3,3-Dimethylacrylic acid

Base Information

• Chemical Name: 3,3-Dimethylacrylic acid
• CAS No.: 541-47-9
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Hs Code.: 29161900
• European Community (EC) Number: 208-782-7
• NSC Number: 97179,2549
• UNII: EKV8I38F9I
• DSSTox Substance ID: DTXSID2047145
• Nikkaji Number: J13.743J
• Wikidata: Q27117043
• Metabolomics Workbench ID: 167
• ChEMBL ID: CHEMBL115725
• Mol file: 541-47-9.mol

Synonyms:beta,beta-dimethylacrylic acid;beta-methylcrotonic acid;senecioic acid

Chemical Property of 3,3-Dimethylacrylic acid

Chemical Property:

• Appearance/Colour: White prism-shape crystals
• Vapor Pressure: 0.19mmHg at 25°C
• Melting Point: 65-70 °C(lit.)
• Refractive Index: 1.4226 (estimate)
• Boiling Point: 194.5 °C at 760 mmHg
• PKA: pK1:5.12 (25°C)
• Flash Point: 96 °C
• PSA: 37.30000
• Density: 1.01 g/cm³
• LogP: 1.03720
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in water, and methanol.
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 98.6

Purity/Quality:

99% ^*data from raw suppliers

3-Methylcrotonic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,C
• Hazard Codes: Xi,C
• Statements: 37/38-41-34
• Safety Statements: 26-36/37/39-45-27

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC(=CC(=O)O)C
• Description: May be prepared by the action of alkalis or bases on the ester of α-bromoisovaleric acid; by condensation of acetone with malonic acid or bromoacetic ester; by oxidation of mesityl oxide with sodium hypochlorite.
• Uses: Chemical Intermediates.

Technology Process of 3,3-Dimethylacrylic acid

There total 120 articles about 3,3-Dimethylacrylic 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: 98.0%

3,3-dimethyl acrylaldehyde (107-86-8) → 3-Methylbutenoic acid (541-47-9)

Guidance literature:

With 4H₃N*4H⁽¹⁺⁾*CuMo₆O₁₈(OH)6^(4-); water; oxygen; sodium carbonate; at 50 ℃; for 12h; under 760.051 Torr;

DOI:10.1002/cctc.201701599

Reference yield: 95.0%

(Z)-3-iodobut-2-enoic acid (34450-60-7) + methylmagnesium bromide (75-16-1) → 3-Methylbutenoic acid (541-47-9)

Guidance literature:

methylmagnesium bromide; With zinc dibromide; In diethyl ether; at 25 ℃;

(Z)-3-iodobut-2-enoic acid; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; at 25 ℃; for 12h;

DOI:10.1055/s-2002-20971

Reference yield: 92.0%

carbon monoxide (201230-82-2) + 3-hydroxy-2-methyl-1-propene (513-42-8) → 3-Methylbutenoic acid (541-47-9)

Guidance literature:

1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,2-dimethoxyethane; at 190 ℃; for 48h; under 30400 Torr;

DOI:10.1021/jo00018a029

upstream raw materials:

4,4-dimethyloxetan-2-one

ethyl 2-bromoisovalerate

cycl-isopropylidene malonate

acetic anhydride

Downstream raw materials:

α-bromo-β-methoxy-isovaleric acid

3,3-dimethyl-4-oxo-heptanoic acid

2-methyl-4-heptanone

3-methyl-crotonic acid sec-butyl ester

Refernces

• 1、 Sargsyan, M. S.,Mkrtumyan, S. A.,Avakyan, O. V.,Manukyan, A. T.,Gevorkyan, A. A.. "β,β-DIMETHYLACRYLIC ACID". . p. 270 - 271. Retrieved 1991.
• 2、 Hennion,O'Brien. "-". . p. 2933. Retrieved 1949.
• 3、 Br?nstrup, Mark,Fuchs, Hazel Leanne Sarah,Grunenberg, J?rg,Jimidar, Claire Cheyenne,Karge, Bianka,Klahn, Philipp. "Masked Amino Trimethyl Lock (H2N-TML) Systems: New Molecular Entities for the Development of Turn-On Fluorophores and Their Application in Hydrogen Sulfide (H2S) Imaging in Human Cells". . . Retrieved 2021/11/10.
• 4、 Baltz, Rachel,Bojack, Guido,Dittgen, Jan,Fischer, Christian,Frackenpohl, Jens,Freigang, J?rg,Getachew, Rahel,Grill, Erwin,Helmke, Hendrik,Hohmann, Sabine,Lange, Gudrun,Lehr, Stefan,Porée, Fabien,Schmidt, Jana,Schmutzler, Dirk,Yang, Zhenyu. "Synthesis and Exploration of Abscisic Acid Receptor Agonists Against Dought Stress by Adding Constraint to a Tetrahydroquinoline-Based Lead Structure". . p. 3442 - 3457. Retrieved 2021/06/25.