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104-47-2

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104-47-2 Usage

Chemical Properties

Clear colorless to slightly yellow liquid

Uses

Different sources of media describe the Uses of 104-47-2 differently. You can refer to the following data:
1. 4-Methoxybenzyl cyanide is used in the biosynthesis of p-methoxyphenylacetic acid by immobilized Bacillus subtilis ZJB-063.
2. 4-Methoxyphenylacetonitrile was used as starting reagent in the synthesis of :2-(1-cyano-1-(2-methoxy)phenyl)methylidene-3-phenylthiazolidine-4,5-dione2-(1-cyano-1-(4-methoxy)-phenyl)methylidene-3-phenylthiazolidine-4,5-dione α-cyanostilbenes

Synthesis Reference(s)

Journal of Medicinal Chemistry, 15, p. 214, 1972 DOI: 10.1021/jm00272a029Synthesis, p. 40, 1987 DOI: 10.1055/s-1987-27834

General Description

4-Methoxyphenylacetonitrile has been isolated from the sponge Psammaplysilla purpurea.

Check Digit Verification of cas no

The CAS Registry Mumber 104-47-2 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 4 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 104-47:
(5*1)+(4*0)+(3*4)+(2*4)+(1*7)=32
32 % 10 = 2
So 104-47-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H9NO/c1-11-9-4-2-8(3-5-9)6-7-10/h2-5H,6H2,1H3

104-47-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A15056)  4-Methoxyphenylacetonitrile, 98%   

  • 104-47-2

  • 25g

  • 215.0CNY

  • Detail
  • Alfa Aesar

  • (A15056)  4-Methoxyphenylacetonitrile, 98%   

  • 104-47-2

  • 100g

  • 592.0CNY

  • Detail

104-47-2SDS

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 4-Methoxyphenylacetonitrile

1.2 Other means of identification

Product number -
Other names 4-Methoxybenzyl Cyanide

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:104-47-2 SDS

104-47-2Synthetic route

C22H18N2O5

C22H18N2O5

A

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

B

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 94%
B 100%
lysichitalexin
31236-71-2

lysichitalexin

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With dmap; Sn(thiophenolate)4; tributylphosphine; diethylazodicarboxylate In dichloromethane at 0℃; for 0.0833333h;99%
Multi-step reaction with 3 steps
1: 83 percent / NaNO2, NaOH / methanol / 0 °C
2: 63 percent / Et3N / CH2Cl2 / Ambient temperature
3: 94 percent / Bu3SnH, AIBN / benzene / Heating
View Scheme
Multi-step reaction with 2 steps
1: tris(2,2'-bipyridyl)ruthenium(II)chloride hexahydrate; N-ethyl-N,N-diisopropylamine; magnesium(II) perchlorate / acetonitrile / 12 h / 20 °C / Inert atmosphere; Irradiation
2: triphenylphosphine; iodine / dichloromethane / 8 h / 20 °C / Inert atmosphere
View Scheme
1-(isocyanomethyl)-4-methoxybenzene
1197-58-6

1-(isocyanomethyl)-4-methoxybenzene

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
at 520 - 550℃; under 0.01 Torr;98%
With 1,1-Diphenylethylene In various solvent(s) at 210℃; Rate constant; Thermodynamic data; ΔG(excit.) <250 deg C>; ΔH(excit.), ΔS(excit.);101 % Chromat.
With 1,1-diphenylene; chlorobenzene In benzene at 170℃; Rate constant; Thermodynamic data; also at 190, 210 and 230 deg C; ΔHY (excit.), ΔΔHY-H(excit.), ΔSY(excit.), ΔΔSY-H(excit);
2-(4-methoxyphenyl)acetamide
6343-93-7

2-(4-methoxyphenyl)acetamide

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With triethylamine; ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate In ethyl acetate at 20℃; for 1h; Inert atmosphere;98%
With thionyl chloride In benzene Reflux;
2-(4-methoxy-benzyloxy)-tetrahydro-pyran
18494-82-1

2-(4-methoxy-benzyloxy)-tetrahydro-pyran

tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 3h; Heating;95%
C9H11Cl2NO

C9H11Cl2NO

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With TEA In dichloromethane at 25℃; for 2h;95%
2-(4-methoxyphenyl)acetohydroxamic acid
2594-06-1

2-(4-methoxyphenyl)acetohydroxamic acid

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With phosphorus tribromide In benzene for 5h; Heating;93%
2-[(Z)-Hydroxyimino]-3-(4-methoxy-phenyl)-propionic acid
139109-50-5

2-[(Z)-Hydroxyimino]-3-(4-methoxy-phenyl)-propionic acid

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole In benzene 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h;93%
4-methoxy-1-(methoxymethoxy)methyl benzene
92565-78-1

4-methoxy-1-(methoxymethoxy)methyl benzene

tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With 1-methyl-3H-imidazolium nitrate at 135 - 140℃; for 0.05h; Microwave irradiation;93%
With phosphotungstic acid at 130 - 142℃; for 0.05h; Microwave irradiation; Ionic liquid; chemoselective reaction;88%
With 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0916667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;82%
tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20℃;92%
4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

sodium cyanoacetate
1071-36-9

sodium cyanoacetate

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(η3-allyl-μ-chloropalladium(II)) In 1,3,5-trimethyl-benzene at 20 - 140℃; for 5.16667h; Inert atmosphere; Sealed tube; chemoselective reaction;92%
(E)-2-(4-methoxyphenyl)acetaldehyde oxime
128224-91-9

(E)-2-(4-methoxyphenyl)acetaldehyde oxime

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With iodine; triphenylphosphine In dichloromethane at 20℃; for 8h; Inert atmosphere;92%
ethyl 4-(4-methoxyphenyl)-5-methyl-isoxazole-3-carboxylate

ethyl 4-(4-methoxyphenyl)-5-methyl-isoxazole-3-carboxylate

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With potassium fluoride In water; N,N-dimethyl-formamide at 125℃; for 16h; Inert atmosphere;91%
2-(hydroxyimino)-3-(4-methoxyphenyl)propanoic acid
3682-16-4

2-(hydroxyimino)-3-(4-methoxyphenyl)propanoic acid

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With 1,1'-oxalyldiimidazole In benzene 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h;90%
With acetic anhydride at 100℃;
sodium cyanide
143-33-9

sodium cyanide

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With triethylamine; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide for 3h; Heating;90%
4-Methoxyphenylacetic acid
104-01-8

4-Methoxyphenylacetic acid

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With sodium azide; TEA; triethylphosphine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane; dimethyl sulfoxide at 0℃; for 30h;90%
2-(4-methoxyphenyl)acetaldehyde oxime
3353-51-3

2-(4-methoxyphenyl)acetaldehyde oxime

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With triethylamine; ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate In ethyl acetate at 20℃; for 1h; Inert atmosphere;90%
With p-toluenesulfonyl chloride In acetonitrile at 0℃; for 8h; Inert atmosphere;
4-Methoxyphenethylamine
55-81-2

4-Methoxyphenethylamine

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With TEA; trichloroisocyanuric acid In N,N-dimethyl-formamide at 15℃; for 4h;89%
With iodine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 65℃; for 1.5h;58%
With HRu(1,3-bis(6'-methyl-2'-pyridylimino)isoindoline)(PPh3)2 In toluene at 110℃; for 24h; Inert atmosphere; Glovebox; chemoselective reaction;48%
With [Ru(p-cymene)(pzH-NP)(Cl)]Cl; potassium tert-butylate In toluene at 70℃; for 24h; Schlenk technique; Inert atmosphere;43%
sodium cyanide
773837-37-9

sodium cyanide

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With polyethylene glycol functionalized magnetic dicationic ionic liquid In water for 1h; Reflux; Green chemistry;88%
In ethanol; water for 4h; Reflux;58%
In acetonitrile Reflux;
In acetonitrile for 4h; Reflux;
4-cyanomethylphenol
14191-95-8

4-cyanomethylphenol

methyl iodide
74-88-4

methyl iodide

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
Stage #1: 4-cyanomethylphenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 72h; Inert atmosphere;
87%
With potassium hydroxide
With potassium hydroxide at 100℃;
sodium cyanide
143-33-9

sodium cyanide

1-(4-Methoxy-benzyl)-2-methylsulfanyl-4,6-diphenyl-pyridinium; iodide
76950-80-6

1-(4-Methoxy-benzyl)-2-methylsulfanyl-4,6-diphenyl-pyridinium; iodide

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 24h; Heating;87%
C10H12BrNO2
137042-70-7

C10H12BrNO2

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With acetic acid; zinc In N,N-dimethyl-formamide at 150℃; for 0.5h;86%
With sodium carbonate In methanol for 2h; Irradiation;80%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With sodium nitrite In water; toluene at 50℃; for 24h; Schlenk technique;86%
sodium cyanide
143-33-9

sodium cyanide

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
In dimethyl sulfoxide85%
With acetone; potassium iodide
In dimethyl sulfoxide at 45 - 50℃; for 5h;
With acetone; potassium iodide
copper(l) cyanide

copper(l) cyanide

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
In tetrahydrofuran at 80℃; for 11h;82%
4-methoxy-1-[(ethoxymethoxy)methyl]benzene
1058649-04-9

4-methoxy-1-[(ethoxymethoxy)methyl]benzene

tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0916667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;82%
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

chloroacetonitrile
107-14-2

chloroacetonitrile

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate In 1,4-dioxane; water at 60℃; for 12h; Inert atmosphere; Sealed tube;81%
1'p.methoxyphenyl 1'-cyano 1,3,5,5-tetramethyl 2-cyclohexen 1-ol
77797-05-8

1'p.methoxyphenyl 1'-cyano 1,3,5,5-tetramethyl 2-cyclohexen 1-ol

A

3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

B

p-methoxyphenyl-3' cyano-3' tetramethyl-3,3,5,5 cyclohexanone
77797-11-6

p-methoxyphenyl-3' cyano-3' tetramethyl-3,3,5,5 cyclohexanone

C

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -70℃; for 0.0833333h; Yield given;A n/a
B 80%
C n/a
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -70℃; for 0.0833333h; Yields of byproduct given;A n/a
B 80%
C n/a
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

p-methoxybenzyl acetate
104-21-2

p-methoxybenzyl acetate

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With iron(III) trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 2h;78%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

tri-n-butyl(cyanomethyl)stannane
17729-59-8

tri-n-butyl(cyanomethyl)stannane

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
dichlorobis(tri-O-tolylphosphine)palladium In m-xylene at 120℃; for 3h;77%
p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

methyl 2-cyano-2-(4-methoxyphenyl) acetate
30698-32-9

methyl 2-cyano-2-(4-methoxyphenyl) acetate

Conditions
ConditionsYield
With sodium hydride In toluene; mineral oil at 80℃; for 5.5h;100%
With sodium hydride In toluene at 80℃; for 5h; Inert atmosphere; Cooling with ice;81%
With sodium methylate In methanol; toluene at 75 - 80℃; for 12h;42%
mechlorethamine hydrochloride
55-86-7

mechlorethamine hydrochloride

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

4-(4-methoxyphenyl)-1-methylpiperidine-4-carbonitrile
487013-52-5

4-(4-methoxyphenyl)-1-methylpiperidine-4-carbonitrile

Conditions
ConditionsYield
With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 60℃; for 24h;100%
With tetra(n-butyl)ammonium hydrogensulfate In sodium hydroxide20%
p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

3-oxa-1,5-dichloropentane
111-44-4

3-oxa-1,5-dichloropentane

4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-carbonitrile
3648-78-0

4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-carbonitrile

Conditions
ConditionsYield
Stage #1: p-methoxybenzylnitrile With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.5h;
Stage #2: 3-oxa-1,5-dichloropentane In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 2.33333h;
100%
Stage #1: p-methoxybenzylnitrile With sodium hydroxide In N,N-dimethyl-formamide for 0.5h;
Stage #2: 3-oxa-1,5-dichloropentane In N,N-dimethyl-formamide at 80 - 100℃; for 5h;
69%
With sodium hydride In N,N-dimethyl-formamide; mineral oil Cooling with ice;64%
With NaH In dimethyl sulfoxide
(Z)-N-benzylidenebenzylamine N-oxide
77681-22-2, 3376-26-9, 85225-56-5

(Z)-N-benzylidenebenzylamine N-oxide

Triethylsilyl trifluoromethanesulfonate
79271-56-0

Triethylsilyl trifluoromethanesulfonate

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

3-(benzyl((triethylsilyl)oxy)amino)-2-(4-methoxyphenyl)-3-phenylpropanenitrile

3-(benzyl((triethylsilyl)oxy)amino)-2-(4-methoxyphenyl)-3-phenylpropanenitrile

Conditions
ConditionsYield
With triethylamine In 1,2-dichloro-ethane at -30℃; for 0.5h; Inert atmosphere;100%
p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

4-methoxyphenethylamine hydrochloride
645-58-9

4-methoxyphenethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen In propan-1-ol; water at 60℃; under 375.038 Torr; for 18h; Flow reactor;100%
Stage #1: p-methoxybenzylnitrile With MnBr(CO)2[NH(CH2CH2P(iPr)2)2]; hydrogen; sodium t-butanolate In toluene at 120℃; under 37503.8 Torr; for 36h; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether
96%
Stage #1: p-methoxybenzylnitrile With borane-ammonia complex; C17H16BrMnN2O3S In hexane at 60℃; for 6h;
Stage #2: With hydrogenchloride In diethyl ether; water
96%
Stage #1: p-methoxybenzylnitrile With ammonium hydroxide; hydrogen In water; isopropyl alcohol at 130℃; under 30003 Torr; for 2h; Autoclave;
Stage #2: With hydrogenchloride In methanol
85%
Multi-step reaction with 2 steps
1: hydrogen; ammonium hydroxide / isopropyl alcohol / 15 h / 120 °C / 22502.3 Torr / Autoclave
2: hydrogenchloride / methanol
View Scheme
p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

1-Phenylbut-1-en-3-one
122-57-6

1-Phenylbut-1-en-3-one

(methoxy-4 phenyl)-1 phenyl-2 oxo-4 pentane carbonitrile
102118-66-1, 102118-67-2, 114879-80-0, 114879-87-7

(methoxy-4 phenyl)-1 phenyl-2 oxo-4 pentane carbonitrile

Conditions
ConditionsYield
With sodium methylate In methanol for 4h; Ambient temperature;99%
With tetrabutylammomium bromide; potassium carbonate In toluene at 50℃; for 6h;70%
p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

4-Bromo-5,6-dimethyl-furo[2,3-d]pyrimidine
161644-02-6

4-Bromo-5,6-dimethyl-furo[2,3-d]pyrimidine

(5,6-Dimethyl-furo[2,3-d]pyrimidin-4-yl)-(4-methoxy-phenyl)-acetonitrile

(5,6-Dimethyl-furo[2,3-d]pyrimidin-4-yl)-(4-methoxy-phenyl)-acetonitrile

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 130℃; for 0.5h;99%
ethyl-2-picolinate
2524-52-9

ethyl-2-picolinate

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

5-amino-6-(4-methoxyphenyl)-1-pyridine-7-one

5-amino-6-(4-methoxyphenyl)-1-pyridine-7-one

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -10 - 20℃; Condensation; cyclization;99%
{1-[chloro(p-tolylsulfinyl)methyl]cyclobutyl}acetonitrile
854139-16-5

{1-[chloro(p-tolylsulfinyl)methyl]cyclobutyl}acetonitrile

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

6-amino-7-(4-methoxyphenyl)spiro[3.4]octa-5,7-diene-5-carbonitrile
854139-25-6

6-amino-7-(4-methoxyphenyl)spiro[3.4]octa-5,7-diene-5-carbonitrile

Conditions
ConditionsYield
Stage #1: {1-[chloro(p-tolylsulfinyl)methyl]cyclobutyl}acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: p-methoxybenzylnitrile With n-butyllithium In tetrahydrofuran at -78 - -40℃; for 1.5h; Further stages.;
99%
C-phenyl-N-methylnitrone
3376-23-6, 7372-59-0, 59862-60-1

C-phenyl-N-methylnitrone

Triethylsilyl trifluoromethanesulfonate
79271-56-0

Triethylsilyl trifluoromethanesulfonate

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

2-(4-methoxyphenyl)-3-(methyl((triethylsilyl)oxy)amino)-3-phenylpropanenitrile

2-(4-methoxyphenyl)-3-(methyl((triethylsilyl)oxy)amino)-3-phenylpropanenitrile

Conditions
ConditionsYield
With triethylamine In 1,2-dichloro-ethane at -30℃; for 0.5h; Inert atmosphere;99%
terephthalaldehyde,
623-27-8

terephthalaldehyde,

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

1,4-bis(4-methoxy-α-cyanostyryl)benzene

1,4-bis(4-methoxy-α-cyanostyryl)benzene

Conditions
ConditionsYield
With sodium methylate In methanol; ethanol at 20℃; for 0.166667h;99%
With sodium ethanolate In ethanol at 40℃; for 0.666667h; Knoevenagel Condensation;91%
p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

isopropyl bromide
75-26-3

isopropyl bromide

2-(4-methoxyphenyl)-3-methylbutyronitrile
51632-18-9

2-(4-methoxyphenyl)-3-methylbutyronitrile

Conditions
ConditionsYield
With sodium hydroxide; triethylamine In water98.7%
With sodium hydroxide In benzene81%
With sodium hydroxide In benzene81%
benzaldehyde
100-52-7

benzaldehyde

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

(Z)-2-(4-methoxyphenyl)-3-phenylpropenenitrile
54648-50-9

(Z)-2-(4-methoxyphenyl)-3-phenylpropenenitrile

Conditions
ConditionsYield
With potassium hydroxide In ethanol98%
With sodium methylate In methanol at 30℃; Kinetics; Thermodynamic data; ΔE*, ς*, A;95%
With sodium methylate In ethanol at 20℃; for 2h;93%
p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

2-(4-methoxyphenyl)acetamide
6343-93-7

2-(4-methoxyphenyl)acetamide

Conditions
ConditionsYield
With dihydrogen peroxide; potassium carbonate In dimethyl sulfoxide for 0.333333h; Ambient temperature;98%
With Os(hydride)6(triisopropylphosphine)2; water In tetrahydrofuran-d8 at 100℃; for 24h; Inert atmosphere;95%
With tetra(n-butyl)ammonium hydroxide In ethanol; water at 80℃; for 8h; Green chemistry; chemoselective reaction;90%
cyclohexanone
108-94-1

cyclohexanone

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

1-[cyano(4-methoxyphenyl)methyl]cyclohexanol
93413-76-4

1-[cyano(4-methoxyphenyl)methyl]cyclohexanol

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In methanol at 25 - 30℃; for 6h;98%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate at 0 - 15℃; for 1h;97%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water at 0 - 15℃; for 2.2h;97.6%
p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

allyl bromide
106-95-6

allyl bromide

diphenyldisulfane
882-33-7

diphenyldisulfane

2-(4-Methoxy-phenyl)-2-phenylsulfanyl-pent-4-enenitrile
85624-02-8

2-(4-Methoxy-phenyl)-2-phenylsulfanyl-pent-4-enenitrile

Conditions
ConditionsYield
With potassium hydroxide98%
2-Aminonicotinaldehyde
7521-41-7

2-Aminonicotinaldehyde

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

2-amino-3-(p-methoxyphenyl)-1,8-naphthyridine
60467-64-3

2-amino-3-(p-methoxyphenyl)-1,8-naphthyridine

Conditions
ConditionsYield
With piperidine at 20℃; for 0.133333h;98%
With potassium hydroxide Microwave irradiation;
With piperidine In neat (no solvent) at 20℃;
p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

benzyl alcohol
100-51-6

benzyl alcohol

2-(4-methoxyphenyl)-3-phenylpropanenitrile
5840-58-4

2-(4-methoxyphenyl)-3-phenylpropanenitrile

Conditions
ConditionsYield
With potassium tert-butylate; C35H27Cl2N4PRuS In toluene at 135℃; for 1h; Inert atmosphere; Schlenk technique;98%
With C41H44ClIrN2O4; potassium hydroxide In toluene at 135℃; for 2h; Reagent/catalyst;96%
With potassium hydroxide; [IrCP*Cl2]2 at 100℃; for 16h;93%
C15H10N2O

C15H10N2O

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

C24H17N3O

C24H17N3O

Conditions
ConditionsYield
With sodium methylate In methanol; ethanol at 20℃; for 0.166667h; Knoevenagel Condensation;98%
C17H13NO2

C17H13NO2

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

1,4-bis(4-methoxy-α-cyanostyryl)benzene

1,4-bis(4-methoxy-α-cyanostyryl)benzene

Conditions
ConditionsYield
With sodium methylate In methanol; ethanol at 20℃; for 0.166667h; Knoevenagel Condensation;98%
C14H9NOS

C14H9NOS

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

C23H16N2OS

C23H16N2OS

Conditions
ConditionsYield
With sodium methylate In methanol; ethanol at 20℃; for 0.166667h; Knoevenagel Condensation;98%
methyl 2,4-bis(benzyloxy)-5-bromobenzoate
958253-44-6

methyl 2,4-bis(benzyloxy)-5-bromobenzoate

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

3-(2,4-bis(benzyloxy)-5-bromophenyl)-2-(4-methoxyphenyl)-3-oxopropanenitrile

3-(2,4-bis(benzyloxy)-5-bromophenyl)-2-(4-methoxyphenyl)-3-oxopropanenitrile

Conditions
ConditionsYield
Stage #1: p-methoxybenzylnitrile With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: methyl 2,4-bis(benzyloxy)-5-bromobenzoate In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere;
97.2%
Stage #1: p-methoxybenzylnitrile With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: methyl 2,4-bis(benzyloxy)-5-bromobenzoate In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere;
97.2%
p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

ethyl 2-(4-methoxyphenyl)acetimidate hydrochloride
58125-69-2

ethyl 2-(4-methoxyphenyl)acetimidate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 4℃; for 72h;97%
With hydrogenchloride In ethanol
With hydrogenchloride In ethanol at 0 - 5℃;
ethyl iodide
75-03-6

ethyl iodide

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

2-ethyl-2-(4-methoxyphenyl)butanenitrile
51558-09-9

2-ethyl-2-(4-methoxyphenyl)butanenitrile

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 20h; Cooling with ice;97%
p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

C21H35B2NO5

C21H35B2NO5

Conditions
ConditionsYield
With C26H50N6Zn2 In neat (no solvent) at 60℃; Schlenk technique; Glovebox;97%
With Os(hydride)6(triisopropylphosphine)2 In (2)H8-toluene; 1,3,5-trimethyl-benzene at 60℃; for 48h; Sealed tube; Inert atmosphere;69%
With [κ2-{2-F-C6H4NP(Se)Ph2}2Al(Me)] In neat (no solvent) at 60℃; for 10h; Schlenk technique; Glovebox; Inert atmosphere; chemoselective reaction;80 %Spectr.
C23H19NOS

C23H19NOS

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

(Z)-3-(4-((E)-2-(10-ethyl-10H-phenothiazin-3-yl)vinyl)phenyl)-2-(4-methoxyphenyl)acrylonitrile

(Z)-3-(4-((E)-2-(10-ethyl-10H-phenothiazin-3-yl)vinyl)phenyl)-2-(4-methoxyphenyl)acrylonitrile

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydroxide In ethanol for 2h; Reflux;97%

104-47-2Relevant articles and documents

Antimicrobial volatile glucosinolate autolysis products from Hornungia petraea (L.) Rchb. (Brassicaceae)

Radulovi?, Niko S.,Deki?, Milan S.,Stojanovi?-Radi?, Zorica Z.

, p. 351 - 357 (2012)

Plant samples of Hornungia petraea were analyzed for glucosinolate (GLS) autolysis metabolites for the first time. GC-MS analysis of the autolysate and the synthesis of a series (12 compounds) of possible glucosinolate breakdown products revealed/corroborated the presence of glucoaubrietin, glucolimnanthin, glucolepigramin and glucotropaeolin in this species as the most likely "mustard oil" precursors. GLS degradation products identified in the autolysate of H. petraea, benzyl isothiocyanate, 3- and 4-methoxybenzyl isothiocyanate, along with several other structurally related compounds were evaluated for antimicrobial activity in order to possibly pinpoint the role of the latter secondary metabolites in the plant tissues. The assays showed a very high antibacterial activity of the tested isothiocyanates against Sarcina lutea and an antifungal effect against Aspergillus fumigatus and Candida albicans with MIC values in the order of 1 μg/ml value.

Conversion of Alcohols, Thiols, and Trimethysilyl Ethers to Alkyl Cyanides Using Triphenylphosphine/2,3-Dichlorol-5,6-dicyanobenzoquinone/n-Bu 4NCN

Iranpoor, Nasser,Firouzabadi, Habib,Akhlaghinia, Batool,Nowrouzi, Najmeh

, p. 2562 - 2564 (2004)

Triphenylphosphine and 2,3-dichloro-5,6-dicyanobenzoquinone afford an adduct, which in the presence of n-Bu4NCN converts alcohols, thiols, and trimethylsilyl ethers into their corresponding alkyl cyanides in good to excellent yields at room tem

Synthesis of alkyl iodides/nitriles from carbonyl compounds using novel ruthenium tris(2,2,6,6-tetramethyl-3,5-heptanedionate) as catalyst

Bhor, Malhari D.,Panda, Anil G.,Nandurkar, Nitin S.,Bhanage, Bhalchandra M.

, p. 6475 - 6479 (2008)

Aldehydes and ketones were hydrogenated to the corresponding alcohols, which were then transformed in situ into their respective iodides and nitriles in good yields. A structurally well-defined O-containing transition metal complex, Ru (TMHD)3, was found to be the active catalyst for hydrogenation, iodination and cyanation reactions. It has high affinity for the transformation of benzylic alcohols to iodides and nitriles.

A Facile Synthesis of Nitriles from 1-Nitro-1-alkenes by Electroreduction

Sera, Akira,Tani, Hiroyuki,Nishiguchi, Ikuzo,Hirashima, Tsuneaki

, p. 631 - 633 (1987)

Electroreduction of 1-nitro-1-alkenes in the presence of titanium(IV) chloride affords nitriles in good yields.This procedure provides a facile transformation of aldehydes to one-carbon elongated nitriles since the 1-nitro-1-alkenes are best prepared from aldehydes and nitromethane.

A simple one-pot procedure for the direct conversion of alcohols into alkyl nitriles using TsIm

Soltani Rad, Mohammad Navid,Khalafi-Nezhad, Ali,Behrouz, Somayeh,Faghihi, Mohammad Ali

, p. 6779 - 6784 (2007)

A convenient and efficient one-pot preparation of nitriles from alcohols using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, treatment of alcohols with a mixture of NaCN, TsIm and triethylamine in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in refluxing DMF furnishes the corresponding alkyl nitriles in good yields. This methodology is highly efficient for various structurally diverse alcohols with selectivity for ROH: 1° > 2° > 3°.

-

Kindler,Schrader

, p. 190 (1950)

-

A heterogeneous palladium catalyst hybridised with a titanium dioxide photocatalyst for direct C-C bond formation between an aromatic ring and acetonitrile

Yoshida, Hisao,Fujimura, Yuki,Yuzawa, Hayato,Kumagai, Jun,Yoshida, Tomoko

, p. 3793 - 3795 (2013)

A palladium catalyst hybridised with a titanium dioxide photocatalyst can promote cyanomethylation of an aromatic ring by using acetonitrile, where the photocatalyst activates acetonitrile to form a cyanomethyl radical before the C-C bond formation using the palladium catalyst.

Synthesis of heterocyclic ketene N,O-acetals from 5(2H)-isoxazolones

Beccalli, Egle M.,Marchesini, Alessandro,Pilati, Tullio

, p. 10433 - 10440 (1997)

Starting from 4-aryl isoxazolin-5-ones 1, a new synthesis of heterocyclic ketene N,O-acetals is described.

From Stoichiometric Reagents to Catalytic Partners: Selenonium Salts as Alkylating Agents for Nucleophilic Displacement Reactions in Water

Martins, Nayara Silva,ángel, Alix Y. Bastidas,Anghinoni, Jo?o M.,Lenard?o, Eder J.,Barcellos, Thiago,Alberto, Eduardo E.

supporting information, p. 87 - 93 (2021/11/03)

The ability of chalcogenium salts to transfer an electrophilic moiety to a given nucleophile is well known. However, up to date, these reagents have been used in stoichiometric quantities, producing a substantial amount of waste as byproducts of the reaction. In this report, we disclose further investigation of selenonium salts as S-adenosyl-L-methionine (SAM) surrogates for the alkylation of nucleophiles in aqueous solutions. Most importantly, we were able to convert the stoichiometric process to a catalytic system employing as little as 10 mol % of selenides to accelerate the reaction between benzyl bromide and other alkylating agents with sodium cyanide in water. Probe experiments including 77Se NMR and HRMS of the reaction mixture have unequivocally shown the presence of the selenonium salt in the reaction mixture. (Figure presented.).

Assembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides

Chen, Ying,Xu, Lanting,Jiang, Yongwen,Ma, Dawei

supporting information, p. 7082 - 7086 (2021/02/26)

α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and ethyl cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls.

Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles

Pirola, Margherita,Faverio, Chiara,Orlandi, Manuel,Benaglia, Maurizio

supporting information, p. 10247 - 10250 (2021/06/18)

A metal-free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β-substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α-functionalized nitriles were obtained with no loss of enantiomeric excess. The methodology was successfully applied to the synthesis of chiral β-cyano esters, α-aryl alkylnitriles, and TBS-protected cyanohydrins, including direct precursors of four active pharmaceutical ingredients (ibuprofen, tembamide, aegeline and denopamine).

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