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135-77-3 Usage

Chemical Properties

clear light yellow to yellow-brown liquid

Uses

1,2,4-Trimethoxybenzene is used as a reagent in the synthesis of barbigerone derivatives which can be used as antiproliferative and antiangiogenesis agents. Also used as a reagent in the synthesis of Malvone A (M161525) which is a phytoalexin found in Malva sylvestris.

Check Digit Verification of cas no

The CAS Registry Mumber 135-77-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 5 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 135-77:
(5*1)+(4*3)+(3*5)+(2*7)+(1*7)=53
53 % 10 = 3
So 135-77-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H12O3/c1-10-7-4-5-8(11-2)9(6-7)12-3/h4-6H,1-3H3

135-77-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A10483)  1,2,4-Trimethoxybenzene, 98%   

  • 135-77-3

  • 10g

  • 433.0CNY

  • Detail
  • Alfa Aesar

  • (A10483)  1,2,4-Trimethoxybenzene, 98%   

  • 135-77-3

  • 50g

  • 1167.0CNY

  • Detail

135-77-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,2,4-Trimethoxybenzene

1.2 Other means of identification

Product number -
Other names 1,2,4-TriMethoxybenzene

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:135-77-3 SDS

135-77-3Synthetic route

1,2,4-triacetoxybenzene
613-03-6

1,2,4-triacetoxybenzene

dimethyl sulfate
77-78-1

dimethyl sulfate

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
Stage #1: 1,2,4-triacetoxybenzene With methanol; potassium hydroxide at 40℃; for 0.133333h; Inert atmosphere;
Stage #2: dimethyl sulfate With potassium carbonate at 60℃; for 0.5h; pH=8.5; Reagent/catalyst; Inert atmosphere;
99.4%
With methanol; sodium hydroxide
Alkaline aq. solution;
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

dimethyl sulfate
77-78-1

dimethyl sulfate

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 12h;99%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 16h; Inert atmosphere;96%
With sodium hydroxide
2,4-dibromoanisole
21702-84-1

2,4-dibromoanisole

sodium methylate
124-41-4

sodium methylate

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With methanol; Methyl formate; copper(l) chloride at 115℃; for 2h; Autoclave; Green chemistry;98%
3,4-dimethoxyphenol
2033-89-8

3,4-dimethoxyphenol

methyl iodide
74-88-4

methyl iodide

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
Stage #1: 3,4-dimethoxyphenol With potassium carbonate In acetone at 40 - 45℃; for 1h; Inert atmosphere;
Stage #2: methyl iodide In acetone for 7h; Reflux; Inert atmosphere;
97%
With n-butyllithium In tetrahydrofuran at 0℃;
3,4-dimethoxyphenol
2033-89-8

3,4-dimethoxyphenol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With magnesium oxide In N,N-dimethyl-formamide at 170℃; for 0.5h; Microwave irradiation; Green chemistry;96%
2,5-dimethoxyphenol
18113-18-3

2,5-dimethoxyphenol

dimethyl sulfate
77-78-1

dimethyl sulfate

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide95%
3,4-dimethoxyphenol
2033-89-8

3,4-dimethoxyphenol

dimethyl sulfate
77-78-1

dimethyl sulfate

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With potassium hydroxide for 1.5h; Heating;90%
1-styryl-2,4,5-trimethoxybenzene

1-styryl-2,4,5-trimethoxybenzene

A

2-phenylnaphthalene
612-94-2

2-phenylnaphthalene

B

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With trifluoroacetic acid In water at 80℃; for 0.5h; Diels-Alder Cycloaddition;A 90%
B n/a
2,4,5-trimethoxybenzoic acid potassium salt

2,4,5-trimethoxybenzoic acid potassium salt

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With trifluoroacetic acid; palladium(II) trifluoroacetate In dimethyl sulfoxide at 70℃;55%
Stage #1: 2,4,5-trimethoxybenzoic acid potassium salt With palladium(II) trifluoroacetate In dimethyl sulfoxide at 80℃; for 0.5h;
Stage #2: With trifluoroacetic acid In dimethyl sulfoxide at 70℃;
55%
N-acetylindole
576-15-8

N-acetylindole

sodium 2,4,5-trimethoxybenzoate
83813-98-3

sodium 2,4,5-trimethoxybenzoate

A

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

B

2-(2',4',5'-trimethoxyphenyl)-N-acetylindole
1235306-66-7

2-(2',4',5'-trimethoxyphenyl)-N-acetylindole

C

2,2',4,4',5,5'-hexamethoxybiphenyl
1702-67-6

2,2',4,4',5,5'-hexamethoxybiphenyl

Conditions
ConditionsYield
Stage #1: sodium 2,4,5-trimethoxybenzoate With palladium(II) trifluoroacetate In dimethyl sulfoxide at 80℃; for 0.5h; Inert atmosphere;
Stage #2: N-acetylindole With dimethyl sulfoxide; propionic acid In 1,4-dioxane at 80℃; for 15h; Inert atmosphere;
A 51%
B 13%
C 11%
4-nitro-1H-pyrazole
2075-46-9

4-nitro-1H-pyrazole

1,1,4,4-tetramethoxycyclohexa-2,5-diene
15791-03-4

1,1,4,4-tetramethoxycyclohexa-2,5-diene

A

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

B

1,4-dimethoxy-2-(4-nitropyrazol-1-yl)benzene

1,4-dimethoxy-2-(4-nitropyrazol-1-yl)benzene

Conditions
ConditionsYield
at 110℃; for 5h;A 44%
B 44%
asaronic acid
490-64-2

asaronic acid

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With silver(I) acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 16h; Inert atmosphere;43%
With palladium(II) trifluoroacetate; trifluoroacetic acid In dimethyl sulfoxide; N,N-dimethyl-formamide at 70℃; for 24h;25%
With extinguished lime; calcium carbonate bei der Destillation;
With Tetrabutylammonium hydrogen diacetate; silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane at 120℃; for 24h; Inert atmosphere;90 %Chromat.
3,5-dimethyl-4-nitro-1H-pyrazole
14531-55-6

3,5-dimethyl-4-nitro-1H-pyrazole

1,1,4,4-tetramethoxycyclohexa-2,5-diene
15791-03-4

1,1,4,4-tetramethoxycyclohexa-2,5-diene

A

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

B

2-(3,5-dimethyl-4-nitropyrazol-1-yl)-1,4-dimethoxybenzene

2-(3,5-dimethyl-4-nitropyrazol-1-yl)-1,4-dimethoxybenzene

Conditions
ConditionsYield
at 110℃; for 5h;A 36%
B 33%
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
at 50℃; Reaktion ueber mehrere Stufen;
1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone
487-49-0

1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide at 50℃; Reaktion ueber mehrere Stufen;
methoxyhydroquinone
824-46-4

methoxyhydroquinone

dimethyl sulfate
77-78-1

dimethyl sulfate

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

2,4,5-trihydroxybenzoic acid
610-90-2

2,4,5-trihydroxybenzoic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With potassium hydroxide
methoxyhydroquinone
824-46-4

methoxyhydroquinone

methyl iodide
74-88-4

methyl iodide

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With potassium hydroxide
2,4-dimethoxyphenol
13330-65-9

2,4-dimethoxyphenol

sodium methylate
124-41-4

sodium methylate

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide
2-chloro-1,4-dimethoxybenzene
2100-42-7

2-chloro-1,4-dimethoxybenzene

potassium methanolate
865-33-8

potassium methanolate

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With 18-crown-6 ether; iodine; chromium(0) hexacarbonyl 1.) diglyme, cyclohexane, reflux, 95 h, 2.) benzene, 70 deg C, 3.5 h, 3.) THF, R.T., 30 min; Yield given. Multistep reaction;
1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)ethanol
17078-88-5

1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)ethanol

sodium methylate
124-41-4

sodium methylate

A

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

B

1-methoxy-2-(methoxymethoxy)benzene
73220-26-5

1-methoxy-2-(methoxymethoxy)benzene

C

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

D

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With sodium perchlorate In methanol; dichloromethane Product distribution; Mechanism; anodic oxidation (undivided cell, Pt foil anode, W wire cathode, 50 mA, 3 F mol-1), other substrates;
4-methoxy-phenol
150-76-5

4-methoxy-phenol

dimethyl sulfate
77-78-1

dimethyl sulfate

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With oxygen; copper; sodium carbonate; copper(I) chloride 1.) CH3CN; Multistep reaction;
(+-)-2.4-dihydroxy-benzoin

(+-)-2.4-dihydroxy-benzoin

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide at 50℃; Reaktion ueber mehrere Stufen;
asaronic acid
490-64-2

asaronic acid

lime/chalk/

lime/chalk/

A

carbon dioxide
124-38-9

carbon dioxide

B

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
bei der Destillation;
methanol
67-56-1

methanol

diazotized 6-amino-2.3-dimethoxy-benzoic acid

diazotized 6-amino-2.3-dimethoxy-benzoic acid

A

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

B

2,3-dimethoxybenzoic acid
1521-38-6

2,3-dimethoxybenzoic acid

Conditions
ConditionsYield
With hydrogenchloride
methanol
67-56-1

methanol

2,4,5-trihydroxybenzoic acid
610-90-2

2,4,5-trihydroxybenzoic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

KOH-solution

KOH-solution

A

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

B

asaronic acid
490-64-2

asaronic acid

C

2,2',4,4',5,5'-hexamethoxybiphenyl
1702-67-6

2,2',4,4',5,5'-hexamethoxybiphenyl

D

2-hydroxy-4,5-dimethoxybenzoic acid
5722-93-0

2-hydroxy-4,5-dimethoxybenzoic acid

1,2,4-trimethoxybenzene radical cation
135-77-3

1,2,4-trimethoxybenzene radical cation

7,8-dihydro-8-oxo-2'-deoxyguanosine
88847-89-6

7,8-dihydro-8-oxo-2'-deoxyguanosine

A

2-Amino-8-hydroxy-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one

2-Amino-8-hydroxy-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one

B

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
In water at 20 - 25℃; pH=3.0; Kinetics; Equilibrium constant; Oxidation;
p-benzoquinone
106-51-4

p-benzoquinone

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: Alkaline aq. solution
View Scheme
sodium 2,4,5-trimethoxybenzoate
83813-98-3

sodium 2,4,5-trimethoxybenzoate

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With palladium diacetate; Tetrabutylammonium hydrogen diacetate; tricyclohexylphosphine In 1,2-dimethoxyethane at 120℃; for 24h; Inert atmosphere;8 %Chromat.
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

diphenyl(2,4,5-trimethoxyphenyl)methane

diphenyl(2,4,5-trimethoxyphenyl)methane

Conditions
ConditionsYield
With o-benzenedisulfonimide In neat (no solvent) at 20℃; for 1.5h; Friedel-Crafts Alkylation;100%
With 2C2H6O2*ZnCl2 at 90℃; for 1h; Temperature; Reagent/catalyst; Friedel-Crafts Alkylation;85%
With hydrogenchloride; ethanol
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

1,2,4-trimethoxy-5-nitrobenzene
14227-14-6

1,2,4-trimethoxy-5-nitrobenzene

Conditions
ConditionsYield
With Nitrogen dioxide In dichloromethane in the dark; -78 deg C, 2 min; RT, 15 min;100%
With tert.-butylnitrite In acetonitrile at 20℃; for 1h;95%
With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide at 20℃; for 2h; Ionic liquid;93%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

1-iodo-2,4,5-trimethoxybenzene
23149-33-9

1-iodo-2,4,5-trimethoxybenzene

Conditions
ConditionsYield
With iodine; silver trifluoroacetate In dichloromethane at 0℃; for 8h;100%
With N-iodo-succinimide; trifluoroacetic acid In acetonitrile at 20℃; for 0.1h;99%
With N-iodo-succinimide In acetonitrile at 20℃; for 16h; Inert atmosphere; Schlenk technique;99%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

1-bromo-2,4,5-trimethoxybenzene
20129-11-7

1-bromo-2,4,5-trimethoxybenzene

Conditions
ConditionsYield
With poly(4-vinylpyridine)-supported bromate; potassium bromide In acetonitrile for 5h;100%
With bromine In dichloromethane at 0℃;100%
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 2.5h; Heating;100%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

1,1'-[(4-nitrophenyl)methanediyl]bis(2,4,5-trimethoxybenzene)
54921-89-0

1,1'-[(4-nitrophenyl)methanediyl]bis(2,4,5-trimethoxybenzene)

Conditions
ConditionsYield
With o-benzenedisulfonimide at 130℃; for 0.25h; Friedel Crafts alkylation;100%
With air; iodine In toluene at 20℃; for 72h; Friedel Crafts alkylation;99%
With niobium pentachloride In dichloromethane at 0 - 20℃; for 24h; Friedel-Crafts Alkylation;98%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

methyl iodide
74-88-4

methyl iodide

2,3,6-trimethoxytoluene
25576-97-0

2,3,6-trimethoxytoluene

Conditions
ConditionsYield
Stage #1: 1,2,4-trimethoxy-benzene With n-butyllithium
Stage #2: methyl iodide
100%
Stage #1: 1,2,4-trimethoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; hexane for 1h; Inert atmosphere;
99%
Stage #1: 1,2,4-trimethoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.33333h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;
99%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

4,4'-Dimethoxybenzhydrol
728-87-0

4,4'-Dimethoxybenzhydrol

bis(4-methoxyphenyl)(2,4,5-trimethoxyphenyl)methane
1562305-57-0

bis(4-methoxyphenyl)(2,4,5-trimethoxyphenyl)methane

Conditions
ConditionsYield
With o-benzenedisulfonimide In neat (no solvent) at 20℃; for 0.25h; Friedel-Crafts Alkylation;100%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

C9H10(2)H2O3

C9H10(2)H2O3

Conditions
ConditionsYield
With perchloric acid; d(4)-methanol at 75℃; for 15h; Inert atmosphere;100%
formaldehyd
50-00-0

formaldehyd

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

bis(2,4,5-trimethoxyphenyl)methane
30038-32-5

bis(2,4,5-trimethoxyphenyl)methane

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In acetonitrile at 0 - 20℃; for 1h; Friedel-Crafts Alkylation;99%
With 1-methyl-3-(propyl-3-sulfonyl)imidazolium trifluoromethanesulfonate In neat (no solvent) at 40℃; for 0.5h; Friedel-Crafts Alkylation; Green chemistry;99%
With sulfuric acid; acetic acid
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

benzaldehyde
100-52-7

benzaldehyde

1,1'-(phenylmethanediyl)bis(2,4,5-trimethoxybenzene)
54921-86-7

1,1'-(phenylmethanediyl)bis(2,4,5-trimethoxybenzene)

Conditions
ConditionsYield
With 1-methyl-3-(propyl-3-sulfonyl)imidazolium trifluoromethanesulfonate In neat (no solvent) at 40℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Temperature; Friedel-Crafts Alkylation; Green chemistry;99%
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.0833333h; Friedel-Crafts Alkylation;95%
With o-benzenedisulfonimide at 130℃; for 3.5h; Friedel Crafts alkylation; neat (no solvent);93%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

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

1,2,4-trimethoxy-5-phenylsulfanylbenzene

1,2,4-trimethoxy-5-phenylsulfanylbenzene

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
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

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

1,2,4-trimethoxy-5-phenylsulfanylbenzene

1,2,4-trimethoxy-5-phenylsulfanylbenzene

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -30 - 20℃; for 0.166667h;99%
2-Phenylpropanal
34713-70-7

2-Phenylpropanal

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

C27H32O6
1195735-85-3

C27H32O6

Conditions
ConditionsYield
With air; iodine In toluene at 20℃; for 130h; Friedel Crafts alkylation;99%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

1,1'-[(4-chlorophenyl)methanediyl]bis(2,4,5-trimethoxybenzene)
1190880-27-3

1,1'-[(4-chlorophenyl)methanediyl]bis(2,4,5-trimethoxybenzene)

Conditions
ConditionsYield
With niobium pentachloride In dichloromethane at 0 - 20℃; for 24h; Friedel-Crafts Alkylation;99%
With 1-methyl-3-(propyl-3-sulfonyl)imidazolium trifluoromethanesulfonate In neat (no solvent) at 40℃; for 0.5h; Friedel-Crafts Alkylation; Green chemistry;91%
With silica supported o-benzenedisulfonimide at 20℃; for 1.25h; Friedel Crafts alkylation; neat (no solvent);90%
With air; iodine In toluene at 20℃; for 72h; Friedel Crafts alkylation;88%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

5,5'-(cyclohexylmethylene)bis(1,2,4-trimethoxybenzene)
1195735-86-4

5,5'-(cyclohexylmethylene)bis(1,2,4-trimethoxybenzene)

Conditions
ConditionsYield
With air; iodine In toluene at 20℃; for 72h; Friedel Crafts alkylation;99%
With trifluorormethanesulfonic acid In acetonitrile at 0 - 20℃; for 24h; Friedel-Crafts Alkylation;83%
6-bromohexanoyl chloride
22809-37-6

6-bromohexanoyl chloride

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

6-bromo-1-(2,4,5-trimethoxyphenyl)hexan-1-one
1268333-97-6

6-bromo-1-(2,4,5-trimethoxyphenyl)hexan-1-one

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at -10 - 20℃; Friedel Crafts Acylation;99%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

3-[bis(2,4,5-trimethoxyphenyl)methyl]pyridine
1431862-12-2

3-[bis(2,4,5-trimethoxyphenyl)methyl]pyridine

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In acetonitrile at 0 - 20℃; for 24h; Friedel-Crafts Alkylation;99%
1-(4-methoxyphenyl)but-3-en-1-ol
24165-60-4

1-(4-methoxyphenyl)but-3-en-1-ol

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

1,2,4-trimethoxy-5-[1-(4-methoxyphenyl)but-3-en-1-yl]benzene
1431862-22-4

1,2,4-trimethoxy-5-[1-(4-methoxyphenyl)but-3-en-1-yl]benzene

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In acetonitrile at 0 - 20℃; for 0.75h;99%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

triethyl phosphite
122-52-1

triethyl phosphite

diethyl (2,4,5-trimethoxyphenyl)phosphonate

diethyl (2,4,5-trimethoxyphenyl)phosphonate

Conditions
ConditionsYield
With ammonium peroxydisulfate; tris(2,2′-bipyrazine-N1,N1′)ruthenium(II) hexafluorophosphate In acetonitrile at 25℃; for 20h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Irradiation;99%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

trimethyl orthoformate
149-73-5

trimethyl orthoformate

tris(2,4,5-trimethoxyphenyl)methane
14470-07-6

tris(2,4,5-trimethoxyphenyl)methane

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In neat liquid at 20℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Friedel-Crafts Alkylation;99%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

2,2',4,4',5,5'-hexamethoxybiphenyl
1702-67-6

2,2',4,4',5,5'-hexamethoxybiphenyl

Conditions
ConditionsYield
With molybdenum(V) chloride In dichloromethane at 20℃; for 0.5h;98%
With boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at -40℃; for 1.5h;92%
With iron(III) chloride on silica In dichloromethane Product distribution; Mechanism; variation of conditions, other dimethoxyaryls;89%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

1,1′-[(3-nitrophenyl)methanediyl]bis(2,4,5-trimethoxybenzene)
54921-75-4

1,1′-[(3-nitrophenyl)methanediyl]bis(2,4,5-trimethoxybenzene)

Conditions
ConditionsYield
With niobium pentachloride In dichloromethane at 0 - 20℃; for 24h; Friedel-Crafts Alkylation;98%
With PEG-400 at 50 - 60℃; for 2h; Friedel-Crafts Alkylation; Green chemistry;95%
With hydrogenchloride; acetic acid
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

1,1'-[(4-fluorophenyl)methanediyl]bis(2,4,5-trimethoxybenzene)
1195735-76-2

1,1'-[(4-fluorophenyl)methanediyl]bis(2,4,5-trimethoxybenzene)

Conditions
ConditionsYield
With niobium pentachloride In dichloromethane at 0 - 20℃; for 24h; Friedel-Crafts Alkylation;98%
With air; iodine In toluene at 20℃; for 72h; Friedel Crafts alkylation;97%
With 1-methyl-3-(propyl-3-sulfonyl)imidazolium trifluoromethanesulfonate In neat (no solvent) at 40℃; for 1h; Friedel-Crafts Alkylation; Green chemistry;92%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

1,1'-[(4-bromophenyl)methanediyl]bis(2,4,5-trimethoxybenzene)
1195735-78-4

1,1'-[(4-bromophenyl)methanediyl]bis(2,4,5-trimethoxybenzene)

Conditions
ConditionsYield
With air; iodine In toluene at 20℃; for 72h; Friedel Crafts alkylation;98%
With trifluorormethanesulfonic acid In acetonitrile at 0 - 20℃; for 24h; Friedel-Crafts Alkylation;96%
With niobium pentachloride In dichloromethane at 0 - 20℃; for 24h; Friedel-Crafts Alkylation;96%
difluoromethyl phenyl sulfide
1535-67-7

difluoromethyl phenyl sulfide

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

asaraldehyde
4460-86-0

asaraldehyde

Conditions
ConditionsYield
Stage #1: difluoromethyl phenyl sulfide; 1,2,4-trimethoxy-benzene With tin(IV) chloride In dichloromethane at 20℃; for 2h; Inert atmosphere;
Stage #2: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dichloromethane; water; dimethyl sulfoxide at 20℃; for 2h;
98%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

prenyl bromide
870-63-3

prenyl bromide

1,2,4-trimethoxy-3-(3-methylbut-2-en-1-yl)benzene

1,2,4-trimethoxy-3-(3-methylbut-2-en-1-yl)benzene

Conditions
ConditionsYield
Stage #1: 1,2,4-trimethoxy-benzene With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #2: prenyl bromide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
98%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

1,1'-[(3,4,5-trimethoxyphenyl)methanediyl]bis(2,4,5-trimethoxybenzene)
54921-97-0

1,1'-[(3,4,5-trimethoxyphenyl)methanediyl]bis(2,4,5-trimethoxybenzene)

Conditions
ConditionsYield
With niobium pentachloride In dichloromethane at 0 - 20℃; for 24h; Friedel-Crafts Alkylation;98%

135-77-3Relevant articles and documents

Development of a catalytic aromatic decarboxylation reaction

Dickstein, Joshua S.,Mulrooney, Carol A.,O'Brien, Erin M.,Morgan, Barbara J.,Kozlowski, Marisa C.

, p. 2441 - 2444 (2007)

A palladium-catalyzed aromatic decarboxylation reaction has been developed. With electron-rich aromatic adds, the reaction proceeds efficiently under fairly mild conditions in good yields. The method was useful with complex functionalized substrates containing hindered carboxylic adds.

Syntheses of benzophenone-xanthone hybrid polyketides and their antibacterial activities

Kodama, Takeshi,Ito, Takuya,Dibwe, Dya Fita,Woo, So-Yeun,Morita, Hiroyuki

, p. 2397 - 2400 (2017)

Muchimangins are benzophenone-xanthone hybrid polyketides produced by Securidaca longepedunculata. However, their biological activities have not been fully investigated, since they are minor constituents in this plant. To evaluate the possibility of muchimangins as antibacterial agent candidates, five muchimangin analogs were synthesized from 2,4,5-trimethoxydiphenyl methanol and the corresponding xanthones, by utilizing p-toluenesulfonic acid monohydrate for the Br?nsted acid-catalysis. The antibacterial assays against Gram-positive bacteria, Staphylococcus aureus and Bacillus subtilis, and Gram-negative bacteria, Klebsiella pneumoniae and Escherichia coli, revealed that the muchimangin analogs (±)-1,3,6,8-tetrahydroxy-4-(phenyl-(2′,4′,5′-trimethoxyphenyl)methyl)-xanthone (1), (±)-1,3,6-trihydroxy-4-(phenyl-(2′,4′,5′-trimethoxyphenyl)methyl)-xanthone (2), and (±)-1,3-dihydroxy-4-(phenyl-(2′,4′,5′-trimethoxyphenyl)methyl)-xanthone (3) showed significant activities against S. aureus, with MIC values of 10.0, 10.0, and 25.0?μM, respectively. Analogs (±)-1 and (±)-2 also exhibited antibacterial activities against B. subtilis, with MIC values of 50.0 and 12.5?μM, respectively. Furthermore, (+)-3 enhanced the antibacterial activity against S. aureus, with a MIC value of 10?μM.

A ligand-free, powerful, and practical method for methoxylation of unactivated aryl bromides by use of the CuCl/HCOOMe/MeONa/MeOH system

Guo, Ying,Ji, Si-Zhe,Chen, Cheng,Liu, Hong-Wei,Zhao, Jian-Hong,Zheng, Yu-Lin,Ji, Ya-Fei

, p. 8651 - 8664 (2015/03/05)

A ligand-free, powerful, and practical method for mono and polymethoxylation of unactivated aryl bromides has been developed; CuCl was used as catalyst, HCOOMe as cocatalyst, and methanolic MeONa as both nucleophile and solvent. This eco-friendly procedure is characterized by operational simplicity, inexpensive substrates (unactivated mono to polybromoarenes), full conversion, and direct recovery of pure MeOH.

Magnesium oxide as a heterogeneous and recyclable base for the N-methylation of indole and O-methylation of phenol using dimethyl carbonate as a green methylating agent

Gadge, Sandip T.,Mishra, Ashish,Gajengi, Aravind L.,Shahi, Nileshkumar V.,Bhanage, Bhalchandra M.

, p. 50271 - 50276 (2014/12/10)

This work reports a mild efficient and sustainable protocol for N-methylation of indole and O-methylation of phenol using dimethylcarbonate as an environmentally safe, non-toxic, biodegradable and green methylating agent under microwave conditions. Magnesium oxide (MgO) has been employed as a heterogeneous and recyclable base for clean N-methylation of indole and O-methylation of phenol with dimethylcarbonate. Basic properties of the fresh and recycled MgO were measured by temperature programmed desorption (CO2-TPD) analysis. The CO2-TPD runs suggested that both strong and moderately basic sites are present on the oxide, while only the moderately basic sites are responsible for the N-and O-methylation of indole and phenol, respectively, using DMC as a methylating agent. The CO2-TPD analysis showed that the basic sites on fresh and recycled MgO were comparable. The MgO was isolated by simple filtration and recycled efficiently without loss in activity and selectivity.

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