2-Methyl-1-naphthalenamine
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2-Methyl-1-naphthalenamine
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CAS No:
2246-44-8
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Formula:
C11H11N
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Chemical Name:
2-Methyl-1-naphthalenamine
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Synonyms:
1-Naphthalenamine,2-methyl-;1-Naphthylamine,2-methyl-;2-Methyl-1-naphthalenamine;2-Methyl-1-naphthylamine;1-Amino-2-methylnaphthalene;2-Methyl-1-aminonaphthalene
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CAS No:
Safety Information
3
22
26-36
QM3675000
Xn
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 4 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-Methyl-1-naphthalenamine Use and Manufacturing
General procedure: An oven-dried vial (35x12 mm) equipped with a PTFE-sealedxscrew cap was loaded with a magnetic stirrer bar, ((+/-)-binap)Ni[P(OPh)3]2*2PhCH3 (9) (39 mg, 25 mmol, 5mol-percent), (+/-)-binap (15 mg, 25 mmol, 5 mol-percent), and the corresponding aryl halide (0.50 mmol, 1.0 equiv.). The vial was then transferred into an argon-filled glovebox, where NaOtBu (216 mg, 2.20 mmol, 4.40 equiv.) and NH3 (0.5 M in 1, 4-dioxane, 3.0 mL, 1.5 mmol, 3.0 equiv.) were added. The reaction vial was capped, removed from the glovebox, and placed into a preheated oil bath at 120 C to stir for 18 h. On cooling, the reaction mixture was diluted with Et2O (15 mL), and washed with 1 M NaOH (10 mL) and H2O (210 mL). The organic layer was fused onto silica and purified via flash column chromatography (EtOAc/hexanes or EtOAc/MeOH) to give the corresponding aniline. 2-Methylnaphthalen-1-amine (19k) Following the general procedure using 1-bromo-2-methylnaphthalene (84 mL mg, 0.50 mmol), the desired compound 19k was obtained after purification via flash column chromatography(hexanes/EtOAc 90 : 10) as a dark orange oil (73 mg, 0.46 mmol, 93 percent). The spectral data were in accordance with those reported in the literature.[64] Rf 0.20 (hexanes/EtOAc 90 : 10). δH (CDCl3, 500 MHz) 7.85–7.80 (2H, m, 2Ar–H), 7.50–7.43 (2H, m, 2Ar–H), 7.33 (1H, d, J 8.3, Ar–H), 7.28 (1H, d, J 8.3, Ar–H), 4.11 (2H, br s, NH2), 2.38 (3H, s, CH3). δC (CDCl3, 125 MHz) 139.0 (Ar–C), 133.2 (Ar–C), 129.4 (Ar–CH), 128.6 (Ar–CH), 124.92 (Ar–CH), 124.87 (Ar–CH), 123.4 (Ar–C), 120.3 (Ar–CH), 118.3 (Ar–CH), 116.3 (Ar–CH), 17.8 (CH3).
Computed Properties
Molecular Weight:157.21
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:157.089149355
Monoisotopic Mass:157.089149355
Topological Polar Surface Area:26
Heavy Atom Count:12
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
