4-Hydroxy-but-2-ynoic acid ethyl ester

Base Information

• Chemical Name: 4-Hydroxy-but-2-ynoic acid ethyl ester
• CAS No.: 31555-04-1
• Molecular Formula: C6H8O3
• Molecular Weight: 128.128
• DSSTox Substance ID: DTXSID90445921
• Wikidata: Q82264474
• Mol file: 31555-04-1.mol

Synonyms:Ethyl 4-hydroxybut-2-ynoate;31555-04-1;4-hydroxy-but-2-ynoic acid ethyl ester;2-Butynoic acid, 4-hydroxy-, ethyl ester;Tetrolic acid, hydroxy-, ethyl ester;ethyl 4-hydroxy-2-butynoate;ethyl gamma-hydroxytetrolate;SCHEMBL1513351;DTXSID90445921;WECHWIOGTZSRPV-UHFFFAOYSA-N;hydroxymethylacetylenecarboxylate ethyl ester;FT-0701076;E80339

Chemical Property of 4-Hydroxy-but-2-ynoic acid ethyl ester

Chemical Property:

• Boiling Point: 78 °C(Press: 0.5 Torr)
• PKA: 13.14±0.10(Predicted)
• PSA: 46.53000
• Density: 1.145±0.06 g/cm3(Predicted)
• LogP: -0.45480
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 128.047344113
• Heavy Atom Count: 9
• Complexity: 148

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C#CCO

Technology Process of 4-Hydroxy-but-2-ynoic acid ethyl ester

There total 6 articles about 4-Hydroxy-but-2-ynoic acid ethyl ester 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: 81.0%

ethyl 4-(4-methoxybenzyloxy)but-2-ynoate (207795-41-3) → ethyl 4-hydroxy-2-butynoate (31555-04-1)

Guidance literature:

With montmorillonite K 10 supported ammonium nitrate; In neat (no solvent); for 0.0416667h; Irradiation;

DOI:10.1016/S0040-4039(98)00352-9

Reference yield: 25.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + propynoic acid ethyl ester (623-47-2) → ethyl 4-hydroxy-2-butynoate (31555-04-1)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 0.5h;

DOI:10.1021/jo026592g

Reference yield: 21.0%

chloroformic acid ethyl ester (541-41-3) + propargyl alcohol (107-19-7) → ethyl 4-hydroxy-2-butynoate (31555-04-1)

Guidance literature:

Multistep reaction;

DOI:10.1021/jo060864o

upstream raw materials:

ethanol

4-hydroxy-2-butynoic acid

ethyl 4-((tetrahydro-2H-pyran-2-yl)oxy)but-2-ynoate

ethyl 4-(4-methoxybenzyloxy)but-2-ynoate

Downstream raw materials:

cleviolide

ethyl 4-acetoxyacetoacetate