392510
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:
Molecular Weight:
232.06
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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).[1] It undergoes reaction with phenol in the presence of CuFe2O4 nano powder as a recyclable catalyst to afford 1,3-dimethyl-5-phenoxybenzene.[2]
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.[3]
It may be used in the following studies:
It may be used in the following studies:
- α-Arylation of ketones.[4]
- Copper-catalyzed N-arylation of imidazoles.[5]
- Cyanation of 5-iodo-m-xylene to form 3,5-dimethylbenzonitrile.[6]
- Synthesis of 1,3-Dimethyl-5-phenoxybenzene by nano-CuFe2O4 catalyzed C-O cross-coupling with phenol.[7]
- CuBr-catalyzed amination of 1-iodo-3,5-dimethylbenzene to form N-Allyl-3,5-dimethylbenzenamine.[8]
- Copper-catalyzed C-S bond-formation between 5-iodo-m-xylene and thiophenol.[9]
- As a starting material in the synthesis of biphenyl-3,3′,5,5′-tetracarboxylic acid.[10]
- Radical bromination of 5-iodo-m-xylene by N-bromosuccinimide to form 1,3-bis(bromomethyl)-5-iodobenzene.[11]
Signal Word
Warning
Hazard Statements
Precautionary Statements
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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