4-Hydroxy-3-pyridinemethanol

Base Information

• Chemical Name: 4-Hydroxy-3-pyridinemethanol
• CAS No.: 177592-15-3
• Molecular Formula: C₆H₇NO₂
• Molecular Weight: 125.127
• DSSTox Substance ID: DTXSID60442629
• Wikidata: Q82260009
• Mol file: 177592-15-3.mol

Synonyms:142890-84-4;3-(Hydroxymethyl)pyridin-4(1H)-one;3-(Hydroxymethyl)pyridin-4-ol;177592-15-3;4-Hydroxy-3-pyridinemethanol;3-(hydroxymethyl)-1H-pyridin-4-one;4(1H)-Pyridinone,3-(hydroxymethyl)-(9CI);3-Pyridinemethanol,4-hydroxy-(9CI);4-Hydroxypyridine-3-methanol;3-pyridinemethanol,4-hydroxy-;SCHEMBL5115644;DTXSID60442629;4(1h)-pyridinone,3-(hydroxymethyl)-;AKOS006349687;AKOS015966289;SB53530;FT-0730440

Chemical Property of 4-Hydroxy-3-pyridinemethanol

Chemical Property:

• PSA: 53.09000
• LogP: -0.13280
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 125.047678466
• Heavy Atom Count: 9
• Complexity: 182

Purity/Quality:

97% ^*data from raw suppliers

3-(Hydroxymethyl)pyridin-4-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC=C(C1=O)CO

Technology Process of 4-Hydroxy-3-pyridinemethanol

There total 6 articles about 4-Hydroxy-3-pyridinemethanol 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: 88.0%

4-amino-3-hydroxymethylpyridine (138116-34-4) → 4-hydroxy-3-hydroxymethylpyridine (177592-15-3)

Guidance literature:

With sulfuric acid; sodium nitrite; In water; for 2h; Heating;

DOI:10.1080/00397919608004536

Reference yield:

3-picoline-N-oxide (1003-73-2) → 4-hydroxy-3-hydroxymethylpyridine (177592-15-3)

Guidance literature:

Multi-step reaction with 6 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

6: 88 percent / H₂SO₄, NaNO₂ / H₂O / 2 h / Heating

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

DOI:10.1080/00397919608004536

Reference yield:

3-methyl-4-nitropyridine N-oxide (1074-98-2) → 4-hydroxy-3-hydroxymethylpyridine (177592-15-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / H₂SO₃, sodium dichromate / 3 h / 55 °C

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

3: 49 percent / H₂SO₄ / 4 h / Heating

4: 90 percent / LiAlH₄ / tetrahydrofuran / 1) 35 deg C, 3 h, 2) reflux, 1 h

5: 88 percent / H₂SO₄, NaNO₂ / H₂O / 2 h / Heating

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

DOI:10.1080/00397919608004536

upstream raw materials:

4-amino-3-hydroxymethylpyridine

3-picoline-N-oxide

3-methyl-4-nitropyridine N-oxide

4-nitro-3-carboxypyridine 1-oxide

Refernces