Ethyl 4-(hydroxymethyl)picolinate

Base Information

• Chemical Name: Ethyl 4-(hydroxymethyl)picolinate
• CAS No.: 59663-96-6
• Molecular Formula: C9H11NO3
• Molecular Weight: 181.191
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID10561450
• Wikidata: Q82445269
• Mol file: 59663-96-6.mol

Synonyms:Ethyl 4-(hydroxymethyl)picolinate;59663-96-6;ethyl 4-(hydroxymethyl)pyridine-2-carboxylate;Ethyl4-(hydroxymethyl)picolinate;ethyl 4-hydroxymethyl-2-pyridinecarboxylate;SCHEMBL2935704;DTXSID10561450;WPDFCSISXJTYIW-UHFFFAOYSA-N;2-Ethoxycarbonylpyridine-4-methanol;MFCD09844039;AKOS006312963;BS-17685;CS-0151671;D82505;ethyl 4-(hydroxymethyl)-pyridine-2-carboxylate

Chemical Property of Ethyl 4-(hydroxymethyl)picolinate

Chemical Property:

• Melting Point: 78-79 °C
• Boiling Point: 344.8±32.0 °C(Predicted)
• PKA: 13.16±0.10(Predicted)
• PSA: 59.42000
• Density: 1.200±0.06 g/cm3(Predicted)
• LogP: 0.75060
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 181.07389321
• Heavy Atom Count: 13
• Complexity: 172

Purity/Quality:

98%Min ^*data from raw suppliers

Ethyl4-(hydroxymethyl)picolinate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=NC=CC(=C1)CO

Technology Process of Ethyl 4-(hydroxymethyl)picolinate

There total 7 articles about Ethyl 4-(hydroxymethyl)picolinate 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: 16.0%

ethanol (64-17-5) + 2-Cyano-4-(hydroxymethyl)pyridine (71935-32-5) → ethyl 4-(hydroxymethyl)-pyridine-2-carboxylate (59663-96-6)

Guidance literature:

ethanol; 2-Cyano-4-(hydroxymethyl)pyridine; With chloro-trimethyl-silane; at 50 ℃; for 12h;

With water; sodium carbonate;

Reference yield:

pyridine-4-methanol (586-95-8) → ethyl 4-(hydroxymethyl)-pyridine-2-carboxylate (59663-96-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / imidazole / CH₂Cl₂; dimethylformamide / 3 h

2: 94 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 20 h / Ambient temperature

3: 83 percent / Et₃N / 3 h / 90 °C

4: 2.) 6 N aq. HCl / 1.) EtOH, RT,, 20 h, 2.) EtOH, RT, 20 h

With 1H-imidazole; hydrogenchloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570300309

Reference yield:

4-((tert-butyldimethylsilyloxy)methyl)pyridine (117423-41-3) → ethyl 4-(hydroxymethyl)-pyridine-2-carboxylate (59663-96-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 20 h / Ambient temperature

2: 83 percent / Et₃N / 3 h / 90 °C

3: 2.) 6 N aq. HCl / 1.) EtOH, RT,, 20 h, 2.) EtOH, RT, 20 h

With hydrogenchloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1002/jhet.5570300309

upstream raw materials:

ethanol

2-cyano-4-[{(tert-butyldimethylsilyl)oxy}methyl]pyridine

sodium ethanolate

pyridine-4-methanol