Phenyl vinyl sulphoxide
Basic information
- CAS
20451-53-0- Standard SMILES
C=CS(=O)c1ccccc1- InChIKey
MZMJHXFYLRTLQX-UHFFFAOYSA-N- Molecular formula
- C8H8OS
- Average molar mass
- 152.22 g/mol
- Monoisotopic mass
- 152.02958588
Names & identifiers
- Preferred name
- Phenyl vinyl sulphoxide
- IUPAC
- ethenylsulfinylbenzene
- English name
- Phenyl vinyl sulfoxide
- Molecular formula
- C8H8OS
- Molecular weight
- 152.21
Names & synonyms
Benzene, (ethenylsulfinyl)-Phenyl vinyl sulphoxideEINECS 243-831-6RefChem:861644243-831-6Phenyl vinyl sulfoxide20451-53-0(Vinylsulfinyl)benzeneethenylsulfinylbenzene(ETHENESULFINYL)BENZENEvinylsulfinylbenzeneMFCD00002086
Show more names
NISTC20451530PhenylVinylSulfoxide>(Ethenylsulfinyl)benzenePhenyl ethenyl sulfoxidePhenyl (ethenyl) sulfoxide
Sulfoxide, phenyl vinylCHEMBL16534787500-51-4vinyl phenyl sulfoxide(Ethenylsulfinyl)benzenephenylvinyl sulfoxidevinylsulfinyl-benzeneEthenesulfinyl-benzene
Database identifiers
- CAS
20451-53-0- PubChem CID
- 88544
- DTXSID
DTXSID90942627- ChEMBL
CHEMBL165347- EC Number
- 243-831-6
- Nikkaji
- J208.881I
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 36.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 136
Physicochemical properties
- Boiling point
- 93 · 93-95 °C/0.2 mmHg (lit.)
- Density
- 1.139 g/mL · 1.139 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.585(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
- solubility
- sol most organic solvents
- form
- liquid
- color
- deeply yellow
- BRN
- 2039218 · 2039218
- InChI
- 1S/C8H8OS/c1-2-10(9)8-6-4-3-5-7-8/h2-7H,1H2
- InChIKey
- MZMJHXFYLRTLQX-UHFFFAOYSA-N
- SMILES
- C=CS(=O)c1ccccc1
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- Hazard Codes
- Xi
- Risk Statements
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationBenzene, (ethenylsulfinyl)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- wgk
- 3
- hs_code
- 2930909899
- risk_code
- 41
- hazard_code
- Xi
- safety_code
- 24/25-39-26
- Storage Class
- 10 - Combustible liquids
Chemistry & industry
Applications
UsesPhenyl vinyl sulfoxide is used as acetylene equivalent in Diels-Alder, dipolar cycloaddition, and Michael reactions; can be deprotonated to the unsaturated α-sulfinyl carbanion; undergoes additive Pummerer reactions.
General DescriptionPhenyl 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.
Preparation methods
PreparationPhenyl vinyl sulfoxide can be prepared by reaction of a carbanion with chiral arylsulfinates derived from menthol or glucose, or N-sulfinyloxazolidinones of norephedrine or phenylalanine, or by sequential arylation-vinylation of sulfites derived from lactic acid or aminosulfites derived from ephedrine (99+% ee).
Suppliers
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Related reactions
7 records
Compound notes
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