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324663

Sigma-Aldrich

1,4-Pentadien-3-ol

contains 0.4% hydroquinone as stabilizer, ≥96%

Synonym(s):
Divinyl carbinol
Linear Formula:
CH2=CHCH(OH)CH=CH2
CAS Number:
Molecular Weight:
84.12
Beilstein:
1735809
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

≥96%

contains

0.4% hydroquinone as stabilizer

refractive index

n20/D 1.445 (lit.)

bp

115-116 °C (lit.)

density

0.865 g/mL at 25 °C (lit.)

SMILES string

OC(C=C)C=C

InChI

1S/C5H8O/c1-3-5(6)4-2/h3-6H,1-2H2

InChI key

ICMWSAALRSINTC-UHFFFAOYSA-N

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Related Categories

Packaging

5, 25 g in glass bottle

Application

Substrate employed in a synthesis of amino-substituted dienes via a bismuth-catalyzed SNi displacement of alcohols by sulfonamide nucleophiles.
Starting material for asymmetric epoxidation.
Useful building block in natural product synthesis.

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

89.6 °F - closed cup

Flash Point(C)

32 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Tetrahedron Asymmetry, 4, 1533-1533 (1993)
Masanori Imai et al.
The Journal of organic chemistry, 69(4), 1144-1150 (2004-02-14)
Intermolecular hydroacylation between salicylaldehydes 1, 26-40 and 1,4-penta- or 1,5-hexadienes 4-13 by Rh-catalyst proceeded under mild reaction conditions to give a mixture of iso- and normal-hydroacylated products 14-25, 41-55, and 57-60. In the hydroacylation reaction, chelation of both salicylaldehyde and
Chin. J. Chem., 9, 381-381 (1991)
P Andrew Evans et al.
Journal of the American Chemical Society, 125(48), 14702-14703 (2003-12-04)
The enantioselective total synthesis of the annonaceous acetogenin (-)-mucocin (1) was accomplished using a triply convergent 12-step sequence (longest linear sequence) in 13.6% overall yield. This represents the first application of the temporary silicon-tethered (TST) ring-closing metathesis (RCM) cross-coupling reaction
Nakcheol Jeong et al.
Chemical communications (Cambridge, England), (9), 1134-1135 (2004-04-30)
Desymmetrization of the meso dienynes, such as propargyl 1-vinylallyl N-tosylamides (1a-c) and propargyl 1-vinylallyl ethers (1d-e), by asymmetric Pauson-Khand type reaction catalysts was studied. The corresponding vinyl substituted bicyclic pentenones (2 and 3) were obtained with high diastereoselectivity and enantioselectivity.

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