2-Chloro-1,5-naphthyridine

2-Chloro-1,5-naphthyridine Property

Melting point:

109-111℃

Boiling point:

281℃

Density 

1.349

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

1.32±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C8H5ClN2/c9-8-4-3-6-7(11-8)2-1-5-10-6/h1-5H

InChIKey

JUYRQGHDOBBUEA-UHFFFAOYSA-N

SMILES

N1C2C(=NC=CC=2)C=CC=1Cl

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

2-Chloro-1,5-naphthyridine Chemical Properties,Usage,Production

Synthesis

(2) Synthesis of 2-chloro-1,5-diazanaphthalene. A 50 mL round bottom flask was charged with 1,5-diazanaphthalene N-oxide (98 mg, 1.355 mmol) and phosphorochloride (2 mL, 21.457 mmol). The reaction mixture was placed in an oil bath at 100 °C and the reaction was stirred for 8 hours. After completion of the reaction, the solvent was removed by rotary evaporator under reduced pressure. The residue was neutralized with saturated NaHCO3 solution (2 mL) and extracted with ethyl acetate (2 x 20 mL). The organic phases were combined, washed with saturated NaCl solution (2 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with 60% ethyl acetate/hexane as eluent to afford 2-chloro-1,5-diazanaphthalene (78 mg, 35% yield). Mass spectrum (ESI positive ion mode) m/z: calculated value C8H5ClN2 [M+H]+ 165.0, measured value 165.0. 1H NMR (300 MHz, CDCl3) δ ppm: 7.64 (d, J=8.77 Hz, 1H), 7.66-7.72 (m, J=4.38 Hz, 1H), 8.35 (t, J=8.77 Hz, 2H), 8.99 (dd, J=4.17,1.68Hz, 1H). 4-Chloro-1,5-diazaphthalene (86 mg, 39% yield) was also isolated. Mass spectrum (ESI positive ion mode) m/z: calculated value C8H5ClN2 [M+H]+ 165.0, measured value 165.0. 1H NMR (300 MHz, CDCl3) δ ppm: 7.75 (dd, J=8.55,4.17Hz, 1H), 7.79 (d, J=4.68Hz, 1H), 8.47 (dd, J=8.62,1.68Hz, 1H), 8.47 (dd, J=8.62,1.62Hz, 1.68Hz, 1H). 8.62,1.61Hz, 1H), 8.87 (d, J=4.68Hz, 1H), 9.11 (dd, J=4.09,1.61Hz, 1H).

References

[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4735 - 4751
[2] Patent: WO2009/155121, 2009, A2. Location in patent: Page/Page column 104