Aminobenzotrifluoride

Aminobenzotrifluoride
Surname	2-aminobenzotrifluoride	3-aminobenzotrifluoride	4-aminobenzotrifluoride
other names	2- (trifluoromethyl) aniline α, α, α-trifluoro- o -toluidine	3- (trifluoromethyl) aniline α, α, α-trifluoro- m -toluidine	4- (trifluoromethyl) aniline α, α, α-trifluoro- p -toluidine
Structural formula
CAS number	88-17-5	98-16-8	455-14-1
ECHA InfoCard	100,001,642	100.002.404	100.006.579
PubChem	6922	7375	9964
Molecular formula	C 7 H 6 F 3 N
Molar mass	161.13 g mol −1
Physical state	liquid
Brief description	yellow to brown liquids with an unpleasant amine-like odor
Melting point	−33 ° C	5 ° C	3 ° C
boiling point	171 ° C	187 ° C	83 ° C (16 hPa)
density	1.29 g cm −3 (20 ° C)	1.295 g cm −3 (20 ° C)	1.295 g cm −3 (20 ° C)
Vapor pressure	1.3 hPa (20 ° C)	0.865 hPa (20 ° C)	1 hPa (38 ° C)
solubility	poorly soluble in water (~ 5 g l −1 at 20 ° C)
Refractive index	1.481 (20 ° C)	1.480 (20 ° C)	1.483 (20 ° C)
GHS labeling	danger	danger	danger
H and P phrases	302-315-317-319-373-411	302-312-330-315-318-335-373-411	301-319-410
	261-280-301 + 310-311	280-301 + 330 + 331-302 + 352 304 + 340-305 + 351 + 338-332 + 313-310	273-305 + 351 + 338-314
LD 50	480 mg kg −1 (oral rat)	480 mg kg −1 (oral rat)	128 mg kg −1 (oral rat)

Aminobenzotrifluorides are chemical compounds from the group of halogenated benzene derivatives , which are derived from benzotrifluoride . Depending on the position of the amino group in relation to the trifluoromethyl group , there are three isomers .

Extraction and presentation

3-aminobenzotrifluoride can be synthesized from benzotrifluoride by nitration with nitric acid to 3-nitrobenzotrifluoride and its subsequent reduction (catalytic hydrogenation). The other two isomers are also formed to a lesser extent. By initially chlorinating benzotrifluoride (which later has to be reversed by catalytic hydrogenation) and thus blocking the 3-position, the yield of 2-aminobenzotrifluoride can be greatly increased.

properties

Aminobenzotrifluorides are yellow to brown, slightly volatile liquids with an unpleasant odor, which are sparingly water-soluble. They decompose when heated strongly in the presence of air, producing hydrogen fluoride , carbon monoxide , carbon dioxide and nitrous gases .

use

3-aminobenzotrifluoride is used as an intermediate in the manufacture of pesticides (e.g. fluometuron and flurochloridone ) and pharmaceuticals (e.g. flufenamic acid ). 4-aminobenzotrifluoride is also used as an intermediate in the manufacture of drugs (e.g. leflunomide or teriflunomide ).

safety instructions

The vapors of aminobenzotrifluoride can form an explosive mixture with air ( flash point 55–85 ° C, ignition temperature 600 ° C).

Individual evidence

1. ↑ ^{a b c d e f g h} Entry on 2-aminobenzotrifluoride in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
2. ↑ ^{a b c d e f g h i j k} Entry on 3-aminobenzotrifluoride in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
3. ↑ ^{a b c d e f g} Entry on 4-aminobenzotrifluoride in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
4. ↑ ^{a b} Data sheet 4-aminobenzotrifluoride (PDF) from Merck , accessed on December 27, 2019.
5. ↑ Data sheet 2-aminobenzotrifluoride from Sigma-Aldrich , accessed on December 27, 2019 ( PDF ).
6. ↑ Data sheet 3-aminobenzotrifluoride from Sigma-Aldrich , accessed on December 27, 2019 ( PDF ).
7. ↑ Data sheet 4-aminobenzotrifluoride from Sigma-Aldrich , accessed on December 27, 2019 ( PDF ).
8. ↑ Data sheet 2-aminobenzotrifluoride (PDF) from Merck , accessed on December 27, 2019.
9. ↑ Alain Tressaud: Fluorine and the Environment ; ISBN 978-0-44452672-4 , p. 125 ( limited preview in Google book search).
10. ↑ Ronald Eric Banks: Fluorine in agriculture ; ISBN 978-1-85957033-3 .
11. ↑ Paul Knochel: Modern solvents in organic synthesis ; ISBN 978-3-540-66213-6 , p. 84.
12. ^ A process for preparing Teriflunomide .