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634-36-6 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 634-36-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 4 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 634-36:
(5*6)+(4*3)+(3*4)+(2*3)+(1*6)=66
66 % 10 = 6
So 634-36-6 is a valid CAS Registry Number.
InChI:InChI=1/C9H12O3/c1-10-7-5-4-6-8(11-2)9(7)12-3/h4-6H,1-3H3

634-36-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A14572)  1,2,3-Trimethoxybenzene, 98+%   

  • 634-36-6

  • 25g

  • 333.0CNY

  • Detail
  • Alfa Aesar

  • (A14572)  1,2,3-Trimethoxybenzene, 98+%   

  • 634-36-6

  • 100g

  • 954.0CNY

  • Detail
  • Alfa Aesar

  • (A14572)  1,2,3-Trimethoxybenzene, 98+%   

  • 634-36-6

  • 500g

  • 4247.0CNY

  • Detail

634-36-6SDS

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 1,2,3-trimethoxybenzene

1.2 Other means of identification

Product number -
Other names Benzene,1,2,3-trimethoxy

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:634-36-6 SDS

634-36-6Synthetic route

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

1,3-dimethoxy-2-hydroxy-benzene

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 5h; Product distribution; Further Variations:; Temperatures; Solvents; Pressures; reaction times; microwave irradiation;99%
With N,N'-dimethylimidazolium-2-carboxylate In acetonitrile at 160℃; for 1.33333h; Microwave irradiation; Green chemistry;93%
N,N,N',N'-tetrabutyl-N''-methylguanidine at 180℃; for 4.5h;82 % Chromat.
3,4,5-trimethoxyphenyl trifluoromethanesulfonate
143287-98-3

3,4,5-trimethoxyphenyl trifluoromethanesulfonate

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With hydrogen; diethylamine; palladium on activated charcoal In methanol at 20℃; for 4h;99%
With ammonium acetate; magnesium; palladium on activated charcoal In methanol at 20℃; for 1h;89%
With methanol; magnesium; palladium on activated charcoal at 20℃; for 12h;
1-bromo-3,4,5-trimethoxybenzene
2675-79-8

1-bromo-3,4,5-trimethoxybenzene

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With potassium hydroxide; iso-butanol; palladium diacetate; triphenylphosphine at 100℃; for 1h;99%
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 3h;98%
With methanol; gold; hydrogen; caesium carbonate at 100℃; under 3800.26 Torr; for 150h;93%
dimethyl sulfate
77-78-1

dimethyl sulfate

2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
Stage #1: 2-hydroxyresorcinol With sodium hydroxide In acetone at 20℃; for 0.5h;
Stage #2: dimethyl sulfate In acetone at 20℃; for 10h;
98%
Stage #1: 2-hydroxyresorcinol With sodium hydroxide at 20℃; for 0.5h;
Stage #2: dimethyl sulfate at 20℃; for 10h;
98%
With sodium hydroxide98%
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With palladium nanoparticles supported on fibrous silica In cyclohexane at 130℃; Molecular sieve;95%
With hydrogen In tetrahydrofuran at 165℃; under 15001.5 - 26252.6 Torr; for 1.5h; Solvent; Autoclave;90.6%
With palladium diacetate In cyclohexane at 140℃; for 24h; Molecular sieve; air;68%
5-iodo-1,2,3-trimethoxybenzene
25245-29-8

5-iodo-1,2,3-trimethoxybenzene

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With 2-(2-methoxyethoxy)ethyl alcohol; oxygen; sodium hydride In 1,4-dioxane at 20℃; for 24h; Schlenk technique; chemoselective reaction;95%
With hydrogen; triethylamine In methanol; water at 120℃; under 22502.3 Torr; for 52h; Autoclave;82%
3,4,5-trimethoxybenzonitrile
1885-35-4

3,4,5-trimethoxybenzonitrile

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With lithium borohydride; C30H21F6N2NiO2P In tetrahydrofuran at 70℃; for 3h; Schlenk technique; Inert atmosphere;94%
2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

methyl iodide
74-88-4

methyl iodide

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With potassium carbonate In acetone93%
for 6h;80%
With potassium hydroxide
With potassium carbonate In acetone
(3,4,5-trimethoxyphenyl)methanol
3840-31-1

(3,4,5-trimethoxyphenyl)methanol

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With chlorobis(cyclooctene)-iridium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium chloride In water; 1,3,5-trimethyl-benzene at 170℃; for 20h; Schlenk technique; Inert atmosphere;93%
With oxygen; palladium diacetate; sodium carbonate In cyclohexane at 130℃; for 48h; Molecular sieve; Schlenk technique;86%
1-(methylsulfonyl)-2-(3,4,5-trimethoxyphenyl)diazene

1-(methylsulfonyl)-2-(3,4,5-trimethoxyphenyl)diazene

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
In water; isopropyl alcohol for 14h; Irradiation;89%
(3,4,5-methoxyphenyl)(1-oxido-2-pyridinyl)methanone

(3,4,5-methoxyphenyl)(1-oxido-2-pyridinyl)methanone

phenylboronic acid
98-80-6

phenylboronic acid

A

(1-oxido-2-pyridinyl)phenylmethanone
4789-06-4

(1-oxido-2-pyridinyl)phenylmethanone

B

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

C

2,4,6-trimethoxy-1,1’-biphenyl
64461-92-3

2,4,6-trimethoxy-1,1’-biphenyl

Conditions
ConditionsYield
With acetylacetonatodicarbonylrhodium(l); water In 1,4-dioxane at 140℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Sealed tube;A 87%
B 76%
C 8%
dimethyl sulfate
77-78-1

dimethyl sulfate

2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

A

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

1,3-dimethoxy-2-hydroxy-benzene

B

3-methocycatechol
934-00-9

3-methocycatechol

C

2,3-dimethoxyphenol
5150-42-5

2,3-dimethoxyphenol

D

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With sodium hydroxide; boric acid at 20 - 25℃; for 2h; pH 10.0 - 10.4;A n/a
B 84%
C n/a
D n/a
1,3-dimethoxy-2-hydroxy-benzene
91-10-1

1,3-dimethoxy-2-hydroxy-benzene

3-bromophenyltrimethylammonium iodide

3-bromophenyltrimethylammonium iodide

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 80℃; for 3h;83%
1-bromo-3,4,5-trimethoxybenzene
2675-79-8

1-bromo-3,4,5-trimethoxybenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

A

2-(3,4,5-trimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
214360-67-5

2-(3,4,5-trimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

B

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); 1,3-bis-(diphenylphosphino)propane; triethylamine In toluene at 100℃; for 18h; Inert atmosphere;A 79%
B n/a
With copper(l) iodide; iron(III)-acetylacetonate; N,N,N,N,-tetramethylethylenediamine; sodium hydride In tetrahydrofuran; mineral oil at -10℃; Inert atmosphere;A 55%
B n/a
1-bromo-3,4,5-trimethoxybenzene
2675-79-8

1-bromo-3,4,5-trimethoxybenzene

A

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

B

3,3’,4,4’,5,5’-hexamethoxy-1,1’-biphenyl
56772-00-0

3,3’,4,4’,5,5’-hexamethoxy-1,1’-biphenyl

Conditions
ConditionsYield
Stage #1: 1-bromo-3,4,5-trimethoxybenzene With magnesium In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
Stage #2: With synthetic air; cobalt(II) chloride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
A 20%
B 79%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

potassium 2,6-dimethoxybenzoate
16463-42-6

potassium 2,6-dimethoxybenzoate

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With oxygen; copper diacetate; silver carbonate In N,N-dimethyl-formamide at 145℃; for 18h;79%
1-bromo-3,4,5-trimethoxybenzene
2675-79-8

1-bromo-3,4,5-trimethoxybenzene

4,4,5,5-tetramethyl-2-(3-methylbut-2-enyl)-1,3,2-dioxaborolane
141550-13-2

4,4,5,5-tetramethyl-2-(3-methylbut-2-enyl)-1,3,2-dioxaborolane

A

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

B

1,2,3-trimethoxy-5-(3-methylbut-2-en-1-yl)benzene
93930-23-5

1,2,3-trimethoxy-5-(3-methylbut-2-en-1-yl)benzene

Conditions
ConditionsYield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3chloro-pyridyl)palladium(II) dichloride; potassium hydroxide In tetrahydrofuran at 70℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; regioselective reaction;A 14%
B 78%
C19H24O7

C19H24O7

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

A

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

B

methyl 3,4-dimethoxybenzoate
2150-38-1

methyl 3,4-dimethoxybenzoate

Conditions
ConditionsYield
With caesium carbonate at 180℃; for 8h; Catalytic behavior; Autoclave;A 62%
B 16%
1-iodo-2,3,4-trimethoxy-benzene
25245-37-8

1-iodo-2,3,4-trimethoxy-benzene

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine; trifluoroacetic acid In N,N-dimethyl-formamide at 55℃; for 9h;49%
1-bromo-3,4,5-trimethoxybenzene
2675-79-8

1-bromo-3,4,5-trimethoxybenzene

(E)-4-(2-bromo-vinyl)-anisole
6303-59-9, 60592-52-1, 27570-08-7

(E)-4-(2-bromo-vinyl)-anisole

A

4,4'-bis(trifluoromethyl)biphenyl
581-80-6

4,4'-bis(trifluoromethyl)biphenyl

B

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

C

1-(4-methoxyphenyl)-4-(4-methoxyphenyl)-1,3-butadiene
43212-67-5

1-(4-methoxyphenyl)-4-(4-methoxyphenyl)-1,3-butadiene

D

(E)-3,4,4',5-tetramethoxystilbene
134029-62-2

(E)-3,4,4',5-tetramethoxystilbene

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); N,N-dimethyl acetamide; silver fluoride; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc at 0 - 20℃; for 15h; Reagent/catalyst; Schlenk technique; Sealed tube; Inert atmosphere;A 40%
B 15%
C 40%
D 35%
5-iodo-1,2,3-trimethoxybenzene
25245-29-8

5-iodo-1,2,3-trimethoxybenzene

methyl 6-bromo-2,3,4-trimethoxybenzoate
80141-07-7

methyl 6-bromo-2,3,4-trimethoxybenzoate

A

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

B

3,3’,4,4’,5,5’-hexamethoxy-1,1’-biphenyl
56772-00-0

3,3’,4,4’,5,5’-hexamethoxy-1,1’-biphenyl

C

4,5,6,4',5',6'-Hexamethoxy-biphenyl-2,2'-dicarboxylic acid dimethyl ester
4891-62-7, 65995-60-0, 71307-89-6

4,5,6,4',5',6'-Hexamethoxy-biphenyl-2,2'-dicarboxylic acid dimethyl ester

D

methyl 3',4,4',5,5',6-hexamethoxybiphenyl-2-carboxylate
80141-09-9

methyl 3',4,4',5,5',6-hexamethoxybiphenyl-2-carboxylate

Conditions
ConditionsYield
With copper bronze 1.) 240 deg C, 0.5 h, 2.) from 240 deg C to 280 deg C, 0.5 h; Further byproducts given;A 15%
B 28%
C 8%
D 39%
3,4,5-trimethoxy-benzenesulfonic acid
42771-33-5

3,4,5-trimethoxy-benzenesulfonic acid

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
Erhitzen in Loesung;
3,4,5-trimethoxy-benzoic acid ; calcium salt

3,4,5-trimethoxy-benzoic acid ; calcium salt

A

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

B

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
bei der trocknen Destillation;
2,3-dimethoxyphenol
5150-42-5

2,3-dimethoxyphenol

methyl iodide
74-88-4

methyl iodide

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With potassium hydroxide
3-methocycatechol
934-00-9

3-methocycatechol

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
at 25℃; for 336h; Aspergillus repens MA0197;
2,3-dimethoxyphenol
5150-42-5

2,3-dimethoxyphenol

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
Aspergillus repens MA0197; Yield given;
Carbonic acid 2,6-dimethoxy-phenyl ester methyl ester
114591-58-1

Carbonic acid 2,6-dimethoxy-phenyl ester methyl ester

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
dmap at 110℃; for 4h;92 % Chromat.
3-methocycatechol
934-00-9

3-methocycatechol

dimethyl sulfate
77-78-1

dimethyl sulfate

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With potassium carbonate In acetone26 mg
2,3,4-trimethoxyphenylboronic acid
118062-05-8

2,3,4-trimethoxyphenylboronic acid

A

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

B

2,3,4-trimethoxy-1-(2',3',4'-trimethoxyphenyl)benzene
6322-17-4

2,3,4-trimethoxy-1-(2',3',4'-trimethoxyphenyl)benzene

Conditions
ConditionsYield
With air; sodium carbonate; palladium diacetate In ethanol for 72h; Ambient temperature;A 42 % Chromat.
B 58 % Chromat.
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

1-iodo-2,3,4-trimethoxy-benzene
25245-37-8

1-iodo-2,3,4-trimethoxy-benzene

Conditions
ConditionsYield
With N-iodo-succinimide; trifluoroacetic acid In acetonitrile at 20℃; for 1.5h;100%
With N-iodo-succinimide In various solvent(s) at 27℃; for 0.25h;95%
With N-iodo-succinimide; trifluoroacetic acid In acetonitrile at 20℃;91%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

2,3,4-trimethoxybromobenzene
10385-36-1

2,3,4-trimethoxybromobenzene

Conditions
ConditionsYield
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 2h; Heating;100%
With pyridinium hydrobromide perbromide In acetic anhydride at 50 - 55℃; for 0.25h;99%
With N-Bromosuccinimide; C5H13NO3S In n-heptane at 25℃; for 14.5h; Darkness;99%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

C9H10(2)H2O3

C9H10(2)H2O3

Conditions
ConditionsYield
With perchloric acid; d(4)-methanol at 75℃; for 72h; Inert atmosphere;100%
2-acetoxyimino-3-oxo-butyric acid ethyl ester
6267-89-6

2-acetoxyimino-3-oxo-butyric acid ethyl ester

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

2',3',4'-trimethoxyacetophenone
13909-73-4

2',3',4'-trimethoxyacetophenone

Conditions
ConditionsYield
With PPA Ambient temperature;99%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

C13H13NO5

C13H13NO5

2,3,4-trimethoxybenzophenone
94709-11-2

2,3,4-trimethoxybenzophenone

Conditions
ConditionsYield
With PPA Ambient temperature;99%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-(3,4,5-trimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
214360-67-5

2-(3,4,5-trimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
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 8h; Schlenk technique; Inert atmosphere;99%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1-(4,4'-di-tert-butyl-[2,2'-bipyridin]-6-yl)-2-(dimethyl(phenyl)silyl)-2,3-dihydro-1H-benzo[d][1,3,2]diazaborole Inert atmosphere; Schlenk technique; Sealed tube;99%
Stage #1: bis(pinacol)diborane With C24H28ClIrN2O In n-heptane; isopropyl alcohol at 75℃; for 1h; Sealed tube; Inert atmosphere;
Stage #2: 1,2,3-trimethoxybenzene In n-heptane; isopropyl alcohol Sealed tube; Inert atmosphere;
99%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

1,2,3-trimethoxy-4-chlorobenzene
54625-53-5

1,2,3-trimethoxy-4-chlorobenzene

Conditions
ConditionsYield
With kaolin; sodium chlorite; manganese(III) acetylacetonate In dichloromethane at 25℃; for 1.33333h;98%
With N-chloro-succinimide In various solvent(s) at 27℃; for 0.5h;90%
With aluminum oxide; sodium chlorite; (salen)Mn(III) In dichloromethane at 20℃; for 0.833333h;89%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

1,5-dibromo-2,3,4-trimethoxybenzene
92670-09-2

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

Conditions
ConditionsYield
With 1,3-dibromo-5,5-dimethoxyhydantoin In tetrahydrofuran at 0 - 20℃; for 18h;98%
With bromine In dichloromethane at 0 - 25℃; for 12h;81%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In tetrahydrofuran at 20℃; for 24h;72%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

acetic acid
64-19-7

acetic acid

pyrogallol triacetate
525-52-0

pyrogallol triacetate

Conditions
ConditionsYield
Stage #1: 1,2,3-trimethoxybenzene With boron tribromide In dichloromethane at 0 - 20℃; Inert atmosphere;
Stage #2: acetic acid In dichloromethane at 0 - 20℃; Inert atmosphere;
98%
4-azidobutanoyl chloride
14468-88-3

4-azidobutanoyl chloride

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

C13H17NO4
1415414-00-4

C13H17NO4

Conditions
ConditionsYield
Stage #1: 4-azidobutanoyl chloride; 1,2,3-trimethoxybenzene In dichloromethane at 20℃; for 0.166667h;
Stage #2: With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.333333h;
98%
Stage #1: 4-azidobutanoyl chloride; 1,2,3-trimethoxybenzene In dichloromethane at 20℃; for 0.166667h;
Stage #2: With ethylaluminum dichloride In dichloromethane at 20℃; for 0.333333h;
98%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

5-azidopentanoic chloride
79583-99-6

5-azidopentanoic chloride

C14H19NO4
1415414-02-6

C14H19NO4

Conditions
ConditionsYield
Stage #1: 1,2,3-trimethoxybenzene; 5-azidopentanoyl chloride In dichloromethane at 20℃; for 0.166667h;
Stage #2: With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.333333h;
97%
Stage #1: 1,2,3-trimethoxybenzene; 5-azidopentanoyl chloride In dichloromethane at 20℃; for 0.166667h;
Stage #2: With ethylaluminum dichloride In dichloromethane at 20℃; for 0.333333h;
97%
4-Methoxybenzenethiol
696-63-9

4-Methoxybenzenethiol

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

1,2,3-trimethoxy-5-[(4-methoxyphenyl)thio]benzene
1160839-21-3

1,2,3-trimethoxy-5-[(4-methoxyphenyl)thio]benzene

Conditions
ConditionsYield
With tetrabutylammonium acetate for 4.5h; Electrolysis; Inert atmosphere; Sealed tube; regioselective reaction;97%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

benzoyl chloride
98-88-4

benzoyl chloride

(3,4-dimethoxy-2-hydroxyphenyl)(phenyl)methanone
7508-32-9

(3,4-dimethoxy-2-hydroxyphenyl)(phenyl)methanone

Conditions
ConditionsYield
With aluminium trichloride In 1,2-dichloro-ethane 1.) from 0 deg C to RT, 3 h, 2.) reflux, 1 h;96%
With zinc(II) chloride
With aluminum (III) chloride In 1,2-dichloro-ethane at 0 - 5℃; for 5h; Heating / reflux;
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

chromium(0) hexacarbonyl
199620-14-9, 13007-92-6

chromium(0) hexacarbonyl

tricarbonyl(η(6)-1,2,3-trimethoxybenzene)chromium
12193-72-5

tricarbonyl(η(6)-1,2,3-trimethoxybenzene)chromium

Conditions
ConditionsYield
In tetrahydrofuran; dibutyl ether N2-atmosphere, protecting from light; excess arene, refluxing in THF/Bu2O=1:9 v/v for 5 d; filtration (Celite), evapn. (reduced pressure), chromy. (SiO2); elem. anal.;96%
boiling;;
boiling;;
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

(2-iodo-4,5-dimethoxyphenyl)acetic acid
35323-09-2

(2-iodo-4,5-dimethoxyphenyl)acetic acid

2-(2-iodo-4,5-dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethanone
175293-60-4

2-(2-iodo-4,5-dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethanone

Conditions
ConditionsYield
Stage #1: (2-iodo-4,5-dimethoxyphenyl)acetic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere; Cooling;
Stage #2: 1,2,3-trimethoxybenzene With aluminum (III) chloride In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere; Cooling;
96%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

Conditions
ConditionsYield
With aluminium(III) iodide; tetra-(n-butyl)ammonium iodide In benzene for 0.5h; Heating;95%
With aluminum (III) chloride In chloroform for 4h; Solvent; Reflux;80%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

2-Fluorobenzoyl chloride
393-52-2

2-Fluorobenzoyl chloride

(2-Fluoro-phenyl)-(2-hydroxy-3,4-dimethoxy-phenyl)-methanone
140665-37-8

(2-Fluoro-phenyl)-(2-hydroxy-3,4-dimethoxy-phenyl)-methanone

Conditions
ConditionsYield
With aluminium trichloride In 1,2-dichloro-ethane 1.) from 0 deg C to RT, 3 h, 2.) reflux, 1 h;95%
silver tetrafluoroborate
14104-20-2

silver tetrafluoroborate

bromopentacarbonylmanganese(I)
14516-54-2

bromopentacarbonylmanganese(I)

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

(η(6)-1,2,3-trimethoxybenzene)manganesetricarbonyl tetrafluoroborate
180037-52-9

(η(6)-1,2,3-trimethoxybenzene)manganesetricarbonyl tetrafluoroborate

Conditions
ConditionsYield
In dichloromethane tratment of Mn-complex with AgBF4, then with C6H3(OMe)3;95%
Diphenylmethane
101-81-5

Diphenylmethane

1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

C35H32O3
1169764-39-9

C35H32O3

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; iron(II) chloride at 100℃; for 36h; Inert atmosphere;95%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

p-Chlorothiophenol
106-54-7

p-Chlorothiophenol

(4-chlorophenyl)(2,3,4-trimethoxyphenyl)sulfane

(4-chlorophenyl)(2,3,4-trimethoxyphenyl)sulfane

Conditions
ConditionsYield
With di-tert-butyl peroxide; iodine at 120℃; for 24h; Schlenk technique; Inert atmosphere;95%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

C10H13NO5

C10H13NO5

cyclopropyl 2,3,4-trimethoxyphenone

cyclopropyl 2,3,4-trimethoxyphenone

Conditions
ConditionsYield
With PPA Ambient temperature;94%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

C11H15NO7

C11H15NO7

A

2',3',4'-trimethoxyacetophenone
13909-73-4

2',3',4'-trimethoxyacetophenone

B

ethyl 3-oxo-3-(2',3',4'-trimethoxyphenyl)propanoate
38975-83-6

ethyl 3-oxo-3-(2',3',4'-trimethoxyphenyl)propanoate

Conditions
ConditionsYield
With PPA Ambient temperature;A 94%
B 1.5%
1,2,3-trimethoxybenzene
634-36-6

1,2,3-trimethoxybenzene

Veratric acid
93-07-2

Veratric acid

(3,4-dimethoxyphenyl)(2,3,4-trimethoxyphenyl)methanone
1309379-60-9

(3,4-dimethoxyphenyl)(2,3,4-trimethoxyphenyl)methanone

Conditions
ConditionsYield
With polyphosphoric acid at 80℃; for 1.5h;94%
With polyphosphoric acid at 80℃; for 1.5h;94%
With polyphosphoric acid

634-36-6Relevant articles and documents

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.

Trialkylammonium salt degradation: Implications for methylation and cross-coupling

Assante, Michele,Baillie, Sharon E.,Juba, Vanessa,Leach, Andrew G.,McKinney, David,Reid, Marc,Washington, Jack B.,Yan, Chunhui

, p. 6949 - 6963 (2021/06/02)

Trialkylammonium (most notably N,N,N-trimethylanilinium) salts are known to display dual reactivity through both the aryl group and the N-methyl groups. These salts have thus been widely applied in cross-coupling, aryl etherification, fluorine radiolabelling, phase-transfer catalysis, supramolecular recognition, polymer design, and (more recently) methylation. However, their application as electrophilic methylating reagents remains somewhat underexplored, and an understanding of their arylation versus methylation reactivities is lacking. This study presents a mechanistic degradation analysis of N,N,N-trimethylanilinium salts and highlights the implications for synthetic applications of this important class of salts. Kinetic degradation studies, in both solid and solution phases, have delivered insights into the physical and chemical parameters affecting anilinium salt stability. 1H NMR kinetic analysis of salt degradation has evidenced thermal degradation to methyl iodide and the parent aniline, consistent with a closed-shell SN2-centred degradative pathway, and methyl iodide being the key reactive species in applied methylation procedures. Furthermore, the effect of halide and non-nucleophilic counterions on salt degradation has been investigated, along with deuterium isotope and solvent effects. New mechanistic insights have enabled the investigation of the use of trimethylanilinium salts in O-methylation and in improved cross-coupling strategies. Finally, detailed computational studies have helped highlight limitations in the current state-of-the-art of solvation modelling of reaction in which the bulk medium undergoes experimentally observable changes over the reaction timecourse. This journal is

Ceramic boron carbonitrides for unlocking organic halides with visible light

Yuan, Tao,Zheng, Meifang,Antonietti, Markus,Wang, Xinchen

, p. 6323 - 6332 (2021/05/19)

Photochemistry provides a sustainable pathway for organic transformations by inducing radical intermediates from substrates through electron transfer process. However, progress is limited by heterogeneous photocatalysts that are required to be efficient, stable, and inexpensive for long-term operation with easy recyclability and product separation. Here, we report that boron carbonitride (BCN) ceramics are such a system and can reduce organic halides, including (het)aryl and alkyl halides, with visible light irradiation. Cross-coupling of halides to afford new C-H, C-C, and C-S bonds can proceed at ambient reaction conditions. Hydrogen, (het)aryl, and sulfonyl groups were introduced into the arenes and heteroarenes at the designed positions by means of mesolytic C-X (carbon-halogen) bond cleavage in the absence of any metal-based catalysts or ligands. BCN can be used not only for half reactions, like reduction reactions with a sacrificial agent, but also redox reactions through oxidative and reductive interfacial electron transfer. The BCN photocatalyst shows tolerance to different substituents and conserved activity after five recycles. The apparent metal-free system opens new opportunities for a wide range of organic catalysts using light energy and sustainable materials, which are metal-free, inexpensive and stable. This journal is

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