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6443-69-2

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6443-69-2 Usage

Chemical Properties

CLEAR YELLOW LIQUID

Uses

Different sources of media describe the Uses of 6443-69-2 differently. You can refer to the following data:
1. 3,4,5-Trimethoxytoluene is a reagent for oxadiazolylindazole sodium channel modulators which are neuroprotective toward hippocampal neurons.
2. 3,4,5-Trimethoxytoluene was used as a substructure model compound in the reaction of trimethoprim with free available chlorine (i.e. HOCl).

Check Digit Verification of cas no

The CAS Registry Mumber 6443-69-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,4,4 and 3 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 6443-69:
(6*6)+(5*4)+(4*4)+(3*3)+(2*6)+(1*9)=102
102 % 10 = 2
So 6443-69-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H14O3/c1-7-5-8(11-2)10(13-4)9(6-7)12-3/h5-6H,1-4H3

6443-69-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A15201)  3,4,5-Trimethoxytoluene, 98%   

  • 6443-69-2

  • 5g

  • 257.0CNY

  • Detail
  • Alfa Aesar

  • (A15201)  3,4,5-Trimethoxytoluene, 98%   

  • 6443-69-2

  • 25g

  • 1088.0CNY

  • Detail
  • Alfa Aesar

  • (A15201)  3,4,5-Trimethoxytoluene, 98%   

  • 6443-69-2

  • 50g

  • 1985.0CNY

  • Detail
  • Alfa Aesar

  • (A15201)  3,4,5-Trimethoxytoluene, 98%   

  • 6443-69-2

  • 100g

  • 3668.0CNY

  • Detail

6443-69-2SDS

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 3,4,5-Trimethoxytoluene

1.2 Other means of identification

Product number -
Other names 1,2,3-trimethoxy-5-methylbenzene

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:6443-69-2 SDS

6443-69-2Synthetic route

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

3,4,5-trimethoxy-benzaldehyde

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

Conditions
ConditionsYield
Stage #1: 3,4,5-trimethoxy-benzaldehyde With hydrazine hydrate; potassium hydroxide In ethylene glycol at 70℃; for 2h; Wolff-Kishner Reduction;
Stage #2: In ethylene glycol at 150℃; for 2h;
100%
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol at 20℃; under 760.051 Torr; for 1.5h;98%
With hydrogen; palladium on activated charcoal In acetic acid under 30002.4 Torr; for 72h; Ambient temperature;97%
(2,3,4-trimethoxy-6-methylphenyl)boronic acid
212573-50-7

(2,3,4-trimethoxy-6-methylphenyl)boronic acid

N,N-diethyl-6-iodo-3-isopropoxy-2-(trimethylsilyl)benzamide
1432583-85-1

N,N-diethyl-6-iodo-3-isopropoxy-2-(trimethylsilyl)benzamide

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;100%
(2,3,4-trimethoxy-6-methylphenyl)boronic acid
212573-50-7

(2,3,4-trimethoxy-6-methylphenyl)boronic acid

N,N-diethyl-2-iodo-5-isopropoxybenzamide
1432583-86-2

N,N-diethyl-2-iodo-5-isopropoxybenzamide

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;100%
1-(2-hexyl)-2,5-dimethylbenzene
4003-98-9

1-(2-hexyl)-2,5-dimethylbenzene

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

Conditions
ConditionsYield
In water98.5%
p-toluenesulfonic acid

p-toluenesulfonic acid

5-(p-xylyl)-hexene
153754-60-0

5-(p-xylyl)-hexene

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

Conditions
ConditionsYield
98%
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

N-butylamine
109-73-9

N-butylamine

A

N-butyl-3,4,5-trimethoxybenzylamine hydrochloride
935250-90-1

N-butyl-3,4,5-trimethoxybenzylamine hydrochloride

B

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

Conditions
ConditionsYield
With chloroform; 10% Pd/C; hydrogen In methanol at 20℃; under 760.051 Torr; for 2h; chemoselective reaction;A 97%
B 4%
methanol
67-56-1

methanol

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

3,4,5-trimethoxy-benzaldehyde

A

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

B

(3,4,5-trimethoxyphenyl)methanol
3840-31-1

(3,4,5-trimethoxyphenyl)methanol

C

1,2,3-trimethoxy-5-(methoxymethyl)benzene
75921-68-5

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

Conditions
ConditionsYield
With hydrogen; acetic acid; palladium on activated charcoal In methanol at 20℃; under 760.051 Torr; for 2h;A 7%
B 75%
C 13%
With hydrogen at 160℃; under 15001.5 Torr; for 4h; Autoclave; Green chemistry;A 34.9 %Chromat.
B 53 %Chromat.
C 12.1 %Chromat.
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

isopropyl alcohol
67-63-0

isopropyl alcohol

A

3,4,5-trimethoxybenzyl isopropyl ether

3,4,5-trimethoxybenzyl isopropyl ether

B

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

C

(3,4,5-trimethoxyphenyl)methanol
3840-31-1

(3,4,5-trimethoxyphenyl)methanol

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal at 20℃; under 760.051 Torr; for 7h;A 6%
B 75%
C 16%
3,4,5-Trimethoxybenzyl pivalate
157843-82-8

3,4,5-Trimethoxybenzyl pivalate

A

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

B

Trimethylacetic acid
75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide for 24h; Inert atmosphere; Glovebox; UV-irradiation;A 11%
B 73%
N,N-Dimethyl-N-<(trimethylsilyl)methyl>-3,4,5-trimethoxybenzylammonium iodide

N,N-Dimethyl-N-<(trimethylsilyl)methyl>-3,4,5-trimethoxybenzylammonium iodide

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

Conditions
ConditionsYield
With cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide for 0.5h; Ambient temperature;71%
3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); 1,1,3,3-Tetramethyldisiloxane; potassium tert-butylate; 1,3-bis(cyclohexyl)imidazolium tetrafluoroborate In toluene at 90℃; for 6h; Glovebox; Inert atmosphere; Sealed tube;69%
With lithium aluminium tetrahydride; hydrogen; palladium on activated charcoal 1.) Et2O; 2.) ethanol, 1 atm; Multistep reaction;
Multi-step reaction with 3 steps
1: 86.4 percent / 99 percent N2H4*H2O / methanol / 5 h / Heating
2: 85 percent / K3Fe(CN)6; 25 percent NH4OH / H2O; CH2Cl2 / 4 h / 20 °C
3: 65 percent / Zn-Hg / acetic acid; toluene; H2O / 0.75 h / Heating
View Scheme
methanol
67-56-1

methanol

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

3,4,5-trimethoxy-benzaldehyde

A

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

B

3,4,5-trimethoxybenzaldehyde dimethyl acetal
59276-37-8

3,4,5-trimethoxybenzaldehyde dimethyl acetal

C

1,2,3-trimethoxy-5-(methoxymethyl)benzene
75921-68-5

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

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal at 20℃; under 760.051 Torr; for 0.0833333h;A 5%
B 27%
C 65%
(3,4,5-trimethoxyphenyl)methanol
3840-31-1

(3,4,5-trimethoxyphenyl)methanol

A

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

B

brittonin A
33284-74-1

brittonin A

Conditions
ConditionsYield
Stage #1: (3,4,5-trimethoxyphenyl)methanol With tert.-butyl lithium In tetrahydrofuran; n-heptane at -78 - 20℃; for 0.333333h; Inert atmosphere;
Stage #2: With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran for 24h; Inert atmosphere; Reflux;
A 7%
B 60%
With triphenylphosphine In 1,4-dioxane at 200℃; for 16h; Autoclave; Inert atmosphere;A 54%
B 27%
With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran for 1h; Inert atmosphere; Reflux;A 40%
B 14%
methanol
67-56-1

methanol

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

3,4,5-trimethoxy-benzaldehyde

A

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

B

1,2,3-trimethoxy-5-(methoxymethyl)benzene
75921-68-5

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

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal at 20℃; under 760.051 Torr; for 0.133333h;A 50%
B 48%
With palladium 10% on activated carbon; hydrogen at 20℃; for 3.5h;A 42 %Spectr.
B 58 %Spectr.
1,2,3-trimethoxy-5-((undecyloxy)methyl)benzene
1426824-96-5

1,2,3-trimethoxy-5-((undecyloxy)methyl)benzene

A

undecyl alcohol
112-42-5

undecyl alcohol

B

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

Conditions
ConditionsYield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide for 72h; Inert atmosphere; Glovebox; UV-irradiation;A 46%
B n/a
methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

3,4,5-trimethoxyphenyl 4-methylbenzenesulfonate
312299-66-4

3,4,5-trimethoxyphenyl 4-methylbenzenesulfonate

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,2-dimethoxyethane)dichloronickel(II); tetra-(n-butyl)ammonium iodide; lithium chloride; zinc In N,N-dimethyl acetamide at 40℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;40%
3,4,5-trimethoxybenzyltrimethylammonium iodide
34274-12-9

3,4,5-trimethoxybenzyltrimethylammonium iodide

A

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

B

brittonin A
33284-74-1

brittonin A

Conditions
ConditionsYield
With nickel(II) iodide; manganese; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl acetamide at 120℃; for 24h; Inert atmosphere;A 36%
B 15%
5-methylpyrogallol
609-25-6

5-methylpyrogallol

dimethyl sulfate
77-78-1

dimethyl sulfate

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

Conditions
ConditionsYield
With sodium hydroxide at 70 - 80℃;
3,4,5-trimethoxybenzonitrile
1885-35-4

3,4,5-trimethoxybenzonitrile

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

Conditions
ConditionsYield
With p-menth-1-ene; palladium on activated charcoal
2,3-dimethoxy-5-methylphenol
1128-32-1

2,3-dimethoxy-5-methylphenol

dimethyl sulfate
77-78-1

dimethyl sulfate

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

Conditions
ConditionsYield
With potassium carbonate In acetone for 2h; Heating; Yield given;
5-iodo-1,2,3-trimethoxybenzene
25245-29-8

5-iodo-1,2,3-trimethoxybenzene

methyl iodide
74-88-4

methyl iodide

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

Conditions
ConditionsYield
With n-butyllithium 1.) THF, hexane, -78 deg C, 2.) -78 deg C; Yield given. Multistep reaction;
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

2-bromo-3,4,5-trimethoxy-1-methylbenzene
72326-72-8

2-bromo-3,4,5-trimethoxy-1-methylbenzene

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid; sodium bromide In water at 20℃; for 1h;100%
With sulfuric acid; dihydrogen peroxide; sodium bromide In ethanol at 25℃; for 1h;100%
With dihydrogen peroxide; acetic acid; sodium bromide In water at 40℃; for 2h;98.1%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

2,3-Dimethoxy-5-methyl-1,4-benzoquinone
605-94-7

2,3-Dimethoxy-5-methyl-1,4-benzoquinone

Conditions
ConditionsYield
With dipotassium peroxodisulfate; formic acid In methanol; water at 60℃; for 2.16h; Reagent/catalyst; Temperature; Solvent;99%
Stage #1: 3,4,5-trimethoxytoluene With dihydrogen peroxide; toluene-4-sulfonic acid; acetic acid at 75℃; for 0.5h;
Stage #2: With nitric acid In water at 0 - 5℃; for 0.00833333h;
88%
With dipotassium peroxodisulfate; formic acid; water at 25℃; for 4h; Reagent/catalyst;88%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2,3,4-trimethoxy-6-methylbenzaldehyde
22383-85-3

2,3,4-trimethoxy-6-methylbenzaldehyde

Conditions
ConditionsYield
With trichlorophosphate Vilsmeier-Haack Formylation;99%
With trichlorophosphate at 65℃; for 5h; Vilsmeier-Haack reaction;95%
With trichlorophosphate at 5 - 80℃; for 7h; Vilsmeier-Haack reaction; Inert atmosphere;92.4%
With trichlorophosphate at 90℃; for 1h;82.7%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

2-iodo-3,4,5-trimethoxy-1-methylbenzene
1432583-84-0

2-iodo-3,4,5-trimethoxy-1-methylbenzene

Conditions
ConditionsYield
With iodine; silver trifluoroacetate In chloroform at 20℃; for 3h; Inert atmosphere;98%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

5-bromo-2-methoxy-6-methyl-benzoic acid chloride
712273-62-6

5-bromo-2-methoxy-6-methyl-benzoic acid chloride

metrafenone
220899-03-6

metrafenone

Conditions
ConditionsYield
iron(III) chloride In chlorobenzene at 80℃; for 6h; Friedel Crafts Acylation;97.4%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

5-methylpyrogallol
609-25-6

5-methylpyrogallol

Conditions
ConditionsYield
With hydrogen iodide; hypophosphorous acid Heating;96%
With boron tribromide In dichloromethane at 0 - 25℃; Inert atmosphere;59%
With hydrogen iodide
With hydrogen bromide; acetic acid
With boron tribromide In dichloromethane at 0℃; for 3h;
Dichloromethyl methyl ether
4885-02-3

Dichloromethyl methyl ether

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

2,3,4-trimethoxy-6-methylbenzaldehyde
22383-85-3

2,3,4-trimethoxy-6-methylbenzaldehyde

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane at 25℃; for 2h;95%
With aluminium trichloride In tetrahydrofuran
Stage #1: 3,4,5-trimethoxytoluene With aluminum (III) chloride In dichloromethane at 0℃; for 0.75h;
Stage #2: Dichloromethyl methyl ether In dichloromethane at 0 - 20℃;
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

2,6-diiodo-3,4,5-trimethoxytoluene
115592-75-1

2,6-diiodo-3,4,5-trimethoxytoluene

Conditions
ConditionsYield
With iodine; periodic acid In acetic acid at 53℃; for 24h;93%
With iodine; periodic acid In acetic acid at 53℃; for 24h;93%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

acetic acid
64-19-7

acetic acid

A

3,4,5-trimethoxybenzyl acetate
72092-48-9

3,4,5-trimethoxybenzyl acetate

B

brittonin A
33284-74-1

brittonin A

Conditions
ConditionsYield
With nitric acid at 20℃; for 1h;A 93%
B 1%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

acetic acid
64-19-7

acetic acid

3,4,5-trimethoxybenzyl acetate
72092-48-9

3,4,5-trimethoxybenzyl acetate

Conditions
ConditionsYield
With nitric acid at 20℃; for 0.833333h;93%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

A

3,4,5-trimethoxybenzyl acetate
72092-48-9

3,4,5-trimethoxybenzyl acetate

B

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

3,4,5-trimethoxy-benzaldehyde

Conditions
ConditionsYield
With oxygen; cobalt(II) acetate; manganese(II) acetate In acetic acid at 110℃; under 2280 Torr; for 2h;A 4.2%
B 91.2%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

sodium 4-methylbenzenesulfinate
824-79-3

sodium 4-methylbenzenesulfinate

p-tolyl(2,3,4-trimethoxy-6-methylphenyl)sulfane

p-tolyl(2,3,4-trimethoxy-6-methylphenyl)sulfane

Conditions
ConditionsYield
With hydrogenchloride; 1-hexyl-3-methyl-1-imidazolium bromide In water at 80℃; for 6h; chemoselective reaction;91%
formaldehyd
50-00-0

formaldehyd

3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

2-chloromethyl-3,4,5-trimethoxytoluene
868615-18-3

2-chloromethyl-3,4,5-trimethoxytoluene

Conditions
ConditionsYield
With hydrogenchloride In water at 20 - 40℃; for 1h; Blanc Reaction;90%
With hydrogenchloride In water at 35℃; for 1h; Blanc Chloromethylation Reaction;85 %Chromat.
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

N-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)benzimidamide

N-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)benzimidamide

1,3-dimethyl-7-phenyl-5-(3,4,5-trimethoxyphenyl)pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione

1,3-dimethyl-7-phenyl-5-(3,4,5-trimethoxyphenyl)pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With tert.-butylhydroperoxide; caesium carbonate at 100℃; for 15h; Green chemistry;90%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

2-chloro-3,4,5-trimethoxytoluene

2-chloro-3,4,5-trimethoxytoluene

Conditions
ConditionsYield
With iodobenzene; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium chloride In tetrahydrofuran at 20℃; for 24h;89%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

1,3-dimethoxy-5-methylbenzene
4179-19-5

1,3-dimethoxy-5-methylbenzene

Conditions
ConditionsYield
With potassium In tetrahydrofuran for 24h; Ambient temperature;87%
With potassium In tetrahydrofuran for 24h; Ambient temperature;87%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

3-methoxy-5-methyl-1,2-benzenediol
1125-67-3

3-methoxy-5-methyl-1,2-benzenediol

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 0℃; for 0.5h;87%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

A

2,6-dibromo-3,4,5-trimethoxytoluene
1204479-24-2

2,6-dibromo-3,4,5-trimethoxytoluene

B

2-bromo-3,4,5-trimethoxy-1-methylbenzene
72326-72-8

2-bromo-3,4,5-trimethoxy-1-methylbenzene

Conditions
ConditionsYield
With bromine; sodium acetate; acetic acid In tetrachloromethane at 10 - 20℃; for 2.5h; Inert atmosphere;A 11%
B 86%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

1-bromomethyl-3-methoxybenzene
874-98-6

1-bromomethyl-3-methoxybenzene

1,2,3-trimethoxy-5-(3-methoxyphenethyl)benzene
108853-15-2

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

Conditions
ConditionsYield
Stage #1: 3,4,5-trimethoxytoluene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; potassium tert-butylate In hexane; n-heptane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: 1-bromomethyl-3-methoxybenzene In hexane; n-heptane at 0℃; for 1h; Inert atmosphere;
86%

6443-69-2Relevant articles and documents

Direct Hydrodecarboxylation of Aliphatic Carboxylic Acids: Metal- and Light-Free

Burns, David J.,Lee, Ai-Lan,McLean, Euan B.,Mooney, David T.

supporting information, p. 686 - 691 (2022/01/28)

A mild and inexpensive method for direct hydrodecarboxylation of aliphatic carboxylic acids has been developed. The reaction does not require metals, light, or catalysts, rendering the protocol operationally simple, easy to scale, and more sustainable. Crucially, no additional H atom source is required in most cases, while a broad substrate scope and functional group tolerance are observed.

Metal-Free Heterogeneous Semiconductor for Visible-Light Photocatalytic Decarboxylation of Carboxylic Acids

Shi, Jiale,Yuan, Tao,Zheng, Meifang,Wang, Xinchen

, p. 3040 - 3047 (2021/03/09)

A suitable protocol for the photocatalytic decarboxylation of carboxylic acids was developed with metal-free ceramic boron carbon nitrides (BCN). With visible light irradiation, BCN oxidize carboxylic acids to give carbon-centered radicals, which were trapped by hydrogen atom donors or employed in the construction of the carbon-carbon bond. In this system, both (hetero)aromatic and aliphatic acids proceed the decarboxylation smoothly, and C-H, C-D, and C-C bonds are formed in moderate to high yields (35 examples, yield up to 93%). Control experiments support a radical process, and isotopic experiments show that methanol is employed as the hydrogen atom donor. Recycle tests and gram-scale reaction elucidate the practicability of the heterogeneous ceramic BCN photoredox system. It provides an alternative to homogeneous catalysts in the valuable carbon radical intermediates formation. Moreover, the metal-free system is also applicable to late-stage functionalization of anti-inflammatory drugs, such as naproxen and ibuprofen, which enrich the chemical toolbox.

Hydrogenation of plant polyalkoxybenzene derivatives: convenient access to coenzyme Q0 analogues

Khrustalev, Victor N.,Muravsky, Egor A.,Semenov, Victor V.,Shinkarev, Ilia Yu.,Varakutin, Alexander E.

, p. 599 - 601 (2020/10/18)

A technologically advanced protocol has been developed for converting plant allyl(polyalkoxy)benzenes to methyl- and propyl(polyalkoxy)benzenes being intermediates in the syntheses of coenzyme Q0 analogues. The key stage of allyl and benzaldehyde moieties hydrogenation was carried out in a periodical autoclave mode on highly porous ceramic block Pd-catalysts. These catalysts possess large surface area, low hydraulic resistance, significant thermal and mechanical stabililty, multiple cycling and easy regeneration, which can dramatically reduce Pd consumption.

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