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324663

Sigma-Aldrich

1,4-Pentadien-3-ol

contains 0.4% hydroquinone as stabilizer, ≥96%

Synonym(s):

Divinyl carbinol

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About This Item

Linear Formula:
CH2=CHCH(OH)CH=CH2
CAS Number:
922-65-6
Molecular Weight:
84.12
Beilstein:
1735809
MDL number:
MFCD00008633
UNSPSC Code:
12352100
PubChem Substance ID:
24859459
NACRES:
NA.22

Assay

≥96%

form

liquid

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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Application

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

Signal Word

Warning

Hazard Statements

H226,H302,H411

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - 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

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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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.
Tetrahedron Asymmetry, 4, 1533-1533 (1993)
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