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Triphenylsulfonium chloride

HCID 61343
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Basic information

CAS
4270-70-6
Standard SMILES
[Cl-].c1ccc([S+](c2ccccc2)c2ccccc2)cc1
InChIKey
ZFEAYIKULRXTAR-UHFFFAOYSA-M
Molecular formula
C18H15S.Cl
Average molar mass
298.8 g/mol
Monoisotopic mass
298.0582993

Overview

RN given refers to chloride

Names & identifiers

Preferred name
Triphenylsulfonium chloride
IUPAC
triphenylsulfanium chloride
English name
Triphenylsulfonium chloride
Molecular formula
C18H15ClS
Molecular weight
298.83

Names & synonyms

TRIPHENYLSULFONIUM CHLORIDE4270-70-6Triphenylsulfonium ionSulfonium, triphenyl-, chloride93VMP8WB2ZDTXSID5052096RefChem:899973DTXCID0030663Triphenyl sulfideTriphenylsulphonium chlorideTriphenylsulfoniumchloridetriphenylsulfanium chloride
Show more names
LFC1064triphenylsulfurchloridetriphenylchlorothiosaltTriphenylsulfoniumchloridtriphenyl-sulfoniuchlorideSulfonium,triphenyl-,chloride
triphenylsulfanium;chloride10937-76-5MFCD00031716EINECS 224-259-6Triphenyl sulfonium chlorideSCHEMBL60006AKOS005258038SY298159

Database identifiers

CAS
4270-70-6
PubChem CID
61343
DTXSID
DTXSID5052096
UNII
93VMP8WB2Z
EC Number
224-259-6

Properties

Computed structural properties

Topological polar surface area
1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
3
Heavy atoms
20
Formal charge
0
Complexity
202

Physicochemical properties

Melting point
277 °C · 277 °C
storage temp.
2 · under inert gas (nitrogen or Argon) at 2-8°C
form
powder
color
Faint yellow
Water Solubility
Soluble in water.
InChI
InChI=1S/C18H15S.ClH/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h1-15H;1H/q+1;/p-1
InChIKey
ZFEAYIKULRXTAR-UHFFFAOYSA-M
SMILES
[S+](C1=CC=CC=C1)(C1=CC=CC=C1)C1C=CC=CC=1.[Cl-]
CAS DataBase Reference
4270 · 4270-70-6(CAS DataBase Reference)
FDA UNII
93 VMP8WB2Z · 93VMP8WB2Z
EPA Substance Registry System
Triphenylsulfonium chloride (4270-70-6)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a

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 · 4 items

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 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Sulfonium, triphenyl-, chloride

Sulfonium, triphenyl-, chloride: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

wgk
3
hs_code
2930909899
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26
Hazard statements
H315-H319-H335
Precautionary statements
P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Applications · 1 item

UsesTriphenylsulfonium chloride is used as a key intermediate that is widely used in the new electronic chemicals such as semiconductor, LCD and TFT. It is also used as a photoacid generator (PAG) in Catalyst activation through in situ photogeneration of ligands.

Preparation methods · 1 item

PreparationTriphenylsulfonium Chloride Synthesis: Diphenyl sulfoxide, 40 g (0.2 mole), was dissolved in 400 g of dichloroethane, which was stirred under ice cooling. At a temperature below 20° C., 65 g (0.6 mole) of trimethylsilyl chloride was added dropwise to the solution, which was aged for 30 minutes at the temperature. Then, a Grignard reagent which had been prepared from 14.6 g (0.6 mole) of metallic magnesium, 67.5 g (0.6 mole) of chlorobenzene and 168 g of tetrahydrofuran (THF) was added dropwise at a temperature below 20° C. The reaction solution was aged for one hour, after which 50 g of water at a temperature below 20° C. was added to quench the reaction. To this solution, 150 g of water, 10 g of 12N hydrochloric acid, and 200 g of diethyl ether were further added.The water layer was separated and washed with 100 g of diethyl ether, yielding an aqueous solution of triphenylsulfonium chloride. The compound in aqueous solution form was used in the subsequent reaction without further isolation.

Upstream & downstream products

Upstream raw materials

ChlorotrimethylsilanePhenyl sulfoxideChlorobenzeneTetrahydrofuran

Related reactions

57 records
New reaction record
HRID 2913 reaction equation
HRID 2913As reactantuspto-grants-1998_03
HRID 2914 reaction equation
HRID 2914As reactantuspto-grants-1998_03
HRID 58518 reaction equation
HRID 58518As reactantuspto-grants-2016_09
HRID 219506 reaction equation
HRID 219506As productuspto-grants-2012_06
HRID 225405 reaction equation
HRID 225405As reactantuspto-grants-2009_07
HRID 333567 reaction equation
HRID 333567As reactantuspto-grants-2014_11
HRID 388999 reaction equation
HRID 388999As reactantuspto-grants-2013_02
HRID 405012 reaction equation
HRID 405012As reactantuspto-grants-2014_06
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Compound notes

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More actions
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Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26
WGK Germany
3 · 3
HS Code
2930909899 · 2930909899