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4-Nitroaniline
Names
Preferred IUPAC name
Systematic IUPAC name
Other names
p p
Identifiers
CAS Number
3D model (JSmol )
Beilstein Reference
508690
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.555
EC Number
Gmelin Reference
27331
KEGG
PubChem CID
RTECS number
UNII
UN number
1661
CompTox Dashboard (EPA )
InChI=1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9 )10/h1-4H,7H2 N
Key: TYMLOMAKGOJONV-UHFFFAOYSA-N N
InChI=1/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9 )10/h1-4H,7H2
Key: TYMLOMAKGOJONV-UHFFFAOYAW
Properties
Chemical formula
C 6 H 6 N 2 O 2
Molar mass
138.12 g/mol
Appearance
yellow or brown powder
Odor
faint, ammonia-like
Density
1.437 g/ml, solid
Melting point
146 to 149 °C (295 to 300 °F; 419 to 422 K ) (lit.)
Boiling point
332 °C (630 °F; 605 K )
Solubility in water
0.8 mg/ml at 18.5 °C (IPCS)
Vapor pressure
0.00002 mmHg (20°C)[1]
Magnetic susceptibility (χ)
-66.43·10−6 cm 3
Hazards
Occupational safety and health
Main hazards
Toxic
GHS labelling
Pictograms
Signal word
Warning
Hazard statements
H301 , H311 , H331 , H373 , H412
Precautionary statements
P260 , P261 , P264 , P270 , P271 , P273 , P280 , P301+P310 , P302+P352 , P304+P340 , P311 , P312 , P314 , P321 , P322 , P330 , P361 , P363 , P403+P233 , P405 , P501
NFPA 704
Flash point
199 °C (390 °F; 472 K )
Lethal dose or concentration (LD, LC):
LD 50 median dose )
3249 mg/kg (rat, oral)[2]
NIOSH
PEL (Permissible)
TWA 6 mg/m3 (1 ppm) [skin][1]
REL (Recommended)
TWA 3 mg/m3 [1]
IDLH (Immediate danger)
300 mg/m3 [1]
Safety data sheet (SDS)
JT Baker
Related compounds
Related compounds
2-Nitroaniline , 3-Nitroaniline
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
4-Nitroaniline , p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6 H 6 N 2 O 2 [3]
Synthesis
[ edit ]
4-Nitroaniline is produced industrially via the amination of 4-nitrochlorobenzene :[3]
ClC6 H 4 NO 2 3 2 NC 6 H 4 NO 2 4 Cl
Below is a laboratory synthesis of 4-nitroaniline from aniline . The key step in this reaction sequence is an electrophilic aromatic substitution to install the nitro group para to the amino group. The amino group can be easily protonated and become a meta director. Therefore, a protection of the acetyl group is required. After this reaction, a separation must be performed to remove 2-nitroaniline, which is also formed in a small amount during the reaction.[4]
Applications
[ edit ]
4-Nitroaniline is mainly consumed industrially as a precursor to p [3]
It is a starting material for the synthesis of Para Red , the first azo dye :[5]
Synthesis of Para Red
Laboratory use
[ edit ]
Nitroaniline undergoes diazotization , which allows access to 1,4-dinitrobenzene [6] [7] isocyanate .[8] [9]
Carbon snake demonstration
[ edit ]
When heated with sulfuric acid, it dehydrates and polymerizes explosively into a rigid foam.[10]
In Carbon snake demo, paranitroaniline can be used instead of sugar, if the experiment is allowed to proceed under an obligatory fumehood .[11] [12] explosion if too much sulfuric acid is used.[13]
Toxicity
[ edit ]
The compound is toxic by way of inhalation, ingestion, and absorption, and should be handled with care. Its LD 50 [14]
See also
[ edit ]
References
[ edit ]
^ "p-Nitroaniline" . Immediately Dangerous to Life or Health Concentrations (IDLH) . National Institute for Occupational Safety and Health (NIOSH).
^ a b c Booth, Gerald (2003-03-11). "Nitro Compounds, Aromatic" . In Wiley-VCH (ed.). Ullmann's Encyclopedia of Industrial Chemistry doi :10.1002/14356007.a17_411 . ISBN 978-3-527-30385-4
^ Mohrig, J.R.; Morrill, T.C.; Hammond, C.N.; Neckers, D.C. (1997). "Synthesis 5: Synthesis of the Dye Para Red from Aniline" . Experimental Organic Chemistry . New York, NY: Freeman. pp. 456–467. Archived from the original on 2020-09-15. Retrieved 2007-07-18 .
^ Williamson, Kenneth L. (2002). Macroscale and Microscale Organic Experiments, Fourth Edition Houghton-Mifflin . ISBN 0-618-19702-8
^ Starkey, E. B. (1939). "p-DINITROBENZENE" . Organic Syntheses . 19 doi :10.15227/orgsyn.019.0040 .
^ "p-NITROPHENYLARSONIC ACID" . Organic Syntheses . 26 doi :10.15227/orgsyn.026.0060 .
^ Shriner, R. L.; Horne, W. H.; Cox, R. F. B. (1934). "p-NITROPHENYL ISOCYANATE" . Organic Syntheses . 14 doi :10.15227/orgsyn.014.0072 .
^ "2,6-DIIODO-p-NITROANILINE" . Organic Syntheses . 12 doi :10.15227/orgsyn.012.0028 .
^ Poshkus, A. C.; Parker, J. A. (1970). "Studies on nitroaniline–sulfuric acid compositions: Aphrogenic pyrostats" . Journal of Applied Polymer Science . 14 8 ): 2049–2064. doi :10.1002/app.1970.070140813 .
^ Summerlin, Lee R.; Ealy, James L. (1988). "Experiment 100: Dehydration of p-Nitroaniline: Sanke and Puff". Chemical Demonstrations: A Sourcebook for Teachers Volume 1 American Chemical Society . p. 171. ISBN 978-0-841-21481-1
^ "Carbon Snake: demonstrating the dehydration power of concentrated sulfuric acid" . communities.acs.org . 2013-06-06. Retrieved 2022-01-31 .
^ Making a carbon snake with P-Nitroaniline , retrieved 2022-01-31
^ "4-Nitroaniline" . St. Louis, Missouri: Sigma-Aldrich. December 18, 2020.
External links
[ edit ] R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=4-Nitroaniline&oldid=1201492482 " C a t e g o r i e s : ● A n i l i n e s ● D y e s ● H a z a r d o u s a i r p o l l u t a n t s ● I A R C G r o u p 3 c a r c i n o g e n s ● N i t r o b e n z e n e d e r i v a t i v e s ● C o r r o s i o n i n h i b i t o r s H i d d e n c a t e g o r i e s : ● A r t i c l e s w i t h c h a n g e d E B I i d e n t i f i e r ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● A r t i c l e s w i t h c h a n g e d I n C h I i d e n t i f i e r ● C h e m b o x h a v i n g G H S d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● C h e m b o x i m a g e s i z e s e t ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a ● C o m m o n s c a t e g o r y l i n k f r o m W i k i d a t a
● T h i s p a g e w a s l a s t e d i t e d o n 3 1 J a n u a r y 2 0 2 4 , a t 1 9 : 2 6 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
