6-Methylquinoxaline

6-Methylquinoxaline Property

Melting point:

218.5°C

Boiling point:

244-245°C

Density 

1.1164

refractive index 

1.6190

Flash point:

244-245°C

storage temp. 

Sealed in dry,Room Temperature

pka

1.40±0.30(Predicted)

Appearance

Light yellow to brown Liquid

BRN 

113371

InChI

InChI=1S/C9H8N2/c1-7-2-3-8-9(6-7)11-5-4-10-8/h2-6H,1H3

InChIKey

OSRARURJYPOUOV-UHFFFAOYSA-N

SMILES

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

LogP

1.872 (est)

CAS DataBase Reference

6344-72-5(CAS DataBase Reference)

NIST Chemistry Reference

Quinoxaline, 6-methyl-(6344-72-5)

Safety

Hazard Codes 

Xn,Xi,C,F

Risk Statements 

22-36/37/38-34-11

Safety Statements 

23-26-36/37/39-45-16

HazardClass 

IRRITANT

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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).

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

P337+P313IF eye irritation persists: Get medical advice/attention.

6-Methylquinoxaline Chemical Properties,Usage,Production

Uses

6-Methylquinoxaline (CAS# 6344-72-5) can be used as a conductive roller for electrophotographic apparatus. It has also be known for its sequential synthesis, olfactory properties, and biological activity.

Definition

ChEBI: 6-Methylquinoxaline is a quinoxaline derivative.

Synthesis

Synthesis of 6-methylquinoxaline: 3,4-diaminotoluene (Aldrich, 100 g, 0.82 mol) was dissolved in 600 mL of hot water (70-75°C) and quickly added to a slurry of glyoxal-sodium bisulfite adduct (Aldrich, 239.5 g, 0.9 mol, 1.1 equiv) in 400 mL of water at 60°C. The reaction mixture was heated at 60 °C for 1 h and then 5 g (0.02 mol) of the glyoxal adduct was added retrospectively. After cooling to room temperature, it was filtered through a paper filter. The filtrate was neutralized to pH 7.5-7.8 with 5 M NaOH aqueous solution and subsequently extracted with ether (4 x 400 mL). The combined organic phases were dried over anhydrous Na2SO4 and concentrated by rotary evaporation to give 92 g of brown oil. This crude product was purified by vacuum distillation (boiling point 100-102 °C, 10 mmHg; literature value: 86 °C, 1 mmHg) to give 89 g (75% yield) of light yellow oily target product.

References

[1] Patent: US2005/282820, 2005, A1. Location in patent: Page/Page column 17-18
[2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 7, p. 803 - 810
[3] Journal of the American Chemical Society, 1947, vol. 69, p. 795,796