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531464

Sigma-Aldrich

2-Iodophenylacetonitrile

97%

Synonym(s):

2-Iodobenzyl cyanide

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About This Item

Linear Formula:
IC6H4CH2CN
CAS Number:
40400-15-5
Molecular Weight:
243.04
MDL number:
MFCD00040888
UNSPSC Code:
12352100
PubChem Substance ID:
24877818

Assay

97%

refractive index

n20/D 1.618 (lit.)

bp

113-120 °C/0.5 mmHg (lit.)

density

1.75 g/mL at 25 °C (lit.)

functional group

iodo
nitrile

SMILES string

Ic1ccccc1CC#N

InChI

1S/C8H6IN/c9-8-4-2-1-3-7(8)5-6-10/h1-4H,5H2

InChI key

FPSGTRJUQLYLHE-UHFFFAOYSA-N

General description

2-Iodophenylacetonitrile is a 2-aryl substituted nitrile. It reacts with lactams to form ring-fused isoquinolinones via palladium-catalyzed carboxamidation in tandem with aldol condensation.[1]

Application

2-Iodophenylacetonitrile may be used in the preparation of:
  • 2?-aminobiphen-2-ylacetonitrile[2]
  • ethyl (2-iodophenyl)iminoacetate hydrochloride[3]
  • 3,4-disubstituted 2-naphthalenamines[4]

It may also be used in the preparation of the following nitriles:[5]
  • 2-(2-iodophenyl)-2-methylpropanenitrile
  • 1-(2-iodophenyl)cyclopentanecarbonitrile
  • 5-bromo-2-(2-iodophenyl)pentanenitrile
  • 2-(2-iodophenyl)-2-propylpentanenitrile
  • 1-(2-iodophenyl)cyclohexanecarbonitrile
  • 1-(2-Iodophenyl)cyclopropanecarbonitrile

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BGBB5403V
BGBB5403
09709BH
06107CE
02515DD

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Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2'-disubstituted biphenyls.
Baudoin O, et al.
The Journal of Organic Chemistry, 65(26), 9268-9271 (2000)
Hirokazu Tsukamoto et al.
The Journal of organic chemistry, 81(5), 1733-1745 (2015-11-26)
1,2-Bis(diphenylphosphino)ethane (dppe)-ligated palladium(II) complexes catalyze the annulation of internal alkynes with 2-(cyanomethyl)phenylboronates to provide 3,4-disubstituted-2-naphthalenamines in good yields. The annulation reaction proceeds under mild and neutral conditions and requires methanol as an essential solvent. In addition to symmetrical alkynes, unsymmetrical
David Crich et al.
The Journal of organic chemistry, 71(9), 3452-3463 (2006-04-22)
The [1-cyano-2-(2-iodophenyl)]ethylidene group is introduced as an acetal-protecting group for carbohydrate thioglycoside donors. The group is easily introduced under mild conditions, over short reaction times, and in the presence of a wide variety of other protecting groups by the reaction
Studies in Acyl C? H Activation via Aryl and Alkyl to Acyl ?Through Space? Migration of Palladium.
Kesharwani T, et al.
Organic Letters, 11(12), 2591-2593 (2009)
Palladium-catalyzed carboxamidation reaction and aldol condensation reaction cascade: A facile approach to ring-fused isoquinolinones.
Chouhan G and Alper H.
Organic Letters, 10(21), 4987-4990 (2008)

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