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192619

Sigma-Aldrich

Tiglic aldehyde

≥96%

Synonym(s):

(E)-2-Methylbut-2-enal, trans-2,3-Dimethylacrolein, trans-2-Methyl-2-butenal, Tiglinaldehyde

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About This Item

Linear Formula:
CH3CH=C(CH3)CHO
CAS Number:
497-03-0
Molecular Weight:
84.12
Beilstein:
1698207
MDL number:
MFCD00006977
UNSPSC Code:
12352100
PubChem Substance ID:
24851554
NACRES:
NA.22

Assay

≥96%

form

liquid

refractive index

n20/D 1.448 (lit.)

bp

116-119 °C/752 mmHg (lit.)

density

0.869 g/mL at 20 °C
0.871 g/mL at 25 °C (lit.)

functional group

aldehyde

SMILES string

C\C=C(/C)C=O

InChI

1S/C5H8O/c1-3-5(2)4-6/h3-4H,1-2H3/b5-3+

InChI key

ACWQBUSCFPJUPN-HWKANZROSA-N

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Application

Tiglic aldehyde was used in the concise total synthesis of 7-demethylpiericidin A1. It was used as starting reagent during the synthesis of:
  • alkyl-branched tetraene hydrocarbons, pheromone component for dried fruit beetle
  • E,E-2,4-dimethyl-2,4-hexa dienal, volatile constituents of the defensive secretions of Leiobunum nigripalpi
  • 4-methyl-2,4-hexadiene-1-ol

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

69.8 °F - closed cup

Flash Point(C)

21 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR7491
SHBR8905
SHBR3269
SHBQ4046
0000240414

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T H Jones et al.
Proceedings of the National Academy of Sciences of the United States of America, 74(2), 419-422 (1977-02-01)
Analyses of the chief volatile constituents of the defensive secretions of three oplionids were carried out. Leiobunum nigripalpi produces three closely related C7 compounds: E-4-methyl-4-hexen-3-one(I), 4-methylhexan-3-one(II), and 4-methylhexan-3-ol(III), along with E-4-methyl-4-hepten-3-one(IV), E,E-2,4-dimethylhexa-2,4-dienal(IX), and a minor, unidentified component. L. leiopenis secretion
Synthesis of 1, 2-and 1, 4-disubstituted tricarbonyl (pentadienyl) iron (+ 1) cations and reactions with heteroatom nucleophiles.
Donaldson WA, et al
Organometallics, 12(4), 1174-1179 (1993)
Synthesis of nitidulid beetle pheromones: alkyl-branched tetraene hydrocarbons.
Bartelt RJ, et al.
Journal of Agricultural and Food Chemistry, 38(12), 2192-2196 (1990)
Katie A Keaton et al.
Journal of the American Chemical Society, 128(2), 408-409 (2006-01-13)
A concise total synthesis of 7-demethylpiericidin A1 has been completed. The synthesis features a titanium(II)-mediated cyclization of a (silyloxy)enyne as the key step and proceeds in nine steps from tiglic aldehyde.
Hasmik Grigoryan et al.
Carcinogenesis, 39(5), 661-668 (2018-03-15)
Although benzene has long been recognized as a cause of human leukemia, the mechanism by which this simple molecule causes cancer has been problematic. A complicating factor is benzene metabolism, which produces many reactive intermediates, some specific to benzene and
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