Ethyl 3,3-dimethylacrylate

Base Information

• Chemical Name: Ethyl 3,3-dimethylacrylate
• CAS No.: 638-10-8
• Molecular Formula: C7H12O2
• Molecular Weight: 128.171
• Hs Code.: 29161900
• European Community (EC) Number: 211-319-1
• NSC Number: 99208,61853
• UNII: 2Z69LO3855
• DSSTox Substance ID: DTXSID0060931
• Nikkaji Number: J108.762B
• Wikidata: Q27255837
• Mol file: 638-10-8.mol

Synonyms:3,3-dimethylacrylic acid ethyl ester

Chemical Property of Ethyl 3,3-dimethylacrylate

Chemical Property:

• Appearance/Colour: liquid
• Vapor Pressure: 3.32mmHg at 25°C
• Melting Point: -62.68°C (estimate)
• Refractive Index: n20/D 1.436(lit.)
• Boiling Point: 153.499 °C at 760 mmHg
• Flash Point: 46.278 °C
• PSA: 26.30000
• Density: 0.909 g/cm³
• LogP: 1.51570
• Water Solubility.: Insoluble in water
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 128.083729621
• Heavy Atom Count: 9
• Complexity: 121

Purity/Quality:

99.9% ^*data from raw suppliers

Ethyl3-Methyl-2-butenoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-29-33-28-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)C=C(C)C
• Uses: Ethyl 3,3-dimethylacrylate was used in the synthesis of:3-benzylmercupto-3-methylbutanoic acid ethylestercis-2-cyano-3,3-dimethylcyclopropanecarboxylic acid, precursor for the synthesis of cis-pyrethroids1-[13CD3]-9-cis-retinoic acid

Technology Process of Ethyl 3,3-dimethylacrylate

There total 53 articles about Ethyl 3,3-dimethylacrylate 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: 90.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + acetone (67-64-1) → ethyl 3-methylbut-2-enoate (638-10-8)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.25h; Inert atmosphere;

acetone; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol8018852

Reference yield: 88.8%

ethanol (64-17-5) + 3-Methylbutenoic acid (541-47-9) → ethyl 3-methylbut-2-enoate (638-10-8)

Guidance literature:

toluene-4-sulfonic acid; In tetrachloromethane; for 24h; Heating;

DOI:10.1002/ardp.19803130914

Reference yield: 87.0%

2-methyl-3-bromo-1-propene (1458-98-6) + carbon monoxide (201230-82-2) + sodium ethanolate (141-52-6) → ethyl 3-methylbut-2-enoate (638-10-8)

Guidance literature:

Na₂PdCl₄-dppe; In ethanol; at 50 ℃; for 2h;

upstream raw materials:

1-ethyl-piperidine

pyridine

monoethyl isopropylidenemalonate

pyridinium picrate

Downstream raw materials:

5t-[2]furyl-3-methyl-penta-2c,4-dienoic acid

2,4-Dimethyl-1,3-pentadiene

2,2-dimethylsuccinic acid

13-cis-retinoic acid

Refernces

• 1、 Hammock et al.. "". . p. 517,520. Retrieved 1977.
• 2、 Alektiar, Sara N.,Wickens, Zachary K.. "Photoinduced Hydrocarboxylation via Thiol-Catalyzed Delivery of Formate across Activated Alkenes". supporting information. p. 13022 - 13028. Retrieved 2021/09/03.
• 3、 Liu, Feng,Liu, Jia-Li,tu, Jia-Lin. "Visible-Light-Promoted Intramolecular α-Allylation of Aldehydes in the Absence of Sacrificial Hydrogen Acceptors". supporting information. p. 7369 - 7372. Retrieved 2020/10/05.