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767-00-0 Usage

Chemical Properties

white crystalline powder or chips

Uses

Different sources of media describe the Uses of 767-00-0 differently. You can refer to the following data:
1. Intermediates of Liquid Crystals
2. 4-Cyanophenol is a precursor for the synthesis of a vasodilator, Levcromakalim. Bromination of 4-cyanophenol results in bromoxynil, a commercial herbicide. It can also be used as a component of deep eutectic solvent (DES) mixture.

Preparation

4-Cyanophenol is produced by reaction of 4-bromophenol with copper (I) cyanide, by ammoxidation of p-cresol, by reaction of 4-chlorobenzonitrile with sodium methoxide, or by the catalyzed gas phase reaction of ethyl 4-hydroxybenzoate with ammonia.

Purification Methods

Crystallise the phenol from pet ether, *benzene or water and keep it under vacuum over P2O5. [Bernasconi & Paschelis J Am Chem Soc 108 2969 1986.] [Beilstein 10 H 167, 10 IV 441.]

Check Digit Verification of cas no

The CAS Registry Mumber 767-00-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,6 and 7 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 767-00:
(5*7)+(4*6)+(3*7)+(2*0)+(1*0)=80
80 % 10 = 0
So 767-00-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H5NO/c8-5-6-1-3-7(9)4-2-6/h1-4,9H/p-1

767-00-0 Well-known Company Product Price

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

  • (A15803)  4-Hydroxybenzonitrile, 98+%   

  • 767-00-0

  • 50g

  • 687.0CNY

  • Detail
  • Alfa Aesar

  • (A15803)  4-Hydroxybenzonitrile, 98+%   

  • 767-00-0

  • 100g

  • 1137.0CNY

  • Detail
  • Alfa Aesar

  • (A15803)  4-Hydroxybenzonitrile, 98+%   

  • 767-00-0

  • 250g

  • 2417.0CNY

  • Detail
  • Alfa Aesar

  • (A15803)  4-Hydroxybenzonitrile, 98+%   

  • 767-00-0

  • 500g

  • 4110.0CNY

  • Detail
  • Sigma-Aldrich

  • (45528)  4-Hydroxybenzonitrile  PESTANAL®, analytical standard

  • 767-00-0

  • 45528-250MG

  • 255.06CNY

  • Detail

767-00-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-cyanophenol

1.2 Other means of identification

Product number -
Other names para-hydroxybenzonitrile

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:767-00-0 SDS

767-00-0Synthetic route

4-cyanophenyl acetate
13031-41-9

4-cyanophenyl acetate

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate; thiophenol for 0.25h; Hydrolysis; Heating;100%
With potassium hydroxide In ethanol for 0.333333h; Heating;88%
With sodium tetrahydroborate; cobalt(II) chloride In ethanol at 0 - 25℃; for 10h;83%
With N-butylamine; Tetraethylene glycol dimethyl ether In chlorobenzene at 25℃; Rate constant; efficacy of glyme catalysis, other glymes;
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride at 100℃; for 0.25h; Condensation; microwave irradiation;100%
With oxygen; copper; ammonium chloride In pyridine at 60℃; for 24h;99%
With sodium azide; trifluorormethanesulfonic acid In acetonitrile at 20℃; for 0.0333333h; Schmidt reaction;99%
4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With calcium hydride; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 220℃; for 0.5h;100%
With sodium methylate; 1-dodecylthiol In N,N-dimethyl-formamide at 100℃; for 1h;97%
With cyclohexa-1,4-diene; 3,6-bis(dimethylamino)-9H-carbazole; caesium carbonate In dimethyl sulfoxide at 23℃; for 48h; Inert atmosphere; Schlenk technique; Irradiation;94%
4-allyloxy-benzonitrile
33148-47-9

4-allyloxy-benzonitrile

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With calcium hydride; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 220℃; for 0.5h;100%
With tetrabutylammonium tetrafluoroborate; tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; electrolysis: Mg rod anode, carbon fibre cathode, const. current 60 mA;99%
With aniline; (ϖ-allyl)palladium triflate based catalyst at 30℃; for 0.333333h;99%
(E)-4-hydroxybenzaldehyde oxime
60221-52-5

(E)-4-hydroxybenzaldehyde oxime

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at 20℃; for 4h; Beckmann rearrangement;100%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 4 A molecular sieve In acetonitrile at 80℃; for 0.5h;99%
for 0.0583333h; Dehydration; Irradiation;82%
4-cyanophenyl benzoate
16513-72-7

4-cyanophenyl benzoate

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate; thiophenol for 0.25h; Hydrolysis; debenzoylation; Heating;100%
With potassium fluoride; thiophenol In 1-methyl-pyrrolidin-2-one at 100℃; for 1h;85%
With sodium; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 90℃; for 0.25h;84%
With potassium carbonate In 1-methyl-pyrrolidin-2-one for 0.333333h; Heating;80%
4-cyanophenyl acetate
13031-41-9

4-cyanophenyl acetate

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

A

2-Methylbenzothiazole
120-75-2

2-Methylbenzothiazole

B

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 0.5h; Hydrolysis; cyclization;A n/a
B 100%
2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

4-cyanophenyl pivalate
180143-65-1

4-cyanophenyl pivalate

A

2-(tert-butyl)benzo[d]thiazole
17626-88-9

2-(tert-butyl)benzo[d]thiazole

B

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 1.5h; Hydrolysis; cyclization;A n/a
B 100%
4-benzyloxybenzonitrile
52805-36-4

4-benzyloxybenzonitrile

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With calcium hydride; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 220℃; for 0.5h;100%
With hydrogen; palladium on activated charcoal; ethylenediamine In tetrahydrofuran at 20℃; for 24h; atmospheric pressure;100%
With cyclohexa-1,4-diene; 3,6-bis(dimethylamino)-9H-carbazole; caesium carbonate In dimethyl sulfoxide at 23℃; for 18h; Inert atmosphere; Schlenk technique; Irradiation;99%
sodium cyanide
143-33-9

sodium cyanide

4-chloro-phenol
106-48-9

4-chloro-phenol

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With nickel dibromide In 1-methyl-pyrrolidin-2-one at 200℃; under 10343 Torr; for 0.333333h; microwave irradiation;99%
4-Iodophenol
540-38-5

4-Iodophenol

copper(l) cyanide

copper(l) cyanide

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With tetrabutylammomium bromide In water at 170℃; under 10343.2 Torr; for 0.0833333h; microwave irradiation;99%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With β-D-glucose; copper(II) acetate monohydrate; potassium hydroxide In water; dimethyl sulfoxide at 20 - 120℃; for 28h;99%
With bis(η3-allyl-μ-chloropalladium(II)); p-methylbenzaldehyde oxime; caesium carbonate; tert-butyl XPhos In tetrahydrofuran at 75℃; for 2h; Inert atmosphere;98%
With cesiumhydroxide monohydrate; t-BuBrettPhos; C44H62NO5PPdS; water In 1,4-dioxane at 20℃; for 18h; Inert atmosphere;97%
4-cyanophenylboronic acid
126747-14-6

4-cyanophenylboronic acid

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In water; acetonitrile for 30h; Irradiation;99%
With oxygen; triethylamine In acetonitrile at 20℃; under 760.051 Torr; for 4h; Reagent/catalyst; Irradiation;99%
With water; caesium carbonate; hydrazine hydrate at 80℃; for 12h;98%
4-(dimethylsilyl)benzonitrile
129409-68-3

4-(dimethylsilyl)benzonitrile

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With water; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; methanol at 20℃; for 5h;99%
Multi-step reaction with 2 steps
1: (p-cymene)ruthenium(II) chloride / 0.08 h / 20 °C
2: tetrabutyl ammonium fluoride; water; dihydrogen peroxide; potassium hydrogencarbonate / tetrahydrofuran; methanol / 0.5 h / 20 °C
View Scheme
With dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran-d8; d(4)-methanol at 20℃; Kinetics; Mechanism;
4-benzyloxybenzonitrile
52805-36-4

4-benzyloxybenzonitrile

A

4-cyanophenol
767-00-0

4-cyanophenol

B

toluene
108-88-3

toluene

Conditions
ConditionsYield
With 0.5%Pd/TiO2; isopropyl alcohol In water at 24.84℃; for 2h; Inert atmosphere; Sealed tube; Irradiation;A 99%
B 99%
4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With phosphorus pentoxide; urea at 160℃; for 1h; Temperature;98.2%
With hydroxyammonium sulfate; zinc for 0.316667h; Microwave irradiation;91%
With phosphoramide; sodium chloride at 450℃; for 1.5h;68%
Multi-step reaction with 2 steps
1: ammonia / 0.5 h / 250 °C
2: 1 h / 325 °C
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid / cyclohexane / 10 h / 90 °C
2: ammonium hydroxide / 5 h / 100 °C / Autoclave
3: resin catalyst supported with palladium salt / water; acetonitrile / 7 h / 50 °C
View Scheme
4-hydroxybenzaldehyde oxime
699-06-9, 60221-52-5, 60221-53-6

4-hydroxybenzaldehyde oxime

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With thionyl chloride; sodium sulfite at 0℃; for 0.0166667h;98%
With thionyl chloride; silica gel In dichloromethane at 0℃; for 0.116667h;98%
With acetonitrile for 1h; Reflux; Green chemistry;98%
potassium (4-cyanophenyl)trifluoroborate
850623-36-8

potassium (4-cyanophenyl)trifluoroborate

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With Oxone; water In acetone at 20℃; for 0.0333333h;98%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

4-Iodophenol
540-38-5

4-Iodophenol

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With copper (II) trifluoroacetate hydrate; palladium diacetate In dimethyl sulfoxide at 130℃; for 6h; Sealed tube; Inert atmosphere;98%
dihydrogen peroxide
7722-84-1

dihydrogen peroxide

4-cyanophenylboronic acid
126747-14-6

4-cyanophenylboronic acid

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;97%
methanethiosulfonic acid S-methyl ester
2949-92-0

methanethiosulfonic acid S-methyl ester

C16H18N2O5S2

C16H18N2O5S2

A

C9H17NO3S3

C9H17NO3S3

B

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With diethylenetriaminopentaacetic acid In aq. phosphate buffer; acetonitrile at 37℃; pH=7.4;A n/a
B 97%
Ethyl 4-hydroxybenzoate
120-47-8

Ethyl 4-hydroxybenzoate

A

4-cyanophenol
767-00-0

4-cyanophenol

B

phenol
108-95-2

phenol

Conditions
ConditionsYield
With ammonia; boron phosphate at 400℃; for 0.000277778h;A 96%
B 5%
A 95%
B n/a
A 93.8% by weight.
B n/a
p-hydroxybenzamide
619-57-8

p-hydroxybenzamide

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With resin catalyst supported with palladium salt In water; acetonitrile at 50℃; for 7h; Temperature;96%
With trichloromethyl chloroformate In various solvent(s) 0-5 deg C then heated to 60 deg C, 5 min;94%
Stage #1: p-hydroxybenzamide With C39H45N2 In acetonitrile at 20℃; Schlenk technique; Glovebox; Inert atmosphere;
Stage #2: With phenylsilane In acetonitrile at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;
94%
4-cyanophenyl propyl ether
60758-84-1

4-cyanophenyl propyl ether

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 200 - 220℃; for 0.5h; Microwave irradiation; Inert atmosphere;96%
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; Kinetics; Electrolysis;
(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With trichloroisocyanuric acid; ammonia In water at 20 - 60℃;96%
With potassium hydroxide; ammonium bicarbonate; (Bu4N)2S2O8; copper(II) formate; nikel(II) formate In isopropyl alcohol at 25℃; for 1.5h;91%
With ammonia; oxygen In 1,4-dioxane for 2.5h; Reflux;91%
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

A

4-cyanophenol
767-00-0

4-cyanophenol

B

phenol
108-95-2

phenol

Conditions
ConditionsYield
With ammonia; boron phosphate at 400℃; for 0.00111111h;A 95%
B 5%
4-fluorobenzonitrile
1194-02-1

4-fluorobenzonitrile

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With 2-(methylsulfonyl)ethyl alcohol; sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;95%
With acetylhydroxamic acid; potassium carbonate In dimethyl sulfoxide at 80℃; for 16h; Sealed tube;93%
With methyl propargyl alcohol; potassium tert-butylate In dimethyl sulfoxide at 125℃; for 0.0333333h; microwave irradiation;90%
4-(tert-butoxycarbonyloxy)benzonitrile
1040380-15-1

4-(tert-butoxycarbonyloxy)benzonitrile

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With methanol; carbon tetrabromide; triphenylphosphine for 1h; Reflux;95%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere;95%
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere;95%
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;88%
4-hydroxyphenylacetate
156-38-7

4-hydroxyphenylacetate

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With oxygen; copper(II) trifluoroacetate; urea In dimethyl sulfoxide at 95℃; for 16h; Green chemistry;95%
With 1,10-Phenanthroline; oxygen; copper(II) oxide; potassium ferrocyanide In dimethyl sulfoxide at 120℃; under 11251.1 Torr; for 40h; Autoclave;36%
4-cyanophenol
767-00-0

4-cyanophenol

allyl bromide
106-95-6

allyl bromide

4-allyloxy-benzonitrile
33148-47-9

4-allyloxy-benzonitrile

Conditions
ConditionsYield
With caesium carbonate In water; N,N-dimethyl-formamide at 20℃; for 12h;100%
With potassium carbonate In acetone at 20℃; for 24h;99%
With potassium carbonate In acetone at 20℃; for 20h; Reflux;98%
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.
acetic anhydride
108-24-7

acetic anhydride

4-cyanophenol
767-00-0

4-cyanophenol

4-cyanophenyl acetate
13031-41-9

4-cyanophenyl acetate

Conditions
ConditionsYield
With magnesium(II) perchlorate at 80℃; for 0.25h;100%
With thalium(III) chloride tetrahydrate at 20℃; for 0.0333333h;97%
With aluminum triflate at 20℃; for 0.00833333h;96%
benzyl bromide
100-39-0

benzyl bromide

4-cyanophenol
767-00-0

4-cyanophenol

4-benzyloxybenzonitrile
52805-36-4

4-benzyloxybenzonitrile

Conditions
ConditionsYield
With sodium carbonate In acetone for 16h; Reflux;100%
With potassium carbonate In acetone for 5h; Heating;98%
With potassium carbonate In acetone Reflux;98%
ethyl bromide
74-96-4

ethyl bromide

4-cyanophenol
767-00-0

4-cyanophenol

4-ethoxybenzonitrile
25117-74-2

4-ethoxybenzonitrile

Conditions
ConditionsYield
With sodium In ethanol for 24h; Heating;100%
With potassium carbonate In acetone Reflux;100%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

4-cyanophenol
767-00-0

4-cyanophenol

4-cyanophenyl trifluoromethanesulfonate
66107-32-2

4-cyanophenyl trifluoromethanesulfonate

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane at 20℃; for 16h;100%
With pyridine In dichloromethane at 20℃; for 1h;96%
With potassium phosphate In water; toluene at 0 - 20℃;96%
4-cyanophenol
767-00-0

4-cyanophenol

acetyl chloride
75-36-5

acetyl chloride

4-cyanophenyl acetate
13031-41-9

4-cyanophenyl acetate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 12h;100%
In benzene Heating;
With pyridine In diethyl ether
With triethylamine In dichloromethane at 0 - 5℃;
4-cyanophenol
767-00-0

4-cyanophenol

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

4-(4-nitrophenoxy)benzonitrile
17076-68-5

4-(4-nitrophenoxy)benzonitrile

Conditions
ConditionsYield
With cesium fluoride/clinoptilolite In dimethyl sulfoxide at 110℃; for 0.5h; Ullmann Condensation;100%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h;99%
With potassium hydroxide In dimethyl sulfoxide at 55℃;98%
1-bromo-hexane
111-25-1

1-bromo-hexane

4-cyanophenol
767-00-0

4-cyanophenol

1-(4-cyanophenyl)oxyhexane
66052-06-0

1-(4-cyanophenyl)oxyhexane

Conditions
ConditionsYield
In potassium carbonate100%
With sodium hydride In N,N-dimethyl-formamide 1.) rt, 1 h, 2.) reflux, 12 h;90%
With potassium carbonate In cyclohexanone for 24h; Heating;70%
4-cyanophenol
767-00-0

4-cyanophenol

benzoic acid anhydride
93-97-0

benzoic acid anhydride

4-cyanophenyl benzoate
16513-72-7

4-cyanophenyl benzoate

Conditions
ConditionsYield
With magnesium(II) perchlorate at 80℃; for 0.75h;100%
With potassium tropolonato In acetonitrile at 70℃; for 4h;80%
methanol
67-56-1

methanol

4-cyanophenol
767-00-0

4-cyanophenol

4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

Conditions
ConditionsYield
With bis-(2-(1-adamantyl)ethyl) azodicarboxylate; triphenylphosphine Mitsunobu reaction;100%
ethyl 2-bromoisobutyrate
600-00-0

ethyl 2-bromoisobutyrate

4-cyanophenol
767-00-0

4-cyanophenol

2-(4-cyanophenoxy)-2-methylpropionic acid ethyl ester
18672-07-6

2-(4-cyanophenoxy)-2-methylpropionic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 4-cyanophenol With potassium carbonate In acetonitrile for 1h; Heating / reflux;
Stage #2: ethyl 2-bromoisobutyrate With potassium carbonate for 72h; Heating / reflux;
100%
Stage #1: 4-cyanophenol With potassium carbonate In N,N-dimethyl-formamide for 0.166667h;
Stage #2: ethyl 2-bromoisobutyrate In N,N-dimethyl-formamide at 20℃; for 16h;
69%
Stage #1: 4-cyanophenol With potassium carbonate In acetone at 20℃; for 0.5h;
Stage #2: ethyl 2-bromoisobutyrate In acetone for 16h; Heating / reflux;
46.9%
4-cyanophenol
767-00-0

4-cyanophenol

propargyl bromide
106-96-7

propargyl bromide

3-(p-cyanophenoxy)-1-propyne
33143-80-5

3-(p-cyanophenoxy)-1-propyne

Conditions
ConditionsYield
With potassium carbonate In acetone; toluene for 24h; Williamson Ether Synthesis; Reflux;100%
Stage #1: 4-cyanophenol With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.5h;
Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene at 80℃; for 15h;
97%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5h; Inert atmosphere;95%
(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol
1136-52-3

(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol

4-cyanophenol
767-00-0

4-cyanophenol

4-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethoxy)-benzonitrile
885337-94-0

4-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethoxy)-benzonitrile

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 1.5h;100%
4-cyanophenol
767-00-0

4-cyanophenol

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

methyl 2-(4-cyanophenoxy)acetate
272792-14-0

methyl 2-(4-cyanophenoxy)acetate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 70℃; for 1.5h;100%
With potassium carbonate In acetonitrile at 20℃;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

4-cyanophenol
767-00-0

4-cyanophenol

4-(tert-butoxycarbonyloxy)benzonitrile
1040380-15-1

4-(tert-butoxycarbonyloxy)benzonitrile

Conditions
ConditionsYield
With 6,7-dimethoxyisoquinoline In dichloromethane at 20℃; for 10h; Inert atmosphere; chemoselective reaction;100%
Stage #1: 4-cyanophenol With dmap; triethylamine In dichloromethane for 0.25h;
Stage #2: di-tert-butyl dicarbonate In dichloromethane for 2h;
100%
triphenylphosphine at 40℃; for 14h;97%
4-cyanophenol
767-00-0

4-cyanophenol

2,4-dinitrophenyl benzoate
1523-15-5

2,4-dinitrophenyl benzoate

A

4-cyanophenyl benzoate
16513-72-7

4-cyanophenyl benzoate

B

potassium 2,4-dinitrophenolate
14314-69-3

potassium 2,4-dinitrophenolate

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 25℃; for 5h;A 100%
B n/a
4-cyanophenol
767-00-0

4-cyanophenol

2-bromobutyric acid ethyl ester
533-68-6

2-bromobutyric acid ethyl ester

Ethyl 2-(4-cyanophenoxy)butanoate
79228-67-4

Ethyl 2-(4-cyanophenoxy)butanoate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; for 3h;100%
With potassium carbonate In acetonitrile at 80℃; for 3h;100%
Isobutyl bromide
78-77-3

Isobutyl bromide

4-cyanophenol
767-00-0

4-cyanophenol

4-(2-methylpropoxy)benzonitrile
5203-15-6

4-(2-methylpropoxy)benzonitrile

Conditions
ConditionsYield
With potassium iodide In N,N-dimethyl-formamide at 60℃; for 10h; Reagent/catalyst; Solvent; Temperature;100%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 6h;98.5%
With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 70℃; for 18h;98%
2-chloropyridine
109-09-1

2-chloropyridine

4-cyanophenol
767-00-0

4-cyanophenol

4-(pyridin-2-yloxy)benzonitrile
270260-33-8

4-(pyridin-2-yloxy)benzonitrile

Conditions
ConditionsYield
With C45H65FeNO3P2PdS; caesium carbonate In toluene at 100℃; for 24h; Inert atmosphere; Sealed tube;100%
4-cyanophenol
767-00-0

4-cyanophenol

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

1-bromomethyl-3-methoxybenzene

4-((3-methoxybenzyl)oxy)benzonitrile

4-((3-methoxybenzyl)oxy)benzonitrile

Conditions
ConditionsYield
With potassium carbonate In acetone for 4h; Reflux;100%

767-00-0Relevant articles and documents

Bis(4-cyanophenyl) phenyl phosphate as viscosity reducing comonomer for phthalonitrile resins

Terekhov,Aleshkevich,Afanaseva,Nechausov,Babkin,Bulgakov,Kepman,Avdeev

, p. 34 - 41 (2019)

Bis(4-cyanophenyl) phenyl phosphate (CPP) is introduced for the first time as a viscosity reducing comonomer for phthalonitrile resins. In comparison to the common phthalonitrile resins, the blends of CPP with 4,4′-[benzene-1,3-diylbis(oxy)]diphthalonitrile demonstrated advanced processing properties suitable for cost-effective injection processing (η as low as to 180 mPa?s at 100 °C). Thermal copolymerization was performed indicating complete inclusion of bis-benzonitrile CPP into the phthalonitrile network resulting in formation of thermosets with great thermal performance. Hydrolysis of CPP at pH 4, 7, and 10 was studied to confirm its suitability as a reactive diluent for phthalonitrile. Conversion vs. time plots were obtained via HPLC analysis, and pseudo-first order rate constants were determined in the range of 25–80 °C. The activation parameters were calculated from the Arrhenius equation.

Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes

Ding, Guangni,Fan, Sijie,Wang, Jingyang,Wang, Yu,Wu, Xiaoyu,Xie, Xiaomin,Yang, Liqun,Zhang, Zhaoguo

supporting information, (2021/09/28)

An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD)2 as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of key intermediates, mechanism studies confirm that the deallylation undergoes η3-allylnickel intermediate pathway.

Highly Efficient Oxidative Cyanation of Aldehydes to Nitriles over Se,S,N-tri-Doped Hierarchically Porous Carbon Nanosheets

Hua, Manli,Song, Jinliang,Huang, Xin,Liu, Huizhen,Fan, Honglei,Wang, Weitao,He, Zhenhong,Liu, Zhaotie,Han, Buxing

supporting information, p. 21479 - 21485 (2021/08/23)

Oxidative cyanation of aldehydes provides a promising strategy for the cyanide-free synthesis of organic nitriles. Design of robust and cost-effective catalysts is the key for this route. Herein, we designed a series of Se,S,N-tri-doped carbon nanosheets with a hierarchical porous structure (denoted as Se,S,N-CNs-x, x represents the pyrolysis temperature). It was found that the obtained Se,S,N-CNs-1000 was very selective and efficient for oxidative cyanation of various aldehydes including those containing other oxidizable groups into the corresponding nitriles using ammonia as the nitrogen resource below 100 °C. Detailed investigations revealed that the excellent performance of Se,S,N-CNs-1000 originated mainly from the graphitic-N species with lower electron density and synergistic effect between the Se, S, N, and C in the catalyst. Besides, the hierarchically porous structure could also promote the reaction. Notably, the unique feature of this metal-free catalyst is that it tolerated other oxidizable groups, and showed no activity on further reaction of the products, thereby resulting in high selectivity. As far as we know, this is the first work for the synthesis of nitriles via oxidative cyanation of aldehydes over heterogeneous metal-free catalysts.

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