Allyl phenyl sulfone Property

Boiling point:

110-113 °C/0.5 mmHg (lit.)

Density 

1.189 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.548(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

form 

clear liquid

color 

Colorless to Orange to Green

Water Solubility 

insol water; sol most organic solvents.

Sensitive 

Light Sensitive

BRN 

1863561

InChIKey

KYPIULIVYSQNNT-UHFFFAOYSA-N

CAS DataBase Reference

16212-05-8(CAS DataBase Reference)

EPA Substance Registry System

Benzene, (2-propenylsulfonyl)- (16212-05-8)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

WR2400000

F 

8-10

TSCA 

T

HazardClass 

IRRITANT

HS Code 

2930909899

Toxicity

mouse,LD50,intravenous,320mg/kg (320mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02689,

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Allyl phenyl sulfone Chemical Properties,Usage,Production

Chemical Properties

CLEAR COLOURLESS TO FAINTLY YELLOW LIQUID

Uses

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.

Reactivity Profile

Allyl phenyl sulfone could be used as metalated derivatives serve as ambident nucleophiles; reacts as a 1,1-allylic dianion or 1,1-allylic dipole equivalent[1].

Synthesis

The Preparative Method of Allyl phenyl sulfone: from Allyl Bromide and benzenesulfinate in ethanol according to the original procedure is most straightforward and avoids the use of strong-smelling thiols.

References

1. (a) Magnus, P. D. T 1977, 33, 2019. (b) Block, E. Reactions of Organosulfur Compounds; Academic Press: New York, 1978. (c) Biellmann, J.-F.; Ducep, J.-B. OR 1982, 27, 1.
2. Otto, R. LA 1894, 283, 18; Cope, A. C.; Morrison, D. E.; Field, L. JACS 1950, 72, 59. Vennstra, G. E.; Zwaneburg, B. S 1975, 519.