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621-23-8

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621-23-8 Usage

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.

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.

Purification Methods

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

Check Digit Verification of cas no

The CAS Registry Mumber 621-23-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 1 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 621-23:
(5*6)+(4*2)+(3*1)+(2*2)+(1*3)=48
48 % 10 = 8
So 621-23-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H12O3/c1-10-7-4-8(11-2)6-9(5-7)12-3/h4-6H,1-3H3

621-23-8 Well-known Company Product Price

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  • Alfa Aesar

  • (A13981)  1,3,5-Trimethoxybenzene, 99%   

  • 621-23-8

  • 10g

  • 179.0CNY

  • Detail
  • Alfa Aesar

  • (A13981)  1,3,5-Trimethoxybenzene, 99%   

  • 621-23-8

  • 50g

  • 687.0CNY

  • Detail
  • Alfa Aesar

  • (A13981)  1,3,5-Trimethoxybenzene, 99%   

  • 621-23-8

  • 250g

  • 2709.0CNY

  • Detail

621-23-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3,5-trimethoxybenzene

1.2 Other means of identification

Product number -
Other names Benzene,1,3,5-trimethoxy

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:621-23-8 SDS

621-23-8Synthetic route

1-chloro-3,5-dimethoxybenzene
7051-16-3

1-chloro-3,5-dimethoxybenzene

C4H12BO4(1+)*K(1+)

C4H12BO4(1+)*K(1+)

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In N,N-dimethyl-formamide at 100℃; Inert atmosphere;100%
methanol
67-56-1

methanol

1,3,5-trisbromobenzene
626-39-1

1,3,5-trisbromobenzene

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
Stage #1: methanol; 1,3,5-trisbromobenzene In toluene at 135℃; under 5320.36 Torr; for 0.75h;
Stage #2: With triethylamine In toluene at 165℃; under 8360.56 Torr; for 11h; Temperature;
99.5%
With sodium methylate; copper(l) chloride In N,N-dimethyl-formamide at 100 - 110℃; for 6h;90%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

methyl iodide
74-88-4

methyl iodide

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With potassium carbonate In acetone for 3h; Reflux;99%
With potassium carbonate In acetone for 6h; Reflux;80%
With methanol man troepfelt methylalkoholische Natriummethylatloesung hinzu;
2,4,6-trimethoxybenzoic acid
570-02-5

2,4,6-trimethoxybenzoic acid

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With palladium(II) trifluoroacetate; trifluoroacetic acid In dimethyl sulfoxide; N,N-dimethyl-formamide at 70℃; for 24h;99%
With [Rh(OH)(cod)]2; 1,3-bis-(diphenylphosphino)propane; water; sodium hydroxide In toluene at 120℃; for 18h; Inert atmosphere;85%
With sodium persulfate; ethanol at 60℃; for 18h; Temperature; Time; Sealed tube; Green chemistry;85%
With C40H42NO7PPdS In dichloromethane at 20℃; Schlenk technique;

A

B

2-(4'-(trifluoromethoxy)phenyl)-7-(trifluoromethoxy)naphthalene

2-(4'-(trifluoromethoxy)phenyl)-7-(trifluoromethoxy)naphthalene

Conditions
ConditionsYield
With trifluoroacetic acid In water at 80℃; for 0.5h; Diels-Alder Cycloaddition;A n/a
B 99%
1,3,5-trimethoxybenzene-2,4,6-d3
35564-11-5

1,3,5-trimethoxybenzene-2,4,6-d3

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate; water In chloroform at 80℃; for 24h; Sealed tube;98%
With acetic acid In hexane at 24.9℃; Kinetics; Thermodynamic data; Rate constant; other solvents; ΔH(activ.); -ΔS(activ.); ΔF(activ.).;
1,3,5-trisbromobenzene
626-39-1

1,3,5-trisbromobenzene

sodium methylate
124-41-4

sodium methylate

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With methanol; Methyl formate; copper(l) chloride at 115℃; for 2h; Autoclave; Green chemistry;98%
With copper(I) chloride In N,N-dimethyl-formamide at 130℃; for 6h;91%
1-(4'-fluorostyryl)-2,4,6-trimethoxybenzene

1-(4'-fluorostyryl)-2,4,6-trimethoxybenzene

A

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

B

2-(4'-fluorophenyl)-7-fluoronaphthalene

2-(4'-fluorophenyl)-7-fluoronaphthalene

Conditions
ConditionsYield
With trifluoroacetic acid In water at 80℃; for 0.5h; Diels-Alder Cycloaddition;A n/a
B 98%
(E)-1-(4'-iodostyryl)-2,4,6-trimethoxybenzene

(E)-1-(4'-iodostyryl)-2,4,6-trimethoxybenzene

A

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

B

2-(4'-iodophenyl)-7-iodonaphthalene

2-(4'-iodophenyl)-7-iodonaphthalene

Conditions
ConditionsYield
With trifluoroacetic acid In water at 80℃; for 0.5h; Diels-Alder Cycloaddition;A n/a
B 97%
2-trimethylsilyl-1,3,5-trimethoxybenzene
36086-05-2

2-trimethylsilyl-1,3,5-trimethoxybenzene

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With chloro-trimethyl-silane; water; potassium iodide In acetonitrile at 20℃; for 0.1h;96%
1,3,5-trimethoxy-2-(4-methyl-pent-1-enyl)benzene

1,3,5-trimethoxy-2-(4-methyl-pent-1-enyl)benzene

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With trifluoroacetic acid at 120℃;96%
3,5-dimethoxyphenol
500-99-2

3,5-dimethoxyphenol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With N,N'-dimethylimidazolium-2-carboxylate In acetonitrile at 160℃; for 1.33333h; Microwave irradiation; Green chemistry;96%
1,3,5-trisbromobenzene
626-39-1

1,3,5-trisbromobenzene

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With sodium; copper(I) iodide In N-methyl-acetamide; methanol95%
1,3,5-trimethoxy-2-(buta-1,3-dienyl)benzene
861389-87-9

1,3,5-trimethoxy-2-(buta-1,3-dienyl)benzene

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With trifluoroacetic acid at 120℃;95%
ethyl 3-(2,4,6-trimethoxy phenyl)acrylate
67827-53-6

ethyl 3-(2,4,6-trimethoxy phenyl)acrylate

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With trifluoroacetic acid at 120℃;95%
2,4,6-trimethoxybenzaldehyde
830-79-5

2,4,6-trimethoxybenzaldehyde

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
rhodium(III) chloride; 1,3-bis-(diphenylphosphino)propane In diethylene glycol dimethyl ether for 40h; Heating;94%
With hydrogen In cyclohexane at 165℃; under 15001.5 - 26252.6 Torr; for 4h; Solvent; Autoclave;90.9%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; air; triphenylphosphine In 1,4-dioxane for 48h; Heating;78%
With methanol; scandium tris(trifluoromethanesulfonate) Mechanism; other aromatic aldehydes;
1,3,5-trimethoxy-2-(pent-1-enyl)benzene

1,3,5-trimethoxy-2-(pent-1-enyl)benzene

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With trifluoroacetic acid at 120℃;94%
1-styryl-2,4,6-trimethoxybenzene

1-styryl-2,4,6-trimethoxybenzene

A

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

B

2-phenylnaphthalene
612-94-2

2-phenylnaphthalene

Conditions
ConditionsYield
With trifluoroacetic acid In water at 80℃; for 0.5h; Solvent; Temperature; Time; Diels-Alder Cycloaddition;A n/a
B 94%
(E)-1-(2'-methylstyryl)-2,4,6-trimethoxybenzene

(E)-1-(2'-methylstyryl)-2,4,6-trimethoxybenzene

A

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

B

2-(o-tolyl)-5-methylnaphthalene

2-(o-tolyl)-5-methylnaphthalene

Conditions
ConditionsYield
With trifluoroacetic acid In water at 80℃; for 0.5h; Diels-Alder Cycloaddition;A n/a
B 93%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

dimethyl sulfate
77-78-1

dimethyl sulfate

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With potassium carbonate In acetone92%
With potassium carbonate In acetone for 48h; Reflux;92%
With potassium carbonate In acetone for 0.0666667h; Heating; Microwave irradiation;91%
1,3,5-trimethoxy 2-vinyl benzene
40243-91-2

1,3,5-trimethoxy 2-vinyl benzene

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With trifluoroacetic acid at 120℃;92%
1-(4'-methylstyryl)-2,4,6-trimethoxybenzene

1-(4'-methylstyryl)-2,4,6-trimethoxybenzene

A

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

B

7-methyl-2-(4-methylphenyl)naphthalene
132725-78-1

7-methyl-2-(4-methylphenyl)naphthalene

Conditions
ConditionsYield
With trifluoroacetic acid In water at 80℃; for 0.5h; Diels-Alder Cycloaddition;A n/a
B 92%
2-(2',4',6'-trimethoxystyryl)naphthalene

2-(2',4',6'-trimethoxystyryl)naphthalene

A

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

B

3-(naphthalen-2'-yl)phenanthrene

3-(naphthalen-2'-yl)phenanthrene

Conditions
ConditionsYield
With trifluoroacetic acid In water at 80℃; for 0.5h; Diels-Alder Cycloaddition;A n/a
B 92%
(E)-1-(4'-bromostyryl)-2,4,6-trimethoxybenzene

(E)-1-(4'-bromostyryl)-2,4,6-trimethoxybenzene

A

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

B

2-(4'-bromophenyl)-7-bromonaphthalene
38251-86-4

2-(4'-bromophenyl)-7-bromonaphthalene

Conditions
ConditionsYield
With trifluoroacetic acid In water at 80℃; for 0.5h; Diels-Alder Cycloaddition;A n/a
B 92%
1,3,5-trimethoxy-2-(methylsulfinyl)benzene

1,3,5-trimethoxy-2-(methylsulfinyl)benzene

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With Octanethiol; trifluorormethanesulfonic acid In dichloromethane at 23℃; for 12h;91%
1-(2,4,6-trimethoxyphenyl)ethanone
832-58-6

1-(2,4,6-trimethoxyphenyl)ethanone

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With tin(IV) chloride In 1,2-dichloro-ethane Heating;90%
1,3,5-trimethoxy-2-(hex-1-enyl)benzene

1,3,5-trimethoxy-2-(hex-1-enyl)benzene

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With trifluoroacetic acid at 120℃;90%

A

1,2,3-trimethoxybenzene

1,2,3-trimethoxybenzene

B

2-(4'-(trifluoromethyl)phenyl)-7-(trifluoromethyl)naphthalene

2-(4'-(trifluoromethyl)phenyl)-7-(trifluoromethyl)naphthalene

Conditions
ConditionsYield
With trifluoroacetic acid In water at 80℃; for 0.5h; Diels-Alder Cycloaddition;A n/a
B 90%
1-(2'-chlorostyryl)-2,4,6-trimethoxybenzene

1-(2'-chlorostyryl)-2,4,6-trimethoxybenzene

A

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

B

2-(2'-chlorophenyl)-5-chloronaphthalene

2-(2'-chlorophenyl)-5-chloronaphthalene

Conditions
ConditionsYield
With trifluoroacetic acid In water at 80℃; for 0.5h; Diels-Alder Cycloaddition;A n/a
B 90%
1-(3',4'-difluorostyryl)-2,4,6-trimethoxybenzene

1-(3',4'-difluorostyryl)-2,4,6-trimethoxybenzene

A

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

B

2-(3',4'-difluorophenyl)-6,7-difluoronaphthalene

2-(3',4'-difluorophenyl)-6,7-difluoronaphthalene

Conditions
ConditionsYield
With trifluoroacetic acid In water at 80℃; for 0.5h; Diels-Alder Cycloaddition;A n/a
B 90%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

2-bromo-1,3,5-trimethoxybenzene
1131-40-4

2-bromo-1,3,5-trimethoxybenzene

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrachloromethane for 3h; Heating;100%
With ammonium metavanadate; oxygen; aluminium bromide In diethyl ether at 20℃; for 18h;99%
With perchloric acid; C34H45MoNO5; tetrabutylammomium bromide; dihydrogen peroxide In d7-N,N-dimethylformamide at 28℃; for 0.4h;99%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

2,4-dibromo-1,3,5-trimethoxybenzene
5876-90-4

2,4-dibromo-1,3,5-trimethoxybenzene

Conditions
ConditionsYield
With ammonium metavanadate; oxygen; aluminium bromide In 1,4-dioxane at 80℃; for 4h;100%
With hydrogen bromide; dimethyl sulfoxide In water; ethyl acetate at 60℃; for 2h;94%
With oxygen; lithium bromide; copper(ll) bromide In acetic acid at 60℃; under 760.051 Torr; regioselective reaction;93%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

bis(2,4,6-trimethoxyphenyl)nitrosonium nitrate

bis(2,4,6-trimethoxyphenyl)nitrosonium nitrate

Conditions
ConditionsYield
With dinitrogen tetraoxide; Nitrogen dioxide In dichloromethane Nitration;100%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

4-Chlorobutanoyl chloride
4635-59-0

4-Chlorobutanoyl chloride

1-(2,4,6-trimethoxybenzoyl)-1-chloropropane

1-(2,4,6-trimethoxybenzoyl)-1-chloropropane

Conditions
ConditionsYield
With hydrogenchloride; tin(IV) chloride In benzene100%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

9-benzyl-6-chloro-9H-purine
1928-76-3

9-benzyl-6-chloro-9H-purine

6-(1,3,5-trimethoxyphen-4-yl)-9-phenylmethyl-9H-purine
1241556-48-8

6-(1,3,5-trimethoxyphen-4-yl)-9-phenylmethyl-9H-purine

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; 1,1,1,3',3',3'-hexafluoro-propanol at 60℃; for 24h;100%
With aluminum (III) chloride In 1,2-dichloro-ethane for 0.5h; Reflux;95%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

tert-butyl ((ethylthio)(phenyl)methyl)carbamate
1323902-49-3

tert-butyl ((ethylthio)(phenyl)methyl)carbamate

tert-butyl N-[phenyl(2,4,6-trimethoxyphenyl)methyl]carbamate
1373935-52-4

tert-butyl N-[phenyl(2,4,6-trimethoxyphenyl)methyl]carbamate

Conditions
ConditionsYield
With N-iodo-succinimide In dichloromethane at -78℃; for 0.0833333h; Solvent; Temperature; Reagent/catalyst; Friedel-Crafts Alkylation; Sealed tube; Inert atmosphere; chemoselective reaction;100%
6,7-dimethoxy-1,4-dimethyl-1,4-epoxy-1,4-dihydronaphthalene

6,7-dimethoxy-1,4-dimethyl-1,4-epoxy-1,4-dihydronaphthalene

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

6,7-dimethoxy-1,4-dimethyl-2-(2’,4’,6’-trimethoxyphenyl)naphthalene

6,7-dimethoxy-1,4-dimethyl-2-(2’,4’,6’-trimethoxyphenyl)naphthalene

Conditions
ConditionsYield
With iron(III) chloride In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; regioselective reaction;100%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

1,4-dihydro-1,4-dimethyl-1,4-epoxynaphthalene
4705-93-5

1,4-dihydro-1,4-dimethyl-1,4-epoxynaphthalene

1,4-dimethyl-2-(2’,4’,6’-trimethoxyphenyl)naphthalene

1,4-dimethyl-2-(2’,4’,6’-trimethoxyphenyl)naphthalene

Conditions
ConditionsYield
With iron(III) chloride In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; regioselective reaction;100%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

dimethyl 2-(p-methylphenyl)cyclopropane-1,1-dicarboxylate
132145-64-3

dimethyl 2-(p-methylphenyl)cyclopropane-1,1-dicarboxylate

dimethyl 2-(2-(p-tolyl)-2-(2,4,6-trimethoxyphenyl)ethyl)malonate

dimethyl 2-(2-(p-tolyl)-2-(2,4,6-trimethoxyphenyl)ethyl)malonate

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 20℃; for 3h;100%
With ytterbium(III) triflate In 1,2-dichloro-ethane at 20 - 65℃; Catalytic behavior; Inert atmosphere;95%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

iodosylbenzene
536-80-1

iodosylbenzene

benzoic acid
65-85-0

benzoic acid

phenyl(2,4,6-trimethoxyphenyl)iodonium(III) benzoate

phenyl(2,4,6-trimethoxyphenyl)iodonium(III) benzoate

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at 0 - 20℃; for 1h; Inert atmosphere;100%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

dimethyl 2-(2-fluorophenyl)cyclopropane-1,1-dicarboxylate
1110700-49-6

dimethyl 2-(2-fluorophenyl)cyclopropane-1,1-dicarboxylate

dimethyl 2-(2-(2-fluorophenyl)-2-(2,4,6-trimethoxyphenyl)ethyl)malonate

dimethyl 2-(2-(2-fluorophenyl)-2-(2,4,6-trimethoxyphenyl)ethyl)malonate

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 40℃; for 4h;100%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

1-(4-phenyl-phenyl)-1-ethanol
3562-73-0

1-(4-phenyl-phenyl)-1-ethanol

4-(1-(2,4,6-trimethoxyphenyl)ethyl)-1,1'-biphenyl

4-(1-(2,4,6-trimethoxyphenyl)ethyl)-1,1'-biphenyl

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 100℃; for 4h; Sealed tube;100%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

1-(p-chlorophenyl)ethyl alcohol
3391-10-4

1-(p-chlorophenyl)ethyl alcohol

2-(1-(4-chlorophenyl)ethyl)-1,3,5-trimethoxybenzene

2-(1-(4-chlorophenyl)ethyl)-1,3,5-trimethoxybenzene

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 100℃; for 4h; Sealed tube;100%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

SS-morpholino 4-toluene(dithioperoxo)sulfonate
84655-87-8

SS-morpholino 4-toluene(dithioperoxo)sulfonate

S-(2,4,6-trimethoxyphenyl) 4-toluenethiosulfonate

S-(2,4,6-trimethoxyphenyl) 4-toluenethiosulfonate

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 16h; Inert atmosphere;100%
Multi-step reaction with 2 steps
1: trifluoroacetic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 1 h / 20 °C / Inert atmosphere
2: trifluoroacetic acid / dichloromethane / 16 h / 20 °C / Inert atmosphere
View Scheme
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

methyl vinyl ketone
78-94-4

methyl vinyl ketone

4-(2,4,6-trimethoxy-phenyl)-butan-2-one
53581-92-3

4-(2,4,6-trimethoxy-phenyl)-butan-2-one

Conditions
ConditionsYield
gold(III) chloride; silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃;99%
gold(III) chloride In acetonitrile at 20℃; for 24h;99.5%
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.0333333h; Michael Addition; Green chemistry;93%
With dichloro bis(acetonitrile) palladium(II); tin(ll) chloride In acetonitrile at 30℃; for 2h; Kinetics; Reagent/catalyst; Time; Solvent; Michael Addition; Inert atmosphere; Schlenk technique;92%
With boron trifluoride diethyl etherate
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

9-phenyl-fluoren-9-ol
25603-67-2

9-phenyl-fluoren-9-ol

9-phenyl-9-(2,4,6-trimethoxyphenyl)-9H-fluorene
115322-67-3

9-phenyl-9-(2,4,6-trimethoxyphenyl)-9H-fluorene

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 60℃; for 4h; Sealed tube;99%
With perchloric acid; nitromethane
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

1,3,5-tribromo-2,4,6-trimethoxybenzene
105404-90-8

1,3,5-tribromo-2,4,6-trimethoxybenzene

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile at 20℃; for 144h;99%
With bromine excess of reagent;80%
With bromine; iron(III) chloride In 1,2-dichloro-ethane Heating;70%
With bromine
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

benzaldehyde
100-52-7

benzaldehyde

2,2'-(phenylmethylene)bis(1,3,5-trimethoxybenzene)
54921-79-8

2,2'-(phenylmethylene)bis(1,3,5-trimethoxybenzene)

Conditions
ConditionsYield
With chloro-trimethyl-silane; bismuth(III) sulfate at 20℃; for 1h;99%
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.0833333h; Friedel-Crafts Alkylation;96%
With PEG-400 at 50 - 60℃; for 2h; Friedel-Crafts Alkylation; Green chemistry;92%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

acetyl chloride
75-36-5

acetyl chloride

1-(2,4,6-trimethoxyphenyl)ethanone
832-58-6

1-(2,4,6-trimethoxyphenyl)ethanone

Conditions
ConditionsYield
Stage #1: 1,2,3-trimethoxybenzene In dichloromethane at 0℃; for 0.166667h;
Stage #2: acetyl chloride With aluminum (III) chloride In dichloromethane for 2h; Friedel-Crafts Acylation;
99%
With zinc(II) chloride98%
With 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; for 5h; Friedel-Crafts Acylation; Inert atmosphere;92%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

2,3,4,6-tetra-O-benzyl-1-O-(trifluoroacetyl)-α-D-glucopyranose
125343-69-3

2,3,4,6-tetra-O-benzyl-1-O-(trifluoroacetyl)-α-D-glucopyranose

1-deoxy-1-(C-2',4',6'-trimethoxyphenyl) 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
82300-67-2

1-deoxy-1-(C-2',4',6'-trimethoxyphenyl) 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane for 0.0833333h; Ambient temperature;99%
With boron trifluoride diethyl etherate In dichloromethane for 0.0833333h; Product distribution; Ambient temperature; var. Lewis acids and aryl ethers;;99%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

3,5-dimethoxyphenol
500-99-2

3,5-dimethoxyphenol

Conditions
ConditionsYield
With orcinol; Acetobacterium dehalogenans veratrol-O-demethylase; Desulfitobacterium hafniense methyltransferase dhaf4611 In aq. buffer at 25℃; for 24h; pH=6.5; Inert atmosphere; Enzymatic reaction; regioselective reaction;99%
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; N-methylaniline In diethyl ether; xylene at 95℃; for 9h;85%
With 2-(diethylamino)ethanethiol hydrochloride; sodium t-butanolate In N,N-dimethyl-formamide for 2h; Heating;84%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

acetic anhydride
108-24-7

acetic anhydride

1-(2,4,6-trimethoxyphenyl)ethanone
832-58-6

1-(2,4,6-trimethoxyphenyl)ethanone

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In acetonitrile for 0.5h; Time; Friedel-Crafts Acylation; Inert atmosphere; Microwave irradiation; Heating; Green chemistry;99%
With trifluoroacetic acid at 20℃; for 1.5h; Friedel-Crafts Acylation;95%
With boron trifluoride diethyl etherate In ethyl acetate at 20℃; for 2h; Friedel-Crafts Acylation;93%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

(4-nitrophenyl)-bis-(2,4,6-trimethoxyphenyl)methane
54921-80-1

(4-nitrophenyl)-bis-(2,4,6-trimethoxyphenyl)methane

Conditions
ConditionsYield
With tin(IV) chloride; bis(1,5-cyclooctadiene)diiridium(I) dichloride at 90℃; for 1h;99%
With air; iodine In toluene at 60℃; for 24h; Friedel Crafts alkylation;93%
With [1,2,3,4,5-pentamethylcyclopentadiene Ir(SnCl3)2{SnCl2(H2O)2}] In 1,2-dichloro-ethane at 80℃; for 1h;90%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

2,3,5,6-tetramethyl-4-oxo-1-phenylthiocyclohexa-2,5-dienyl 2-chloroacetate
194720-38-2

2,3,5,6-tetramethyl-4-oxo-1-phenylthiocyclohexa-2,5-dienyl 2-chloroacetate

A

1,3,5-trimethoxy-2-(phenylsulfanyl)benzene
41280-62-0

1,3,5-trimethoxy-2-(phenylsulfanyl)benzene

B

4-hydroxy-2,3,5,6-tetramethylphenyl 2-chloroacetate

4-hydroxy-2,3,5,6-tetramethylphenyl 2-chloroacetate

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 0.166667h; Yields of byproduct given;A 99%
B n/a
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

2,3,5,6-tetramethyl-4-oxo-1-phenylthiocyclohexa-2,5-dienyl 2-chloroacetate
194720-38-2

2,3,5,6-tetramethyl-4-oxo-1-phenylthiocyclohexa-2,5-dienyl 2-chloroacetate

1,3,5-trimethoxy-2-(phenylsulfanyl)benzene
41280-62-0

1,3,5-trimethoxy-2-(phenylsulfanyl)benzene

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -30 - 20℃; for 0.166667h;99%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

1-(2,3,4,5,6-pentafluorophenylthio)-2,3,5,6-tetramethyl-4-oxocyclohexa-2,5-dienyl 2-chloroacetate
335642-28-9

1-(2,3,4,5,6-pentafluorophenylthio)-2,3,5,6-tetramethyl-4-oxocyclohexa-2,5-dienyl 2-chloroacetate

A

4-hydroxy-2,3,5,6-tetramethylphenyl 2-chloroacetate

4-hydroxy-2,3,5,6-tetramethylphenyl 2-chloroacetate

B

2-(2,3,4,5,6-pentafluorophenylthio)-1,3,5-trimethoxybenzene

2-(2,3,4,5,6-pentafluorophenylthio)-1,3,5-trimethoxybenzene

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -30 - 0℃; for 0.166667h;A n/a
B 99%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

1,4-dichlorophthalazine
4752-10-7

1,4-dichlorophthalazine

1-chloro-4-(2,4,6-trimethoxyphenyl)phthalazine

1-chloro-4-(2,4,6-trimethoxyphenyl)phthalazine

Conditions
ConditionsYield
With aluminium trichloride In 1,2-dichloro-ethane at 75℃; for 3.5h; Friedel-Crafts reaction;99%

621-23-8Relevant articles and documents

Bryant

, p. 1345 (1967)

Efficient 1H nuclear magnetic resonance method for improved quality control analyses of Ginkgo constituents

Li, Chia-Ying,Lin, Chun-Hua,Wu, Chia-Che,Lee, Kuo-Hsiung,Wu, Tian-Shung

, p. 3721 - 3725 (2004)

We developed an analytical method using 1H nuclear magnetic resonance (NMR) spectrometry to resolve analytical problems with Ginkgo. After a simple hydrolysis step, an NMR analysis of the terpene trilactone H-12 signals and the flavonol aglycone H-2′ (or H-2′/6′ for kaempferol) signals was performed. By comparing the solvent effects on the resolution of these signals, methanol-d4-benzene-d6 (65:35) was selected as the optimal 1H NMR solvent. The amounts of terpene lactones and flavonol aglycones in various commercial Ginkgo products and Ginkgo leaves were determined. This newly developed 1H NMR method enables the simultaneous analysis of terpene trilactones and flavonols and allows simple, rapid quantification of these compounds in pharmaceutical Ginkgo preparations.

Methylation with Dimethyl Carbonate/Dimethyl Sulfide Mixtures: An Integrated Process without Addition of Acid/Base and Formation of Residual Salts

Chan, Bun,Lui, Matthew Y.,Lui, Yuen Wai

, (2022/01/08)

Dimethyl sulfide, a major byproduct of the Kraft pulping process, was used as an inexpensive and sustainable catalyst/co-reagent (methyl donor) for various methylations with dimethyl carbonate (as both reagent and solvent), which afforded excellent yields of O-methylated phenols and benzoic acids, and mono-C-methylated arylacetonitriles. Furthermore, these products could be isolated using a remarkably straightforward workup and purification procedure, realized by dimethyl sulfide‘s neutral and distillable nature and the absence of residual salts. The likely mechanisms of these methylations were elucidated using experimental and theoretical methods, which revealed that the key step involves the generation of a highly reactive trimethylsulfonium methylcarbonate intermediate. The phenol methylation process represents a rare example of a Williamson-type reaction that occurs without the addition of a Br?nsted base.

Catalytic SNAr Hydroxylation and Alkoxylation of Aryl Fluorides

Kang, Qi-Kai,Li, Ke,Li, Yuntong,Lin, Yunzhi,Shi, Hang,Xu, Lun

supporting information, p. 20391 - 20399 (2021/08/13)

Nucleophilic aromatic substitution (SNAr) is a powerful strategy for incorporating a heteroatom into an aromatic ring by displacement of a leaving group with a nucleophile, but this method is limited to electron-deficient arenes. We have now established a reliable method for accessing phenols and phenyl alkyl ethers via catalytic SNAr reactions. The method is applicable to a broad array of electron-rich and neutral aryl fluorides, which are inert under classical SNAr conditions. Although the mechanism of SNAr reactions involving metal arene complexes is hypothesized to involve a stepwise pathway (addition followed by elimination), experimental data that support this hypothesis is still under exploration. Mechanistic studies and DFT calculations suggest either a stepwise or stepwise-like energy profile. Notably, we isolated a rhodium η5-cyclohexadienyl complex intermediate with an sp3-hybridized carbon bearing both a nucleophile and a leaving group.

Synthesis method of high-purity phloroglucinol compound

-

Paragraph 0018, (2021/06/09)

The invention discloses a one-step chemical catalytic synthesis method of high-purity phloroglucinol by taking 3,5-dichlorophenol as a starting material and taking strong base and a catalyst as auxiliary materials. Through the method, the phloroglucinol compound with high molar yield, high purity and low cost can be effectively synthesized.

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