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  • 6971-51-3 Structure
  • Basic information

    1. Product Name: m-Anisyl alcohol
    2. Synonyms: (3-Methoxyphenyl)methanol;Benzenemethanol, 3-methoxy-;3-METHOXYBENZYL ALCOHOL;3-ANISE ALCOHOL;3-ANISIC ALCOHOL;3-ANISYL ALCOHOL;M-ANISE ALCOHOL;M-ANISYL ALCOHOL
    3. CAS NO:6971-51-3
    4. Molecular Formula: C8H10O2
    5. Molecular Weight: 138.16
    6. EINECS: 230-200-5
    7. Product Categories: Benzhydrols, Benzyl & Special Alcohols;Alcohol;Alcohols;Building Blocks;C7 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
    8. Mol File: 6971-51-3.mol
    9. Article Data: 159
  • Chemical Properties

    1. Melting Point: 30°C
    2. Boiling Point: 250 °C723 mm Hg(lit.)
    3. Flash Point: >230 °F
    4. Appearance: Clear slightly yellow to slightly brown/Liquid
    5. Density: 1.112 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.0136mmHg at 25°C
    7. Refractive Index: n20/D 1.540(lit.)
    8. Storage Temp.: Store below +30°C.
    9. Solubility: Acetonitrile (Sparingly), Chloroform (Sparingly), DMSO (Slightly)
    10. PKA: 14.43±0.10(Predicted)
    11. Water Solubility: immiscible
    12. BRN: 2042063
    13. CAS DataBase Reference: m-Anisyl alcohol(CAS DataBase Reference)
    14. NIST Chemistry Reference: m-Anisyl alcohol(6971-51-3)
    15. EPA Substance Registry System: m-Anisyl alcohol(6971-51-3)
  • Safety Data

    1. Hazard Codes: Xn,Xi
    2. Statements: 36/37/38-22
    3. Safety Statements: 23-24/25-37/39-26-36
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 6971-51-3(Hazardous Substances Data)

6971-51-3 Usage

Description

m-Anisyl alcohol, also known as 3-methoxybenzyl alcohol, is an organic compound that serves as a crucial raw material and intermediate in various industries due to its versatile chemical properties.

Uses

Used in Organic Synthesis:
m-Anisyl alcohol is used as a key intermediate for the synthesis of various organic compounds, contributing to the development of new chemical entities and enhancing the scope of organic chemistry.
Used in Pharmaceuticals:
In the pharmaceutical industry, m-Anisyl alcohol is utilized as an important building block in the production of drugs, playing a vital role in the synthesis of medicinally relevant molecules and improving treatment options for various diseases.
Used in Agrochemicals:
m-Anisyl alcohol is employed as a crucial component in the development of agrochemicals, such as pesticides and herbicides, helping to increase agricultural productivity and protect crops from pests and diseases.
Used in Dyestuff:
In the dyestuff industry, m-Anisyl alcohol is used as a significant raw material for the production of dyes and pigments, contributing to the creation of a wide range of colorants for various applications, including textiles, plastics, and printing inks.

Check Digit Verification of cas no

The CAS Registry Mumber 6971-51-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,9,7 and 1 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 6971-51:
(6*6)+(5*9)+(4*7)+(3*1)+(2*5)+(1*1)=123
123 % 10 = 3
So 6971-51-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O2/c1-10-8-4-2-3-7(5-8)6-9/h2-5,9H,6H2,1H3

6971-51-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (A15471)  3-Methoxybenzyl alcohol, 98+%   

  • 6971-51-3

  • 25g

  • 284.0CNY

  • Detail
  • Alfa Aesar

  • (A15471)  3-Methoxybenzyl alcohol, 98+%   

  • 6971-51-3

  • 100g

  • 939.0CNY

  • Detail

6971-51-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Methoxybenzyl Alcohol

1.2 Other means of identification

Product number -
Other names Benzenemethanol, 3-methoxy-

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:6971-51-3 SDS

6971-51-3Synthetic route

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With hydrogen; Pd as electrode electrochemical reaction;100%
With sodium tetrahydroborate In methanol at 20℃; for 1h;100%
With sodium tetrahydroborate; Dowex1-x8 In tetrahydrofuran at 20℃; for 0.5h;99%
methyl 3-methoxybenzoate
5368-81-0

methyl 3-methoxybenzoate

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
Stage #1: methyl 3-methoxybenzoate With diethylzinc; lithium chloride In tetrahydrofuran; hexane at 20℃; for 6h; Inert atmosphere;
Stage #2: With sodium hydroxide In tetrahydrofuran; hexane; water at 20℃; for 8h; Inert atmosphere; chemoselective reaction;
98%
With HN(CH2CH2C3H3N2Mes)2Cl2; potassium tert-butylate; hydrogen; cobalt(II) chloride In tetrahydrofuran at 100℃; under 22502.3 Torr; for 16h; Autoclave; Glovebox;91%
With methanol; sodium tetrahydroborate In tetrahydrofuran at 65℃; for 4h;90%
(3-Methoxy-benzyloxy)-trimethyl-silane
132816-03-6

(3-Methoxy-benzyloxy)-trimethyl-silane

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With Oxone In methanol for 0.4h; Heating;98%
With bismuth(lll) trifluoromethanesulfonate In methanol at 20℃; for 0.0333333h;97%
With poly (ethylene glycol)-sulfonated sodium montmorillonite nanocomposite In methanol at 20℃; for 0.00833333h;96%
2-(3-methoxybenzyloxy)tetrahydro-2H-pyran
18483-97-1

2-(3-methoxybenzyloxy)tetrahydro-2H-pyran

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In methanol for 0.05h;97%
With sulfuric acid; silica gel In methanol at 20℃; for 0.5h;95%
With Oxone In methanol for 1.5h; Heating;80%
ethyl 3-methoxybenzoate
10259-22-0

ethyl 3-methoxybenzoate

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With lithium borohydride In diethyl ether; toluene at 100℃; for 0.5h;95%
2-tert-butylsulfinyl-3-methoxyphenylmethanol
1026136-92-4

2-tert-butylsulfinyl-3-methoxyphenylmethanol

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With nickel In ethanol for 3h; Reflux;94%
2-(3-methoxyphenyl)-1,3-dioxolane
19693-78-8

2-(3-methoxyphenyl)-1,3-dioxolane

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With sulfuric acid; zinc at 38℃; for 2h; Temperature;93.5%
3-methoxy-1-[(ethoxymethoxy)methyl]benzene
1058648-97-7

3-methoxy-1-[(ethoxymethoxy)methyl]benzene

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
phosphotungstic acid In ethanol for 3h; Heating;93%
With 1-methylimidazole hydrogen sulfate at 50℃; for 1.25h; chemoselective reaction;92%
3-methoxy-1-(methoxymethoxy)methyl benzene
161358-52-7

3-methoxy-1-(methoxymethoxy)methyl benzene

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With 1-methylimidazole hydrogen sulfate at 120℃; for 0.05h; Microwave irradiation; chemoselective reaction;93%
phosphotungstic acid In ethanol for 3h; Heating;89%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

A

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

B

1-(3-methoxyphenyl)-3-(p-tolyl)prop-2-yn-1-one

1-(3-methoxyphenyl)-3-(p-tolyl)prop-2-yn-1-one

Conditions
ConditionsYield
With triethylamine; zinc(II) iodide In toluene at 80℃; for 12h; Schlenk technique; Inert atmosphere;A n/a
B 93%
1-bromomethyl-3-methoxybenzene
874-98-6

1-bromomethyl-3-methoxybenzene

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With water; dimethyl sulfoxide at 50℃; for 24h; Schlenk technique; Sealed tube;90%
With potassium hydroxide In ethanol for 2h; Ambient temperature; Yield given;
C14H16O2Si

C14H16O2Si

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With sodium hydroxide In water Schlenk technique; Inert atmosphere;90%
With sodium hydroxide In water
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

A

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

B

3-Methoxybenzoic acid
586-38-9

3-Methoxybenzoic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 15℃; for 2.5h; Cannizzaro Reaction;A n/a
B 87%
With Ximenia american In aq. phosphate buffer; water at 30℃; for 72h; pH=7; Enzymatic reaction;A 75%
B n/a
4-hydroxymethyl-2-methoxyphenol
498-00-0

4-hydroxymethyl-2-methoxyphenol

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
Stage #1: 4-hydroxymethyl-2-methoxyphenol With TentaGel-N(R)C(O)CH2C2F4OC2F4SO2F; potassium carbonate In N,N-dimethyl-formamide at 20℃;
Stage #2: With formic acid; 1,3-bis-(diphenylphosphino)propane; triethylamine; palladium diacetate In N,N-dimethyl-formamide at 85℃; for 2h; Further stages.;
86%
2-((3-methoxybenzyl)oxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-((3-methoxybenzyl)oxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; methanol; water at 50℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique;84%
With water; sodium hydroxide In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Schlenk technique; Sealed tube;0.12 g
m-methoxybenzamide
5813-86-5

m-methoxybenzamide

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With C24H20ClN2OPRu; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 10640.7 Torr; for 36h; Inert atmosphere; Schlenk technique;83%
diisopropyl zinc
625-81-0

diisopropyl zinc

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

A

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

B

1-(3-methoxyphenyl)-2-methylpropan-1-ol

1-(3-methoxyphenyl)-2-methylpropan-1-ol

Conditions
ConditionsYield
With C35H47N5O4 In toluene at 0 - 20℃; for 12h; Inert atmosphere; enantioselective reaction;A 11%
B 83%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

A

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

B

3-methoxybenzyl 3-methoxybenzoate
24318-46-5

3-methoxybenzyl 3-methoxybenzoate

C

3-Methoxybenzoic acid
586-38-9

3-Methoxybenzoic acid

Conditions
ConditionsYield
With aluminum (III) chloride; triethylamine In dichloromethane at 20℃; for 48h; Cannizzaro Reaction;A 9%
B 81%
C 9%
With aluminum (III) chloride; triethylamine In dichloromethane at 20℃; for 48h; Cannizzaro Reaction;A 74%
B 12%
C 74%
3-Methoxybenzoic acid
586-38-9

3-Methoxybenzoic acid

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
Stage #1: 3-Methoxybenzoic acid With sodium aminodiboranate In tetrahydrofuran at 20℃;
Stage #2: With water
78%
With lithium aluminium tetrahydride; diethyl ether; benzene
With lithium aluminium tetrahydride
3-Hydroxybenzyl alcohol
620-24-6

3-Hydroxybenzyl alcohol

tetramethlyammonium chloride
75-57-0

tetramethlyammonium chloride

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With caesium carbonate In 1,2-dimethoxyethane at 145℃; for 1h; Microwave irradiation; Inert atmosphere; Sealed vessel;72%
2-Bromo-5-methoxybenzyl alcohol
150192-39-5

2-Bromo-5-methoxybenzyl alcohol

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;72%
3-METHOXYBENZYLAMINE
5071-96-5

3-METHOXYBENZYLAMINE

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With [Ir(κ2O,O-CH3COO)(I)2{κC,C'-methylenebis(N-methyl)imidazole-2-ylidene}]; water; glycerol; potassium hydroxide at 120℃; for 16h;70%
(3-methoxybenzyl)trimethylsilane
51755-56-7

(3-methoxybenzyl)trimethylsilane

A

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

B

1,2-bis(3-methoxyphenyl)ethane
36707-27-4

1,2-bis(3-methoxyphenyl)ethane

Conditions
ConditionsYield
With titanium(IV) oxide; silver sulfate In water; acetonitrile for 0.5h; Oxidation; desilylation; dimerization; coupling; Irradiation;A 27%
B 68%
2-tert-butylsulfinyl-3-methoxybenzaldehyde
1026136-90-2

2-tert-butylsulfinyl-3-methoxybenzaldehyde

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With nickel In methanol for 3h; Reflux;44%
vanillin triflate
194018-68-3

vanillin triflate

A

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

B

1-methoxy-3-methyl-benzene
100-84-5

1-methoxy-3-methyl-benzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 40h;A 30%
B 42%
allyl iodid
556-56-9

allyl iodid

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

A

1-(3-methoxyphenyl)but-3-en-1-ol
24165-65-9

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

B

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

C

1,2-bis(3-methoxyphenyl)-1,2-ethanediol
156091-01-9

1,2-bis(3-methoxyphenyl)-1,2-ethanediol

Conditions
ConditionsYield
With ammonium chloride; magnesium for 12h; Ambient temperature;A 40%
B 18 % Spectr.
C 37 % Spectr.
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

prenyl bromide
870-63-3

prenyl bromide

A

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

B

2,2-dimethyl-1-(3-methoxy phenyl)-3-butene-1-one
133480-24-7

2,2-dimethyl-1-(3-methoxy phenyl)-3-butene-1-one

C

1-(3-methoxy-phenyl)-2,2-dimethyl-but-3-en-1-ol

1-(3-methoxy-phenyl)-2,2-dimethyl-but-3-en-1-ol

D

3-methoxy-benzoic acid 1-(3-methoxy-phenyl)-2,2-dimethyl-but-3-enyl ester

3-methoxy-benzoic acid 1-(3-methoxy-phenyl)-2,2-dimethyl-but-3-enyl ester

Conditions
ConditionsYield
With chromium dichloride; lithium iodide In tetrahydrofuran at 55℃; for 3h; Hiyama-Nozaki reaction;A n/a
B n/a
C 33%
D n/a
(3-methoxybenzoyl)trimethylsilane
107325-75-7

(3-methoxybenzoyl)trimethylsilane

A

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

B

3-Methoxybenzoic acid
586-38-9

3-Methoxybenzoic acid

C

(R)-(3-Methoxy-phenyl)-trimethylsilanyl-methanol

(R)-(3-Methoxy-phenyl)-trimethylsilanyl-methanol

D

(S)-(-)-3-Methoxy-α-(trimethylsilyl)benzenemethanol

(S)-(-)-3-Methoxy-α-(trimethylsilyl)benzenemethanol

Conditions
ConditionsYield
With baker's yeast on montmorillonite K10; potassium chloride; Sucrose at 35℃; for 48h; Reduction; Bioreduction; Enzymatic reaction; Title compound not separated from byproducts;A 25%
B n/a
C n/a
D n/a
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

A

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

(1RS,2RS)-1,2-Bis(3-methoxyphenyl)ethane-1,2-diol
156091-01-9

(1RS,2RS)-1,2-Bis(3-methoxyphenyl)ethane-1,2-diol

C

(S,R)-1,2-bis(3-methoxyphenyl)ethane-1,2-diol

(S,R)-1,2-bis(3-methoxyphenyl)ethane-1,2-diol

Conditions
ConditionsYield
With zinc In water at 70℃; for 2h; Green chemistry;A 12%
B n/a
C n/a
With ammonium chloride; zinc In water at 45℃; for 2h;A 7%
B n/a
C n/a
With sodium hydroxide for 1.66667h; Ambient temperature; Yield given. Yields of byproduct given;
Stage #1: 3-methoxy-benzaldehyde With chloro-trimethyl-silane; samarium diiodide; tert-butylammonium hexafluorophosphate(V) In tetrahydrofuran at 20℃; Electrochemical reaction;
Stage #2: Acidic conditions; Overall yield = 42 %; diastereoselective reaction;
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With oxygen; perruthenate modified mesoporous silicate MCM-41 In toluene at 80℃; for 3h; Oxidation;100%
With Oxone; [Mn(NO3)2(2,3,5,6-tetra(2-pyridyl)pyrazine)(H2O)]; tetrabutylammomium bromide In dichloromethane at 20℃; Catalytic behavior; Reagent/catalyst;100%
With 1-benzyl-1-aza-4-azoniabicyclo<2.2.2>octane periodate In acetonitrile for 10h; Heating;99%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

m-methoxybenzyl chloride
824-98-6

m-methoxybenzyl chloride

Conditions
ConditionsYield
With thionyl chloride; triethylamine In dichloromethane at 20℃; for 1h;100%
With hydrogenchloride at 120℃; under 7500.75 Torr; Flow reactor;99%
With pyridine; thionyl chloride In benzene at 0℃; for 2h;96%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

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

1-bromomethyl-3-methoxybenzene

Conditions
ConditionsYield
With phosphorus tribromide In benzene at 20℃;100%
With chloro-trimethyl-silane; lithium bromide In acetonitrile for 22h; Bromination; Heating;98%
With 1H-imidazole; iodine In dichloromethane at 20℃; for 0.25h;96%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

acetic anhydride
108-24-7

acetic anhydride

m-(acetoxymethyl)anisole
35480-26-3

m-(acetoxymethyl)anisole

Conditions
ConditionsYield
With pyridine at 21℃; for 12h;100%
With pyridine 1.) 0 degC, 15 min 2.) room temperature, 12 h;99%
With tin(IV) tetraphenylporphyrin perchlorate at 20℃; for 0.0833333h;99%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3-methoxy-O-tert-butyldimethylsilylbenzyl alcohol
153974-48-2

3-methoxy-O-tert-butyldimethylsilylbenzyl alcohol

Conditions
ConditionsYield
With 1H-imidazole at 25℃;100%
With 1H-imidazole In N,N-dimethyl-formamide at 25℃;100%
With 1H-imidazole In dichloromethane94%
With 1H-imidazole In dichloromethane at 15 - 42.9℃; for 17h; Inert atmosphere; Large scale;94%
With 1H-imidazole In dichloromethane at 15 - 42.9℃; for 17.15h; Inert atmosphere; Large scale;94%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

benzoyl chloride
98-88-4

benzoyl chloride

3-methoxylbenzyl benzoate
24318-44-3

3-methoxylbenzyl benzoate

Conditions
ConditionsYield
With pyridine at 0℃; for 1.5h;100%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

1-methoxy-3-methyl-benzene
100-84-5

1-methoxy-3-methyl-benzene

Conditions
ConditionsYield
With palladium dichloride In methanol at 40℃; for 18h; Inert atmosphere; Green chemistry; chemoselective reaction;99%
With chlorocarbonylbis(triphenylphosphine)iridium(I); hydrazine hydrate; potassium hydroxide In methanol at 160℃; for 3h; Wolff-Kishner Reduction; Sealed tube;86%
With chlorocarbonylbis(triphenylphosphine)iridium(I); hydrazine hydrate; potassium hydroxide In methanol at 160℃; for 3h; Sealed tube;86%
With carbon monoxide; hydrogen; benzene unter Zusatz von Octacarbonyldikobalt und CoCO3 auf 190grad/238 at;
Multi-step reaction with 3 steps
1: 78 percent / sodium iodide; sodium hydride / tetrahydrofuran / 0 - 20 °C
2: sulfuryl chloride / CH2Cl2 / -78 °C
3: lithium; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 1 h / 0 °C
View Scheme
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

benzoic acid anhydride
93-97-0

benzoic acid anhydride

3-methoxylbenzyl benzoate
24318-44-3

3-methoxylbenzyl benzoate

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In acetonitrile for 0.5h; Heating;99%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

formic acid ethyl ester
109-94-4

formic acid ethyl ester

3-methoxybenzyl formate

3-methoxybenzyl formate

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate for 0.666667h; Heating;99%
With K5 for 1.25h; Heating;97%
(NH4)8[CeW10O36]*20H2O for 9h; Heating;85%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

aniline
62-53-3

aniline

N-(3-methoxybenzyl)aniline
81308-21-6

N-(3-methoxybenzyl)aniline

Conditions
ConditionsYield
With zinc(II) nitrate hexahydrate; potassium tert-butylate In toluene at 140℃; for 36h; Sealed tube; Inert atmosphere; Schlenk technique;99%
With sodium hydrogencarbonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In toluene at 110℃; for 17h;97%
With cesiumhydroxide monohydrate at 130℃; for 24h; Schlenk technique;96%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

(4-bromo-3-methoxyphenyl)methanol
17100-64-0

(4-bromo-3-methoxyphenyl)methanol

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 8h;99%
With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 1.5h;88%
With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 1.5h;88%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

ethyl acetoacetate
141-97-9

ethyl acetoacetate

ethyl 2-(3-methoxybenzyl)-3-oxobutanoate
63965-31-1

ethyl 2-(3-methoxybenzyl)-3-oxobutanoate

Conditions
ConditionsYield
With rice husk ash nano silica supported 12-tungstophosphoric acid at 80℃; for 0.0333333h; Neat (no solvent);99%
With ferric hydrogen sulphate In 1,2-dichloro-ethane at 86℃; for 5h;65%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

methyl 2-[(3-methoxyphenyl)methyl]-3-oxobutanoate
1350653-48-3

methyl 2-[(3-methoxyphenyl)methyl]-3-oxobutanoate

Conditions
ConditionsYield
With rice husk ash nano silica supported 12-tungstophosphoric acid at 80℃; for 0.0333333h; Neat (no solvent);99%
With cesium 12-tungstophosphate at 80℃; for 1h; Neat (no solvent);92%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

3-methoxybenzonitrile
1527-89-5

3-methoxybenzonitrile

Conditions
ConditionsYield
With ammonia; oxygen In tert-Amyl alcohol; water at 100℃; under 3750.38 Torr; for 10h; Autoclave; High pressure;99%
With ammonium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [{(MeOH)Cu(OAc)}(μ-k2:k1-2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)acetic acid(-H))]2*0.5H2O; tetraethylammonium iodide; oxygen; potassium carbonate In water at 60℃; under 760.051 Torr; for 24h;93%
With ammonia; oxygen In tert-Amyl alcohol; water at 130℃; under 3750.38 Torr; for 24h;92%
vinyl acetate
108-05-4

vinyl acetate

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

m-(acetoxymethyl)anisole
35480-26-3

m-(acetoxymethyl)anisole

Conditions
ConditionsYield
With Ximenia american In hexane at 30℃; for 24h; pH=5; Enzymatic reaction;99%
9H-fluorene
86-73-7

9H-fluorene

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

9-(3-methoxybenzyl)-9H-fluorene

9-(3-methoxybenzyl)-9H-fluorene

Conditions
ConditionsYield
With potassium tert-butylate In toluene at 120℃; for 3h; Inert atmosphere;99%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium tert-butylate In toluene at 120℃; for 18h; Inert atmosphere; Sealed tube;87%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

acetic acid
64-19-7

acetic acid

m-(acetoxymethyl)anisole
35480-26-3

m-(acetoxymethyl)anisole

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate at 20℃; for 0.333333h;98%
With K5 for 0.75h; Heating;97%
In neat (no solvent) at 70℃; for 0.416667h; Catalytic behavior;92 %Chromat.
(R)-5-oxo-5,6-dihydro-2H-pyran-2-yl acetate
33647-88-0

(R)-5-oxo-5,6-dihydro-2H-pyran-2-yl acetate

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

(S)-(-)-6-(3-methoxybenzyl)oxy-2H-pyran-3(6H)-one
581782-83-4

(S)-(-)-6-(3-methoxybenzyl)oxy-2H-pyran-3(6H)-one

Conditions
ConditionsYield
Stage #1: 3-methoxybenzyl alcohol With triphenyl phosphite; palladium diacetate In dichloromethane
Stage #2: (R)-5-oxo-5,6-dihydro-2H-pyran-2-yl acetate In dichloromethane
98%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

(3-Methoxy-benzyloxy)-trimethyl-silane
132816-03-6

(3-Methoxy-benzyloxy)-trimethyl-silane

Conditions
ConditionsYield
With poly(4-vinylpyridine) In acetonitrile at 20℃; for 0.0166667h;98%
With copper(II) sulfate In acetonitrile at 20℃; for 4h;95%
With iron(III) chloride In acetonitrile at 20℃;95%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-(3-methoxybenzyl)-4-methylbenzenesulfonamide
191085-63-9

N-(3-methoxybenzyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With Ru/Fe3O4; potassium carbonate at 150℃; for 12h; Inert atmosphere;98%
With air; copper diacetate; potassium carbonate at 150℃; for 12h;91%
With copper diacetate; potassium carbonate at 150℃; for 12h;91%
1,1,1,2,2,2-hexamethyldisilane
1450-14-2

1,1,1,2,2,2-hexamethyldisilane

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

(3-Methoxy-benzyloxy)-trimethyl-silane
132816-03-6

(3-Methoxy-benzyloxy)-trimethyl-silane

Conditions
ConditionsYield
With lanthanum(III) nitrate hexahydrate In acetonitrile at 20℃;98%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

acetylacetone
123-54-6

acetylacetone

3-(3-methoxybenzyl)pentane-2,4-dione
791809-44-4

3-(3-methoxybenzyl)pentane-2,4-dione

Conditions
ConditionsYield
With rice husk ash nano silica supported 12-tungstophosphoric acid at 80℃; for 0.0333333h; Neat (no solvent);98%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

2-amino-phenol
95-55-6

2-amino-phenol

2-(3-methoxyphenyl)benzoxazole
32959-59-4

2-(3-methoxyphenyl)benzoxazole

Conditions
ConditionsYield
Stage #1: 3-methoxybenzyl alcohol With oxygen at 106℃; under 3800.26 Torr; for 0.216667h; Flow reactor; Green chemistry;
Stage #2: 2-amino-phenol at 106℃; Flow reactor; Green chemistry;
Stage #3: at 106℃; for 0.666667h; Flow reactor; Green chemistry;
98%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

2-(3-methoxybenzyloxy)tetrahydro-2H-pyran
18483-97-1

2-(3-methoxybenzyloxy)tetrahydro-2H-pyran

Conditions
ConditionsYield
With H7[PMo8V4O40] In acetonitrile at 20℃; for 0.0833333h;97.5%
With C10H10N2O6S2(2+)*2HO4S(1-) at 20℃; for 0.116667h;91%
With P-benzyltriphenylphosphonium tribromide In dichloromethane at 20℃; for 0.116667h;90%
2-chloropyridine
109-09-1

2-chloropyridine

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

2-(3-methoxybenzyloxy)pyridine
1044501-34-9

2-(3-methoxybenzyloxy)pyridine

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 98℃; for 18h;97%
With potassium tert-butylate In 1,4-dioxane at 98℃; for 19h;97%
3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

benzamide
55-21-0

benzamide

N-(3'-methoxybenzyl)benzamide

N-(3'-methoxybenzyl)benzamide

Conditions
ConditionsYield
With potassium carbonate at 160℃; for 12h;97%
With C44H39IrN2P(1+)*C32H12BF24(1-); caesium carbonate In toluene at 120℃; for 12h; Inert atmosphere;91%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate at 130℃; for 17h; Inert atmosphere;59%

6971-51-3Relevant articles and documents

Phosphoric acid-modified commercial kieselguhr supported palladium nanoparticles as efficient catalysts for low-temperature hydrodeoxygenation of lignin derivatives in water

Cui, Yuntong,Liu, Zhaohui,Ran, Jiansu,Wang, Jianjian,Yangcheng, Ruixue

, p. 1570 - 1577 (2022/03/14)

Efficient production of high value-added chemicals and biofuels via low-temperature chemoselective HDO of lignin derivatives in water is still a challenge. Here, we construct a low-cost, active and stable Pd/PCE catalyst using phosphoric acid-modified commercial Celite (PCE) as the support, and this catalyst exhibits excellent activity in low-temperature HDO of vanillin as well as other lignin derivatives in water. The superior catalytic performance is due to the presence of P species on the surface of Pd/PCE, accelerating the selective conversion of the intermediate into the final product. Detailed experimental and mechanistic studies reveal that the rapid conversion of the intermediate to the final product proceeds via a free-radical process in an interfacial microenvironment created by intimate interacting between the P species and Pd NPs. The insights of this work provide a new low-cost catalytic system for efficient production of valuable chemicals and future biofuels from lignin derivatives. This journal is

KB3H8: An environment-friendly reagent for the selective reduction of aldehydes and ketones to alcohols

Li, Xinying,Mi, Tongge,Guo, Wenjing,Ruan, Zhongrui,Guo, Yu,Ma, Yan-Na,Chen, Xuenian

supporting information, p. 12776 - 12779 (2021/12/10)

Selective reduction of aldehydes and ketones to their corresponding alcohols with KB3H8, an air- and moisture-stable, nontoxic, and easy-to-handle reagent, in water and THF has been explored under an air atmosphere for the first time. Control experiments illustrated the good selectivity of KB3H8 over NaBH4 for the reduction of 4-acetylbenzaldehyde and aromatic keto esters. This journal is

Disproportionation of aliphatic and aromatic aldehydes through Cannizzaro, Tishchenko, and Meerwein–Ponndorf–Verley reactions

Sharifi, Sina,Sharifi, Hannah,Koza, Darrell,Aminkhani, Ali

, p. 803 - 808 (2021/07/20)

Disproportionation of aldehydes through Cannizzaro, Tishchenko, and Meerwein–Ponndorf–Verley reactions often requires the application of high temperatures, equimolar or excess quantities of strong bases, and is mostly limited to the aldehydes with no CH2 or CH3 adjacent to the carbonyl group. Herein, we developed an efficient, mild, and multifunctional catalytic system consisting AlCl3/Et3N in CH2Cl2, that can selectively convert a wide range of not only aliphatic, but also aromatic aldehydes to the corresponding alcohols, acids, and dimerized esters at room temperature, and in high yields, without formation of the side products that are generally observed. We have also shown that higher AlCl3 content favors the reaction towards Cannizzaro reaction, yet lower content favors Tishchenko reaction. Moreover, the presence of hydride donor alcohols in the reaction mixture completely directs the reaction towards the Meerwein–Ponndorf–Verley reaction. Graphic abstract: [Figure not available: see fulltext.].

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