[(E)-2-[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]ethenyl]phosphonic acid

Base Information

• Chemical Name: [(E)-2-[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]ethenyl]phosphonic acid
• CAS No.: 19730-77-9
• Molecular Formula: C9H12NO5P
• Molecular Weight: 245.169
• NSC Number: 124469
• ChEMBL ID: CHEMBL3427371
• Mol file: 19730-77-9.mol

Synonyms:CHEMBL3427371;NSC124469;BDBM50084933;NSC-124469;19730-77-9

Chemical Property of [(E)-2-[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]ethenyl]phosphonic acid

Chemical Property:

• Vapor Pressure: 9.98E-18mmHg at 25°C
• Boiling Point: 649°C at 760 mmHg
• Flash Point: 346.3°C
• Density: 1.583g/cm³
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 245.04530948
• Heavy Atom Count: 16
• Complexity: 302

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC=C(C(=C1O)CO)C=CP(=O)(O)O
• Isomeric SMILES: CC1=NC=C(C(=C1O)CO)/C=C/P(=O)(O)O

Technology Process of [(E)-2-[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]ethenyl]phosphonic acid

There total 6 articles about [(E)-2-[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]ethenyl]phosphonic acid 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: 100.0%

diethyl 2-(3-hydroxy-4-hydroxymethyl-2-methyl-5-pyridyl)ethenylphosphonate → 2-(3-hydroxy-4-hydroxymethyl-2-methyl-5-pyridyl)ethenylphosphonic acid (19730-77-9)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2015.02.049

Reference yield:

diethyl 2-(3,4-O-isopropylidene-2-methyl-5-pyridyl)ethenylphosphonate → 2-(3-hydroxy-4-hydroxymethyl-2-methyl-5-pyridyl)ethenylphosphonic acid (19730-77-9)

Guidance literature:

Multi-step reaction with 2 steps

1: formic acid / water / 1 h / Reflux

2: trimethylsilyl bromide / dichloromethane / 20 °C / Inert atmosphere

With formic acid; trimethylsilyl bromide; In dichloromethane; water;

DOI:10.1016/j.bmc.2015.02.049

Reference yield:

5-hydroxy-6-methyl-3,4-pyridinedimethanol (65-23-6) → 2-(3-hydroxy-4-hydroxymethyl-2-methyl-5-pyridyl)ethenylphosphonic acid (19730-77-9)

Guidance literature:

Multi-step reaction with 5 steps

1: sulfuric acid / dichloromethane / 6 h / 45 °C / Inert atmosphere

2: manganese(IV) oxide / dichloromethane / 2 h / 20 °C

3: sodium hydride / cyclohexane; mineral oil / 20 °C

4: formic acid / water / 1 h / Reflux

5: trimethylsilyl bromide / dichloromethane / 20 °C / Inert atmosphere

With manganese(IV) oxide; formic acid; trimethylsilyl bromide; sulfuric acid; sodium hydride; In dichloromethane; cyclohexane; water; mineral oil; 3: |Wittig Olefination;

DOI:10.1016/j.bmc.2015.02.049

upstream raw materials:

5-hydroxy-6-methyl-3,4-pyridinedimethanol

(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol

2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine-5-carboxaldehyde

Refernces

• 1、 Knobloch, Gunnar,Jabari, Nauras,Stadlbauer, Sven,Schindelin, Hermann,K?hn, Maja,Gohla, Antje. "Synthesis of hydrolysis-resistant pyridoxal 5′-phosphate analogs and their biochemical and X-ray crystallographic characterization with the pyridoxal phosphatase chronophin". . p. 2819 - 2827. Retrieved 2015/03/30.