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MilliporeSigma

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:
6117-91-5
Molecular Weight:
72.11
Beilstein/REAXYS Number:
1361395
EC Number:
228-086-7
MDL number:
MFCD00002923
UNSPSC Code:
12352100
PubChem Substance ID:
24893079
NACRES:
NA.22

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Quality Level

200

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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1 of 4

This Item
P50803453021459798
Crotyl alcohol, mixture of cis and trans 96%

Sigma-Aldrich

C86006

Crotyl alcohol, mixture of cis and trans

Propargyl alcohol 99%

Sigma-Aldrich

P50803

Propargyl alcohol

Allyl alcohol ≥98.5%

Sigma-Aldrich

453021

Allyl alcohol

Allyl alcohol ≥98.5%

Sigma-Aldrich

459798

Allyl alcohol

assay

96%

assay

99%

assay

≥98.5%

assay

≥98.5%

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

200

density

0.845 g/mL at 25 °C (lit.)

density

0.963 g/mL at 25 °C (lit.)

density

0.854 g/mL at 25 °C (lit.)

density

0.854 g/mL at 25 °C (lit.)

bp

121-122 °C (lit.)

bp

114-115 °C (lit.)

bp

96-98 °C (lit.)

bp

96-98 °C (lit.)

refractive index

n20/D 1.427 (lit.)

refractive index

n20/D 1.432 (lit.)

refractive index

n20/D 1.412 (lit.)

refractive index

n20/D 1.412 (lit.)

form

liquid

form

-

form

-

form

-

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]

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCC3060
BCBQ0439V
BCBH4974V
1422501V
BCBC7711V

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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)
Total synthesis of discodermolide: optimization of the effective synthetic route.
de Lemos E, et al.
Chemistry?A European Journal , 14(35), 11092-11112 (2008)
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
View All Related Papers

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