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392510

Sigma-Aldrich

1-Iodo-3,5-dimethylbenzene

99%

Sinónimos:

5-Iodo-m-xylene

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About This Item

Fórmula lineal:
(CH3)2C6H3I
Número de CAS:
22445-41-6
Peso molecular:
232.06
MDL number:
MFCD00060659
UNSPSC Code:
12352100
PubChem Substance ID:
24864461
NACRES:
NA.22

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.)

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

Categorías relacionadas

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

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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3,5-Dichloroiodobenzene 99%

Sigma-Aldrich

192546

3,5-Dichloroiodobenzene

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 Chemistry, 3(3), 298-304 (2012)
Recyclable and reusable nano-CuFe2O4 catalyzed CO cross-coupling.
Avudoddi V, et al.
European Journal of Organic Chemistry, 3(3), 298-304 (2012)
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