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540021

Sigma-Aldrich

(S)-(−)-Propylene oxide

99%

Synonym(s):

(S)-(−)-1,2-Epoxypropane, (S)-(−)-Methyloxirane

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About This Item

Empirical Formula (Hill Notation):
C3H6O
CAS Number:
16088-62-3
Molecular Weight:
58.08
Beilstein:
79765
EC Number:
240-241-0
MDL number:
MFCD00064312
UNSPSC Code:
12352005
PubChem Substance ID:
24878433
NACRES:
NA.22

vapor density

2 (vs air)

vapor pressure

8.59 psi ( 20 °C)

Assay

99%

autoignition temp.

1378 °F

expl. lim.

37 %

refractive index

n20/D 1.366 (lit.)

bp

33-34 °C (lit.)

density

0.829 g/mL at 20 °C (lit.)

SMILES string

C[C@H]1CO1

InChI

1S/C3H6O/c1-3-2-4-3/h3H,2H2,1H3/t3-/m0/s1

InChI key

GOOHAUXETOMSMM-VKHMYHEASA-N

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Application

  • (S)-(−)-Propylene oxide undergoes ring-opening upon treating with nucleophiles such as Grignard reagents or organolithium compounds to yield corresponding secondary alcohols.
  • It can be used in the synthesis of ligands to prepare of Pb(II) based coordination nets for the fabrication of white light-emitting diode materials.
  • It is a key starting material for the total synthesis of arenolide and (+)-aspicilin.

Legal Information

Manufactured under license by Sterling Pharma Solutions Limited, using Jacobsen HKR technology.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Flam. Liq. 1 - Muta. 1B - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-34.6 °F - closed cup

Flash Point(C)

-37 °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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Wittig cyclization of ?-hydroxy hemiacetals: Synthesis of (+)-aspicilin.
Schmidt R, et al.
The Journal of Organic Chemistry, 82(17), 9126-9132 (2017)
Synthesis and Stereochemical Assignment of Arenolide.
Liu X, et al.
Organic Letters, 20(7), 1898-1901 (2018)
White light emission and second harmonic generation from secondary group participation (SGP) in a coordination network.
He J, et al.
Journal of the American Chemical Society, 134(3), 1553-1559 (2012)
Amanda S Hakemian et al.
Biochemistry, 47(26), 6793-6801 (2008-06-11)
Particulate methane monooxygenase (pMMO) is a membrane-bound metalloenzyme that oxidizes methane to methanol in methanotrophic bacteria. The nature of the pMMO active site and the overall metal content are controversial, with spectroscopic and crystallographic data suggesting the presence of a

Chromatograms

suitable for GC

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