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A12788 Iodobenzene, 98%

CAS Number
591-50-4
Synonyms

Stock No. Size Price ($) Quantity Availability
A12788-18 50g 38.90
A12788-22 100g 63.00
A12788-0B 1000g 355.00
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Iodobenzene, 98%

MDL
MFCD00001029
EINECS
209-719-6

Chemical Properties

Formula
C6H5I
Formula Weight
204.01
Melting point
-31°
Boiling Point
188-189°
Flash Point
74°(165°F)
Density
1.826
Refractive Index
1.6200
Storage & Sensitivity
Light Sensitive. Ambient temperatures.
Solubility
Miscible with ethanol, chloroform and ether. Slightly miscible with dimethyl sulfoxide. Immiscible with water.

Applications

Iodobenzene is used to prepare biphenyl and stilbene. It reacts with magnesium to form the Grignard reagent, a phenylmagnesium iodide used in organic synthesis. It finds application as a solid chlorine source by reacting with chlorine to form a complex, iodobenzene dichloride. It serves as a substrate in Sonogashira reaction which is used to form a carbon-carbon bond between a terminal alkyne and an aryl halide.

Notes

Light sensitive. Incompatible with magnesium and strong oxidizing agents.

Literature References

Active methylene compounds undergo CuI-catalyzed phenylation in DMSO: J. Org. Chem., 58, 7606 (1993).

In the presence of Pd catalysts, couples with a wide range of acrylic species or allylic alcohols in the Heck reaction. For example (2-methyl-2-propen-1-ol), see: Org. Synth. Coll., 7, 361 (1990).

For an extensive collection of the synthetically-useful reactions of iodoaromatics, see: Synthesis, 923 (1988).

Alla, S. K.; Kumar, R. K.; Sadhu, P.; Punniyamurthy, T. Iodobenzene Catalyzed C-H Amination of N-Substituted Amidines Using m-Chloroperbenzoic Acid. Org. Lett. 2013, 15 (6), 1334-1337.

Kurbangalieva, A.; Carmichael, D.; Hii, K. K.; Jutand, A.; Brown, J. M. Oxidative Addition to Palladium (0) Diphosphine Complexes: Observations of Mechanistic Complexity with Iodobenzene as Reactant. Chem. Eur. J. 2014, 20 (4), 1116-1125.

GHS Hazard and Precautionary Statements

Hazard Statements: H227-H302-H332

Combustible liquid. Harmful if swallowed. Harmful if inhaled.

Precautionary Statements: P210-P261-P264b-P270-P271-P280-P301+P312-P304+P340-P312-P330-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Rinse mouth. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,5029
Beilstein
1446140
Harmonized Tariff Code
2903.99
TSCA
Yes
RTECS
DA3390000

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