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2-Iodo-1,3-dimethylbenzene

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2-Iodo-1,3-dimethylbenzene Basic information

Product Name:
2-Iodo-1,3-dimethylbenzene
Synonyms:
  • 1,2-Dimethyl-2-jodbenzol
  • 1-Iodo-2,6-dimethylbenzene
  • 2,6-Dimethyl-1-iodobenzene
  • 2-iodo-1,3-dimethyl-benzen
  • 2-Jod-m-xylol
  • Benzene,2-iodo-1,3-dimethyl-
  • m-Xylene, 2-iodo-
  • I**2-IODO-M-XYLENE
CAS:
608-28-6
MF:
C8H9I
MW:
232.06
EINECS:
612-042-2
Product Categories:
  • Halogen toluene
  • Iodine Compounds
Mol File:
608-28-6.mol
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2-Iodo-1,3-dimethylbenzene Chemical Properties

Melting point:
11.2°C
Boiling point:
223-224 °C (lit.)
Density 
1.608 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.6030(lit.)
Flash point:
216 °F
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Oil
color 
Clear Pale Yellow
Water Solubility 
insoluble
Sensitive 
Light Sensitive
BRN 
1857414
InChIKey
QTUGGVBKWIYQSS-UHFFFAOYSA-N
CAS DataBase Reference
608-28-6(CAS DataBase Reference)
NIST Chemistry Reference
Benzene, 2-iodo-1,3-dimethyl-(608-28-6)
EPA Substance Registry System
Benzene, 2-iodo-1,3-dimethyl- (608-28-6)
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Safety Information

Hazard Codes 
Xi,C
Risk Statements 
37/38-41-36/37/38
Safety Statements 
26-36-37/39
WGK Germany 
3
TSCA 
Yes
HazardClass 
IRRITANT
HS Code 
29039990

MSDS

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2-Iodo-1,3-dimethylbenzene Usage And Synthesis

Chemical Properties

clear green-brown to brown liquid

Uses

2-Iodo-m-xylene is used in the preparation of p-(arylethynyl)arylpropanoic acid derivatives as free fatty acid receptor 1 agonists with low lipophilicity and high oral bioavailability.

Synthesis

100379-00-8

608-28-6

General procedure for the synthesis of 2-iodo-1,3-dimethylbenzene using 2,6-dimethylphenylboronic acid as starting material: arylboronic acid (0.5 mmol) and K2CO3 (1 mmol, 138.0 mg) were added to a 20 mL Schlenk tube fitted with a non-magnetic stir bar. The reaction tube was evacuated and filled with nitrogen and this operation was repeated twice. Acetonitrile (2 mL) and iodine (0.75 mmol, 191 mg) were added to the reaction tube at room temperature. The reaction tube was sealed and placed in an oil bath preheated to 80 °C for 8-12 h under nitrogen protection. Upon completion of the reaction, the reaction solution was cooled to room temperature. Water (10 mL) was added for dilution. For the products 2s and 2t, the pH needed to be adjusted to 2 by adding 1 M HCl to the aqueous phase before extraction. the aqueous phase was extracted with ethyl acetate (3 x 5 mL). The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated by rotary evaporation. Finally, the residue was purified by silica gel column chromatography to give the target products 2a-v.

References

[1] Synlett, 2014, vol. 25, # 7, p. 995 - 1000

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