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● H e l p ● L e a r n t o e d i t ● C o m m u n i t y p o r t a l ● R e c e n t c h a n g e s ● U p l o a d f i l e
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( T o p )
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T o g g l e t h e t a b l e o f c o n t e n t s
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1 7 l a n g u a g e s
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P r i n t / e x p o r t
● D o w n l o a d a s P D F ● P r i n t a b l e v e r s i o n
I n o t h e r p r o j e c t s
● W i k i m e d i a C o m m o n s
A p p e a r a n c e
F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
o [1]
Names
Preferred IUPAC name
Other names
o
Identifiers
CAS Number
3D model (JSmol )
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.210
EC Number
PubChem CID
RTECS number
UNII
UN number
1673
CompTox Dashboard (EPA )
InChI=1S/C6H8N2/c7-5-3-1-2-4-6(5 )8/h1-4H,7-8H2 Y
Key: GEYOCULIXLDCMW-UHFFFAOYSA-N Y
InChI=1/C6H8N2/c7-5-3-1-2-4-6(5 )8/h1-4H,7-8H2
Key: GEYOCULIXLDCMW-UHFFFAOYAR
Properties
Chemical formula
C 6 H 8 N 2
Molar mass
108.144 g·mol−1
Appearance
white solid
Density
1.031 g/cm3
Melting point
102 to 104 °C (216 to 219 °F; 375 to 377 K )
Boiling point
252 °C (486 °F; 525 K ) Other sources: 256 to 258 °C (493 to 496 °F; 529 to 531 K )
Solubility in water
soluble in hot water
Acidity (p K a
0.80 (doubly protonated form; 20 °C, H2 O )
4.57 (conjugate acid; 20 °C, H2 O )[2]
Magnetic susceptibility (χ)
-71.98·10−6 cm 3
Hazards
GHS labelling
Pictograms
Signal word
Danger
Hazard statements
H301 , H312 , H317 , H319 , H332 , H341 , H351 , H410
Precautionary statements
P201 , P202 , P261 , P264 , P270 , P271 , P272 , P273 , P280 , P281 , P301+P310 , P302+P352 , P304+P312 , P304+P340 , P305+P351+P338 , P308+P313 , P312 , P321 , P322 , P330 , P333+P313 , P337+P313 , P363 , P391 , P405 , P501
NFPA 704
Flash point
156 °C (313 °F; 429 K )
Safety data sheet (SDS)
Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
o OPD ) is an organic compound with the formula C6 H 4 NH 2 2 aromatic diamine is an important precursor to many heterocyclic compounds . OPD is a white compound although samples appear darker owing to oxidation by air. It is isomeric with m p
Preparation [ edit ]
Commonly, 2-nitrochlorobenzene is treated with ammonia and the resulting 2-nitroaniline , whose nitro group is then reduced :[4]
ClC6 H 4 NO 2 3 2 NC 6 H 4 NO 2 4 Cl
H 2 NC 6 H 4 NO 2 2 2 NC 6 H 4 NH 2 2 O
In the laboratory, the reduction of the nitroaniline is effected with zinc powder in ethanol, followed by purification of the diamine as the hydrochloride salt . Darkened impure samples can be purified by treatment of its aqueous solution with sodium dithionite and activated carbon .[5]
Reactions and uses [ edit ]
o condenses with ketones and aldehydes to give rise to various valuable products. Its reactions with formic acids to produce benzimidazole .[6] benomyl and fuberidazole are made in this manner. Thiophanate-methyl is another herbicide produced from o-phenylenediamine.[4] potassium ethylxanthate gives 2-mercaptobenzimidazole .[7] nitrous acid , o benzotriazole , a corrosion inhibitor.[8]
Quinoxalinedione may be prepared by condensation of o dimethyl oxalate . Mercaptoimidazole are commonly used as antioxidants in rubber production, obtained by condensing xanthate esters . Condensation of substituted o diketones yields various pharmaceuticals .[9]
OPD is a ligand in coordination chemistry . Oxidation of metal-phenylenediamine complexes affords the diimine derivatives.[10] salicylaldehyde to give chelating Schiff base ligands .
With an LD 50 o para -isomerAnilines are typically handled as if they are carcinogenic . For many applications, OPD has been replaced by safer alternatives such as 3,3',5,5'-tetramethylbenzidine .[11]
References [ edit ]
^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics CRC Press . p. 5–89. ISBN 978-1498754286
^ "Hazardous Substances Data Bank (HSDB) : 2893 - PubChem" . PubChem.
^ a b Smiley, Robert A. (2000). "Phenylene- and Toluenediamines". Ullmann's Encyclopedia of Industrial Chemistry doi :10.1002/14356007.a19_405 . ISBN 3527306730
^ E. L. Martin (1939). "o Organic Syntheses . 19 doi :10.15227/orgsyn.019.0070 .
^ Wagner, E. C.; Millett, W. H. (1939). "Benzimidazole". Organic Syntheses . 19 doi :10.15227/orgsyn.019.0012 .
^ VanAllan, J. A.; Deacon, B. D. (1950). "2-Mercaptobenzimidazole". Organic Syntheses . 30 doi :10.15227/orgsyn.030.0056 .
^ Damschroder, R. E.; Peterson, W. D. (1940). "1,2,3-Benzotriazole". Organic Syntheses . 20 doi :10.15227/orgsyn.020.0016 .
^ See for example, Renault, J.; et al. (1981). "Heterocyclic quinones. Quinoxaline-5,6 and 5,8 diones, potential antitumoral agents". Eur. J. Med. Chem . 16
^ Broere, Daniël L. J.; Plessius, Raoul; Van Der Vlugt, Jarl Ivar (2015). "New Avenues for Ligand-Mediated Processes – Expanding Metal Reactivity by the Use of Redox-Active Catechol, o-Aminophenol and o-Phenylenediamine Ligands". Chemical Society Reviews . 44 19 ): 6886–6915. doi :10.1039/C5CS00161G . PMID 26148803 .
^ Deshpande SS (1996). Enzyme Immunoassays: From Concept to Product Development . New York: Chapman & Hall. p. 169. ISBN 978-0-412-05601-7
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=O-Phenylenediamine&oldid=1194340974 " C a t e g o r i e s : ● D i a m i n e s ● A n i l i n e s ● C h e l a t i n g a g e n t s H i d d e n c a t e g o r i e s : ● U s e m d y d a t e s f r o m J a n u a r y 2 0 2 3 ● A r t i c l e s w i t h o u t K E G G s o u r c e ● 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 F D A 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
● T h i s p a g e w a s l a s t e d i t e d o n 8 J a n u a r y 2 0 2 4 , a t 1 4 : 1 5 ( 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
