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106-44-5 Usage

General Description

4-methylphenol, also known as p-cresol, is a chemical compound with the formula C7H8O. It is a colorless to yellowish liquid with a sweet, smoky odor. 4-methylphenol is a derivative of phenol and is commonly found as a component of coal tar and as a byproduct of chemical processes. It is used in the production of various industrial chemicals and as a precursor for the synthesis of pharmaceuticals and dyes. 4-methylphenol is also used as a disinfectant and antiseptic, and in the formulation of fragrances and flavorings. It is considered to be toxic if ingested or inhaled, and can cause irritation to the skin and eyes.

Check Digit Verification of cas no

The CAS Registry Mumber 106-44-5 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 6 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 106-44:
(5*1)+(4*0)+(3*6)+(2*4)+(1*4)=35
35 % 10 = 5
So 106-44-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3

106-44-5 Well-known Company Product Price

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

  • (A13531)  p-Cresol, 99%   

  • 106-44-5

  • 100g

  • 101.0CNY

  • Detail
  • Alfa Aesar

  • (A13531)  p-Cresol, 99%   

  • 106-44-5

  • 250g

  • 114.0CNY

  • Detail
  • Alfa Aesar

  • (A13531)  p-Cresol, 99%   

  • 106-44-5

  • 1000g

  • 283.0CNY

  • Detail
  • Alfa Aesar

  • (A13531)  p-Cresol, 99%   

  • 106-44-5

  • 5000g

  • 1242.0CNY

  • Detail
  • Sigma-Aldrich

  • (61030)  p-Cresol  puriss. p.a., ≥99.0% (GC)

  • 106-44-5

  • 61030-25G-F

  • 455.13CNY

  • Detail
  • Sigma-Aldrich

  • (61030)  p-Cresol  puriss. p.a., ≥99.0% (GC)

  • 106-44-5

  • 61030-500G-F

  • 3,106.35CNY

  • Detail
  • Sigma-Aldrich

  • (42429)  p-Cresol  analytical standard

  • 106-44-5

  • 42429-5G-F

  • 307.71CNY

  • Detail
  • Supelco

  • (442418)  4-Methylphenol  analytical standard

  • 106-44-5

  • 000000000000442418

  • 234.00CNY

  • Detail
  • Supelco

  • (40252-U)  4-Methylphenolsolution  certified reference material, 5000 μg/mL in methanol

  • 106-44-5

  • 40252-U

  • 533.52CNY

  • Detail

106-44-5SDS

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 p-cresol

1.2 Other means of identification

Product number -
Other names Phenol, 4-methyl-

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:106-44-5 SDS

106-44-5Synthetic route

4-cyanophenol
767-00-0

4-cyanophenol

p-cresol
106-44-5

p-cresol

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;92%
With kieselguhr; nickel-copper at 453℃; Hydrogenation;
With ethanol at 24.84℃; for 48h; Photolysis; Inert atmosphere;99 %Chromat.
With [RuCl2(p-cymene)(P(Fur)3)] In water at 80℃; for 2h; Catalytic behavior; Green chemistry;>99 %Chromat.
1-acetoxy-4-methylbenzene
140-39-6

1-acetoxy-4-methylbenzene

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
silica gel; toluene-4-sulfonic acid In water; toluene at 80℃; for 8h;100%
With ammonium acetate In methanol at 20℃; for 4.5h;97%
With mesoporous silica-supported (Salen) Co(II) catalyst In methanol at 20℃; for 1h; chemoselective reaction;95%
4-acetyl-4-methyl-6-phenylselenocyclohex-2-enone
97400-46-9, 97400-47-0

4-acetyl-4-methyl-6-phenylselenocyclohex-2-enone

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With dihydrogen peroxide In dichloromethane at 0℃; for 2h;100%
4-(tert-butoxy)toluene
15359-98-5

4-(tert-butoxy)toluene

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With sodium iodide; cerium(III) chloride In acetonitrile at 40℃; for 3h;100%
In methanol at 25℃; Kinetics; Quantum yield; Decomposition; Irradiation;
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With hydrogen In water at 25℃; for 1h;99%
With palladium 10% on activated carbon; water; hydrazine hydrate In ethanol at 100℃; for 24h; Reagent/catalyst;99%
With [(C6H6)(PCy3)(CO)RuH]+*BF4−; hydrogen; phenol In 1,4-dioxane; isopropyl alcohol at 130℃; under 1520.1 Torr; for 12h; Inert atmosphere; Glovebox; Schlenk technique; chemoselective reaction;90%
trimethyl(4-methylphenoxy)silane
17902-32-8

trimethyl(4-methylphenoxy)silane

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With water; bis(benzonitrile)palladium(II) dichloride for 0.05h; desilylation; microwave irradiation;99%
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0666667h; Green chemistry;98%
With rice husk ash supported on anatase-phase titania nanoparticles nanocomposite In methanol at 20℃; for 0.05h;94%
tert-Butyl(dimethyl)-(4-methylphenoxy)silane
62790-85-6

tert-Butyl(dimethyl)-(4-methylphenoxy)silane

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With potassium hydrogen difluoride; 18-crown-6 ether In acetonitrile at 20℃; for 24h;99%
With sodium phosphate dodecahydrate In N,N-dimethyl-formamide at 20℃; for 1.8h;97%
With SO3H silica gel In n-heptane at 50℃; for 0.5h;96%
4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 24h; Green chemistry;99%
With water In tetrahydrofuran at 100℃; for 12h;99%
With dihydrogen peroxide at 30℃; for 5h; Green chemistry;98%
1-(methoxymethoxy)-4-methylbenzene
25458-49-5

1-(methoxymethoxy)-4-methylbenzene

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 1.5h;99%
With tin(IV) chloride In dichloromethane at 0℃; for 0.0333333h;95%
4-tolyl iodide
624-31-7

4-tolyl iodide

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With 2-(N,N-dimethylamino)ethanol; sodium hydroxide; silver(l) oxide In water; dimethyl sulfoxide at 100℃; for 24h; Reagent/catalyst;99%
Stage #1: 4-tolyl iodide With copper(l) iodide; 2-methyl-8-quinolinol; tetra(n-butyl)ammonium hydroxide In water; dimethyl sulfoxide at 100℃; for 7h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃;
97%
Stage #1: 4-tolyl iodide 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;
96%
(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

A

p-cresol
106-44-5

p-cresol

B

C6H10O

C6H10O

Conditions
ConditionsYield
With palladium dichloride In methanol at 40℃; for 24h; Inert atmosphere; Green chemistry; chemoselective reaction;A 99%
B 99%
p-Chlor-cinnamyl-p-tolyl-ether
92907-14-7

p-Chlor-cinnamyl-p-tolyl-ether

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With ethylmagnesium chloride; iron(II) chloride In tetrahydrofuran; m-xylene at 20℃; for 1h;99%
2-(4-methylphenoxy)ethanol
15149-10-7

2-(4-methylphenoxy)ethanol

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 100℃; for 3h; Schlenk technique;99%
2-(4-methylphenoxy)tetrahydro-2H-pyran
13481-09-9

2-(4-methylphenoxy)tetrahydro-2H-pyran

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With methanol at 20℃; for 0.5h;98%
With Montmorillonite KSF In methanol at 40 - 50℃; for 0.4h;97%
With methanol; zirconium(IV) chloride at 20℃; for 2h;97%
allyl p-tolyl ether
23431-48-3

allyl p-tolyl ether

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 0.0333333h;98%
With ethylmagnesium chloride; iron(II) chloride In tetrahydrofuran; m-xylene at 20℃; for 1h;97%
With iodine at 20℃;92%
With tetrachlorosilane; borontrifluoride acetic acid; lithium iodide In toluene; acetonitrile at 70℃; for 6h;90%
With 12-TPA/SBA 15 In 1,4-dioxane at 110℃;74%
4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;98%
4-(p-tolyloxy)butan-1-ol
60222-64-2

4-(p-tolyloxy)butan-1-ol

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 100℃; for 3h; Schlenk technique;98%
4-Methylanisole
104-93-8

4-Methylanisole

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With 1,3-dimethyl-2-imidazolidinone; lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 185℃; for 12h; further reagent: NaN(SiMe3)2; various temperatures - 65-185 deg C;97%
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; N-methylaniline In diethyl ether; xylene at 120℃; for 6.5h;95%
With copper(I) oxide; sodium methylate In methanol at 185℃; for 12h; Autoclave;89%
tert-Butyl(dimethyl)-(4-methylphenoxy)silane
62790-85-6

tert-Butyl(dimethyl)-(4-methylphenoxy)silane

Cs2CO3

Cs2CO3

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 20℃; for 2.5h;97%
4-Methyl-4-nitro-pentanoic acid p-tolyl ester

4-Methyl-4-nitro-pentanoic acid p-tolyl ester

A

1-Hydroxy-5,5,-dimethyl-1-pyrolid-2-one
5165-27-5

1-Hydroxy-5,5,-dimethyl-1-pyrolid-2-one

B

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With ammonium chloride; zinc In methanol Heating;A n/a
B 96%
2,6-di-tert-butyl-4-methyl-phenol
128-37-0

2,6-di-tert-butyl-4-methyl-phenol

A

p-cresol
106-44-5

p-cresol

B

4-tert-butyltoluene
98-51-1

4-tert-butyltoluene

Conditions
ConditionsYield
With Nafion-H; toluene for 2h; Heating;A 96%
B 94 % Chromat.
2,6-di-tert-butyl-4-methyl-phenol
128-37-0

2,6-di-tert-butyl-4-methyl-phenol

toluene
108-88-3

toluene

A

p-cresol
106-44-5

p-cresol

B

4-tert-butyltoluene
98-51-1

4-tert-butyltoluene

Conditions
ConditionsYield
With Nafion-H for 2h; Heating;A 96%
B 94 % Chromat.
2-thioxo-benzooxazole-3-carboximidic acid p-tolyl ester
70989-48-9

2-thioxo-benzooxazole-3-carboximidic acid p-tolyl ester

A

benzo[d]oxazole-2-(3H)-thione
2382-96-9

benzo[d]oxazole-2-(3H)-thione

B

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In ethanol for 0.5h; Heating;A 95%
B n/a
With hydrogenchloride for 7h; Heating;A 93%
B n/a
3,3-diethyl-1-(4-methylphenyl)-1-triazene
36719-51-4

3,3-diethyl-1-(4-methylphenyl)-1-triazene

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With water; sulfonic acid resin (H+ form) In acetonitrile for 0.166667h; Heating;95%
6,6-bis(4-methylphenyl)-3-methyl-1,2-dioxan-3-ol
142605-86-5

6,6-bis(4-methylphenyl)-3-methyl-1,2-dioxan-3-ol

A

p-cresol
106-44-5

p-cresol

B

1-[4-(methyl)phenyl]pentane-1,4-dione
13901-86-5

1-[4-(methyl)phenyl]pentane-1,4-dione

Conditions
ConditionsYield
With hydrogenchloride In acetic acid at 80℃; for 0.333333h;A 95%
B 67%
4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

acetonitrile complex of hypofluorous acid

acetonitrile complex of hypofluorous acid

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
In dichloromethane at 20℃;95%
C30H22O12P2S2W2

C30H22O12P2S2W2

A

p-cresol
106-44-5

p-cresol

B

C22H16O11P2W2

C22H16O11P2W2

Conditions
ConditionsYield
With dimanganese decacarbonyl In toluene at 20℃; for 6h; Inert atmosphere; Schlenk technique;A 94%
B 95%
2-bromo-p-cresol
6627-55-0

2-bromo-p-cresol

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane; ethanethiol at 0℃; for 0.5h;94.3%
With sodium hydroxide; nickel at 150℃; under 7600 Torr; Hydrogenation;
para-bromotoluene
106-38-7

para-bromotoluene

p-cresol
106-44-5

p-cresol

Conditions
ConditionsYield
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;94%
Stage #1: para-bromotoluene With copper(l) iodide; 2-methyl-8-quinolinol; tetra(n-butyl)ammonium hydroxide In water; dimethyl sulfoxide at 130℃; for 21h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃;
93%
Stage #1: para-bromotoluene 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;
93%
p-cresol
106-44-5

p-cresol

p-methylcyclohexanol
589-91-3

p-methylcyclohexanol

Conditions
ConditionsYield
With hydrogen In water at 20℃; under 7500.75 Torr; for 6h; Autoclave;100%
With nickel(II) oxide; hydrogen; palladium In hexane at 80℃; under 7500.75 Torr; for 10h;99%
With hydrogen; palladium on activated charcoal In hexane at 120℃; under 37503 Torr; Rate constant; var. solvents;
p-cresol
106-44-5

p-cresol

2-bromo-p-cresol
6627-55-0

2-bromo-p-cresol

Conditions
ConditionsYield
With hydrogen bromide; acetic acid In dimethyl sulfoxide at 20℃; for 2h;100%
With Oxone; potassium bromide In methanol at 20℃; for 4h;99%
With N-Bromosuccinimide; sulfonic acid functionalized silica In diethyl ether; acetonitrile at 20℃; for 0.166667h;99%
p-cresol
106-44-5

p-cresol

2,6-dinitro-p-cresol
609-93-8

2,6-dinitro-p-cresol

Conditions
ConditionsYield
With (NH4)2Ce(NO3)6 supported on pillared bentonite In water at 25℃; for 48h;100%
With chloro-trimethyl-silane; copper(ll) sulfate pentahydrate; guanidine nitrate In acetonitrile at 20℃;99%
With silica-acetate; dinitrogen tetraoxide In ethyl acetate for 0.333333h; Heating;95%
p-cresol
106-44-5

p-cresol

acetic anhydride
108-24-7

acetic anhydride

1-acetoxy-4-methylbenzene
140-39-6

1-acetoxy-4-methylbenzene

Conditions
ConditionsYield
With pyridine at 100℃; for 15h;100%
at 20℃; for 0.666667h;100%
With pyridine at 25℃; for 12h;100%
p-cresol
106-44-5

p-cresol

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

1-bromomethyl-4-nitro-benzene

4-methylphenyl 4-nitrobenzyl ether
67565-47-3

4-methylphenyl 4-nitrobenzyl ether

Conditions
ConditionsYield
With sodium hydroxide In water for 0.00277778h; microwave irradiation;100%
With sodium hydroxide; Aliquat 360 In dichloromethane; water at 25℃; for 24h;89%
With potassium carbonate; acetone
With alkaline solution
p-cresol
106-44-5

p-cresol

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

4-methylphenyl trifluoroacetate
1813-29-2

4-methylphenyl trifluoroacetate

Conditions
ConditionsYield
erbium(III) triflate In acetonitrile at 20℃; for 8h;100%
at 100℃; Cooling with ice;93%
p-cresol
106-44-5

p-cresol

3,5-dinitrobenoyl chloride
99-33-2

3,5-dinitrobenoyl chloride

3,5-dinitrobenzoate of 4-methylphenol
27563-96-8

3,5-dinitrobenzoate of 4-methylphenol

Conditions
ConditionsYield
With pyridine In tetrahydrofuran for 0.333333h; Heating;100%
With pyridine
Stage #1: p-cresol With base
Stage #2: 3,5-dinitrobenoyl chloride phase transfer; Further stages.;
p-cresol
106-44-5

p-cresol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

4-tolyl mesylate
17177-63-8

4-tolyl mesylate

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;91%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;80%
p-cresol
106-44-5

p-cresol

propargyl bromide
106-96-7

propargyl bromide

1-methyl-4-(2-propynyloxy)benzene
5651-90-1

1-methyl-4-(2-propynyloxy)benzene

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;100%
Stage #1: p-cresol With potassium carbonate In N,N-dimethyl-formamide for 0.166667h; Schlenk technique; Inert atmosphere;
Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 24h; Schlenk technique; Inert atmosphere;
99%
With caesium carbonate In acetonitrile93%
p-cresol
106-44-5

p-cresol

Bromoacetaldehyde diethyl acetal
2032-35-1

Bromoacetaldehyde diethyl acetal

1-(2,2-diethoxyethoxy)-4-methylbenzene
66614-56-0

1-(2,2-diethoxyethoxy)-4-methylbenzene

Conditions
ConditionsYield
Stage #1: p-cresol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h;
Stage #2: Bromoacetaldehyde diethyl acetal In N,N-dimethyl-formamide; mineral oil Reflux;
100%
Stage #1: p-cresol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: Bromoacetaldehyde diethyl acetal In N,N-dimethyl-formamide at 120℃; for 6h; Inert atmosphere;
98%
With potassium hydroxide In N,N-dimethyl acetamide at 20℃; Heating;96%
p-cresol
106-44-5

p-cresol

2,6-dideuterio-4-methylphenol
2876-02-0

2,6-dideuterio-4-methylphenol

Conditions
ConditionsYield
With perchloric acid; d(4)-methanol at 75℃; for 144h; Inert atmosphere;100%
With water-d2; phosphorus tribromide for 5h; Yield given;
With water-d2; phosphorus tribromide Reflux;
p-cresol
106-44-5

p-cresol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-Butyl(dimethyl)-(4-methylphenoxy)silane
62790-85-6

tert-Butyl(dimethyl)-(4-methylphenoxy)silane

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h;99%
With 1H-imidazole; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 2h;97%
p-cresol
106-44-5

p-cresol

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

methyl p-tolyloxyacetate
38768-63-7

methyl p-tolyloxyacetate

Conditions
ConditionsYield
With potassium carbonate In butanone for 5.5h; Heating;100%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;90%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;90%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;85%
With potassium carbonate In tetrahydrofuran at 20 - 80℃;
p-cresol
106-44-5

p-cresol

1,1,3,3-tetramethyldisilazane
15933-59-2

1,1,3,3-tetramethyldisilazane

Dimethyl-p-tolyloxy-silane
76058-60-1

Dimethyl-p-tolyloxy-silane

Conditions
ConditionsYield
100%
at 20 - 160℃; for 2h; Inert atmosphere;
p-cresol
106-44-5

p-cresol

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

1-(methoxymethoxy)-4-methylbenzene
25458-49-5

1-(methoxymethoxy)-4-methylbenzene

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 26h;100%
Stage #1: p-cresol With sodium hydride In N,N-dimethyl-formamide; paraffin oil at 0 - 20℃; for 1h;
Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; paraffin oil at 20℃; for 24h;
100%
(i) NaH, DMF, (ii) /BRN= 505943/; Multistep reaction;
p-cresol
106-44-5

p-cresol

2-chloro-2,2-difluoroacetic acid
76-04-0

2-chloro-2,2-difluoroacetic acid

difluoro-(4-methylphenoxy)acetic acid
207803-79-0

difluoro-(4-methylphenoxy)acetic acid

Conditions
ConditionsYield
With sodium hydride In 1,4-dioxane for 3h; Heating;100%
p-cresol
106-44-5

p-cresol

2-Iodobenzyl bromide
40400-13-3

2-Iodobenzyl bromide

1-iodo-2-(4-methylphenoxymethyl)benzene

1-iodo-2-(4-methylphenoxymethyl)benzene

Conditions
ConditionsYield
With potassium carbonate In acetone at 50℃;100%
Stage #1: p-cresol With potassium carbonate In N,N-dimethyl-formamide for 0.166667h;
Stage #2: 2-Iodobenzyl bromide In N,N-dimethyl-formamide at 20℃;
62%
Stage #1: p-cresol With sodium hydride In tetrahydrofuran for 0.5h; Metallation; Heating;
Stage #2: 2-Iodobenzyl bromide In tetrahydrofuran for 4h; Etherification; Heating; Further stages.;
40%
p-cresol
106-44-5

p-cresol

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1-(tert-butoxycarbonyloxy)-4-methylbenzene
104741-75-5

1-(tert-butoxycarbonyloxy)-4-methylbenzene

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 0.25h; Product distribution; Further Variations:; Reagents; reaction time; Condensation;100%
With mesoporous silica MCM-41 supported erbium(III) at 40℃; for 1.5h; Neat (no solvent); ultrasound irradiation; Inert atmosphere;99%
With MgO-ZrO2 nanoparticle at 60℃; for 1.5h; neat (no solvent); chemoselective reaction;92%
p-cresol
106-44-5

p-cresol

3,5-dinitrobenzotrifluoride
401-99-0

3,5-dinitrobenzotrifluoride

4'-methyl-3-nitro-5-trifluoromethyldiphenyl ether

4'-methyl-3-nitro-5-trifluoromethyldiphenyl ether

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 98℃; for 3h;100%
With potassium carbonate In N,N-dimethyl-formamide
p-cresol
106-44-5

p-cresol

1-fluoro-3-(trifluoromethyl)-5-nitrobenzene
454-73-9

1-fluoro-3-(trifluoromethyl)-5-nitrobenzene

4'-methyl-3-nitro-5-trifluoromethyldiphenyl ether

4'-methyl-3-nitro-5-trifluoromethyldiphenyl ether

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 98℃; for 3h;100%
With potassium carbonate In N,N-dimethyl-formamide
p-cresol
106-44-5

p-cresol

1,1,1,2,2,2-hexamethyldisilane
1450-14-2

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

trimethyl(4-methylphenoxy)silane
17902-32-8

trimethyl(4-methylphenoxy)silane

Conditions
ConditionsYield
In pyridine at 115℃; for 3h;100%
With lanthanum(III) nitrate hexahydrate In acetonitrile at 20℃;90%
p-cresol
106-44-5

p-cresol

(permethylcyclopentadienyl-methoxo-ruthenium)2

(permethylcyclopentadienyl-methoxo-ruthenium)2

trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

{C5Me5Ru(μ6-4-MeC6H4OH)}CF3SO3

{C5Me5Ru(μ6-4-MeC6H4OH)}CF3SO3

Conditions
ConditionsYield
In dichloromethane under Ar: addn. of CF3SO3H to a stirred dichloromethane soln. of ((C5(CH3)5)RuOCH3)2; stirring for 15 min at room temperature; addn. of a soln. of p-cresol in dichloromethane; stirring for 2 h;; removing of the solvent; crystallization from dichloromethane/diethyl ether; elem. anal.;100%
p-cresol
106-44-5

p-cresol

trimesitylgermylamine
139925-54-5

trimesitylgermylamine

trimesitylgermylparamethylphenoxide
139925-56-7

trimesitylgermylparamethylphenoxide

Conditions
ConditionsYield
In benzene addn. of p-cresol to the Ge compd. in benzene (inert gas) and heating at 120°C for 2 h; evapn. (vac.); elem. anal.;;100%
In neat (no solvent) addn. of p-cresol to the Ge compd. in a Schlenk tube (inert gas) and heating at 166-195°C for ca. 1 h; evapn. (vac.); elem. anal.;;
In not given byproducts: NH3;
p-cresol
106-44-5

p-cresol

tetramethyl-diphosphine disulphide
3676-97-9

tetramethyl-diphosphine disulphide

A

dimethylphosphine sulfide
6591-05-5

dimethylphosphine sulfide

B

O-(p-tolyl) dimethylphosphinothioate
5553-03-7

O-(p-tolyl) dimethylphosphinothioate

Conditions
ConditionsYield
With hydridotetakis(triphenylphosphine)rhodium(I); 1,2-bis(dimethylphosphanyl)ethane In tetrahydrofuran for 3h; Inert atmosphere; Reflux;A n/a
B 100%
p-cresol
106-44-5

p-cresol

2,4-dinitrophenyl benzoate
1523-15-5

2,4-dinitrophenyl benzoate

A

p-cresyl benzoate
614-34-6

p-cresyl 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

106-44-5Relevant articles and documents

-

Cerny,Malek

, p. 1739 (1969)

-

CoMo sulfide-catalyzed hydrodeoxygenation of lignin model compounds: An extended reaction network for the conversion of monomeric and dimeric substrates

Jongerius, Anna L.,Jastrzebski, Robin,Bruijnincx, Pieter C.A.,Weckhuysen, Bert M.

, p. 315 - 323 (2012)

In the present work, extensive hydrodeoxygenation (HDO) studies with a commercial sulfided CoMo/Al2O3 catalyst were performed on a library of lignin model compounds at 50 bar hydrogen pressure and 300 °C in dodecane, using a batch autoclave system. The catalyst was activated under hydrogen atmosphere prior to the reaction, and the spent catalyst was analyzed using thermogravimetric analysis. An extended reaction network is proposed, showing that HDO, demethylation, and hydrogenation reactions take place simultaneously. HDO of mono-oxygenated substrates proved to be difficult at the applied conditions. Starting from most positions in the network, phenol, and cresols are therefore the main final products, suggesting the possibility of convergence on a limited number of products from a mixture of substrates. HDO of dimeric model compounds mimicking typical lignin linkages revealed that coumaran alkyl ethers and β-O-4 bonds can be broken, but 5-5′ linkages not.

Characteristic Effect of Pyridine on the NIH Shift and Selectivity in the Monooxygenation of Aromatic Compounds Catalyzed by a Nonheme Iron Complex/Hydroquinones/O2 System

Funabiki, Takuzo,Toyoda, Takehiro,Yoshida, Satohiro

, p. 1279 - 1282 (1992)

The high values of the NIH and Me-NIH shifts were observed in the hydroxylation of aromatic compounds such as toluene and xylenes with O2 by the catalytic system in the title.The pyridine concentration greatly affected not only the NIH shift, but the selectivity to form phenols by hydroxylation of the aromatic ring and to form aldehydes by oxidation of the methyl group.

-

Kaeding et al.

, p. 805,806 (1961)

-

Aerobic homocoupling of phenylboronic acid on Mg-Al mixed-oxides-supported Au nanoparticles

Wang, Liang,Wang, Hong,Zhang, Wei,Zhang, Jian,Lewis, James P.,Meng, Xiangju,Xiao, Feng-Shou

, p. 186 - 197 (2013)

Au nanoparticles are highly dispersed on Mg-Al mixed oxides by anion exchange (Au/MAO-AE) and homogeneous deposition-precipitation (Au/MAO-HDP). The XRD, UV-visible, and XPS spectra demonstrate that the Au species on both samples are present as metallic Au. The Au nanoparticles are directly confirmed by the transmission electron microscopy images. Very importantly, both Au/MAO-AE and Au/MAO-HDP catalysts show superior catalytic activity, selectivities, and recyclabilities in the aerobic homocoupling of phenylboronic acid, yielding biphenyl and phenol. During this reaction, H2O molecules from the system and hydroxyl groups on Mg-Al mixed oxides strongly influence the catalytic performance. Based on the catalytic data and XPS characterizations, a mechanism for aerobic homocoupling of phenylboronic on metallic Au nanoparticles is proposed. These catalytic data are in good agreement with those obtained from theoretical calculations.

One step phenol synthesis from benzene catalysed by nickel(ii) complexes

Muthuramalingam, Sethuraman,Anandababu, Karunanithi,Velusamy, Marappan,Mayilmurugan, Ramasamy

, p. 5991 - 6001 (2019)

Nickel(ii)complexes of N4-ligands have been synthesized and characterized as efficient catalysts for the hydroxylation of benzene using H2O2. All the complexes exhibited Ni2+ → Ni3+ oxidation potentials of around 0.966-1.051 V vs. Ag/Ag+ in acetonitrile. One of the complexes has been structurally characterized and adopted an octahedral coordination geometry around the nickel(ii) center. The complexes catalysed direct benzene hydroxylation using H2O2 as an oxygen source and afforded phenol up to 41% with a turnover number (TON) of 820. This is unprecedentedly the highest catalytic efficiency achieved to date for benzene hydroxylation using 0.05 mol% catalyst loading and five equivalents of H2O2. The benzene hydroxylation reaction possibly proceeds via the key intermediate bis(μ-oxo)dinickel(iii) species, which was characterized by HR-MS, vibrational and electronic spectral methods, for almost all complexes. The formation constant of the key intermediate was calculated to be 5.61-9.41 × 10-2 s-1 by following the appearance of an oxo-to-Ni(iii) LMCT band at around 406-413 nm. The intermediates are found to be very short-lived (t1/2, 73-123 s). The geometry of one of the catalytically active intermediates was optimized by DFT and its spectral properties were calculated by TD-DFT calculations, which are comparable to experimental spectral data. The kinetic isotope effect (KIE) values (0.98-1.05) support the involvement of nickel-bound oxygen species as an intermediate. The isotope-labeling experiments using H218O2 showed 92.46% incorporation of 18O, revealing that H2O2 is the key oxygen supplier to form phenol. The catalytic efficiencies of complexes are strongly influenced by the geometrical configuration of intermediates, and stereoelectronic and steric properties, which are fine-tuned by the ligand architecture.

-

Baddeley

, (1944)

-

Synthesis and antiradical activity of hybrid antioxidants based on isobornylphenols

Chukicheva, I. Yu.,Sukrusheva,Mazaletskaya,Kuchin

, (2016)

Alkylation of isobornylphenols with allylbenzene in the presence of homogeneous and heterogeneous catalysts of different nature has been studied. The maximum yield of phenols containing isobornyl and 1-phenylpropyl moieties has been achieved in the presen

Kinetics of Electron-transfer Reactions of para-Substituted Phenols p-C6H4(X)OH with 3+ (phen = 1,10-phenantroline) and with 2- in Aqueous Acidic Solutions: Correlation between the Hammett Constant of X and the One-electron Redox Potential of p-C6H4(X)OH

Kimura, Masaru,Kaneko, Yukari

, p. 341 - 343 (1984)

Kinetic Studies of the electron-transfer reactions of p-C6H4(X)OH (X= H, OCH3, OH, NH2, or NH3+ with tris(1,10-phenanrtoline)iron(III), 3+, and with hexachloroiridate(IV), 2-, have been made in aqueous acidic solutions.The second-order rate constants (k0) follow the rate law -d/dt = k0, where A is the one-electron acceptor 3+ or 2-, and were determined at an ionic strength of 1.0 mol dm-3 and 25 deg C.The order of the forward rate constants (kf) for the one-electron transfer step, which are defined as k0 = 2kf for the other X, was H + 3+ and 1 : 150 : 75 : 4x1E4 : 7.2x1E4 : 1.0x1E8 in the case of the 2- reactions.By applying Marcus theory to kf, standard redox potentials for the radical cations p-C6H4(X)OH.+ were estimated and found to be well correlated with the Hammett constants (?p) for the para substituents X.

Strong Visible-Light-Absorbing Cuprous Sensitizers for Dramatically Boosting Photocatalysis

Chen, Kai-Kai,Guo, Song,Li, Xiyou,Liu, Heyuan,Lu, Tong-Bu,Zhang, Zhi-Ming

, p. 12951 - 12957 (2020)

Developing strong visible-light-absorbing (SVLA) earth-abundant photosensitizers (PSs) for significantly improving the utilization of solar energy is highly desirable, yet it remains a great challenge. Herein, we adopt a through-bond energy transfer (TBET) strategy by bridging boron dipyrromethene (Bodipy) and a CuI complex with an electronically conjugated bridge, resulting in the first SVLA CuI PSs (Cu-2 and Cu-3). Cu-3 has an extremely high molar extinction coefficient of 162 260 m?1 cm?1 at 518 nm, over 62 times higher than that of traditional CuI PS (Cu-1). The photooxidation activity of Cu-3 is much greater than that of Cu-1 and noble-metal PSs (Ru(bpy)32+ and Ir(ppy)3+) for both energy- and electron-transfer reactions. Femto- and nanosecond transient absorption and theoretical investigations demonstrate that a “ping-pong” energy-transfer process in Cu-3 involving a forward singlet TBET from Bodipy to the CuI complex and a backward triplet-triplet energy transfer greatly contribute to the long-lived and Bodipy-localized triplet excited state.

Catalytic activity of the anaerobic tyrosine lyase required for thiamine biosynthesis in Escherichia coli

Challand, Martin R.,Martins, Filipa T.,Roach, Peter L.

, p. 5240 - 5248 (2010)

Thiazole synthase in Escherichia coli is an αβ heterodimer of ThiG and ThiH. ThiH is a tyrosine lyase that cleaves the Cα-Cβ bond of tyrosine, generating p-cresol as a by-product, to form dehydroglycine. This reactive intermediate acts as one of three substrates for the thiazole cyclization reaction catalyzed by ThiG. ThiH is a radical S-adenosylmethionine (AdoMet) enzyme that utilizes a [4Fe-4S]+ cluster to reductively cleave AdoMet, forming methionine and a 5′-deoxyadenosyl radical. Analysis of the time-dependent formation of the reaction products 5′- deoxyadenosine (DOA) and p-cresol has demonstrated catalytic behavior of the tyrosine lyase. The kinetics of product formation showed a pre-steady state burst phase, and the involvement of DOA in product inhibition was identified by the addition of 5′-methylthioadenosine/S-adenosylhomocysteine nucleosidase to activity assays. This hydrolyzed the DOA and changed the rate-determining step but, in addition, substantially increased the uncoupled turnover of AdoMet. Addition of glyoxylate and ammonium inhibited the tyrosine cleavage reaction, but the reductive cleavage of AdoMet continued in an uncoupled manner. Tyrosine analogues were incubated with ThiGH, which showed a strong preference for phenolic substrates. 4-Hydroxyphenylpropionic acid analogues allowed uncoupled AdoMet cleavage but did not result in further reaction (Cα-Cβ bond cleavage). The results of the substrate analogue studies and the product inhibition can be explained by a mechanistic hypothesis involving two reaction pathways, a product-forming pathway and a futile cycle.

Cresol Izomerization in the Presence of Acid Catalysts

Tarasov,Dunaev,Kustov

, p. 262 - 264 (2018)

It is shown for toluene oxidation with nitrous oxide that modifying HZSM-5 zeolite with zinc oxide nanoparticles considerably improves the selectivity and yield of cresols. It is found that a 2% ZnO/HZSM-5 composite catalyst also exhibits enhanced and stable activity at high temperatures. For the o-cresol isomerization reaction, this modification of HZSM-5 zeolite greatly reduces the contribution from disproportionation and cracking reactions proceeding with formation of phenol, C6–C9 aromatic hydrocarbons, and xylenols. The regularities of their formation in the presence of the studied catalysts are determined using the results from thermodynamic calculations for the equilibrium concentrations of cresol isomers.

MCM-41-supported phosphotungstic acid-catalyzed cleavage of C-O bond in allyl aryl ethers

Sakate, Sachin S.,Kamble, Sumit B.,Chikate, Rajeev C.,Rode, Chandrashekhar V.

, p. 4943 - 4949 (2017)

Removal of the protecting allyl group from allyl aryl ethers in the presence of other oxygen protecting groups was successfully achieved using a solid acid supported on the high surface area material MCM-41. The catalyst showed excellent activity in the presence of various electron withdrawing, electron donating, and oxidizable functional groups. The methodology is also very useful for the removal of protecting allyl groups of various natural products such as vanillin, isovanillin, and other oxygen functionalized aldehydes and ketones.

Nickel-catalyzed cross-coupling of aryl grignard reagents with aromatic alkyl ethers: An efficient synthesis of unsymmetrical biaryls

Dankwardt, John W.

, p. 2428 - 2432 (2004)

New substrates for biaryl synthesis: aromatic ethers undergo nickel-catalyzed cross-coupling with aryl Grignard reagents to give unsymmetrical biaryls in excellent yields (see scheme). Both the nature of the nickel catalyst and the choice of solvent are crucial for reaching high levels of conversion.

Effects of ascorbic acid on arenediazonium salts reactivity: Kinetics and mechanism of the reaction

Costas-Costas, Ugo,Gonzalez-Romero, Elisa,Bravo-Diaz, Carlos

, p. 632 - 648 (2001)

We have examined the kinetics and mechanism of dediazoniation of o-, m- and p-methylbenzenediazonium (ArN2-) tetrafluoroborate in the presence of ascorbic acid (H2A) at different pHs by combining spectophotometric (VIS-UV), high performance liquid chromatography (HPLC), and polarographic measurements. Kinetic data show that, at low pH, observed rate constants increase linearly with increasing ascorbic acid concentration, but the saturation kinetics observed at higher pH suggest the formation of a transient diazo-ether complex preceding the slow step of the reaction. Experimental evidence for the formation of such a complex was obtained from a competitive coupling reaction with the Na salt of '2-naphthol-6-sulfonic acid' and by titration of ascorbic acid (H2A) with the arenediazonium ions (electrochemical measurements). HPLC Analysis of dediazoniation products indicates that, in the absence of H2A, only the heterolytic phenol derivative, ArOH, is formed quantitatively, in keeping with the predictions of the DN+AN mechanism. In the pH 2-4 range and in the presence of H2A, reduction products (ArH) are obtained in addition to heterolytic products (ArOH), corroborating that certain biological reducing agents like ascorbate (HA-) are capable of inducing reductive fragmentation of ArN2- into aryl radicals. All evidence is consistent with two competitive reaction pathways, the thermal decomposition of ArN2+, and a rate-limiting decomposition of the transient diazo ether 'complex', formed during the reaction of ArN2+ with HA- in a rapid pre-equilibrium step.

A MODEL FOR METABOLIC ACTIVATION OF DIALKYLNITROSAMINES. OXIDATIVE DEALKYLATION OF N-NITROSO-2-(ALKYLAMINO)ACETONITRILE BY FLAVIN MIMIC IN AQUEOUS SOLUTION

Yano, Yumihiko,Yokoyama, Takeshi,Yoshida, Kitaro

, p. 5121 - 5124 (1986)

Oxidation-active flavin mimic, benzodipteridine (BDP), is found to react with N-nitroso-2-(alkylamino)acetonitrile via oxidative dealkylation in aqueous solution.From the kinetic investigations, the oxidation mechanism is proposed.

Comparison of neurotoxic effects and potential risks from oral administration or ingestion of tricresyl phosphate and jet engine oil containing tricresyl phosphate

Mackerer, Carl R.,Barth, Mary L.,Krueger, Andrew J.,Chawla, Birbal,Roy, Timothy A.

, p. 293 - 328 (1999)

Neurotoxicity of tricresyl phosphates (TCPs) and jet engine oil (JEO) containing TCPs were evaluated in studies conducted in both rat and hen. Results for currently produced samples ('conventional' and 'low-toxicity') were compared with published findings on older samples to identify compositional changes and relate those changes to neurotoxic potential. Finally, a human risk assessment for exposure by oral ingestion of currently produced TCPs in JEO at 3% (JEO + 3%) was conducted. TCPs and certain other triaryl phosphates administered as single doses inhibited brain neuropathy target esterase (B-NTE; neurotoxic esterase) in the rat and the hen (hen 3.25 times as sensitive), and both species were deemed acceptable for initial screening purposes. Neither rat nor hen was sensitive enough to detect statistically significant inhibition of B-NTE after single doses of JEO + 3% 'conventional' TCP. Subacute administration of 2 g/kg/d of JEO + 3% 'conventional' TCP to the hen produced B-NTE inhibition 132%), which did not result in organophosphorus-induced delayed neurotoxicity (OPIDN). Subchronic administration of JEO + 3% TCP but not JEO + 1% TCP at 2 g/kg/d produced OPIDN. Thus, the threshold for OPIDN was between 20 and 60 mg 'conventional' TCP/kg/d in JEO for 10 wk. The current 'conventional' TCPs used in JEO and new 'low-toxicity' TCPs now used in some JEO are synthesized from phenolic mixtures having reduced levels of ortho-cresol and ortho-xylenols resulting in TCPs of very high content of meta- and para-substituted phenyl moieties; this change in composition results in lower toxicity. The 'conventional' TCPs still retain enough inhibitory activity to produce OPIDN, largely because of the presence of ortho-xylyl moieties; the 'low-toxicity' TCPs are largely devoid of ortho substituents and have extremely low potential to cause OPIDN. The TCP produced in the 1940s and 1950s were more than 400 times as toxic as the 'low-toxicity' TCPs produced today. Analysis of the doses required to produce OPIDN in a subchronic hen study suggests that the minimum toxic dose of 'conventional' TCP for producing OPIDN in a 70-kg person would be 280 mg/d, and for JEO containing 3% TCP, 9.4 g/d. Food products could be inadvertently contaminated with neat 'conventional' TCP but it is unlikely that food such as cooking oil would be contaminated with enough JEO + 3% TCP to cause toxicity. Further, at the dosage required for neurotoxiciy, it would be virtually impossible for a person to receive enough JEO + 3% TCP in the normal workplace (or in an aircraft) to cause such toxicity. There is no record of a JEO formulated with the modern 'conventional' TCP causing human neurotoxicity.

Retentive Solvolysis. 15. Salt Effect ion the Retentive Phenolyses of 1-(p-Substituted phenyl)ethyl p-Nitrobenzoates. The Pattern of Salt Effect and the Number of Ion-Pair Intermediates in the SN1 Solvolysis

Kinoshita, Tomomi,Shibayama, Koichi,Ikai, Keizo,Okamoto, Kunio

, p. 2917 - 2922 (1988)

The salt effect of sodium phenoxide on the polarimetric (kp) and titrimetric rate constants (kt) has exhibited pattern B for the phenolysis of optically active 1-(p-methylphenyl)ethyl p-nitrobenzoate (ROPNB; (1)) in pure phenol.The other patterns A, C, and D were previously observed for the phenolyses of 1-phenylethyl p-nitrobenzoates with p-MeO- (2), p-H- (3), and p-NO2-substituents (4), respectively.Thus, the kp-kt pattern changes in the order A -> B -> C -> D as the stability of the intermediate decreases in the order of 2 > 1 > 3 > 4.All the kp-kt patterns can be correlated with the ion-pair stage for product formation, i.e., the pattern A with the second ion-pair intermediate and the patterns B, C, and D with the first one.The pattern of salt effect on the product distribution (percent of ROPh, o- and p-RC6H4OH, and p-MeC6H4CH=CH2) for 1 is also compatible with the kp-kt pattern B.

One-pot synthesis of cresols from toluene and hydroxylamine catalyzed by ammonium molybdate

Zhang, Dongsheng,Gao, Liya,Wang, Yanji,Xue, Wei,Zhao, Xinqiang,Wang, Shufang

, p. 1109 - 1112 (2011)

One-pot synthesis of cresols from toluene and hydroxylamine catalyzed by ammonium molybdate was investigated under mild conditions. The hydroxylation reaction was strongly dependent on reaction medium, temperature, the amount of catalyst and hydroxylamine. Moreover, the reaction took place more efficiently in a closed system than in open air. High toluene conversion (72.9%) and cresol selectivity (79.4%) were obtained at 80 °C in water-acetic acid-sulfuric acid medium.

Efficient hydroxylation of aromatic compounds catalyzed by an iron(II) complex with H2O2

Wang, Xiao,Zhang, Tianyong,Li, Bin,Yang, Qiusheng,Jiang, Shuang

, p. 666 - 672 (2014)

A mononuclear iron(II) complex, Et4N[Fe(C10H 6NO2)3], coordinated by three 1-nitroso-2-naphtholate ligands in a fac-N3O3 geometry, was initiated to catalyze the direct hydroxylation of aromatic compounds to phenols in the presence of H2O2 under mild conditions. Various reaction parameters, including the catalyst dosage, temperature, mole ratio of H2O2 to benzene, reaction time and solvents which could affect the hydroxylation activity of the catalyst, were investigated systematically for benzene hydroxylation to obtain ideal benzene conversion and high phenol distribution. Under the optimum conditions, the benzene conversion was 10.2% and only phenol was detected. The catalyst was also found to be active towards hydroxylation of other aromatic compounds with high substrate conversions. The hydroxyl radical formed due to the reaction of the catalyst and H2O2 was determined to be the crucial active intermediate in the hydroxylation. A rational pathway for the formation of the hydroxyl radical was proposed and justified by the density functional theory calculations. Copyright

-

Huang

, p. 3084,3087 (1954)

-

Visible-Light Photoredox Borylation of Aryl Halides and Subsequent Aerobic Oxidative Hydroxylation

Jiang, Min,Yang, Haijun,Fu, Hua

, p. 5248 - 5251 (2016)

Efficient and practical visible-light photoredox borylation of aryl halides and subsequent aerobic oxidative hydroxylation were developed. The protocols use readily available aryl halides and bis(pinacolato)diboron as the starting materials, fac-Ir(ppy)3 as the photocatalyst, and corresponding arylboronic esters and phenols were obtained in good yields. The methods show some advantages including simple equipment, mild conditions, easy operation, and wide substrate scope. Therefore, they should provide a valuable strategy for chemical transformations.

The complex synergy of water in metal/bromide autoxidations. Part II. Effect of water and catalyst on the aerobic oxidation of benzaldehydes and the effect of water on the elementary catalytic pathways

Partenheimer, Walt

, p. 580 - 590 (2005)

All of the rates of the elementary steps in the Co/Br and Co/Mn/Br homogeneous, liquid-phase catalyzed reactions decrease with increasing water concentration in acetic acid. The step-wise replacement of the acetic acid ligands by water ligands in the coordination sphere of the catalyst metals may be responsible for this behavior. The non-catalyzed and metal-catalyzed (Co, Co/Mn/Br and Co/Mn) aerobic oxidations of benzaldehyde and 4-methylbenzaldehyde are reported. The non-catalyzed autoxidations are quite vigorous reactions in acetic acid/water mixtures but by-products from the Baeyer-Villiger reaction, the thermal decomposition of the peroxy acid, and over-oxidation to carbon dioxide limit the yield to the aromatic carboxylic acids. As the concentration of a Co or Co/Mn/Br catalyst increases these by-products are first reduced and then eliminated probably due to the very fast, selective reaction of [Co(II)]2 with the peroxy acid. A Co/Mn catalyst completely inhibits the autoxidation of the benzaldehydes. There is a gradual change in the yield of terephthaldicarboxaldehyde from 4-methylbenzaldehyde with increasing Co/Mn/Br concentration suggesting that the non-catalyzed steps are being replaced by catalyzed ones. The autoxidation of heptaldehyde generates about 500 times more carbon monoxide than does benzaldehyde using a Co/Mn/Br catalyst and gives only a 50% yield to heptanoic acid consistent with excessive amounts of decarbonylation with aliphatic aldehydes.

Effects of salt, acid and base on the decomposition of 2-chlorophenol in supercritical water

Lee, Geun-Hee,Nunoura, Teppei,Matsumura, Yukihiko,Yamamoto, Kazuo

, p. 1128 - 1129 (2001)

The effect of salt, acid and base as additives on the decomposition of 2-chlorophenol (2CP) in supercritical water was investigated. Four additives were selected, NaCl as a salt, HCl and H2SO4 as acids, and KOH as a base. The addition of salts and acids had a little effect on the decomposition of 2CP in supercritical water (SCW), but that of bases showed a significant effect to enhance the decomposition rate.

Catalytic cleavage of ether C-O bonds by pincer iridium complexes

Haibach, Michael C.,Lease, Nicholas,Goldman, Alan S.

, p. 10160 - 10163 (2014)

The development of efficient catalytic methods to cleave the relatively unreactive C-O bonds of ethers remains an important challenge in catalysis. Building on our group's recent work, we report the dehydroaryloxylation of aryl alkyl ethers using pincer iridium catalysts. This method represents a rare fully atom-economical method for ether C-O bond cleavage.

Catalytic Activation of Unstrained C(Aryl)-C(Alkyl) Bonds in 2,2′-Methylenediphenols

Dong, Guangbin,Ratchford, Benjamin L.,Xue, Yibin,Zhang, Rui,Zhu, Jun

supporting information, p. 3242 - 3249 (2022/02/23)

Catalytic activation of unstrained and nonpolar C-C bonds remains a largely unmet challenge. Here, we describe our detailed efforts in developing a rhodium-catalyzed hydrogenolysis of unstrained C(aryl)-C(alkyl) bonds in 2,2′-methylenediphenols aided by removable directing groups. Good yields of the monophenol products are obtained with tolerating a wide range of functional groups. In addition, the reaction is scalable, and the catalyst loading can be reduced to as low as 0.5 mol %. Moreover, this method proves to be effective to cleave C(aryl)-C(alkyl) linkages in both models of phenolic resins and commercial novolacs resins. Finally, detailed experimental and computational mechanistic studies show that with C-H activation being a competitive but reversible off-cycle reaction, this transformation goes through a directed C(aryl)-C(alkyl) oxidative addition pathway.

Aryl phenol compound as well as synthesis method and application thereof

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Paragraph 0046-0049, (2021/05/12)

The invention discloses a synthesis method of an aryl phenol compound shown as a formula (3). All systems are carried out in an air or nitrogen atmosphere, and visible light is utilized to excite a photosensitizer for catalyzation. In a reaction solvent, ArNR1R2 as shown in a formula (1) and water as shown in a formula (2) are used as reaction raw materials and react under the auxiliary action of acid to obtain the aryl phenol compound as shown in a formula (3). The ArNR1R2 in the formula (1) can be primary amine and tertiary amine, can also be steroid and amino acid derivatives, and can also be drugs or derivatives of propofol, paracetamol, ibuprofen, oxaprozin, indomethacin and the like. The synthesis method has the advantages of cheap and easily available raw materials, simple reaction operation, mild reaction conditions, high reaction yield and good compatibility of substrate functional groups. The fluid reaction not only can realize amplification of basic chemicals, but also can realize amplification of fine chemicals, such as synthesis of drugs propofol and paracetamol. The invention has wide application prospect and use value.

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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