2,3-DIMETHYL-6-NITROANILINE
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2,3-DIMETHYL-6-NITROANILINE
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CAS No:
59146-96-2
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Formula:
C8H10N2O2
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Chemical Name:
2,3-DIMETHYL-6-NITROANILINE
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Synonyms:
6-NITRO-2,3-XYLIDINE;2,3-DIMETHYL-6-NITROANILINE;TIMTEC-BB SBB006536;2,3-DIMETHYL-6-NITROANILINE 98%;2,3-Dimethyl-6-nitroaniline,97%;2,3-Dimethyl-6-nitroaniline,6-Nitro-2,3-xylidine;(2,3-Dimethyl-6-nitrophenyl)amine;6-Nitro-2,3-xylidine, 2-Amino-3,4-dimethylnitrobenzene, 3-Amino-4-nitro-o-xylene
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CAS No:
Characteristics
71.8
2.4
Dark yellow to orange-brown Crystalline Powder
1.22g/cm3
117-120 °C(lit.)
334.3°C at 760 mmHg
156ºC
1.601
Safety Information
6.1
2811
3
20/21/22-36/37/38
26-36
Xn
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
H302
|Warning|H302 (97.67%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 43 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2,3-DIMETHYL-6-NITROANILINE Use and Manufacturing
To a solution of the mixture of nitroacetanilides (16.0 g, 1.0 equiv.) was added a 60percent H2SO4 solution (150 mL). The solution was heated at the reflux temp. for 1 h, then cooled to room temp. and treated with a 2N NaOH solution in ice water (100 mL). The resulting mixture was extracted with EtOAc (3.x.50 mL). The combined organic layers were washed with a saturated NaHCO3 solution (2.x.50 mL) and a saturated NaCl solution (2.x.50 mL), dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by column chromatography (10percent CH2Cl2/hex) to afford 2, 3-dimethyl-6-nitroaniline (5.5 g, 43percent), followed by 2, 3-dimethyl-4-nitroaniline (1.5 g, 12percent). 2, 3-Dimethyl-6-nitroaniline (5.5 g, 43percent): 1H NMR (CDCl3) δ2.05 (s, 3H), 2.20 (s, 3H), 6.15 (br s, 2H), 6.45 (d, J=8.7 Hz, 1H), 7.63 (d, J=9.0 Hz, 1H); 1H NMR (DMSO-d6) δ2.10 (s, 3H), 2.30 (s, 3H), 6.50 (d, J=8.7 Hz, 1H), 7.15 (br s, 2H), 7.75 (d, J=9.0 Hz, 1H). 2, 3-Dimethyl-4-nitroaniline: 1H NMR (CDCl3) δ2.10 (s, 3H), 2.45 (s, 3H), 4.05 (br s, 2H), 6.45 (d, J9.0 Hz, 1H), 7.65 (d, J=8.7 Hz, 1H); 1H NMR (DMSO-d6) δ2.00 (s, 3H), 2.35 (s, 3H), 6.12 (br s, 2H), 6.53 (d, J=9.0 Hz, 1H), 7.63 (d, J=9.0 Hz, 1H)
Computed Properties
Molecular Weight:166.18
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:166.074227566
Monoisotopic Mass:166.074227566
Topological Polar Surface Area:71.8
Heavy Atom Count:12
Complexity:178
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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