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Merck
CN

06061

Allyl phenyl sulfone

purum, ≥98.0% (GC)

Synonym(s):

(2-Propen-1-ylsulfonyl)benzene, (2-Propenylsulfonyl)benzene, (Allylsulfonyl)benzene, Phenyl 2-propenyl sulfone

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About This Item

Linear Formula:
C6H5SO2CH2CH=CH2
CAS Number:
16212-05-8
Molecular Weight:
182.24
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
329748204
EC Number:
240-338-8
Beilstein/REAXYS Number:
1863561
MDL number:
MFCD00014739
Assay:
≥98.0% (GC)
Form:
liquid

Key Documents

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InChI key

KYPIULIVYSQNNT-UHFFFAOYSA-N

InChI

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

SMILES string

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

grade

purum

assay

≥98.0% (GC)

form

liquid

Quality Level

200

bp

110-113 °C/0.5 mmHg (lit.)

density

1.189 g/mL at 25 °C (lit.)

functional group

sulfone

storage temp.

2-8°C

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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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG8620
BCCC9994
BCBV6260
BCBV7594
BCBS8114V

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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)
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)
D. Savoia et al.
Journal of the Chemical Society. Perkin Transactions 1, 123-123 (1977)
D.F. Taber et al.
The Journal of Organic Chemistry, 46, 4817-4817 (1981)
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