1,3,5-Trimethoxybenzene CAS 621-23-8

Introduction：Basic information about 1,3,5-Trimethoxybenzene CAS 621-23-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

1,3,5-Trimethoxybenzene Basic information

• Product Name: 1,3,5-Trimethoxybenzene
• Synonyms: 1,3,5-Trimethoxybenzene Vetec(TM) reagent grade, 98%;PHLOROGLUCINOL TRIMETHYL ETHER;TRISMETHOXYBENZENE;1,3,5-TriMethoxybenzene ReagentPlus(R), >=99%;1,3,5-Methoxybenzene;1,3,5-TriMetho;1,3,5-trimethoxy-benzen;1,3,5-Trimethyoxybenzene
• CAS: 621-23-8
• MF: C9H12O3
• MW: 168.19
• EINECS: 210-673-4
• Product Categories: Benzene derivates;Aromatic Ethers;ACTIVE PHARMACEUTICAL INGREDIENTS;621-23-8;API
• Mol File: 621-23-8.mol

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
• Fp: 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
• Cosmetics Ingredients Functions: SKIN CONDITIONING
• InChI: 1S/C9H12O3/c1-10-7-4-8(11-2)6-9(5-7)12-3/h4-6H,1-3H3
• InChIKey: LKUDPHPHKOZXCD-UHFFFAOYSA-N
• SMILES: COc1cc(OC)cc(OC)c1
• 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: TSCA listed
• HazardClass: 4.1
• PackingGroup: III
• HS Code: 29093090
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Acute Tox. 4 Oral

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 Preparation Products And Raw materials

• Raw materials: 3,5-Dibromoanisole-->1-Bromo-3,5-dimethoxybenzene-->Sodium Methoxide-->1,3,5-Tribromobenzene
• Preparation Products: P276-->dracorhodin-->2',4',6'-TRIMETHOXYACETOPHENONE-->1,2,3,6-TETRAHYDRO-1-METHYL-4-(2,4,6-TRIMETHOXYPHENYL)-PYRIDINE