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
110-59-8Relevant 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.