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Sigma-Aldrich

(S)-(+)-2-Butanol

99%

Synonym(s):

(S)-(+)-sec-Butyl alcohol

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About This Item

Linear Formula:
C2H5CH(OH)CH3
CAS Number:
4221-99-2
Molecular Weight:
74.12
Beilstein:
1718763
EC Number:
224-168-1
MDL number:
MFCD00064281
UNSPSC Code:
12352001
PubChem Substance ID:
24854264
NACRES:
NA.22

vapor density

2.6 (vs air)

vapor pressure

12.5 mmHg ( 20 °C)

Assay

99%

form

liquid

optical activity

[α]20/D +13°, neat

autoignition temp.

761 °F

expl. lim.

9.8 %

refractive index

n20/D 1.397 (lit.)

bp

99-100 °C (lit.)

density

0.803 g/mL at 25 °C (lit.)

SMILES string

CC[C@H](C)O

InChI

1S/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3/t4-/m0/s1

InChI key

BTANRVKWQNVYAZ-BYPYZUCNSA-N

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Application

(S)-(+)-2-Butanol can be used:
  • To synthesize chiral asymmetric perylene diimides (PDI) that spontaneously self-assemble into one-handed nanotubes that are photoconductive or fluorescent in nature.
  • To synthesize bulky chiral vinyl monomers that can be radically polymerized to helical polymers with an excess screw sense.
  • As chiral solvent to study excited state photo transfer of the photoacid, 5,8-dicyano-2-naphthol (DCN2) in chiral environment.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H319,H335,H336

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

75.2 °F - closed cup

Flash Point(C)

24 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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2-Butanol United States Pharmacopeia (USP) Reference Standard

USP

1081829

2-Butanol

2-Butanol Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1563

2-Butanol

(S)-(−)-2-Methylbutanol ≥95.0% (sum of enantiomers, GC)

Sigma-Aldrich

65980

(S)-(−)-2-Methylbutanol

2-Butanol ReagentPlus®, ≥99%

Sigma-Aldrich

B85919

2-Butanol

Excited-state proton transfer in chiral environments. 1. Chiral solvents.
Solntsev KM, et al.
Journal of the American Chemical Society, 124(31), 9046-9047 (2002)
Highly fluorescent one-handed nanotubes assembled from a chiral asymmetric perylene diimide.
Ma X , et al.
Chemical Communications (Cambridge, England), 51(20), 4231-4233 (2015)
Stepwise Formation of Photoconductive Nanotubes through a New Top?Down Method.
Ma X , et al.
Advanced Materials, 27(47), 7746-7751 (2015)
Synthesis and characterization of optically active helical vinyl polymers via free radical polymerization.
Zhi J, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 47(9), 2408-2421 (2009)
Uri Cogan et al.
Chirality, 24(7), 500-505 (2012-05-10)
Supramolecular chiral assemblies of R(-) and S(+) 2-butanol, in their neat form or when dissolved in their nonchiral isomer isobutanol, were evaluated by isothermal titration calorimetry (ITC) ensuing mixing. Dilution of 0.5 M solution of R(-) 2-butanol in isobutanol into
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