3,5-Dimethoxytoluene Chemical Properties

Melting point:

61-62 C

Boiling point:

244 °C (lit.)

Density 

1.039 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.522(lit.)

Flash point:

215 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Sparingly), Methanol (Sparingly)

form 

Liquid

Specific Gravity

1.039

color 

Clear colorless to yellow

Odor

Warm and sweet, nut-like, earthy-mossy odor

BRN 

2043558

LogP

2.897 (est)

CAS DataBase Reference

4179-19-5(CAS DataBase Reference)

NIST Chemistry Reference

3,5-Dimethoxytoluene(4179-19-5)

EPA Substance Registry System

3,5-Dimethoxytoluene (4179-19-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

Yes

HS Code 

29093090

MSDS

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

3,5-Dimethoxytoluene Usage And Synthesis

Chemical Properties

Clear colorless to yellow liquid

Uses

3,5-Dimethoxytoluene (DMT) may be used in the synthesis of 3,5-dimethoxybenzoic acid by oxidation and 2-methoxy-6-methyl-1,4-benzoquinone by catalytic oxidation with hydrogen peroxide (H₂O₂)/methyltrioxorhenium (CH₃ReO₃) in dimethyl carbonate (DMC).

Uses

3,5-Dimethoxytoluene has been suggested for use in perfume compositions as supporting note for Oakmoss and Vetiver, and as a novel note in Chypre, Fougere and Oriental fragrance types.

Definition

ChEBI: 3,5-dimethoxytoluene is a member of the class of toluenes that is toluene in which the hydrogens at positions 3 and 5 have been replaced by methoxy groups. It is the major scent compound of many rose varieties. It has a role as a fragrance and a plant metabolite. It is a member of toluenes and a member of methoxybenzenes.

Production Methods

3,5-Dimethoxytoluene can be produced from Orcinol in weak aqueous alkali with Dimethylsulfate at controlled temperature.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 6, p. 859, 1988
The Journal of Organic Chemistry, 70, p. 3275, 2005 DOI: 10.1021/jo050075r

General Description

3,5-Dimethoxytoluene (DMT) is a methoxylated phenolic derivative. It is reported to be one of the main constituent of the floral volatiles in different rose varieties. It has been biosynthesized from orcinol by two successive methylation catalyzed by O-methyltransferases (OMTs). The features of its aerobic oxidation with metal/bromide catalysts have been investigated.

Synthesis

A solution of dry orcinol (14.2 g,0.115 mole) in dry anhydrous acetone(150 ml) containing anhydrous potassium carbonate (45 g) is refluxed withdimethyl sulphate (23.6 ml，31.46 g, 0.25 mole) for 4 hr. The dimethylsulphate is added in small lots of 5 ml. After refluxing, the solution isfiltered and the inorganic residue washed with hot acetone (2 x 25 ml).The combined acetone solution is distilled and the residue macerated withcrushed ice. It is extracted with ether, the ether extract dried (anhydroussodium sulphate) and distilled. Yield 14.2 g (81.6%).B.p.102° (8 mm)

3,5-Dimethoxytoluene(4179-19-5)Related Product Information

• 3-Nitrotoluene
• Xylene
• 4-Methylanisole
• Dimethyl carbonate
• Metformin
• Dimethyldimethoxysilane
• 3,5-Dimethoxybenzonitrile
• 3-(3,4,5-TRIMETHOXYPHENYL)PROPIONIC ACID
• 4-Hydroxy-3,5-dimethoxycinnamic acid
• 3,5-Dimethoxybenzaldehyde
• 3,4,5-Trimethoxybenzyl alcohol
• 3,4,5-Trimethoxy benzoic acid
• 3,4,5-Trimethoxybenzaldehyde
• 3,4,5-Trimethoxyphenylacetic acid
• Colchicine
• 3,5-DIMETHOXYCINNAMIC ACID
• 3,5-DIMETHOXYBENZOYL CHLORIDE
• 3,4,5-Trimethoxyphenylacetonitrile