| Identification | More | [Name]
1,3,5-Trimethoxybenzene | [CAS]
621-23-8 | [Synonyms]
1,3,5-TRIMETHOXYBENZENE
3,5-DIMETHOXYANISOLE
PHLOROGLUCINOL TRIMETHYL ETHER
TRISMETHOXYBENZENE
1,3,5-trimethoxy-benzen
1,3,5-Trimethyoxybenzene
Benzene, 1,3,5-trimethoxy-
1,3,5-Trimethoxybenzene/Phloroglucinol trimethyl ether
O,O,O-1,3,5-trimethylresorcinol
1,3,5-TRIMETHOXYBENZENE, 99+%
1,3,5-TrimethoxybenzeneC9H12O3
1,3,5-TRIMETHOXYBENZENE pure
sym-Trimethoxybenzene
2,4,6-Trimethoxybenzene | [EINECS(EC#)]
210-673-4 | [Molecular Formula]
C9H12O3 | [MDL Number]
MFCD00008385 | [Molecular Weight]
168.19 | [MOL File]
621-23-8.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,F | [Risk Statements ]
R22:Harmful if swallowed.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing . | [RIDADR ]
1325 | [WGK Germany ]
3
| [RTECS ]
DC2810000
| [Hazard Note ]
Flammable Solid/Harmful | [TSCA ]
Yes | [HazardClass ]
4.1 | [PackingGroup ]
III | [HS Code ]
29093090 |
| Hazard Information | Back Directory | [Chemical Properties]
WHITE TO CREAM CRYSTALLINE POWDER | [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: A methoxybenzene carrying methoxy groups at positions 1, 3 and 5. It has been found to be a biomarker of flavonoid consumption in humans. | [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. |
| Spectrum Detail | Back Directory | [Spectrum Detail]
1,3,5-Trimethoxybenzene(621-23-8)MS
1,3,5-Trimethoxybenzene(621-23-8)1HNMR
1,3,5-Trimethoxybenzene(621-23-8)13CNMR
1,3,5-Trimethoxybenzene(621-23-8)IR1
1,3,5-Trimethoxybenzene(621-23-8)IR2
1,3,5-Trimethoxybenzene(621-23-8)Raman
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