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:

99.0% min ^*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: 3-Methylcrotonic acid, also known as 3-methylbut-2-enoic acid or 3,3-dimethylacrylic acid, is an organic compound which is a methyl-branched fatty acid, characterized by a but-2-enoic acid backbone with a methyl substituent at position 3. 3-Methylcrotonic acid is classified as a monounsaturated fatty acid, a short-chain fatty acid, a methyl-branched fatty acid, and an alpha,beta-unsaturated monocarboxylic acid.
• Uses and Mechanism of Action: 3-Methylcrotonic acid serves as a precursor in the biosynthesis of gibberellic acid by certain fungi, such as Fusarium moniliforme. It is also utilized in organic synthesis, particularly in the stereospecific isoprenoid homologation reactions for the synthesis of compounds like farnesol. In the biosynthesis of gibberellic acid, 3-Methylcrotonic acid, along with acetate, acts as a precursor for the formation of gibberellic acid by Fusarium moniliforme. In organic synthesis, it undergoes reactions such as γ-alkylation to produce various isomers of farnesol.

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-methyl-3-(phenylmethylthio)butanoic acid

3-(2-methoxy-4-methyl-phenyl)-3-methyl-butyric acid

3-methyl-3-phenylbutanoic acid

Refernces

NOVEL "ONE-POT" PREPARATION OF TETRAHYDROBENZODIPYRAN-4-ONES. APPLICATION TO THE SYNTHESIS OF PRECOCENE ANALOGUES WITH CONDENSED DIHYDROPYRAN RINGS

10.1016/0040-4020(82)85025-4

The research details a novel one-pot preparation method for synthesizing tetrahydrobenzodipyran-4-ones and their subsequent conversion to dihydrobenzodipyrans, which are precocene analogues. The synthesis involves the sequential condensation of resorcinols with 3,3-dimethylacrylic acid and 1,3-dichloro-3-methylbutane in methanesulphonic acid, which acts as both solvent and catalyst. The study explores the synthesis of various substituted tetrahydrobenzodipyran-4-ones and their conversion to dihydrobenzodipyrans, with yields and reaction conditions optimized for different starting materials. The results provide a new synthetic route for these compounds, which have potential applications in insect control due to their insect anti-juvenile hormone (AJH) activity.