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Benzonitrile

Manufactured by Merck Group
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Sourced in Germany, United States

Benzonitrile is a colorless, volatile liquid organic compound. It has the chemical formula C6H5CN. Benzonitrile is commonly used as a solvent and an intermediate in the synthesis of various chemical compounds.

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Lab products found in correlation

Acetonitrile, by Merck Group (4 mentions) 3 butenenitrile, by Merck Group (4 mentions) 3 phenylpropanenitrile, by Merck Group (4 mentions) 4 hydroxybenzyl gls, by Carl Roth (4 mentions) Methylene chloride gc ultra grade, by Carl Roth (3 mentions) 4 pentenenitrile, by Merck Group (3 mentions) Mandelonitrile, by Merck Group (3 mentions) Potassium chloride (kcl), by Merck Group (2 mentions) Chloroform, by Merck Group (2 mentions) Ethyl acetate, by Merck Group (2 mentions) Deae sephadex a 25, by Merck Group (2 mentions) Toluene, by Merck Group (2 mentions) 2 phenylethyl isothiocyanate, by Merck Group (2 mentions) 4 methylthio butyl itc 4 mtb itc, by Santa Cruz Biotechnology (2 mentions) Acetonitrile ultra gradient hplc grade, by Avantor (2 mentions) Cyclohexanol, by Merck Group (2 mentions) Chlorobenzene, by Merck Group (2 mentions) Succinonitrile, by Merck Group (2 mentions) 1 2 benzenedicarbonitrile, by Merck Group (2 mentions) Sodium cyanide, by Merck Group (2 mentions)

24 protocols using benzonitrile

1

Electrochemical Characterization of Porphyrin Derivatives

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The syntheses and full characterisation of Zn(II) 5,10,15,20-tetrakis(4-pyridyl)-porphyrin (ZnP) and Co(II) 5,10,15,20-tetrakis(3-hydroxyphenyl)-porphyrin (CoP) have been previously reported [26 ,34 (link)], and their chemical structures are presented in Scheme S1 from the Supplementary Material File.
The reagents used in the electrochemical study of the two porphyrin derivatives were dimethylsulfoxide (DMSO), acetonitrile (CH3CN), benzonitrile (PhCN), potassium hydroxide, potassium chloride, and sulphuric acid 98% purchased from Merck (Darmstadt, Germany); N,N-dimethylformamide (DMF), dichloromethane (DCM), tetrahydrofuran (THF), and potassium hexacyanoferrate(III) provided by Sigma Aldrich (Saint Louis, MO, USA); ethanol (EtOH) from Honeywell (Charlotte, NC, USA); and acetone from Chimreactiv (Bucharest, Romania). Laboratory-obtained-double-distilled water was employed to prepare all aqueous solutions. The conductive graphite used to manufacture the electrodes was type SW.114 spectroscopic graphite from “Kablo Bratislava”, National Corporation “Electrocarbon Topolcany” Factory (Bratislava, Slovakia).
Taranu B.O, & Fagadar-Cosma E. (2022). The pH Influence on the Water-Splitting Electrocatalytic Activity of Graphite Electrodes Modified with Symmetrically Substituted Metalloporphyrins. Nanomaterials, 12(21), 3788.
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2

Synthesis and Characterization of PPO Polymer Solutions

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Poly(propylene oxide) (PPO) and the utilized solvents were acquired from Sigma Aldrich (now Merck), St. Louis, MO, USA. The chemical structure of the polymer is displayed in Scheme 1.
The polymer solutions were prepared by dissolving 2.5 g of PPO powder in 100 mL of each of the following solvents, acquired from Sigma Aldrich (now Merck): benzonitrile (anhydrous, ≥99%), carbon disulfide (anhydrous, ≥99%), chloroform (anhydrous, ≥99%, contained 0.5–1.0% ethanol as a stabilizer), ethyl acetate (anhydrous, ≥99.8%), and p-dioxane (anhydrous, ≥99.8%). The pH of the polymer solutions did not vary intentionally during experiments, and the small variations were caused by the combination of PPO (pH = 4) with the selected solvents having pH values comprised between 4 and 7.
Zara A., Albu R.M., Stoica I., Barzic A.I., Dimitriu D.G, & Dorohoi D.O. (2024). New Insights on Solvent-Induced Changes in Refractivity and Specific Rotation of Poly(propylene oxide) Systems Extracted from Channeled Spectra. International Journal of Molecular Sciences, 25(9), 4682.
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3

Glucosinolate Analytical Methods

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Boric acid solution (4%), hydrochloric acid (0.1 M), hydrochloric acid (32%), formic acid (FA; 98%), sodium hydroxide (100%), trichloroacetic acid (≥99%), Kjeldahl tablets, sulfuric acid (96–98%, p.a.), methanol (LC-MS grade), water (LC-MS grade), methylene blue, methyl red and methylene chloride (GC Ultra Grade, solvent) were purchased from Carl Roth GmbH & Co. KG (Karlsruhe, Germany). Pronase E (from Streptomyces griseus), pepsin (from porcine gastric mucosa), pancreatin (from porcine pancreas), β-glucuronidase (from Helix pomatia), DEAE Sephadex® A-25, 4-hydroxybenzyl glucosinolate potassium salt, 2-propenyl glucosinolate potassium salt, benzyl cyanide (≥98%), benzonitrile (≥99.9%), and benzyl isothiocyanate (≥98.5%) were obtained from Merck KGaA (Darmstadt, Germany). 1H-Imidazole was purchased from AppliChem GmbH (Darmstadt, Germany), boric acid (powder, pure) from Honeywell International Inc. (Seelze, Germany) and 4-(methylsulfinyl)butyl glucosinolate from PhytoLab GmbH & Co. KG (Vestenbergsgreuth, Germany). Sodium sulfate anhydrous (≥99%) was obtained from VWR International GmbH (Darmstadt, Germany). C18ec solid phase extraction cartridges (3 mL, 200 mg) were obtained from Machery-Nagel GmbH & Co. KG (Düren, Germany). The BITC-lysine and BITC-cysteine standards used were synthesized by Kühn et al. [23 (link)].
Krell M., Cvancar L., Poloczek M., Hanschen F.S, & Rohn S. (2021). Determination of Isothiocyanate-Protein Conjugates in a Vegetable-Enriched Bread. Foods, 10(6), 1300.
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4

Open Microcavity Fabrication Protocol

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Methyl salicylate (99%), methylcyclohexane (99%), benzonitrile (99%), toluene (99%), and polyvinyl acetate (MW: 100 000) were purchased from Sigma-Aldrich and used without further purification. CaF 2 windows (diameter: 25.0 mm, thickness: 5.0 mm) were purchased from Crystran LTD, while a mirror mount with a piezoelectric adjuster and a voltage controller were purchased from Thorlabs, Inc.
Open microcavity preparation 54, 55 The Ag films, typically 10 nm thick (unless otherwise explicitly stated), were deposited on a CaF 2 substrate by a high vacuum sputter coater (Leica EM MED 020 coating system). The thickness of the metal film was controlled using a quartz microbalance film thickness monitoring system (EM QSG100) as a reference during sputtering. The microcavity was realized by bringing the Ag-coated CaF 2 windows in close proximity and by carefully controlling their parallelism with the kinematic mirror holders. Subsequently, the cavity was filled by adding a few droplets of an appropriate solution onto the edges of the CaF 2 windows using a micropipette. The solution flowed into the cavity by capillary action and remained stable between the mirrors during the entire experiment.
Takele WM ., Piatkowski L ., Wackenhut F ., Gawinkowski S ., Meixner AJ , & Waluk J . (2021). Scouting for strong light-matter coupling signatures in Raman spectra. Physical chemistry chemical physics : PCCP, 23(31).
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5

Characterization of Nitrogen Compounds in Fuels

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Dichloromethane,
hexane, pentadecane (C15), heptadecane (C17), N,N-diethylaniline (DEA, 99%), N,N-dibutylaniline (DBA, 99%), quinoleine (Q, 98%), 1-methylindole
(1MI, 97%), 2,6-diisopropylaniline (DPA, 100%), indole (I, 99%), 3-methylindole
(3MI, 98%), carbazole (C, 95%), 4-ethylpyridine (4EPy, 98%), diethylpropionamide
(DEPA, 99%), aniline (A, 99.5%), nitrobenzene (NBz, 99%), 1,2-dimethyl-3-nitrobenzene
(DMNBz, 97%), benzonitrile (BZN, 99.9%), caprylonitrilo (HpCN, 99%),
and caprolactame (CAP, 100%) (see Figure S1) were purchased from Sigma-Aldrich. The Certified Reference Material
D-4629-91-HB-CON, consisting of a nitrogen solution for high boiling
solvents containing carbazole (998 μg N g–1) in toluene/acetone (9:1), was acquired from AccuStandard. Helium
and the mixture of 0.3% (v/v) O2 in He were obtained from
Air Liquide and Linde AG, respectively. Real samples, diesel and biomass
pyrolysis oil, were provided by TotalEnergies Raffinage Chimie.
García-Bellido J., Freije-Carrelo L., Redondo-Velasco M., Piparo M., Zoccali M., Mondello L., Moldovan M., Bouyssiere B., Giusti P, & Encinar J.R. (2023). Potential of GC-Combustion-MS as a Powerful and Versatile Nitrogen-Selective Detector in Gas Chromatography. Analytical Chemistry, 95(31), 11761-11768.
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6

Isolation and Identification of Glucosinolates

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Indoline (99%), I3C (97%) and I3ACN (97%) were purchased from VWR International (Darmstadt, Germany), 4-methoxyindole (95%) from abcr GmbH (Karlsruhe, Germany), indole-3-carbonitrile (I3CN; 98%) from Alfa Aesar-Thermo Fisher Scientific (Dreieich, Germany) and benzonitrile (≥99%) from Sigma Aldrich (Taufkirchen, Germany). N-Methyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA) was purchased from Alfa Aesar-Thermo Fisher Scientific (Dreieich, Germany), and 1% trimethylchlorosilane (TMCS) in MSTFA was purchased from Sigma Aldrich (Taufkirchen, Germany). 4-Hydroxybenzyl glucosinolate (99%) was purified from seeds of Sinapis alba L. (Brassicaceae), and its identity was confirmed by HPLC-DAD in comparison with an authentic standard.
Chroston E.C., Hielscher A., Strieker M, & Wittstock U. (2022). The Impact of Nitrile-Specifier Proteins on Indolic Carbinol and Nitrile Formation in Homogenates of Arabidopsis thaliana. Molecules, 27(22), 8042.
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7

Glucosinolate and Isothiocyanate Compound Analysis

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2-propenyl glucosinolate hydrate (sinigrin, allyl-GLS, ≥ 99%), 2-propenyl isothiocyanate (allyl-ITC, ≥ 99%), benzonitrile (≥ 99.9%), 3-butenenitrile (allyl-CN, ≥ 98%), thioglucosidase (myrosinase) from Sinapis alba (white mustard) seed (EC 3.2.1.147), 2-phenylethyl isothiocyanate (2-phenylethyl-ITC, ≥ 99%), and 3-phenylpropanenitrile (2-phenylethyl-CN, ≥ 99%) were purchased from Sigma-Aldrich Chemie GmbH (Steinheim, Germany). 4-(Methylthio)butyl ITC (4-MTB-ITC; ≥ 98%) was purchased from Santa Cruz Biotechnology (Heidelberg, Germany); 1-cyano-2,3-epithiopropane (CETP, ≥ 95%) was purchased from Taros Chemicals GmbH & Co. KG (Dortmund, Germany); methylene chloride (GC Ultra Grade) from Carl Roth GmbH (Karlsruhe, Germany); acetonitrile (Ultra Gradient HPLC grade) from J.T. Baker (Deventer, The Netherlands); iron standard (1 g/L Fe, (FeCl3 in 15% HCl) Titrisol), HNO3 (65%, Suprapur) and H2O2 (30%, Suprapur) were purchased from Merck KGaA (Darmstadt, Germany). NaSO4 (≥ 99%) was purchased from VWR International GmbH (Darmstadt, Germany). Water was of Milli-Q quality.
Hanschen F.S., Yim B., Winkelmann T., Smalla K, & Schreiner M. (2015). Degradation of Biofumigant Isothiocyanates and Allyl Glucosinolate in Soil and Their Effects on the Microbial Community Composition. PLoS ONE, 10(7), e0132931.
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8

Analyzing Glucosinolate Breakdown Products

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For the determination of enzymatically formed breakdown products of the GLS in fresh plant tissues, benzonitrile (≥99.9%, Sigma-Aldrich Chemie GmbH) was added as an IST and catabolites were extracted with dichloromethane (Carl Roth GmbH; GC Ultra Grade) as described previously (Witzel et al., 2015 ). For the analysis of glucosinolate breakdown products in exudates, the total volume of each exudate (500ml) was extracted with 50ml of dichloromethane in a separating funnel. The separated dichloromethane layer was dried using anhydrous NaSO4 (VWR International GmbH, Darmstadt, Germany; ≥99%) and the aqueous phase was re-extracted twice using 25ml of dichloromethane. The combined dichloromethane extract was dried under nitrogen to 300 µl and subjected to GC-MS analysis as described above.
Xu D., Hanschen F.S., Witzel K., Nintemann S.J., Nour-Eldin H.H., Schreiner M, & Halkier B.A. (2016). Rhizosecretion of stele-synthesized glucosinolates and their catabolites requires GTR-mediated import in Arabidopsis. Journal of Experimental Botany, 68(12), 3205-3214.
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9

Preparation of Simulated Salivary Fluid

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Acetic acid (≥99.5%), 2Prop-GLS (≥99%), l-ascorbic acid (≥99%), benzonitrile (≥99.9%), d/l-dithiothreitol, FeSO4(H2O)7 (≥99%), myrosinase (thioglucosidase from Sinapis alba seeds; ≥100 units/g) and NaHCO3 (≥99.5%) were purchased from Sigma-Aldrich Chemie GmbH, (Steinheim, Germany). 4-Hydroxybenzyl GLS (≥99%) was purchased from Carl Roth GmbH, Karlsruhe, Germany and NaCH3COO(H2O)3 (≥99.5%) was purchased from Merck (Darmstadt, Germany), respectively. Simulated salivary fluid (saliva buffer) was prepared according to60 (link) (pH 7) using chemicals from Merck (Darmstadt, Germany) (KCl, KH2PO4, MgCl2(H2O)6, CaCl2(H2O)2) and Sigma-Aldrich Chemie GmbH, (Steinheim, Germany) (α-amylase. NaHCO3, HCl (37%), (NH4)2CO3 (≥30%, NH3 basis)) with a purity of ≥99% if not stated otherwise. All solvents were of LC-MS grade and water was of Milli-Q quality.
Hanschen F.S., Klopsch R., Oliviero T., Schreiner M., Verkerk R, & Dekker M. (2017). Optimizing isothiocyanate formation during enzymatic glucosinolate breakdown by adjusting pH value, temperature and dilution in Brassica vegetables and Arabidopsis thaliana. Scientific Reports, 7, 40807.
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10

Synthesis and Characterization of Functional Polymers

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Multiwalled carbon nanotubes were purchased from Sun Innovation Inc. (Fremont, CA, USA). Alkylbenzenes, phenoxy acid herbicides, cyanobenzene derivatives, benzonitrile, aniline derivatives, trifluoroacetic acid (TFA), 2,2′-azobis(isobutyronitrile) (AIBN), octadecyl acrylate (ODA), butyl methacrylate (BMA), trimethylolpropane trimethacrylate (TRIM), ethylene glycol dimethacrylate (EDMA), ethylene glycol, methyl methacrylate (MMA), chlorophenols, 1-dodecanol, cyclohexanol, DL-dansyl (Dns) amino acids, were purchased from Sigma Aldrich (Milwaukee, WI, USA). Glyceryl monomethacrylate (GMM) was from Monomer-Polymer and Dajac Labs (Trevose, PA, USA). Egg white lysozyme, bovine serum albumin, ribonuclease A, ovalbumin, horse heart cytochrome C, bovine erythrocytes carbonic anhydrase, bovine milk β–lactoglobulin A and B and bovine milk α-lactalbumin were purchased from Sigma (St. Louis, MO, USA). HPLC grade acetonitrile and isopropyl alcohol were purchased from Pharmco Aaper (Brookfield, CT, USA). Stainless steel tubing of 4.6 mm id was obtained from Alltech Associates (Deerfield, IL, USA).
Mayadunne E, & Rassi Z.E. (2014). Facile Preparation of Octadecyl Monoliths with Incorporated Carbon Nanotubes and Neutral Monoliths with Coated Carbon Nanotubes Stationary Phases for HPLC of Small and Large Molecules by Hydrophobic and π-π Interactions. Talanta, 0, 565-574.
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