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03140

Sigma-Aldrich

Copper(I) iodide

purum, ≥99.5%

Synonym(s):

Cuprous iodide

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About This Item

Empirical Formula (Hill Notation):
CuI
CAS Number:
7681-65-4
Molecular Weight:
190.45
EC Number:
231-674-6
MDL number:
MFCD00010978
UNSPSC Code:
12161600
eCl@ss:
38150105
PubChem Substance ID:
57646720
NACRES:
NA.22

vapor pressure

10 mmHg ( 656 °C)

Quality Level

200

grade

purum

Assay

≥99.5%

reaction suitability

core: copper
reagent type: catalyst

mp

605 °C (lit.)

density

5.62 g/mL at 25 °C (lit.)

anion traces

sulfate (SO42-): ≤5000 mg/kg

cation traces

Fe: ≤50 mg/kg

SMILES string

[Cu+].[I-]

InChI

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

InChI key

LSXDOTMGLUJQCM-UHFFFAOYSA-M

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Application

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.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Thyroid

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000375328
0000371425
0000368498
0000361185
0000361185

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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)
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)
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)
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
Min Jiang et al.
Organic letters, 14(6), 1420-1423 (2012-03-08)
A domino synthesis of 5,12-dihydroindolo[2,1-b]quinazoline derivatives via copper-catalyzed Ullmann-type intermolecular C-C and intramolecular C-N couplings is reported. Good yields of various 5,12-dihydroindolo[2,1-b]quinazoline derivatives were obtained. Reaction scopes, limitations, and the reaction mechanism are discussed.
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