24057-28-1

Basic information

• Product Name: Pyridinium p-toluenesulfonate
• Synonyms: 4-TOLUENESULFONIC ACID PYRIDINE SALT;PPT;PPTS;POLY(4-VINYLPYRIDINIUM (TOLUENE-4-SULFONATE));PYRIDINIUM 4-TOLUENESULFONATE;PYRIDINE P-TOLUENESULFONATE;PYRIDINIUM P-TOLUENESULFONATE;PYRIDINIUM P-TOLUENESULPHONATE
• CAS NO: 24057-28-1
• Molecular Formula: C₅H₆N*C₇H₇O₃S
• Molecular Weight: 251.3
• EINECS: 246-002-7
• Product Categories: Pyridinium Compounds;Building Blocks;C12;Chemical Synthesis;Heterocyclic Building Blocks;Organic Acids;Pyridines;Synthetic Reagents;Heterocyclic Acids
• Mol File: 24057-28-1.mol

Chemical Properties

• Melting Point: 117-120 °C
• Boiling Point: 442.7 °C at 760 mmHg
• Flash Point: 221.6 °C
• Appearance: White to light beige/Crystalline Powder or Crystals
• Density: 1.2829 (rough estimate)
• Vapor Pressure: 1.29E-08mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• Water Solubility: decomposes
• Sensitive: Moisture Sensitive
• BRN: 3764305
• CAS DataBase Reference: Pyridinium p-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridinium p-toluenesulfonate(24057-28-1)
• EPA Substance Registry System: Pyridinium p-toluenesulfonate(24057-28-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 9-21
• TSCA: Yes
• Hazardous Substances Data: 24057-28-1(Hazardous Substances Data)

Usage

Uses

1. As a co-catalyst in asymmetric aldol condensation:
Pyridinium p-toluenesulfonate is used as a co-catalyst with L-proline to improve both the yield and enantioselectivity of an asymmetric aldol condensation between dioxanones and aldehydes. This application enhances the efficiency and selectivity of the reaction, leading to better product quality.
2. In the pharmaceutical industry:
Used in the pharmaceutical industry, Pyridinium p-toluenesulfonate is employed in the synthesis of a subdomain of the cytochrome P450 BM3 enzyme. This enzyme subdomain is utilized in screening systems for drug candidates, playing a crucial role in the development and evaluation of new medications.
3. In the synthesis of enzyme subdomains for drug screening:
Pyridinium p-toluenesulfonate is used as a key component in the synthesis of specific enzyme subdomains, which are then used in screening systems for drug candidates. This application is vital for identifying potential drug molecules and assessing their effectiveness and safety before they proceed to further stages of development.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C7H8O3S.C5H5N/c1-6-2-4-7(5-3-6)11(8,9)10;1-2-4-6-5-3-1/h2-5H,1H3,(H,8,9,10);1-5H

Upstream product

• 110-86-1 pyridine 
• 104-15-4 toluene-4-sulfonic acid 
• 80-48-8 methyl p-toluene sulfonate 

Downstream Products

• 99902-26-8 (2R,6R)-6-methyl-2-(2'-phenylethyl)-1,3-dioxan-4-on 
• 2668-74-8 17-acetoxy-pregna-1,4-diene-3,20-dione 
• 89929-99-7 6-nitro-2-(2-tetrahydropyranyloxy)methyltoluene 
• 104343-64-8 1-Benzyloxy-2-(2-tetrahydropyranyl)oxy-3-[(4-ethoxycarbonyl)phenoxy]propane 
• 101335-75-5 N-Hydroxy-N-methyl-4-(4-phenyl-1-butenyl)benzamide 
• 128156-58-1 methyl 2-(4-methoxyphenyl)-4-benzoxazolecarboxylate 
• 128156-60-5 methyl 2-(4-nitrophenyl)-4-benzoxazolecarboxylate 
• 179476-89-2 6-(4-chlorophenyl)-4-(2-hydroxy-3-phenylpropyl)-1-methyl-4H-2,3,4,5,10b-pentaazabenz[e]azulene 
• 103-50-4 dibenzyl ether 
• 36603-49-3 4-(tetrahydropyran-2'-yloxy)-1-bromobenzene 
• 73204-07-6 4-(4-cyanophenyl)cyclohexanone 

Relevant articles and documents

Efficient synthesis, X-ray diffraction study and antimicrobial activity of some novel thiazolidin-4-ones and perhydro-1,3-thiazin-4-ones

Condensations of thiosemicarbazones 1 derived from 1-tetralones with chloroacetic acid and 2-bromopropionic acid in the presence of N -methylpyridinium p -toluenesulfonate (an ionic liquid) yield the corresponding 2-substituted 4-thiazolidinones 2. The re

Method for preparing (S)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propionamide and salts thereof

The invention relates to a method for preparing (S)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propionamide and salts thereof. Salts of (S)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propionamide mean (S)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propionamide mesylates. The preparation method comprises the step of preparing the target product through synthesizing novel compounds, i.e., 2-(3-bromo-4((3-fluorobenzyl)oxy)phenyl)-1,3-dioxolane and 2-((3-fluorobenzyl)oxy)-5-formyl phenylboronic acid and belongs to bran-new preparation methods. The yield of the (S)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propionamide prepared by the preparation method is 49.57%, and the HPLC purity reaches 78.92%, and the yield of the salts of the prepared (S)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propionamide is 50.40%, and the HPLC purity reaches 96.35%, so that the yield and the HPLC purity are improved greatly compared with those in the prior art.

Preparation method of 3-(3-luorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde

The invention relates to a preparation method of 3-(3-luorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde. The preparation method comprises the following steps: respectively preparing 3-bromo-4-[(3-fluorobenzyl)oxy]benzaldehyde and pyridinium p-toluenesulfonate, letting 3-bromo-4-[(3-fluorobenzyl)oxy]benzaldehyde react with pyridinium p-toluenesulfonate to generate 2-(3-bromo-4-((3-fluorobenzyl)oxy)phenyl)-1,3-dioxolame, hydroxylating 2-(3-bromo-4-((3-fluorobenzyl)oxy)phenyl)-1,3-dioxolame to obtain 2-((3-fluorobenzyl)oxy)-5-formylphenylboronic acid, and finally coupling 2-((3-fluorobenzyl)oxy)-5-formylphenylboronic acid and m-fluorobenzyl bromide to obtain the target product. The invention provides a method for directly preparing 3-(3-luorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde. By the method, yield of the 3-(3-luorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde reaches up to 64.85%, and purity measured by high performance liquid chromatography reaches 98.92%.

2-(3-bromine-4-(3-fluorobenzyloxy)phenyl)-1,3-dioxolame and preparation method thereof

The invention relates to a new compound 2-(3-bromine-4-(3-fluorobenzyloxy) phenyl)-1,3-dioxolame and a preparation method thereof. The preparation method includes: respectively preparing 3-bromine-4-(3-fluorobenzyloxy) benzaldehyde and 4-methyl benzenesulfonic acid pyridinium first, and allowing the 3-bromine-4-(3-fluorobenzyloxy) benzaldehyde to have reaction with the 4-methyl benzenesulfonic acid pyridinium to generate the 2-(3-bromine-4-(3-fluorobenzyloxy) phenyl)-1,3-dioxolame. The 2-(3-bromine-4-(3-fluorobenzyloxy) phenyl)-1,3-dioxolame prepared by the method can be directly used for preparing 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy) benzaldehyde, the yield of the prepared 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy) benzaldehyde reaches up to 64.85%, and the purity, measured by high performance liquid chromatography, of the 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy) benzaldehyde reaches 98.92%.

2-(3-fluorobenzyloxy)-5-formylphenylboronic acid and preparation method thereof

The invention relates to a novel compound, i.e., 2-(3-fluorobenzyloxy)-5-formylphenylboronic acid and a preparation method thereof. The method comprises the steps of firstly, separately preparing 3-bromo-4-[(3-fluorobenzyl)oxy]phenylaldehyde (represented by a formula 3) and 4-toluenesulfonic acid pyridinium (represented by a formula 6), then, enabling the compound represented by the formula 3 and the compound represented by the formula 6 to react so as to produce 2-(3-bromo-4-(3-fluorobenzyloxy)phenyl)-1,3-dioxolane (represented by a formula 7), and enabling the compound represented by the formula 7 to make a coupling reaction, thereby obtaining 2-(3-fluorobenzyloxy)-5-formylphenylboronic acid (represented by a formula 8). The novel compound, i.e., 2-(3-fluorobenzyloxy)-5-formylphenylboronic acid provided by the invention can be used for preparing 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)phenylaldehyde, the yield of the prepared 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)phenylaldehyde reaches 64.85%, and the purity measured through high-performance liquid chromatography at least reaches 98.92%.

Esterification catalysis by pyridinium p -toluenesulfonate revisited - Modification with a lipid chain for improved activities and selectivities

The lipid analogs of pyridinium p-toluenesulfonate (PPTS) were examined for catalysis of the condensation of an equimolar mixture of carboxylic acids and alcohols under mild conditions without removal of water. Although PPTS is a poor catalyst, the introduction of a lipid chain and nitro group significantly improved the activity of PPTS and led to selectivity at suppressing the elimination side reactions of alcohols. 2-Oleamido-5-nitro-pyridinium p-toluenesulfonate (6) is a lead catalyst that promoted various esterification reactions with yields up to 99%.

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