Isocrotonic acid

Base Information

• Chemical Name: Isocrotonic acid
• CAS No.: 503-64-0
• Molecular Formula: C4H6 O2
• Molecular Weight: 86.0904
• Hs Code.: 2916190090
• European Community (EC) Number: 207-973-2
• NSC Number: 206946
• UNII: 85GQ7GL1UM
• DSSTox Substance ID: DTXSID70880977
• Nikkaji Number: J2.604B
• Wikipedia: Isocrotonic acid,Isocrotonic_acid
• Wikidata: Q1674400
• Metabolomics Workbench ID: 616
• Mol file: 503-64-0.mol

Synonyms:Isocrotonic acid;cis-Crotonic Acid;cis-2-Butenoic Acid;503-64-0;(Z)-Crotonic acid;(Z)-but-2-enoic acid;(2Z)-2-Butenoic acid;(2Z)-but-2-enoic acid;(Z)-2-Butenoic acid;2-Butenoic acid, (Z)-;2Z-butenoic acid;Crotonic acid, (Z)-;UNII-85GQ7GL1UM;2-butenoic acid, (2Z)-;85GQ7GL1UM;EINECS 207-973-2;.alpha.-Butenoic acid;.beta.-Methylacrylic acid;C4:1n-2;.alpha.-Crotonic acid;Isocrotonsaure;b-Crotonic acid;NSC-206946;perisocrotonic acid;cis-but-2-enoic acid;(Z)-CH3CH=CHCOOH;ISOCROTONIC ACID [MI];WLN: QV1U2 -T;CHEBI:36253;DTXSID70880977;LMFA01030194;NSC206946;AKOS025296158;EN300-367570;Q1674400

Chemical Property of Isocrotonic acid

Chemical Property:

• Vapor Pressure: 0.505mmHg at 25°C
• Melting Point: 15°
• Refractive Index: nD14 1.4483; nD20 1.4450
• Boiling Point: 177°Cat760mmHg
• PKA: 4.68±0.25(Predicted)
• Flash Point: 81.6°C
• PSA: 37.30000
• Density: 1.039g/cm³
• LogP: 0.64710
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 86.036779430
• Heavy Atom Count: 6
• Complexity: 73.6

Purity/Quality:

98%min ^*data from raw suppliers

(2Z)-2-BUTENOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC(=O)O
• Isomeric SMILES: C/C=C\C(=O)O

Technology Process of Isocrotonic acid

There total 34 articles about Isocrotonic 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: 65.0%

1,3-dibromobutan-2-one (815-51-0) → (Z)-but-2-enoic acid (503-64-0)

Guidance literature:

With potassium hydrogencarbonate; for 2.5h;

DOI:10.1021/ja992286h

Reference yield: 59.0%

2-Butynoic acid (590-93-2) → (Z)-but-2-enoic acid (503-64-0)

Guidance literature:

With quinoline; 5% palladium on barium sulphate; hydrogen; In diethyl ether; at 22 ℃; for 1h;

DOI:10.1021/jacs.9b02318

Reference yield:

2-Butynoic acid (590-93-2) → (Z)-but-2-enoic acid (503-64-0) + butyric acid (107-92-6)

Guidance literature:

With hydroxylamine; Na₃[Fe(CN)5NH₃]*3H₂O; In various solvent(s); at 100 ℃; pH=9.3;

DOI:10.1021/jo800302v

upstream raw materials:

2-acetylpropanoic acid ethyl ester

2-butenoic acid

(E)-but-2-enoic acid

(E)-3-chloro-2-butenoic acid

Downstream raw materials:

2-butenoic acid

(E)-but-2-enoic acid

cis-2-buten-1-ol

4-deoxy-DL-threonic acid

Refernces

• 1、 Mohrig, Jerry R.,Carlson, Hans K.,Coughlin, Jane M.,Hofmeister, Gretchen E.,McMartin, Lea A.,Rowley, Elizabeth G.,Trimmer, Elizabeth E.,Wild, Andrew J.,Schultz, Steve C.. "Novel syn intramolecular pathway in base-catalyzed 1,2-elimination reactions of β-acetoxy esters". . p. 793 - 798. Retrieved 2007.
• 2、 Arzumanyan, A. M.,Attaryan, H. S.,Danagulyan, G. G.,Khachatryan, H. N.,Shahkhatuni, A. G.. "Vinylacidic Acid in the Reaction of Aza-Michael with 1-Ethylpyrazole". . p. 1488 - 1490. Retrieved 2020/10/02.
• 3、 Loesche, Ann-Christine,Brückner, Reinhard. "Dienolates of Cycloalkenones and α,β-Unsaturated Esters Form Diels–Alder Adducts by a Michael/Michael-Tandem Reaction Rather Than in One Step". supporting information. p. 562 - 573. Retrieved 2018/12/11.