| Identification | More | [Name]
Iodobenzene | [CAS]
591-50-4 | [Synonyms]
AKOS BBS-00004395
IODOBENZENE
Benzene iodide
Benzene,iodo-
benzeneiodide
iodinebenzol
iodo-benzen
Phenyl iodide
Phenyliodide
IODOBENZENE, STAB.
Iodobenzene98%
lodobenzene
1-Iodobenzene
3-Iodobenzene
4-Iodobenzene
mono iodobenzene | [EINECS(EC#)]
209-719-6 | [Molecular Formula]
C6H5I | [MDL Number]
MFCD00001029 | [Molecular Weight]
204.01 | [MOL File]
591-50-4.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR YELLOW LIQUID | [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.)
| [Fp ]
74 °C
| [storage temp. ]
Store below +30°C. | [solubility ]
0.34g/l (experimental) | [form ]
Liquid | [color ]
Clear yellow | [Specific Gravity]
1.823 | [Water Solubility ]
insoluble | [Sensitive ]
Light Sensitive | [Merck ]
14,5029 | [BRN ]
1446140 | [Dielectric constant]
4.6（20℃） | [InChIKey]
SNHMUERNLJLMHN-UHFFFAOYSA-N | [CAS DataBase Reference]
591-50-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzene, iodo-(591-50-4) | [EPA Substance Registry System]
591-50-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36:Irritating to the eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
NA 1993 / PGIII | [WGK Germany ]
3
| [RTECS ]
DA3390000
| [F ]
8 | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29036990 | [Hazardous Substances Data]
591-50-4(Hazardous Substances Data) |
| Questions And Answer | Back Directory | [Introduction]
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. | [Chemical Properties]
Colorless 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℃） | [Usage]
A general reagent for organic synthesis and used as a standard liquid refractive index | [Preparation]
Iodobenzene 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%. |
| Hazard Information | Back Directory | [Uses]
suzuki 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 Methods]
Wash 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.] |
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