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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.)

functional group

aldehyde

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
MKCT0274
MKCN7245
MKCJ3952
MKCF1001
MKBZ5978V

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Sigma-Aldrich

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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)
Jacob Klenø Nøjgaard et al.
Toxicology letters, 156(2), 241-251 (2005-03-02)
Oxidation products of terpenes (e.g. limonene) contain unidentified irritants, which may be responsible for a fraction of the reported eye and airway complaints in indoor environments. Here we report exposure to parts per billion (ppb) levels of limonene oxidation products
Carmen Barba et al.
The Journal of organic chemistry, 71(26), 9831-9840 (2006-12-16)
A B3LYP/6-31G* study has been carried out for the reactions of methacrolein with cyclopentadiene, parent nitrone, 1-pyrroline-1-oxide, and (Z)-C,N-diphenylnitrone, in which the coordination of a Lewis acid (borane) and the solvent polarity (dichloromethane) have been taken into account. Calculated activation
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