Iodobenzene dichloride

Structural formula
General
Surname	Iodobenzene dichloride
Molecular formula	C 6 H 5 Cl 2 I.
Brief description	yellow solid
External identifiers / databases
PubChem	13166207
ChemSpider	254526
Wikidata	Q5961335
properties
Molar mass	274.1 g mol −1
density	2.2 g cm −3
Melting point	115-120 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Iodobenzene dichloride (PhICl ₂ ) is a chemical compound made from iodobenzene and chlorine , which is mainly used as an oxidizing and chlorinating agent .

structure

According to the crystal structure analysis, it is a T-shaped structure with a central iodine atom . Corresponding predictions with the VSEPR model were thus confirmed.

Molecular geometry

presentation

Iodobenzene dichloride is an unstable compound. It can be obtained through a precipitation reaction in which chlorine gas is passed through a solution of iodobenzene in chloroform , whereby iodobenzene dichloride precipitates. This synthesis route is used both in the laboratory and in production on an industrial scale.

{\ displaystyle {\ ce {Ph-I + Cl2 -> PhICl2}}}

Alternatively, there is also the option of producing the required chlorine in situ from sodium hypochlorite and hydrochloric acid .

Reactions

Hydrolysis in a basic solution produces iodosobenzene (PhIO) and oxidation, for example with sodium hypochlorite , produces iodoxybenzene .

In organic synthesis, iodobenzene dichloride can be used to selectively chlorinate alkenes and alkynes .

Individual evidence

↑ ^a ^b ^c ^d David W. Knight, Glen A. Russell: Phenyliodine (III) Dichloride . In: Encyclopedia of Reagents for Organic Synthesis . American Cancer Society, 2001, ISBN 978-0-470-84289-8 , doi : 10.1002 / 047084289X.rp071 .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
^ EM Archer, TG van Schalkwyk: The crystal structure of benzene iododichloride . In: Acta Crystallographica . tape 6 , no. 1 , January 10, 1953, p. 88-92 , doi : 10.1107 / S0365110X53000193 ( iucr.org ).
^ JV Carey, PA Chaloner, PB Hitchcock, T. Neugebauer, KR Seddon: Synthesis and Decomposition of Dichloroiodoarenes. An Improved Low Temperature X-Ray Structure of Dichloroiodobenzene and the Structure of 1-Chloro-2,3,5,6-tetrakis (chloromethyl) -4-methylbenzene. In: ChemInform . tape 27 , no. 52 , 1996, doi : 10.1002 / chin.199652032 .
↑ ^a ^b H. J. Lucas and ER Kennedy: Iodobenzene dichloride In: Organic Syntheses . 22, 1942, p. 69, doi : 10.15227 / orgsyn.022.0069 ; Coll. Vol. 3, 1955, p. 482 ( PDF ).
↑ Atsuhiko Zanka, Hiroki Takeuchi, Ariyoshi Kubota: Large-Scale Preparation of Iodobenzene Dichloride and Efficient Monochlorination of 4-Aminoacetophenone . In: Organic Process Research & Development . tape 2 , no. 4 , July 1, 1998, pp. 270-273 , doi : 10.1021 / op980024e .
↑ Xue-Fei Zhao, Chi Zhang: Iodobenzene Dichloride as a Stoichiometric Oxidant for the Conversion of Alcohols into Carbonyl Compounds; Two Facile Methods for Its Preparation . In: Synthesis . tape 2007 , no. February 04 , 2007, p. 551-557 , doi : 10.1055 / s-2007-965889 .

^ MW Formo and John R. Johnson: Iodoxybenzene: B. Hypochlorite oxidation of iodobenzene dichloride In: Organic Syntheses . 22, 1942, p. 72, doi : 10.15227 / orgsyn.022.0072 ; Coll. Vol. 3, 1955, p. 485 ( PDF ).

↑ Michael E. Jung, Michael H. Parker: Synthesis of Several Naturally Occurring Polyhalogenated Monoterpenes of the Halomon Class1 . In: The Journal of Organic Chemistry . tape 62 , no. 21 , October 1, 1997, p. 7094-7095 , doi : 10.1021 / jo971371 + , PMID 11671809 .

[Wiley-1] David W. Knight, Glen A. Russell: Phenyliodine (III) Dichloride . In: Encyclopedia of Reagents for Organic Synthesis . American Cancer Society, 2001, ISBN 978-0-470-84289-8 , doi : 10.1002 / 047084289X.rp071 .

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[3] EM Archer, TG van Schalkwyk: The crystal structure of benzene iododichloride . In: Acta Crystallographica . tape 6 , no. 1 , January 10, 1953, p. 88-92 , doi : 10.1107 / S0365110X53000193 ( iucr.org ).

[4] JV Carey, PA Chaloner, PB Hitchcock, T. Neugebauer, KR Seddon: Synthesis and Decomposition of Dichloroiodoarenes. An Improved Low Temperature X-Ray Structure of Dichloroiodobenzene and the Structure of 1-Chloro-2,3,5,6-tetrakis (chloromethyl) -4-methylbenzene. In: ChemInform . tape 27 , no. 52 , 1996, doi : 10.1002 / chin.199652032 .

[OrgSynth-5] H. J. Lucas and ER Kennedy: Iodobenzene dichloride In: Organic Syntheses . 22, 1942, p. 69, doi : 10.15227 / orgsyn.022.0069 ; Coll. Vol. 3, 1955, p. 482 ( PDF ).

[6] Atsuhiko Zanka, Hiroki Takeuchi, Ariyoshi Kubota: Large-Scale Preparation of Iodobenzene Dichloride and Efficient Monochlorination of 4-Aminoacetophenone . In: Organic Process Research & Development . tape 2 , no. 4 , July 1, 1998, pp. 270-273 , doi : 10.1021 / op980024e .

[7] Xue-Fei Zhao, Chi Zhang: Iodobenzene Dichloride as a Stoichiometric Oxidant for the Conversion of Alcohols into Carbonyl Compounds; Two Facile Methods for Its Preparation . In: Synthesis . tape 2007 , no. February 04 , 2007, p. 551-557 , doi : 10.1055 / s-2007-965889 .

[8] MW Formo and John R. Johnson: Iodoxybenzene: B. Hypochlorite oxidation of iodobenzene dichloride In: Organic Syntheses . 22, 1942, p. 72, doi : 10.15227 / orgsyn.022.0072 ; Coll. Vol. 3, 1955, p. 485 ( PDF ).

[9] Michael E. Jung, Michael H. Parker: Synthesis of Several Naturally Occurring Polyhalogenated Monoterpenes of the Halomon Class1 . In: The Journal of Organic Chemistry . tape 62 , no. 21 , October 1, 1997, p. 7094-7095 , doi : 10.1021 / jo971371 + , PMID 11671809 .