TYRPHOSTIN A9

Base Information

• Chemical Name: TYRPHOSTIN A9
• CAS No.: 10537-47-0
• Deprecated CAS: 51601-81-1,68072-88-8
• Molecular Formula: C18H22 N2 O
• Molecular Weight: 282.385
• Hs Code.: 2926909090
• European Community (EC) Number: 634-647-0
• NSC Number: 242557
• UNII: 87TE8MRS65
• DSSTox Substance ID: DTXSID1042106
• Nikkaji Number: J9.807H
• Wikipedia: SF-6847
• Wikidata: Q27155778
• NCI Thesaurus Code: C2026
• Pharos Ligand ID: YMAZ8W1HXFC2
• Metabolomics Workbench ID: 45111
• ChEMBL ID: CHEMBL78150
• Mol file: 10537-47-0.mol

Synonyms:Malononitrile,(3,5-di-tert-butyl-4-hydroxybenzylidene)- (6CI,7CI,8CI);Propanedinitrile,[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]- (9CI);2,6-Di-tert-butyl-4-(2,2-dicyanovinyl)phenol;3,5-di-tert-Butyl-4-hydroxybenzylidenemalonitrile;3,5-di-tert-Butyl-4-hydroxybenzylidenemalononitrile;AG 17;GCP 5126;Malonoben;NSC 242557;RG 50872;SF 6847;Tyrphostin 9;Tyrphostin A 9;Tyrphostin AG 17;

Chemical Property of TYRPHOSTIN A9

Chemical Property:

• Appearance/Colour: solid yellow
• Vapor Pressure: 1.55E-06mmHg at 25°C
• Melting Point: 141-143℃ (ethanol )
• Refractive Index: 1.554
• Boiling Point: 386.8 ºCat 760 mmHg
• PKA: 7.55±0.40(Predicted)
• Flash Point: 187.7 ºC
• PSA: 67.81000
• Density: 1.064 g/cm³
• LogP: 4.41776
• Storage Temp.: Store at RT
• Solubility.: ethanol: 20 mg/mL
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 282.173213330
• Heavy Atom Count: 21
• Complexity: 459

Purity/Quality:

98%,99%, ^*data from raw suppliers

Malonoben ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C=C(C#N)C#N
• Description: Tyrphostin 9 (10537-47-0) inhibits PDGF receptor tyrosine kinase (IC50?= 1.2 μM)1and is a potent (10 nM) inhibitor of oxidative phosphorylation2. Inhibits cell growth by disrupting mitochondria.3 Tyrphostin 9 perturbs the golgi complex and blocks proliferation of vascular smooth muscle cells.4
• Uses: Tyrphostin A9 can be used for inhibiting tyrosine kinase functions in C2C12 cells. It has also been used to disrupt membrane potential in mammalian cells. SF 6847 is an inhibitor of EGFR with IC50 of 460 μM. Selective inhibitor of PDGF receptor tyrosine kinase

Technology Process of TYRPHOSTIN A9

There total 2 articles about TYRPHOSTIN A9 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: 95.0%

malononitrile (109-77-3) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0) → malonoben (10537-47-0)

Guidance literature:

With ammonium acetate; In ethanol; at 50 - 80 ℃;

Reference yield:

→ malonoben (10537-47-0)

Guidance literature:

entspr. Hydroxybenzaldehyd, Malonitril;

Reference yield: 88.0%

phenyl(2-phenyl-2,3-dihydrobenzo[d]thiazol-2-yl)methanone (6125-26-4) + malonoben (10537-47-0) → 2-(1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxo-2-phenylethyl)malononitrile

Guidance literature:

With sodium dihydrogenphosphate; 1-hydroxy-1,2-benzodioxol-3-(1H)-one; In dichloromethane; at 20 ℃; for 8h; Inert atmosphere; Irradiation;

DOI:10.1021/acs.orglett.9b01717

upstream raw materials:

malononitrile

3,5-di-t-butyl-4-hydroxybenzaldehyde

Downstream raw materials:

C₅₄H₉₀N₆O₁₈*C₁₈H₂₁N₂O^(1-)*K⁽¹⁺⁾

Refernces

• 1、 Hori, Hitoshi,Nagasawa, Hideko,Ishibashi, Masaki,Uto, Yoshihiro,Hirata, Akihiko,Saijo, Kouichi,Ohkura, Kazuto,Kirk, Kenneth L,Uehara, Yoshimasa. "TX-1123: An antitumor 2-hydroxyarylidene-4-cyclopentene-1,3-dione as a protein tyrosine kinase inhibitor having low mitochondrial toxicity". . p. 3257 - 3265. Retrieved 2007/10/03.
• 2、 Katsumi,Kondo,Fuse,Yamashita,Hidaka,Hosoe,Takeo,Yamashita,Watanabe. "Studies on styrene derivatives. II. Synthesis and antiinflammatory activity of 3,5-di-tert-butyl-4-hydroxystyrenes". . p. 1619 - 1627. Retrieved 2007/10/02.