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Merck
CN

324663

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24859459
MDL number:
MFCD00008633
Beilstein/REAXYS Number:
1735809

Key Documents

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Product Name

1,4-Pentadien-3-ol, contains 0.4% hydroquinone as stabilizer, ≥96%

InChI

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

SMILES string

OC(C=C)C=C

InChI key

ICMWSAALRSINTC-UHFFFAOYSA-N

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

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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.

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Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

89.6 °F - closed cup

flash_point_c

32 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCW1321
MKCT4910
MKCR0425
MKCL8781
MKCK8537

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Chin. J. Chem., 9, 381-381 (1991)
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
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
Tetrahedron Asymmetry, 4, 1533-1533 (1993)
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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