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252786

Sigma-Aldrich

2-Iodoanisole

98%

Synonym(s):

2-Iodophenyl methyl ether, 2-Methoxyiodobenzene

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About This Item

Linear Formula:
IC6H4OCH3
CAS Number:
529-28-2
Molecular Weight:
234.03
Beilstein:
1860243
EC Number:
208-456-4
MDL number:
MFCD00001039
UNSPSC Code:
12352100
PubChem Substance ID:
24855237
NACRES:
NA.22

Quality Level

200

Assay

98%

form

liquid

refractive index

n20/D 1.622 (lit.)

bp

125-126 °C/19 mmHg (lit.)

solubility

alcohol: miscible(lit.)
chloroform: miscible(lit.)
diethyl ether: miscible(lit.)
water: insoluble(lit.)

density

1.799 g/mL at 25 °C (lit.)

SMILES string

COc1ccccc1I

InChI

1S/C7H7IO/c1-9-7-5-3-2-4-6(7)8/h2-5H,1H3

InChI key

DVQWNQBEUKXONL-UHFFFAOYSA-N

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General description

2-Iodoanisole participates in palladium catalyzed enantioselective Heck arylation of 2,3-dihydrofuran in the presence of chiral ionic liquids containing L-prolinate and L-lactate anions and non-chiral quaternary ammonium cations.

Application

2-Iodoanisole has been used in palladium/copper-catalyzed synthesis of o-(1-alkynyl)anisoles.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF4468
BCCB5161
BCBZ9539
BCBV3958
BCBQ8961V

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Adam Morel et al.
Dalton transactions (Cambridge, England : 2003), 42(4), 1215-1222 (2012-11-09)
Chiral ionic liquids (CILs) containing L-prolinate and L-lactate anions and non-chiral quaternary ammonium cations were employed in the palladium catalyzed enantioselective Heck arylation of 2,3-dihydrofuran with aryl iodides (iodobenzene, 4-iodotoluene, 2-iodoanisole, 4-iodoanisole, 4-iodoacetophenone). In all the reactions 2-aryl-2,3-dihydrofuran (3) was
Dawei Yue et al.
The Journal of organic chemistry, 70(25), 10292-10296 (2005-12-06)
[reaction: see text] 2,3-Disubstituted benzo[b]furans are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of various o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization with I2, PhSeCl, or p-O2NC6H4SCl. Aryl- and vinylic-substituted alkynes undergo electrophilic cyclization in
Naoyuki Yasaka et al.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry, 34(10), 1183-1188 (2018-10-12)
Aryl halides are a very important category of compounds that include many vital drugs and key industrial additives, such as clofibrate and bromobenzene, respectively. Due to their importance, our research group previously developed a novel fluorescence labeling approach for their

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