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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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¥109,000

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5 G
¥28,800
25 G
¥109,000

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

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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.[1][2]
Substrate employed in a synthesis of amino-substituted dienes via a bismuth-catalyzed SNi displacement of alcohols by sulfonamide nucleophiles.[3]
Useful building block in natural product synthesis.[4][5][6]

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

324663-VAR:
324663-BULK:
324663-5G:4548173983530
324663-25G:4548173983523

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW1321
MKCT4910
MKCR0425
MKCL8781
MKCK8537

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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
Chin. J. Chem., 9, 381-381 (1991)
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
Bismuth-catalyzed direct substitution of the hydroxy group in alcohols with sulfonamides, carbamates, and carboxamides.
Hongbo Qin et al.
Angewandte Chemie (International ed. in English), 46(3), 409-413 (2006-12-06)
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