(2.2.2) Cryptand

Structural formula
General
Surname	[2.2.2] Cryptand
other names	4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo [8.8.8] hexacosane; Kryptofix ® 222; Crypt-222; [2.2.2] Cryptand;
Molecular formula	C 18 H 36 N 2 O 6
Brief description	white solid
External identifiers / databases
EC number	245-962-4
ECHA InfoCard	100,041,770
PubChem	72801
Wikidata	Q4596986
properties
Molar mass	376.49 g mol −1
Physical state	firmly
Melting point	68-71 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
Toxicological data	300–2000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

[2.2.2] Kryptand is a chemical compound from the group of cryptand compounds.

Extraction and presentation

The derivative dibenzo [2.2.2] cryptand can be obtained by a multistep reaction. Here, 1,2-dibromoethane and potassium carbonate in dimethylformamide are converted to 1,2-bis (2-nitrophenoxy) ethane, which is converted with a catalyst to a diamino derivative, which in turn reacts with 3,6-dioxaoctanediyl dichloride to form a lactam . This is reduced with lithium aluminum hydride to an aza-crown ether and then reacted with 1,2-ethylene- O , O- diglycolic acid chloride and diborane to form [2.2.2] cryptand.

properties

[2.2.2] Cryptand is a white solid that is able to form complexes (so-called cryptates ) with metal cations . In contrast to most other complexing agents, the bicyclic aminopolyethers also form stable complexes with alkali and alkaline earth metal ions.

use

[2.2.2] Cryptand is used together with potassium to reduce a distannin to a radical anion . It is used in nuclear medicine for the synthesis of special compounds (e.g. [ ¹⁸ F] - fluorodeoxyglucose ).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet 2.2.2-Cryptand, 98% from Sigma-Aldrich , accessed on May 31, 2017 ( PDF ).
^ Yousry MA Naguib: Synthesis of a [2.2.2] Cryptand Containing Reactive Functional Groups. In: Molecules. 14, 2009, p. 3600, doi: 10.3390 / molecules14093600 .
↑ Rolf K Freier: Volume 2, Aqueous Solutions / Aqueous Solutions - Supplements / supplements . Walter de Gruyter, 2011, ISBN 978-3-11-085236-3 , p. 470 ( limited preview in Google Book search).
^ Catherine E. Housecroft, AG Sharpe: Inorganic Chemistry . Pearson Education, 2005, ISBN 0-13-039913-2 , pp. 269 ( limited preview in Google Book search).
^ Hans-Jürgen Biersack, Leonard M. Freeman: Clinical Nuclear Medicine . Springer Science & Business Media, 2008, ISBN 978-3-540-28026-2 , pp. 67 ( limited preview in Google Book search).
^ Graham L. Patrick: An Introduction to Drug Synthesis . Oxford University Press, 2015, ISBN 978-0-19-870843-8 , pp. 383 ( limited preview in Google Book search).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet 2.2.2-Cryptand, 98% from Sigma-Aldrich , accessed on May 31, 2017 ( PDF ).

[DOI10.3390/molecules14093600-2] Yousry MA Naguib: Synthesis of a [2.2.2] Cryptand Containing Reactive Functional Groups. In: Molecules. 14, 2009, p. 3600, doi: 10.3390 / molecules14093600 .

[Rolf_K_Freier-3] Rolf K Freier: Volume 2, Aqueous Solutions / Aqueous Solutions - Supplements / supplements . Walter de Gruyter, 2011, ISBN 978-3-11-085236-3 , p. 470 ( limited preview in Google Book search).

[Catherine_E._Housecroft,_A._G._Sharpe-4] Catherine E. Housecroft, AG Sharpe: Inorganic Chemistry . Pearson Education, 2005, ISBN 0-13-039913-2 , pp. 269 ( limited preview in Google Book search).

[Hans-Jürgen_Biersack,_Leonard_M._Freeman-5] Hans-Jürgen Biersack, Leonard M. Freeman: Clinical Nuclear Medicine . Springer Science & Business Media, 2008, ISBN 978-3-540-28026-2 , pp. 67 ( limited preview in Google Book search).

[Graham_L._Patrick-6] Graham L. Patrick: An Introduction to Drug Synthesis . Oxford University Press, 2015, ISBN 978-0-19-870843-8 , pp. 383 ( limited preview in Google Book search).