2-AMINOQUINOXALINE

2-AMINOQUINOXALINE Property

Melting point:

155-157℃

Boiling point:

297.6±20.0 °C(Predicted)

Density 

1.292

storage temp. 

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

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

3.70±0.28(Predicted)

form 

Solid

color 

Light Yellow

InChI

InChI=1S/C8H7N3/c9-8-5-10-6-3-1-2-4-7(6)11-8/h1-5H,(H2,9,11)

InChIKey

YOWAEZWWQFSEJD-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2)N=CC=1N

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/38-20/21/22

Safety Statements 

26-36/37-15

HS Code 

29339900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

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.

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

P321Specific treatment (see … on this label).

P330Rinse mouth.

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

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

2-AMINOQUINOXALINE Chemical Properties,Usage,Production

Chemical Properties

Yellow solid

Uses

2-Aminoquinoxaline is an aminopyrazine analog with potential use as chemiluminescence derivatization reagents for pyruvic acid.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 4955, 1951 DOI: 10.1021/ja01154a143

Synthesis

A mixture of 2-amino-3-chloroquinoxaline (495 mg, 2.75 mmol) and diphenylphosphine (0.48 mL, 2.76 mmol) was heated and reacted at 130 °C for 2 h under the catalytic influence of Pd(OAc)2 (0.8 mg, 0.13 mmol) to give a viscous blue-green product. The reaction mixture was extracted with diethyl ether and the soluble fraction was monitored by NMR in C6D6 to identify tetraphenyl diphenylphosphine (Ph2P-PPh2), diphenylchlorophosphine (Ph2PCl), 2-aminoquinoxaline (3a), and an unknown phosphorus compound (31P NMR signals: δ 14.9, 82.2, 12.8, 5.4 ppm, intensity ratio 84:12:2:2). The ether-insoluble hydrochloride fraction was treated with aqueous NaOH/Et2O to give 615 mg of blue-green powder. The ether phase was dried over Na2SO4 and the ether was removed under reduced pressure to give 220 mg of a brownish-yellow viscous substance with a low content of 2-aminoquinoxaline (about 20% relative intensity of 31P in addition to signals from tetraphenyldiphosphine, diphenyloxyphosphine and other phosphorus compounds). The mixture was purified by silica gel column chromatography (ethyl acetate/hexane, 95/5%) under aerobic conditions, and removal of the solvent afforded 180 mg (45% yield) of 2-aminoquinoxaline as a light yellow solid, with a melting point of 156 °C.1H NMR (CDCl3) δ: 5.03 (vbr, 2H, NH2), 7.45 (td, 3J = 8.4, 7, 4J = 1.2 Hz, 1H, H-6), 7.61 (td, 3J = 8.4, 7, 4J = 1.2 Hz, 1H, H-7), 7.67 (dd, 3J = 8.4, 4J = 1.2 Hz, 1H, H-8), 7.92 (dd, 3J = 8.4, 4J = 1.2 Hz, 1H, H-5), 8.35 (s, 1H, H-3); these data are in agreement with the literature [17]. literature [17].13C NMR (CDCl3) δ: 125.05 (CH-6), 125.88 (CH-8), 128.83 (CH-5), 137.43 (Cq-4a), 137.78 (CH-3), 130.29 (CH-7), 140.89 (Cq-8a), 151.97 (Cq-2). HRMS (ESI in MeOH): calculated value C8H7N3 [M+H]+ 146.0713; measured value: 146.0713.

References

[1] Polyhedron, 2013, vol. 50, # 1, p. 101 - 111