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139-02-6

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139-02-6 Usage

Preparation

Sodium phenoxide was freshly prepared by adding sodium metal to phenol (0.45 ?g, 4.8 mmol) dissolved in diethyl ether (15 cm3), under an atmosphere of dry nitrogen. ?This was refluxed with (11) (1.0 g, 2.8 mmol) for 23 h. Following evaporation of the ?ether, water (20 cm3) was added and the mixture extracted into DCM. The DCM solution ?was dried (MgS04) and evaporated to give a solid (1.2 g). Fractional sublimation and ?recrystallisation from acetonitrile gave recovery of 2,4,6-tribromo-3,5-difluoropyridine ?(0.8 g, 80%) and 3-phenoxy-5-fluoro-2,4,6-tribromopyridine (0.2 g, 20%), m.p. 100±1 ?OC (Found: C, 31.3; H, 1.1; N, 2.9. C11H5Br3FNO requires C, 31.0; H, 1.2; N, ?3.3%); IR spectrum no. 15; mass spectrum no. 15; nmr spectrum no. 19.

Chemical Properties

Different sources of media describe the Chemical Properties of 139-02-6 differently. You can refer to the following data:
1. White, deliquescent crystals. Soluble in water and alcohol; decomposed by carbon dioxide in the air.
2. Sodium phenate, sodium phenoxide, sodium phenolate, NaOC6H5, white solid, soluble, formed by reaction of sodium hydroxide (not carbonate) solution and phenol, and then evaporating. Used in the preparation of sodium salicylate.

Uses

Different sources of media describe the Uses of 139-02-6 differently. You can refer to the following data:
1. Sodium phenoxide is used as a precursor to aryl ethers and involved in the preparation of phenyl ethers and metal phenolates. It serves as an antiseptic and used in organic synthesis.
2. As a general disinfectant, either in solution or mixed with slaked lime, etc., for toilets, stables, cesspools, floors, drains, etc.; for the manufacture of colorless or light-colored artificial resins, many medical and industrial organic Compounds and dyes; as a reagent in chemical analysis. Pharmaceutic aid (preservative).

General Description

A white to reddish colored solid in the form of crystalline rods. Used as an antiseptic and in organic synthesis.

Air & Water Reactions

Decomposes in air. Soluble in water. In both cases, a corrosive alkaline solution forms that is a strong irritant to skin and eyes.

Reactivity Profile

Salts, basic, such as SODIUM PHENOLATE, are generally soluble in water. The resulting solutions contain moderate concentrations of hydroxide ions and have pH's greater than 7.0. They react as bases to neutralize acids. These neutralizations generate heat, but less or far less than is generated by neutralization of the bases in reactivity group 10 (Bases) and the neutralization of amines. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible.

Hazard

Strong irritant to skin and tissue.

Safety Profile

Poison by subcutaneous route. A corrosive irritant to skin, eyes, and mucous membranes. When heated to decomposition it emits toxic fumes of Na2O. See also PHENOL and SODIUM HYDROXIDE.

Purification Methods

The ground powder is washed with Et2O, then heated at 60o/1mm for 12 to 24hours to remove any free phenol and solvent. [Kornblum & Lurie J Am Chem Soc 81 2710 1959, Beilstein 6 I 718.]

Check Digit Verification of cas no

The CAS Registry Mumber 139-02-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 9 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 139-02:
(5*1)+(4*3)+(3*9)+(2*0)+(1*2)=46
46 % 10 = 6
So 139-02-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H6O.Na/c7-6-4-2-1-3-5-6;/h1-5,7H;/q;+1/p-1

139-02-6 Well-known Company Product Price

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  • Alfa Aesar

  • (B25002)  Sodium phenoxide, 98%   

  • 139-02-6

  • 50g

  • 513.0CNY

  • Detail
  • Alfa Aesar

  • (B25002)  Sodium phenoxide, 98%   

  • 139-02-6

  • 250g

  • 2244.0CNY

  • Detail
  • Alfa Aesar

  • (B25002)  Sodium phenoxide, 98%   

  • 139-02-6

  • 1000g

  • 6939.0CNY

  • Detail

139-02-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name sodium phenolate

1.2 Other means of identification

Product number -
Other names Sodium phenolate

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:139-02-6 SDS

139-02-6Synthetic route

bis(phenyl) carbonate
102-09-0

bis(phenyl) carbonate

A

sodium phenoxide
139-02-6

sodium phenoxide

B

sodium salicylat
81256-74-8

sodium salicylat

Conditions
ConditionsYield
With water; sodium hydroxide In dimethyl sulfoxide at 25℃; Kinetics;A 100%
B n/a
phenol
108-95-2

phenol

sodium phenoxide
139-02-6

sodium phenoxide

Conditions
ConditionsYield
With sodium hydroxide In methanol; water98.9%
With sodium In 1,4-dioxane for 4h; Heating;92%
With methanol; sodium
sodium 4-methylphenoxide
1121-70-6

sodium 4-methylphenoxide

poly(styrene p-tolyliodonium) hydrogensulfate

poly(styrene p-tolyliodonium) hydrogensulfate

sodium phenoxide
139-02-6

sodium phenoxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 24h;65%
2-Phenoxyethanol
122-99-6

2-Phenoxyethanol

A

sodium phenoxide
139-02-6

sodium phenoxide

B

2-phenoxyacetic acid sodium salt
3598-16-1

2-phenoxyacetic acid sodium salt

Conditions
ConditionsYield
With oxygen; bismuth(III) nitrate; palladium on activated charcoal In sodium hydroxide at 90℃; for 6h; Product distribution; also with coactivator and other activators, various times, reaction with other 2-phenoxyethanols;A n/a
B 53%
methanol
67-56-1

methanol

dimethyl phenyl phosphate
10113-28-7

dimethyl phenyl phosphate

sodium methylate
124-41-4

sodium methylate

A

trimethyl phosphite
512-56-1

trimethyl phosphite

B

sodium phenoxide
139-02-6

sodium phenoxide

Conditions
ConditionsYield
at 0℃; Rate constant;
at 19℃; Rate constant;
at 10℃; Rate constant;
diethyl ether
60-29-7

diethyl ether

ethanol
64-17-5

ethanol

trichloro-methanesulfenic acid phenyl ester
13400-05-0

trichloro-methanesulfenic acid phenyl ester

sodium ethanolate
141-52-6

sodium ethanolate

A

trichloro-methanesulfenic acid ethyl ester
13029-05-5

trichloro-methanesulfenic acid ethyl ester

B

sodium phenoxide
139-02-6

sodium phenoxide

ethanol
64-17-5

ethanol

diphenyldiphenoxysilane
1247-19-4

diphenyldiphenoxysilane

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

A

1,1,3,3,5,5-hexaphenylcyclotrisiloxane
512-63-0

1,1,3,3,5,5-hexaphenylcyclotrisiloxane

B

sodium phenoxide
139-02-6

sodium phenoxide

1,3,5-trinitro-2,4,6-triphenoxy-benzene
339199-98-3

1,3,5-trinitro-2,4,6-triphenoxy-benzene

sodium ethanolate
141-52-6

sodium ethanolate

A

1,3,5-triethoxy-2,4,6-trinitrobenzene
68959-41-1

1,3,5-triethoxy-2,4,6-trinitrobenzene

B

sodium phenoxide
139-02-6

sodium phenoxide

hexane
110-54-3

hexane

ethyl sodium
676-54-0

ethyl sodium

methoxybenzene
100-66-3

methoxybenzene

sodium phenoxide
139-02-6

sodium phenoxide

diphenyldiphenoxysilane
1247-19-4

diphenyldiphenoxysilane

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

acetone
67-64-1

acetone

A

1,1,3,3,5,5-hexaphenylcyclotrisiloxane
512-63-0

1,1,3,3,5,5-hexaphenylcyclotrisiloxane

B

sodium phenoxide
139-02-6

sodium phenoxide

hexane
110-54-3

hexane

ethyl sodium
676-54-0

ethyl sodium

Phenetole
103-73-1

Phenetole

sodium phenoxide
139-02-6

sodium phenoxide

1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

benzenesulfonic acid
98-11-3

benzenesulfonic acid

sodium phenoxide
139-02-6

sodium phenoxide

Conditions
ConditionsYield
at 310 - 360℃; Rate constant;
N,N'-bis(diphenyloxyphosphonyl)-8-quinolinesulfinamidine
70310-90-6

N,N'-bis(diphenyloxyphosphonyl)-8-quinolinesulfinamidine

A

sodium phenoxide
139-02-6

sodium phenoxide

B

sodium naphthalene-1-sulfinate
64326-13-2

sodium naphthalene-1-sulfinate

Conditions
ConditionsYield
With sodium hydroxide for 3h; Product distribution; Heating;
benzoic acid phenyl ester
93-99-2

benzoic acid phenyl ester

A

sodium benzoate
532-32-1

sodium benzoate

B

sodium phenoxide
139-02-6

sodium phenoxide

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 15℃; Rate constant; Thermodynamic data; Kinetics; var. temperatures, var. ratio of solvents, log A, Ea;
phenoxy radical
2122-46-5, 55748-05-5

phenoxy radical

sodium phenoxide
139-02-6

sodium phenoxide

Conditions
ConditionsYield
With Sodium borate; sodium azide; oxygen; sodium formate In water Rate constant; Irradiation; combination with superoxid anion radicals;
phenyl N-methyl-N-m-nitrophenylcarbamate
20376-70-9

phenyl N-methyl-N-m-nitrophenylcarbamate

A

N-methyl-3-nitroaniline
619-26-1

N-methyl-3-nitroaniline

B

sodium phenoxide
139-02-6

sodium phenoxide

Conditions
ConditionsYield
With sodium hydroxide; cetyltrimethylammonim bromide In methanol; water at 68.5℃; Rate constant; Mechanism; other N-methyl-N-arylcarbamates; reaction in absence of cetyltrimethylammonium bromide;
Methyl-(4-nitro-phenyl)-carbamic acid phenyl ester
50882-34-3

Methyl-(4-nitro-phenyl)-carbamic acid phenyl ester

A

sodium phenoxide
139-02-6

sodium phenoxide

B

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With sodium hydroxide; cetyltrimethylammonim bromide In methanol; water at 68.5℃; Rate constant;
phenolate
3229-70-7

phenolate

sodium phenoxide
139-02-6

sodium phenoxide

Conditions
ConditionsYield
With sodium cation In water; dimethyl sulfoxide at 25℃; Equilibrium constant;
sodium m-chlorophenoxide
3046-27-3

sodium m-chlorophenoxide

sodium phenoxide
139-02-6

sodium phenoxide

Conditions
ConditionsYield
With sodium tetrahydroborate; hydrogen; PdCl2 complex on modified silca gel In methanol at 20℃; under 760 Torr; Rate constant; hydrogenolysis of chlorobenzenes in the presence of palladium chloride complex deposited on modified silica gel; effect of the nature of substituents in aromatic ring;
1-phenylcarbamoyl-1-methylhydrazine
30616-32-1

1-phenylcarbamoyl-1-methylhydrazine

A

sodium phenoxide
139-02-6

sodium phenoxide

B

C2H5N2O2(1-)*Na(1+)

C2H5N2O2(1-)*Na(1+)

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 25℃; Rate constant; Mechanism; Thermodynamic data; enegy parameters calculated from kobs in range 25-60 deg C; pH range 12.7, 13.9;
N',N'-Dimethyl-hydrazinecarboxylic acid phenyl ester
18197-54-1

N',N'-Dimethyl-hydrazinecarboxylic acid phenyl ester

A

sodium phenoxide
139-02-6

sodium phenoxide

B

C3H7N2O2(1-)*Na(1+)

C3H7N2O2(1-)*Na(1+)

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 25℃; Rate constant; Mechanism; Thermodynamic data; energy parameters calculated from kobs in range 25-60 deg C; pH range 12.0, 14.9;
N,N'-Dimethyl-hydrazinecarboxylic acid phenyl ester

N,N'-Dimethyl-hydrazinecarboxylic acid phenyl ester

A

sodium phenoxide
139-02-6

sodium phenoxide

B

C3H7N2O2(1-)*Na(1+)

C3H7N2O2(1-)*Na(1+)

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 25℃; Rate constant; Mechanism; Thermodynamic data; energy parameters calculated from kobs in range 25-60 deg C; pH range 13.0, 13.9;
N,N',N'-Trimethyl-hydrazinecarboxylic acid phenyl ester

N,N',N'-Trimethyl-hydrazinecarboxylic acid phenyl ester

A

sodium phenoxide
139-02-6

sodium phenoxide

B

C4H9N2O2(1-)*Na(1+)

C4H9N2O2(1-)*Na(1+)

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 25℃; Rate constant; Mechanism; Thermodynamic data; energy parameters calculated from kobs in range 25-60 deg C; pH range 13.6, 14.1;
phenyl hydrazinecarboxylate
20605-43-0

phenyl hydrazinecarboxylate

A

sodium phenoxide
139-02-6

sodium phenoxide

B

CH3N2O2(1-)*Na(1+)

CH3N2O2(1-)*Na(1+)

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 25℃; Rate constant; Thermodynamic data; Mechanism; energy parameters calculated from kobs in range 25-60 deg C; pH range 11.9, 14.9;
methoxybenzene
100-66-3

methoxybenzene

aqueous NaOH

aqueous NaOH

sodium phenoxide
139-02-6

sodium phenoxide

Conditions
ConditionsYield
at 250 - 260℃;
pyridine
110-86-1

pyridine

methoxybenzene
100-66-3

methoxybenzene

sodium

sodium

sodium phenoxide
139-02-6

sodium phenoxide

diethyl ether
60-29-7

diethyl ether

ammonia
7664-41-7

ammonia

methoxybenzene
100-66-3

methoxybenzene

sodium

sodium

sodium phenoxide
139-02-6

sodium phenoxide

diethyl ether
60-29-7

diethyl ether

sodium amide

sodium amide

Phenyl acetate
122-79-2

Phenyl acetate

A

acetamide
60-35-5

acetamide

B

sodium phenoxide
139-02-6

sodium phenoxide

sodium amide

sodium amide

Phenyl acetate
122-79-2

Phenyl acetate

benzene
71-43-2

benzene

A

acetamide
60-35-5

acetamide

B

sodium phenoxide
139-02-6

sodium phenoxide

n-heptane
142-82-5

n-heptane

n-pentylsodium
1822-71-5

n-pentylsodium

Phenetole
103-73-1

Phenetole

A

sodium phenoxide
139-02-6

sodium phenoxide

B

2-ethoxy-phenyl sodium

2-ethoxy-phenyl sodium

Conditions
ConditionsYield
at 35℃; Product distribution;
at 75℃; Product distribution;
1-bromo-octane
111-83-1

1-bromo-octane

sodium phenoxide
139-02-6

sodium phenoxide

octyloxybenzene
1818-07-1

octyloxybenzene

Conditions
ConditionsYield
poly<1-hydroxyethylene-co-1-(2-ethylsulf In 1,4-dioxane at 75℃; for 23h; Product distribution; Rate constant; other catalysts;100%
Sucrose-ethyleneoxide adducts In toluene at 110℃; for 8h; Product distribution; further catalysts: PEG, DB18K6; further objects of study: phase-transfer catalysis;100%
dodecyldimethylsulfonium methyl sulfate In water at 40℃; for 6h;25%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

sodium phenoxide
139-02-6

sodium phenoxide

4-phenoxybenzonitrile
3096-81-9

4-phenoxybenzonitrile

Conditions
ConditionsYield
With potassium phosphate In tetrahydrofuran at 115℃; for 18h;100%
With CF3-DPPF; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; toluene at 120℃; for 20h;79.6%
With CF3-DPPF ligand; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; toluene at 120℃; for 30h; Product distribution; various DPPF ligands for the Pd-catalyzed formation of diaryl ethers;
sodium phenoxide
139-02-6

sodium phenoxide

6,7-dimethoxy-4-chloroquinazoline
13790-39-1

6,7-dimethoxy-4-chloroquinazoline

6,7-dimethoxy-4-phenoxyquinazoline
1180653-47-7

6,7-dimethoxy-4-phenoxyquinazoline

Conditions
ConditionsYield
In dimethyl sulfoxide at 80℃; for 3h;100%
4-phenyl-butan-1-ol
3360-41-6

4-phenyl-butan-1-ol

sodium phenoxide
139-02-6

sodium phenoxide

(4-phenoxybutyl)benzene
358349-92-5

(4-phenoxybutyl)benzene

Conditions
ConditionsYield
Stage #1: 4-phenyl-butan-1-ol With 1,2-Diiodoethane; N,N-dimethyl-formamide; triphenylphosphine at 20℃; for 0.0166667h; Sealed tube; Inert atmosphere;
Stage #2: sodium phenoxide at 20℃; Sealed tube; Inert atmosphere;
100%
4-Nitrophthalonitrile
31643-49-9

4-Nitrophthalonitrile

sodium phenoxide
139-02-6

sodium phenoxide

4-phenoxyphthalonitrile
38791-62-7

4-phenoxyphthalonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 1h;99%
perfluoro(propyl vinyl ether)
1623-05-8

perfluoro(propyl vinyl ether)

sodium phenoxide
139-02-6

sodium phenoxide

(2-Chloro-1,1,2-trifluoro-2-heptafluoropropyloxy-ethoxy)-benzene
144373-62-6

(2-Chloro-1,1,2-trifluoro-2-heptafluoropropyloxy-ethoxy)-benzene

Conditions
ConditionsYield
With hexachloroethane In N,N-dimethyl-formamide 1) 25 deg C - 29 deg C, 2) r.t., overnight;99%
4-nitro-N-methyl-phthalimide
41663-84-7

4-nitro-N-methyl-phthalimide

sodium phenoxide
139-02-6

sodium phenoxide

4-phenoxy-N-methyl phthalimide
63197-24-0

4-phenoxy-N-methyl phthalimide

Conditions
ConditionsYield
N-neopentyl chloride of 4-dibutylaminopyridine In toluene at 110℃; for 1h;99%
In dimethyl sulfoxide at 15 - 120℃; for 24h; Inert atmosphere;93%
dimethyl-3-sulfopropyl(ferrocenylmethyl)ammonium

dimethyl-3-sulfopropyl(ferrocenylmethyl)ammonium

sodium phenoxide
139-02-6

sodium phenoxide

hydroxymethylferrocene ethyl ether

hydroxymethylferrocene ethyl ether

Conditions
ConditionsYield
In water a mixt. of Fe compd. and C6H5ONa in water is refluxed for 5 min; mixt. is cooled and extd. with ether, extract is washed with ether and dried with sodium sulfate, removal of ether by distillation, recrystn. from heptane;99%
sodium phenoxide
139-02-6

sodium phenoxide

diphenylcarbamic chloride
83-01-2

diphenylcarbamic chloride

diphenyl-carbamic acid phenyl ester
5416-45-5

diphenyl-carbamic acid phenyl ester

Conditions
ConditionsYield
at 20℃; for 0.08h; Neat (no solvent); Microwave irradiation; Grinding;99%
tert-butyl (3-bromo-5-chloropyrazolo[1,5-a]pyrimidin-7-yl)(2-morpholinoethyl)carbamate
1610679-61-2

tert-butyl (3-bromo-5-chloropyrazolo[1,5-a]pyrimidin-7-yl)(2-morpholinoethyl)carbamate

sodium phenoxide
139-02-6

sodium phenoxide

tert-butyl (3-bromo-5-phenoxypyrazolo[1,5-a]pyrimidin-7-yl)(2-morpholinoethyl)carbamate
1610680-02-8

tert-butyl (3-bromo-5-phenoxypyrazolo[1,5-a]pyrimidin-7-yl)(2-morpholinoethyl)carbamate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 0.5h;99%
2-Amino-6-chlor-3,4,5-pyridintricarbonitril
79696-96-1

2-Amino-6-chlor-3,4,5-pyridintricarbonitril

sodium phenoxide
139-02-6

sodium phenoxide

2-Amino-6-phenoxy-3,4,5-tricyanopyridin

2-Amino-6-phenoxy-3,4,5-tricyanopyridin

Conditions
ConditionsYield
In acetone for 0.5h; Heating;98%
sodium phenoxide
139-02-6

sodium phenoxide

4-chloro-3-methylbut-2-enal dimethylacetal

4-chloro-3-methylbut-2-enal dimethylacetal

1,1-dimethoxy-3-methyl-4-phenoxybut-2-ene

1,1-dimethoxy-3-methyl-4-phenoxybut-2-ene

Conditions
ConditionsYield
In tetrahydrofuran; water for 48h; Ambient temperature;98%
sodium phenoxide
139-02-6

sodium phenoxide

C30H29Cl4N5O2P4S3
318956-66-0

C30H29Cl4N5O2P4S3

C54H49N5O6P4S3

C54H49N5O6P4S3

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;98%
C46H55NO5S

C46H55NO5S

sodium phenoxide
139-02-6

sodium phenoxide

C45H53NO3

C45H53NO3

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃;98%
sodium phenoxide
139-02-6

sodium phenoxide

tetrachlorophenoxyphosphorane
19579-04-5

tetrachlorophenoxyphosphorane

Conditions
ConditionsYield
With phosphorus pentachloride In tetrachloromethane at -15℃; for 1h;98%
biphenyl-4-yl methanol
3597-91-9

biphenyl-4-yl methanol

sodium phenoxide
139-02-6

sodium phenoxide

1-phenyl-4-phenoxymethylbenzene
29263-69-2

1-phenyl-4-phenoxymethylbenzene

Conditions
ConditionsYield
Stage #1: biphenyl-4-yl methanol With 1,2-Diiodoethane; N,N-dimethyl-formamide; triphenylphosphine at 20℃; for 0.0166667h; Sealed tube; Inert atmosphere;
Stage #2: sodium phenoxide at 20℃; Sealed tube; Inert atmosphere;
98%
potassium phenolate
100-67-4

potassium phenolate

sodium phenoxide
139-02-6

sodium phenoxide

2,2,4,4,6,6-hexaphenoxycyclotriphosphazene
1184-10-7

2,2,4,4,6,6-hexaphenoxycyclotriphosphazene

Conditions
ConditionsYield
With cesium hydroxide; 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In 1,2-dichloro-benzene at 175℃; Product distribution / selectivity;97.9%
sodium phenoxide
139-02-6

sodium phenoxide

chloroacetic acid
79-11-8

chloroacetic acid

phenol
108-95-2

phenol

2-phenoxyacetic acid
122-59-8

2-phenoxyacetic acid

Conditions
ConditionsYield
at 105℃; pH=9 - 10;97.6%
sodium phenoxide
139-02-6

sodium phenoxide

methyl chloroacetate
96-34-4

methyl chloroacetate

methyl 2-phenoxyacetate
2065-23-8

methyl 2-phenoxyacetate

Conditions
ConditionsYield
at 120℃; for 6h; Temperature;97.5%
18-crown-6 ether
17455-13-9

18-crown-6 ether

sodium phenoxide
139-02-6

sodium phenoxide

C12H24O6*3C6H5O(1-)*3Na(1+)

C12H24O6*3C6H5O(1-)*3Na(1+)

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether for 1h; Ambient temperature;97%
sodium phenoxide
139-02-6

sodium phenoxide

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

4-nitrophenyl phenyl ether
620-88-2

4-nitrophenyl phenyl ether

Conditions
ConditionsYield
N-2-ethylhexyl chloride of 4(4-methylpiperidinyl)pyridine In toluene at 110℃; for 0.25h;97%
With ammonia at 25℃; Kinetics; Concentration;
(7-methoxy[2.2]paracyclophan-4-yl)(4'-methoxyphenyl)iodonium hexafluorophosphate

(7-methoxy[2.2]paracyclophan-4-yl)(4'-methoxyphenyl)iodonium hexafluorophosphate

sodium phenoxide
139-02-6

sodium phenoxide

A

1-methoxy-4-phenoxy-benzene
1655-69-2

1-methoxy-4-phenoxy-benzene

B

4-methoxy-7-iodo[2.2]paracyclophane
1235887-94-1

4-methoxy-7-iodo[2.2]paracyclophane

Conditions
ConditionsYield
In [D3]acetonitrile at 80℃; for 1h; Inert atmosphere; Darkness; regioselective reaction;A 75%
B 97%
(S)-(1-benzyl-2,5-dihydro-1H-pyrrol-2-yl)methanol
1313436-04-2

(S)-(1-benzyl-2,5-dihydro-1H-pyrrol-2-yl)methanol

sodium phenoxide
139-02-6

sodium phenoxide

(R)-1-benzyl-3-phenoxy-1,2,3,6-tetrahydropyridine
1313435-87-8

(R)-1-benzyl-3-phenoxy-1,2,3,6-tetrahydropyridine

Conditions
ConditionsYield
Stage #1: (S)-(1-benzyl-2,5-dihydro-1H-pyrrol-2-yl)methanol With trifluoromethylsulfonic anhydride In dichloromethane at -15℃; Inert atmosphere;
Stage #2: sodium phenoxide In tetrahydrofuran; dichloromethane at -15 - 20℃; Inert atmosphere; optical yield given as %ee; regioselective reaction;
97%
C29H36ClIrP2S2

C29H36ClIrP2S2

sodium phenoxide
139-02-6

sodium phenoxide

C35H41IrOP2S2

C35H41IrOP2S2

Conditions
ConditionsYield
In dichloromethane at 20℃; for 36h; Inert atmosphere; Glovebox;97%
4-(bromomethyl)-1,3-bis(2,6-diisopropylphenyl)-1,2,3-triazolium hexafluorophosphate

4-(bromomethyl)-1,3-bis(2,6-diisopropylphenyl)-1,2,3-triazolium hexafluorophosphate

sodium phenoxide
139-02-6

sodium phenoxide

1,3-bis(2,6-diisopropylphenyl)-4-(phenoxymethyl)-1,2,3-triazolium hexafluorophosphate

1,3-bis(2,6-diisopropylphenyl)-4-(phenoxymethyl)-1,2,3-triazolium hexafluorophosphate

Conditions
ConditionsYield
In water; acetone at 20℃; for 12h; Schlenk technique;97%
4,5-dichloro-1-phenylpyridazin-6-one
1698-53-9

4,5-dichloro-1-phenylpyridazin-6-one

sodium phenoxide
139-02-6

sodium phenoxide

5-chloro-4-phenoxy-2-phenyl-2H-pyridazin-3-one
38387-54-1

5-chloro-4-phenoxy-2-phenyl-2H-pyridazin-3-one

Conditions
ConditionsYield
In 1,4-dioxane for 16h; Ambient temperature;96%
(2-13C)bromoacetic acid
64891-77-6

(2-13C)bromoacetic acid

sodium phenoxide
139-02-6

sodium phenoxide

<2-13C>-2-phenoxyacetic acid
134757-64-5

<2-13C>-2-phenoxyacetic acid

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 2h; Heating;96%
bis(4-methylbenzenethiocarbonyl) sulphide
60410-77-7

bis(4-methylbenzenethiocarbonyl) sulphide

sodium phenoxide
139-02-6

sodium phenoxide

O-phenyl 4-methylbenzenecarbothioate
52322-79-9

O-phenyl 4-methylbenzenecarbothioate

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether; ethanol for 3h; Ambient temperature;96%

139-02-6Relevant articles and documents

Mononuclear Sulfido-Tungsten(V) Complexes: Completing the Tp*MEXY (M = Mo, W; E = O, S) Series

Sproules, Stephen,Eagle, Aston A.,George, Graham N.,White, Jonathan M.,Young, Charles G.

, p. 5189 - 5202 (2017)

Orange Tp*WSCl2 has been synthesized from the reactions of Tp*WOCl2 with boron sulfide in refluxing toluene or Tp*WS2Cl with PPh3 in dichloromethane at room temperature. Mononuclear sulfido-tungsten(V) complexes, Tp*WSXY {X = Y = Cl, OPh, SPh, SePh; X = Cl, Y = OPh; XY = toluene-3,4-dithiolate (tdt), quinoxaline-2,3-dithiolate (qdt); and Tp* = hydrotris(3,5-dimethylpyrazol-1-yl)borate} were prepared by metathesis of Tp*WSCl2 with the respective alkali metal salt of X-/XY2-, or [NHEt3]2(qdt). The complexes were characterized by microanalysis, mass spectrometry, electrochemistry, and infrared (IR), electron paramagnetic resonance (EPR) and electronic absorption spectroscopies. The molecular structures of Tp*WS(OPh)2, Tp*WS(SePh)2, and Tp*WS(tdt) have been determined by X-ray crystallography. The six-coordinate, distorted-octahedral W centers are coordinated by terminal sulfido (WS = 2.128(2) - 2.161(1) ?), terdentate facial Tp*, and monodentate/bidentate O/S/Se-donor ligands. The sulfido-W(V) complexes are characterized by lower energy electronic transitions, smaller giso, and larger Aiso(183W) values, and more positive reduction potentials compared with their oxo-W(V) counterparts. This series has been probed by sulfur K-edge X-ray absorption spectroscopy (XAS), the spectra being assigned by comparison to Tp*WOXY (X = Y = SPh; XY = tdt, qdt) and time-dependent density functional theoretical (TD-DFT) calculations. This study provides insight into the electronic nature and chemistry of the catalytically and biologically important sulfido-W unit.

Structure and reactivity of sodium phenoxide - Following the course of the Kolbe-Schmitt reaction

Kunert, Michael,Dinjus, Eckhard,Nauck, Maria,Sieler, Joachim

, p. 1461 - 1465 (1997)

Solvent-free sodium phenoxide (NaOPh) crystallises as a polymer and forms a polymeric chain in the [001] direction. The low coordination of the sodium atoms, as evident in the crystal structure, is confirmed by the easy coordination of oxoligands (σ-donors). Hence, the four-membered ring chain of the solvent-free sodium phenoxide is separated by oxoligands, and forms partial structures as the polymer fragments. Thus, NaOPh crystallises in THF with the formation of an Na6O6 core, consisting of two face-fused heterocubes, and in N,N,N′,N′-tetrarnethyl urea (TMU) with the formation of a Na4O4 heterocubane. The solvent-free NaOPh-CO2 complex obtained from the addition of CO2 to a solution of sodium phenoxide is, when exposed to a temperature of 80 °C, subject to an irreversible phase transition, as demonstrated by FT-IR and DTA studies. The complex formed at 80 °C is, apparently, another intermediate of the Kolbe-Schmitt reaction. WILEY-VCH Verlag GmbH,.

Electrochemical reductive dehalogenation of ortho-halogenated phenols on Ag electrode by in situ FTIR

Yi, Jingmiao,Lu, Jinjin,Shi, Xiaohong,Song, Dandan,Zhao, Weijuan,Li, Meichao

, p. 3879 - 3882 (2014)

Electrochemical reductive dehalogenation reactions of ortho-halogenated phenols, namely, o-iodophenol (OIP), o-bromphenol (OBP) and o-chlorophenol (OCP) on Ag electrode in alkaline medium have been studied by in situ FTIR combined with cyclic voltammetry and computational calculations. The Ag electrode showed a high electrochemical activity for dehalogenation reactions of OBP and OIP in contrast with OCP under the similar conditions and the dehalogenation potential of OIP was more positive than OBP, reflecting more facile reduction of OIP on Ag electrode. On the basis of in situ FTIR of OCP on Ag electrode, it was not obvious and the electrochemical reduction reaction was quite weak. Therefore, the order of electrochemical reductive dehalogenation was OIP > OBP > OCP.

NHC-CDI Betaine Adducts and Their Cationic Derivatives as Catalyst Precursors for Dichloromethane Valorization

Sánchez-Roa, David,Mosquera, Marta E. G.,Cámpora, Juan

, p. 16725 - 16735 (2021/11/18)

Zwitterionic adducts of N-heterocyclic carbene and carbodiimide (NHC-CDI) are an emerging class of organic compounds with promising properties for applications in various fields. Herein, we report the use of the ICyCDI(p-Tol) betaine adduct (1a) and its cationic derivatives2aand3aas catalyst precursors for the dichloromethane valorization via transformation into high added value products CH2Z2(Z = OR, SR or NR2). This process implies selective chloride substitution of dichloromethane by a range of nucleophiles Na+Z-(preformed or generatedin situfrom HZ and an inorganic base) to yield formaldehyde-derived acetals, dithioacetals, or aminals with full selectivity. The reactions are conducted in a multigram-scale under very mild conditions, using dichloromethane both as a reagent and solvent, and very low catalyst loading (0.01 mol %). The CH2Z2derivatives were isolated in quantitative yields after filtration and evaporation, which facilitates recycling the dichloromethane excess. Mechanistic studies for the synthesis of methylal CH2(OMe)2rule out organocatalysis as being responsible for the CH2transfer, and a phase-transfer catalysis mechanism is proposed instead. Furthermore, we observed that1aand2areact with NaOMe to form unusual isoureate ethers, which are the actual phase-transfer catalysts, with a strong preference for sodium over other alkali metal nucleophiles.

Dehydrogenative Coupling of Aldehydes with Alcohols Catalyzed by a Nickel Hydride Complex

Eberhardt, Nathan A.,Wellala, Nadeesha P. N.,Li, Yingze,Krause, Jeanette A.,Guan, Hairong

, p. 1468 - 1478 (2019/04/17)

A nickel hydride complex, {2,6-(iPr2PO)2C6H3}NiH, has been shown to catalyze the coupling of RCHO and R′OH to yield RCO2R′ and RCH2OH, where the aldehyde also acts as a hydrogen acceptor and the alcohol also serves as the solvent. Functional groups tolerated by this catalytic system include CF3, NO2, Cl, Br, NHCOMe, and NMe2, whereas phenol-containing compounds are not viable substrates or solvents. The dehydrogenative coupling reaction can alternatively be catalyzed by an air-stable nickel chloride complex, {2,6-(iPr2PO)2C6H3}NiCl, in conjunction with NaOMe. Acids in unpurified aldehydes react with the hydride to form nickel carboxylate complexes, which are catalytically inactive. Water, if present in a significant quantity, decreases the catalytic efficiency by forming {2,6-(iPr2PO)2C6H3}NiOH, which causes catalyst degradation. On the other hand, in the presence of a drying agent, {2,6-(iPr2PO)2C6H3}NiOH generated in situ from {2,6-(iPr2PO)2C6H3}NiCl and NaOH can be converted to an alkoxide species, becoming catalytically competent. The proposed catalytic mechanism features aldehyde insertion into the nickel hydride as well as into a nickel alkoxide intermediate, both of which have been experimentally observed. Several mechanistically relevant nickel species including {2,6-(iPr2PO)2C6H3}NiOC(O)Ph, {2,6-(iPr2PO)2C6H3}NiOPh, and {2,6-(iPr2PO)2C6H3}NiOPh·HOPh have been independently synthesized, crystallographically characterized, and tested for the catalytic reaction. While phenol-containing molecules cannot be used as substrates or solvents, both {2,6-(iPr2PO)2C6H3}NiOPh and {2,6-(iPr2PO)2C6H3}NiOPh·HOPh are efficient in catalyzing the dehydrogenative coupling of PhCHO with EtOH.

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