2,4,7-trinitrofluorenone

Structural formula
General
Surname	2,4,7-trinitrofluorenone
other names	2,4,7-trinitro-9 H -fluoren-9-one ( IUPAC ) ; TNF;
Molecular formula	C 13 H 5 N 3 O 7
Brief description	yellow crystal needles
External identifiers / databases
EC number	204-965-0
ECHA InfoCard	100.004.515
PubChem	8521
ChemSpider	8207
Wikidata	Q22133107
properties
Molar mass	315.2 g mol −1
Physical state	firmly
Melting point	175.2-176 ° C
solubility	poorly soluble in water
safety instructions
H and P phrases	H: 201-319
	P: 210-250-280-305 + 351 + 338-370 + 372 + 380 + 373
Toxicological data	9910 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,4,7-Trinitrofluorenone is a chemical compound from the group of aromatic nitro compounds .

presentation

1905 described Julius Schmidt and Karl Bauer the synthesis of 2,6,7-trinitrofluorenone by nitration of fluorenone 1 with nitrating acid . Alternative syntheses - the nitration of 2,5-dinitrofluorenone 2 or 2,7-dinitrofluorenone 3 - showed in 1943 that the compound described in 1905 is 2,4,7-trinitrofluorenone 4 .

Synthesis of 2,4,7-trinitrofluorenone

use

Like picric acid , 2,6,7-trinitrofluorenone also forms stable colored electron donor acceptor complexes with a sharp melting point with numerous polycyclic aromatic hydrocarbons , which are suitable for characterizing and purifying these hydrocarbons.

2,6,7-Trinitrofluorenone is used as a sensitizer in the manufacture of photorefractive polymer composites .

Individual evidence

↑ ^a ^b ^c ^d ^e Entry on 2,4,7-trinitrofluoren-9-one in the GESTIS substance database of the IFA , accessed on March 2, 2020 (JavaScript required)
↑ ^a ^b Safety Data Sheet 2,4,7-Trinitro-9-fluorenone - Wetted with approx. 20% water. (PDF) Biosynth Carbosynth, May 28, 2015, accessed on March 2, 2020 .
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 2,4,7-trinitrofluoren-9-ones in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 2, 2020, is shown, which is derived from a self-classification by the distributor .
↑ Julius Schmidt, Karl Bauer: About the action of nitric acid on fluorenone and the derivatives of the resulting nitro derivatives . In: Reports of the German Chemical Society . tape 38 , no. 4 , November 1905, p. 3758 , doi : 10.1002 / cber.19050380411 .
^ Francis Earl Ray, William C. Francis: Polynitro Compounds Of Fluorene . In: The Journal of Organic Chemistry . tape 08 , no. 1 , January 1943, p. 52 , doi : 10.1021 / jo01189a009 .
↑ Milton Orchin, E. Oscar Woolfolk: Molecular Complexes with 2,4,7-Trinitrofluorenone . In: Journal of the American Chemical Society . tape 68 , no. 9 , September 1946, p. 1727 , doi : 10.1021 / ja01213a014 .
↑ Norman L. Allinger et al. a .: Organic chemistry . Walter de Gruyter , Berlin, New York 1980, ISBN 978-3-11-082970-9 , pp. 916 ( limited preview in Google Book search).
↑ Boris L. Volodin, Klaus Meerholz, Sandalphon, Bernard Kippelen, Nasser Peyghambarian: Azo dye-doped photorefractive polymers . In: Proceedings of SPIE - The International Society for Optical Engineering . tape 2144 , June 2, 1994, pp. 71-81 , doi : 10.1117 / 12.177217 .

[Gestis-1] Entry on 2,4,7-trinitrofluoren-9-one in the GESTIS substance database of the IFA , accessed on March 2, 2020 (JavaScript required)

[Biosynth-2] Safety Data Sheet 2,4,7-Trinitro-9-fluorenone - Wetted with approx. 20% water. (PDF) Biosynth Carbosynth, May 28, 2015, accessed on March 2, 2020 .

[3] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 2,4,7-trinitrofluoren-9-ones in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 2, 2020, is shown, which is derived from a self-classification by the distributor .

[4] Julius Schmidt, Karl Bauer: About the action of nitric acid on fluorenone and the derivatives of the resulting nitro derivatives . In: Reports of the German Chemical Society . tape 38 , no. 4 , November 1905, p. 3758 , doi : 10.1002 / cber.19050380411 .

[5] Francis Earl Ray, William C. Francis: Polynitro Compounds Of Fluorene . In: The Journal of Organic Chemistry . tape 08 , no. 1 , January 1943, p. 52 , doi : 10.1021 / jo01189a009 .

[6] Milton Orchin, E. Oscar Woolfolk: Molecular Complexes with 2,4,7-Trinitrofluorenone . In: Journal of the American Chemical Society . tape 68 , no. 9 , September 1946, p. 1727 , doi : 10.1021 / ja01213a014 .

[7] Norman L. Allinger et al. a .: Organic chemistry . Walter de Gruyter , Berlin, New York 1980, ISBN 978-3-11-082970-9 , pp. 916 ( limited preview in Google Book search).

[VoMeSaKi-8] Boris L. Volodin, Klaus Meerholz, Sandalphon, Bernard Kippelen, Nasser Peyghambarian: Azo dye-doped photorefractive polymers . In: Proceedings of SPIE - The International Society for Optical Engineering . tape 2144 , June 2, 1994, pp. 71-81 , doi : 10.1117 / 12.177217 .