3-Pyridinemethanol

Base Information

• Chemical Name: 3-Pyridinemethanol
• CAS No.: 100-55-0
• Molecular Formula: C6H7NO
• Molecular Weight: 109.128
• Hs Code.: 29333999
• European Community (EC) Number: 202-864-6
• NSC Number: 526046
• UNII: 9TF312056Y
• DSSTox Substance ID: DTXSID6023367
• Nikkaji Number: J4.983B
• Wikipedia: Nicotinyl_alcohol
• Wikidata: Q411732
• NCI Thesaurus Code: C61860
• Metabolomics Workbench ID: 122981
• ChEMBL ID: CHEMBL1235535
• Mol file: 100-55-0.mol

Synonyms:3 Hydroxymethylpyridine;3-Hydroxymethylpyridine;Alcohol, Nicotinic;Alcohol, Nicotinyl;beta Pyridylcarbinol;beta-Pyridylcarbinol;Hydrofluoride, Nicomethanol;Nicomethanol Hydrofluoride;Nicotinic Alcohol;Nicotinyl Alcohol;Nicotinyltartrate;Pyridine 3 Methanol;Pyridine-3-Methanol;Pyridylcarbinol;Radecol;Roniacol;Ronicol;Ronicol Retard

Chemical Property of 3-Pyridinemethanol

Chemical Property:

• Appearance/Colour: clear light yellow to yellow liquid
• Vapor Pressure: 0.00442mmHg at 25°C
• Melting Point: -7.7 °C
• Refractive Index: n20/D 1.545(lit.)
• Boiling Point: 266 °C at 760 mmHg
• PKA: 13.68±0.10(Predicted)
• Flash Point: 97.5 °C
• PSA: 33.12000
• Density: 1.124 g/cm³
• LogP: 0.57390
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: 1000mg/l
• Water Solubility.: soluble
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 109.052763847
• Heavy Atom Count: 8
• Complexity: 65.5

Purity/Quality:

99% ^*data from raw suppliers

3-Pyridinemethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1=CC(=CN=C1)CO
• Uses: 3-Pyridinemethanol is a useful synthetic intermediate. It can be used in the synthesis of histone deacetylase inhibitors. It can also be used to prepare (phenyl)(cyanopyrazinyl)urea derivatives as possible kinase-1 (Chk1) inhibitors. antineoplastic 3-Pyridinemethanol can be used as antineoplastic and used in the synthesis of histone deacetylase inhibitors.
• Therapeutic Function: Vasodilator

Technology Process of 3-Pyridinemethanol

There total 54 articles about 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: 99.0%

3-pyridinecarboxaldehyde (500-22-1) → 3-hydroxymethylpyridin (100-55-0)

Guidance literature:

With LaCu_0.67Si_1.33; hydrogen; In methanol; at 120 ℃; for 9h; under 22502.3 Torr; Autoclave;

DOI:10.1021/jacs.7b08252

Reference yield: 99.0%

→ 3-hydroxymethylpyridin (100-55-0)

Guidance literature:

With water; sodium hydroxide; In methanol; at 240 ℃; for 2h; Inert atmosphere; Autoclave;

Reference yield: 98.0%

methyl 3-pyridinecarboxylate (93-60-7) → 3-hydroxymethylpyridin (100-55-0)

Guidance literature:

With [RuCl₂(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; potassium tert-butylate; hydrogen; In tetrahydrofuran; at 50 ℃; for 5h; under 7500.75 Torr; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01900

upstream raw materials:

pyridine-3-carbonitrile

3-Aminomethylpyridine

methyl 3-pyridinecarboxylate

3-pyridinecarboxylic acid ethyl ester

Downstream raw materials:

4-hydroxy-benzoic acid-[3]pyridylmethyl ester

2,2-diphenyl-valeric acid-[3]pyridylmethyl ester

3-(acetoxymethyl)pyridine

3,4,5-trimethoxy-benzoic acid-[3]pyridylmethyl ester

Refernces

• 1、 Wang,Patel. "Hydrolysis of nicotinyl 6-aminonicotinate". . p. 204 - 207. Retrieved 1986.
• 2、 Widegren, Magnus B.,Clarke, Matthew L.. "Towards practical earth abundant reduction catalysis: Design of improved catalysts for manganese catalysed hydrogenation". . p. 6047 - 6058. Retrieved 2019.
• 3、 Cano, Israel,Chapman, Andrew M.,Urakawa, Atsushi,Van Leeuwen, Piet W. N. M.. "Air-stable gold nanoparticles ligated by secondary phosphine oxides for the chemoselective hydrogenation of aldehydes: Crucial role of the ligand". . p. 2520 - 2528. Retrieved 2014.
• 4、 Murakami et al.. "-". . p. 1197,1199. Retrieved 1966.
• 5、 Stivanello, Mariano,Leoni, Lucia,Bortolaso, Roberto. "Synthesis of 1,5-bis(triphenylphosphonium)pentan-3-ol dichloride and its application to the preparation of 1,7-di(pyridin-3-yl)heptan-4-ol". . p. 807 - 810. Retrieved 2002.
• 6、 Yamaguchi, Kazuya,Koike, Takeshi,Kim, Jung Won,Ogasawara, Yoshiyuki,Mizuno, Noritaka. "Highly dispersed ruthenium hydroxide supported on titanium oxide effective for liquid-phase hydrogen-transfer reactions". . p. 11480 - 11487. Retrieved 2008.
• 7、 Kinoshita,Ohishi. "Pyrimidine derivatives XII. A convenient preparation of 6-formylpyrimidinedione and 2- and 3-formylpyridine derivatives from corresponding nitrooxymethyl derivatives". . p. 1599 - 1603. Retrieved 1994.
• 8、 Sharma, Saurabh,Bhattacherjee, Dhananjay,Das, Pralay. "Supported Rhodium Nanoparticles Catalyzed Reduction of Nitroarenes, Arylcarbonyls and Aryl/Benzyl Sulfoxides using Ethanol/Methanol as In Situ Hydrogen Source". . p. 2131 - 2137. Retrieved 2018.
• 9、 Basavaiah, Deevi,Sharada, Duddu S.,Veerendhar, Ainelly. "Organo-base mediated Cannizzaro reaction". . p. 5771 - 5774. Retrieved 2006.
• 10、 Yamaguchi, Kazuya,Koike, Takeshi,Kotani, Miyuki,Matsushita, Mitsunori,Shinachi, Satoshi,Mizuno, Noritaka. "Synthetic scope and mechanistic studies of Ru(OH)x/Al 2O3-catalyzed heterogeneous hydrogen-transfer reactions". . p. 6574 - 6582. Retrieved 2005.