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High purity Guaiacol 98% TOP1 supplier in China
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No Data 100 Gram 100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
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90-05-1 Usage

Purification Methods

Crystallise guaiacol from *benzene/pet ether or distil it in a vacuum. [Beilstein 6 H 768, 6 IV 5563.]

Toxicity

LD50:900 mg / kg (rat, subcutaneous).
LD50: 3.7 mg / kg (rabbit, intravenously).
Oral administration of large amount can stimulate the esophagus and stomach, resulting in heart failure, collapse and death.

Preparative methods

It can be obtained by diazotization and hydrolysis of anthranium anisole.
Obtained from fractionated of wood oil.
In the nature of guaiacol is presented in the guaiacum or pine oil. In the creosote oil obtained from wood dry distillation, guaiacol is the major ingredient. This product could be obtained through fractional distillation of creosote oil. Japan Osaka Refining Company takes o-nitrochlorobenzene as raw material, first synthesizes o-nitroanisole, and then reduces it to o-anisidine, and finally obtains the goods. China's production method is roughly the same. Ingredient consumption quota: 1250 kg / t of amino-containing anisole, 1500 kg / t of sulfuric acid (93%), 700 kg / t of sodium nitrite and 400 kg / t of copper sulfate.

Definition

ChEBI: A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.

Uses

A phenolic natural product and reducing co-substrate for COX reactions.

General Description

Colorless to amber crystals or liquid. Density (of solid) 1.129 g / cm3. Solidifies at 28°C (82.4°F), but may remain liquid for a long time even at a much lower temperature. Slightly water soluble . Soluble in aqueous sodium hydroxide. Used medicinally as an expectorant. Used, because of its anti-oxidant properties, as an anti-skinning agent for paints.

Application

Used for pharmaceuticals, dyes and spices intermediates
Mainly used for the preparation of coffee, vanilla, fumigation and tobacco flavor.
Used for the synthesis of dyes, also used as analytical reagents
In medicine, it can be used for the manufacture of calcium guaiacol sulfonate; in the spice industry, it is used the manufacture of vanillin and artificial musk; Used for test copper, hydrocyanic acid and nitrite

Reactivity Profile

Guaiacol may react with oxidizing materials. Guaiacol forms salts readily with bases.

Air & Water Reactions

Sensitive to air and light (darkens). Slightly water soluble.

Chemical properties

It appears as white or slightly yellow crystals or colorless to pale yellow transparent oily liquid. It has a special aromatic smell. It is slightly soluble in water and benzene. It is easily soluble in glycerol. It is miscible with ethanol, ether, chloroform, oil and glacier acetic acid.

Fire Hazard

Guaiacol is combustible.

Chemical Properties

Light Yellow Oil

Uses

expectorant
InChI:InChI=1/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3

90-05-1 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
USP (1300004)  Guaiacol  United States Pharmacopeia (USP) Reference Standard 90-05-1 1300004-1G 4,326.66CNY Detail
Sigma-Aldrich (Y0000619)  Guaiacol  European Pharmacopoeia (EP) Reference Standard 90-05-1 Y0000619 1,880.19CNY Detail
Sigma-Aldrich (PHR1136)  Guaiacol  pharmaceutical secondary standard; traceable to USP and PhEur 90-05-1 PHR1136-1.5G 732.19CNY Detail
Alfa Aesar (A16319)  2-Methoxyphenol, 98+%    90-05-1 5000g 3165.0CNY Detail
Alfa Aesar (A16319)  2-Methoxyphenol, 98+%    90-05-1 1000g 801.0CNY Detail
Alfa Aesar (A16319)  2-Methoxyphenol, 98+%    90-05-1 250g 317.0CNY Detail
TCI America (M0121)  Guaiacol  >98.0%(GC) 90-05-1 500g 442.00CNY Detail
TCI America (M0121)  Guaiacol  >98.0%(GC) 90-05-1 25g 124.00CNY Detail

90-05-1SDS

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 guaiacol

1.2 Other means of identification

Product number -
Other names Guaiacol

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:90-05-1 SDS

90-05-1Synthetic route

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
19513-80-5

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With formic acid; N-ethyl-N,N-diisopropylamine; Lumogen F Orange 240 In acetonitrile at 25℃; for 8h; Reagent/catalyst; UV-irradiation; Inert atmosphere;A 99%
B 99%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In ethanol at 20℃; Irradiation; chemoselective reaction;A 95%
B 72%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; Reagent/catalyst; Irradiation; chemoselective reaction;A 89%
B 88%
4-iodoanisol
529-28-2

4-iodoanisol

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With glycolic Acid; copper hydroxide; sodium hydroxide In water; dimethyl sulfoxide at 120℃; for 6h; Inert atmosphere; Schlenk technique;95%
Stage #1: 4-iodoanisol With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In water; dimethyl sulfoxide at 20 - 100℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; Inert atmosphere;
94%
Stage #1: 4-iodoanisol With copper(l) iodide; 2-methyl-8-quinolinol; tetra(n-butyl)ammonium hydroxide In water; dimethyl sulfoxide at 100℃; for 10h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃;
94%
2-bromoanisole
578-57-4

2-bromoanisole

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere;88%
Stage #1: 2-bromoanisole With copper(l) iodide; cesium hydroxide; 5-bromo-2-(1H-imidazol-2-yl)pyridine In water; dimethyl sulfoxide; tert-butyl alcohol at 120℃; for 36h; Inert atmosphere;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide; tert-butyl alcohol pH=1 - 2; Inert atmosphere;
83%
With tert.-butylhydroperoxide; n-butyllithium In tetrahydrofuran; hexane at 20℃; for 2h;78%
2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-ol

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-ol

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
ConditionsYield
With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 1h;A 95%
B 99%
With 5%-palladium/activated carbon; ammonium formate In water at 80℃; for 1h;A n/a
B 98%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere;A 89%
B 86%
2-methoxyphenoxy-3',4'-dimethoxyacetophenone
22675-96-3

2-methoxyphenoxy-3',4'-dimethoxyacetophenone

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

Veratric acid
93-07-2

Veratric acid

Conditions
ConditionsYield
With oxygen; copper(II) nitrate In acetonitrile at 120℃; under 4500.45 Torr; for 10h;A n/a
B 99%
With sodium hydroxide for 2h; Reagent/catalyst; Time; Milling; Green chemistry;A 95 %Chromat.
B 80 %Chromat.
1-(4-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
92409-23-9

1-(4-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

3-hydroxy-1-(4-methoxyphenyl)-1-propan-1-one

3-hydroxy-1-(4-methoxyphenyl)-1-propan-1-one

Conditions
ConditionsYield
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; Irradiation; Flow reactor; chemoselective reaction;A 94%
B 93%
With formic acid; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;A 82%
B 90%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 15h; Irradiation; chemoselective reaction;A 88%
B 85%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In ethanol at 20℃; Irradiation; chemoselective reaction;A 56%
B 34%
With formic acid; 10-phenyl-10H-phenothiazine; N-ethyl-N,N-diisopropylamine In acetone at 20℃; for 96h; Inert atmosphere; Irradiation;A 28 mg
B 42 mg
1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
10548-77-3

1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one

A

1-(3,4-dimethoxyphenyl)-3-hydroxypropan-1-one
104397-78-6

1-(3,4-dimethoxyphenyl)-3-hydroxypropan-1-one

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With formic acid; N-ethyl-N,N-diisopropylamine; Lumogen F Orange 240 In acetonitrile at 25℃; for 8h; Reagent/catalyst; UV-irradiation; Inert atmosphere;A 98%
B 97%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 48h; Irradiation; chemoselective reaction;A 90%
B 95%
With formic acid; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;A 90%
B 80%
1-(benzyloxy)-2-methoxybenzene
835-79-0

1-(benzyloxy)-2-methoxybenzene

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 25℃; for 3h; Inert atmosphere;96%
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 50℃; for 5h; Inert atmosphere;96%
With sulfosuccinic acid functionalized mesoporous silica In ethanol at 100℃;
1-(4-Hydroxyphenyl)-2-(2-methoxyphenoxy)-1-ethanol
106534-23-0

1-(4-Hydroxyphenyl)-2-(2-methoxyphenoxy)-1-ethanol

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

Conditions
ConditionsYield
With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 4h;A n/a
B 97%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere;A 90%
B 76%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; Green chemistry;A 90%
B 76%
With C22H17Cl3N3ORh; sodium hydroxide In water for 60h; Inert atmosphere;
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol
7382-68-5

1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
ConditionsYield
With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 14h;A n/a
B 96%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere;A 86%
B 82%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; Green chemistry;A 86%
B 82%
With C22H17Cl3N3ORh; sodium hydroxide In water for 60h; Inert atmosphere;
1-methoxy-2-(methoxymethoxy)benzene
73220-26-5

1-methoxy-2-(methoxymethoxy)benzene

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With β‐cyclodextrin In water; acetone at 60℃; for 5.5h; Green chemistry;95%
With Montmorillonite K 10 In benzene at 50℃; for 1h;91%
With bismuth(III) chloride In water; acetonitrile at 50℃; for 1h; chemoselective reaction;83%
1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
10548-77-3

1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

Veratric acid
93-07-2

Veratric acid

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; methanol; water at 50℃; for 10h;A 45%
B 88%
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; methanol at 50℃; for 10h;
With sodium hydroxide for 2h; Milling; Green chemistry;A 92 %Chromat.
B 70 %Chromat.
2-hydroxyphenyl boronic acid
89466-08-0

2-hydroxyphenyl boronic acid

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 48h; UV-irradiation;69%
2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
19513-80-5

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
ConditionsYield
With oxygen; copper(II) nitrate In acetonitrile at 120℃; under 4500.45 Torr; for 10h;A n/a
B 99%
With oxygen; copper diacetate; triethylamine In dimethyl sulfoxide at 20℃; for 12h; Sealed tube;A 93%
B 83%
With water; oxalic acid at 100℃; for 24h; Reagent/catalyst;A 21 mg
B 73%
vanillin
121-33-5

vanillin

A

2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With Ru/CNT; hydrogen In water; decalin at 200℃; under 7500.75 Torr; for 3h;
With hydrogen In water; decalin at 200℃; under 7500.75 Torr; for 6h; chemoselective reaction;
With formic acid In water at 130℃; for 6h; Reagent/catalyst; Green chemistry;A 69 %Chromat.
B 17 %Chromat.
2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;95%
3-methoxy-4-hydroxybenzoic acid
121-34-6

3-methoxy-4-hydroxybenzoic acid

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With cucumber juice at 30 - 35℃; for 48h; Inert atmosphere; Green chemistry;80%
With copper dichloride In water at 200℃; for 6h; Inert atmosphere; Autoclave;55%
decarboxylase
decarboxylase Enzymatic reaction;
With hydrogen In water at 170℃; under 7500.75 Torr; for 4h; Autoclave;
1-(benzyloxy)-2-methoxybenzene
835-79-0

1-(benzyloxy)-2-methoxybenzene

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

toluene
108-88-3

toluene

Conditions
ConditionsYield
With Ni7Au3; hydrogen In water at 130℃; under 7500.75 Torr; for 0.5h; Reagent/catalyst;A 44%
B 14%
With hydrogen In water at 60℃; under 7500.75 Torr; for 1h; Reagent/catalyst; Overall yield = 60 %Chromat.;
2-methoxyphenyl benzenesulfonate
3900-91-2

2-methoxyphenyl benzenesulfonate

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With potassium hydroxide In toluene; tert-butyl alcohol at 100℃; for 0.5h; Inert atmosphere;87%
2-Chloroanisole
766-51-8

2-Chloroanisole

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
Stage #1: 2-Chloroanisole With tris-(dibenzylideneacetone)dipalladium(0); cesium hydroxide monohydrate; 2-((di-adamantan-1-yl)phosphaneyl)-1-(2,6-diisopropylphenyl)-1H-imidazole In 1,4-dioxane at 120℃; for 20h; Inert atmosphere;
Stage #2: With hydrogenchloride In 1,4-dioxane; water at 20℃; Inert atmosphere;
90%
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; water at 100℃; for 24h;79%
With trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II); C29H45Pt; potassium carbonate In water; N,N-dimethyl-formamide at 115℃; for 0.5h; Inert atmosphere; Microwave irradiation;60%
C20H24O6

C20H24O6

A

3-(3,4-dimethoxyphenyl)-1-propanol
3929-47-3

3-(3,4-dimethoxyphenyl)-1-propanol

B

4-propyl-1,2-dimethoxybenzene
5888-52-8

4-propyl-1,2-dimethoxybenzene

C

Acetic acid 3-(3,4-dimethoxy-phenyl)-propyl ester
100699-21-6

Acetic acid 3-(3,4-dimethoxy-phenyl)-propyl ester

D

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,2-dichloro-ethane at 140℃; under 31029.7 Torr; for 16h;A 18%
B 32%
C 19%
D 69%
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,1,2,2-tetrachloroethane at 140℃; under 31029.7 Torr; for 2h;A 14%
B 7%
C 34%
D 59%
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,2-dichloro-ethane at 140℃; under 31029.7 Torr; for 16h;A 6%
B 11%
C 19%
D 56%
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,2-dichloro-ethane at 140℃; under 31029.7 Torr; for 16h;A 9%
B 17%
C 9%
D 43%
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,2-dichloro-ethane at 140℃; under 31029.7 Torr; for 16h;A 22%
B 12%
C 13%
D 13%
2-(2,6-dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)ethan-1-one
29389-04-6

2-(2,6-dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)ethan-1-one

A

β-oxo-β-(3,4-dimethoxyphenyl)-ethanol
37803-48-8

β-oxo-β-(3,4-dimethoxyphenyl)-ethanol

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; copper diacetate In methanol at 80℃; under 3000.3 Torr; for 3h;A 93%
B 21%
2-(2-methoxyphenoxy)-acetophenone
14385-48-9

2-(2-methoxyphenoxy)-acetophenone

A

1-phenyl-2-hydroxyethanone
582-24-1

1-phenyl-2-hydroxyethanone

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; copper diacetate In methanol at 80℃; under 3000.3 Torr; for 3h;A 95%
B 27%
2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
19513-80-5

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one

A

p-methoxybenzoylmethanol
4136-21-4

p-methoxybenzoylmethanol

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; copper diacetate In methanol at 80℃; under 3000.3 Torr; for 3h;A 85%
B 10%
C18H22O6

C18H22O6

A

2-methoxy-phenol
90-05-1

2-methoxy-phenol

B

1-(3,4-dimethoxyphenyl)ethanone
1131-62-0

1-(3,4-dimethoxyphenyl)ethanone

Conditions
ConditionsYield
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 48h; Inert atmosphere;A 90%
B 85%
2-(2-methoxyphenoxy)-acetophenone
14385-48-9

2-(2-methoxyphenoxy)-acetophenone

di-n-propylamine
142-84-7

di-n-propylamine

A

N,N-dipropylbenzamide
14657-86-4

N,N-dipropylbenzamide

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With copper diacetate In dimethyl sulfoxide at 20℃; for 10h; Sealed tube;A 81%
B 91%
With copper(II) acetate monohydrate In dimethyl sulfoxide at 25℃; under 760.051 Torr; for 12h;A 46 %Chromat.
B 94 %Chromat.
2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
19513-80-5

2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one

dimethyl amine
124-40-3

dimethyl amine

A

N,N-dimethyl-4-methoxybenzamide
7291-00-1

N,N-dimethyl-4-methoxybenzamide

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With copper diacetate In water; dimethyl sulfoxide at 20℃; for 12h; Sealed tube;A 78%
B 87%
With copper(II) acetate monohydrate In dimethyl sulfoxide at 25℃; under 760.051 Torr; for 9h;A 67 %Chromat.
B 86 %Chromat.
2-methoxyphenoxy-3',4'-dimethoxyacetophenone
22675-96-3

2-methoxyphenoxy-3',4'-dimethoxyacetophenone

dimethyl amine
124-40-3

dimethyl amine

A

3,4-dimethoxy-N,N-dimethylbenzamide
6967-45-9

3,4-dimethoxy-N,N-dimethylbenzamide

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With copper diacetate In water; dimethyl sulfoxide at 20℃; for 12h; Sealed tube;A 80%
B 76%
With copper(II) acetate monohydrate In dimethyl sulfoxide at 25℃; under 760.051 Torr; for 9h;A 80 %Chromat.
B 75 %Chromat.
4-bromoguaiacol
7368-78-7

4-bromoguaiacol

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
Stage #1: 4-bromoguaiacol With nickel(II) iodide; 1,4-bis(dicyclohexylphosphino)butane; sodium carbonate; cesium iodide In tetrahydrofuran for 0.25h; Schlenk technique; Glovebox;
Stage #2: In tetrahydrofuran at 35℃; for 72h; Irradiation;
76%
2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

2-methoxy-phenol
90-05-1

2-methoxy-phenol

Conditions
ConditionsYield
With hydrazine hydrate; caesium carbonate at 80℃; for 8h;99%
With water; dihydrogen peroxide at 20℃; for 0.166667h; Green chemistry;97%
With water; caesium carbonate; hydrazine hydrate at 80℃; for 24h;97%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

allyl bromide
106-95-6

allyl bromide

O-allyl guaiacol
4125-43-3

O-allyl guaiacol

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; Reflux;100%
With potassium carbonate; potassium iodide In acetone for 18h; Reflux;100%
With potassium carbonate99%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

4-bromoguaiacol
7368-78-7

4-bromoguaiacol

Conditions
ConditionsYield
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 4h; Heating;100%
With bromine In dichloromethane at -78 - -5℃; for 1h; Inert atmosphere;100%
With bromine In dichloromethane97%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-methoxyphenyl mesylate
98910-57-7

2-methoxyphenyl mesylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 2h; Inert atmosphere;100%
With triethylamine In ethyl acetate at 0 - 20℃; for 0.166667h; Green chemistry;97%
With triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;97%
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

2-methoxy-phenol
90-05-1

2-methoxy-phenol

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

1-methoxy-2-(methoxymethoxy)benzene

Conditions
ConditionsYield
Stage #1: 2-methoxy-phenol With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: chloromethyl methyl ether In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 5h;
100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;99%
With N-ethyl-N,N-diisopropylamine at 0 - 20℃;99%
triethyl orthoacrylate
42216-96-6

triethyl orthoacrylate

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2,2-diethoxy-8-methoxychroman
80515-77-1

2,2-diethoxy-8-methoxychroman

Conditions
ConditionsYield
With Trimethylacetic acid In toluene for 20h; Heating;100%
methanol
67-56-1

methanol

2-methoxy-phenol
90-05-1

2-methoxy-phenol

(+/-)-(1R,2R,7R,8S)-3,3,10,10-tetramethoxytricyclo[6.2.2.02,7]dodeca-5,11-diene-4,9-dione

(+/-)-(1R,2R,7R,8S)-3,3,10,10-tetramethoxytricyclo[6.2.2.02,7]dodeca-5,11-diene-4,9-dione

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene at 20℃;100%
With iodobenzene; 3-chloro-benzenecarboperoxoic acid at 25℃; for 0.166667h; Reagent/catalyst; Diels-Alder Cycloaddition;95%
With [bis(acetoxy)iodo]benzene at 0 - 20℃; for 1.5h;94%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

benzenesulfonyl chloride
1939-99-7

benzenesulfonyl chloride

benzylsulfonylguaiacol
597581-23-2

benzylsulfonylguaiacol

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran100%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

5-iodo-2-methoxyphenol
160257-85-2

5-iodo-2-methoxyphenol

Conditions
ConditionsYield
With iodine; n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 2h; Heating;100%
Multi-step reaction with 3 steps
1: 99 percent / pyridine / CH2Cl2 / 24 h / 0 - 18 °C
2: 73 percent / silver trifluoroacetate; iodine / CHCl3 / 5 h / 0 - 18 °C
3: 99 percent / potassium carbonate / methanol / 16 h / 18 °C
View Scheme
Multi-step reaction with 3 steps
1: 97 percent / DMAP; pyridine / CH2Cl2 / 1 h / 0 °C
2: ICl / CH2Cl2 / 168 h / 25 °C
3: 17.14 g / LiOH*H2O / methanol; tetrahydrofuran; H2O / 120 h / 25 °C
View Scheme
2-methoxy-phenol
90-05-1

2-methoxy-phenol

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

2-methoxyphenyl 4'-nitrophenyl ether
32795-85-0

2-methoxyphenyl 4'-nitrophenyl ether

Conditions
ConditionsYield
100%
With potassium carbonate In acetonitrile Heating;
With potassium carbonate In N,N-dimethyl-formamide for 8h; Inert atmosphere; Heating;
With potassium carbonate In N,N-dimethyl-formamide at 120℃;
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-methoxyphenyl triflate
59099-58-0

2-methoxyphenyl triflate

Conditions
ConditionsYield
With pyridine at 0 - 20℃; for 2h;100%
With pyridine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;98%
With pyridine In dichloromethane at 20℃; for 0.5h;96%
(S,S)-1-chloro-2,5-trans-diphenylphospholane
934421-88-2

(S,S)-1-chloro-2,5-trans-diphenylphospholane

2-methoxy-phenol
90-05-1

2-methoxy-phenol

(S,S)-1-(o-methoxyphenoxy)-2,5-trans-diphenylphospholane

(S,S)-1-(o-methoxyphenoxy)-2,5-trans-diphenylphospholane

Conditions
ConditionsYield
With lithium In diethyl ether at 20℃; for 3h;100%
2-Iodobenzyl bromide
40400-13-3

2-Iodobenzyl bromide

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-(2-iodobenzyloxy)-1-methoxybenzene
1332326-21-2

2-(2-iodobenzyloxy)-1-methoxybenzene

Conditions
ConditionsYield
With potassium carbonate In acetone at 50℃;100%
bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

2-methoxy-phenol
90-05-1

2-methoxy-phenol

methyl (2-methoxyphenoxy) ethanoate
38768-62-6

methyl (2-methoxyphenoxy) ethanoate

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 16h;100%
With potassium carbonate In acetone at 70℃; for 2h;34%
With potassium carbonate In tetrahydrofuran at 20 - 80℃;
2-methoxy-phenol
90-05-1

2-methoxy-phenol

ortho-nitrofluorobenzene
1493-27-2

ortho-nitrofluorobenzene

1-methoxy-2-(2-nitrophenoxy)benzene
74865-12-6

1-methoxy-2-(2-nitrophenoxy)benzene

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 95℃; for 20h;100%
With potassium carbonate In dimethyl sulfoxide at 95℃;
3-chloro-4-fluoronitrobenzene
350-30-1

3-chloro-4-fluoronitrobenzene

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-chloro-1-(2-methoxyphenoxy)-4-nitrobenzene
1097189-03-1

2-chloro-1-(2-methoxyphenoxy)-4-nitrobenzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17h;100%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

2,4-dideuterio-6-methoxy-phenol
7329-54-6

2,4-dideuterio-6-methoxy-phenol

Conditions
ConditionsYield
With perchloric acid; d(4)-methanol at 75℃; for 72h; Inert atmosphere;100%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

cyclohexane
110-82-7

cyclohexane

Conditions
ConditionsYield
With hydrogen In dodecane at 200℃; under 15001.5 Torr; for 2h;99.6%
With rhodium contaminated with carbon; N-methyldiethanolamine trifluoromethanesulfonate; hydrogen at 120℃; under 30003 Torr; for 6h; Autoclave;93.5%
With Ni-doped silica; hydrogen In decalin at 140℃; under 22502.3 Torr; for 5h; Reagent/catalyst; Autoclave;91.7%
pivaloyl chloride
3282-30-2

pivaloyl chloride

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-methoxyphenyl pivalate
25491-51-4

2-methoxyphenyl pivalate

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;99%
With pyridine
acetic anhydride
108-24-7

acetic anhydride

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-methoxyphenyl acetate
613-70-7

2-methoxyphenyl acetate

Conditions
ConditionsYield
With magnesium(II) perchlorate at 20℃; for 1h;99%
With iodine at 25℃; for 0.0166667h;99%
With Methylenediphosphonic acid at 20℃; for 2h; neat (no solvent);99%
N,N-diethylcarbamyl chloride
88-10-8

N,N-diethylcarbamyl chloride

2-methoxy-phenol
90-05-1

2-methoxy-phenol

N,N-diethyl-1-carbamyloxy-2-methoxybenzene
85630-19-9

N,N-diethyl-1-carbamyloxy-2-methoxybenzene

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 14h; Reflux;99%
With pyridine for 6h; Heating;96%
With sodium hydride In diethyl ether93%
2-Bromo-1-(3,4-dimethoxyphenyl)ethanone
1835-02-5

2-Bromo-1-(3,4-dimethoxyphenyl)ethanone

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-methoxyphenoxy-3',4'-dimethoxyacetophenone
22675-96-3

2-methoxyphenoxy-3',4'-dimethoxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 4h; Reflux;99%
With potassium carbonate In acetone97%
Stage #1: 2-methoxy-phenol With potassium carbonate In acetone at 20℃; for 0.5h;
Stage #2: 2-Bromo-1-(3,4-dimethoxyphenyl)ethanone In acetone Reflux;
95%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2-tosyloxyanisole
4416-67-5

2-tosyloxyanisole

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 2h; Reagent/catalyst; Green chemistry;99%
Stage #1: 2-methoxy-phenol With potassium hydroxide In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran at 60℃; Inert atmosphere;
99%
With triethylamine In dichloromethane at 20℃;99%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-methoxycyclohexanol
2979-24-0

2-methoxycyclohexanol

Conditions
ConditionsYield
With 3 weight% Pd/C; hydrogen In Hexadecane at 249.84℃; under 22502.3 Torr; Reagent/catalyst; Autoclave;99%
With hydrogen In water at 80℃; under 15001.5 Torr; for 6.5h;99%
With Ni-doped silica; hydrogen In decalin at 140℃; under 22502.3 Torr; for 5h; Reagent/catalyst; Autoclave;95.5%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

benzene-1,2-diol
120-80-9

benzene-1,2-diol

Conditions
ConditionsYield
Stage #1: 2-methoxy-phenol With pyridine; iodine; aluminium In acetonitrile for 18h; Reflux;
Stage #2: With hydrogenchloride In water; acetonitrile at 20℃;
99%
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 3h; Reagent/catalyst; Autoclave; Inert atmosphere; Green chemistry;97%
With aluminium(III) iodide; calcium oxide In acetonitrile at 80℃; for 18h; Reagent/catalyst;94%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

cyclohexanol
108-93-0

cyclohexanol

Conditions
ConditionsYield
With hydrogen In water at 160℃; for 10h; Temperature; Concentration; Reagent/catalyst;99%
With potassium hydroxide; Raney Ni-Al; water at 90℃; for 16h;90.8%
With acetic acid; platinum Hydrogenation;
iodobenzene
591-50-4

iodobenzene

2-methoxy-phenol
90-05-1

2-methoxy-phenol

2-methoxyphenyl phenyl ether
1695-04-1

2-methoxyphenyl phenyl ether

Conditions
ConditionsYield
With copper(I) oxide; caesium carbonate; imidazole-4-carboxylic acid In acetonitrile at 80℃; for 24h;99%
With copper(l) iodide; 1-(dimethylamino-1-yl-pyridin-2-yl-methyl)naphthalen-2-ol; potassium carbonate In dimethyl sulfoxide at 120℃; for 24h; Ullmann Condensation; Green chemistry;99%
With potassium hydroxide In dimethyl sulfoxide at 110℃; for 15h; Inert atmosphere;96%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

acetyl chloride
75-36-5

acetyl chloride

2-methoxyphenyl acetate
613-70-7

2-methoxyphenyl acetate

Conditions
ConditionsYield
99%
With pyridine In dichloromethane at 0 - 18℃; for 24h;99%
With pyridine In dichloromethane at 0 - 20℃; for 18h;99%

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