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1,3,5-Trimethoxybenzene

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CAS:621-23-8
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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 Structure
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 FunctionsSKIN CONDITIONING
InChIKeyLKUDPHPHKOZXCD-UHFFFAOYSA-N
LogP1.605 (est)
CAS DataBase Reference621-23-8(CAS DataBase Reference)
NIST Chemistry Reference1,3,5-Trimethoxybenzene(621-23-8)
EPA Substance Registry System1,3,5-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
MSDS Information
ProviderLanguage
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SigmaAldrich English
ACROS English
ALFA English
1,3,5-Trimethoxybenzene Usage And Synthesis
Chemical Propertieswhite to cream crystalline powder. Insoluble in water.
Uses1,3,5-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.
DefinitionChEBI: 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.
Reactions1,3,5-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 Description1,3,5-Trimethoxybenzene effectively cleaves p-methoxybenzyl protecting group on various alcohols and acids. It is the major scent compound present in Chinese rose species.
SynthesisA 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°).
1,3,5-Trimethoxybenzene synthesis
Solubility in organicsSoluble in Methanol, Ether, Ethanol, Benzene.
Solubility in waterInsoluble
Purification MethodsSublime 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.
Tag: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

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