Bis (morpholino) methane

Structural formula
General
Surname	Bis (morpholino) methane
other names	4,4'-methylenedimorpholine ( IUPAC ) ; N , N ′ -methylene bismorpholine; 4,4'-methylene-bis-morpholine; Methylenebistrahydro-1,4-oxazine; Methylene-bis-oxazine; Dimorpholinomethane; Bismorpholinomethane;
Molecular formula	C 9 H 18 N 2 O 2
Brief description	slowly melting solid
External identifiers / databases
EC number	227-062-3
ECHA InfoCard	100.024.603
PubChem	21839
ChemSpider	20526
Wikidata	Q865946
properties
Molar mass	186.25 g mol −1
Physical state	firmly
boiling point	122-124 ° C (12 mmHg )
solubility	soluble in water; soluble in organic solvents;
safety instructions
H and P phrases	H: 302-312-332-314-317-341-350-373
	EUH: 071
	P: 280-301 + 330 + 331-303 + 361 + 353-304 + 340-305 + 351 + 338-310
Toxicological data	1000 mg kg −1 ( LD 50 , rat , sc )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bis (morpholino) methane is a chemical compound from the group of nitrogen - oxygen - heterocycles .

Extraction and presentation

Bis (morpholino) methane can be obtained by reacting formaldehyde with morpholine .

use

Bis (morpholino) methane is a formaldehyde-releasing preservative and is used as a component of cooling lubricants . It is a useful reagent for electron-rich heterocycles ( pyrroles , indoles ) and active methylene compounds in the presence of trifluoroacetic acid .

Individual evidence

↑ ^a ^b ^c data sheet bis (4-morpholinyl) methane from AlfaAesar, accessed on December 29, 2019 ( PDF )(JavaScript required) .
↑ Wilfried Paul Microbicides for the protection of materials . ISBN 978-0-412-53450-8 ( p. 109 in Google Book Search USA ).
↑ ^a ^b Entry on bis (morpholino) methane in the GESTIS substance database of the IFA , accessed on January 21, 2020(JavaScript required) .
↑ Entry on N, N'-methylenebismorpholine Template: link text check / apostrophe in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 29, 2019. Manufacturers and / or distributors can expand the harmonized classification and labeling .
↑ Data sheet 4,4′-METHYLENE DIMORPHOLINE from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).
↑ ^a ^b Harry Heaney, George Papageorgiou, Robert F. Wilkins: The generation of iminium ions using chlorosilanes and their reactions with electron rich aromatic heterocycles. In: Tetrahedron. 53, 1997, pp. 2941-2958, doi : 10.1016 / S0040-4020 (96) 01174-X .
↑ Werner Baumann, Bettina Herberg-Liedtke: Chemicals in metal processing. 1995, p. 1157, ISBN 978-3-5406-0094-7 ( limited preview in Google book search).

[Alfa-1] ta sheet bis (4-morpholinyl) methane from AlfaAesar, accessed on December 29, 2019 ( PDF )(JavaScript required) .

[2] Wilfried Paul Microbicides for the protection of materials . ISBN 978-0-412-53450-8 ( p. 109 in Google Book Search USA ).

[GESTIS-3] Entry on bis (morpholino) methane in the GESTIS substance database of the IFA , accessed on January 21, 2020(JavaScript required) .

[CLP_100.024.603-4] Entry on N, N'-methylenebismorpholine Template: link text check / apostrophe in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 29, 2019. Manufacturers and / or distributors can expand the harmonized classification and labeling .

[Sigma-5] Data sheet 4,4′-METHYLENE DIMORPHOLINE from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).

[Tetrahedron-6] Harry Heaney, George Papageorgiou, Robert F. Wilkins: The generation of iminium ions using chlorosilanes and their reactions with electron rich aromatic heterocycles. In: Tetrahedron. 53, 1997, pp. 2941-2958, doi : 10.1016 / S0040-4020 (96) 01174-X .

[7] Werner Baumann, Bettina Herberg-Liedtke: Chemicals in metal processing. 1995, p. 1157, ISBN 978-3-5406-0094-7 ( limited preview in Google book search).