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138827

Sigma-Aldrich

1,3,5-Trimethoxybenzene

ReagentPlus®, ≥99%

Synonym(s):

Phloroglucinol trimethyl ether

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About This Item

Linear Formula:
C6H3(OCH3)3
CAS Number:
621-23-8
Molecular Weight:
168.19
Beilstein:
1307993
EC Number:
210-673-4
MDL number:
MFCD00008385
UNSPSC Code:
12352100
PubChem Substance ID:
24848368
NACRES:
NA.22

product line

ReagentPlus®

Assay

≥99%

form

solid

bp

255 °C (lit.)

mp

50-53 °C (lit.)

SMILES string

COc1cc(OC)cc(OC)c1

InChI

1S/C9H12O3/c1-10-7-4-8(11-2)6-9(5-7)12-3/h4-6H,1-3H3

InChI key

LKUDPHPHKOZXCD-UHFFFAOYSA-N

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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.

Application

1,3,5-Trimethoxybenzene was used to study the photodeoxygenation of 1,2-benzodiphenylene sulfoxide. It was employed as secondary standard in quantitative proton NMR spectroscopy of pharmaceuticals.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nicolas Kern et al.
The Journal of organic chemistry, 77(20), 9227-9235 (2012-09-26)
The p-methoxybenzyl protecting group (PMB) on various alcohols and an acid was efficiently and selectively cleaved by the action of a catalytic amount of silver(I) hexafluoroantimonate combined with 0.5 equiv of 1,3,5-trimethoxybenzene in dichloromethane at 40 °C.
Xichen Cai et al.
The journal of physical chemistry. A, 111(22), 4743-4747 (2007-05-08)
Bimolecular hole transfer quenching of the 1,3,5-trimethoxybenzene radical cation (TMB*+) in the excited state (TMB*+*) by hole quenchers (Q) such as biphenyl (Bp), naphthalene (Np), anisole (An), and benzene (Bz) with higher oxidation potentials than that of TMB was directly
Xichen Cai et al.
The journal of physical chemistry. A, 111(10), 1788-1791 (2007-02-14)
One-electron oxidation of alcohols such as methanol, ethanol, and 2-propanol by 1,3,5-trimethoxybenzene radical cation (TMB*+) in the excited state (TMB*+*) was observed during the two-color two-laser flash photolysis. TMB*+ was formed by the photoinduced bimolecular electron-transfer reaction from TMB to
Shuiqin Wu et al.
Plant physiology, 135(1), 95-102 (2004-05-04)
1,3,5-Trimethoxybenzene is a key component of the Chinese rose odor. This compound is synthesized in three successive methylation steps from phloroglucinol, the initial precursor. A novel, to our knowledge, phloroglucinol O-methyltransferase (POMT) characterized here methylates the first step to produce
Tao Fang et al.
Journal of the American Chemical Society, 134(17), 7545-7552 (2012-04-06)
The development of selectively protected monosaccharide building blocks that can reliably be glycosylated with a wide variety of acceptors is expected to make oligosaccharide synthesis a more routine operation. In particular, there is an urgent need for the development of
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