324663
1,4-Pentadien-3-ol
contains 0.4% hydroquinone as stabilizer, ≥96%
Synonym(s):
Divinyl carbinol
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About This Item
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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.)
functional group
hydroxyl
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
Precautionary Statements
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
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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
Tetrahedron Asymmetry, 4, 1533-1533 (1993)
Chin. J. Chem., 9, 381-381 (1991)
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
Bismuth-catalyzed direct substitution of the hydroxy group in alcohols with sulfonamides, carbamates, and carboxamides.
Angewandte Chemie (International ed. in English), 46(3), 409-413 (2006-12-06)
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