Dimethyl 4-(hydroxymethyl)pyridine-2,6-dicarboxylate

Base Information

• Chemical Name: Dimethyl 4-(hydroxymethyl)pyridine-2,6-dicarboxylate
• CAS No.: 852936-60-8
• Molecular Formula: C10H11NO5
• Molecular Weight: 225.201
• DSSTox Substance ID: DTXSID70465809
• Nikkaji Number: J2.173.653H
• Wikidata: Q82292050
• Mol file: 852936-60-8.mol

Synonyms:852936-60-8;Dimethyl 4-(hydroxymethyl)pyridine-2,6-dicarboxylate;2,6-Pyridinedicarboxylic acid, 4-(hydroxymethyl)-, dimethyl ester;4-(Hydroxymethyl)-2,6-pyridinedicarboxylic Acid 2,6-Dimethyl Ester;SCHEMBL17911801;DTXSID70465809;AC9332;MFCD27978005;AKOS030254684;SY251004;CS-0456339;FT-0669800;EN300-12002537;Dimethyl4-(hydroxymethyl)pyridine-2,6-dicarboxylate;dimethyl 4-(hydroxymethyl) pyri-dine-2,6-dicarboxylate;2,6-DIMETHYL 4-(HYDROXYMETHYL)PYRIDINE-2,6-DICARBOXYLATE

Chemical Property of Dimethyl 4-(hydroxymethyl)pyridine-2,6-dicarboxylate

Chemical Property:

• PSA: 85.72000
• LogP: 0.14710
• Solubility.: Dichloromethane
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 225.06372245
• Heavy Atom Count: 16
• Complexity: 244

Purity/Quality:

97% ^*data from raw suppliers

4-(Hydroxymethyl)-2,6-pyridinedicarboxylicAcid2,6-DimethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=CC(=N1)C(=O)OC)CO
• Uses: Intermediate of dipicolinate based chromophores. Can be used in the preparation of polyaminopolycarboxylate ligands, useful for their luminescence properties, and in the preparation of a lanthanide tags, designed for site-specific labeling of proteins. As intermediate of dipicolinate based chromophores, 4-(HydroxyMethyl)-2,6-pyridinedicarboxylic Acid 2,6-DiMethyl Ester can be used in the preparation of polyaminopolycarboxylate ligands, useful for their luminescence properties, and in the preparation of a lanthanide tags, designed for site-specific labeling of proteins.

Technology Process of Dimethyl 4-(hydroxymethyl)pyridine-2,6-dicarboxylate

There total 4 articles about Dimethyl 4-(hydroxymethyl)pyridine-2,6-dicarboxylate 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: 65.0%

methanol (67-56-1) + 2,6-bis(methoxycarbonyl)pyridine (5453-67-8) → dimethyl 4-(hydroxylmethyl)pyridine-2,6-dicarboxylate (852936-60-8)

Guidance literature:

With perchloric acid; iron(II) perchlorate hexahydrate; dihydrogen peroxide; In water; at 0 - 20 ℃; for 3h; regioselective reaction;

DOI:10.3998/ark.5550190.0013.513

Reference yield:

Pyridine-2,6-dicarboxylic acid (499-83-2) → dimethyl 4-(hydroxylmethyl)pyridine-2,6-dicarboxylate (852936-60-8)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₃COCl

2: 41 percent / FeSO₄*7H₂₀; H₂O₂; H₂SO₄ / H₂O / 15 - 30 °C

With sulfuric acid; dihydrogen peroxide; iron(II) sulfate; acetyl chloride; In water;

DOI:10.1080/00397910600634381

Reference yield:

methanol (67-56-1) + 2,6-bis(methoxycarbonyl)pyridine (5453-67-8) → dimethyl 4-(hydroxylmethyl)pyridine-2,6-dicarboxylate (852936-60-8) + dimethyl 4-formyl-pyridine-2,6-dicarboxylate (1072925-96-2)

Guidance literature:

With ferrous(II) sulfate heptahydrate; sulfuric acid; dihydrogen peroxide; In water; at 0 - 20 ℃;

DOI:10.1016/j.jinorgbio.2012.02.032

upstream raw materials:

methanol

2,6-bis(methoxycarbonyl)pyridine

Pyridine-2,6-dicarboxylic acid

dihydrogen peroxide

Downstream raw materials:

dimethyl 4-tosyloxymethylpyridine-2,6-dicarboxylate

dimethyl 4-(4-(2-(2,6-bis(methoxycarbonyl)pyridine-4-yl)vinyl)styryl)pyridine-2,6-dicarboxylate

dimethyl 4-(methylenetriphenylphosphoniumchloride)pyridine-2,6-dicarboxylate

C₁₇H₂₂N₂O₄