Nitrotoluidines

In chemistry, the nitrotoluidines are a group of substances that are derived from nitrobenzene , toluene  (methylbenzene) and aniline  (aminobenzene). The structure consists of a benzene ring with attached nitro  (–NO ₂ ), methyl  (–CH ₃ ) and amino  (–NH ₂ ) groups as substituents . Their different arrangement results in ten constitutional isomers with the empirical formula C ₇ H ₈ N ₂ O ₂ .

If one proceeds from the disubstituted parent compounds, then one can regard the nitrotoluidines as methyl derivatives of nitroanilines , as amino derivatives of nitrotoluenes or as nitro derivatives of toluidines . The naming followed the last variant because the toluidines are the only ones of the three disubstituted parent compounds that form a completely separate name.

Nitrotoluidines can be obtained by nitration of acetyltoluidines with mixed acid and subsequent hydrolysis (e.g. 2-nitro- p -toluidine from N -acetyl- p -toluidine ). They are used as intermediate products in the manufacture of azo dyes . Thus, 2-nitro- p -toluidine serves as the diazo component in C.1. Pigment Yellow 1 and C.1. Pigment Red 3. 5-Nitro-o-toluidine must not be released after reductive cleavage of azo groups from textiles or leather products that come into direct contact with human skin for a long period of time (Appendix 1 of the Consumer Goods Ordinance ).

Nitrotoluidines
Trunk connection
	o -Toluidine
Structural formula
Surname	1-amino-2-methyl-3-nitrobenzene 3-nitro- o -toluidine	1-amino-2-methyl-4-nitrobenzene 4-nitro- o -toluidine	1-amino-2-methyl-5-nitrobenzene 5-nitro- o -toluidine	1-amino-2-methyl-6-nitrobenzene 6-nitro- o -toluidine
CAS number	603-83-8	99-52-5	99-55-8	570-24-1
ECHA InfoCard	100.009.145	100.002.511	100.002.514	100,008,482
PubChem	11783	7441	7444	11298
Molecular formula	C 7 H 8 N 2 O 2
Molar mass	152.16 g mol −1
Physical state	firmly
Brief description		yellow odorless powder	yellow odorless powder
Melting point	88-90 ° C	131-133 ° C	107-108 ° C	93-96 ° C
boiling point	305 ° C	> 300 ° C (decomposition)	> 130 ° C (decomposition)
density			1.365 g cm −3
solubility		practically insoluble in water
GHS labeling	danger		danger	danger
H and P phrases	301-311-331-373-411		301-311-331-351-412	301-311-331-373-411
	261-273-280-301 + 310-311

Nitrotoluidines
Trunk connection
	m -toluidine
Structural formula
Surname	1-amino-3-methyl-2-nitrobenzene 2-nitro- m -toluidine	1-amino-3-methyl-4-nitrobenzene 4-nitro- m- toluidine	1-amino-3-methyl-5-nitrobenzene 5-nitro- m -toluidine	1-amino-3-methyl-6-nitrobenzene 6-nitro- m -toluidine
CAS number	601-87-6	611-05-2	618-61-1	578-46-1
ECHA InfoCard		100.009.317		100.008.568
PubChem	69038	11898	3565037	11356
Molecular formula	C 7 H 8 N 2 O 2
Molar mass	152.16 g mol −1
Physical state	firmly
Brief description		yellow red powder		orange powder
Melting point		131-136 ° C		110-111 ° C
boiling point
density
solubility		soluble in tetrahydrofuran
GHS labeling	danger
H and P phrases	301-311-331-373-411
	?	?	?	261-273-280-301 + 310-311

Nitrotoluidines
Trunk connection
	p -toluidine
Structural formula
Surname	1-amino-4-methyl-2-nitrobenzene 2-nitro- p -toluidine	1-amino-4-methyl-3-nitrobenzene 3-nitro- p -toluidine
CAS number	89-62-3	119-32-4
ECHA InfoCard	100.001.750	100.003.922
PubChem	6978	8390
Molecular formula	C 7 H 8 N 2 O 2
Molar mass	152.16 g mol −1
Physical state	firmly
Brief description	orange powder with a characteristic odor
Melting point	116 ° C	74-77 ° C
boiling point	210 ° C (decomposition)
density	1.31 g cm −3
solubility	Very sparingly soluble in water soluble in ethanol and chloroform
GHS labeling	danger
H and P phrases	301-311-331-373-411
	261-273-280-301 + 310-311

Individual evidence

1. ↑ ^{a b c} Toxicological assessment of 2-nitro-4-methylaniline (PDF) from the trade association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.
2. ↑ ^{a b c d} Entry on 4-nitro-o-toluidine in the GESTIS substance database of the IFA , accessed on September 27, 2019(JavaScript required) .
3. ↑ ^{a b c d} Entry on 5-nitro-o-toluidine in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
4. ↑ ^{a b c} data sheet 2-Methyl-3-nitroaniline from Sigma-Aldrich , accessed on November 3, 2016 ( PDF ).
5. ↑ ^{a b} Data sheet 2-Methyl-6-nitroaniline from Sigma-Aldrich , accessed on November 3, 2016 ( PDF ).
6. ↑ 2-Methyl-4-nitroaniline data sheet from Sigma-Aldrich , accessed on November 3, 2016 ( PDF ).
7. ↑ Data sheet 2-Methyl-5-nitroaniline from Sigma-Aldrich , accessed on December 27, 2019 ( PDF ).
8. ↑ ^{a b} Entry on 4-nitro-m-toluidine at TCI Europe, accessed on December 27, 2019.
9. ↑ ^{a b} Data sheet 5-Methyl-2-nitroaniline from Sigma-Aldrich , accessed on December 27, 2019 ( PDF ).
10. ↑ Entry on nitrotoluidine, isomers in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
11. ↑ ^{a b c d} Entry on 2-nitro-p-toluidine in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
12. ↑ Entry on 3-nitro-p-toluidine in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
13. ↑ Data sheet 4-Methyl-2-nitroaniline from Sigma-Aldrich , accessed on December 27, 2019 ( PDF ).
14. ↑ Data sheet 4-Methyl-3-nitroaniline from Sigma-Aldrich , accessed on December 27, 2019 ( PDF ).

Web links

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