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06061

Sigma-Aldrich

Allyl phenyl sulfone

purum, ≥98.0% (GC)

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Synonym(s):
(2-Propen-1-ylsulfonyl)benzene, (2-Propenylsulfonyl)benzene, (Allylsulfonyl)benzene, Phenyl 2-propenyl sulfone
Linear Formula:
C6H5SO2CH2CH=CH2
CAS Number:
16212-05-8
Molecular Weight:
182.24
Beilstein:
1863561
EC Number:
240-338-8
MDL number:
MFCD00014739
UNSPSC Code:
12352100
PubChem Substance ID:
329748204
NACRES:
NA.22

grade

purum

Quality Level

200

Assay

≥98.0% (GC)

form

liquid

refractive index

n20/D 1.548 (lit.)
n20/D 1.548

bp

110-113 °C/0.5 mmHg (lit.)

density

1.189 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C=CCS(=O)(=O)c1ccccc1

InChI

1S/C9H10O2S/c1-2-8-12(10,11)9-6-4-3-5-7-9/h2-7H,1,8H2

InChI key

KYPIULIVYSQNNT-UHFFFAOYSA-N

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Application

Possible usages of allyl phenyl sulfone:
  • It can undergo isomerization by the nonionic proazaphosphatrane catalysts under mild reaction conditions.
  • It can react with epoxymesylate to give cycloalkane derivative. This method has been employed in the synthesis of marine eicosanoid bacillariolides I-III.
  • It can undergo electrocatalytic additions to vinyl sulfones catalyzed by an electrogenerated base.

Starting material for the preparation of 1-alkyl-2-methylethenes; Michael additions to enones; Synthesis of α,β-unsaturated nitriles

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

235.4 °F

Flash Point(C)

113 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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Proazaphosphatrane P (RNCH2CH2) 3N (R= Me, i?Pr)?Catalyzed Isomerization of Allylaromatics, Allyl Phenyl Sulfide, Allyl Phenyl Sulfone, and bis?Allylmethylene Double Bond?Containing Compounds
Yu Z, et al.
Advanced Synthesis & Catalysis, 348(1?2), 111-117 (2006)
M. Hirama
Tetrahedron Letters, 22, 1905-1905 (1981)
One-Pot Synthesis of Cycloalkane Derivatives using Allyl Phenyl Sulfone and Epoxymesylate.
Miyaoka H, et al.
Tetrahedron, 56(41), 8077-8081 (2000)
D.F. Taber et al.
The Journal of Organic Chemistry, 46, 4817-4817 (1981)
Highly efficient, catalytic bis addition reactions of allyl phenyl sulfone to vinyl sulfones.
Felton G A & Bauld N L
Tetrahedron Letters, 45(25), 4841-4845 (2004)

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