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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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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

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 and 10, 11-methylenedioxy-14-azacamptothecin. It can also be used as a precursor in the total synthesis of discodermolide.

pictograms

FlameExclamation mark

signalword

Warning

Hazard Classifications

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

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

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


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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cis-2-Hexen-1-ol 95%

Sigma-Aldrich

224707

cis-2-Hexen-1-ol

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)
Synthesis of 14-azacamptothecin, a water-soluble topoisomerase I poison.
Rahier N J, et al.
Organic Letters, 7(5), 835-837 (2005)
Darby R Schmidt et al.
Organic letters, 5(19), 3535-3537 (2003-09-12)
[structure: see text] A synthesis of the C(15)-C(30) fragment of Dolabelides A and B has been achieved. The recently developed asymmetric silane alcoholysis and tandem silylformylation-crotylsilylation reactions were used as the key steps to establish the C(23)-C(27) 1,5-syn-diol. In addition
Frank R Fontaine et al.
Chemical research in toxicology, 15(8), 1051-1058 (2002-08-20)
Recent confirmation that the toxic unsaturated aldehyde crotonaldehyde (CA) contributes to protein damage during lipid peroxidation confers interest on the molecular actions of this substance. However, since a plethora of structurally related aldehydes form during membrane oxidation, clarifying the toxicological
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)

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