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Key Documents

194328

Sigma-Aldrich

Ethyl 3,3-dimethylacrylate

98%

Synonym(s):

Ethyl 3-methylcrotonate

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About This Item

Linear Formula:
(CH3)2C=CHCO2C2H5
CAS Number:
Molecular Weight:
128.17
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

form

liquid

refractive index

n20/D 1.436 (lit.)

bp

154-155 °C (lit.)

density

0.922 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)\C=C(\C)C

InChI

1S/C7H12O2/c1-4-9-7(8)5-6(2)3/h5H,4H2,1-3H3

InChI key

UTXVCHVLDOLVPC-UHFFFAOYSA-N

General description

Ion-molecule reactions between the O=P(OCH3)2+phosphonium ions and ethyl 3,3-dimethylacrylate has been investigated by quadrupole ion trap mass spectrometery.

Application

Ethyl 3,3-dimethylacrylate was used in the synthesis of:
  • 3-benzylmercupto-3-methylbutanoic acid ethylester
  • cis-2-cyano-3,3-dimethylcyclopropanecarboxylic acid, precursor for the synthesis of cis-pyrethroids
  • 1-[13CD3]-9-cis-retinoic acid

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

93.2 °F - closed cup

Flash Point(C)

34 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of 1-[13CD3]-9-cis-retinoic acid.
Bennani YL
Journal of Labelled Compounds & Radiopharmaceuticals, 36(8), 755-763 (1995)
[Toxicological characteristics and the establishment of a MPEL for dimethylacrylic acid and its ethyl ether in the air of a work area].
A I Gurova et al.
Gigiena truda i professional'nye zabolevaniia, (4)(4), 52-53 (1985-04-01)
A facile route to a versatile synthon for preparation of cis-pyrethroids.
Babler JH and Invergo BJ.
Tetrahedron Letters, 22(29), 2743-2746 (1981)
Potent odorants of the roasted powder and brew of Arabica coffee.
Blank I, et al.
Zeitschrift fur Lebensmittel-Untersuchung Und -Forschung, 195(3), 239-245 (1992)
Taifo Mahmud et al.
The Journal of biological chemistry, 277(36), 32768-32774 (2002-06-27)
Short chain carboxylic acids are well known as the precursors of fatty acid and polyketide biosynthesis. Iso-fatty acids, which are important for the control of membrane fluidity, are formed from branched chain starter units (isovaleryl-CoA and isobutyryl-CoA), which in turn

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