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122-79-2

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122-79-2 Usage

Chemical Description

Phenyl acetate is an organic compound with the formula C6H5COOCH3.

Chemical Properties

Different sources of media describe the Chemical Properties of 122-79-2 differently. You can refer to the following data:
1. colourless liquid
2. Phenylacetate, a product of phenylalanine metabolism. It is a small molecule normally present in the mammalian circulation in low concentrations. Phenylacetate has an offensive odor.

Uses

Different sources of media describe the Uses of 122-79-2 differently. You can refer to the following data:
1. Phenyl Acetate is a metabolite of Phenylbutyrate (PB), useful in the treatment of neuroblastoma and lung cancer. An odorant found in strawberries, passion fruit and black tea.
2. Phenyl acetate levels in urine are marker for the diagnosis of some forms of unipolar major depressive disorders. It undergoes Fries rearrangement to form a mixture of o- and p-hydroxyacetophenones which are useful intermediates in manufacture of pharmaceuticals. It is a metabolite of Phenylbutyrate (PB), useful in the treatment of neuroblastoma and lung cancer. An odorant found in strawberries, passion fruit and black tea.

Definition

ChEBI: An acetate ester obtained by the formal condensation of phenol with acetic acid.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 4567, 1988 DOI: 10.1016/S0040-4039(00)80548-1Chemical and Pharmaceutical Bulletin, 30, p. 4242, 1982 DOI: 10.1248/cpb.30.4242Synthetic Communications, 19, p. 1271, 1989 DOI: 10.1080/00397918908054534

General Description

A clear colorless liquid with a sweetish solvent odor. Specific gravity 1.073. Flash point 176°F. Boiling point 383-384°F. Difficult to ignite. Used as a laboratory reagent and in the production of some organic chemicals.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

An ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Safety Profile

Moderately toxic by ingestion. Mildly toxic by skin contact. A skin irritant. Combustible when exposed to heat, flame oroxidizers. To fight fire, use alcohol foam. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Phenyl acetate acid is freed from phenol and acetic acid by washing (either directly or as a solution in pentane) with aqueous 5% Na2CO3, then with saturated aqueous CaCl2, drying with CaSO4 or Na2SO4, and fractionally distilling under reduced pressure. [Beilstein 6 II 153, 6 III 595, 6 IV 611.]

Check Digit Verification of cas no

The CAS Registry Mumber 122-79-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 2 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 122-79:
(5*1)+(4*2)+(3*2)+(2*7)+(1*9)=42
42 % 10 = 2
So 122-79-2 is a valid CAS Registry Number.
InChI:InChI=1/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3

122-79-2 Well-known Company Product Price

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  • Alfa Aesar

  • (B22561)  Phenyl acetate, 99%   

  • 122-79-2

  • 250g

  • 341.0CNY

  • Detail
  • Alfa Aesar

  • (B22561)  Phenyl acetate, 99%   

  • 122-79-2

  • 1000g

  • 1217.0CNY

  • Detail

122-79-2SDS

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 phenyl acetate

1.2 Other means of identification

Product number -
Other names PHENYL ACETATE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:122-79-2 SDS

122-79-2Synthetic route

acetic anhydride
108-24-7

acetic anhydride

phenol
108-95-2

phenol

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With pyridine; aluminum oxide at 103 - 105℃; for 2h; microwave irradiation;100%
With 2,6-di-tert-butyl-pyridine; sodium tetracarbonyl cobaltate In acetonitrile for 12h;100%
With SBA-15-Ph-Pr-SO3H at 20℃; for 0.25h;100%
Isopropenyl acetate
108-22-5

Isopropenyl acetate

phenol
108-95-2

phenol

A

acetone
67-64-1

acetone

B

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With potassium carbonate; Aliquat 336 In neat (no solvent) at 70℃; for 0.5h;A n/a
B 100%
With potassium carbonate; Aliquat 336 In neat (no solvent) at 70℃; for 0.5h; Product distribution;A n/a
B 100%
Ni(CH3)(OC6H5)(C10H8N2)
72918-80-0

Ni(CH3)(OC6H5)(C10H8N2)

A

Ni(CO)2(2,2'-bipyridine)
14917-14-7

Ni(CO)2(2,2'-bipyridine)

B

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With carbon monoxide In tetrahydrofuran (N2 or Ar), complex dissolved in THF, evacuated, excess CO introduced at room temp.C for 0.3 h; IR;A n/a
B 100%
With carbon monoxide In tetrahydrofuran (N2 or Ar), complex dissolved in THF, evacuated, equimolar amount CO introduced at -78°C for 10 h; IR;A n/a
B 31%
acetyl chloride
75-36-5

acetyl chloride

phenol
108-95-2

phenol

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In acetonitrile at 20℃; for 1h;99%
In cyclohexane at 20℃; Solvent; Temperature;99%
montmorillonite K-10 In dichloromethane for 2h; Ambient temperature;98%
acetophenone
98-86-2

acetophenone

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With oxone; silica gel In dichloromethane at 20℃; for 16h; Baeyer-Villiger oxidation;99%
With 3-chloro-benzenecarboperoxoic acid In water at 80℃; for 2h; Oxidation;89%
With 3-chloro-benzenecarboperoxoic acid In water at 80℃; for 1.5h;85%
vinyl acetate
108-05-4

vinyl acetate

phenol
108-95-2

phenol

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 70 - 140℃; for 0.183333h; Catalytic behavior; Temperature; Solvent; Reagent/catalyst; Time; Microwave irradiation;99%
With Rasta resin-(1,5,7-triazabicyclo[4.4.0]dec-5-ene)[RR-TBD] In tetrahydrofuran at 20 - 60℃;97%
With 4 A molecular sieve; tetrabutylammonium tricarbonylnitrosylferrate In hexane at 80℃; for 24h;80%
carbon monoxide
201230-82-2

carbon monoxide

methyl iodide
74-88-4

methyl iodide

phenol
108-95-2

phenol

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With iridium(III) chloride; triphenylphosphine In acetonitrile at 180℃; under 3750.38 Torr; for 20h; Autoclave;95%
1,1,1-Trifluoro-2-(acetyloxy)-2-propene
2247-91-8

1,1,1-Trifluoro-2-(acetyloxy)-2-propene

phenol
108-95-2

phenol

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 60 - 140℃; for 0.183333h; Microwave irradiation;93%
4-acetoxyphenyl tosylate
82969-01-5

4-acetoxyphenyl tosylate

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With dimethylamine borane; potassium carbonate; tricyclohexylphosphine; bis(triphenylphosphine)nickel(II) chloride In N,N-dimethyl-formamide at 20℃; for 14h;92%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

phenol
108-95-2

phenol

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With triethylamine In toluene for 12h; Inert atmosphere; Reflux;92%
acetophenone
98-86-2

acetophenone

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With hydrogenchloride In chloroform at 20℃; for 11h; Baeyer-Villiger oxidation;A 7%
B 91%
With methyltrifluoromethyldioxirane; (η5-C5H4SiMe3)2NbH(O)C=CPh2 In tetrahydrofuran at 25℃;
With (η5-C5H4SiMe3)2NbH(O)C=CPh2 at 25℃;
With α,α,α-trifluorotoluene; 3-chloro-benzenecarboperoxoic acid In chloroform for 3.5h; Ambient temperature;
DMAE phenylacetate
866569-33-7

DMAE phenylacetate

diethyl ether
60-29-7

diethyl ether

methyl iodide
74-88-4

methyl iodide

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
In acetone90%
Ni(CH3)(OC6H5)(P(C2H5)3)2
95910-33-1

Ni(CH3)(OC6H5)(P(C2H5)3)2

A

(CO)2Ni(P(C2H5)3)2
16787-33-0

(CO)2Ni(P(C2H5)3)2

B

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With carbon monoxide In diethyl ether (N2 or Ar), complex dissolved in Et2O, evacuated, excess CO introduced at room temp. for 24 h; IR;A n/a
B 90%
acetic acid
64-19-7

acetic acid

benzene
71-43-2

benzene

A

biphenyl
92-52-4

biphenyl

B

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With air; zirconium tetraacetate; cobalt(II) acetate; palladium dichloride In acetylacetone at 105℃; under 7500.6 Torr; for 6h; Product distribution; Activation energy; Further Variations:; Catalysts; Reagents; Pressures; Temperatures; solvents, ratio;A 89%
B n/a
With air; zirconium tetraacetate; cobalt(II) acetate; palladium dichloride In acetylacetone at 105℃; under 7500.6 Torr; for 6h; Product distribution; Activation energy; Kinetics; Further Variations:; Catalysts; Reagents; Pressures; Temperatures; solvents, ratio;A 89%
B n/a
2-phenoxytetrahydropyran
4203-50-3

2-phenoxytetrahydropyran

acetic anhydride
108-24-7

acetic anhydride

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
copper(II) sulfate In dichloromethane for 2.5h; Heating;89%
With 1,4-diaza-bicyclo[2.2.2]octane; bismuth (III) nitrate pentahydrate for 0.05h; Microwave irradiation;85%
With iron(III) sulfate In 1,2-dichloro-ethane for 1.5h; Heating;80%
acetic acid
64-19-7

acetic acid

methoxybenzene
100-66-3

methoxybenzene

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
Stage #1: methoxybenzene With boron tribromide In dichloromethane at 0 - 20℃; Inert atmosphere;
Stage #2: acetic acid In dichloromethane at 0 - 20℃; Inert atmosphere;
88%
acetic acid
64-19-7

acetic acid

benzyl alcohol
100-51-6

benzyl alcohol

phenol
108-95-2

phenol

A

Benzyl acetate
140-11-4

Benzyl acetate

B

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With poly(4-vinylpyridine) perchlorate In neat (no solvent) at 20℃; for 0.5h;A 88%
B 12%
trimethylphenylsilane
768-32-1

trimethylphenylsilane

acetic acid
64-19-7

acetic acid

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
With palladium diacetate; bis-[(trifluoroacetoxy)iodo]benzene at 80℃; for 17h;88%
N-acetyl saccharin
13361-42-7

N-acetyl saccharin

phenol
108-95-2

phenol

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
In neat (no solvent) at 150℃; for 1h;87%
In neat (no solvent) at 150℃; Microwave irradiation;82%
Stage #1: phenol With aluminum (III) chloride In tetrahydrofuran at 20℃; for 1h;
Stage #2: N-acetyl saccharin In tetrahydrofuran for 1h; Reflux;
11%
1-Acetyl-4(1H)-pyridinon
30074-98-7

1-Acetyl-4(1H)-pyridinon

phenol
108-95-2

phenol

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h;86%
phenyltrimethylsilyl ether
1529-17-5

phenyltrimethylsilyl ether

acetic anhydride
108-24-7

acetic anhydride

Phenyl acetate
122-79-2

Phenyl acetate

Conditions
ConditionsYield
Sulfate; titanium(IV) oxide at 20℃; for 0.5h;85%
With polyvinylpolypyrrolidone-bound boron trifluoride In acetonitrile at 20℃; for 3h;85%
With silver perchlorate; titanium tetrachloride In dichloromethane Ambient temperature;62%
Phenyl acetate
122-79-2

Phenyl acetate

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.0833333h;100%
With C17H16BrMnNO3P; potassium tert-butylate; hydrogen In 1,4-dioxane at 100℃; under 37503.8 Torr; for 16h; Autoclave;89%
Phenyl acetate
122-79-2

Phenyl acetate

phenol
108-95-2

phenol

Conditions
ConditionsYield
With HZSM-5(30) In water for 7h; Product distribution; Heating; var. catalysts; other acetylated alcohols;100%
silica gel; toluene-4-sulfonic acid In water; toluene at 80℃; for 6h;100%
With sodium hydrogen telluride; acetic acid In ethanol for 0.5h; Heating;100%
methanol
67-56-1

methanol

Phenyl acetate
122-79-2

Phenyl acetate

acetic acid methyl ester
79-20-9

acetic acid methyl ester

Conditions
ConditionsYield
With dilithium tetra(tert-butyl)zincate at 0℃; for 1h; Inert atmosphere;100%
With 2Zn(2+)*C20H14N4*4C2H3O2(1-)*1.5CH4O In neat (no solvent) at 50℃; for 18h;99%
With [Zn(bis(2-pyridylmethyl)amine)2]I2 at 50℃; for 48h;100 %Chromat.
4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

Phenyl acetate
122-79-2

Phenyl acetate

4-nitrobenzyl acetate
619-90-9

4-nitrobenzyl acetate

Conditions
ConditionsYield
With C12F18O13Zn4 at 90℃; for 18h; Inert atmosphere;99%
Phenyl acetate
122-79-2

Phenyl acetate

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

N-(4-ethylphenyl)acetamide
3663-34-1

N-(4-ethylphenyl)acetamide

Conditions
ConditionsYield
With cell-free extract containing recombinant PpATaseCH In aq. phosphate buffer; dimethyl sulfoxide at 35℃; for 24h; pH=7.5; Time;99%
Phenyl acetate
122-79-2

Phenyl acetate

formic acid ethyl ester
109-94-4

formic acid ethyl ester

3-Ethoxyacrylsaeurephenylester
105786-68-3

3-Ethoxyacrylsaeurephenylester

Conditions
ConditionsYield
With titanium tetrachloride; triethylamine In dichloromethane at -20℃; for 1h; Inert atmosphere;98%
C40H61ClLiN3O2U

C40H61ClLiN3O2U

Phenyl acetate
122-79-2

Phenyl acetate

[(1,2,3,4,5-pentamethylcyclopentadiene)U(OPh)(HN3Mes)]

[(1,2,3,4,5-pentamethylcyclopentadiene)U(OPh)(HN3Mes)]

Conditions
ConditionsYield
In toluene for 1h;98%
m-ethylaniline
587-02-0

m-ethylaniline

Phenyl acetate
122-79-2

Phenyl acetate

3-acetylamino-1-ethylbenzene
51279-01-7

3-acetylamino-1-ethylbenzene

Conditions
ConditionsYield
With cell-free extract containing recombinant PpATaseCH In aq. phosphate buffer; dimethyl sulfoxide at 35℃; for 24h; pH=7.5; Time;98%
5-decyne
1942-46-7

5-decyne

Phenyl acetate
122-79-2

Phenyl acetate

3,4-dibutyl-2H-chromen-2-one

3,4-dibutyl-2H-chromen-2-one

Conditions
ConditionsYield
With copper acetylacetonate; tris(triphenylphosphine)ruthenium(II) chloride; di-n-butyliodotin hydride; 3-ethyl-1-methyl-1H-imidazol-3-ium 2,2,2-trifluoroacetate In 1,4-dioxane; dimethyl sulfoxide at 20 - 75℃; for 6h; Reagent/catalyst; Inert atmosphere;97.4%
1,2-bis(4-fluorophenyl)acetylene
5216-31-9

1,2-bis(4-fluorophenyl)acetylene

Phenyl acetate
122-79-2

Phenyl acetate

3,4-bis(4-fluorophenyl)-2H-chromen-2-one

3,4-bis(4-fluorophenyl)-2H-chromen-2-one

Conditions
ConditionsYield
With copper acetylacetonate; tris(triphenylphosphine)ruthenium(II) chloride; di-n-butyliodotin hydride; 3-ethyl-1-methyl-1H-imidazol-3-ium 2,2,2-trifluoroacetate In 1,4-dioxane; dimethyl sulfoxide at 20 - 80℃; for 6h; Reagent/catalyst; Inert atmosphere;97.3%
4,4'-dimethoxydiphenylacetylene
2132-62-9

4,4'-dimethoxydiphenylacetylene

Phenyl acetate
122-79-2

Phenyl acetate

3,4-bis(4-methoxyphenyl)-2H-chromen-2-one

3,4-bis(4-methoxyphenyl)-2H-chromen-2-one

Conditions
ConditionsYield
With copper acetylacetonate; tris(triphenylphosphine)ruthenium(II) chloride; di-n-butyliodotin hydride; 3-ethyl-1-methyl-1H-imidazol-3-ium 2,2,2-trifluoroacetate In 1,4-dioxane; dimethyl sulfoxide at 20 - 90℃; for 5h; Reagent/catalyst; Inert atmosphere;97.2%
aniline
62-53-3

aniline

Phenyl acetate
122-79-2

Phenyl acetate

Acetanilid
103-84-4

Acetanilid

Conditions
ConditionsYield
In tetrahydrofuran-d8 at 66℃; for 48h; Catalytic behavior; Temperature; Concentration;96%
With allylchloro-[1,3-bis(diisopropylphenyl)-imidazole-2-ylidene]palladium(II); water; potassium carbonate In toluene at 110℃; for 16h; Inert atmosphere;92%
With cell-free extract containing recombinant PpATaseCH In aq. phosphate buffer; dimethyl sulfoxide at 35℃; for 24h; pH=7.5; Time;70%
Phenyl acetate
122-79-2

Phenyl acetate

A

phenyl dithioacetate
36797-15-6

phenyl dithioacetate

B

O-phenyl ethanethioate
85033-96-1

O-phenyl ethanethioate

Conditions
ConditionsYield
With Lawessons reagent In xylene for 10h; Heating;A n/a
B 96%
m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

Phenyl acetate
122-79-2

Phenyl acetate

meta-hydroxyacetanilide
621-42-1

meta-hydroxyacetanilide

Conditions
ConditionsYield
With cell-free extract containing recombinant PpATaseCH In aq. phosphate buffer; dimethyl sulfoxide at 35℃; for 24h; pH=7.5; Concentration;96%
Phenyl acetate
122-79-2

Phenyl acetate

4-bromophenyl acetate
1927-95-3

4-bromophenyl acetate

Conditions
ConditionsYield
With bromine fluoride In ethanol; chloroform at -78℃; for 0.25h;95%
With tetrachloromethane; N-Bromosuccinimide
With phosphorus pentabromide
With bromine fluoride; ethanol 1.) CFCl3, -75 deg C; 2.) CHCl3, -75 deg C, 5-15 min; Yield given. Multistep reaction;
Phenyl acetate
122-79-2

Phenyl acetate

o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

Conditions
ConditionsYield
for 0.116667h; Rearrangement; microwave irradiation;95%
With aluminum (III) chloride In neat (no solvent) at 140 - 150℃; Fries Phenol Ester Rearrangement;90%
With hydrogen fluoride supported on silica gel In neat (no solvent) at 55℃; for 4h; Temperature; Green chemistry;77%

122-79-2Related news

A metal-free protocol for direct oxidative de-alkoxycarbonylation of alkyl PHENYL ACETATE (cas 122-79-2) by molecular iodine09/08/2019

A metal-free protocol for the direct oxidative de-alkoxycarbonylation of alkyl phenyl acetate has been carried out by molecular iodine with good yield. In the present Letter, the vital role of iodine in oxidative de-alkoxycarbonylation is described. This method has been proven to be tolerant to ...detailed

122-79-2Relevant articles and documents

Acyl iodides in organic synthesis: I. Reactions with alcohols

Voronkov,Trukhina,Vlasova

, p. 1576 - 1578 (2002)

Reaction of acyl iodides RC(O)I (R = Me, Ph) with alcohols R′OH (R′ = Me, Et, i-Pr, t-Bu, CH2= CHCH2, HC≡CCH2) provides in the corresponding organyl iodides R′I. Unlike that 2-chloroethanol and phenol (R′ = CH 2CH2Cl, Ph) react with RC(O)I in the same way as with acyl chlorides yielding esters RCO2R′. This reaction path occurs partially also with methanol and ethanol.

A sulfonated Schiff base dimethyltin(iv) coordination polymer: Synthesis, characterization and application as a catalyst for ultrasound- or microwave-assisted Baeyer-Villiger oxidation under solvent-free conditions

Martins, Luísa M.D.R.S.,Hazra, Susanta,Guedes Da Silva, M. Fátima C.,Pombeiro, Armando J. L.

, p. 78225 - 78233 (2016)

The synthesis and crystal structure of the new dimethyltin(iv) compound [SnMe2(HL)(CH3OH)]n·(0.5nCH3OH) (1) derived from the Schiff base 2-[(2,3-dihydroxyphenyl)methylideneamino]benzenesulfonic acid (H3L) are described. Despite having six potentially donating centres (one imine nitrogen, two phenoxo and three sulfonate oxygen atoms), the monoprotonated dianionic ligand (HL2-) behaves as an O,O,O-tridentate chelator. Single crystal X-ray diffraction revealed that 1 is a 1D coordination polymer with every tin(iv) ion bound to two methyl groups, a methanol molecule, two Ophenoxo and one μ-Osulfonate atom from HL2-. The coordination polymer 1 was applied as a heterogeneous catalyst for the Baeyer-Villiger oxidation of ketones to esters or lactones, using aqueous hydrogen peroxide as oxidant, under ultrasound (US) or microwave (MW) irradiation and solvent- and additive-free conditions. Overall conversions up to 76/82, 98/93, 93/89, 91/94, 83/90, 68/62 and 81/87% under US/MW irradiations were obtained with 3,3-dimethyl-2-butanone, cyclopentanone, 2-methylcyclopentanone, cyclohexanone, 3-methylcyclohexanone, benzophenone and acetophenone, respectively. The catalyst can be recycled up to five cycles without losing appreciable activity.

Chemistry of anti-o,o'-dibenzene

Noh, Taehee,Gan, Hong,Halfon, Sharon,Hrnjez, Bruce J.,Yang, Nien-Chu C.

, p. 7470 - 7482 (1997)

A new and efficient preparation of anti-o,o'-dibenzene 1 has been achieved in three steps from cis-3,5-cyclohexadiene-1,2-diol 25. Utilizing a method for deoxygenation of 1,2-diols developed in our laboratory, anti-tetraol 23 was converted to 1 in 65% yield on a 0.5 g scale; This has allowed us to explore the chemistry of anti-dibenzenes extensively. The kinetics for thermal reversion of 1 to benzene have been studied in three different solvents. The direct photolysis of 1 to benzene has been found to form excited benzene in unit efficiency. This high efficiency of adiabatic photon up-conversion in the singlet manifold is unprecedented. No light was detected in the thermal dissociation of 1 in solution using various sensitizers. The chemiluminescence spectrum from the thermolysis of 1 in the presence of perylene has been recorded and found to correspond to the emission of perylene excimer. Although the efficiency of the chemiluminescent process was very low, it has proven to be one of a very few examples of chemiluminescent reactions from pure hydrocarbons. The possible mechanisms were discussed. Benzene 1,4-endoperoxide 36 was formed during the photolysis of monoperoxide 34 at low temperature. Peroxide 36 underwent a quantitative concerted retrocycloaddition to benzene and singlet oxygen. The half-life of 36 was determined to be 29 min at -30°C.

Baeyer-Villiger oxidation of ketones with a silica-supported peracid in supercritical carbon dioxide under flow conditions

Mello, Rossella,Olmos, Andrea,Parra-Carbonell, Javier,Gonzalez-Nunez, Maria Elena,Asensio, Gregorio

, p. 994 - 999 (2009)

[2-Percarboxyethyl]-functionalized silica reacts with ketones in supercritical carbon dioxide at 250 bar and 40 °C under flow conditions to yield the corresponding esters and lactones. The solid reagent can be easily recycled through treatment with 70% hydrogen peroxide in the presence of an acid at 0°C. This procedure not only simplifies the isolation of the reaction products, but has the advantage of using only water and carbon dioxide as solvents under mild conditions.

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Laurence et al.

, p. 353 (1977)

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Platinum and palladium complexes containing cationic ligands as catalysts for arene H/D exchange and oxidation

Emmert, Marion H.,Gary, J. Brannon,Villalobos, Janette M.,Sanford, Melanie S.

, p. 5884 - 5886 (2010)

Cationic catalysts in HD: Palladium(II) and platinum(II) complexes of pyridinium-substituted bipyridine ligands are highly active and stable catalysts for H/D exchange and oxidation of aromatic C-H bonds (TONs up to 3200, TOFs up to 0.1 s-1; se

Enhanced shape selective catalysis of mixed cyclic ketones in aerobic Baeyer-Villiger oxidation with magnetic Cu-Fe3O4 supported mesoporous silica microspheres

Zheng, Chunming,Chang, Shubin,Yang, Chuanwu,Lian, Dongying,Ma, Chao,Zhang, Chunrong,Fan, Xiangrui,Xu, Shichao,Sun, Xiaohong

, p. 2608 - 2616 (2018)

Various strategies have been developed to improve the conversion for the Baeyer-Villiger oxidation. However, the catalytic effects of the Baeyer-Villiger oxidation for the mixed ketones are rarely reported, though it is also important for the natural and industrial separation processes. In this report, magnetite Cu modified Fe3O4 supported mesoporous silica microspheres (Cu-Fe3O4@mSiO2) have been successfully synthesized by two step direct hydrothermal method (DHT). Over 99% of cyclohexanone conversion was obtained with mild air oxidation and benzaldehyde as sacrificing agent over Cu-Fe3O4@mSiO2. The catalytic system also shows higher conversion rates for small molecular ketones in the mixed ketone reactants, which was attributed to the enhanced mass transfer effect and Fe-Cu composite active sites in the magnetite mesoporous silica microspheres. The catalyst could be recycled for four times with similar catalytic performance, which shows enhanced shape selectivity in aerobic Baeyer-Villiger oxidations for mixed cyclic ketones.

Methyl formate as a carbonylating agent for the catalytic conversion of phenol to methyl phenyl carbonate

Yalfani, Mohammad S.,Lolli, Giulio,Wolf, Aurel,Mleczko, Leslaw,Mueller, Thomas E.,Leitner, Walter

, p. 1146 - 1149 (2013)

Methyl formate was used as a green and efficient carbonylating agent in the synthesis of methyl phenyl carbonate from phenol. Methyl formate showed better performance compared to toxic CO gas and the ability to produce other useful carbonylated products, e.g., dimethyl carbonate and dimethyl oxalate.

Reactivity of dehydrometallophthalocyanines and - Porphyrazines

Vagin, Sergei I.,Frickenschmidt, Antje,Kammerer, Bernd,Hanack, Michael

, p. 985 - 991 (2007)

The zinc dehydrophthalocyanine 2 and zinc dehydrobenzoporhyrazine 8a were generated from the 1N-aminobenzotriazole-annulated zinc phtalocyanine 1 and zinc benzoporhyrazine 8, respectively, by oxidation with Pb(OAc)4 in different solvents, for example, diethyl ether, tetrahydrofuran, acetic acid, and benzene. The reactivity of 2 and 8a was studied in detail. These species not only easily undergo Diels-Alder additions with dienes, but also the used solvents can be added. Among the addition products with solvents ethoxy-, acetoxy-, acetoxybutyloxy-substituted and barrelen-fused phthalocyanines and benzoporpyrazines were isolated. No products resulting from the dimerization of two denydro species were observed either for 2 or 8a. Analysis of the reaction products in comparison with those obtained by oxidation of 1-aminobenzotriazole 15 under similar conditions proves a higher reactivity (electrophilicity) of the dehydro-PcZn 2 and dehydro-PzZn 8a in comparison with unsubstituted benzyne towards the solvents used, such as diethyl ether and benzene.

Mechanism of the palladium-catalyzed arene C-H acetoxylation: A comparison of catalysts and ligand effects

Cook, Amanda K.,Sanford, Melanie S.

, p. 3109 - 3118 (2015)

This article describes detailed mechanistic studies focused on elucidating the impact of pyridine ligands on the Pd-catalyzed C-H acetoxylation of benzene. Three different catalysts, Pd(OAc)2, Pd(OAc)2/pyridine (1:1), and Pd(OAc)2/pyridine (1:2), are compared using a combination of mechanistic tools, including rate and order studies, Hammett analysis, detailed characterization of catalyst resting states, and isotope effects. The data from these experiments implicate C-H activation as the rate-limiting step in all cases. The major difference between the three catalysts is proposed to be the resting state of Pd. Under the reaction conditions, Pd(OAc)2 rests as an acetate bridged dimer, while the Pd(OAc)2/pyridine (1:2) catalyst rests as the monomer (pyridine)2Pd(OAc)2. In contrast, a variety of experiments suggest that the highly active catalyst generated from the 1:1 combination of Pd(OAc)2 and pyridine rests as the dimeric structure [(pyridine)Pd(OAc)2]2.

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Friess

, p. 14 (1949)

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Chemistry of diamino-ligated methylpalladium(II) alkoxides and aryloxides (Part II): Methoxide formation and carbonylation reactions

Kapteijn, Gerardus M.,Dervisi, Athanasia,Verhoef, Michel J.,Van Den Broek, M.A. Frederik H.,Grove, David M.,Van Koten, Gerard

, p. 123 - 131 (1996)

Reaction of N-ligated methylpalladium(II) alkoxide and aryloxide complexes [Pd(Me)(OR)(N ~ N)] (R = Ph, CH(CF3)2; N ~ N = tmeda (N,N,N′,N′-tetramethylethylenediamine) or bpy (2,2′-bipyridyl)) with carbon monoxide produces the corresponding methylesters in high yields. The insertion takes place either into the Pd-Me bond (aryloxide complexes) or into the Pd-OR bond (alkoxide complexes). Methylpalladium(II) methoxide complexes [Pd(Me)(OMe)(N ~ N)] (N ~ N = tmeda, bpy) have been generated in situ by aryloxide- or alkoxide-methanol exchange reactions for which the equilibrium constants have been determined. The bpy-ligated methylpalladium methoxide complex undergoes insertion of CO producing either a methylpalladium methoxycarbonyl complex [Pd(Me)(CO2Me)(bpy)] (at -60°C) or an acylpalladium methoxycarbonyl complex [Pd(COMe)(CO2Me)(bpy)] (at -25°C); both carbonylated species could be isolated and characterized at low temperature.

Study on the effect of di- and trifluoromethyl groups on the Baeyer-Villiger reaction

Kitazume, Tomoya,Kataoka, Junichi

, p. 157 - 158 (1996)

Case studies of the Baeyer-Villiger reaction applied to di-and trifluoromethylketone derivatives and the effect of the fluoromethyl groups on the Baeyer-Villiger reaction, are described.

O-arylation of carboxylic acids using (phenyl)[2-(trimethylsilyl)phenyl] iodonium triflate as a precursor of arynes

Xue, Jian,Huang, Xian

, p. 2179 - 2185 (2007)

Using (phenyl)[2-(trimethylsilyl)phenyl]iodonium triflate as a precursor of arynes, Larock's method for O-arylation of carboxylic acids and arynes was developed. A variety of acids including simple aliphatic carboxylic acids, aromatic carboxylic acids, allenoic acids, and p-toluenesulfonic acid under mild reaction conditions could generate the aryl esters. Copyright Taylor & Francis Group, LLC.

Versatile mesoporous carbonaceous materials for acid catalysis

Budarin, Vitaly L.,Clark, James H.,Luque, Rafael,Macquarrie, Duncan J.

, p. 634 - 636 (2007)

Starbon mesoporous materials were synthesized after pyrolysis of expanded starch and subsequently functionalised with sulfonated groups, providing highly active and reusable materials in various acid catalysed reactions. The Royal Society of Chemistry.

Efficient Baeyer–Villiger Oxidation Catalysed by Silver Nanoparticles Stabilized on Modified Montmorillonite

Borah, Subrat Jyoti,Das, Diganta Kumar

, p. 3669 - 3677 (2018)

Abstract: Silver nanoparticles supported on modified montmorillonite clay (Ag-NPs@mont), were utilized as catalyst for the Baeyer–Villiger oxidation of various ketones with hydrogen peroxide as an oxidant under solvent free condition at room temperature. The modification of Montmorillonite K10 clay was carried out with HCl under controlled conditions for generating a high surface area porous matrix which acts as support for the in situ generation of Silver nanoparticles. The synthesized nanocomposite material was characterized by UV–Visible spectroscopy, powder XRD, SEM-EDX, TEM and N2 adsorption–desorption analysis. The catalyst can be recycled and reused several times without significant loss of their catalytic activity. Graphical Abstract: [Figure not available: see fulltext.].

Reaction of carboxylic acid esters with phenolates in oil-in-water microemulsions based on cetyltrimethylammonium bromide

Mirgorodskaya,Valeeva,Kudryavtseva,Vylegzhanina,Zuev

, p. 590 - 595 (2006)

A kinetic study of reactions of carboxylic acid esters with phenols activated with alkalis or amines in microemulsions based on cationic surfactants showed that the phenolates formed upon activation exhibit different nucleophilicity depending on the value of the negative charge on the oxygen atom, which is determined by the properties of the phenol, ionizing agent, and solvent. Pleiades Publishing, Inc., 2006.

Vinyl Phosphonic Acid Functionalized Silica Polymer Nanocomposites for the Acylation of Phenol

Amit, Dubey,Verma, Savita

, p. 724 - 733 (2022/01/13)

Abstract: In order to overcome the corrosive problems of homogeneous vinyl phosphonic acid (VPA), ordered mesoporous silica (SBA-15) is functionalized with VPA via in situ radical polymerization method to achieve SBA/VPA nanocomposites with different amou

Preparation method of O-methoxyacetophenone

-

Paragraph 0027-0028, (2021/02/10)

The invention relates to a preparation method of o-methoxyacetophenone. A composite catalyst containing heteropolyacid and Lewis acid is adopted and can effectively catalyze the reaction of dimethyl ether and o-hydroxyacetophenone so that the use of dimethyl sulfate and other highly toxic substances as reaction reagents is avoided, the production cost is lowered, the discharge of highly toxic substances is reduced, and the process is enabled to be greener and more environment-friendly.

Development of pH-activatable fluorescent probes for rapid visualization of metastatic tumours and fluorescence-guided surgeryviatopical spraying

Cao, Wenwen,Li, Xiaoxin,Wu, Peng,Xiong, Hu

supporting information, p. 10636 - 10639 (2021/10/19)

A series of pH-activatable aza-BODIPY-based fluorescent probes were developed for rapid cancer visualization and real-time fluorescence-guided surgery by harnessing topical spraying. These probes exhibited good water-solubility, a tunable pKafrom 5.0 to 7.9, and stable intense NIR emission at ~725 nm under acidic conditions.AzaB5with a pKavalue of 6.7 was able to rapidly and clearly visualize pulmonary and abdominal metastatic tumours including tiny metastases less than 2 mmviatopical spraying, further improving intraoperative fluorescence-guided resection. We believe thatAzaB5is promising as a powerful tool to rapidly delineate a broad range of malignancies and assist surgical tumour resection.

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