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Iodobenzene

Iodobenzene is one Iodine substitution of benzene and its molecular formula is C6H5I. It Is a colorless liquid with special odor, insoluble in water, soluble in trichloromethane, ether and ethanol. It is Photosensitive and gradually turns yellow in case of light. Because the bond energy of C-I is lower than that of C-Cl and C-Br, its reactivity is much stronger. It can react with magnesium to generate grignard reagent Phenylmagnesium Iodide (PhMgI), which can be used as equivalent of phenyl anion in organic synthesis. Iodobenzene can be used as the raw material in Sonogashira coupling reaction, Heck reaction and Other metals catalyzed coupling reaction.

Basic information Introduction Chemical Properties Usage Preparation Safety Related Supplier
Iodobenzene Basic information
Iodobenzene Chemical Properties
  • Melting point:−29 °C(lit.)
  • Boiling point:188 °C(lit.)
  • Density 1.830 g/mL at 20 °C
  • refractive index n20/D 1.62(lit.)
  • Flash point:74 °C
  • storage temp. Store below +30°C.
  • solubility 0.34g/l (experimental)
  • form Liquid
  • color Clear yellow
  • Specific Gravity1.823
  • Water Solubility insoluble
  • Sensitive Light Sensitive
  • Merck 14,5029
  • BRN 1446140
  • InChIKeySNHMUERNLJLMHN-UHFFFAOYSA-N
  • CAS DataBase Reference591-50-4(CAS DataBase Reference)
  • NIST Chemistry ReferenceBenzene, iodo-(591-50-4)
  • EPA Substance Registry SystemBenzene, iodo- (591-50-4)
Safety Information
  • Hazard Codes Xn,Xi
  • Risk Statements 22-36-20/22
  • Safety Statements 26-36-23
  • RIDADR NA 1993 / PGIII
  • WGK Germany 3
  • RTECS DA3390000
  • 8
  • Hazard Note Irritant
  • TSCA Yes
  • HS Code 29036990
MSDS
Iodobenzene Usage And Synthesis
  • IntroductionIodobenzene is one Iodine substitution of benzene and its molecular formula is C6H5I. It Is a colorless liquid with special odor, insoluble in water, soluble in trichloromethane, ether and ethanol. It is Photosensitive and gradually turns yellow in case of light. Because the bond energy of C-I is lower than that of C-Cl and C-Br, its reactivity is much stronger. It can react with magnesium to generate grignard reagent Phenylmagnesium Iodide (PhMgI), which can be used as equivalent of phenyl anion in organic synthesis. Iodobenzene can be used as the raw material in Sonogashira coupling reaction, Heck reaction and Other metals catalyzed coupling reaction.
  • Chemical PropertiesColorless liquid, melting point-31.27℃, boiling point 188.3℃, 63-64℃(1.07kPa), Flash point 74 ℃,density 1.8308(20/4℃), refractive index1.6200(18.5℃)
  • UsageA general reagent for organic synthesis and used as a standard liquid refractive index
  • PreparationIodobenzene is obtained through the diazotization and replacement reaction of Aniline.
    Hydrochloric acid( 30%) and aniline were added to Water, stirred and cooled to 2 ℃. Then,  sodium nitrite solution was added dropwise to the above solution and the temperature was controlled to be no more than 12℃. When the last part of sodium nitrite solution was added, potassium iodide starch paper was used to determine the blue reaction endpoint.
    Then, diazotization liquid was obtained.  Potassium iodide solution was added to the diazotization solution in several batches until no nitrogen was released. After cooling, the upper aqueous solution was separated from the above system. Sodium hydroxide solution (10%) was added until the pH value was 14. A distillation process was carried out and aqueous layer was separated from the distillate. The atmospheric fractionation process was arried out after drying and the fraction at184-188 ℃ was collected, which is iodobenzene with a yield of 77%.
  • Chemical PropertiesCLEAR YELLOW LIQUID
  • Usessuzuki reaction
  • Synthesis Reference(s)Chemistry Letters, 11, p. 1481, 1982
    The Journal of Organic Chemistry, 53, p. 3548, 1988
    Tetrahedron Letters, 33, p. 3167, 1992 DOI: 10.1016/S0040-4039(00)79842-X
  • Purification MethodsWash it with dilute aqueous Na2S2O3, then water. Dry it with CaCl2 or CaSO4, decolourise with charcoal and distil it under reduced pressure then store it with mercury or silver powder to stabilise it. [Beilstein 5 IV 688.]
Iodobenzene Preparation Products And Raw materials
Iodobenzene(591-50-4)Related Product Information
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