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Cas Database

104-15-4

104-15-4

Identification

  • Product Name:p-Toluenesulfonic acid

  • CAS Number: 104-15-4

  • EINECS:203-180-0

  • Molecular Weight:172.205

  • Molecular Formula: C7H8O3S

  • HS Code:2904.90

  • Mol File:104-15-4.mol

Synonyms:P-Toluene sulfonic acid monohydrate;2-Toluene Sulfonic Acid;4-Toluene sulfonic acid;P-Toluosulfonic Acid Monohydrate;Methylbenzenesulfonic acid;Toluene-p-sulfonate;4-methylbenzenesulfonic acid;Cyzac 4040;4-Toluenesulfonic acid;Cyclophil P T S A;Benzenesulfonic acid, methyl-;p-toluene sulfonic acid;Toluene-4-sulfonic acid;ar-Toluenesulfonic acid;Kyselina p-toluenesulfonova;p-Toluene-sulfonic acid;Toluene-4-sulfonate;Benzenesulfonic acid, 4-methyl-;Benzenesulfonic acid,4-methyl-;Eltesol;p-Tolylsulfonic acid;p-Methylbenzene sulfonic acid;toluene-4-sulphonic acid;o-toluenesulfonic Acid;

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Safety information and MSDS view more

  • Pictogram(s):CorrosiveC

  • Hazard Codes:C

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Labseeker
  • Product Description:p-Toluenesulfonic acid monohydrate 98
  • Packaging:500g
  • Price:$ 133
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:p-Toluenesulfonicacid,12wt.%solutioninaceticacid
  • Packaging:1000g
  • Price:$ 221
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:p-Toluenesulfonicacid,12wt.%solutioninaceticacid
  • Packaging:250g
  • Price:$ 146
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Relevant articles and documentsAll total 186 Articles be found

The mechanisms of acid-catalyzed hydrolysis of n-(4-substituted arylthio) phthalimides

Kutuk, Halil,Yakan, Hasan

, p. 1460 - 1469 (2011)

The acid-catalyzed hydrolysis of N-(4-substitutedarylthio)phthalimides was studied in aqueous solutions of sulfuric, perchloric, and hydrochloric acids at 40.0 ±0.1° C. Analysis of the data by the excess acidity method, activation parameters, and substituent effects indicates hydrolysis by an A-2 mechanism at low acidity. At higher acidities, a changeover to an A-1 mechanism is observed.

Effect of Amine Nature on Reaction Rate and Mechanism in Nucleophilic Substitution Reactions of 2,4-Dinitrophenyl X-Substituted Benzenesulfonates with Alicyclic Secondary Amines

Um, Ik-Hwan,Chun, Sun-Mee,Chae, Ok-Mi,Fujio, Mizue,Tsuno, Yuho

, p. 3166 - 3172 (2004)

Second-order rate constants have been measured for reactions of 2,4-dinitrophenyl X-substituted benzenesulfonates with a series of alicyclic secondary amines. The reaction proceeds through S-O and C-O bond fission pathways competitively. The S-O bond fission occurs more dominantly as the amine basicity increases and the substituent X in the sulfonyl moiety becomes more strongly electron withdrawing, indicating that the regioselectivity is governed by the amine basicity as well as the electronic nature of the substituent X. The S-O bond fission proceeds through an addition intermediate with a change in the rate-determining step at pKa° = 9.1. The secondary amines are more reactive than primary amines of similar basicity for the S-O bond fission. The k1 value has been determined to be larger for reactions with secondary amines than with primary amines of similar basicity, which fully accounts for their higher reactivity. The second-order rate constants for the S-O bond fission result in linear Yukawa-Tsuno plots while those for the C-O bond fission exhibit poor correlation with the electronic nature of the substituent X. The distance effect and the nature of reaction mechanism have been suggested to be responsible for the poor correlation for the C-O bond fission pathway.

Evidence for complexes of different stoichiometries between organic solvents and cyclodextrins

Garcia-Rio,Herves,Leis,Mejuto,Perez-Juste,Rodriguez-Dafonte

, p. 1038 - 1048 (2006)

The influence of the organic solvent on the acid and basic hydrolysis of N-methyl-N-nitroso-p-toluenesulfonamide (MNTS) in the presence of α- and β-cyclodextrins has been studied. The observed rate constant was found to decrease through the formation of an unreactive complex between MNTS and the cyclodextrins. In the presence of dioxane, acetonitrile or DMSO, the inhibitory effect of β-CD decreased on increasing the proportion of organic cosolvent as a result of a competitive reaction involving the formation of an inclusion complex between β-CD and the cosolvent. The disparate size of the organic solvent molecules resulted in stoichiometric differences between the complexes; the β-CD-dioxane and β-CD-DMSO complexes were 1: 1 whereas the β-CD-acetonitrile complex was 1: 2. The basic and acid hydrolysis of MNTS in the presence of α-CD showed a different behavior; thus, the reaction gave both 1: 1 and 2: 1 α-CD-MNTS complexes, of which only the former was reactive. This result was due to the smaller cavity size of α-CD and the consequent decreased penetration of MNTS into the cavity in comparison to β-CD. The acid hydrolysis of MNTS in the presence of α-CD also revealed decreased penetration of MNTS into the cyclodextrin cavity, as evidenced by the bound substrate undergoing acid hydrolysis. In addition, the acid hydrolysis of MNTS in the presence of acetonitrile containing α-CD gave 1: 1 α-CD-acetonitrile inclusion complexes, which is consistent with a both a reduced cavity size and previously reported data. The Royal Society of Chemistry 2006.

Removal of electrophilic potential genotoxic impurities using nucleophilic reactive resins

Lee, Claire,Helmy, Roy,Strulson, Christopher,Plewa, Jolanta,Kolodziej, Elizabeth,Antonucci, Vincent,Mao, Bing,Welch, Christopher J.,Ge, Zhihong,Al-Sayah, Mohammad A.

, p. 1021 - 1026 (2010)

Potential genotoxic impurities (PGI) are chemical compounds that could potentially damage DNA and lead to mutation. Controlling the occurrence of PGIs in active pharmaceutical ingredients (APIs) poses a big challenge for chemists, as levels of these compounds must be reduced well below the amounts required for other types of less toxic impurities. In situations where formation of PGIs cannot be avoided, an ideal solution would allow the complete removal of PGIs after the synthesis is complete, for example, by recrystallization, preparative chromatography or other downstream processing approaches. Some disadvantages of using these approaches are potential high yield loss, high solvent consumption, and additional time and resources required for process development. In this work, we present a simple and rapid approach to remove electrophilic PGIs from APIs. A selected nucleophilic resin can be added to the final API solution to reduce or totally remove the PGI. Esters of methanesulfonic acid (MSA), benzenesulfonic acid (BSA), and ρ-toluenesulfonic acid (pTSA) were used as model electrophilic PGIs. Several nucleophilic resins were screened, and the resins with the highest efficiency of PGI removal were chosen. A recommended procedure is presented for the removal of MSA, BSA, and pTSA esters. The kinetics of PGI removal, resin loading capacity, solvent effects, and API matrix effects are demonstrated.

ESR study of free radical decomposition of N,N-bis(arylsulfonyl)hydroxylamines in organic solution

Balakirev, Maxim Yu.,Khramtsov, Valery V.

, p. 7263 - 7269 (1996)

Decomposition of N,N-bis(p-tolylsulfonyl)hydroxylamine (BTH) in chloroform and benzene solutions has been studied and was found to involve the formation of several radical intermediates. This process has been found to be accelerated by oxygen, resulting in the formation of p-toluenesulfonic acid and N,N,O-tris(p-tolylsulfonyl)hydroxylamine (TTH) as the main decay products. In addition, a small amount of p-toluenesulfonyl chloride has been isolated from chloroform solution, suggesting the chlorine abstraction from solvent. The formation of nitric oxide (NO) from BTH has been shown by mass spectrometry in gaseous phase and using nitronyl nitroxide as an NO trap in solution. It was proposed that liberation of NO proceeds through the homolytic cleavage of the S-N bond of p-tolylsulfonyl nitrite existing in equilibrium with BTH in solution. The formation of p-tolylsulfonyl radicals has been proved by spin trapping using 2-methyl-2-nitrosopropane (MNP) and 5,5-dimethyl-1-pyrroline N-oxide (DMPO). The rate of NO production in the presence of nitronyl nitroxide and the rate of oxygen consumption revealed linear plots in BTH concentration with the rate constants 0.0044 s-1 and 0.0016 s-1, respectively. It was found also that nitrogen dioxide formed during NO oxidation reacts readily with BTH to produce the organic analog of Fremy's radical. This radical recombines with p-tolylsulfonyl radical yielding N,N,O-trisubstituted hydroxylamine TTH.

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Hisada et al.

, p. 2814 (1972)

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Investigation of micellar media containing ?2-cyclodextrins by means of reaction kinetics: Basic hydrolysis of N-methyl-N-nitroso-p-toluenesulfonamide

Garciì?a-Riì?o,Leis,Mejuto,Peì?rez-Juste

, p. 7383 - 7389 (1997)

The kinetics of the basic hydrolysis of N-methyl-N-nitroso-p-toluenesulfonamide were studied in media containing sodium dodecyl sulfate (SDS) or tetradecyltrimethylammonium bromide (TTABr) micelles and ?2-cyclodextrin (CD). Under the experimental conditions, [NaOH] = 0.17 M, all CD will have been deprotonated; thus, binding constants apply to the CD anion. The results have been interpreted in terms of a pseudophase model that takes into account the formation of both CD - surfactant and CD - substrate complexes and also, for TTABr systems, the exchange of Br- and OH- ions between the micellar and aqueous pseudophases. The presence of CD has no effect on existing SDS or TTABr micelles but raises the cmc: complexation of surfactant by cyclodextrin makes the cmc dependent on CD concentration because the cmc is now the sum of the concentrations of free and complexed surfactant when micelles begin to form; increasing [CD] reduces the former quantity but increases the latter to a greater extent. At surfactant concentrations above the cmc, competition between the micellization and complexation processes leads to the existence of a significant concentration of free cyclodextrin.

Hydrogenolysis of 2-tosyloxy-1,3-propanediol into 1,3-propanediol over Raney Ni catalyst

Zheng, Zhi,Wang, Jianli,Lu, Zhen,Luo, Min,Zhang, Miao,Xu, Lixin,Ji, Jianbing

, p. 385 - 391 (2013)

2-Tosyloxy-1,3-propanediol (TPD), a potential precursor for 1,3-propanediol (1,3-PD) production, is produced by the tosylation of glycerol with the help of protecting group techniques. In this work, the hydrogenolysis of TPD into 1,3-PD over Raney Ni catalyst is discussed at different reaction parameters to optimize the reaction conditions for selective formation of 1,3-PD. The mechanisms of the hydrogenolysis of TPD and the side reactions were also confirmed by gas chromatography-mass spectrometry (GC-MS) technique.

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Lee et al.

, p. 206,212 (1959)

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The quest for sulfoquinone imine intermediates in the reaction of sulfanilic acid derivatives with nucleophiles

Thea, Sergio,Vigo, Daniele,Cevasco, Giorgio

, p. 611 - 614 (2002)

Data from kinetic and trapping studies suggest that the alkaline hydrolyses of sulfanilyl chloride and of the corresponding N-acetyl derivative follow different reaction pathways. While results for the latter compound are fully consistent with the occurrence of the common associative, SN2 mechanism, the former shows somewhat different features suggesting the incursion of a mechanism of the dissociative type involving a sulfoquinone imine species as a reaction intermediate. The alkaline hydrolyses of the corresponding sulfonyl fluorides and 2,4-dinitrophenyl esters, whose leaving groups are worse than Cl- as leaving groups, are all associative.

Influence of colloid suspensions of humic acids on the alkaline hydrolysis of N-methyl-N-nitroso-p-toluene sulfonamide

Astray,Garcia-Rio,Lodeiro,Mejuto,Moldes,Morales,Moyano

, p. 316 - 322 (2010)

The influence of humic substances (HSs) upon the alkaline hydrolysis of N-methyl-N-nitroso-p-toluene sulfonamide has been studied. Important inhibition of hydrolysis reaction has been reported. This inhibition has been explained in terms of association of reactants to the humic substances. Kinetic results have been modeled using the micellar pseudophase model.

General, fast, and high yield oxidation of thiols and disulfides to sulfonic and sulfinic acids using HOF·CH3CN

Shefer, Neta,Carmeli, Mira,Rozen, Shlomo

, p. 8178 - 8181 (2007)

Thiols and disulfides are oxidized to the corresponding sulfonic and sulfinic acids using HOF·CH3CN. This oxidation is suitable for a variety of thiols and disulfides and proceeds under mild conditions, in short reaction times and with high yields.

Hypervalent iodine in synthesis. XXI: A facile method for the preparation of thiosulfonic S-esters by the oxidation of diaryl disulfides or thiophenols with phenyliodine(III) bis(trifluoroacetate)

Xia, Min,Chen, Zhen-Chu

, p. 1301 - 1308 (1997)

Phenyliodine(III) bis(trifluoroacetate) can be used to readily oxidize diaryl disulfides or thiophenols to corresponding thiosulfonic S-esters with good yields under very mild conditions.

-

Fritz,Gillette

, p. 1777,1778 (1968)

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Competitive electron transfers from a tyrosyl side-chain and peptide bond in the photodegradation of N-tosyl α-aminomethylamides: An insight into photosynthesis and photodamage in the biological oxidation of water?

Hill, Roger R.,Moore, Sharon A.,Roberts, David R.

, p. 2838 - 2839 (2003)

Photo-excited N-tosyl derivatives of phenylalanyl- and, more particularly, O-methyltyrosylmethylamides undergo electron transfer from aryl to tosyl groups whereas the photo-degradation of aliphatic analogues is initiated by electron transfer from the peptide bond, suggesting the latter as one possible reason for the rapid turnover of the D1 protein in biological water oxidation when the essential mediating role of tyrosine 116 in the PSII complex is inhibited.

A general and efficient method for the preparation of organic sulfonic acids by insertion of sulfur trioxide into the metal-carbon bond of organolithiums

Smith, Keith,Hou, Duanjie

, p. 1530 - 1532 (1996)

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Thomas,Anzilotti,Hennion

, p. 408 (1940)

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Formation of o-nitrosobenzaldehyde from hydrolysis of o-nitrobenzyl tosylate. Evidence of intramolecular nucleophilic interaction

Chen, Ling-Jen,Burka, Leo T.

, p. 5351 - 5354 (1998)

Hydrolysis of o-nitrobenzyl tosylate in CH3CN:H2O (1:1, v/v) gave o- nitrobenzyl alcohol and o-nitrosobenzaldehyde in 1.8 : 1 ratio. Formation of o-nitrosobenzaldehyde indicates that the nitro group participates in the leaving of the tosylate group. o-Nitrosobenzaldehyde was reduced by biological thiols to give o-aminobenzaldehyde. Reaction of o- nitrosobenzaldehyde with 1 tool of benzylamine afforded 3-(N- benzylamino)anthranil (or its tautomer) as a major product.

Palladium nanoparticles as reusable catalyst for the synthesis of N-aryl sulfonamides under mild reaction conditions

Khalaj, Mehdi,Ghazanfarpour-Darjani, Majid,Talei Bavil Olyai, Mohamad Reza,Shamami, Sakineh Faraji

, p. 211 - 221 (2016)

An efficient palladium nanoparticles-catalyzed N-arylation of sulfonamides and sulfonyl azides is described. This procedure serves as an active protocol for intermolecular C-N bond formation using Pd(OAc)2 in PEG-400 under air. Aryl bromides and triflates react at 35°C, while aryl chlorides require heating to 50°C and give the desired products only in low yields. This reaction proceeds smoothly in acceptable yields using low catalyst loading.

Challenger,Kipping

, p. 773 (1910)

Experimental and molecular modelling studies on aromatic sulfonation

Morley, John O.,Roberts, David W.,Watson, Simon P.

, p. 538 - 544 (2002)

The mechanism of the sulfonation of toluene has been explored both experimentally and theoretically using molecular orbital methods. Sulfonation with sulfur trioxide is proposed to proceed initially via the formation of a toluene-S2O6 π-complex (3) which rearranges to form a Wheland pyrosulfonate intermediate (5) which in turn undergoes a facile prototropic rearrangement involving the transfer of the ring hydrogen at the sp3 carbon to the sulfonate oxygen atom to form toluenepyrosulfonic acid (7). Once formed, this acid is thought to attack toluene to form two equivalents of toluenesulfonic acid (6) which preferentially react with sulfur trioxide to re-form the pyrosulfonic acid (7). Experimentally, sulfonation using either acetylsulfonic acid (9), trifluoroacetylsulfonic acid (10), or trimethylacetylsulfonic acid (11), as models for pyrosulfonic acid (7), appears to show second order kinetics at room temperature. The reaction with acetylsulfonic acid (9) shows no significant kinetic isotope effect when 4deuterotoluene is used as the substrate, suggesting that sulfonation proceeds via attack of the π-electrons of the toluene ring at the sulfur atom, S8, of acetylsulfonic acid or toluenepyrosulfonic acid with simultaneous cleavage of the O7-S8 bond, where the displaced acetate or toluenesulfonate anion respectively can facilitate the removal of the ring proton at the sp3 carbon.

Photodegradation of aryl sulfonamides: N-tosylglycine

Hill, Roger R.,Jeffs, Graham E.,Roberts, David R.,Wood, Sharon A.

, p. 1735 - 1736 (1999)

Continuing uncertainty about pathways and consequences of the photolability of aryl sulfonamides is partly resolved by the results of comprehensive product analysis in the photolysis of aqueous N-tosylglycine, which indicate that intramolecular electron or hydrogen transfer (according to conditions) promote the widely reported S-N cleavage and reveal the nature of subsequent and competing processes.

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Schenk et al.

, p. 907,911 (1950)

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A novel method for sulfonation of aromatic rings with silica sulfuric acid

Hajipour, Abdol R.,Mirjalili, Bi Bi F.,Zarei, Amin,Khazdooz, Leila,Ruoho

, p. 6607 - 6609 (2004)

Direct and chemoselective sulfonation of aromatic compounds with silica sulfuric acid in 1,2-dichloeoethane or under solvent-free conditions.

Regioselective Sulfonation of Aromatic Compounds over 1,3-Disulfonic Acid Imidazolium Chloride under Aqueous Media

Moosavi-Zare, Ahmad Reza,Zolfigol, Mohammad Ali,Noroozizadeh, Ehsan

, p. 1682 - 1684 (2016)

1,3-Disulfonic acid imidazolium chloride ([Dsim]Cl), as a Bronsted acidic ionic liquid, is introduced for the sulfonation of aromatic compounds by in situ generation of sulfuric acid at 50 °C under mild conditions and in aqueous medium.

Reactions of the Nickel(I) Octaethylisobacteriochlorin Anion with Alkyl Halides

Stolzenberg, Alan M.,Stershic, Matthew T.

, p. 5397 - 5403 (1988)

Reactions of NiI(OEiBC)- with alkyl halides were investigated in bulk solution and by electrochemical means.With the exception of factor F430, the Ni hydrocorphinoid prosthetic group of methyl coenzyme M reductase, Ni(OEiBC) is the only tetrapyrrole to date that has been reduced to an isolable nickel(I) complex.NiI(OEiBC)- reacts with CH3I in a 2:1 stoichiometry to afford neutral NiII(OEiBC) in quantitative yield and CH4 and I- in lesser yields.The nickel(I) complex also reacts with methyl p-toluenesulfonate to afford CH4.Ni(OEiBC) mediates electrocatalytic reductions of alkyl halides and of methyl p-toluenesulfonate.Evidence is presented for a transient alkyl-NiIII(OEiBC) intermediate, which is reducible at potentials positive of the NiII/NiI couple.The current/potential curves of the electrocatalytic reductions were analyzed to obtain relative rate constants for a series of alkyl halides.The reactivity trends I > Br > tosyl >/= Cl and CH3 > n-C4H9 > sec-C4H9 > t-C4H9 are consistent with a nucleophilic, Sn2-like mechanism.Estimates of the second-order rate constant for reaction of NiI(OEiBC)- and CH3I suggest that the nucleophilicity of the nickel(I) complex is comparable to that of the "supernucleophile" vitamin B12s.

A Novel Concept of Acid Proliferation. Autocatalytic Fragmentation of an Acetoacetate Derivative as an Acid Amplifier

Ichimura, Kunihiro,Arimitsu, Koji,Kudo, Kazuaki

, p. 551 - 552 (1995)

tert-Butyl 2-methyl-2-(p-toluenesulfonyloxymethyl)acetoacetate was designed to be subjected to the acid-catalyzed fragmentation to liberate p-toluenesulfonic acid which can act as the autocatalyst to lead to the increment of the acid concentration in geometric progression.

-

Hisada et al.

, p. 2035 (1972)

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Cholesteryl Tosylate: A Solvolytic Investigation

Roberts, Donald D.

, p. 1269 - 1272 (1993)

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Suzuki Cross-Coupling for the incorporation of labeled methyl groups onto aryl halides. A synthesis of [14C]Tosyl chloride and its use in the synthesis of [14C]L-738,167

Braun, Matthew P.,Dean, Dennis C.,Melillo, David G.

, p. 469 - 476 (1999)

A synthesis of [4-methyl-14C]tosyl chloride has been developed which utilizes a Suzuki Cross-Coupling reaction between 4-iodophenylsulfonic acid and a labeled methyl borinate as the key step. This process avoids the poor regioselectivity typically attendant with aromatic sulfonation procedures. We now describe the use of this [14C]tosyl chloride in the synthesis of the orally active fibrinogen receptor antagonist L-738,167.

Bis Sulfate as an Organosilicon Synthon

Voronkov, M. G.,Roman, V. K.,Maletina, E. A.

, p. 277 - 280 (1982)

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Potential photoacid generators based on oxime sulfonates

Plater, M. John,Harrison, William T. A.,Killah, Ross

, p. 26 - 33 (2019)

The bis-oxime of acenaphthenequinone and the mono-oxime of benzil have been sulfonated by reaction with 4-methylbenzenesulfonyl chloride and propylsulfonyl chloride. The four sulfonated oximes were characterised by X-ray single-crystal structure determinations. Some photochemical decompositions were studied using a 6-W 254-nm immersion well lamp in dichloromethane. The 4-methylbenzenesulfonate bis-oxime of acenaphthenequinone and the 4-methylbenzenesulfonate mono-oxime of benzil both give 4-methylbenzenesulfonic acid upon irradiation but not 4-methylbenzenesulfinic acid. Fragmentation pathways are discussed. The possible use of these compounds as photoacid generators in polymer resists and the role of secondary reactions to liberate acid is discussed.

Neighboring group competition revisited: Relative abilities of cyclobutyl/cyclopentyl/phenyl groups to stabilize an electron-deficient carbon

Roberts

, p. 1341 - 1343 (1999)

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Englund,Aries,Othmer

, p. 189,193 (1953)

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Importance of repulsion of lone electron pairs in the enhanced reactivity of 1,8-naphthyridine and the large α-effect of hydrazine in the aminolyses of p-toluenesulfonyl chloride

Oae, Shigeru,Kadoma, Yoshihito

, p. 1184 - 1188 (1986)

The rates of aminolyses of p-toluenesulfonyl chloride with primary and tertiary amines have been determined both in acetonitrile and in ethanol.The Broensted plots of log krel again pKa' values fo amines (except hydrazine and 1,8-naphthyridine in acetonitrile) gave a good correlation when the aminolyses were carried out in acetonitrile.In ethanol, however, although Broensted plots with all tertiary amines show a good correlation, less basic hydrazine shows a higher reactivity than n-butylamine.The abnormal rate enhancement found with hydrazine is undoubtedly due to the α-effect, while with 1,8-naphthyridine in acetonitrile is considered to be due to the repulsion of two lone electron pairs on the two nitrogen atoms in 1,8-naphthyridine.

Hydrolysis of some imidazole, benzimidazole, and 1,2,3-benzotriazole derivatives according to HPLC and NMR diffusimetry data

Polyakova,Bulanova,Vartapetyan

, p. 820 - 822 (2001)

Hydrolysis of 1-mesylimidazole, 1-mesylbenzotriazole, and 1-tosylbenzimidazole was studied by reversed-phase HPLC and pulsed field gradient NMR diffusimetry. The hydrolysis rate constants and half reaction times were determined. The self-diffusion coeffic

A kinetic study of acid-catalyzed hydrolysis of some arylsulfonyl phthalimides

Kutuk, Halil,Ozturk, Seyhan

, p. 332 - 340 (2009)

The acid-catalyzed hydrolysis of arylsulfonyl phthalimides was studied in aqueous solutions of sulfuric, perchloric, and hydrochloric acid at 35.0 ± 0.1C. Analysis of the data by the excess acidity method and activation parameters, as well as substituent and solvent isotope effects, indicate hydrolysis by an A-2 mechanism at low acidity. At higher acidities, a changeover to an A-1 mechanism is observed.

Hydrolysis Mechanism of Alkynyl Benzoates, Tosylates, and Phosphates

Allen, Annette D.,Kitamura, Tsugio,Roberts, Kenneth A.,Stang, Peter J.,Tidwell, Thomas T.

, p. 622 - 624 (1988)

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Extremely mild and selective method for hydrolysis of tosyl esters by photo-sensitized single electron transfer reactions

Nishida,Hamada,Yonemitsu

, p. 2977 - 2980 (1990)

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Recyclable imidazolium ion-tagged nickel catalyst for microwave-assisted C-S cross-coupling in water using sulfonyl hydrazide as the sulfur source

Saini, Vaishali,Khungar, Bharti

, p. 12796 - 12801 (2018)

Herein, we report the facile and convenient synthesis of aryl sulfides through the sulfenylation of aryl halides with arylsulfonyl hydrazides, which is catalyzed by a simple and water-soluble Ni(ii) complex. The nickel complex based on the imidazolium ion-tagged salen architecture is synthesized and well characterized using various analytical techniques. The green solvent water is used as the solvent medium and moderate to good yields of aryl sulfides are obtained using 5 mol% of the catalyst under microwave irradiation. The incorporation of the ion-tag functionality helps in the recycling of the catalyst and successful reuse for up to five runs without appreciable change in its activity.

Photocleavage of o-nitrobenzyl ether derivatives for rapid biomedical release applications

Kim, Moon Suk,Diamond, Scott L.

, p. 4007 - 4010 (2006)

The externally controlled cleavage of covalently linked prodrugs, proteins, or solid-phase formulation vehicles offers potential advantages for controlled drug or gene delivery. A series of o-nitrobenzyl ester compounds (1-8) were synthesized to allow a systematic study of photolability. The o-nitrobenzyl ester was strictly required for photolability, while imido esters were not photolabile. The degradation kinetics of 1-o-phenylethyl ester was an order of magnitude faster than that of o-nitrobenzyl ester. Tosylate, phosphate, and benzoate derivatives of 1-o-nitrophenylethyl displayed similar photolability (>80% decomposition within 10 min at 3.5 mW/cm2 at 365 nm). O-o-Nitrobenzyl O′,O″-diethyl phosphate displayed the fastest decomposition at photoirradiation condition (3.5 mW/cm2, 365 nm) suitable for biological systems. We report the synthesis and photo-decomposition of 1-o-nitrophenylethyl derivatives amenable for the creation of photolabile prodrugs or formulation particles for drug depots, DNA condensation, or tissue engineering applications.

Solvolyses of Secondary Sulfonates in Aqueous Ethanol and Acetone. Nonlinear mY Relationships due to Leaving Group and Medium Effects

Bentley, William T.,Bowen, Christine T.,Brown, Herbert C.,Chloupek, Frank J.

, p. 38 - 42 (1981)

Solvolitic rate constants for secondary mesylates and tosylates in aqueous ethanol and in aqueous acetone are correlated with Winstein-Grunwald Y values.Curvature of these plots is greatest for tosylates in aqueous ethanol, especially for 2-adamantyl.Because mesylates show little or no curvature, it is argued that the results cannot be explained by mechanistic changes but by solvation effects of the leaving group in the mixed solvents.The parameter, m, measuring response to solvent ionizing power varies from 0.68 for isopropyl to 1.21 for 2-adamantyl mesylate in aqueosus acetone at 25 deg C.An alternative solvent ionizing power parameter for tosylates, YOTs , and the solvent nucleohpilicity parameter, NOTs, are evaluated for 20percent ethanol/water, 20percent acetone/water, and 40percent acetone/water.It is proposed that solvolyses of substrates having the same (or very similar) leaving group should be compared if reliable mechanistic information (e.g., nucleophilic solvation effects) is required.The tendency for "dispersion" of correlation lines for various binary mixed solvents appears to be due to both leaving-group effects and to variations in solvent nucleophilicity.By helping to account for curvature and dispersion in mY correlations, this work supports recent work in which mechanistic information was deduced from similar correlations.

BRANCHED AMINO ACID SURFACTANTS FOR AGRICULTURAL PRODUCTS

-

, (2022/01/23)

-

BRANCHED AMINO ACID SURFACTANTS

-

, (2022/01/24)

The present disclosure provides derivatives of amino acids that have branched alkyl structures and surface-active properties. The amino acid can be naturally-occurring or synthetic, or they may be obtained via a ring-opening reaction of a lactam, such as caprolactam. The amino acid may be functionalized to form a compound that is surface-active and have advantageous surfactant characteristics. The compounds of the present disclosure have low critical micelle concentrations (CMC) as well as superior ability to lower the surface tension of a liquid.

BRANCHED AMINO ACID SURFACTANTS FOR PERSONAL CARE AND COSMETIC PRODUCTS

-

, (2022/01/24)

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Primary Sulfonamide Functionalization via Sulfonyl Pyrroles: Seeing the N?Ts Bond in a Different Light

Ozaki, Tomoya,Yorimitsu, Hideki,Perry, Gregory J. P.

, p. 15387 - 15391 (2021/10/04)

Despite common occurrence in molecules of value, methods for transforming sulfonamides are distinctly lacking. Here we introduce easy-to-access sulfonyl pyrroles as synthetic linchpins for sulfonamide functionalization. The versatility of the sulfonyl pyrrole unit is shown by generating a variety of products through chemical, electrochemical and photochemical pathways. Preliminary results on the direct functionalization of primary sulfonamides are also provided, which may lead to new modes of activation.

Cornforth and Corey-Suggs reagents as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 under solvent free and microwave conditions

Fatima, Touheeth,Duguta, Govardhan,Purugula, Venkanna,Yelike, Hemanth Sriram,Kamatala, Chinna Rajanna

, p. 1001 - 1006 (2020/07/27)

Cornforth and Corey-Suggs reagents Pyridinium Dichromate (PDC) and Pyridinium Chlorochromate (PCC) were explored as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 in aqueous acetonitrile medium at room temperature within 1–4 h, while microwave assisted reactions took place within 1–4 min under solvent-free conditions. These observations indicate significant rate accelerations in microwave assisted reactions. which were explained due to the bulk activation of molecules induced by insitu generated high temperatures and pressures when microwaves are transmitted through reaction medium.

Process route upstream and downstream products

Process route

3-methylphenylsulfonyl chloride
1899-93-0

3-methylphenylsulfonyl chloride

m-toluenesulfonic acid
617-97-0

m-toluenesulfonic acid

o-toluenesulfonic acid
88-20-0

o-toluenesulfonic acid

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

Toluene-2-sulfonyl chloride
133-59-5

Toluene-2-sulfonyl chloride

Conditions
Conditions Yield
With chlorosulfonic acid; at 25 ℃; for 1.5h; Product distribution;
11.6 % Chromat.
3.2 % Chromat.
85.2 % Chromat.
16.1 % Chromat.
1.8 % Chromat.
82.1 % Chromat.
4-nitrophenyl 4-methylbenzenesulfonate
1153-45-3

4-nitrophenyl 4-methylbenzenesulfonate

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

N-(4-chlorobenzyl)-p-toluenesulfonamide
10504-98-0

N-(4-chlorobenzyl)-p-toluenesulfonamide

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

N-(4-chlorobenzyl)-4-nitroaniline

N-(4-chlorobenzyl)-4-nitroaniline

Conditions
Conditions Yield
In acetonitrile; at 65 ℃; Kinetics;
4-nitrophenyl 4-methylbenzenesulfonate
1153-45-3

4-nitrophenyl 4-methylbenzenesulfonate

4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

N-[(4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide
54879-64-0

N-[(4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

N-[(4-methoxyphenyl)methyl]-4-nitroaniline

N-[(4-methoxyphenyl)methyl]-4-nitroaniline

Conditions
Conditions Yield
In acetonitrile; at 65 ℃; Kinetics;
4-nitrophenyl 4-methylbenzenesulfonate
1153-45-3

4-nitrophenyl 4-methylbenzenesulfonate

benzylamine
100-46-9

benzylamine

N-benzyl-4-nitroaniline
14309-92-3

N-benzyl-4-nitroaniline

N-benzyl-p-toluenesulfonamide
1576-37-0

N-benzyl-p-toluenesulfonamide

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

Conditions
Conditions Yield
In acetonitrile; at 65 ℃; Kinetics;
4-nitrophenyl 4-methylbenzenesulfonate
1153-45-3

4-nitrophenyl 4-methylbenzenesulfonate

para-methylbenzylamine
104-84-7

para-methylbenzylamine

N-p-xylyl-p-toluenesulfonamide
10504-92-4

N-p-xylyl-p-toluenesulfonamide

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

(4-methyl-benzyl)-(4-nitro-phenyl)-amine

(4-methyl-benzyl)-(4-nitro-phenyl)-amine

Conditions
Conditions Yield
In acetonitrile; at 65 ℃; Kinetics;
4-nitrophenyl 4-methylbenzenesulfonate
1153-45-3

4-nitrophenyl 4-methylbenzenesulfonate

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

Conditions
Conditions Yield
With tetrabutylammomium bromide; tetra(n-butyl)ammonium hydroxide; at 40 ℃; Further Variations:; Temperatures; Kinetics; Activation energy;
2-cyanophenyl 4-methylbenzenesulfonate
36800-94-9

2-cyanophenyl 4-methylbenzenesulfonate

salicylonitrile
611-20-1

salicylonitrile

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

Conditions
Conditions Yield
With tetrabutylammomium bromide; tetra(n-butyl)ammonium hydroxide; at 40 ℃; Further Variations:; Temperatures; Kinetics; Activation energy;
4-nitrophenyl 4-toluenesulfonate
4094-37-5

4-nitrophenyl 4-toluenesulfonate

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

Conditions
Conditions Yield
With potassium chloride; bis(N,N-dimethylacetamide)hydrogen dibromobromate; In water; at 25 ℃; pH=11.60; Reagent/catalyst; pH-value; Kinetics;
(3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-p-tolylsulfanylmethyl-octahydro-azuleno[4,5-b]furan-2,8-dione
248584-37-4

(3S,3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-6-methylene-3-p-tolylsulfanylmethyl-octahydro-azuleno[4,5-b]furan-2,8-dione

grosheimin
22489-66-3

grosheimin

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

Conditions
Conditions Yield
With phosphate buffer; dihydrogen peroxide; In methanol; at 37 ℃; pH=7.4; Kinetics;
ethyl ester of p-toluenesulfonic acid
80-40-0

ethyl ester of p-toluenesulfonic acid

chloroethane
75-00-3

chloroethane

ethylbenzene
100-41-4,27536-89-6

ethylbenzene

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

C<sub>7</sub>H<sub>7</sub>O<sub>3</sub>S<sup>(1-)</sup>*3Cl<sup>(1-)</sup>*Ti<sup>(4+)</sup>

C7H7O3S(1-)*3Cl(1-)*Ti(4+)

Conditions
Conditions Yield
With titanium tetrachloride; at 25 ℃; for 2h; Product distribution; Mechanism; var. time, other Lewis acids - GaCl3, AlBr3;
24.2 % Chromat.

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