544-13-8

Usage

Uses

Used in Chemical Industry:
Glutaronitrile is used as a chemical intermediate for the synthesis of various compounds and materials. Its ability to react with different reagents makes it a valuable component in the production of a wide range of products.
Used in Electrolyte Additive for Li-ion Batteries:
Glutaronitrile is used as an electrolyte additive in high energy/power Li-ion batteries. Its addition to the electrolyte improves the battery's performance and stability, making it a crucial component in the development of advanced battery technologies.
Used in Preparation of Zinc Glutarate (ZnGA):
Glutaronitrile serves as a glutarate ligand source to prepare zinc glutarate (ZnGA) by reacting with zinc perchlorate hexahydrate. This reaction is essential in the production of zinc glutarate, which has various applications in different industries.
Used in Synthesis of Pentanedithioamide:
Glutaronitrile is used as a reactant to synthesize pentanedithioamide by reacting with Lawesson's reagent in the presence of boron trifluoride etherate (BF3.OEt2). This synthesis process is vital for the production of pentanedithioamide, which has its own set of applications in various fields.

Safety Profile

Poison by subcutaneous route. Moderately toxic by ingestion. When heated to decomposition it emits very toxic fumes of NOx and CN-. See also NITRILES.

Upstream product

• 2873-74-7 gloutaric dichloride 
• 5666-55-7 (phenylsulfonyl)phosphorimidic trichloride 
• 10479-84-2 (E)-Pent-2-endinitril 
• 64-17-5 ethanol 
• 151-50-8 potassium cyanide 
• 109-70-6 1.3-chlorobromopropane 
• 143-33-9 sodium cyanide 
• 109-64-8 1,3-dibromo-propane 
• 37114-87-7 1,3-Propandiol-bis-benzolsulfonat 
• 108-94-1 cyclohexanone 
• 13435-20-6 tetraethylammoniumcyanide 
• 81675-41-4 2-phenylsulphonylglutaronitrile 
• 107-13-1 acrylonitrile 
• 75-05-8 acetonitrile 

Downstream Products

• 16093-48-4 1,5-bis-(2,4,6-trihydroxy-phenyl)-pentane-1,5-dione 
• 872272-53-2 6,6-dibenzyl-piperidin-2-one-imine 
• 110-89-4 piperidine 
• 462-94-2 1,5-diaminopentane 
• 35027-30-6 C₄₅H₃₆N₄O₂ 
• 7707-25-7 Glutarsaeure-diamidrazon 
• 14157-57-4 1,4,8,11-Tetraamino-1,11-diphenyl-2,3,9,10-tetraaza-undeca-1,3,8,10-tetraen 
• 99939-34-1 2,4-Bis-3-(2-cyanethyl)benzonitril 
• 110-94-1 1,5-pentanedioic acid 
• 39201-33-7 4-cyanobutyric acid 
• 31579-41-6 1,2,3,5,6,7-hexahydrodicyclopentapyrazine 
• 79058-64-3 Pentandial-bis(4-nitrophenylhydrazon) 
• 4802-79-3 1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizine 
• 1121-89-7 piperidine-2,6-dione 

Relevant academic research and scientific papers

A mineralogically-inspired silver-bismuth hybrid material: An efficient heterogeneous catalyst for the direct synthesis of nitriles from terminal alkynes

The synthesis and characterization of a silver-containing hybrid material is reported as a novel heterogeneous noble metal catalyst. In order to eliminate the need for traditional immobilization techniques, and to create a solid material with structurally-bound silver catalytic centers, the layered structure of a naturally occurring mineral served as the basis of the initial catalyst design. The novel material was prepared by means of the urea-mediated homogeneous precipitation of the corresponding metal nitrates, and was fully characterized by means of diverse instrumental techniques (X-ray diffractometry, Raman, IR, UV-Vis, EPR, X-ray photoelectron spectroscopies, thermal methods as well as atomic force, scanning and transmission electron microscopies). The as-prepared material exhibited outstanding activity in silver-catalyzed CC bond activation to yield organic nitriles directly from terminal alkynes with less environmental concerns as compared to the classical synthesis methods. The effects of the reaction time, the temperature, as well as the role of various solvents, nitrogen sources and additives were carefully scrutinized in order to achieve high-yielding and selective nitrile formation. The heterogeneous nature of the reaction was verified and the solid catalyst was recycled and reused numerous times without loss of its activity or degradation of its structure, thereby offering a sustainable synthetic methodology.

Direct synthesis of nitriles from aldehydes with hydroxylamine-O-sulfonic acid in acidic water

Herein is reported the selective transformation of aldehydes to nitriles in the presence of hydroxylamine-O-sulfonic acid (NH2OSO3H) as a source of the N atom and acidic water. The reaction works with high yields for a large array of aromatic and aliphatic aldehydes, as well as hindered aldehydes and conjugated aldehydes without purification. The reaction conditions are very mild and tolerate a wide array of functional groups. In principle, the reaction can be completed in vinegar.

Synthesis of Nitriles from Aldoximes and Primary Amides Using XtalFluor-E

The dehydration reaction of aldoximes and amides for the synthesis of nitriles using [Et2NSF2]BF4 (XtalFluor-E) is described. Overall, the reaction proceeds rapidly (normally 1 h) at room temperature in an environmentally benign solvent (EtOAc) with only a slight excess of the dehydrating agent (1.1 equiv). A broad scope of nitriles can be prepared, including chiral nonracemic ones. In addition, in a number of cases, further purification of the nitrile after the workup was not required.

Pheromones and analogs from Neozeleboria wasps and the orchids that seduce them: a versatile synthesis of 2,5-dialkylated 1,3-cyclohexanediones

Chiloglottone, a wasp pheromone and attractant of sexually deceptive Chiloglottis orchids, and several structural analogs were synthesized. The synthetic approach is facile, high yielding and versatile, enabling rapid divergence to generate dialkylated analogs of chiloglottone. The key transformation was an organocadmium-mediated desymmetrization of glutaric anhydride derivatives. This library of synthetic 2,5-dialkylated 1,3-cyclohexanediones may assist in future identification of natural products in further species.

Rhodococcus nitrile hydratase

The invention relates to a Rhodococcus polynucleotide cluster which contains nucleotide sequences which encode polypeptides having the activity of a nitrile hydratase, of an auxiliary protein P15K which activates this enzyme and of a cobalt transporter, to transformed microorganisms in which the nucleotide sequences encoding these proteins are present in increased quantity, and to the use of the transformed microorganisms for preparing amides from nitriles.

Synthesis of an Isotopically Isomeric Mixture of 1,4,6,8-Tetramethyl2>azulene and Its Thermal Reaction with Dimethyl Acetylenedicarboxylate

Sodium 2>cyclopentadienide in tetrahydrofuran (THF) has been prepared from the corresponding labelled 2>cyclopentadiene which was synthesized from 13CO2 and (chloromethyl)trimethylsilane (cf.Scheme 10) according to an established procedure.It could be shown that the acetate pyrolysis of cis-cyclopentane-1,2-diyl diacetate (cis-22) at 550 +/- 5 deg under reduced pressure (60 Torr) gives five times as much cyclopentadiene as trans-22.The reaction of sodium 2>cyclopentadienide with 2,4,6-trimethylpyrylium tetrafluoroborate in THF leads to the formation of the statistically expected 2:2:1 mixture of 4,6,8-trimethyl2>-, -2>-, and -2>azulene (20; cf.Scheme 7 and Fig. 1).Formylation and reduction of the 2:2:1 mixture 2>-20 results in the formation of a 1:1:1:1:1 mixture of 1,4,6,8-tetramethyl2>-, -2>-, -2>-, -2>-, and -2>azulene (5; cf.Scheme 8 and Fig. 2).The measured 2J(13C,13C) values of 2>-20 and 2>-5 are listed in Tables 1 and 2.Thermal reaction of the 1:1:1:1:1 mixture 2>-5 with the four-fold amound of dimethyl acetylenedicarboxylate (ADM) at 200 deg in tetralin (cf.Scheme 2) gave 5,6,8,10-tetramethyl-2>heptalene-1,2-dicarboxylate (2>-6a; 22percent), its double-bond-shifted (DBS) isomer 2>-6b (19percent), and the corresponding azulene-1,2-dicarboxylate 7 (18percent).The isotopically isomeric mixture of 2>-6a showed no 1J(13C,13C) at C(5) (cf.Fig. 3).This finding is in agreement with the fact that expected primary tricyclic intermediate 2>-8 exhibits at 200 deg in tetralin only cleavage of the C(1)-C(10) bond and formation of a C(7)-C(10) bond (cf.Schemes 6 and 9), but no cleavage of the C(1)-C(11) bond and formation of a C(7)-C(11)-bond.The limits of detection of the applied method is Y>/= 96percent for the observed process, i.e., 2>-5 + ADM -> 2>-8 -> 2>-9 -> 2>-6a (cf.Scheme 6).

Synthesis of 6-Substituted 2-(N-Acetylamino)pyridines and 2-Aminopyridines by Cyclization of 5-Oximinoalkanenitriles

Oxime derivatives of 5-oxoalkanenitriles (C6 chain or longer) were cyclized in most cases with a combination of AcCl and Ac2O, or Ac2O and HCl to 6-substituted 2-(N-acetylamino)pyridines.Alkaline hydrolysis gave the corresponding 2-aminopyridines in overall yields of 40-65 percent, with the exception of pyridine 3e.Oxime derivatives of 5-oxopentanenitriles did not cyclize but gave glutaronitriles instead.In some experiments with 5-oximinohexanenitrile (1a), 2,4-dimethyl-5-(2-cyanoethyl)oxazole (9) was detected in addition to the main product, 2-(N-acetylamino)-6-methylpyridine (2a).Formation of these compounds can be explained on the basis of a common intermediate 7 formed through rearrangement of the O-acetylated 5-oximinohexanenitrile (4).

ACCELERATION OF SOLID-LIQUID TWO-PHASE REACTION BY MEANS OF ALUMINA-WATER-ULTRASOUND. A SUBSTITUTE FOR A PHASE TRANSFER CATALYST

Combined use of alumina, a trace of water, and ultrasound greatly accelerated a solid-liquid two-phase nucleophilic substitution by cyanide ion in nonpolar organic solvents.The efficiency under the optimum conditions were compared with that of phase transfer catalysts such as 18-crown-6.

Cyanomethylation versus Reductive Saturation and Hydrodimerisation during the Electroreduction αβ-Unsaturated Nitriles in Acetonitriles

Results for the electroreduction of cinnamonitrile, 3-methylcinnamonitrile, and acrylonitrile in acetonitrile under a variety of conditions are reported in detail, and the factors which favour the formation of glutaronitrile derivatives (cyanomethylation) versus reductive saturation and hydrodimerization have been identified.Cyanomethylation of acrylonitrile has also been studied using (i) azobenzene-acetonitrile, and (ii) phenylsulphonylacetonitrile-dimethylformamide, as the source of electrogenerated -CH2CN.