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Iodobenzene

CAS No.
591-50-4
Chemical Name:
Iodobenzene
Synonyms
iodo-benzen;Phenyl iodide;iodinebenzol;Benzene,iodo-;benzeneiodide;1-Iodobenzene;4-Iodobenzene;mono iodobenzene;IODOBENZENE, STAB.;Iodbenzol
CBNumber:
CB0700740
Molecular Formula:
C6H5I
Molecular Weight:
204.01
MDL Number:
MFCD00001029
MOL File:
591-50-4.mol
MSDS File:
SDS
Modify Date:2022-12-21 16:56:50

Iodobenzene 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.)
Flash point 74 °C
storage temp. Store below +30°C.
solubility 0.34g/l (experimental)
form Liquid
Specific Gravity 1.823
color Clear yellow
Water Solubility insoluble
Sensitive Light Sensitive
Merck 14,5029
BRN 1446140
InChIKey SNHMUERNLJLMHN-UHFFFAOYSA-N
CAS DataBase Reference 591-50-4(CAS DataBase Reference)
FDA UNII 9HK5L7YBBR
NIST Chemistry Reference Benzene, iodo-(591-50-4)
EPA Substance Registry System Benzene, iodo- (591-50-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P501
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
NFPA 704
1
2 0

Iodobenzene price More Price(30)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich I7632 Iodobenzene 98% 591-50-4 5G $35.3 2023-01-07 Buy
Sigma-Aldrich I7632 Iodobenzene 98% 591-50-4 100g $76.7 2023-01-07 Buy
Sigma-Aldrich I7632 Iodobenzene 98% 591-50-4 500g $244 2023-01-07 Buy
TCI Chemical I0050 Iodobenzene 591-50-4 25G $21 2023-01-07 Buy
TCI Chemical I0050 Iodobenzene 591-50-4 100G $55 2023-01-07 Buy
Product number Packaging Price Buy
I7632 5G $35.3 Buy
I7632 100g $76.7 Buy
I7632 500g $244 Buy
I0050 25G $21 Buy
I0050 100G $55 Buy

Iodobenzene Chemical Properties,Uses,Production

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%.

Chemical Properties

CLEAR YELLOW LIQUID

Uses

suzuki reaction

Uses

Iodobenzene 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.

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.]

98-80-6
591-50-4
Synthesis of Iodobenzene from Phenylboronic acid
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View Lastest Price from Iodobenzene manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Iodobenzene pictures 2023-02-06 Iodobenzene
591-50-4
US $12.00 / kg 1kg 99% 100mt Jinan Finer Chemical Co., Ltd
Iodobenzene pictures 2023-01-31 Iodobenzene
591-50-4
US $100.00 / kg 1kg 99 300tons Hebei Mojin Biotechnology Co., Ltd
 Iodobenzene pictures 2023-01-30 Iodobenzene
591-50-4
US $5.60 / KG 1KG 99% 5000kg Hebei Crovell Biotech Co Ltd
  • Iodobenzene pictures
  • Iodobenzene
    591-50-4
  • US $12.00 / kg
  • 99%
  • Jinan Finer Chemical Co., Ltd
  • Iodobenzene pictures
  • Iodobenzene
    591-50-4
  • US $100.00 / kg
  • 99
  • Hebei Mojin Biotechnology Co., Ltd
  •  Iodobenzene pictures
  • Iodobenzene
    591-50-4
  • US $5.60 / KG
  • 99%
  • Hebei Crovell Biotech Co Ltd
Benzene iodide IODOBENZENE AKOS BBS-00004395 3-Iodobenzene Iodobenzene, 98% 100ML Phenyliodide Iodobenzene98% Iodobenzene, 97.5% Iodbenzol Iodobenzene 97+% Vortioxetine Impurity 51 Iodobenzene> IODOBENZENE FOR SYNTHESIS 100 ML IODOBENZENE FOR SYNTHESIS 250 ML Iodobenzene ISO 9001:2015 REACH Iodobenzene iodo-benzen IODOBENZENE For Synthesis iodo-benzen Phenyl iodide Benzene,iodo- benzeneiodide iodinebenzol 1-Iodobenzene 4-Iodobenzene mono iodobenzene IODOBENZENE, STAB. lodobenzene 591-50-4 591-50-1 591504 IC6H5 C6H5l HALOGEN Building Blocks Aryl Halogenated Hydrocarbons Organic Building Blocks C6 alkyl Iodine Aryl C6 Halogenated Hydrocarbons API intermediates Iodine Compounds Pharmaceutical Intermediate Pharmaceutical Intermediates Aromatic Halides (substituted) Organics bc0001