N -iodosuccinimide

Structural formula
General
Surname	N -iodosuccinimide
other names	1-iodo-2,5-pyrrolidinedione ( IUPAC )
Molecular formula	C 4 H 4 INO 2
Brief description	colorless solid
External identifiers / databases
EC number	208-221-6
ECHA InfoCard	100.007.475
PubChem	120273
ChemSpider	107372
Wikidata	Q27124017
properties
Molar mass	224.98 g mol −1
Physical state	firmly
Melting point	202-206 ° C
solubility	Soluble in acetone , insoluble in diethyl ether
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-319-335
	P: 261-305 + 351 + 338
Toxicological data	180 mg kg −1 ( LD 50 , mouse , iv )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N -iodosuccinimide , usually referred to as NIS for short, is the imide of succinic acid iodinatedon the nitrogen . It is thus the iodine analog of N -chlorosuccinimide (NCS) and N -bromosuccinimide (NBS) that are used for similar applications.

Extraction and presentation

Was shown for the first time N -Iodsuccinimid 1870 by Bunge by reacting Silbersuccinimid with iodine in ether or acetone .

use

N -iodosuccinimide is used in organic chemistry for the iodination of alkenes and aromatics and as a mild oxidizing agent.

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet N-Iodosuccinimide from Sigma-Aldrich , accessed on December 15, 2019 ( PDF ).
^ ^A ^b N. Bunge: Effect of haloids on metal derivatives of some carbon compounds . In: Friedrich Wöhler , Justus Liebig , Hermann Kopp (Hrsg.): Annalen der Chemie und Pharmacie . 7. Supplement band. CF Winter'sche Verlagshandlung, Leipzig and Heidelberg 1870, p. 117 .
↑ Piotr Pawluć, Grzegorz Hreczycho, Justyna Szudkowska, Maciej Kubicki, Bogdan Marciniec: New One-Pot Synthesis of (E) -β-Aryl Vinyl Halides from Styrenes . In: Organic Letters . tape 11 , no. 15 , August 6, 2009, p. 3390-3393 , doi : 10.1021 / ol901233j .
↑ Daugirdas T. Racys, Catherine E. Warrilow, Sally L. Pimlott, Andrew Sutherland: Highly Regioselective Iodination of Arenes via Iron (III) -Catalyzed Activation of N-Iodosuccinimide . In: Organic Letters . tape 17 , no. 19 , October 2, 2015, p. 4782-4785 , doi : 10.1021 / acs.orglett.5b02345 .
↑ GK Surya Prakash, Thomas Mathew, Dushyanthi Hoole, Pierre M. Esteves, Qi Wang: N-Halosuccinimide / BF ₃- H ₂ O, Efficient Electrophilic Halogenating Systems for Aromatics . In: Journal of the American Chemical Society . tape 126 , no. 48 , December 2004, p. 15770–15776 , doi : 10.1021 / ja0465247 .
↑ Scott C. Virgil, Ying Zeng, Fanzuo Kong, Julie A. Pigza: N -Iodosuccinimide . In: Encyclopedia of Reagents for Organic Synthesis . John Wiley & Sons, Ltd, Chichester, UK 2007, ISBN 978-0-471-93623-7 , pp. ri038.pub3 , doi : 10.1002 / 047084289x.ri038.pub3 .

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet N-Iodosuccinimide from Sigma-Aldrich , accessed on December 15, 2019 ( PDF ).

[Bunge-2] A ^b N. Bunge: Effect of haloids on metal derivatives of some carbon compounds . In: Friedrich Wöhler , Justus Liebig , Hermann Kopp (Hrsg.): Annalen der Chemie und Pharmacie . 7. Supplement band. CF Winter'sche Verlagshandlung, Leipzig and Heidelberg 1870, p. 117 .

[3] Piotr Pawluć, Grzegorz Hreczycho, Justyna Szudkowska, Maciej Kubicki, Bogdan Marciniec: New One-Pot Synthesis of (E) -β-Aryl Vinyl Halides from Styrenes . In: Organic Letters . tape 11 , no. 15 , August 6, 2009, p. 3390-3393 , doi : 10.1021 / ol901233j .

[4] Daugirdas T. Racys, Catherine E. Warrilow, Sally L. Pimlott, Andrew Sutherland: Highly Regioselective Iodination of Arenes via Iron (III) -Catalyzed Activation of N-Iodosuccinimide . In: Organic Letters . tape 17 , no. 19 , October 2, 2015, p. 4782-4785 , doi : 10.1021 / acs.orglett.5b02345 .

[5] GK Surya Prakash, Thomas Mathew, Dushyanthi Hoole, Pierre M. Esteves, Qi Wang: N-Halosuccinimide / BF ₃- H ₂ O, Efficient Electrophilic Halogenating Systems for Aromatics . In: Journal of the American Chemical Society . tape 126 , no. 48 , December 2004, p. 15770–15776 , doi : 10.1021 / ja0465247 .

[6] Scott C. Virgil, Ying Zeng, Fanzuo Kong, Julie A. Pigza: N -Iodosuccinimide . In: Encyclopedia of Reagents for Organic Synthesis . John Wiley & Sons, Ltd, Chichester, UK 2007, ISBN 978-0-471-93623-7 , pp. ri038.pub3 , doi : 10.1002 / 047084289x.ri038.pub3 .