MilliporeSigma
All Photos(2)

Documents

213306

Sigma-Aldrich

Phenyl vinyl sulfoxide

95%

Sign Into View Organizational & Contract Pricing

Linear Formula:
C6H5SOCH=CH2
CAS Number:
Molecular Weight:
152.21
Beilstein/REAXYS Number:
2039218
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

95%

form

liquid

refractive index

n20/D 1.585 (lit.)

bp

93-95 °C/0.2 mmHg (lit.)

density

1.139 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C=CS(=O)c1ccccc1

InChI

1S/C8H8OS/c1-2-10(9)8-6-4-3-5-7-8/h2-7H,1H2

InChI key

MZMJHXFYLRTLQX-UHFFFAOYSA-N

Gene Information

Looking for similar products? Visit Product Comparison Guide

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
241717417602556084
vibrant-m

213306

Phenyl vinyl sulfoxide

vibrant-m

241717

Phenyl vinyl sulfone

vibrant-m

417602

2-Chloroethyl phenyl sulfide

vibrant-m

556084

1-Vinyl cyclohexanol

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

form

liquid

form

solid

form

liquid

form

-

density

1.139 g/mL at 25 °C (lit.)

density

-

density

1.174 g/mL at 25 °C (lit.)

density

0.942 g/mL at 25 °C (lit.)

refractive index

n20/D 1.585 (lit.)

refractive index

-

refractive index

n20/D 1.583 (lit.)

refractive index

n20/D 1.478 (lit.)

bp

93-95 °C/0.2 mmHg (lit.)

bp

-

bp

90-91 °C/1 mmHg (lit.)

bp

74 °C/19 mmHg (lit.)

General description

Phenyl vinyl sulfoxide reacts with lithium enolates of ketones at -78°C in THF to yield bicyclo[n.2.0]alkan-1-ols. It also reacts with in situ generated (dialkylamino)magnesium reagent to yield symmetrical β-(dialkylamino)dithioacetals. It participates as an acetylene equivalent in Diels-Alder reactions.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)


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’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 2

1 of 2

Divinyl sulfone contains hydroquinone as inhibitor, ≥96%

Sigma-Aldrich

V3700

Divinyl sulfone

Diphenyl sulfoxide 96%

Sigma-Aldrich

P35405

Diphenyl sulfoxide

Use of phenyl vinyl sulfoxide as an acetylene equivalent in Diels-Alder cycloadditions.
Paquette LA, et al.
Journal of the American Chemical Society, 100(5), 1597-1599 (1978)
X Ji et al.
Acta crystallographica. Section B, Structural science, 45 ( Pt 1), 93-99 (1989-02-01)
Three diastereomers of bicyclo[2.2.1]hept-5-en-2-yl phenyl sulfoxide were prepared by Diels-Alder [4 + 2] cycloadditions between phenyl vinyl sulfoxide and cyclopentadiene. The isomers were separated by column chromatography on silica gel and repeated recrystallizations gave the pure racemates of three of
Masataka Kawakita et al.
The Journal of organic chemistry, 62(23), 8015-8017 (2001-10-24)
Vinyl sulfoxides (PhSOCR(1)=CHR(2): R(1) = H, Me, or Ph; R(2) = H or Me) were treated with (dialkylamino)magnesium reagents, generated in situ from the reaction of EtMgBr with secondary amines (R(3)R(4)NH: R(3) = Et, i-Pr, or Bn; R(4) = Me
Wendy A Loughlin et al.
Organic & biomolecular chemistry, 1(8), 1347-1353 (2003-08-22)
The enolates generated from cyclopentanone, cycloheptanone or cyclooctanone and LDA at -78 degrees C in THF react with (+/-)-phenyl vinyl sulfoxide under controlled conditions of temperature, reaction time, and concentration. Upon oxidation with MCPBA of the product mixtures, the novel

Articles

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service