1,3,5-Trimethoxybenzene Chemical Properties

Melting point:

50-53 °C (lit.)

Boiling point:

255 °C (lit.)

Density 

1,126g/cm

refractive index 

1,533

Flash point:

186 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

methanol: 0.1 g/mL, clear, colorless

form 

Crystalline Powder

color 

White to cream

Water Solubility 

insoluble

BRN 

1307993

InChIKey

LKUDPHPHKOZXCD-UHFFFAOYSA-N

LogP

1.605 (est)

CAS DataBase Reference

621-23-8(CAS DataBase Reference)

NIST Chemistry Reference

1,3,5-Trimethoxybenzene(621-23-8)

EPA Substance Registry System

1,3,5-Trimethoxybenzene (621-23-8)

Safety Information

Hazard Codes 

Xn,F

Risk Statements 

22-20/21/22

Safety Statements 

24/25-36-26

RIDADR 

1325

WGK Germany 

3

RTECS 

DC2810000

Hazard Note 

Flammable Solid/Harmful

TSCA 

Yes

HazardClass 

4.1

PackingGroup 

III

HS Code 

29093090

MSDS

• Language:English Provider:1,3,5-Trimethoxybenzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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1,3,5-Trimethoxybenzene Usage And Synthesis

Chemical Properties

white to cream crystalline powder. Insoluble in water.

Uses

1,3,5-Trimethoxybenzene is a major scent component of the Chinese rose odour. 1,3,5-Trimethoxybenzene is also a useful synthetic intermediate and is used to synthesize triaryl- and triheteroarylmethanes.

Definition

ChEBI: 1,3,5-trimethoxybenzene is a methoxybenzene carrying methoxy groups at positions 1, 3 and 5. It has been found to be a biomarker of flavonoid consumption in humans. It has a role as a biomarker and a human xenobiotic metabolite.

Reactions

1,3,5-Trimethoxybenzene is the main component of the Leaf Oil of Eugenia confusa and is also a commonly used chemical reagent in organic synthesis. It can be used in the following reactions:
(1) Friedel–Crafts reaction: In this reaction, 4,5-dichlorocyclopent-4-ene-1,3-dione reacts with 1,3,5-trimethoxybenzene to synthesize 5-(2,4,6-trimethoxyphenyl)-4-chlorocyclopent-4-ene-1,3-dione, and also generates the disubstituted product 3,4-bis-(2,4,6-trimethoxyphenyl)-2-chlorocyclopent-2-ene-1-one^[1].
(2) Addition reaction: Using trifluoromethanesulfonic acid as a catalyst, 1,3,5-trimethoxybenzene can react with maleimide to undergo a 1,4-addition reaction to synthesize 3-(2,4,6-trimethoxyphenyl) succinimide. It can also undergo a 1,4-addition reaction with acrylates^[2].
(3) Nitration reaction: 1,3,5-Trimethoxybenzene can be nitrated with N2O5 in an organic solvent to prepare 1,3,5-trimethoxy-2,4,6-trinitrobenzene. However, this method is not very practical due to the side reactions of oxidation and coupling^[3].

General Description

1,3,5-Trimethoxybenzene effectively cleaves p-methoxybenzyl protecting group on various alcohols and acids. It is the major scent compound present in Chinese rose species.

Synthesis

A solution of anhydrous phloroglucinol (6.3 g，0.05 mole) in dryacetone (100 ml) is refluxed for 6 hr under anhydrous conditions withdimethyl sulphate (15. 6 ml，20.8 g, 0.165 mole) in presence of ignitedpotassium carbonate (40 g).The mixture is filtered, and the inorganic saltswashed with hot acetone (2 × 20 ml). The combined acetone solution isdistilled and the residue macerated with crushed ice. It is extracted withether, the ether extracts washed with sodium hydroxide solution (5%),water，dried (sodium sulphate) and distilled. Yield 1,3,5-Trimethoxybenzene 6 g (71.4 %).M.p 52-3° (lit. m.p.52-53°).

Solubility in organics

Soluble in Methanol, Ether, Ethanol, Benzene.

Solubility in water

Insoluble

Purification Methods

Sublime it under vacuum. [Beilstein 6 III 635, 6 IV 7362.]

References

[1] V. A. EGOROV. Double Acylation Product in the SnCl4-promoted Reaction of 4,5-Dichlorocyclopent-4-en-1,3-dione with 1,3,5-Trimethoxybenzene[J]. Russian Journal of Organic Chemistry, 2023, 59 8: 1449-1452. DOI:10.1134/S1070428023080201.
[2] SEANGHAI HOR . Br?nsted acid-catalyzed 1,4-addition of 1,3,5-trimethoxybenzene to maleimides and acrylates[J]. Tetrahedron Letters, 2021, 74: Article 153100. DOI:10.1016/j.tetlet.2021.153100.
[3] A. J. BELLAMY. Nitration of 1,3,5-Trimethoxybenzene[J]. Journal of Chemical Research-s, 2002, 109 3 1: 412-413. DOI:10.3184/030823402103172662.

1,3,5-Trimethoxybenzene(621-23-8)Related Product Information

• Anisole
• Ethylbenzene
• PETROLEUM ETHER
• o-Anisaldehyde
• Trimethyl phosphite
• 3,4,5-Trimethoxyphenol
• (3-Methoxyphenyl)acetonitrile
• 4-Methoxyphenylacetic acid
• 2-Butoxyethanol
• m-Anisyl alcohol
• (Trifluoromethoxy)benzene
• Phloroglucinol
• p-Anisaldehyde
• 3-(METHOXYMETHOXY)BENZALDEHYDE
• Trimethyl borate
• 3,4,5-Trimethoxy benzoic acid
• Dimethyl ether
• Trimethylphloroglucinol