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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.
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Iodobenzene manufacturers

  • Iodobenzene
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  • 2022-03-17
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  • CAS:591-50-4
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  • Iodobenzene
  • $10.00 / 1KG
  • 2021-10-22
  • CAS:591-50-4
  • Min. Order: 1KG
  • Purity: 99%
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Iodobenzene Basic information
Introduction Chemical Properties Usage Preparation
Product Name:Iodobenzene
Synonyms:iodo-benzen;Phenyl iodide;Benzene iodide;Benzene,iodo-;benzeneiodide;iodinebenzol;Iodobenzene, 97.5%;IODOBENZENE
CAS:591-50-4
MF:C6H5I
MW:204.01
EINECS:209-719-6
Product Categories:alkyl Iodine;Aryl;API intermediates;Iodine Compounds;C6;Halogenated Hydrocarbons;Aromatic Halides (substituted);Organics;Pharmaceutical Intermediate;Pharmaceutical Intermediates
Mol File:591-50-4.mol
Iodobenzene Structure
Iodobenzene Chemical Properties
Melting point -29 °C (lit.)
Boiling point 188 °C (lit.)
density 1.823 g/mL at 25 °C (lit.)
refractive index n20/D 1.62(lit.)
Fp 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
Hazardous Substances Data591-50-4(Hazardous Substances Data)
MSDS Information
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Iodobenzene English
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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
UsesIodobenzene is used to prepare biphenyl and stilbene. It reacts with magnesium to form the Grignard reagent, a phenylmagnesium iodide used in organic synthesis. It finds application as a solid chlorine source by reacting with chlorine to form a complex, iodobenzene dichloride. It serves as a substrate in Sonogashira reaction which is used to form a carbon-carbon bond between a terminal alkyne and an aryl halide.
Usessuzuki reaction
Synthesis Reference(s)Tetrahedron Letters, 33, p. 3167, 1992 DOI: 10.1016/S0040-4039(00)79842-X
The Journal of Organic Chemistry, 53, p. 3548, 1988 DOI: 10.1021/jo00250a024
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.]
Tag:Iodobenzene(591-50-4) Related Product Information
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