1-AMINO-2-METHYLNAPHTHALENE Chemical Properties

Melting point:

28-31 °C(lit.)

Boiling point:

165 °C

Density 

1.67

refractive index 

n20/D 1.670

Flash point:

28 °C

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

powder to lump to clear liquid

pka

4.78±0.10(Predicted)

color 

White or Colorless to Brown

BRN 

2042530

Stability:

Light Sensitive

InChI

InChI=1S/C11H11N/c1-8-6-7-9-4-2-3-5-10(9)11(8)12/h2-7H,12H2,1H3

InChIKey

JMBLSGAXSMOKPN-UHFFFAOYSA-N

SMILES

C1(N)=C2C(C=CC=C2)=CC=C1C

CAS DataBase Reference

2246-44-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

26-36

WGK Germany 

3

RTECS 

QM3675000

HS Code 

2921490090

MSDS

• Language:English Provider:SigmaAldrich

1-AMINO-2-METHYLNAPHTHALENE Usage And Synthesis

Uses

1-Amino-2-Methylnaphthalene is used in preparation of (Piperazinyl)pyridopyrimidinone derivatives as KRAS G12C inhibitor for treatment of KRAS G12C-related diseases.

Synthesis

General procedure for the synthesis of 1-bromo-2-methylnaphthalene from 1-bromo-2-methylnaphthalene: In an oven-dried vial (35x12 mm) fitted with a PTFE-sealed screw cap, a magnetic stir bar, ((+/-)-binap)Ni[P(OPh)3]2-2PhCH3 (39 mg, 25 μmol, 5 mol%), (+/-)- binap (15 mg, 25 μmol, 5 mol%) and the corresponding aryl halide (0.50 mmol, 1.0 equiv). Subsequently, the vial was transferred to an argon-filled glove box and NaOtBu (216 mg, 2.20 mmol, 4.40 eq.) and NH3 (0.5 M solution of 1,4-dioxane, 3.0 mL, 1.5 mmol, 3.0 eq.) were added sequentially. After sealing the reaction vial, it was removed from the glove box and placed in an oil bath preheated to 120 °C with stirring for 18 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was diluted with Et2O (15 mL) and washed sequentially with 1 M NaOH (10 mL) and H2O (10 mL). The organic layer was adsorbed on silica gel and purified by fast column chromatography (eluent: EtOAc/hexane or EtOAc/MeOH) to obtain the target product aniline analogs. Specifically for the synthesis of 2-methylnaphthalen-1-amine (19k), 1-bromo-2-methylnaphthalene (84 μL, 0.50 mmol) was used as the starting material according to the general method described above and purified by fast column chromatography (eluent: Hexane/EtOAc 90:10) to afford the dark orange oily target compound 19k (73 mg, 0.46 mmol, 93% yield). The spectral data were in agreement with those reported in the literature [64]: Rf 0.20 (hexane/EtOAc 90:10); 1H NMR (CDCl3, 500 MHz) δ 7.85-7.80 (2H, m, 2Ar-H), 7.50-7.43 (2H, m, 2Ar-H), 7.33 (1H, d, J = 8.3 Hz, Ar-H), 7.28 (1H, d, J = 8.3 Hz, Ar-H), 4.11 (2H, br s, NH2), 2.38 (3H, s, CH3); 13C NMR (CDCl3, 125 MHz) δ 139.0 (Ar-C), 133.2 (Ar-C), 129.4 (Ar-CH), 128.6 (Ar-CH), 124.92 (Ar-CH), 124.92 (Ar-CH), 128.6 (Ar-CH), 124.92 (Ar-CH), 128.6 (Ar-CH), 128.6 (Ar-CH), 128.6 (Ar-CH), 124.9 (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).

References

[1] Australian Journal of Chemistry, 2015, vol. 68, # 12, p. 1842 - 1853
[2] Journal of Organic Chemistry, 2010, vol. 75, # 14, p. 4887 - 4890

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