6-Methylquinoxaline Chemical Properties

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 Information

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

MSDS

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6-Methylquinoxaline Usage And Synthesis

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

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