Ethyl 2-(hydroxymethyl)thiazole-4-carboxylate

Base Information

• Chemical Name: Ethyl 2-(hydroxymethyl)thiazole-4-carboxylate
• CAS No.: 40235-65-2
• Molecular Formula: C7H9NO3S
• Molecular Weight: 187.219
• Hs Code.: 2934100090
• European Community (EC) Number: 831-491-7
• DSSTox Substance ID: DTXSID70443021
• Nikkaji Number: J2.770.604E
• Wikidata: Q82260691
• Mol file: 40235-65-2.mol

Synonyms:Ethyl 2-(hydroxymethyl)thiazole-4-carboxylate;40235-65-2;Ethyl 2-(hydroxymethyl)-1,3-thiazole-4-carboxylate;Ethyl2-(hydroxymethyl)thiazole-4-carboxylate;SCHEMBL2838513;DTXSID70443021;ORBNJGCTXHRSBC-UHFFFAOYSA-N;MFCD20924035;AKOS016001958;DS-3627;ethyl 2-hydroxymethylthiazole-4-carboxylate;EN300-217195;ethyl 2-(hydroxymethyl)-thiazole-4-carboxylate;O11746;A873412;2-hydroxymethyl thiazole-4-carboxylic acid ethyl ester;2-Hydroxymethylthiazole-4-carboxylic acid ethyl ester;2-(Hydroxymethyl)thiazole-4-carboxylic acid ethyl ester;Z1334514632

Chemical Property of Ethyl 2-(hydroxymethyl)thiazole-4-carboxylate

Chemical Property:

• Melting Point: 80 °C
• Boiling Point: 297.9±20.0 °C(Predicted)
• PKA: 12.84±0.10(Predicted)
• PSA: 87.66000
• Density: 1.333±0.06 g/cm3(Predicted)
• LogP: 0.81210
• Storage Temp.: 2-8°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 187.03031432
• Heavy Atom Count: 12
• Complexity: 165

Purity/Quality:

99% ^*data from raw suppliers

Ethyl2-(hydroxymethyl)thiazole-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CSC(=N1)CO

Technology Process of Ethyl 2-(hydroxymethyl)thiazole-4-carboxylate

There total 1 articles about Ethyl 2-(hydroxymethyl)thiazole-4-carboxylate 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:

ethyl 2-methylthiazole-4-carboxylate (6436-59-5) → ethyl 2-(hydroxymethyl)-thiazole-4-carboxylate (40235-65-2)

Guidance literature:

Multi-step reaction with 2 steps

1: selenium(IV) oxide / acetic acid / 24 h / 100 °C

2: sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 - 25 °C

With selenium(IV) oxide; sodium tetrahydroborate; In tetrahydrofuran; acetic acid;

DOI:10.1016/j.tetlet.2016.01.051

Reference yield: 100.0%

ethyl 2-(hydroxymethyl)-thiazole-4-carboxylate (40235-65-2) → ethyl 2-(chloromethyl)thiazole-4-carboxylate (842130-48-7)

Guidance literature:

With thionyl chloride; In dichloromethane; at 0 - 45 ℃; for 2h;

DOI:10.1016/j.tetlet.2016.01.051

Reference yield:

ethyl 2-(hydroxymethyl)-thiazole-4-carboxylate (40235-65-2) → [4-(diphenyl-phosphinoylmethyl)-thiazol-2-yl]-methanol

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / imidazole / dimethylformamide

2: 65 percent / Dibal-H / CH₂Cl₂

3: 84 percent / CCl₄; PPh₃

4: n-BuLi / tetrahydrofuran

5: H₂O₂

6: 60 percent / TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; tetrachloromethane; n-butyllithium; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja010039j

upstream raw materials:

ethyl 2-methylthiazole-4-carboxylate

Downstream raw materials:

2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(diphenyl-phosphinoylmethyl)-thiazole

ethyl 2-(chloromethyl)thiazole-4-carboxylate

Refernces

• 1、 Brindisi, Margherita,Maramai, Samuele,Grillo, Alessandro,Brogi, Simone,Butini, Stefania,Novellino, Ettore,Campiani, Giuseppe,Gemma, Sandra. "Development of a practical and scalable route for the preparation of the deacetoxytubuvaline (dTuv) fragment of pretubulysin and analogs". . p. 920 - 923. Retrieved 2016/02/05.