5-METHYLQUINOXALINE Chemical Properties

Melting point:

20-21 °C (lit.)

Boiling point:

120 °C/15 mmHg (lit.)

Density 

1.125 g/mL at 25 °C

FEMA 

3203 | 5-METHYLQUINOXALINE

refractive index 

n20/D 1.62(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

pka

1.40±0.30(Predicted)

color 

Light yellow to Yellow to Orange

Specific Gravity

1.112

Odor

at 0.10 % in dipropylene glycol. toasted roasted corn nutty coffee burnt

Odor Type

nutty

biological source

synthetic

JECFA Number

798

InChIKey

CQLOYHZZZCWHSG-UHFFFAOYSA-N

LogP

1.76

CAS DataBase Reference

13708-12-8(CAS DataBase Reference)

EPA Substance Registry System

Quinoxaline, 5-methyl- (13708-12-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-METHYLQUINOXALINE Usage And Synthesis

Description

5-Methylquinoxaline has a burnt, roasted, nutty, roasted com, coffee odor.

Chemical Properties

5-Methylquinoxaline has a burnt, roasted, nutty, roasted corn, coffee odor

Chemical Properties

Amber liquid

Occurrence

Reported found in coffee and roasted almonds

Uses

5-Methylquinoxaline was used in the synthesis of 1,12-diphenyl-5-methyl-1,12,12a,12b-tetrahydrobis[1,2,4]triazolo[4,3-a:3′,4′-c]quinoxaline bis-cycloadducts.

Definition

ChEBI: A quinoxaline derivative in which the quinoxaline (1,4-naphthyridine) skeleton is substituted at C-5 with a methyl group.

Taste threshold values

Taste characteristics at 2 ppm: nutty, roasted, peanut and pyrazine-like with yeasty, corn-chip nuance.

General Description

5-Methylquinoxaline has been identified as one of the key volatile aroma compounds in roasted almonds{170] and roasted coffee.

Synthesis

General method: 2,3-Diaminotoluene (2.0 mmol) was mixed with compound (CAS:131543-46-9, 2.0 mmol) and sulfated polyborate (10 wt%) was added. The reaction mixture was placed in an oil bath and the reaction was stirred at 100 °C. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched with deionized water. Subsequently, the mixture was filtered or extracted with ethyl acetate (EtOAc) to isolate the product. The crude product can be purified by ethanol recrystallization or by column chromatography using silica gel as stationary phase with ethyl acetate: petroleum ether (EtOAc:pet) as mobile phase. The final product is the known compound 5-methylquinoxaline, which was identified by determining its melting point and 1H NMR and 13C NMR spectra, and the resulting spectral data were confirmed by comparing them with literature values.

References

[1] Journal of Chemical Sciences, 2017, vol. 129, # 2, p. 141 - 148
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 357 - 364
[3] Organic Magnetic Resonance, 1980, vol. 14, # 4, p. 300 - 304
[4] Organic Process Research and Development, 2003, vol. 7, # 3, p. 318 - 323

5-METHYLQUINOXALINE(13708-12-8)Related Product Information

• 5-METHYLQUINOXALINE
• 6,7-DIMETHYL-2(1H)-QUINOXALINONE
• 2,3,6,7-TETRAMETHYLQUINOXALINE
• 2,6,7-Trichloro-3-(trifluoromethyl)quinoxaline
• 2,3-DIHYDROXY-6-METHYLQUINOXALINE,1,4-DIHYDRO-6-METHYLQUINOXALINE-2,3-DIONE,6-METHYLQUINOXALINE-2,3-DIOL
• 2,3,6-TRIMETHYLQUINOXALINE
• 6,7-Dichloro-3-(trifluoromethyl)quinoxalin-2(1H)-one
• 2,3-BIS(BROMOMETHYL)QUINOXALINE
• 2,3-DIMETHYL-QUINOXALINE-6-CARBOXYLIC ACID
• 6-METHYLQUINOXALINE
• 6,7-DIMETHYLQUINOXALINE
• 2,3-DIMETHYLQUINOXALINE
• 2,3-DICHLORO-6,7-DIMETHYLQUINOXALINE
• 3-HYDROXY-2-METHYLQUINOXALINE,2-Hydroxy-3-methylquinoxaline
• 2-Hydroxymethyl-3-methylquinoxaline 1,4-dioxide
• 2-(2-Hydroxyethoxycarbonyl)-3-methylquinoxaline 1,4-dioxide
• 2,3-DICHLORO-6-METHYLQUINOXALINE
• 3-Methylquinoxaline,2-METHYLQUINOXALINE