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65980

Sigma-Aldrich

(S)-(−)-2-Methylbutanol

≥95.0% (sum of enantiomers, GC)

Synonym(s):

(S)-(−)-2-Methyl-1-butanol, Active amyl alcohol

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About This Item

Empirical Formula (Hill Notation):
C5H12O
CAS Number:
Molecular Weight:
88.15
Beilstein/REAXYS Number:
1718809
EC Number:
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥95.0% (sum of enantiomers, GC)

optical activity

[α]20/D −6.3±0.5°, c = 10% in ethanol

refractive index

n/D 1.41
n20/D 1.411

bp

129-131 °C (lit.)

density

0.819 g/mL at 20 °C (lit.)
0.811 g/mL at 25 °C

functional group

hydroxyl

storage temp.

2-8°C

SMILES string

CC[C@H](C)CO

InChI

1S/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3/t5-/m0/s1

InChI key

QPRQEDXDYOZYLA-YFKPBYRVSA-N

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General description

rest mainly 3-methyl-1-butanol

Application

(S)-(-)-2-Methylbutanol can be used as a reactant to prepare:
  • Methylbutyl-2-(3-thienyl)acetate (MBTA) by esterification reaction with 3-thiophene acetic acid in the presence of an acid catalyst.
  • (2S)-2-Methyl-1-butanesulfenyl chloride by reacting with thioacetic acid using Mitsunobu reaction conditions.
  • (+)-Violapyrone C and (-)-myxalamide A.

pictograms

FlameExclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Inhalation - Flam. Liq. 3 - STOT SE 3

target_organs

Respiratory system

supp_hazards

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

108.5 °F

flash_point_c

42.5 °C

ppe

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


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Concise Total Synthesis of (-)-Myxalamide A
Fujita K et al.
Angewandte Chemie (International ed. in English), 51(29), 7271-7274 (2012)
Total Synthesis and Configurational Validation of (+)-Violapyrone C
Lee JS, et al.
European Journal of Organic Chemistry, 2014(21), 4472-4476 (2014)

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