2-(2-Amino-3-methoxyphenyl)-4H-1-benzopyran-4-one

Base Information

• Chemical Name: 2-(2-Amino-3-methoxyphenyl)-4H-1-benzopyran-4-one
• CAS No.: 167869-21-8
• Deprecated CAS: 868169-70-4
• Molecular Formula: C₁₆H₁₃NO₃
• Molecular Weight: 267.284
• Hs Code.: 29322090
• European Community (EC) Number: 620-943-7
• NSC Number: 679828
• UNII: SJE1IO5E3I
• DSSTox Substance ID: DTXSID40168416
• Nikkaji Number: J660.824H
• Wikidata: Q27088281
• NCI Thesaurus Code: C1625
• Pharos Ligand ID: 1RUTFKQFUSST
• ChEMBL ID: CHEMBL35482
• Mol file: 167869-21-8.mol

Synonyms:2-(2'-amino-3'-methoxyphenyl)oxanaphthalen-4-one;2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one;PD 098059;PD 98059;PD-098059;PD-98059;PD098059;PD09859;PD98059

Chemical Property of 2-(2-Amino-3-methoxyphenyl)-4H-1-benzopyran-4-one

Chemical Property:

• Appearance/Colour: yellow solid
• Vapor Pressure: 2.12E-08mmHg at 25°C
• Melting Point: 164～165℃
• Refractive Index: 1.651
• Boiling Point: 453.142 °C at 760 mmHg
• PKA: 1.21±0.10(Predicted)
• Flash Point: 221.938 °C
• PSA: 65.46000
• Density: 1.3 g/cm³
• LogP: 3.63200
• Storage Temp.: −20°C
• Solubility.: ethanol: 0.6 mg/mL
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 267.08954328
• Heavy Atom Count: 20
• Complexity: 407

Purity/Quality:

98% ^*data from raw suppliers

PD 98059 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-60-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=CC(=C1N)C2=CC(=O)C3=CC=CC=C3O2
• Description: PD 98059 is a noncompetitive inhibitor of the MAPK pathway. It prevents the activation of MEK by Raf or MEK kinase (a MAP3K) with an IC50 value of 2-7 μM but does not inhibit Raf-activated MAP2K1. It inhibits Raf activation of MAP2K2 with an IC50 value of 50 μM. PD 98059 also phosphorylates and activates AMP-activated protein kinase (AMPK) in a dose-dependent manner (EC50 = 35 μM in HEK293 cells). It increases the ratios of ADP to ATP and AMP to ATP and increases phosphorylation of the AMPK target acetyl-CoA carboxylase (ACC).
• Uses: A selective inhibitor of MEK and blocker of MAP PD 98059 is a selective inhibitor of MEK and blocker of MAPK.

Technology Process of 2-(2-Amino-3-methoxyphenyl)-4H-1-benzopyran-4-one

There total 2 articles about 2-(2-Amino-3-methoxyphenyl)-4H-1-benzopyran-4-one 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:

3-methoxy-2-nitrobenzoic acid (4920-80-3) → 2-(2-amino-3-methoxyphenyl)chromen-4-one (167869-21-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 15 h / 20 °C

2.1: potassium hydroxide; pyridine / 0.5 h / 50 °C

2.2: 20 °C / pH 4.5

3.1: acetic acid; sulfuric acid / 0.5 h / Reflux

4.1: tin; hydrogenchloride / ethanol / 2 h / Reflux

With pyridine; hydrogenchloride; tin; sulfuric acid; acetic acid; N-ethyl-N,N-diisopropylamine; HATU; potassium hydroxide; In ethanol; N,N-dimethyl-formamide;

Reference yield:

o-hydroxyacetophenone (118-93-4,104809-67-8) → 2-(2-amino-3-methoxyphenyl)chromen-4-one (167869-21-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 15 h / 20 °C

2.1: potassium hydroxide; pyridine / 0.5 h / 50 °C

2.2: 20 °C / pH 4.5

3.1: acetic acid; sulfuric acid / 0.5 h / Reflux

4.1: tin; hydrogenchloride / ethanol / 2 h / Reflux

With pyridine; hydrogenchloride; tin; sulfuric acid; acetic acid; N-ethyl-N,N-diisopropylamine; HATU; potassium hydroxide; In ethanol; N,N-dimethyl-formamide;

upstream raw materials:

3-methoxy-2-nitrobenzoic acid

o-hydroxyacetophenone

Refernces