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392510

Sigma-Aldrich

1-Iodo-3,5-dimethylbenzene

99%

Synonym(s):

5-Iodo-m-xylene

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About This Item

Linear Formula:
(CH3)2C6H3I
CAS Number:
22445-41-6
Molecular Weight:
232.06
MDL number:
MFCD00060659
UNSPSC Code:
12352100
PubChem Substance ID:
24864461
NACRES:
NA.22

Quality Level

100

Assay

99%

form

liquid

refractive index

n20/D 1.594 (lit.)

bp

92-94 °C/3 mmHg (lit.)

density

1.608 g/mL at 25 °C (lit.)

functional group

iodo

SMILES string

Cc1cc(C)cc(I)c1

InChI

1S/C8H9I/c1-6-3-7(2)5-8(9)4-6/h3-5H,1-2H3

InChI key

ZLMKEENUYIUKKC-UHFFFAOYSA-N

Related Categories

General description

1-Iodo-3,5-dimethylbenzene (5-Iodo-m-xylene) is an aryl halide. It can be obtained from 5-bromo-m-xylene, via copper-catalyzed halogen exchange reaction, in the presence of NaI or KI in n-BuOH or DMF (solvents). It undergoes reaction with phenol in the presence of CuFe2O4 nano powder as a recyclable catalyst to afford 1,3-dimethyl-5-phenoxybenzene.

Application

1-Iodo-3,5-dimethylbenzene (5-iodo-m-xylene) is suitable for use in the synthesis of N-(3,5-xylyl)-N-ethylaniline, an arylamine.
It may be used in the following studies:
  • α-Arylation of ketones.
  • Copper-catalyzed N-arylation of imidazoles.
  • Cyanation of 5-iodo-m-xylene to form 3,5-dimethylbenzonitrile.
  • Synthesis of 1,3-Dimethyl-5-phenoxybenzene by nano-CuFe2O4 catalyzed C-O cross-coupling with phenol.
  • CuBr-catalyzed amination of 1-iodo-3,5-dimethylbenzene to form N-Allyl-3,5-dimethylbenzenamine.
  • Copper-catalyzed C-S bond-formation between 5-iodo-m-xylene and thiophenol.
  • As a starting material in the synthesis of biphenyl-3,3′,5,5′-tetracarboxylic acid.
  • Radical bromination of 5-iodo-m-xylene by N-bromosuccinimide to form 1,3-bis(bromomethyl)-5-iodobenzene.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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)

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
MKCQ3826
MKCL0424
MKCG9312
MKCC6340
MKBW2914V

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Sigma-Aldrich

192546

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2-Bromo-1,3-dimethylbenzene 98%

Sigma-Aldrich

115851

2-Bromo-1,3-dimethylbenzene

Biphenyl-3, 3', 5, 5'-tetracarboxylic acid.
Coles SJ, et al.
Acta Crystallographica Section E, Structure Reports Online, 58(6), 626-628 (2002)
On the synthesis of heterocyclic dendrons.
Diez-Barra E, et al.
ARKIVOC (Gainesville, FL, United States), 2002(5), 17-25 (2002)
M H Ali et al.
The Journal of organic chemistry, 66(8), 2560-2565 (2001-04-17)
Aryl iodides are coupled with amines to give the corresponding arylamines in high yield in the presence of palladium, a suitable ligand, and NaOt-Bu. Functionalized aryl iodides give good yields of the corresponding arylamines when Cs(2)CO(3) is substituted as the
Recyclable and reusable nano-CuFe2O4 catalyzed CO cross-coupling.
Avudoddi V, et al.
European Journal of Organic Chemistry, 3(3), 298-304 (2012)
An efficient copper-catalyzed coupling of aryl halides with imidazoles.
Kiyomori A, et al.
Tetrahedron Letters, 40(14), 2657-2660 (1999)
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