Benzonitrile

Benzonitrile structural formula

CAS Number 100-47-0
Molecular Formula C7H5N
Molecular Weight 103.125 g/mol
InChI Key JFDZBHWFFUWGJE-UHFFFAOYSA-N
LogP 1.56
Synonyms
  • Benzonitrile
  • 100-47-0
  • Benzene, cyano-
  • Benzenecarbonitrile
  • Benzenenitrile
  • Benzoic acid nitrile
  • Benzonitril
  • benzonitrilo
  • Cyanobenzene
  • NSC 8039
  • Phenyl cyanide
  • UN 2224
  • EINECS 202-855-7
  • Phenylcyanide
  • Fenylkyanid
  • UNII-9V9APP5H5S
  • C6H5-CN

Applications:


Complex Mixture of Acids, Bases, Amino Acids, and Neutral Compounds
Primesep 100 separates a mixture of amino acids (tyrosine, phenylalanine), organic acids (benzoic acid, mandelic acid), amines (benzylamine, pyridine), and neutrals (benzonitrile, toluene) in one HPLC run by combining reversed-phase, cation-exchange, and polar interactions. The method is tunable and peak order can be changed significantly by adjusting acetonitrile and trifluoroacetic acid concentrations. The separation method uses a mobile phase mixture of water, acetonitrile (MeCN, ACN) and trifluoracetic acid (TFA) and compatible with UV, mass spec (LC/MS) and evaporative light scattering (ELSD) detection.

Condition

Column Primesep 100, 4.6x250 mm, 5 µm, 100A
Mobile Phase MeCN/H2O - 30/70%
Buffer TFA - 0.2
Flow Rate 1.0 ml/min
Detection UV, 210 nm
 

Description

Class of Compounds Drug, Acid, Hydrophilic, Ionizable, Vitamin, Supplements, Amino acid
Analyzing Compounds Tyrosine, phenylalanine, Benzoic acid, mandelic acid, Benzylamine, Pyridine, Benzonitrile, Toluene
 

Application Analytes:

Amino Acids
Benzoic Acid
Benzonitrile
Benzylamine
Mandelic Acid
Organic Acids
Phenylalanine
Pyridine
Toluene
Tyrosine

Neutral, Base, and Acid on Primesep A Column



Primesep A separates acids, bases, and neutrals in one injection. Maleic acid, benzonitrile, and benzylamine are baseline resolved by a combination of reversed-phase, ion-exchange, and ion-exclusion mechanisms. Excellent peak shape results with a mass spec compatible mobile phase of water, acetonitrile (MeCN, ACN) and trifluoracetic acid (TFA) with UV detection at 210 nm.



Application Analytes:

Benzonitrile
Benzylamine
Maleic Acid

Neutral, Base, and Acid on Primesep 100 Column



Primesep 100 retains and separates an acid, base, and neutral in one HPLC injection. Maleic acid, benzylamine, and benzonitrile are resolved by ion-exclusion, ion-exhange and reversed-phase modes. The separation uses a mobile phase of water, acetonitrile (MeCN, ACN) and trifluoracetic acid (TFA) with UV detection at 210 nm.



Application Analytes:

Benzonitrile
Benzylamine
Maleic Acid

Neutral, Base, and Acid on Primesep 200 Column



Primesep 200 separates acids, bases, and neutrals in one injection. Maleic acid, benzonitrile, and benzylamine are baseline resolved by a combination of reversed-phase, ion-exchange, and ion-exclusion mechanisms. Excellent peak shape results with a mass spec compatible mobile phase of water, acetonitrile (MeCN, ACN) and trifluoracetic acid (TFA) with UV detection at 210 nm.



Application Analytes:

Benzonitrile
Benzylamine
Maleic Acid

Neutral, Base, and Acid on Primesep B Column



Primesep B separates acids, bases, and neutrals in one injection. Maleic acid, benzonitrile, and benzylamine are baseline resolved by a combination of reversed-phase, ion-exchange, and ion-exclusion mechanisms. Excellent peak shape results with a mass spec compatible mobile phase of water, acetonitrile (MeCN, ACN) and trifluoracetic acid (TFA) with UV detection at 210 nm.



Application Analytes:

Benzonitrile
Benzylamine
Maleic Acid

Acid Effect on Retention of Acidic Analytes

 

In mixed-mode chromatography, retention time and elution order can be changed for acidic analytes based on the pH of the mobile phase. In this application, the order of elution for benzoic acid and benzonitrile is changed by changing the pH of the mobile phase. At lower pH (pH-2, TFA), ionization of carboxylic acid fragment of benzoic acid is totally suppressed (not ionized), and benzoic acid does not show any anion-exchange properties. As the pH of the mobile phase increases (pH 4, formic acid), the carboxylic acid fragment of benzoic acid is ionized and participates in ion-exchange interaction with positively charged sites of the mixed-mode column. In most cases, changing pH does not change retention of neutral analytes. Mixed-mode chromatography is compatible with all detection techniques (UV, ELSD, CAD, LC/MS, etc.)


Application Analytes:

Benzoic Acid
Benzonitrile

Effect of mobile phase composition on retention of 3 compounds on Obelisc R
This application shows the effect of mobile phase composition on retention of acidic, basic and neutral compound. Retention of basic and acidic compounds is controlled by buffer pH and concentration, while retention of neutral compound is controlled by the amount of acetonitrile. Buffer pH changes not only ionization state of ionizable basic and acidic compounds, but ionization state of trimodal stationary phase Obelisc R. Available detection techniques include UV, ELSD, LC/MS, and Corona.

Condition

Column Obelisc R, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer AmAc
Flow Rate 1.0 ml/min
Detection 250
 

Description

Class of Compounds Acid, Hydrophilic, Neutral, BasicIonizable
Analyzing Compounds Benzonitrile, Benzoic Acid, Benzylamine
 

Application Analytes:

Benzoic Acid
Benzonitrile
Benzylamine

HPLC Separation of Amino Acids, Bases, Acids, and Neutrals on Obelisc R
Separating basic, acidic and zwitterionic compounds in one run in reverse-phase HPLC can be very challenging. The methods might require the use of ion-pairing reagents and complex gradients that can make MS-compatibility difficult. Obelisc R column which has both positive and negative ion-pairs embedded in the stationary phase allows for fine tuning and separation of a wide range of compounds with different ionic properties. Acids, bases, amino acids and neutral compounds were separated isocratically in one run using a simple MS-compatible mobile phase of acetonitrile (ACN) and water with Ammonium Acetate (AmAc) buffer. Can also be UV detected at 250nm.

Condition

Column Obelisc R, 4.6x250 mm, 5 µm, 100A
Mobile Phase MeCN/H2O - 35/65%
Buffer AmAc 10 mM pH 4.0
Flow Rate 1.0 ml/min
Detection UV, 250 nm
 

Description

Class of Compounds Drug, Acid, Bases, Neutral, Hydrophilic, Ionizable, Vitamin, Supplements, Amino acid
Analyzing Compounds Amino acids
 

Application Analytes:

2,6-Lutidine
Benzoic Acid
Benzonitrile
Benzylamine
Phenol
Phenylalanine
Pyridine
Toluene
Tryptophan

HPLC Separation of Methyl Paraben, Benzonitrile, Propyl Paraben, and Toluene on Mixed-Mode and Reverse Phase Columns
Parabens are common preservatives in pharmaceutical and cosmetic industries. They are esters of p-hydroxybenzoic acid. Method for separation of methyl paraben, propyl paraben, benzonitrile and toluene was developed on a Obelisc R column. All four compounds are neutral and are retained by reverse-phase mechanism. In case of reversed-phase stationary phase, no effect of pH is observed. Retention time for all four compounds changes on an Obelisc R column when pH is changed. pH of the mobile phase affects ionization state of stationary phase. Obelisc R column has C12 carbon chain and carboxylic acid with pKa of 4. At lower pH (pH 2, TFA), carboxylic acid of stationary phase is not ionized and thus adds hydrophobicity to stationary phase. Obelisc R column can be used for analysis of basic, acidic and neutral compounds with suitable detection techniques - UV, ELSD, CAD, LC/MS.

Condition

Column Obelisc R, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer AmAc, TFA
Flow Rate 1.0 ml/min
Detection UV, 270 nm
 

Description

Class of Compounds Preservatives, Neutral
Analyzing Compounds Methyl paraben, Benzonitrile, Propyl paraben, Toluene
 

Application Analytes:

Benzonitrile
Methylparaben
Propylparaben
Toluene

HPLC Separation of Dequalinium and Benzonitrile on Different Columns
Dequalinium, or Dequadin, is an antiseptic and disinfectant. It consists of two quaternary amines connected by C10 hydrophobic chain. It's a strongly basic compound that is hard to analyze on reverse phase column and obtain good peak shape. Compound shows a significant tailing (symmetry below 0.5 and USP tailing factor of over 2) due to interaction of quaternary groups with residual silanols. In this HPLC application dequalinium is analyzed on Primesep D mixed-mode column with perfect symmetry and high efficiency. Primesep D column has hydrophobic chain and a basic group close to the surface of silica gel. This group provides shielding effect and prevents interaction between acidic silanol groups and quaternary amines of dequalinium. Method can be used for analysis and quantitation of hydrophobic amines when peak shape is not satisfactory on traditional HPLC columns. Relative comparison of several modern LC columns (Zorbax from Agilent, XTerra from Waters and Gemini from Phenomenex) shows that Primesep D mixed-mode column can be successfully used in determination of hydrophobic quaternary amines and diamines. If a compound is retained on C18 column with poor peak shape, switching to mixed-mode column can provide a valuable alternative. Benzonitrile is used to ensure high quality of packing and good peak shape for neutral analytes. Method uses trifluoroacetic acid as an additive to the mobile phase. Other acids and buffers can be used depending on the detection technique.

Condition

Column Primesep D, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer TFA
Flow Rate
Detection UV, 240 nm
 

Description

Class of Compounds Quaternary amines
Analyzing Compounds Dequalinium,  Benzonitrile
 

Application Analytes:

Benzonitrile
Dequalinium

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