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162353

Sigma-Aldrich

3-Methyl-2-buten-1-ol

99%

Synonym(s):

3,3-Dimethylallyl alcohol, Prenol

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About This Item

Linear Formula:
(CH3)2C=CHCH2OH
CAS Number:
556-82-1
Molecular Weight:
86.13
Beilstein/REAXYS Number:
1633479
EC Number:
209-141-4
MDL number:
MFCD00002916
UNSPSC Code:
12352100
eCl@ss:
39020334
PubChem Substance ID:
24849980
NACRES:
NA.22

vapor pressure

1.4 mmHg ( 20 °C)

Quality Level

100

assay

99%

form

liquid

expl. lim.

16.3 %

refractive index

n20/D 1.443 (lit.)

bp

140 °C (lit.)

density

0.848 g/mL at 25 °C (lit.)

functional group

hydroxyl

SMILES string

C\C(C)=C\CO

InChI

1S/C5H10O/c1-5(2)3-4-6/h3,6H,4H2,1-2H3

InChI key

ASUAYTHWZCLXAN-UHFFFAOYSA-N

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General description

3-Methyl-2-buten-1-ol reacts with nitrosocarbonyl benzene to yield 5-hydroxy-isoxazolidines. It is commonly used as fragrance ingredient.

Application

3-Methyl-2-buten-1-ol was used as starting reagent during asymmetric total syntheses of (R)-(+)- and (S)-(-)-umbelactone via Sharpless asymmetric epoxidation reaction.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

124.7 °F - closed cup

flash_point_c

51.5 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ9976
STBJ9204
06311KC069
08807JE
07815EE

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Anastasia Zerva et al.
Molecules (Basel, Switzerland), 23(9) (2018-09-22)
Feruloyl esterases (FAEs, E.C. 3.1.1.73) are biotechnologically important enzymes with several applications in ferulic acid production from biomass, but also in synthesis of hydroxycinnamic acid derivatives. The use of such biocatalysts in commercial processes can become feasible by their immobilization
Huawei Liu et al.
Chirality, 18(4), 223-226 (2006-03-08)
The asymmetric total syntheses of (R)-(+)- and (S)-(-)-umbelactone were achieved by using the Sharpless asymmetric epoxidation reaction to generate the stereogenic center and a ring-closing metathesis (RCM) for the formation of the lactone structure. Starting from 3-methyl-2-buten-1-ol, the asymmetric total
Alvaro Acosta-Serrano et al.
Eukaryotic cell, 3(2), 255-263 (2004-04-13)
Concanavalin A (ConA) kills the procyclic (insect) form of Trypanosoma brucei by binding to its major surface glycoprotein, procyclin. We previously isolated a mutant cell line, ConA 1-1, that is less agglutinated and more resistant to ConA killing than are
Yi-Fan Chang et al.
The Journal of organic chemistry, 73(18), 7197-7203 (2008-08-19)
Solid-phase organic synthesis of polyprenols with a traceless sulfone linker is described. The polymer-bound benezenesulfinate is first linked with the "tail" building blocks of isoprenyl chlorides via S-alkylation. With use of dimsyl anion as an appropriate base, the polymer-bound alpha-sulfonyl
Geetu Singh et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 14(12), 792-798 (2007-08-11)
Ethanol extract of Coccinia grandis (L.) Voigt showed significant triglyceride (TG) and cholesterol-lowering effects in dyslipidemic hamster model. Ethanolic extract was fractionated into chloroform, n-butanol and water-soluble fractions and were evaluated. Activity was proved to be concentrated in chloroform-soluble fraction.
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