2,3-Dimethylanisole

2,3-Dimethylanisole Property

Melting point:

29 °C(lit.)

Boiling point:

195 °C(lit.)

Density 

0.984 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.52(lit.)

Flash point:

155 °F

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to lump

Specific Gravity

0.984

color 

White to Almost white

Water Solubility 

immiscible

BRN 

1859736

InChI

InChI=1S/C9H12O/c1-7-5-4-6-9(10-3)8(7)2/h4-6H,1-3H3

InChIKey

BLMBNEVGYRXFNA-UHFFFAOYSA-N

SMILES

C1(OC)=CC=CC(C)=C1C

LogP

3.211 (est)

CAS DataBase Reference

2944-49-2(CAS DataBase Reference)

NIST Chemistry Reference

2,3-Dimethylanisole(2944-49-2)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

HS Code 

29093090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

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

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

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

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

2,3-Dimethylanisole Chemical Properties,Usage,Production

Chemical Properties

clear light yellow liquid

Uses

2,3-Dimethylanisole is used as starting reagent in the synthesis of biphenyl-indanone A, a positive allosteric modulator of the metabotropic glutamate receptor subtype 2. It can be used to produce 2-methoxy-6-methyl-benzaldehyde by heating.

Synthesis

General procedure: 1-methoxy-2,3-dimethylbenzene was synthesized by alkylation of 2,3-dimethylphenol with dimethyl carbonate. The specific operation was as follows: 3 mmol of Mn2(CO)10, W(CO)6 or Co2(CO)8 catalyst, 100 mmol of 2,3-dimethylphenol, and 300 mmol of dimethyl carbonate were sequentially added to a 17 mL stainless steel high-pressure microreactor. After sealing the reactor, the reaction was heated at 180 °C for 1 hour. Upon completion of the reaction, the reactor was cooled to room temperature, opened and the reaction mixture was filtered through an alumina layer. The unreacted dimethyl carbonate was removed by distillation, and the residue was distilled under atmospheric or reduced pressure conditions or recrystallized using ethanol to obtain the target product 1-methoxy-2,3-dimethylbenzene. The yield of the reaction was 99% and the boiling point of the product was 95.8-96 °C (30 mmHg).13C NMR data (δC, ppm): 11.99 (CH3), 20.56 (CH3), 55.83 (OCH3), 110.02 (C6), 122.43 (C4), 124.78 (C2), 128.74 (C5). 137.70 (C3), 157.36 (C1). Elemental analysis results (measured values): C 79.29%, H 8.82%; calculated values for molecular formula C9H12O: C 79.37%, H 8.88%.

References

[1] Russian Journal of Organic Chemistry, 2015, vol. 51, # 3, p. 330 - 334
[2] Methylation of Phenol and Its Derivatives with Dimethyl Carbonate in the Presence of Mn2(CO)10, W(CO)6, and Co2(CO)8, 2015, vol. 51, # 3, p. 330 - 334,5