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110-59-8

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110-59-8 Usage

Chemical Properties

Clear liquid

Uses

Different sources of media describe the Uses of 110-59-8 differently. You can refer to the following data:
1. Valeronitrile is used as building block in organic synthesis. Product Data Sheet
2. Solvent.
3. Valeronitrile is used in the preparation of valeric acid. It is also used to enhance the nitrilase activity in many strains.

Production Methods

Valeronitrile can be synthesized by dehydration of valeronamide. The nitrile is also found in nature and is a constituent of coal gasification and oil shale processing waste water, sewage wastewater and tobacco smoke.

General Description

Clear colorless to yellow liquid.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Nitriles, such as Valeronitrile, may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids. Valeronitrile is incompatible with strong acids, strong bases, strong oxidizing agents and strong reducing agents. .

Health Hazard

Valeronitrile is an irritant and may be harmful by inhalation, ingestion or skin absorption .

Fire Hazard

Valeronitrile is combustible.

Industrial uses

Valeronitrile is used as an industrial solvent and as a chemical intermediate.

Metabolism

As with other aliphatic nitriles, valeronitrile is metabolized in vivo resulting in the liberation of cyanide ion which is responsible for much of the observed toxicity of this compound . Biotransformation of valeronitrile presumably proceeds in a manner similar to that of other aliphatic nitriles with an initial cytochrome P-450 catalyzed oxidation of the nitrile to the cyanohydrin followed by release of the cyanide group from the activated molecule. Cyanide formation was significantly reduced when valeronitrile was incubated with mouse hepatic microsomes in the presence of SKF-525A or carbon monoxide or when microsomes from mice pretreated with chloroform were used . Ethanol pretreatment of mice markedly increases the in vivo and in vitro microsomal oxidation of valeronitrile presumably as a result of increased levels of an ethanol inducible cytochrome P-450 . As with other nitriles, the cyanide released upon biotransformation of valeronitrile is readily converted to thiocyanate in vivo and the latter ion was the major urinary excretion product observed with valero-nitrile in rats . From 18 to 31% of a daily 175 mg/kg dose of valeronitrile was eliminated in the urine as thiocyanate during a 24 h period. In another study , 43.2 and 27.5%, respectively, of an oral or i.p. dose of 0.75 mmol/kg valeronitrile was excreted as thiocyanate in the urine of male Sprague-Dawley rats over a 24 h period.

Purification Methods

Wash the nitrile with half its volume of conc HCl (twice), then with saturated aqueous NaHCO3, dry it with MgSO4 and fractionally distil it from P2O5. [Beilstein 2 H 301, 2 I 131, 2 II 267, 2 III 675, 2 IV 875.]

Check Digit Verification of cas no

The CAS Registry Mumber 110-59-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 110-59:
(5*1)+(4*1)+(3*0)+(2*5)+(1*9)=28
28 % 10 = 8
So 110-59-8 is a valid CAS Registry Number.
InChI:InChI=1/C5H9N/c1-2-3-4-5-6/h2-4H2,1H3

110-59-8 Well-known Company Product Price

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  • CAS number
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  • Detail
  • Alfa Aesar

  • (A10306)  Valeronitrile, 99%   

  • 110-59-8

  • 25ml

  • 251.0CNY

  • Detail
  • Alfa Aesar

  • (A10306)  Valeronitrile, 99%   

  • 110-59-8

  • 100ml

  • 755.0CNY

  • Detail
  • Alfa Aesar

  • (A10306)  Valeronitrile, 99%   

  • 110-59-8

  • 500ml

  • 1804.0CNY

  • Detail

110-59-8SDS

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 Valeronitrile

1.2 Other means of identification

Product number -
Other names Butyl 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:110-59-8 SDS

110-59-8Synthetic route

1-bromo-butane
109-65-9

1-bromo-butane

sodium cyanide
143-33-9

sodium cyanide

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With PEG400 for 6h; Heating;96%
With methanol
With ethylene glycol
With ethanol; water
With 2-ethoxy-ethanol; potassium iodide
1-iodo-butane
542-69-8

1-iodo-butane

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
Stage #1: 2-hydroxy-2-methylpropanenitrile With lithium hydroxide monohydrate In tetrahydrofuran at 50℃; for 1h;
Stage #2: 1-iodo-butane In tetrahydrofuran
95.5%
1-pentanamine
110-58-7

1-pentanamine

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With oxygen In water at 30℃; under 760.051 Torr; for 7h; Catalytic behavior; Solvent; Wavelength; Irradiation;94%
With air; 15 wt% Na2H2[Si(W3O10)4] supported on γ-alumina at 180℃; under 760.051 Torr;
With oxygen In water at 99.84℃; under 22502.3 Torr; Sealed tube; Green chemistry;
With α,α,α-trifluorotoluene; Ru/γ-Al2O3; oxygen In acetonitrile at 33℃; under 760.051 Torr; for 6h; Irradiation; Green chemistry;
n-Butyl chloride
109-69-3

n-Butyl chloride

sodium cyanide
143-33-9

sodium cyanide

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With PEG400 for 7h; Heating;92%
With polyethylene glycol
pentanal
110-62-3

pentanal

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With hydroxylamine hydrochloride; pyrographite; methanesulfonyl chloride at 100℃; for 1.5h;90%
With ammonium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 20℃; for 10h;90%
With hydroxylamine hydrochloride; iron(II) sulfate In N,N-dimethyl-formamide for 4.5h; Reflux;90%
valeric acid
109-52-4

valeric acid

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With hydroxyammonium sulfate; zinc for 0.35h; Microwave irradiation;88%
With ammonium carbonate; diphosphorus tetraiodide In carbon disulfide at 20℃; for 9h;85%
With ammonia; silica gel at 500℃;
pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With 8-bromocaffeine; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.0111111h; Microwave irradiation; chemoselective reaction;88%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; N-tosylimidazole In N,N-dimethyl-formamide for 0.583333h; Reflux;86%
With acetyl chloride; zinc(II) oxide for 0.5h; Heating;85%
pent-2E-enal N,N-dimethylhydrazone

pent-2E-enal N,N-dimethylhydrazone

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With pyridine; dihydrogen peroxide; acetic acid; methyltrioxorhenium(VII) In water; acetonitrile for 0.25h;88%
pentamide
626-97-1

pentamide

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With C36H38Cl6N6Pd3S2 In water; acetonitrile at 80℃; for 6h; Reagent/catalyst;86%
With Pd3P0.95 In water; acetonitrile at 20℃; for 4h;70%
With ammonium sulphamate at 200℃;
Stage #1: pentamide 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;
2-amino-hexanoic acid
616-06-8

2-amino-hexanoic acid

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With pyridine; trichloroisocyanuric acid In water84.2%
1-bromo-butane
109-65-9

1-bromo-butane

sodium cyanide
773837-37-9

sodium cyanide

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With polyethylene glycol functionalized magnetic dicationic ionic liquid In water for 0.833333h; Reflux; Green chemistry;82%
dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

A

pentanonitrile
110-59-8

pentanonitrile

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
In acetonitrile at 20℃; for 4.5h;A 81%
B n/a
acetonitrile
75-05-8

acetonitrile

valeric acid
109-52-4

valeric acid

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With bis(acetylacetonate)oxovanadium In tetrachloromethane at 150℃; for 6h; Autoclave;78%
N'-hydroxypentanimidamide
67015-06-9

N'-hydroxypentanimidamide

A

pentanonitrile
110-59-8

pentanonitrile

B

pentamide
626-97-1

pentamide

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; acetonitrile at 20℃; for 0.666667h;A 14%
B 76%
With tetraethylammonium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 20℃; for 0.666667h;A 73%
B 14%
1,2-Epoxyhexane
1436-34-6

1,2-Epoxyhexane

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With ammonia; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; acetonitrile at 70℃;76%
With ammonia; iodine In water; acetonitrile at 70℃;71%
1-bromo-butane
109-65-9

1-bromo-butane

N,N,N',N',N'',N''-Hexamethylguanidiniumcyanid
68897-45-0

N,N,N',N',N'',N''-Hexamethylguanidiniumcyanid

A

pentanonitrile
110-59-8

pentanonitrile

B

1,1,2,2,3,3-Hexamethylguanidiniumbromid
6926-43-8

1,1,2,2,3,3-Hexamethylguanidiniumbromid

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h;A 75%
B n/a

A

pentan-1-ol
71-41-0

pentan-1-ol

B

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With N,N,N'N'-tetramethyl-1,3-propanediamine; carbon monoxide; water; hexarhodium hexadecacarbonyl In 2-ethoxy-ethanol at 40℃; under 6080 Torr; for 5h;A 17%
B 71%
1-bromo-butane
109-65-9

1-bromo-butane

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With N,N,N',N'-tetramethylguanidine In acetonitrile71%
Valeraldehyde N,N-dimethylhydrazone
14090-57-4

Valeraldehyde N,N-dimethylhydrazone

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With aluminum oxide; Oxone for 0.0833333h; microwave irradiation;68%
Caproamide
628-02-4

Caproamide

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With tetraethylammonium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 60℃; for 3.5h;60%
With sodium hypochlorite; tetra(n-butyl)ammonium hydrogensulfate; sodium phosphate; sodium bromide In water; benzene for 0.75h; Ambient temperature;55%
bis(O-isopropyl)xanthate

bis(O-isopropyl)xanthate

azobisvaleronitrile

azobisvaleronitrile

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
In 1,4-dioxane60%
ethylazodiphenylmethanol
75917-31-6

ethylazodiphenylmethanol

acrylonitrile
107-13-1

acrylonitrile

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
phenol In benzene at 35 - 50℃; for 16h;55%
1-pentanamine
110-58-7

1-pentanamine

A

pentanal
110-62-3

pentanal

B

pentanonitrile
110-59-8

pentanonitrile

C

N-pentylidenepentan-1-amine
65870-64-6

N-pentylidenepentan-1-amine

Conditions
ConditionsYield
With oxygen In water at 225℃; under 750.075 Torr; for 1h; Catalytic behavior; Mechanism; Time; Flow reactor;A n/a
B 54%
C n/a
{(μ-pentylidyne)diiron(Cp(CO))2(μ-CO)}PF6

{(μ-pentylidyne)diiron(Cp(CO))2(μ-CO)}PF6

A

cyclopentadienyl iron(II) dicarbonyl dimer
38117-54-3

cyclopentadienyl iron(II) dicarbonyl dimer

B

{C5H5(CO)Fe}2(μ-CO)(μ-CCHCH2CH2CH3)

{C5H5(CO)Fe}2(μ-CO)(μ-CCHCH2CH2CH3)

C

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With carbon monoxide; trimethylsilylazide In dichloromethane-d2 Flame sealing of Fe-compd. with Me3SiN3 (26°C), p-C6H4(SiMe3)2 and CD2Cl2 under 700 mmHg of CO in NMR tube; NMR identification after 14 h.;A 20%
B 22%
C 51%
With carbon monoxide; trimethylsilylazide In dichloromethane-d2 Flame sealing of Fe-compd. with Me3SiN3 (26°C), p-C6H4(SiMe3)2 and CD2Cl2 under 700 mmHg of CO in NMR tube; GC anal. of org. compd.;A n/a
B n/a
C 48%
propyl bromide
106-94-5

propyl bromide

acetonitrile
75-05-8

acetonitrile

A

pentanonitrile
110-59-8

pentanonitrile

B

di-N-propyl acetonitrile
13310-75-3

di-N-propyl acetonitrile

Conditions
ConditionsYield
With sodium In toluene for 2h; Irradiation;A 44%
B 20%
Cyclopentanone oxime
1192-28-5

Cyclopentanone oxime

A

pentanonitrile
110-59-8

pentanonitrile

B

δ-chlorovaleronitrile
6280-87-1

δ-chlorovaleronitrile

C

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With phosphorus pentachloride; 1-butyl-3-methylimidazolium Tetrafluoroborate at 80℃; for 2h; Beckmann fragmentation;A 4.7 % Chromat.
B 40.4%
C 54.9 % Chromat.
hex-1-yne
693-02-7

hex-1-yne

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With trimethylsilylazide; silver carbonate In dimethyl sulfoxide at 100℃; for 12h;39%
[(p-methylphenyl)sulfonylmethyl]isonitrile
38622-91-2, 36635-61-7

[(p-methylphenyl)sulfonylmethyl]isonitrile

butyraldehyde
123-72-8

butyraldehyde

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1,2-dimethoxyethane at -55℃; for 0.833333h;38%

A

pentanal
110-62-3

pentanal

B

pentanonitrile
110-59-8

pentanonitrile

Conditions
ConditionsYield
With chromium dichloride; Fe(meso-tetra-4-sulfonatophenyl)porphyrin; acetate buffer pH = 4.2; mercury; zinc In dichloromethane at 20℃; for 24h;A 37%
B 15%
ethanol
64-17-5

ethanol

pentanonitrile
110-59-8

pentanonitrile

ethyl valerimidate hydrochloride
18542-63-7

ethyl valerimidate hydrochloride

Conditions
ConditionsYield
With acetyl chloride at 0 - 20℃; for 17h;99%
With acetyl chloride at 0 - 20℃; for 19h; Cooling with ice;99%
With hydrogenchloride at 0℃; for 96h;76%
pentanonitrile
110-59-8

pentanonitrile

pentamide
626-97-1

pentamide

Conditions
ConditionsYield
With [RuH(tBu-PNP(-))(CO)]; water In tert-butyl alcohol at 50℃; for 24h;99%
With aluminum oxide; methanesulfonic acid at 120℃; for 0.25h;95%
With cesium hydroxide; water; dimethyl sulfoxide at 60℃; for 24h; Schlenk technique; Green chemistry;90%
pentanonitrile
110-59-8

pentanonitrile

valeric acid
109-52-4

valeric acid

Conditions
ConditionsYield
enzyme from Synechocystis sp. PCC 6803 In phosphate buffer at 30℃; for 12h; pH=7.2;99%
With benzene-1,2-dicarboxylic acid at 250℃; under 7600 Torr; for 0.5h; microwave irradiation;98%
With benzene-1,2-dicarboxylic acid at 240℃; under 3040 Torr; for 1h;91%
pentanonitrile
110-59-8

pentanonitrile

phenylmethanethiol
100-53-8

phenylmethanethiol

pentanimidothioic acid benzyl ester; hydrochloride

pentanimidothioic acid benzyl ester; hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether at 20℃; for 24h;99%
pentanonitrile
110-59-8

pentanonitrile

n-pentylamine hydrochloride
142-65-4

n-pentylamine hydrochloride

Conditions
ConditionsYield
With hydrogen at 130℃; under 750.075 Torr; for 20h; chemoselective reaction;99%
Stage #1: pentanonitrile With ammonia; hydrogen; cobalt(II) diacetate tetrahydrate; zinc trifluoromethanesulfonate; zinc In methanol at 120℃; under 30003 Torr; for 15h; Sealed tube; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether
96%
Stage #1: pentanonitrile With hydrogen; sodium triethylborohydride; cobalt(II) bromide In tetrahydrofuran at 110℃; under 15001.5 Torr; for 24h;
Stage #2: With hydrogenchloride In diethyl ether
72%
Multi-step reaction with 2 steps
1: potassium hydroxide / Raney nickel / 1 h / Heating
2: 2.88 g / hydrochloric acid / H2O / 0.25 h
View Scheme
tetramethylammonium tetrachloroplatinate(II)

tetramethylammonium tetrachloroplatinate(II)

pentanonitrile
110-59-8

pentanonitrile

cis-[Pt(CH3(CH2)3CN)2Cl2]
94598-76-2, 176486-88-7, 176486-89-8

cis-[Pt(CH3(CH2)3CN)2Cl2]

Conditions
ConditionsYield
In not given excess nitrile;99%
pentanonitrile
110-59-8

pentanonitrile

potassium phenyltrifluoborate

potassium phenyltrifluoborate

phenyl butyl ketone
1009-14-9

phenyl butyl ketone

Conditions
ConditionsYield
With [2,2]bipyridinyl; palladium(II) trifluoroacetate; water; trifluoroacetic acid In tetrahydrofuran at 80℃; for 36h; Inert atmosphere; Schlenk technique;99%
pentanonitrile
110-59-8

pentanonitrile

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

N-(4-chlorobenzyl)pentan-1-aminium chloride

N-(4-chlorobenzyl)pentan-1-aminium chloride

Conditions
ConditionsYield
Stage #1: pentanonitrile; 4-chlorobenzaldehyde With hydrogen In 2-methyltetrahydrofuran at 100℃; under 11251.1 Torr; for 20h; High pressure; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether
99%
pentanonitrile
110-59-8

pentanonitrile

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

N-(3-chlorobenzyl)pentan-1-aminium chloride
90389-50-7

N-(3-chlorobenzyl)pentan-1-aminium chloride

Conditions
ConditionsYield
Stage #1: pentanonitrile; m-Chlorobenzaldehyde With hydrogen In 2-methyltetrahydrofuran at 100℃; under 11251.1 Torr; for 20h; High pressure; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether
99%
pentanonitrile
110-59-8

pentanonitrile

4-tert-Butylbenzaldehyde
939-97-9

4-tert-Butylbenzaldehyde

N-(4-(tert-butyl)benzyl)pentan-1-aminium chloride

N-(4-(tert-butyl)benzyl)pentan-1-aminium chloride

Conditions
ConditionsYield
Stage #1: pentanonitrile; 4-tert-Butylbenzaldehyde With hydrogen In 2-methyltetrahydrofuran at 100℃; under 11251.1 Torr; for 20h; High pressure; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether
99%
p-benzyloxybenzaldehyde
4397-53-9

p-benzyloxybenzaldehyde

pentanonitrile
110-59-8

pentanonitrile

N-(4-(benzyloxy)benzyl)pentan-1-aminium chloride

N-(4-(benzyloxy)benzyl)pentan-1-aminium chloride

Conditions
ConditionsYield
Stage #1: p-benzyloxybenzaldehyde; pentanonitrile With hydrogen In 2-methyltetrahydrofuran at 100℃; under 11251.1 Torr; for 20h; High pressure; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether
99%
pentanonitrile
110-59-8

pentanonitrile

benzaldehyde
100-52-7

benzaldehyde

N-benzylpentan-1-aminium chloride
90389-36-9

N-benzylpentan-1-aminium chloride

Conditions
ConditionsYield
Stage #1: pentanonitrile; benzaldehyde With hydrogen In 2-methyltetrahydrofuran at 100℃; under 11251.1 Torr; for 20h; High pressure; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether
99%
pentanonitrile
110-59-8

pentanonitrile

diethyl chlorophosphate
814-49-3

diethyl chlorophosphate

diethyl 1-cyanobutylphosphonate
34491-77-5

diethyl 1-cyanobutylphosphonate

Conditions
ConditionsYield
Stage #1: pentanonitrile With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.5h; Metallation;
Stage #2: diethyl chlorophosphate In tetrahydrofuran at -78 - 0℃; for 0.25h; Substitution;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane Hydrolysis; Further stages.;
98%
pentanonitrile
110-59-8

pentanonitrile

tripentylamine
621-77-2

tripentylamine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In cyclohexane at 25℃; under 760.051 Torr; for 6h;98%
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 50℃; under 1125.11 Torr; for 5h; Catalytic behavior; Solvent;
pentanonitrile
110-59-8

pentanonitrile

2,2-dimethylmalononitrile
7321-55-3

2,2-dimethylmalononitrile

benzyl bromide
100-39-0

benzyl bromide

2-benzyl-2-propylmalononitrile

2-benzyl-2-propylmalononitrile

Conditions
ConditionsYield
Stage #1: pentanonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: 2,2-dimethylmalononitrile In tetrahydrofuran; hexane at 20 - 80℃; for 6h; Inert atmosphere;
Stage #3: benzyl bromide In tetrahydrofuran; hexane; N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;
98%
n-Octylamine
111-86-4

n-Octylamine

pentanonitrile
110-59-8

pentanonitrile

N,N-diamyloctylamine
1352347-50-2

N,N-diamyloctylamine

Conditions
ConditionsYield
With palladium 10% on activated carbon; ammonium acetate; hydrogen In methanol at 20℃; under 760.051 Torr; for 29h;97%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

pentanonitrile
110-59-8

pentanonitrile

2-(trimethylsilyl)pentanenitrile

2-(trimethylsilyl)pentanenitrile

Conditions
ConditionsYield
Stage #1: pentanonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.0833333h; Inert atmosphere;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -78 - 25℃; for 2h; Inert atmosphere;
97%
pentanonitrile
110-59-8

pentanonitrile

pentanimidamide
109-51-3

pentanimidamide

Conditions
ConditionsYield
Stage #1: pentanonitrile With hydrogenchloride In ethanol at 20℃;
Stage #2: With ammonia In ethanol at 20℃; for 0.166667h;
96.1%
With ammonia; potassium amide
pentanonitrile
110-59-8

pentanonitrile

5-n-butyl-1H-tetrazole
66281-98-9

5-n-butyl-1H-tetrazole

Conditions
ConditionsYield
With sodium azide; ammonium chloride In N,N-dimethyl-formamide at 135℃; for 68h;96%
With sodium azide at 120℃; for 1.25h;91%
With sodium azide at 130℃; for 0.883333h; Catalytic behavior;90%
methanol
67-56-1

methanol

pentanonitrile
110-59-8

pentanonitrile

methyl pentanimidate
57246-71-6

methyl pentanimidate

Conditions
ConditionsYield
Stage #1: methanol; pentanonitrile With hydrogenchloride at -10 - 15℃; under 1103.36 - 1471.14 Torr; for 30 - 33h;
Stage #2: With ammonia In methanol at 20 - 30℃; for 3h; pH=8 - 9;
96%
With hydrogenchloride
With hydrogenchloride In dibutyl ether at 4℃; for 144h; Addition;190.8 g
pentanonitrile
110-59-8

pentanonitrile

ethyl 2-bromomethyl-2-propenoate
17435-72-2

ethyl 2-bromomethyl-2-propenoate

2-(2-Butyl-4-methylene-5-oxo-pyrrolidin-2-ylmethyl)-acrylic acid ethyl ester

2-(2-Butyl-4-methylene-5-oxo-pyrrolidin-2-ylmethyl)-acrylic acid ethyl ester

Conditions
ConditionsYield
With zinc In tetrahydrofuran for 2h; Heating;96%
pentanonitrile
110-59-8

pentanonitrile

dimethyl 2,2-di(but-2-yn-1-yl)malonate
107428-05-7

dimethyl 2,2-di(but-2-yn-1-yl)malonate

dimethyl 3-butyl-1,4-dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridine-6,6-dicarboxylate
1325229-33-1

dimethyl 3-butyl-1,4-dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridine-6,6-dicarboxylate

Conditions
ConditionsYield
With 1,3-bis-(diphenylphosphino)propane; ferrous iodide; zinc In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; regioselective reaction;96%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

pentanonitrile
110-59-8

pentanonitrile

N-diphenylmethylpentanamide
10253-98-2

N-diphenylmethylpentanamide

Conditions
ConditionsYield
With silica-bonded N-propylsulphamic acid In neat (no solvent) at 80℃; for 0.75h; Ritter Amidation; Green chemistry;96%
With aluminum(III) hydrogen sulfate In nitromethane at 100℃; for 2h; Ritter Amidation;90%
pentanonitrile
110-59-8

pentanonitrile

dimethyl 2-vinylcyclopropane-1,1-dicarboxylate
17447-60-8

dimethyl 2-vinylcyclopropane-1,1-dicarboxylate

dimethyl 2-butyl-5-vinyl-4,5-dihydro-3H-pyrrole-3,3-dicarboxylate
1519050-34-0

dimethyl 2-butyl-5-vinyl-4,5-dihydro-3H-pyrrole-3,3-dicarboxylate

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 0 - 25℃; for 0.0833333h;96%
pentanonitrile
110-59-8

pentanonitrile

cyclopropyl(4-fluorophenyl)methanone
772-31-6

cyclopropyl(4-fluorophenyl)methanone

C15H20FNO2

C15H20FNO2

Conditions
ConditionsYield
With tributylphosphine; boron trifluoride diethyl etherate; water; copper(I) bromide In nitromethane at 85℃; for 18h;96%
pentanonitrile
110-59-8

pentanonitrile

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

N-(2-chlorobenzyl)pentan-1-aminium chloride

N-(2-chlorobenzyl)pentan-1-aminium chloride

Conditions
ConditionsYield
Stage #1: pentanonitrile; 2-chloro-benzaldehyde With hydrogen In 2-methyltetrahydrofuran at 100℃; under 11251.1 Torr; for 20h; High pressure; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether
96%
pentanonitrile
110-59-8

pentanonitrile

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

N-(4-methoxybenzyl)pentan-1-aminium chloride

N-(4-methoxybenzyl)pentan-1-aminium chloride

Conditions
ConditionsYield
Stage #1: pentanonitrile; 4-methoxy-benzaldehyde With hydrogen In 2-methyltetrahydrofuran at 100℃; under 11251.1 Torr; for 20h; High pressure; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether
96%

110-59-8Related news

Structure and Catalytic Properties in Hydrogenation of Valeronitrile (cas 110-59-8) of Raney Nickel Prepared from Cr and Mo Doped Ni2Al3 Alloys.08/23/2019

SummaryRaney nickel catalysts, unpromoted or doped with molybdenum or chromium, were prepared from the precursor alloys of the type Ni2Al3. The structure and phase composition of the catalysts have been determined. Hydrogenation of valeronitrile at 90°C and 1.6 MPa- in cyclohexane was performed...detailed

110-59-8Relevant articles and documents

Regen et al.

, p. 2029 (1979)

A convenient procedure for the preparation of alkyl nitriles from alkyl halides. Acetone cyanohydrin as an in situ source of cyanide ion

Dowd,Wilk,Wlostowski

, p. 2323 - 2329 (1993)

A convenient preparation of alkyl nitriles from alkyl halides is described. Acetone cyanohydrin is employed as the source of cyanide ion.

Whitesides,G.M. et al.

, p. 5258 - 5270 (1972)

Deprotonation-alkylation of alkyl cyanides under sonochemical conditions

Berlan,Delmas,Duee,Luche,Vuiglio

, p. 1253 - 1260 (1994)

Deprotonation-alkylation of n-alkyl cyanides can be readily effected by an alkyl halide in the presence of sodium in a one pot procedure. Yields are generally better than in the usual methods, and the overall reaction conditions have important advantages

-

Tanner,D.D.,Bunce,N.J.

, p. 3028 - 3034 (1969)

-

Downie,Lee

, p. 855 (1967)

Cavity-promotion by pillar[5]arenes expedites organic photoredox-catalysed reductive dehalogenations

Esser, Birgit,Schmidt, Maximilian

supporting information, p. 9582 - 9585 (2021/09/28)

The efficiency of the photo-induced electron transfer in photoredox catalysis is limited by the diffusional collision of the excited catalyst and the substrate. We herein present cavity-bound photoredox catalysts, which preassociate the substrates, leading to significantly shortened reaction times. A pillar[5]arene serves as the cavity and phenothiazine as a catalyst in the reductive dehalogenation of aliphatic bromides as a proof of concept reaction.

Conversion of Dinitrogen into Nitrile: Cross-Metathesis of N2-Derived Molybdenum Nitride with Alkynes

Hong, Xin,Jin, Li,Liao, Qian,Mézailles, Nicolas,Song, Jinyi

supporting information, p. 12242 - 12247 (2021/04/05)

The direct synthesis of nitrile from N2 under mild conditions is of great importance and has attracted much interest. Herein, we report a direct conversion of N2 into nitrile via a nitrile–alkyne cross-metathesis (NACM) process involving a N2-derived Mo nitride. Treatment of the Mo nitride with alkyne in the presence of KOTf afforded an alkyne-coordinated nitride, which was then transformed into MoV carbyne and the corresponding nitrile upon 1 e? oxidation. Both aryl- and alkyl-substituted alkynes underwent this process smoothly. Experiments and DFT calculations have proved that the oxidation state of the Mo center plays a crucial role. This method does not rely on the nucleophilicity of the N2-derived metal nitride, offering a novel strategy for N2 fixation chemistry.

NHC-catalyzed silylative dehydration of primary amides to nitriles at room temperature

Ahmed, Jasimuddin,Hota, Pradip Kumar,Maji, Subir,Mandal, Swadhin K.,Rajendran, N. M.

supporting information, p. 575 - 578 (2020/01/29)

Herein we report an abnormal N-heterocyclic carbene catalyzed dehydration of primary amides in the presence of a silane. This process bypasses the energy demanding 1,2-siloxane elimination step usually required for metal/silane catalyzed reactions. A detailed mechanistic cycle of this process has been proposed based on experimental evidence along with computational study.

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