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108-39-4 Usage

General Description

M-Cresol, also known as meta-cresol or 3-methylphenol, is a colorless to yellowish liquid with a strong, sweet, phenolic odor. It is commonly used as a disinfectant and antiseptic in the production of industrial products, such as resins, dyes, and herbicides, as well as in the synthesis of pharmaceuticals and organic chemicals. M-Cresol is also used as a chemical intermediate in the production of antioxidants, perfumes, and flavorings. It is considered toxic and a potential environmental pollutant, and exposure to m-cresol can cause irritation to the skin, eyes, and respiratory system. Due to its potential health and environmental hazards, proper safety precautions should be taken when handling m-cresol.

Check Digit Verification of cas no

The CAS Registry Mumber 108-39-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 8 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 108-39:
(5*1)+(4*0)+(3*8)+(2*3)+(1*9)=44
44 % 10 = 4
So 108-39-4 is a valid CAS Registry Number.

108-39-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (C0401)  m-Cresol  >98.0%(GC)

  • 108-39-4

  • 25g

  • 140.00CNY

  • Detail
  • TCI America

  • (C0401)  m-Cresol  >98.0%(GC)

  • 108-39-4

  • 500g

  • 525.00CNY

  • Detail
  • Alfa Aesar

  • (A10733)  m-Cresol, 99%   

  • 108-39-4

  • 250g

  • 267.0CNY

  • Detail
  • Alfa Aesar

  • (A10733)  m-Cresol, 99%   

  • 108-39-4

  • 1000g

  • 536.0CNY

  • Detail
  • Alfa Aesar

  • (A10733)  m-Cresol, 99%   

  • 108-39-4

  • 2500g

  • 1204.0CNY

  • Detail
  • Alfa Aesar

  • (A10733)  m-Cresol, 99%   

  • 108-39-4

  • 5000g

  • 2218.0CNY

  • Detail
  • Sigma-Aldrich

  • (65996)  m-Cresol  analytical standard

  • 108-39-4

  • 65996-1ML-F

  • 186.03CNY

  • Detail
  • Sigma-Aldrich

  • (65996)  m-Cresol  analytical standard

  • 108-39-4

  • 65996-5ML-F

  • 742.95CNY

  • Detail
  • Supelco

  • (40251-U)  3-Methylphenol  certified reference material, 5000 μg/mL in methanol

  • 108-39-4

  • 40251-U

  • 533.52CNY

  • Detail
  • Supelco

  • (442391)  3-Methylphenol  analytical standard

  • 108-39-4

  • 000000000000442391

  • 234.00CNY

  • Detail
  • USP

  • (1395204)  Metacresol  United States Pharmacopeia (USP) Reference Standard

  • 108-39-4

  • 1395204-1ML

  • 4,588.74CNY

  • Detail

108-39-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name m-cresol

1.2 Other means of identification

Product number -
Other names 3-hydroxytoluene

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:108-39-4 SDS

108-39-4Synthetic route

m-cyanophenol
873-62-1

m-cyanophenol

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol for 2h; Ambient temperature;100%
With 20 % Pd(OH)2/C; hydrogen In methanol at 20℃; under 760.051 Torr; for 3h;70%
ethyl (m-tolyl)carbonate
22719-82-0

ethyl (m-tolyl)carbonate

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With sodium hydrogen telluride In ethanol for 0.5h; Quantum yield; Heating; buffer: deoxygen. acetic acid;100%
(3-methylphenoxy)trimethylsilane
17902-31-7

(3-methylphenoxy)trimethylsilane

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With water; potassium carbonate In ethanol at 75℃; for 10h;100%
With Nanoporous Na+-Montmorillonite Perchloric Acid In ethanol at 20℃; for 0.05h;91%
triethyl(3-methylphenoxy)silane
18406-01-4

triethyl(3-methylphenoxy)silane

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With water; potassium carbonate In ethanol at 75℃; for 10h;99%
1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methylbenzene
62790-75-4

1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methylbenzene

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With water; potassium carbonate In ethanol at 75℃; for 12h;98%
With sodium cyanide In ethanol; water at 80℃; for 17h; chemoselective reaction;83.7%
With iodine In methanol for 22h; Ambient temperature;33%
4-iodo-3-methyl-phenol
133921-27-4

4-iodo-3-methyl-phenol

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With potassium carbonate; isopropyl alcohol; palladium diacetate; triphenylphosphine at 90℃; for 14h;98%
m-tolylboronic acid
17933-03-8

m-tolylboronic acid

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With dihydrogen peroxide at 20℃; for 0.166667h; Green chemistry;98%
With sodium perborate tetrahydrate In neat (no solvent) at 25℃; for 0.166667h; Green chemistry;98%
With solid poly(N-vinylpyrrolidone)-hydrogen peroxide complex (PVD-H2O2 complex) In dichloromethane at 20℃; regioselective reaction;97%
m-tolylboronic acid
17933-03-8

m-tolylboronic acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;97%
tetrahydro-2-(3-methylphenoxy)-2H-pyran
144265-47-4

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

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
Stage #1: tetrahydro-2-(3-methylphenoxy)-2H-pyran With aluminium(III) triflate In methanol at 20 - 25℃; for 2h; Inert atmosphere;
Stage #2: With water; sodium hydrogencarbonate In methanol; dichloromethane at 20 - 25℃; Inert atmosphere;
96%
With methanol at 20℃; for 0.833333h;87%
3-acetoxytoluene
122-46-3

3-acetoxytoluene

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With copper dichloride In methanol; water for 3h; Heating;95%
With Tris buffer; water; alpha cyclodextrin at 25℃; under 1500120 Torr; Rate constant; pH 8.3; further pressures; meta and para specific hydrolysis catalyzed by α-CD, pressure effects on, pressure dependence of log k, activation volume for the acylation, ΔV of CD-complex formation;
1-methoxy-3-methyl-benzene
100-84-5

1-methoxy-3-methyl-benzene

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; N-methylaniline In diethyl ether; xylene at 120℃; for 6.5h;95%
With trimethylsilyl iodide at 105 - 114℃; for 0.25h; Microwave irradiation; Inert atmosphere;92%
With 1,3-dimethyl-2-imidazolidinone; sodium hexamethyldisilazane In tetrahydrofuran at 185℃; for 12h; further reagent: LDA;87%
potassium trifluoro(3-methylphenyl)borate

potassium trifluoro(3-methylphenyl)borate

A

3,3'-dimethyl-biphenyl
612-75-9

3,3'-dimethyl-biphenyl

B

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
gold(0):poly(N-vinyl-2-pyrrolidine) nanocluster In phosphate buffer at 46.84℃; for 24h; pH=6.86;A 95%
B 4%
2-chloro-5-methylphenol
615-74-7

2-chloro-5-methylphenol

2-chloro-m-cresol
608-26-4

2-chloro-m-cresol

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With hydrogen; 0.75% Pd/Al2O3 at 180℃; Product distribution / selectivity;94.7%
With hydrogen at 180℃; Product distribution / selectivity;60.07%
With hydrogen; palladium on activated charcoal at 180℃; for 0 - 48h; Product distribution / selectivity;45.54%
m-methylcyclohexanol
591-23-1

m-methylcyclohexanol

A

3-methyl-phenol
108-39-4

3-methyl-phenol

B

toluene
108-88-3

toluene

C

3-Methylcyclohexanone
591-24-2, 625-96-7

3-Methylcyclohexanone

Conditions
ConditionsYield
platinum; potassium oxide at 425℃;A 94%
B 1.8%
C 4.2%
platinum; potassium oxide at 300℃; Product distribution; Kinetics; other content of catalyst, other temperature;
1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
Stage #1: 1-amino-3-methylbenzene With sulfuric acid at 20℃; Cooling with ice;
Stage #2: With sodium nitrite In water Reflux;
93%
Stage #1: 1-amino-3-methylbenzene With tetrafluoroboric acid In water at 20℃; for 0.0333333h;
Stage #2: With sodium nitrite In water at 0℃; for 0.5h;
Stage #3: With copper(I) oxide; copper(II) sulfate In water at 0 - 20℃; for 0.5h;
53%
With phosphoric acid; water at 280℃;
Diazotization;
Stage #1: 1-amino-3-methylbenzene With isopentyl nitrite In N,N-dimethyl-formamide Flow reactor;
Stage #2: With water In N,N-dimethyl-formamide Heating; Flow reactor;
Kohlensaeure-butyl-m-tolyl-ester
1847-82-1

Kohlensaeure-butyl-m-tolyl-ester

N-butylamine
109-73-9

N-butylamine

A

n-butylcarbamic acid n-butyl ester
13105-52-7

n-butylcarbamic acid n-butyl ester

B

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With N,N-dimethyl-formamideA 92%
B n/a
1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methylbenzene
62790-75-4

1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methylbenzene

Cs2CO3

Cs2CO3

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 20℃; for 3h;92%
(2-methyl-4-hydroxyphenyl)boronic acid
493035-82-8

(2-methyl-4-hydroxyphenyl)boronic acid

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); water In toluene at 90℃; for 1h; Microwave irradiation; Green chemistry;92%
meta-bromotoluene
591-17-3

meta-bromotoluene

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
Stage #1: meta-bromotoluene With copper(l) iodide; 2-methyl-8-quinolinol; tetra(n-butyl)ammonium hydroxide In water; dimethyl sulfoxide at 130℃; for 14h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃;
91%
With copper(I) oxide; tetra(n-butyl)ammonium hydroxide; 1,10-phenanthroline-4,7-diol In water at 110℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry;87%
With copper(l) iodide; potassium hydroxide In water at 120℃; for 8h; Inert atmosphere;80%
4-Chloro-3-methylphenol
59-50-7

4-Chloro-3-methylphenol

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With palladium on activated charcoal; formic acid; N,N-dimethyl-formamide for 5h; Heating;90%
With sodium hydroxide; iron at 200℃; im geschlossenen Gefaess;
3-Iodotoluene
625-95-6

3-Iodotoluene

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
Stage #1: 3-Iodotoluene With copper(l) iodide; tetra(n-butyl)ammonium hydroxide In water at 60℃; for 24h; Inert atmosphere; Sealed tube;
Stage #2: With hydrogenchloride In water; ethyl acetate at 20℃; for 2h; Inert atmosphere; chemoselective reaction;
89%
Stage #1: 3-Iodotoluene With copper(l) iodide; cesiumhydroxide monohydrate; 1,3-diphenylpropanedione In water; dimethyl sulfoxide at 130℃; for 24h; Inert atmosphere;
Stage #2: With hydrogenchloride In dichloromethane; water; dimethyl sulfoxide at 20℃; Inert atmosphere; chemoselective reaction;
84%
With tetra(n-butyl)ammonium hydroxide In water; dimethyl sulfoxide at 150℃; for 0.333333h; Flow reactor;84%
m-tolylboronic acid
17933-03-8

m-tolylboronic acid

oxygen
80937-33-3

oxygen

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With triethanolamine In water at 20℃; for 18h; Sonication; Irradiation; Green chemistry;89%
With methylene blue; N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 7h; Schlenk technique; Irradiation;
m-hydroxybenzyl bromide
74597-04-9

m-hydroxybenzyl bromide

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In 2-methyltetrahydrofuran at -15 - 20℃; for 24.16h;89%
3-methylcyclohexen-2-one
1193-18-6

3-methylcyclohexen-2-one

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With Pd(2+)*2C2H6OS*2BF4(1-)*6C12H6N2O4(2-)*4Zr(4+)*4HO(1-)*4O(2-); oxygen In dimethyl sulfoxide at 100℃; under 760.051 Torr; for 35h; Sealed tube; Inert atmosphere;86%
With ethene; 5%-palladium/activated carbon In acetonitrile at 80℃; under 2280.15 Torr; for 24h; Autoclave;86%
With oxygen; 6C12H6N2O4(2-)*6Zr(4+)*4HO(1-)*4O(2-)*6Pd(2+)*12C2H6OS*12BF4(1-) In dimethyl sulfoxide at 100℃; for 35h; Inert atmosphere;86%
3-hydroxybenzyl iodide
102998-68-5

3-hydroxybenzyl iodide

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With indium; water for 5h; ultrasound;86%
m-tolylhydrazine
536-89-0

m-tolylhydrazine

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With oxygen; eosin Y disodium salt In acetonitrile for 20h; Sealed tube; Irradiation;86%
1-chloro-3-methylbenzene
108-41-8

1-chloro-3-methylbenzene

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With aluminum (III) chloride; choline chloride; urea; sodium hydroxide at 180℃; for 6h; Green chemistry;85.7%
1-allyloxy-3-methylbenzene
1758-10-7

1-allyloxy-3-methylbenzene

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride In benzene for 20h; Heating;85%
With 12-TPA/SBA 15 In 1,4-dioxane at 110℃;72%
1-((4-methoxybenzyl)oxy)-3-methylbenzene

1-((4-methoxybenzyl)oxy)-3-methylbenzene

3-methyl-phenol
108-39-4

3-methyl-phenol

Conditions
ConditionsYield
With oxalyl dichloride In 1,2-dichloro-ethane at 20℃; for 2.66667h;85%
acetic anhydride
108-24-7

acetic anhydride

3-methyl-phenol
108-39-4

3-methyl-phenol

3-acetoxytoluene
122-46-3

3-acetoxytoluene

Conditions
ConditionsYield
With pyridine In dichloromethane100%
at 20℃; for 0.666667h;100%
With Sulfate; titanium(IV) oxide In chloroform at 61℃; for 0.05h;99%
3-methyl-phenol
108-39-4

3-methyl-phenol

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

(4-nitro-benzyl)-m-tolyl ether

(4-nitro-benzyl)-m-tolyl ether

Conditions
ConditionsYield
With sodium hydroxide In water for 0.00416667h; microwave irradiation;100%
With alkaline solution
3-methyl-phenol
108-39-4

3-methyl-phenol

N,N-Dimethylcarbamoyl chloride
79-44-7

N,N-Dimethylcarbamoyl chloride

m-tolyl dimethylcarbamate
7305-07-9

m-tolyl dimethylcarbamate

Conditions
ConditionsYield
Stage #1: 3-methyl-phenol With sodium hydride In N,N-dimethyl-formamide at 20℃;
Stage #2: N,N-Dimethylcarbamoyl chloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
100%
Stage #1: 3-methyl-phenol With pyridine; potassium carbonate In acetonitrile for 0.333333h;
Stage #2: N,N-Dimethylcarbamoyl chloride In acetonitrile for 2h;
85%
With pyridine In benzene
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

3-methyl-phenol
108-39-4

3-methyl-phenol

3-methylphenyl methanesulfonate
1077-02-7

3-methylphenyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 0 - 20℃; for 0.166667h; Green chemistry;100%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;80.5%
With pyridine
With triethylamine In dichloromethane at 0℃;
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

3-methyl-phenol
108-39-4

3-methyl-phenol

2-m-Tolyloxy-tetrahydro-furan
120649-53-8

2-m-Tolyloxy-tetrahydro-furan

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane for 1h; Ambient temperature;100%
bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

3-methyl-phenol
108-39-4

3-methyl-phenol

m-tolyloxyacetic acid methyl ester
63051-20-7

m-tolyloxyacetic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In butanone for 5.5h; Heating;100%
With caesium carbonate In N,N-dimethyl-formamide at 25℃; for 4h;100%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;89%
With potassium carbonate In N-methyl-acetamide
3-methyl-phenol
108-39-4

3-methyl-phenol

<2H3>-m-cresol
108791-52-2

<2H3>-m-cresol

Conditions
ConditionsYield
With perchloric acid; d(4)-methanol at 75℃; for 144h; Inert atmosphere;100%
With water-d2; phosphorus tribromide for 5h; Heating;81%
3-methyl-phenol
108-39-4

3-methyl-phenol

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

3-methyl-4'-nitrodiphenyl ether
2303-25-5

3-methyl-4'-nitrodiphenyl ether

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 2h;100%
With potassium carbonate In N,N-dimethyl-formamide at 80℃;
With potassium carbonate In dimethyl sulfoxide Heating;
KF-Al2O3; 18-crown-6 ether In acetonitrile for 24h; Heating / reflux;
With potassium carbonate In N,N-dimethyl-formamide for 8h; Inert atmosphere; Heating;
2-vinyl-1,3-dioxane
5935-25-1

2-vinyl-1,3-dioxane

3-methyl-phenol
108-39-4

3-methyl-phenol

2-ethyl-2-m-tolyloxy-[1,3]dioxane

2-ethyl-2-m-tolyloxy-[1,3]dioxane

Conditions
ConditionsYield
With sodium carbonate; tris(triphenylphosphine)ruthenium(II) chloride at 140℃; for 4h;100%
With tris(triphenylphosphine)ruthenium(II) chloride; sodium carbonate at 120℃; for 4h; Inert atmosphere; regioselective reaction;86%
3-methyl-phenol
108-39-4

3-methyl-phenol

propargyl bromide
106-96-7

propargyl bromide

1-methyl-3-(prop-2-yn-1-yloxy)benzene
5651-89-8

1-methyl-3-(prop-2-yn-1-yloxy)benzene

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;100%
With potassium carbonate In N,N-dimethyl-formamide; toluene at 20℃; for 7h; Inert atmosphere;91%
Stage #1: 3-methyl-phenol With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 0.5h; Inert atmosphere;
Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
90%
N,N-diethylcarbamyl chloride
88-10-8

N,N-diethylcarbamyl chloride

3-methyl-phenol
108-39-4

3-methyl-phenol

3-methylphenyl N,N-diethylcarbamate

3-methylphenyl N,N-diethylcarbamate

Conditions
ConditionsYield
Stage #1: 3-methyl-phenol With sodium hydride In tetrahydrofuran; mineral oil at 23℃; for 1h; Inert atmosphere;
Stage #2: N,N-diethylcarbamyl chloride In tetrahydrofuran; mineral oil at 23℃; for 16h; Inert atmosphere;
100%
Stage #1: 3-methyl-phenol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.583333h;
Stage #2: N,N-diethylcarbamyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 12.08h;
85%
With potassium carbonate In acetonitrile at 85℃; for 18h;32%
3-methyl-phenol
108-39-4

3-methyl-phenol

2,4-dinitrophenyl benzoate
1523-15-5

2,4-dinitrophenyl benzoate

A

3-methylphenyl benzoate
614-32-4

3-methylphenyl benzoate

B

potassium 2,4-dinitrophenolate
14314-69-3

potassium 2,4-dinitrophenolate

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 25℃; for 5h;A 100%
B n/a
4'-methoxy-4-nitro-2,6-bis(trifluoromethyl)biphenyl
1365643-25-9

4'-methoxy-4-nitro-2,6-bis(trifluoromethyl)biphenyl

3-methyl-phenol
108-39-4

3-methyl-phenol

C22H16F6O2
1365643-29-3

C22H16F6O2

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 90℃; for 31h; Inert atmosphere;100%
t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

3-methyl-phenol
108-39-4

3-methyl-phenol

1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methylbenzene
62790-75-4

1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methylbenzene

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
triisopropylsilyl trifluoromethanesulfonate
80522-42-5

triisopropylsilyl trifluoromethanesulfonate

3-methyl-phenol
108-39-4

3-methyl-phenol

(3-methyl-phenoxy)-triisopropyl-silane

(3-methyl-phenoxy)-triisopropyl-silane

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
4-methoxymethoxy-2-naphthalencarboxylic acid

4-methoxymethoxy-2-naphthalencarboxylic acid

3-methyl-phenol
108-39-4

3-methyl-phenol

C20H18O4

C20H18O4

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 50℃; for 16h; Inert atmosphere;100%
3-methyl-phenol
108-39-4

3-methyl-phenol

1,2-Epoxy-3-bromopropane
3132-64-7

1,2-Epoxy-3-bromopropane

m-tolyl glycidyl ether
2186-25-6

m-tolyl glycidyl ether

Conditions
ConditionsYield
With potassium carbonate In butanone at 70 - 86℃; for 66h;100%
3-methyl-phenol
108-39-4

3-methyl-phenol

m-methylcyclohexanol
591-23-1

m-methylcyclohexanol

Conditions
ConditionsYield
With hydrogen In water at 20℃; under 7500.75 Torr; for 6h; Autoclave;99.7%
With nickel(II) oxide; hydrogen; palladium In hexane at 80℃; under 7500.75 Torr; for 10h;89%
With hydrogen; palladium on activated charcoal In hexane at 120℃; under 37503 Torr; Rate constant; var. solvents;
3-methyl-phenol
108-39-4

3-methyl-phenol

2-cyanobenzyl chloride
612-13-5

2-cyanobenzyl chloride

2-(3-methylphenoxymethyl)benzonitrile
951906-95-9

2-(3-methylphenoxymethyl)benzonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h;99.3%
-butyl vinyl ether
111-34-2

-butyl vinyl ether

3-methyl-phenol
108-39-4

3-methyl-phenol

1-(n-butoxy)-1-(3-methylphenoxy)ethane
93308-46-4

1-(n-butoxy)-1-(3-methylphenoxy)ethane

Conditions
ConditionsYield
With trifluoroacetic acid at 60 - 65℃;99%
With phosphoric acid at 20℃;
3-methyl-phenol
108-39-4

3-methyl-phenol

acrylonitrile
107-13-1

acrylonitrile

3-(m-tolyloxy)propionitrile.
25268-06-8

3-(m-tolyloxy)propionitrile.

Conditions
ConditionsYield
With [μN,κP,κC,κN-{2-(i-Pr2PO),6-(CH2NBn)-(C6H3)}Ni]2 In benzene at 50℃; for 36h;99%
With sodium 3-methylphenoxide
N-benzyl-trimethylammonium hydroxide Heating;
With [{kp,kc,kp-2,6-(i-Pr2PO)2C6H3}Ni(NCMe)][OSO2CF3]; triethylamine In benzene-d6 at 20℃; for 4h; Michael condensation;100 %Spectr.
With [{kp,kc,kp-2,6-(i-Pr2PO)2C6H3}Ni(NCMe)][OSO2CF3]; triethylamine In toluene at 60℃; for 24h; Inert atmosphere;
3-methyl-phenol
108-39-4

3-methyl-phenol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

3-methylphenyl tosylate
3955-72-4

3-methylphenyl tosylate

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 2h; Green chemistry;99%
With aluminum dodecatungstophosphate at 20℃; for 0.133333h;95%
In pyridine at 45℃;75%
3-methyl-phenol
108-39-4

3-methyl-phenol

2,4,6-tribromo-m-cresol
4619-74-3

2,4,6-tribromo-m-cresol

Conditions
ConditionsYield
With benzyltrimethylammonium tribromide In methanol; dichloromethane99%
With bromine; acetic acid Ambient temperature;98%
With benzyltrimethylazanium tribroman-2-uide In methanol; dichloromethane for 1h; Ambient temperature; reagent 3.1 equivalent;93%
3-methyl-phenol
108-39-4

3-methyl-phenol

2-Methyl-1,4-benzoquinone
553-97-9

2-Methyl-1,4-benzoquinone

Conditions
ConditionsYield
With titanium superoxide; dihydrogen peroxide; acetic acid In water at 50℃; for 1h;99%
With dipyridinium dichromate In dichloromethane Ambient temperature;95%
With oxygen In water; acetonitrile at 40℃; under 15001.5 Torr; for 1h; Green chemistry;89%
3-methyl-phenol
108-39-4

3-methyl-phenol

epichlorohydrin
106-89-8

epichlorohydrin

m-tolyl glycidyl ether
2186-25-6

m-tolyl glycidyl ether

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 3h;99%
With sodium hydroxide; tetrabutylammomium bromide; potassium carbonate at 112℃; for 0.0833333h; Irradiation;95%
With sodium hydroxide; tetrabutylammomium bromide; potassium carbonate at 112℃; for 0.0833333h; microwave irradiation;95%
1,2-Epoxyhexane
1436-34-6

1,2-Epoxyhexane

3-methyl-phenol
108-39-4

3-methyl-phenol

(S)-1-(3-methylphenoxy)hexan-2-ol

(S)-1-(3-methylphenoxy)hexan-2-ol

Conditions
ConditionsYield
With (R,R)-(salen)Co(H2O); 3 A molecular sieve In various solvent(s) at 25℃; for 16h;99%
With 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol; polysytrene-immobilized chiral Co-salen complex In tetrahydrofuran at 20℃; for 24h;96%
In acetonitrile at 23℃; for 14h; enantioselective reaction;95%
With Co(salen) macrocycles 1(OTs) In tert-butyl methyl ether at 20℃; for 19h; optical yield given as %ee; enantioselective reaction;91%

108-39-4Related news

Oxidative degradation of m-Cresol (cas 108-39-4) using ozone in the presence of pure γ-Al2O3, SiO2 and V2O5 catalysts08/19/2019

The oxidative degradation of a potential pollutant, m-cresol with ozone was investigated both in the absence and presence of a catalyst. The oxidation reaction was studied as a function of time, where aliquots were drawn in every reaction from 3 to 24 h and dissolved in an absolute ethanol. The ...detailed

108-39-4Relevant articles and documents

Ene Reductase Enzymes for the Aromatisation of Tetralones and Cyclohexenones to Naphthols and Phenols

Kelly, Paul P.,Lipscomb, David,Quinn, Derek J.,Lemon, Ken,Caswell, Jill,Spratt, Jenny,Kosjek, Birgit,Truppo, Matthew,Moody, Thomas S.

, p. 731 - 736 (2016)

Ene reductases (EREDs) have great potential as oxidation biocatalysts, as demonstrated by their efficient conversion of a number of tetralones to the corresponding naphthols. Of 96 enzymes tested, 57 were able to produce 2-naphthol in this way. Further tests with substituted tetralones revealed typically high conversions up to >99%. The reactions were performed under mild conditions in aqueous buffer with only co-solvent, biocatalyst and oxidation substrate required for conversion. Production of a methoxy-substituted naphthol was also successfully performed on a gram scale, with 91% yield. This methodology provides a new avenue to produce substituted naphthols as valuable building blocks, with the possibility to extend the approach to the production of phenols also being demonstrated.

Postsynthetic metalation of bipyridyl-containing metal-organic frameworks for highly efficient catalytic organic transformations

Manna, Kuntal,Zhang, Teng,Lin, Wenbin

, p. 6566 - 6569 (2014)

We have designed highly stable and recyclable single-site solid catalysts via postsynthetic metalation of the 2,2-bipyridyl-derived metal-organic framework (MOF) of the UiO structure (bpy-UiO). The Ir-functionalized MOF (bpy-UiO-Ir) is a highly active catalyst for both borylation of aromatic C-H bonds using B2(pin)2 (pin = pinacolate) and ortho-silylation of benzylicsilyl ethers; the ortho-silylation activity of the bpy-UiO-Ir is at least 3 orders of magnitude higher than that of the homogeneous control. The Pd-functionalized MOF (bpy-UiO-Pd) catalyzes the dehydrogenation of substituted cyclohexenones to afford phenol derivatives with oxygen as the oxidant. Most impressively, the bpy-UiO-Ir was recycled and reused 20 times for the borylation reaction without loss of catalytic activity or MOF crystallinity. This work highlights the opportunity in designing highly stable and active catalysts based on MOFs containing nitrogen donor ligands for important organic transformations.

Continuous-flow generation of anhydrous diazonium species: Monolithic microfluidic reactors for the chemistry of unstable intermediates

Fortt, Robin,Wootton, Robert C. R.,De Mello, Andrew J.

, p. 762 - 768 (2003)

Monolithic microfluidic reactors for the safe, expedient, and continuous synthesis of products involving unstable intermediates were fabricated and assessed. The formation of diazonium salts in anhydrous conditions and their subsequent in situ chlorination within microfiuidic channels under hydrodynamic pumping regimes is presented. Significant enhancements in yield were observed due to enhanced heat and mass transfer in microfluidic systems. Analysis performed using off-line GC and GC-MS was compared with on-line, on-chip Raman spectroscopy for the direct determination of analytes.

One-pot synthesis of benzofurans via heteroannulation of benzoquinones

Pirouz, Maryam,Saeed Abaee,Harris, Pernille,Mojtahedi, Mohammad M.

, p. 24 - 31 (2021)

Three different reactions were explored leading to the synthesis of various benzofurans. All reactions took place under AcOH catalysis in a one-pot manner. As a result, benzoquinone derivatives underwent heteroannulation with either itself or cyclohexanones to produce furanylidene-benzofuran or benzofuran structures, respectively.

Photochemical Transformationos of Protonated Phenols. A One-Step Synthesis of Umbellulone from Thymol

Baeckstroem, Peter,Jacobsson, Ulla,Koutek, Bohumir,Norin, Torbjoern

, p. 3728 - 3732 (1985)

UV irradiation of thymol (7) at 254 or 300 nm in trifluoromethanesulfonic acid affords ten products, eight of which have been isolated and characterized.Four competitive processes are suggested to be operating in the formation of the photoproducts: (i) regioselective type A rearrangement leading to umbellulone (8, about 10percent, (ii) formal C2->C3 migration by type A rearrangement and ring opening which affords the principal products, 3-isopropyl-5-methylphenol (12, 17percent), (iii) intermolecular transalkylation leading to diisopropylphenols 13-15 (17percent), and (iv) formation ofpiperitenone (10, 5percent) initiated by hydrogen abstraction.A mechanism for the formation of 10 is proposed.Both para- and ortho-protonated 7 are suggested to be involved in product formation.

Palladium-Catalyzed Hydrodehalogenation of Haloaromatic Compounds

Pandey, Paras N.,Purkayastha, Makhan L.

, p. 876 - 878 (1982)

-

Aerobic dehydrogenation of cyclohexanone to phenol catalyzed by Pd(TFA)2/2-dimethylaminopyridine: Evidence for the role of Pd nanoparticles

Pun, Doris,Diao, Tianning,Stahl, Shannon S.

, p. 8213 - 8221 (2013)

We have carried out a mechanistic investigation of aerobic dehydrogenation of cyclohexanones and cyclohexenones to phenols with a Pd(TFA) 2/2-dimethylaminopyridine catalyst system. Numerous experimental methods, including kinetic studies, filtration tests, Hg poisoning experiments, transmission electron microscopy, and dynamic light scattering, provide compelling evidence that the initial PdII catalyst mediates the first dehydrogenation of cyclohexanone to cyclohexenone, after which it evolves into soluble Pd nanoparticles that retain catalytic activity. This nanoparticle formation and stabilization is facilitated by each of the components in the catalytic reaction, including the ligand, TsOH, DMSO, substrate, and cyclohexenone intermediate.

The multifunctional globin dehaloperoxidase strikes again: Simultaneous peroxidase and peroxygenase mechanisms in the oxidation of EPA pollutants

Ghiladi, Reza A.,Malewschik, Talita,McGuire, Ashlyn H.,de Serrano, Vesna

, (2019)

The multifunctional catalytic hemoglobin dehaloperoxidase (DHP) from the terebellid polychaete Amphitrite ornata was found to catalyze the H2O2-dependent oxidation of EPA Priority Pollutants (4-Me-o-cresol, 4-Cl-m-cresol and pentachlorophenol) and EPA Toxic Substances Control Act compounds (o-, m-, p-cresol and 4-Cl-o-cresol). Biochemical assays (HPLC/LC-MS) indicated formation of multiple oxidation products, including the corresponding catechol, 2-methylbenzoquinone (2-MeBq), and oligomers with varying degrees of oxidation and/or dehalogenation. Using 4-Br-o-cresol as a representative substrate, labeling studies with 18O confirmed that the O-atom incorporated into the catechol was derived exclusively from H2O2, whereas the O-atom incorporated into 2-MeBq was from H2O, consistent with this single substrate being oxidized by both peroxygenase and peroxidase mechanisms, respectively. Stopped-flow UV–visible spectroscopic studies strongly implicate a role for Compound I in the peroxygenase mechanism leading to catechol formation, and for Compounds I and ES in the peroxidase mechanism that yields the 2-MeBq product. The X-ray crystal structures of DHP bound with 4-F-o-cresol (1.42 ?; PDB 6ONG), 4-Cl-o-cresol (1.50 ?; PDB 6ONK), 4-Br-o-cresol (1.70 ?; PDB 6ONX), 4-NO2-o-cresol (1.80 ?; PDB 6ONZ), o-cresol (1.60 ?; PDB 6OO1), p-cresol (2.10 ?; PDB 6OO6), 4-Me-o-cresol (1.35 ?; PDB 6ONR) and pentachlorophenol (1.80 ?; PDB 6OO8) revealed substrate binding sites in the distal pocket in close proximity to the heme cofactor, consistent with both oxidation mechanisms. The findings establish cresols as a new class of substrate for DHP, demonstrate that multiple oxidation mechanisms may exist for a given substrate, and provide further evidence that different substituents can serve as functional switches between the different activities performed by dehaloperoxidase. More broadly, the results demonstrate the complexities of marine pollution where both microbial and non-microbial systems may play significant roles in the biotransformations of EPA-classified pollutants, and further reinforces that heterocyclic compounds of anthropogenic origin should be considered as environmental stressors of infaunal organisms.

Gold-Catalyzed Proto- and Deuterodeboronation

Barker, Graeme,Webster, Stacey,Johnson, David G.,Curley, Rachel,Andrews, Matthew,Young, Paul C.,MacGregor, Stuart A.,Lee, Ai-Lan

, p. 9807 - 9816 (2015)

A mild gold-catalyzed protodeboronation reaction, which does not require acid or base additives and can be carried out in "green" solvents, is described. As a result, the reaction is very functional-group-tolerant, even to acid- and base-sensitive functional groups, and should allow for the boronic acid group to be used as an effective traceless directing or blocking group. The reaction has also been extended to deuterodeboronations for regiospecific ipso-deuterations of aryls and heteroaryls from the corresponding organoboronic acid. Based on density functional theory calculations, a mechanism is proposed that involves nucleophilic attack of water at boron followed by rate-limiting B-C bond cleavage and facile protonolysis of a Au-σ-phenyl intermediate.

Cesium carbonate mediated aryl triflate esters' deprotection

Green, Alice E.,Agouridas, Vangelis,Deniau, Eric

, p. 7078 - 7079 (2013)

A variety of diversely substituted aryl triflate esters were efficiently deprotected to the parent phenols by exposure to cesium carbonate in toluene. This procedure proved highly compatible with existing functional groups.

Pd0-PyPPh2@porous organic polymer: Efficient heterogeneous nanoparticle catalyst for dehydrogenation of 3-methyl-2-cyclohexen-1-one without extra oxidants and hydrogen acceptors

Chen, Xingkun,Wang, Wenlong,Zhu, Hejun,Yang, Wenshao,Ding, Yunjie

, p. 49 - 56 (2018)

In this contribution, we have developed an efficient and recyclable porous organic polymer (POP) supported Pd nanoparticle catalyst (Pd°-PyPPh2@POP) for dehydrogenation of 3-methyl-2-cyclohexen-1-one. This heterogeneous catalytic system represents a totally clean process without using any extra oxidant and hydrogen acceptors. The SEM-EDS mapping images of the Pd°-PyPPh2@POP catalyst reveal the highly uniformly dispersed character of C, Pd, P and N elements. The coordination bonds between Pd nanoparticle and exposed P atom as well as N atom on the surface of PyPPh2@POP polymer are confirmed by means of solid-state 31P NMR and XPS. Importantly, both P atom and pyridyl ring on the PyPPh2@POP polymer are themselves used as solid base over the Pd°-PyPPh2@POP catalyst, leading to a catalytic conversion of 88.2% even without the employment of inorganic base additives (K2CO3). Our results have provided a strategy for designing highly active bifunctional POP supported nanoparticle catalysts.

Imidazolium-urea low transition temperature mixtures for the UHP-promoted oxidation of boron compounds

Martos, Mario,Pastor, Isidro M.

, (2022/01/03)

Different carboxy-functionalized imidazolium salts have been considered as components of low transition temperature mixtures (LTTMs) in combination with urea. Among them, a novel LTTM based on 1-(methoxycarbonyl)methyl-3-methylimidazolium chloride and urea has been prepared and characterized by differential scanning calorimetry throughout its entire composition range. This LTTM has been employed for the oxidation of boron reagents using urea-hydrogen peroxide adduct (UHP) as the oxidizer, thus avoiding the use of aqueous H2O2, which is dangerous to handle. This metal-free protocol affords the corresponding alcohols in good to quantitative yields in up to 5 mmol scale without the need of further purification. The broad composition range of the LTTM allows for the reaction to be carried out up to three consecutive times with a single imidazolium salt loading offering remarkable sustainability with an E-factor of 7.9, which can be reduced to 3.2 by the threefold reuse of the system.

Highly selective demethylation of anisole to phenol over H4Nb2O7modified MoS2catalyst

Ji, Na,Wang, Zhenjiao,Diao, Xinyong,Jia, Zhichao,Li, Tingting,Zhao, Yujun,Liu, Qingling,Lu, Xuebin,Ma, Degang,Song, Chunfeng

, p. 800 - 809 (2021/02/26)

Hydrogenolysis of lignin to obtain value-added phenolic chemicals is an important approach for its comprehensive utilization. Herein, H4Nb2O7modified MoS2catalyst with short slabs and narrow stacking degree was successfully synthesized by the one step hydrothermal method and used in the selective demethylation of anisole to phenol. The MoS2-H4Nb2O7-160 catalyst exhibited the best activity with 97.7% conversion of anisole and 98.0% selectivity of phenol under 3 MPa H2pressure at 270 °C for 4 h, which has been rarely reported on anisole transformation over heterogeneous catalysts so far. The characterizations results demonstrated that the H4Nb2O7modification reduced the slab length and stacking degree of MoS2during the hydrothermal process and enhanced the acidity property therefore improved the cleavage ability of CArO-CH3bond. This study provides a new scheme for the activity enhancement of MoS2in lignin demethylation, laying a foundation on the improvement of lignin utilization and the development of renewable energy strategy.

Photocatalytic synthesis of phenols mediated by visible light using KI as catalyst

Huiqin, Wei,Wu, Mei

supporting information, (2021/11/30)

A transition-metal-free hydroxylation of iodoarenes to afford substituted phenols is described. The reaction is promoted by KI under white LED light irradiation and uses atmospheric oxygen as oxidant. By the use of triethylamine as base and solvent, the corresponding phenols are obtained in moderate to good yields. Mechanistic studies suggest that KI and catalysis synergistically promote the cleavage of C-I bond to form free aryl radicals.

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