10.1016/j.bioorg.2021.104955

Reference yield:

2-[2-[(trifluoromethyl)phenyl]]propanedinitrile (297745-44-9) + 4-aminotiophenol (1193-02-8) → Z-α-[amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)benzeneacetonitrile (305350-87-2) + E-α-[amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)benzeneacetonitrile (297744-40-2,305350-87-2)

Guidance literature:

2-[2-[(trifluoromethyl)phenyl]]propanedinitrile; 4-aminotiophenol; In tetrahydrofuran; degassed by placing under vacuum followed by flushing with N₂;

With triethylamine; at -78 ℃; degassed by placing under vacuum followed by flushing with N₂;

2-[2-[(trifluoromethyl)phenyl]]propanedinitrile; With triethylamine; more than 3 stages;

Reference yield:

2-[2-[(trifluoromethyl)phenyl]]propanedinitrile (297745-44-9) + 4-aminotiophenol (1193-02-8) → Z-α-[amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)benzeneacetonitrile (305350-87-2) + E-α-[amino[(4-aminophenyl)thio]methylene]-2-(trifluoromethyl)benzeneacetonitrile (297744-40-2,305350-87-2)

Guidance literature:

2-[2-[(trifluoromethyl)phenyl]]propanedinitrile; 4-aminotiophenol; In tetrahydrofuran; degassed by placing under vacuum followed by flushing with N₂;

With triethylamine; at -78 ℃; degassed by placing under vacuum followed by flushing with N₂;

2-[2-[(trifluoromethyl)phenyl]]propanedinitrile; With triethylamine; more than 3 stages;

upstream raw materials:

2-[2-[(trifluoromethyl)phenyl]]propanedinitrile

malononitrile

4-aminotiophenol

2-iodo(trifluoromethyl)benzene

Refernces

• 1、 -. "Amino-thio-acrylonitriles as MEK inhibitors". Page column 20. . Retrieved 2010/02/05.