(4-Aminopyridin-3-yl)methanol

Base Information

• Chemical Name: (4-Aminopyridin-3-yl)methanol
• CAS No.: 138116-34-4
• Molecular Formula: C6H8N2O
• Molecular Weight: 124.142
• Hs Code.: 29333990
• European Community (EC) Number: 681-133-7
• DSSTox Substance ID: DTXSID10444916
• Wikidata: Q72441670
• Mol file: 138116-34-4.mol

Synonyms:4-aminopyridine-3-methanol;4-AP-3-Me0H

Chemical Property of (4-Aminopyridin-3-yl)methanol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 167-169℃
• Refractive Index: 1.628
• Boiling Point: 367.19 °C at 760 mmHg
• PKA: 13.54±0.10(Predicted)
• Flash Point: 175.871 °C
• PSA: 59.14000
• Density: 1.257 g/cm³
• LogP: 0.73730
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive.: Air Sensitive
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Slightly soluble in water.
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 124.063662883
• Heavy Atom Count: 9
• Complexity: 87.1

Purity/Quality:

99% ^*data from raw suppliers

(4-Amino-pyridin-3-yl)-methanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T+
• Statements: 28-36/37/38
• Safety Statements: 26-36/37/39-45-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=CC(=C1N)CO
• Uses: 4-Amino-3-pyridinemethanol is used as an organic chemical synthesis intermediate.

Technology Process of (4-Aminopyridin-3-yl)methanol

There total 9 articles about (4-Aminopyridin-3-yl)methanol 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: 90.0%

methyl 4-aminonicotinate (16135-36-7) → 4-amino-3-hydroxymethylpyridine (138116-34-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; 1) 35 deg C, 3 h, 2) reflux, 1 h;

DOI:10.1080/00397919608004536

Reference yield: 80.0%

4-aminonicotinaldehyde (42373-30-8) → 4-amino-3-hydroxymethylpyridine (138116-34-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1016/j.bmcl.2007.11.101

Reference yield:

3-picoline-N-oxide (1003-73-2) → 4-amino-3-hydroxymethylpyridine (138116-34-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 51 percent / HNO₃, H₂SO₄ / 2 h

2: 68 percent / H₂SO₃, sodium dichromate / 3 h / 55 °C

3: 88 percent / H₂ / Pd/C / acetic acid / 2280 Torr / 1) 30 deg C, 2 h, 2) 60 deg C, 2 h

4: 49 percent / H₂SO₄ / 4 h / Heating

5: 90 percent / LiAlH₄ / tetrahydrofuran / 1) 35 deg C, 3 h, 2) reflux, 1 h

With lithium aluminium tetrahydride; sodium dichromate; sulfuric acid; hydrogen; nitric acid; sulphurous acid; palladium on activated charcoal; In tetrahydrofuran; acetic acid;

DOI:10.1080/00397919608004536

upstream raw materials:

methyl 4-aminonicotinate

3-picoline-N-oxide

3-methyl-4-nitropyridine N-oxide

4-nitro-3-carboxypyridine 1-oxide

Downstream raw materials:

3-chloromethyl-pyridin-4-ylamine hydrochloride

3-((tert-butyldimethylsilyloxy)methyl)pyridin-4-amine

phenyl 3-((tert-butyldimethylsilyloxy)methyl)pyridin-4-ylcarbamate

1-(3-((tert-butyldimethylsilyloxy)methyl)pyridin-4-yl)-3-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)urea

Refernces

• 1、 -. "Substituted Heterocyclic Aza Compounds". Paragraph 0818. . Retrieved 2013/03/26.
• 2、 Leroy,Despres,Bigan,Blondeau. "Syntheses of ortho-hydroxymethylpyridinols and dioxaphosphorino[m,n-x]pyridines". . p. 2257 - 2272. Retrieved 2007/10/03.