Nitroanisidines

The nitroanisidines form a group of substances that are derived from nitrobenzene , anisole  (methoxybenzene) and aniline  (aminobenzene). The structure consists of a benzene ring with attached nitro  (–NO ₂ ), methoxy  (–OCH 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 ₃ .

If one proceeds from the disubstituted parent compounds, then one can consider the nitroanisidines as methoxy derivatives of nitroanilines , as amino derivatives of nitroanisoles or as nitro derivatives of anisidines . The naming followed the last variant because the anisidines are the only ones of the three disubstituted parent compounds that form a completely separate name.

Nitroanisidines
Trunk connection
	o -anisidine
Structural formula
Surname	1-amino-2-methoxy-3-nitrobenzene 3-nitro- o- anisidine	1-amino-2-methoxy-4-nitrobenzene 4-nitro- o- anisidine	1-amino-2-methoxy-5-nitrobenzene 5-nitro- o- anisidine	1-amino-2-methoxy-6-nitrobenzene 6-nitro- o- anisidine
CAS number	85-45-0	97-52-9	99-59-2	16554-45-3
ECHA InfoCard	100.001.462	100.002.354	100.002.518	100.036.910
PubChem	66559	7337	7447	85491
Molecular formula	C 7 H 8 N 2 O 3
Molar mass	168.15 g mol −1
Physical state	firmly
Brief description		yellow odorless powder	orange powder
Melting point		140-142 ° C / 139-143 ° C	118 ° C	73-78 ° C
boiling point		> 260 ° C (decomposition)
density		1.45 g cm −3
solubility		0.2 g / l at 20 ° C in water
GHS labeling		Caution	Caution	Caution
H and P phrases		302-351-411	315-319-335	302 + 312 + 332-315-319-335
		280-301 + 312 + 330	261-305 + 351 + 338	301 + 330 + 331-302 + 352

Nitroanisidines
Trunk connection
	m -anisidine
Structural formula
Surname	1-amino-3-methoxy-2-nitrobenzene 2-nitro- m- anisidine	1-amino-3-methoxy-4-nitrobenzene 4-nitro- m- anisidine	1-amino-3-methoxy-5-nitrobenzene 5-nitro- m- anisidine	1-amino-3-methoxy-6-nitrobenzene 6-nitro- m- anisidine
CAS number	16554-47-5	16292-88-9	586-10-7	16133-49-6
ECHA InfoCard			100.197.662	100.036.615
PubChem	10464700	2755795	2759598	85300
Molecular formula	C 7 H 8 N 2 O 3
Molar mass	168.15 g mol −1
Physical state	firmly
Brief description
Melting point				125-127 ° C
boiling point
density
solubility
GHS labeling				Caution
H and P phrases				302 + 312 + 332-315-319-335
				301 + 330 + 331-302 + 352

Nitroanisidines
Trunk connection
	p -anisidine
Structural formula
Surname	1-amino-4-methoxy-2-nitrobenzene 2-nitro- p- anisidine	1-amino-4-methoxy-3-nitrobenzene 3-nitro- p- anisidine
CAS number	96-96-8	577-72-0
ECHA InfoCard	100.002.317	100.110.092 100.209.982
PubChem	66793	123071
Molecular formula	C 7 H 8 N 2 O 3
Molar mass	168.15 g mol −1
Physical state	firmly
Brief description	orange to purple odorless powder
Melting point	123-126 ° C
boiling point
density
solubility
GHS labeling	danger	Caution
H and P phrases	330-310-300-373-412	317-319
	260-264-273-280-284-302 + 350	280-305 + 351 + 338

Individual evidence

1. ↑ ^{a b c d e f} Entry on 4-Nitro-o-anisidine in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
2. ↑ ^{a b c} Entry on 5-nitro-o-anisidine in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
3. ↑ Data sheet 2-Methoxy-4-nitroaniline from Sigma-Aldrich , accessed on December 27, 2019 ( PDF ).
4. ↑ ^{a b} Data sheet 2-Methoxy-6-nitroaniline, 97% from AlfaAesar, accessed on December 27, 2019 ( PDF )(JavaScript required) .
5. ↑ ^{a b} Data sheet 5-Methoxy-2-nitroaniline, 98% from AlfaAesar, accessed on December 27, 2019 ( PDF )(JavaScript required) .
6. ↑ ^{a b} Entry on 2-nitro-p-anisidine in the GESTIS substance database of the IFA , accessed on December 27, 2019(JavaScript required) .
7. ↑ Data sheet 4-Methoxy-2-nitroaniline from Sigma-Aldrich , accessed on December 27, 2019 ( PDF ).
8. ^ 4-Methoxy-3-nitroaniline. (pdf) Matrix Scientific, February 10, 2017, accessed December 27, 2019 . 

Web links

Commons : Nitroanisidine  - Collection of pictures, videos and audio files

• The Carcinogenic Potency Project: 5-Nitro-o-anisidine
• Paul E. Fanta and DS Tarbell: 2-Nitro-4-Methoxyaniline In: Organic Syntheses . 25, 1945, p. 78, doi : 10.15227 / orgsyn.025.0078 ; Coll. Vol. 3, 1955, p. 661 ( PDF ).