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I7632

Sigma-Aldrich

Iodobenzene

98%

Synonym(s):

1-Iodobenzene, 4-Iodobenzene, Benzene iodide, Phenyl iodide

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About This Item

Empirical Formula (Hill Notation):
C6H5I
CAS Number:
591-50-4
Molecular Weight:
204.01
Beilstein:
1446140
EC Number:
209-719-6
MDL number:
MFCD00001029
UNSPSC Code:
12352100
PubChem Substance ID:
24896121
NACRES:
NA.22

Assay

98%

refractive index

n20/D 1.62 (lit.)

bp

188 °C (lit.)

mp

−29 °C (lit.)

density

1.823 g/mL at 25 °C (lit.)

SMILES string

Ic1ccccc1

InChI

1S/C6H5I/c7-6-4-2-1-3-5-6/h1-5H

InChI key

SNHMUERNLJLMHN-UHFFFAOYSA-N

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General description

Iodobenzene, also known as phenyl iodide, is commonly used as an arylating agent in various cross-coupling reactions.

Application

Iodobenzene is used in various C-C coupling reactions. It can be used in the preparation of iodobenzene dichloride, which is employed as an oxidant to oxidize alcohols to carbonyl compounds and as a chlorinating agent.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

170.6 °F - closed cup

Flash Point(C)

77 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Heck reactions of iodobenzene and methyl acrylate with conventional supported palladium catalysts in the presence of organic and/and inorganic bases without ligands.
Zhao, Fengyu et al.
Chemistry?A European Journal , 6(5), 843-848 (2000)
Size effects of PVP- Pd nanoparticles on the catalytic Suzuki reactions in aqueous solution.
Li, Yin et al.
Langmuir, 18(12), 4921-4925 (2002)
Iodobenzene dichloride as a stoichiometric oxidant for the conversion of alcohols into carbonyl compounds; two facile methods for its preparation.
Zhao, Xue-Fei and Zhang, Chi
Synthesis, 2007(04), 551-557 (2007)
Minfeng Zeng et al.
The Journal of organic chemistry, 75(8), 2556-2563 (2010-03-23)
Palladium-catalyzed reductive homocoupling of aromatic halides can be performed in alcohol solutions without any auxiliary reducing reagents. Pd(dppf)Cl(2) [dppf = 1,1'-bis(diphenylphosphino)ferrocene] has been shown as the most effective catalyst among the palladium catalysts screened for the model reductive homocoupling of
Ring-Opening 1, 3-Dichlorination of Donor-Acceptor Cyclopropanes by Iodobenzene Dichloride.
Garve, Lennart KB et al.
Organic Letters, 16(21), 5804-5807 (2014)
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