THIOPHENOL COPPER(I) SALT Property

Melting point:

280 °C (dec.)(lit.)

form 

solid

BRN 

3709171

Safety

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3263 8/PG 2

WGK Germany 

3

F 

1-10-13

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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

P363Wash contaminated clothing before reuse.

THIOPHENOL COPPER(I) SALT Chemical Properties,Usage,Production

Uses

Reagents used as the source of nucleophilic phenyl sulfide for preparation of lithiumalkyl(phenylthio)cuprates and organophosphinecopper(I) phenylthiolatecomplexes

Preparation

One method to preparing Thiophenol Copper(I) salt is to treat Thiophenol with Copper(I) Oxide in ethanol at reflux to give phenylthiocopper as a yellow suspension. Alternatively, lithiation of thiophenol and quenching with Copper(I) Iodide affords a yellow solution,  which is typically reacted in situ with organometallic reagents.

reaction suitability

core: copper
reagent type: catalyst

Purification Methods

The Cu salt can be extracted from a thimble (Soxhlet) with boiling MeOH. It is a green-brown powder which gives a yellow-green solution in pyridine. Wash it with EtOH and dry it in a vacuum. It can be precipitated from a pyridine solution by adding H2O, collecting the precipitate, washing it with EtOH and drying in a vacuum. [Posner et al. Synthesis 662 1974, Krebs et al. Chem Ber 90 425 1957, Beilstein 6 IV 1465.]