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133035

Sigma-Aldrich

Methacrolein

95%

Synonym(s):

Methacrylaldehyde

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About This Item

Linear Formula:
H2C=C(CH3)CHO
CAS Number:
78-85-3
Molecular Weight:
70.09
Beilstein:
1209258
EC Number:
201-150-1
MDL number:
MFCD00006974
UNSPSC Code:
12352100
PubChem Substance ID:
24848091
NACRES:
NA.22

vapor density

2.4 (vs air)

vapor pressure

121 mmHg ( 20 °C)
13.44 psi ( 55 °C)
5.35 psi ( 20 °C)

Assay

95%

form

liquid

refractive index

n20/D 1.416 (lit.)

bp

68-70 °C (lit.)

mp

−81 °C (lit.)

density

0.85 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

[H]C(=O)C(C)=C

InChI

1S/C4H6O/c1-4(2)3-5/h3H,1H2,2H3

InChI key

STNJBCKSHOAVAJ-UHFFFAOYSA-N

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General description

Methacrolein on oxidation over heteropoly acid catalysts (mainly 12-molybdophosphoric acid) at 300°C yields methacrylic acid. It is the major product of isoprene oxidation.

Application

Methacrolein was used to study the effect of parts per billion levels of limonene oxidation products and the terpene oxidation product, methacrolein on human eye blink frequency. It was also used in determination of rate constants and the products of the reactions between atomic chlorine and acrolein, methacrolein and methyl vinyl ketone.

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Flam. Liq. 2 - Muta. 2 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

5.0 °F - closed cup

Flash Point(C)

-15 °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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Sigma-Aldrich

304077

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Acrolein dimethyl acetal 98%

Sigma-Aldrich

190543

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Michael N Paddon-Row et al.
The Journal of organic chemistry, 74(2), 861-868 (2008-12-11)
The cationic oxazaborolidine-catalyzed Diels-Alder reactions of butadiene and a series of five dienophiles have been studied using density functional theory (B3LYP/6-31G(d)). In each case, the computational results successfully reproduce the experimentally observed sense of stereoinduction and enantiomeric ratio. The computed
S T Larsen et al.
Toxicology letters, 114(1-3), 197-202 (2000-03-14)
The acute respiratory effects of airborne exposure to methacrolein were studied in a recent refinement of the standard test method with mice (ASTM, 1984. American Society for Testing and Materials, Philadelphia). Irritation of the upper respiratory tract caused a concentration-dependent
John D Crounse et al.
The journal of physical chemistry. A, 116(24), 5756-5762 (2012-03-29)
Peroxy radicals formed by addition of OH and O(2) to the olefinic carbon atoms in methacrolein react with NO to form methacrolein hydroxy nitrate and hydroxyacetone. We observe that the ratio of these two compounds, however, unexpectedly decreases as the
Catalysis by heteropoly compounds: IV. Oxidation of methacrolein to methacrylic acid over 12-molybdophosphoric acid.
Konishi Y, et al.
J. Catal., 77(1), 169-179 (1982)
Daniel Carmona et al.
Journal of the American Chemical Society, 127(38), 13386-13398 (2005-09-22)
The rhodium and iridium Lewis-acid cations [(eta(5)-C(5)Me(5))M{(R)-Prophos}(H(2)O)](2+) ((R)-Prophos = 1,2-bis(diphenylphosphino)propane) efficiently catalyze the enantioselective 1,3-dipolar cycloaddition of nitrones to methacrolein. Reactions occur with perfect endo selectivity and with enantiomeric excesses up to 96%. Intermediates [(eta(5)-C(5)Me(5))M{(R)-Prophos}(methacrolein)](SbF(6))(2) (M = Rh (3), Ir
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