3-Hydroxymethylantipyrine

Base Information

• Chemical Name: 3-Hydroxymethylantipyrine
• CAS No.: 18125-49-0
• Molecular Formula: C11H12 N2 O2
• Molecular Weight: 204.23
• Hs Code.: 2933199090
• UNII: 3F5YS569EB
• DSSTox Substance ID: DTXSID00171087
• Nikkaji Number: J276.054A
• Mol file: 18125-49-0.mol

Synonyms:3-HMAP;3-hydroxymethylantipyrine

Chemical Property of 3-Hydroxymethylantipyrine

Chemical Property:

• Vapor Pressure: 1.55E-05mmHg at 25°C
• Refractive Index: 1.611
• Boiling Point: 351.2°Cat760mmHg
• Flash Point: 166.2°C
• PSA: 47.16000
• Density: 1.265g/cm³
• LogP: 0.66830
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly, Heated, Sonicated), Methanol (Slightly, Sonicated)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 204.089877630
• Heavy Atom Count: 15
• Complexity: 282

Purity/Quality:

99%min ^*data from raw suppliers

3-Hydroxymethylantipyrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=CC(=O)N1C2=CC=CC=C2)CO
• Uses: Antipyrine (A697500), a non-steroidal anti-inflammatory drug, is widely utilized as a probe for human oxidative drug metabolism. Antipyrine metabolites are formed by various hepatic cytochrome P450 enzymes. 3-Hydroxymethylantipyrine is a metabolite of Antipyrine.

Technology Process of 3-Hydroxymethylantipyrine

There total 4 articles about 3-Hydroxymethylantipyrine 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: 98.0%

3-hydroxymethyl-4-bromoantipyrine (81122-69-2) → 3-Hydroxymethylantipyrine (18125-49-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; for 18h; Heating;

Reference yield:

antipyrine (60-80-0) → 3-Hydroxymethylantipyrine (18125-49-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / N-bromosuccinimide / CCl₄ / 0.33 h / Heating

2: 80 percent / Na₂CO₃, H₂O / acetone / 2 h / Heating

3: 98 percent / tri-n-butyltin hydride, azobisisobutyronitrile / tetrahydrofuran / 18 h / Heating

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; sodium carbonate; In tetrahydrofuran; tetrachloromethane; acetone;

Reference yield:

4-bromo-5-(bromomethyl)-1-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one (5767-66-8) → 3-Hydroxymethylantipyrine (18125-49-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Na₂CO₃, H₂O / acetone / 2 h / Heating

2: 98 percent / tri-n-butyltin hydride, azobisisobutyronitrile / tetrahydrofuran / 18 h / Heating

With 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; sodium carbonate; In tetrahydrofuran; acetone;

upstream raw materials:

3-hydroxymethyl-4-bromoantipyrine

antipyrine

4-bromo-5-(bromomethyl)-1-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

Downstream raw materials:

3-formyl-2-methyl-1-phenylpyrazol-5-one

4,5-bis-hydroxymethyl-1-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one

2-methyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-3,4-dicarbaldehyde

1-methyl-2-phenyl-1,2-dihydro-pyrazolo[3,4-d]pyridazin-3-one

Refernces

• 1、 Yoshimura,Shimeno,Tsukamoto. "Metabolism of drugs. LXX. Further study on antipyrine metabolism.". . p. 41 - 45. Retrieved 2007/10/04.