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Merck

03140

Sigma-Aldrich

Kupfer(I)-Iodid

purum, ≥99.5%

Synonym(e):

Cuprous iodide

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About This Item

Empirische Formel (Hill-System):
CuI
CAS-Nummer:
Molekulargewicht:
190.45
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12161600
eCl@ss:
38150105
PubChem Substanz-ID:
NACRES:
NA.22

Dampfdruck

10 mmHg ( 656 °C)

Qualitätsniveau

Qualität

purum

Assay

≥99.5%

Eignung der Reaktion

core: copper
reagent type: catalyst

mp (Schmelzpunkt)

605 °C (lit.)

Dichte

5.62 g/mL at 25 °C (lit.)

Anionenspuren

sulfate (SO42-): ≤5000 mg/kg

Kationenspuren

Fe: ≤50 mg/kg

SMILES String

[Cu+].[I-]

InChI

1S/Cu.HI/h;1H/q+1;/p-1

InChIKey

LSXDOTMGLUJQCM-UHFFFAOYSA-M

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Anwendung

Copper(I) iodide, in combination with cesium fluoride, can be used to promote Stille coupling reaction. It can also mediate the reaction between arenethiolate ions and different
nonactivated aryl iodides in hexamethylphosphoric triamide to form aryl sulfides.
Copper(I) iodide can be used to catalyze:
  • Thioetherification of aryl halides using thiourea and alkyl bromides in wet polyethylene glycol and in the presence of potassium carbonate as a base.
  • Reaction between acetylenes and metal halides in diethylamine to form transition metal alkynyl complexes.
  • Reaction between terminal alkynes with phenylchalcogenyl halides to form alkynyl selenides, sulfides and tellurides.

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1A - STOT RE 1 Oral

Zielorgane

Thyroid

Lagerklassenschlüssel

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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Significant enhancement of the Stille reaction with a new combination of reagents?copper (I) iodide with cesium fluoride.
Mee SP, et al.
Chemistry?A European Journal , 11(11), 3294-3308 (2005)
One?Pot Thioetherification of Aryl Halides Using Thiourea and Alkyl Bromides Catalyzed by Copper (I) Iodide Free from Foul?Smelling Thiols in Wet Polyethylene Glycol (PEG 200).
Firouzabadi H, et al.
Advanced Synthesis & Catalysis, 352(1), 119-124 (2010)
Facile substitution reaction between nonactivated aryl iodides and arenethiolates in the presence of copper (I) iodide.
Suzuki H, et al.
Chemistry Letters (Jpn), 9(11), 1363-1364 (1980)
Roberta Berrino et al.
The Journal of organic chemistry, 77(5), 2537-2542 (2012-01-31)
Free NH 3,3-diarylacrylamides are cyclized to substituted 2-quinolones in the presence of CuI, PPh(3), and KO-t-Bu in o-xylene at 100 °C. The reaction proceeds through a C-H functionalization/C-N bond formation process. With unsymmetrical 3,3-diarylacrylamides, high selectivity is observed using substrates
Novel preparation of σ-alkynyl complexes of transition metals by copper (I) iodide-catalysed dehydrohalogenation.
Sonogashira K, et al.
Journal of the Chemical Society. Chemical Communications, 9, 291-292 (1977)

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