3-Butynoic acid

Base Information

• Chemical Name: 3-Butynoic acid
• CAS No.: 2345-51-9
• Molecular Formula: C4H4O2
• Molecular Weight: 84.0746
• Hs Code.: 29161900
• European Community (EC) Number: 607-235-3
• DSSTox Substance ID: DTXSID50178001
• Nikkaji Number: J247.950H
• Wikidata: Q27105463
• Metabolomics Workbench ID: 52861
• Mol file: 2345-51-9.mol

Synonyms:3-Butynoic acid;but-3-ynoic acid;2345-51-9;3-Butynoate;But-3-insaeure;CH#CCH2COOH;But-3-ynoate;MFCD02258494;but-3-ynoicacid;CH.equiv.CCH2COOH;CH.$.CCH2COOH;LCWG001;CHEBI:1461;DTXSID50178001;AMY19285;STR05356;ZFA99027;GEO-00633;STL415173;AKOS000186880;AB11673;CS-W004784;AC-30551;SY040154;B4969;FT-0692094;EN300-97486;C06144;F14007;J-015114;Q27105463;Z295890060

Chemical Property of 3-Butynoic acid

Chemical Property:

• Vapor Pressure: 0.186mmHg at 25°C
• Melting Point: 188-195℃
• Refractive Index: 1.46
• Boiling Point: 194.9 °C at 760 mmHg
• PKA: 3.62±0.10(Predicted)
• Flash Point: 82.6 °C
• PSA: 37.30000
• Density: 1.152 g/cm³
• LogP: 0.09430
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 84.021129366
• Heavy Atom Count: 6
• Complexity: 95.4

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Butynoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T
• Statements: 22-41-34-24/25
• Safety Statements: 26-36-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CCC(=O)O
• Uses: Some of the applications of 3-butynoic acid are:Synthesis of functionalized γ-butyrolactones and tetrahydrofurans via Conia-ene cyclizations.Synthesis of allenoates for [2+2] cycloadditions with alkenes.Phosphine-catalyzed synthesis of highly functionalized coumarins.Synthesis of various useful organotin reagents via radical hydrostannation of 3-butynoic acid.

Technology Process of 3-Butynoic acid

There total 7 articles about 3-Butynoic acid 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: 98.3%

carbon dioxide (124-38-9,18923-20-1) + propargyl bromide (106-96-7) → 3-butynoic acid (2345-51-9)

Guidance literature:

With magnesium; In tetrahydrofuran; at 20 - 60 ℃; for 3h; Temperature; Inert atmosphere;

Reference yield: 93.0%

3-Butyn-1-ol (927-74-2) → 3-butynoic acid (2345-51-9)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In acetone; at 0 - 20 ℃;

DOI:10.1016/j.bioorg.2018.11.045

Reference yield:

propargyl bromide (106-96-7) → 3-butynoic acid (2345-51-9)

Guidance literature:

With diethyl ether; magnesium; anschliessend mit Kohlendioxid;

DOI:10.1021/ja01155a568

upstream raw materials:

3-Butyn-1-ol

bromoallene

carbon dioxide

1,2-propanediene

Downstream raw materials:

ethyl cyanoacetate

butyric acid

6-phenyl-hexa-3,5-diynoic acid

carbon dioxide

Refernces

• 1、 Wakabayashi,Saito,Sugihara,Sugimura,Murata. "Some preparation methods of a tricyclo[4.1.0.02,7]hept-4-en-3-one skeleton". . p. 2019 - 2027. Retrieved 1995.
• 2、 Suzuki, Yuji,Miyagi, Yu,Shiotsuki, Masashi,Inai, Yoshihito,Masuda, Toshio,Sanda, Fumio. "Synthesis and helical structures of poly(ω-alkynamide)s having chiral side chains: Effect of solvent on their screw-sense inversion". . p. 15131 - 15143. Retrieved 2014.
• 3、 Abbas, Ata,Xing, Bengang,Loh, Teck-Peng. "Allenamides as orthogonal handles for selective modification of cysteine in peptides and proteins". . p. 7491 - 7494. Retrieved 2014.
• 4、 Fang, Weiwei,Breit, Bernhard. "Tandem Regioselective Hydroformylation-Hydrogenation of Internal Alkynes Using a Supramolecular Catalyst". supporting information. p. 14817 - 14821. Retrieved 2018/10/24.