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C86006

Sigma-Aldrich

Crotyl alcohol, mixture of cis and trans

96%

Synonym(s):

2-Buten-1-ol

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25 ML
$164.00
100 ML
$174.00

About This Item

Linear Formula:
CH3CH=CHCH2OH
CAS Number:
Molecular Weight:
72.11
Beilstein/REAXYS Number:
1361395
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

$164.00


Available to ship onApril 22, 2025Details


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Quality Level

assay

96%

form

liquid

refractive index

n20/D 1.427 (lit.)

bp

121-122 °C (lit.)

density

0.845 g/mL at 25 °C (lit.)

SMILES string

C\C=C\CO

InChI

1S/C4H8O/c1-2-3-4-5/h2-3,5H,4H2,1H3/b3-2+

InChI key

WCASXYBKJHWFMY-NSCUHMNNSA-N

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Application

Crotyl alcohol can be used as a starting material in the synthesis of antitumor agents such as 14-azacamptothecin[1] and 10, 11-methylenedioxy-14-azacamptothecin.[2] It can also be used as a precursor in the total synthesis of discodermolide.[3]

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Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

93.2 °F - closed cup

flash_point_c

34 °C - closed cup

ppe

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


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Synthesis of 14-azacamptothecin, a water-soluble topoisomerase I poison.
Rahier N J, et al.
Organic Letters, 7(5), 835-837 (2005)
Synthesis of optically active β-alkyl aspartate via [3, 3] sigmatropic rearrangement of α-acyloxytrialkylsilane.
Sakaguchi K, et al.
Tetrahedron Letters, 45(30), 5869-5872 (2004)
Evaluation of the role of acetaldehyde in the actions of ethanol on gluconeogenesis by comparison with the effects of crotonol and crotonaldehyde.
A I Cederbaum et al.
Alcoholism, clinical and experimental research, 6(1), 100-109 (1982-01-01)
High-activity, single-site mesoporous Pd/Al2O3 catalysts for selective aerobic oxidation of allylic alcohols.
Simon F J Hackett et al.
Angewandte Chemie (International ed. in English), 46(45), 8593-8596 (2007-10-06)
Total synthesis of discodermolide: optimization of the effective synthetic route.
de Lemos E, et al.
Chemistry?A European Journal , 14(35), 11092-11112 (2008)

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