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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)

Quality Level

100

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN7245
MKCJ3952
MKCF1001
MKBZ5978V
MKBV1516V

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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
Denise Biagini et al.
Talanta, 200, 145-155 (2019-05-01)
When working with humid gaseous samples, the amount of water vapour collected in a needle trap along with volatile analytes may vary from sample to sample and decrease during the storage. This has a major impact on desorption efficiency and
Henrik G Kjaergaard et al.
The journal of physical chemistry. A, 116(24), 5763-5768 (2012-03-29)
We investigate the oxidation of methacryloylperoxy nitrate (MPAN) and methacrylicperoxy acid (MPAA) by the hydroxyl radical (OH) theoretically, using both density functional theory [B3LYP] and explicitly correlated coupled cluster theory [CCSD(T)-F12]. These two compounds are produced following the abstraction of
Isoprene and its oxidation products methyl vinyl ketone, methacrolein, and isoprene related peroxides measured online over the tropical rain forest of Surinam in March 1998.
Warneke C, et al.
Journal of Atmospheric Chemistry, 38(2), 167-185 (2001)
Eeva K Kemppainen et al.
Organic letters, 14(4), 1086-1089 (2012-02-03)
Enantioselective iminium-catalyzed reactions with acrolein and methacrolein are rare. A catalytic enantioselective Mukaiyama-Michael reaction that readily accepts acrolein or methacrolein as substrates, affording the products in good yields and 91-97% ee, is presented. As an application of the methodology, an
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