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151-10-0

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151-10-0 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 151-10-0 differently. You can refer to the following data:
1. clear colorless to slightly brown liquid
2. m-Dimethoxybenzene has a very powerful sweet-earthy, intensely, nut-like aroma.

Occurrence

Reported found in Gruyere de Comte, blue cheeses, filberts and cognac

Uses

Different sources of media describe the Uses of 151-10-0 differently. You can refer to the following data:
1. Organic intermediate, flavoring.
2. 1,3-Dimethoxybenzene is used for the preparation of oxathiane spiroketal donors. It is also used for the formation of pi- and O-ylidic complexes with dichlorocarbene. Further, it acts as a flavoring agent.

Preparation

From resorcinol by methylation using dimethyl sulfate and alka

Taste threshold values

Chemical, medicinal, spice, cooling root beer-like.

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 991, 1990 DOI: 10.1021/jo00290a033

General Description

1,3-Dimethoxybenzene can be used as a flavoring agent in the food industry. It is reported to be found in the volatiles of port wine and Roquefort cheese.

Purification Methods

Extract it with aqueous NaOH, and water, then dry it. Fractionally distil it from BaO or Na. [Beilstein 6 IV 5663.]

Check Digit Verification of cas no

The CAS Registry Mumber 151-10-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 1 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 151-10:
(5*1)+(4*5)+(3*1)+(2*1)+(1*0)=30
30 % 10 = 0
So 151-10-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O2/c1-9-7-4-3-5-8(6-7)10-2/h3-6H,1-2H3

151-10-0 Well-known Company Product Price

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  • Alfa Aesar

  • (A13380)  1,3-Dimethoxybenzene, 98%   

  • 151-10-0

  • 100g

  • 123.0CNY

  • Detail
  • Alfa Aesar

  • (A13380)  1,3-Dimethoxybenzene, 98%   

  • 151-10-0

  • 500g

  • 407.0CNY

  • Detail

151-10-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3-Dimethoxybenzene

1.2 Other means of identification

Product number -
Other names resorcinol dimethyl ether

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:151-10-0 SDS

151-10-0Synthetic route

2-6-dimethoxybenzoic acid
1466-76-8

2-6-dimethoxybenzoic acid

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With trifluoroacetic acid; palladium(II) trifluoroacetate In dimethyl sulfoxide; N,N-dimethyl-formamide at 70℃; for 24h;100%
With palladium(II) trifluoroacetate; trifluoroacetic acid In dimethyl sulfoxide; N,N-dimethyl-formamide at 70℃; for 24h;100%
With copper(I) oxide; N,N,N,N,-tetramethylethylenediamine In 1-methyl-pyrrolidin-2-one at 140℃; for 2h; Inert atmosphere;92%
C16H27NO5Si

C16H27NO5Si

A

C16H36O7Si2N2

C16H36O7Si2N2

B

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; for 7h; UV-irradiation;A 100%
B n/a
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

sodium methylate
124-41-4

sodium methylate

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With Methyl formate; copper(l) chloride In methanol at 110℃; for 2h; Autoclave;98%
dimethyl sulfate
77-78-1

dimethyl sulfate

recorcinol
108-46-3

recorcinol

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With potassium carbonate In acetone at 65℃; for 25h;96%
With potassium carbonate In acetone for 4h; Reflux;94%
With potassium carbonate In acetone for 0.0666667h; Heating; Microwave irradiation;91%
2,4 dimethoxybenzoic acid
91-52-1

2,4 dimethoxybenzoic acid

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With silver carbonate In dimethyl sulfoxide at 140℃; for 16h;96%
With silver(I) acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 16h; Inert atmosphere;89%
With palladium diacetate; dimethyl sulfoxide; silver carbonate; copper(ll) bromide In tetrahydrofuran at 110℃; for 36h;15%
(2,6-dimethoxyphenyl)boronic acid
23112-96-1

(2,6-dimethoxyphenyl)boronic acid

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With n-butyl acrylate; SiO2-Rh(0) In water; toluene at 100℃; for 48h;95%
With acetic acid In 1,4-dioxane at 100℃; for 5h; Enzymatic reaction;91%
With acetic acid at 130℃; for 3h; Green chemistry;88%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

methyl iodide
74-88-4

methyl iodide

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
Stage #1: 3-methoxyphenyl bromide With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 1.5h;
Stage #2: methyl iodide With cetyltrimethylammonim bromide In 1,4-dioxane; water at 100℃; for 1h;
94%
2,4-dimethoxyphenylboronic acid
133730-34-4

2,4-dimethoxyphenylboronic acid

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With acetic acid In 1,4-dioxane at 100℃; for 5h; Enzymatic reaction;93%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

A

2,6-dimethoxytoluene
5673-07-4

2,6-dimethoxytoluene

B

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With sodium In toluene; butan-1-ol at 111℃; for 3.5h;A 8%
B 92%
2,4-dimethoxy-1-(4'-methoxystyryl)benzene

2,4-dimethoxy-1-(4'-methoxystyryl)benzene

A

2-(4'-methoxyphenyl)-7-methoxynaphthalene
59115-48-9

2-(4'-methoxyphenyl)-7-methoxynaphthalene

B

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With trifluoroacetic acid In water at 80℃; for 0.5h; Diels-Alder Cycloaddition;A 92%
B n/a
1-bromo-3,5-dimethoxybenzene
20469-65-2

1-bromo-3,5-dimethoxybenzene

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With isopropyl alcohol for 10h; Schlenk technique; Inert atmosphere; Irradiation; Heating;92%
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 2h;86%
With 1,4-dioxane; 1,10-Phenanthroline; sodium hydride In mineral oil at 140℃; for 22h; Schlenk technique; Inert atmosphere;65%
With N-ethyl-N,N-diisopropylamine In acetonitrile for 16h; Irradiation;86 %Spectr.
With 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole; C41H39IrN6 In N,N-dimethyl-formamide at 45℃; for 24h; Reagent/catalyst; Irradiation; Glovebox;95 %Chromat.
trifluoromethanesulfonic acid 2,6-dimethoxyphenyl ester
60319-07-5

trifluoromethanesulfonic acid 2,6-dimethoxyphenyl ester

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With hydrogen; triethylamine; palladium on activated charcoal In methanol under 3361.5 Torr; other solvent, other temp., other reagents, other catalysts;90%
With hydrogen; palladium on activated charcoal In methanol under 3361.5 Torr; Product distribution; other catalysts, other solvent, other temp., other reagent;90%
With tetra-n-butyltin(IV); bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; lithium chloride86%
With 2,6-di-tert-butyl-4-methyl-phenol; tetra-n-butyltin(IV); bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; lithium chloride In N,N-dimethyl-formamide at 120℃;86%
recorcinol
108-46-3

recorcinol

methyl iodide
74-88-4

methyl iodide

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 48h;90%
With potassium carbonate In acetone at 20℃; Inert atmosphere;87.69%
With potassium carbonate In N,N-dimethyl-formamide for 3h;
1-iodo-2,4-dimethoxybenzene
20469-63-0

1-iodo-2,4-dimethoxybenzene

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With tetrahydrofuran; 1,10-Phenanthroline; potassium tert-butylate at 70℃; for 24h; Schlenk technique; Inert atmosphere;90%
With potassium tert-butylate at 80℃; for 12h; Inert atmosphere; Schlenk technique;87%
Stage #1: 1-iodo-2,4-dimethoxybenzene With chloro-trimethyl-silane; ethylene dibromide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium chloride; cobalt(II) chloride; zinc In tetrahydrofuran at 20℃; for 7h; Inert atmosphere;
Stage #2: With iodine In tetrahydrofuran for 0.5h;
7 %Chromat.
3,5-dimethoxybenzenediazonium o-benzenedisulfonimide

3,5-dimethoxybenzenediazonium o-benzenedisulfonimide

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With dihydrogen peroxide In tetrahydrofuran for 1h; Heating;89%
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

recorcinol
108-46-3

recorcinol

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With layered double hydroxide - supported L-methionine at 180℃; for 6h; Autoclave; chemoselective reaction;89%
1-styryl-2,4-dimethoxybenzene

1-styryl-2,4-dimethoxybenzene

A

2-phenylnaphthalene
612-94-2

2-phenylnaphthalene

B

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With trifluoroacetic acid In water at 80℃; for 0.5h; Diels-Alder Cycloaddition;A 87%
B n/a
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With potassium In tetrahydrofuran for 24h; Ambient temperature;86%
With ethanol; sodium
With water 1) THF, RT, 24h; Yield given. Multistep reaction;
With 2-iodo-propane; potassium 1.) THF, rt, 24 h; 2.) 0 deg C, 4 h; Yield given. Multistep reaction;
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

A

1,3-dimethoxy-2-hydroxy-benzene
91-10-1

1,3-dimethoxy-2-hydroxy-benzene

B

2,3-dimethoxyphenol
5150-42-5

2,3-dimethoxyphenol

C

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With potassium In tetrahydrofuran for 24h; Ambient temperature;A n/a
B n/a
C 85%
methanol
67-56-1

methanol

3-methoxycyclohex-2-en-1-one
16807-60-6

3-methoxycyclohex-2-en-1-one

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With iodine at 60℃; for 2h;85%
Trimethyl borate
121-43-7

Trimethyl borate

potassium 4-methoxybenzoate
52509-81-6

potassium 4-methoxybenzoate

A

methyl 4-methoxybenzoate
121-98-2

methyl 4-methoxybenzoate

B

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With oxygen; copper diacetate; silver carbonate In N,N-dimethyl-formamide at 150℃; under 760.051 Torr; for 36h;A 8%
B 83%
Trimethyl borate
121-43-7

Trimethyl borate

potassium 4-methoxybenzoate
52509-81-6

potassium 4-methoxybenzoate

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With oxygen; copper diacetate; silver carbonate In N,N-dimethyl-formamide at 140℃; under 760.051 Torr; for 36h;82%
With silver carbonate; copper(ll) bromide In N,N-dimethyl-formamide at 170℃; for 0.666667h; Microwave irradiation;41%
2,4 dimethoxybenzoic acid
91-52-1

2,4 dimethoxybenzoic acid

Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

A

2-(3',5'-dimethoxyphenyl)benzothiophene
133617-46-6

2-(3',5'-dimethoxyphenyl)benzothiophene

B

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique;A 82%
B 16%
1-Bromo-2,4-dimethoxybenzene
17715-69-4

1-Bromo-2,4-dimethoxybenzene

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
Stage #1: 1-Bromo-2,4-dimethoxybenzene With palladium dichloride In water at 20℃; for 0.0333333h;
Stage #2: With 1,1,3,3-Tetramethyldisiloxane for 0.133333h;
81%
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine; trifluoroacetic acid In toluene at 70℃; for 2h;53%
With 2,2'-azobis(isobutyronitrile); hypophosphorous acid; sodium hydrogencarbonate In ethanol for 5h; Heating;9%
With N-ethyl-N,N-diisopropylamine In acetonitrile for 16h; Irradiation;89 %Spectr.
2-iodo-1,3-dimethoxybenzene
16932-44-8

2-iodo-1,3-dimethoxybenzene

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With 2-(2-methoxyethoxy)ethyl alcohol; oxygen; sodium hydride In 1,4-dioxane at 20℃; for 24h; Schlenk technique; chemoselective reaction;81%
2,4-Dimethoxyaniline
2735-04-8

2,4-Dimethoxyaniline

A

2,4-dimethoxybenzenediazonium tetrafluoroborate
7438-18-8

2,4-dimethoxybenzenediazonium tetrafluoroborate

B

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With tetrafluoroboric acid; sodium nitrite In waterA 79%
B n/a
N-acetylindole
576-15-8

N-acetylindole

2,4 dimethoxybenzoic acid
91-52-1

2,4 dimethoxybenzoic acid

A

C18H17NO3
1224728-89-5

C18H17NO3

B

2-(2',4'-dimethoxyphenyl)-N-acetylindole
1235306-33-8

2-(2',4'-dimethoxyphenyl)-N-acetylindole

C

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With 1-oxothiolane; palladium(II) trifluoroacetate; propionic acid; silver carbonate In 1,4-dioxane at 80℃; for 24h; Inert atmosphere;A n/a
B 78%
C 84 %Chromat.
3,5-dimethoxyphenyl pivalate
1283160-96-2

3,5-dimethoxyphenyl pivalate

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); (dimethoxy)methylsilane; tricyclohexylphosphine In toluene at 80℃; for 12h; Inert atmosphere;78%
With bis(1,5-cyclooctadiene)nickel (0); sodium formate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 140℃; for 24h; Inert atmosphere; Schlenk technique;72%
3,5-dimethoxy-benzonitrile
19179-31-8

3,5-dimethoxy-benzonitrile

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tri-n-butyl phosphite; chlorotriisopropylsilane In ethylcyclohexane at 130℃; for 15h; Inert atmosphere;76%
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

1-Bromo-2,4-dimethoxybenzene
17715-69-4

1-Bromo-2,4-dimethoxybenzene

Conditions
ConditionsYield
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 4.5h; Heating;100%
With N-Bromosuccinimide100%
With N-Bromosuccinimide; silica gel In tetrachloromethane at 30℃; for 2h;99%
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

1,3-dichloro-4,6-dimethoxybenzene
50375-04-7

1,3-dichloro-4,6-dimethoxybenzene

Conditions
ConditionsYield
With sulfuryl dichloride In dichloromethane at 0 - 20℃;100%
With N-chloro-succinimide; diphenyldisulfane In acetonitrile at 20℃;97%
With sulfuryl dichloride In dichloromethane at 0 - 20℃; for 8h; Chlorination;94%
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

4,6-dibromo-1,3-dimethoxybenzene
24988-36-1

4,6-dibromo-1,3-dimethoxybenzene

Conditions
ConditionsYield
With oxygen; lithium bromide; copper(ll) bromide In acetic acid at 60℃; under 760.051 Torr; regioselective reaction;100%
With N-Bromosuccinimide; diphenyldisulfane In acetonitrile at 20℃; for 1h; Reagent/catalyst;100%
With bromine In dichloromethane Product distribution; other substrates, amounts of reagent;99%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

4,4'-((4-nitrophenyl)methylene)bis(1,3-dimethoxybenzene)
143959-23-3

4,4'-((4-nitrophenyl)methylene)bis(1,3-dimethoxybenzene)

Conditions
ConditionsYield
With o-benzenedisulfonimide at 20℃; for 2h; Friedel Crafts alkylation; neat (no solvent);100%
With 1-methyl-3-(propyl-3-sulfonyl)imidazolium trifluoromethanesulfonate In neat (no solvent) at 40℃; for 6h; Friedel-Crafts Alkylation; Green chemistry;87%
With sulfuric acid80%
With 3-methyl-1-(4-sulfobutyl)imidazol-3-ium bis((trifluoromethyl)sulfonyl)azanide In neat (no solvent) at 40℃; for 1h;80%
With silica-supported sodium hydrogen sulfate at 115℃; for 3h; Inert atmosphere; Neat (no solvent);79%
trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

1H-2,4,6-tri-isopropyl-1,3,5-triazinium triflate
86774-69-8

1H-2,4,6-tri-isopropyl-1,3,5-triazinium triflate

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

2-(2,4-dimethoxyphenyl)-2,4,6-tri-isopropyl-1,2-dihydro-1,3,5-triazinium triflate
86774-78-9

2-(2,4-dimethoxyphenyl)-2,4,6-tri-isopropyl-1,2-dihydro-1,3,5-triazinium triflate

Conditions
ConditionsYield
In benzene for 1.5h; Ambient temperature;100%
bis(2,2,2-trichloroethyl)azodicarboxylate
38857-88-4

bis(2,2,2-trichloroethyl)azodicarboxylate

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

1-(2,4-dimethoxyphenyl)-1,2-hydrazinedicarboxylic acid bis(2,2,2-trichloroethyl) ester
148678-89-1

1-(2,4-dimethoxyphenyl)-1,2-hydrazinedicarboxylic acid bis(2,2,2-trichloroethyl) ester

Conditions
ConditionsYield
With zinc(II) iodide In dichloromethane at 25℃; for 0.25h;100%
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

2,4,6-trideuterio-resorcinol dimethylether

2,4,6-trideuterio-resorcinol dimethylether

Conditions
ConditionsYield
With perchloric acid; d(4)-methanol at 75℃; for 72h; Inert atmosphere;100%
With water-d2; sulfuric acid-d2 for 48h; Ambient temperature;
With deuteromethanol; toluene-4-sulfonic acid at 70℃; for 72h; deuteration;
3-Bromopropionyl chloride
15486-96-1

3-Bromopropionyl chloride

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

3-bromo-1-(2,4-dimethoxy-phenyl)-propan-1-one
651325-80-3

3-bromo-1-(2,4-dimethoxy-phenyl)-propan-1-one

Conditions
ConditionsYield
titanium tetrachloride In dichloromethane at 0 - 20℃; for 0.5h; Friedel-Crafts reaction;100%
9-benzyl-6-chloro-9H-purine
1928-76-3

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

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

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

6-(1,3-dimethoxyphen-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;85%
diphenylmethyl trimethylsilyl ether
14629-59-5

diphenylmethyl trimethylsilyl ether

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

((4,6-dimethoxy-1,3-phenylene)bis(methanetriyl))tetrabenzene
1224199-14-7

((4,6-dimethoxy-1,3-phenylene)bis(methanetriyl))tetrabenzene

Conditions
ConditionsYield
With iron(III) chloride In 1,2-dichloro-ethane at 20℃; for 20h; Friedel-Crafts Alkylation; Inert atmosphere; regioselective reaction;100%
bis(4-fluorophenyl)methanol, trimethylsilyl derivative

bis(4-fluorophenyl)methanol, trimethylsilyl derivative

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

4,6-Bis(4,4’-difluorobenzhydryl)-1,3-dimethoxybenzene
1590417-65-4

4,6-Bis(4,4’-difluorobenzhydryl)-1,3-dimethoxybenzene

Conditions
ConditionsYield
With iron(III) chloride In 1,2-dichloro-ethane at 20℃; for 0.25h; Friedel-Crafts Alkylation; Inert atmosphere; regioselective reaction;100%
nitropentafluoroacetone
3888-00-4

nitropentafluoroacetone

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

1,3-Dimethoxy-4-(1-hydroxy-2-nitropentafluoroisopropyl)benzene
123716-18-7

1,3-Dimethoxy-4-(1-hydroxy-2-nitropentafluoroisopropyl)benzene

Conditions
ConditionsYield
In nitromethane at 20℃; for 144h;99.7%
acetic anhydride
108-24-7

acetic anhydride

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

2',4'-dimethoxyacetophenone
829-20-9

2',4'-dimethoxyacetophenone

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In acetonitrile for 0.5h; Time; Friedel-Crafts Acylation; Inert atmosphere; Microwave irradiation; Heating; Green chemistry;99%
With GALDEN(R) SV 135; hafnium(IV) bis(perfluorooctanesulfonyl)amide complex In chlorobenzene at 70℃; for 1h; Friedel-Crafts acylation;94%
With Hierarchical-Beta zeolite In neat (no solvent) at 119.84℃; for 4h; Catalytic behavior; Reagent/catalyst; Friedel-Crafts Acylation; Green chemistry;94%
acetyl chloride
75-36-5

acetyl chloride

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

2',4'-dimethoxyacetophenone
829-20-9

2',4'-dimethoxyacetophenone

Conditions
ConditionsYield
With indium(III) tosylate In dodecane; nitromethane for 2h; Solvent; Reagent/catalyst; Temperature; Time; Friedel-Crafts Acylation; Schlenk technique; Reflux;99%
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 1h;88%
With CuII-based Polymeric Sulfonic Acid Catalyst In nitromethane for 0.5h; Reagent/catalyst; Friedel-Crafts Acylation; Schlenk technique; Reflux;84%
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

1-iodo-2,4-dimethoxybenzene
20469-63-0

1-iodo-2,4-dimethoxybenzene

Conditions
ConditionsYield
With iodine; urea hydrogen peroxide adduct for 10h; Sonication;99%
With β-pyridinium dichloroiodide In 2,2,2-trifluoroethanol Reagent/catalyst; Solvent;99%
With hydrogenchloride; α,α,α-trifluorotoluene; dihydrogen peroxide; iodine In water; acetonitrile at 20℃; for 4h;99%
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

1,5-diiodo-2,4-dimethoxy-benzene
51560-17-9

1,5-diiodo-2,4-dimethoxy-benzene

Conditions
ConditionsYield
With dihydrogen peroxide; iodine In water for 0.75h; Sonication;99%
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride In acetic acid for 0.166667h; Ambient temperature;98%
With dihydrogen peroxide; iodine In water at 50℃; for 24h; Green chemistry;96%
Hexafluoroacetone
684-16-2

Hexafluoroacetone

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

2-(2,4-Dimethoxy-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol
115167-63-0

2-(2,4-Dimethoxy-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol

Conditions
ConditionsYield
at 20℃; for 124h;99%
methyl 3,3,3-trifluoropyruvate
13089-11-7

methyl 3,3,3-trifluoropyruvate

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

2-(2,4-Dimethoxy-phenyl)-3,3,3-trifluoro-2-hydroxy-propionic acid methyl ester
115167-60-7

2-(2,4-Dimethoxy-phenyl)-3,3,3-trifluoro-2-hydroxy-propionic acid methyl ester

Conditions
ConditionsYield
at 20℃; for 24h;99%
With In(OSO2CF3)3 In water at 20℃; for 12h; Friedel-Crafts reaction;84%
samarium diiodide bis(tetrahydrofuran) In dichloromethane at 20℃; for 114h; Friedel-Crafts reaction;75%
2',3',4',5',6'-pentamethylacetophenone
2040-01-9

2',3',4',5',6'-pentamethylacetophenone

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

A

pentamethylbenzene,
700-12-9

pentamethylbenzene,

B

2',4'-dimethoxyacetophenone
829-20-9

2',4'-dimethoxyacetophenone

Conditions
ConditionsYield
trifluoroacetic acid for 10h; Heating;A 99%
B 37%
bis(2,2,2-trichlorethyl)azodicarboxylate
38857-88-4

bis(2,2,2-trichlorethyl)azodicarboxylate

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

1-(2,4-dimethoxyphenyl)-1,2-hydrazinedicarboxylic acid bis(2,2,2-trichloroethyl) ester
148678-89-1

1-(2,4-dimethoxyphenyl)-1,2-hydrazinedicarboxylic acid bis(2,2,2-trichloroethyl) ester

Conditions
ConditionsYield
With lithium perchlorate In diethyl ether for 2h; Ambient temperature;99%
4-hydroxymethyl-1,2,5-trimethyl-1H-pyrrole-3-carboxylic acid dibutylamide
244635-59-4

4-hydroxymethyl-1,2,5-trimethyl-1H-pyrrole-3-carboxylic acid dibutylamide

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

4-(2,4-dimethoxy-benzyl)-1,2,5-trimethyl-1H-pyrrole-3-carboxylic acid dibutylamide

4-(2,4-dimethoxy-benzyl)-1,2,5-trimethyl-1H-pyrrole-3-carboxylic acid dibutylamide

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In nitromethane; 1,2-dichloro-ethane at 20℃; for 24h; Alkylation; Friedel-Crafts alkylation;99%
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

2,3,5,6-tetramethyl-4'-thiaspiro[cyclohexane-4,3'-isochroman]-2,5-dien-1,1'-dione
405507-27-9

2,3,5,6-tetramethyl-4'-thiaspiro[cyclohexane-4,3'-isochroman]-2,5-dien-1,1'-dione

2-(5-(2,4-dimethoxyphenyl)-2,3,5,6-tetramethyl-4-oxocyclohexa-1,2-dienylthio)benzoic acid

2-(5-(2,4-dimethoxyphenyl)-2,3,5,6-tetramethyl-4-oxocyclohexa-1,2-dienylthio)benzoic acid

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0℃; for 0.166667h;99%
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

3,5-dimethoxyphenylboronic acid pinacol ester
365564-07-4

3,5-dimethoxyphenylboronic acid pinacol ester

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 1,1'-di(pyridin-2-yl)-1,1',3,3'-tetrahydro-2,2'-bibenzo[d][1,3,2]diazaborole at 100℃; for 16h; Inert atmosphere;99%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; cyclopentyl methyl ether; 1,1'-di(pyridin-2-yl)-1,1',3,3'-tetrahydro-2,2'-bibenzo[d][1,3,2]diazaborole at 100℃; for 16h; Schlenk technique; Inert atmosphere;95%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tert-butyl methyl ether at 80℃; for 1h; Solvent; Microwave irradiation;90%
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

(E)-(1-phenylhept-1-en-6-yne-4,4-diyldisulfonyl)dibenzene

(E)-(1-phenylhept-1-en-6-yne-4,4-diyldisulfonyl)dibenzene

1,1-bis(phenylsulfonyl)-3-[1-(2,4-dimethoxyphenyl)(phenyl)methyl]-4-methylenecyclopentane

1,1-bis(phenylsulfonyl)-3-[1-(2,4-dimethoxyphenyl)(phenyl)methyl]-4-methylenecyclopentane

Conditions
ConditionsYield
With silver hexafluoroantimonate; (triphenylphosphine)gold(I) chloride In diethyl ether at 20℃; for 2h;99%
Stage #1: 1,3-Dimethoxybenzene With silver hexafluoroantimonate; (triphenylphosphine)gold(I) chloride In diethyl ether at 20℃; for 0.05h; Inert atmosphere;
Stage #2: (E)-(1-phenylhept-1-en-6-yne-4,4-diyldisulfonyl)dibenzene In diethyl ether at 20℃; for 2h; Inert atmosphere; diastereoselective reaction;
99%
2-tert-Butyl-4,4-dimethoxy-cyclohexa-2,5-dienone

2-tert-Butyl-4,4-dimethoxy-cyclohexa-2,5-dienone

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

2-(2',4'-dimethoxyphenyl)-4-methoxy-6-tert-butylphenol
1314578-83-0

2-(2',4'-dimethoxyphenyl)-4-methoxy-6-tert-butylphenol

Conditions
ConditionsYield
With aluminium pillared montmorillonite In dichloromethane; 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; chemoselective reaction;99%
benzyl azide
622-79-7

benzyl azide

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

N-{[2,4-bis(methyloxy)phenyl]methyl}aniline
356094-10-5

N-{[2,4-bis(methyloxy)phenyl]methyl}aniline

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 0.05h; Aube-Schmidt rearrangement;99%
3,3-dimethylbutanoic acid chloride
7065-46-5

3,3-dimethylbutanoic acid chloride

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

1-(2',4'-dimethoxyphenyl)-3,3-dimethylbutan-1-one

1-(2',4'-dimethoxyphenyl)-3,3-dimethylbutan-1-one

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; Friedel-Crafts Acylation;99%
2-cyclopentylacetyl chloride
1122-99-2

2-cyclopentylacetyl chloride

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

2-cyclopentyl-1-(2',4'-dimethoxyphenyl)ethanone

2-cyclopentyl-1-(2',4'-dimethoxyphenyl)ethanone

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0 - 20℃;99%

151-10-0Related news

Selective lithiation and crystal structures of G1-carbosilane dendrimers with Dimethoxybenzene (cas 151-10-0) functionalities09/29/2019

Synthetic routes for the following dendrimers are described: Si[CH 2 CH 2 Si(Me) 2 CH 2 -3,5-(MeO) 2 -C 6 H 3 ] 4 (2) and Si[CH 2 CH 2 Si(Me) 2 -2,4-(MeO) 2 -C 6 H 3 ] 4 (4). T...detailed

151-10-0Relevant articles and documents

Enantioselective total synthesis of (-)-blennolide A

Tietze, Lutz F.,Ma, Ling,Reiner, Johannes R.,Jackenkroll, Stefan,Heidemann, Sven

, p. 8610 - 8614 (2013)

Blennolide A can be synthesized through an enantioselective domino-Wacker/carbonylation/methoxylation reaction of 7 a with 96 % ee and an enantioselective Wacker oxidation of 7 b with 89 % ee. Further transformations led to the α,β-unsaturated ester (E)-17, which was subjected to a highly selective Michael addition, introducing a methyl group to give 18 a. After a threefold oxidation and an intramolecular acylation, the tetrahydroxanthenone 4 was obtained, which could be transformed into (-)-blennolide A (ent-1) in a few steps. Domino effect: An enantioselective domino-Wacker/carbonylation/methoxylation process and an enantioselective Wacker oxidation are the key steps in the first total synthesis of the fungal metabolite blennolide A (see scheme). Copyright

Carbon Kinetic Isotope Effects and the Mechanisms of Acid-Catalyzed Decarboxylation of 2,4-Dimethoxybenzoic Acid and CO2 Incorporation into 1,3-Dimethoxybenzene

Vandersteen, Adelle A.,Howe, Graeme W.,Sherwood Lollar, Barbara,Kluger, Ronald

, p. 15049 - 15053 (2017)

The rate of decarboxylation of 2,4-dimethoxybenzoic acid (1) is accelerated in parallel to the extent that the carboxyl group acquires a second proton (1H+). However, the conjugate acid would resist C-C bond breaking as that would lead to formation of doubly protonated CO2. An alternative via formation of a higher-energy protonated phenyl tautomer (2H+) prior to C-C bond breaking would produce protonated CO2, an energetically inaccessible species that can be avoided by transfer of the carboxyl proton to water in the same step. Headspace sampling of CO2 that evolves in the acid-catalyzed process and analysis by GC-IRMS gives a smaller than expected value of 1.022 for the carbon kinetic isotope (CKIE), k12/k13. While this value establishes that C-C cleavage is part of the rate-determining process, intrinsic CKIEs for decarboxylation reactions are typically greater than 1.03. Computational analysis of the C-C bond cleavage from 2H+ gives an intrinsic CKIE of 1.051 and suggests two partially rate-determining steps in the decarboxylation of 1: transfer of the second carboxyl proton to the adjacent phenyl carbon and C-C cleavage in which the carboxyl proton is also transferred to water. Applying the principle of microscopic reversibility to fixation of CO2 in acidic solutions reveals the importance of proton transfers to both carbon and oxygen in the overall fixation process.

-

Thoms,Siebeling

, p. 2135 (1911)

-

Polyfuryl(aryl)alkanes and their derivatives. 12. C-fur bond cleavage in the series of polyfuryl(aryl)alkanes

Butin,Stroganova,Kul'nevich

, p. 153 - 157 (1996)

Reactions taking place with cleavage of the C-Fur bond are examined. It was established that disproportionation in two directions, leading to the formation of tris(5-methyl-2-furyl)methane, takes place when 3,4-dimethoxyphenylbis(5-methyl-2-furyl)methane is boiled in an acidic medium. The acid-catalyzed reaction of 5-methylfurfural with ethylene glycol leads to the formation of either 2-(5-methyl-2-furyl)-1,3-dioxolane or tris(5-methyl-2-furyl)methane, depending on the catalyst. The treatment of 2-(5-methyl-2-furyl)-1,3-dioxolane or gemtris(5·methyl-2-furyl)ethane with trityl perchlorate leads to tris(5-methyl-2-furyl)carbenium or bis(5-methyl-2-furyl)methylcarbenium perchlorates respectively. 1996 Plenum Publishing Corporation.

Zweig et al.

, p. 4124,4125 (1964)

Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation

K?nig, Burkhard,Wang, Hua,Wang, Shun

supporting information, p. 1653 - 1665 (2021/06/17)

Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.

Method for synthesizing M-hydroxyanisole

-

Paragraph 0032-0033; 0052-0053; 0056-0057; 0060-0063, (2021/11/03)

The invention provides a method for synthesizing M-hydroxyanisole. Belong to organic synthesis technical field. The synthesis method comprises the following steps: a vapor phase mixture of resorcinol and methanol is subjected to alkylation reaction through a metal phosphate - alumina fixed phase catalyst to obtain m-hydroxyanisole. The method adopts the gas-solid phase alkylation method to synthesize the M-hydroxyanisole without separating the reaction product from the catalyst, has the characteristic of continuous reaction, and can realize continuous production in the industrial production process. The method utilizes the acid-base catalytic activity center on the surface of the stationary phase catalyst to catalyze the reaction of resorcinol and methanol, and has high resorcinol conversion rate. The method has the advantage of high selectivity of m-hydroxyanisole. Methanol is used as a methylation reagent, and the method is environmentally friendly, low in cost and high in economic benefit.

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