80-40-0

Basic information

• Product Name: Ethyl p-toluenesulfonate
• Synonyms: 4-methyl-benzenesulfonicaciethylester;Benzenesulfonicacid,4-methyl-,ethylester;Ethyl 4-methylbenzenesulfonate;Ethyl ester of p-Toluenesulfonic acid;Ethyl para-toluenesulfonate;Ethyl p-TS;Ethyl toluene-4-sulfonate;Ethylester kyseliny p-toluensulfonove
• CAS NO: 80-40-0
• Molecular Formula: C₉H₁₂O₃S
• Molecular Weight: 200.25
• EINECS: 201-276-7
• Product Categories: Sulphur Derivatives;Organic Building Blocks;Sulfur Compounds;Tosylates
• Mol File: 80-40-0.mol

Chemical Properties

• Melting Point: 29-33 °C(lit.)
• Boiling Point: 158-162 °C10 mm Hg(lit.)
• Flash Point: 316 °F
• Appearance: Clear colorless to pale brown/Liquid After Melting
• Density: 1.174 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00142mmHg at 25°C
• Refractive Index: n20/D 1.511(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 1.24g/l
• Water Solubility: Insoluble
• Sensitive: Moisture Sensitive
• Merck: 14,3858
• BRN: 611213
• CAS DataBase Reference: Ethyl p-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl p-toluenesulfonate(80-40-0)
• EPA Substance Registry System: Ethyl p-toluenesulfonate(80-40-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-40-22
• Safety Statements: 26-45-36/37/39
• RIDADR: UN2811
• WGK Germany: 3
• RTECS: XT6825000
• F: 21
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 80-40-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Ethyl p-toluenesulfonate is used as a reagent in the manufacture of organic synthesis for its ability to facilitate various chemical reactions and processes.
Used as a Methylating Agent:
Ethyl p-toluenesulfonate is used as an intermediate for methylation reactions, providing a source of methyl groups that can be transferred to other molecules.
Used as a Sensitive Material:
Ethyl p-toluenesulfonate is used as a sensitive material in applications where its reactivity and properties are crucial for the desired outcome.
Used as a Flexibilizer for Cellulose Acetate:
Ethyl p-toluenesulfonate is used as a flexibilizer for cellulose acetate, enhancing the flexibility and performance of the material.
Used in Ethylation:
Ethyl p-toluenesulfonate is used for ethylation purposes, where the introduction of an ethyl group is required in a chemical reaction.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Ethyl p-toluenesulfonate was used to develop an extraction method for methyl and ethyl esters of various sulfonic acids in active pharmaceutical ingredients using solid-phase micro extraction coupled to GC/MS in the selected ion monitoring mode. This method allows for the fast and accurate determination of residues of common alkylating agents employed in drug synthesis.
Used in Analytical Chemistry:
Ethyl p-toluenesulfonate was used in a study to develop a fast and accurate method for the determination of residues of some common alkylating agents employed in drug synthesis by in situ derivatization-headspace-gas chromatography-mass spectrometry. This method provides a reliable and efficient way to analyze and detect the presence of these agents in samples.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 34, p. 2710, 1986 DOI: 10.1248/cpb.34.2710The Journal of Organic Chemistry, 39, p. 3454, 1974 DOI: 10.1021/jo00937a050

Safety Profile

Moderately toxic by subcutaneous and intraperitoneal routes. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidzing materials. To fight fire, use CO2, dry chemical. When heated to decomposition it emits hlghly toxic fumes of SOx. See also SULFONATES and ESTERS.

InChI:InChI=1/C9H12O3S/c1-3-12-13(10,11)9-6-4-8(2)5-7-9/h4-7H,3H2,1-2H3

Upstream product

• 1858-86-2 Ethyl p-toluenesulfinate 
• 74-85-1 ethene 
• 104-15-4 toluene-4-sulfonic acid 
• 122-51-0 orthoformic acid triethyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 683-08-9 Diethyl methylphosphonate 
• 80-48-8 methyl p-toluene sulfonate 
• 78-38-6 ethylphosphonic acid diethyl ester 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 541-41-3 chloroformic acid ethyl ester 
• 141-97-9 ethyl acetoacetate 
• 97-62-1 Ethyl isobutyrate 
• 105-53-3 diethyl malonate 
• 64-17-5 ethanol 

Downstream Products

• 137414-31-4 1-ethyl-2-ethylsulfanyl-quinolinium; toluene-4-sulfonate 
• 70591-60-5 2-ethylsulfanyl-3-methyl-benzothiazolium; toluene-4-sulfonate 
• 105837-99-8 3-(1-ethyl-[2]piperidyl)-propionic acid ethyl ester 
• 89-50-9 2-(ethylamino)benzoic acid 
• 6263-62-3 benzyl(ethyl)sulfane 
• 122-95-2 1,4-diethoxybenzene 
• 108696-20-4 N,N'-diethyl-N,N,N',N'-tetramethyl-2,2'-butanediyldioxy-di-anilinium; bis-(toluene-4-sulfonate) 
• 7223-45-2 3-diethylamino-3-methyl-1-pentyne 
• 622-60-6 1-ethoxy-4-methylbenzene 
• 74368-00-6 4-allyl-1-ethoxy-2-methoxybenzene 
• 622-63-9 ethyl p-tolyl sulfide 
• 100-41-4 ethylbenzene 
• 75-03-6 ethyl iodide 
• 1678-91-7 ethyl-cyclohexane 

Relevant articles and documents

Regio- And stereoselective electrochemical synthesis of sulfonylated enethers from alkynes and sulfonyl hydrazides

An electrooxidative direct difunctionalization of internal alkynes with sulfonyl hydrazides has been developed for the construction of sulfonated enethers. In this transformation, metal catalysts or stoichiometric amount of oxidants are not required and molecular nitrogen and hydrogen are the sole byproducts, providing a simple and green approach for preparing various sulfonyl tetrasubstituted alkenes. Notably, the protocol could be efficiently scaled up and the follow-up procedures of the corresponding functionalized alkenes demonstrate the practicality of the electrochemical synthesis.

Method for the Preparation of Diamine Derivative

The present invention relates to high yield. The present invention relates to a process for preparing high purity ethaboxate p - toluenesulphonate or hydrates thereof. To the present invention, generation of a dielectric toxic substance and a side reaction product can be suppressed, and high yield, high purity of edoxaba p - toluenesulphonate or a hydrate thereof can be advantageously used.

Regioselective Ring Expansion of 3-Ylideneoxindoles with Tosyldiazomethane (TsDAM): A Metal-Free and Greener Approach for the Synthesis of Pyrazolo-[1,5- c]quinazolines

An efficient, metal-free approach to access pyrazolo-[1,5-c]quinazolines with 3-ylideneoxindoles and tosyldiazomethane (TsDAM) under mild aqueous reaction conditions has been developed and the solvent involvement in the present reaction has also been explored for the first time. This greener approach involves 1,3-dipolar cycloaddition, regioselective ring expansion, followed by the elimination of tosyl group with aqueous base in a single operation, and the product can be isolated in high purity without column chromatographic separation. The method is also compatible with a large variety of functional groups, providing good to excellent yields in water, thus resulting in a decrease of environmental impact in the pharmaceutical industry.

Visible-light-initiated regioselective sulfonylation/cyclization of 1,6-enynes under photocatalyst- And additive-free conditions

Without employing any photocatalyst and additive, an economical, eco-friendly and practical strategy has been developed for the visible-light-initiated regioselective sulfonylation/cyclization of 1,6-enynes in a biomass-derived green solvent 2-methylTHF from easily accessible sulfonyl chlorides under open-air conditions at room temperature. Compared with conventional heating conditions, the use of a 3 W blue light-emitting diode (LED) or sunlight not only reduces energy consumption but also minimizes side reactions. This transformation has excellent regioselectivity, mild reaction conditions, broad substrate scope and ease of scale-up. Moreover, mechanistic studies indicated that a sulfonyl radical pathway was involved in this reaction.

Mild alkaline hydrolysis of hindered esters in non-aqueous solution

Sterically hindered esters of carboxylic acids, which are considered very resistant to saponification, were rapidly and efficiently saponified in a non-aqueous medium using NaOH in MeOH/CH2Cl2 (1:9) at room temperature. Furthermore, this reaction protocol was extended and successfully applied to the hydrolysis of tosylates and N-tosyl indoles.

Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent

An alternative method for forming sulfonates through hypervalent iodine(III) reagent-mediated oxidation of sodium sulfinates has been developed. This transformation involves trapping reactive sulfonium species using alcohols. With additional optimization of the reaction conditions, the method appears extendable to other nucleophiles such as electron-rich aromatic systems or cyclic ethers through a ring opening pathway.

Copper-Catalyzed Multicomponent Reaction of DABCO·(SO2)2, Alcohols, and Aryl Diazoniums for the Synthesis of Sulfonic Esters

A Cu-catalyzed multicomponent cascade reaction of DABCO·(SO2)2 (DABSO), alcohol, and aryl diazonium tetrafluoroborate was developed which afforded sulfonic esters in moderate to good chemical yields. In this reaction, the SO2 surrogate DABSO was used for the first time in the synthesis of sulfonic aliphatic esters. This multicomponent reaction was carried out under mild conditions and tolerated a wide range of substrates, which provides a new and efficient strategy for the synthesis of sulfonic esters.

Method for synthesizing cis-tritosylate

The invention discloses a method for preparing cis-tritosylate. The cis-tritosylate shown in structural formula (II) is obtained by carrying out a reaction between a compound shown in structural formula (I) and toluene sulfonyl chloride in an anhydrous pyridine solvent according to an equal molar ratio. According to the method, use of an inorganic alkali catalyst Na2CO3 or K2CO3 is avoided, problems about hydrolysis of the toluene sulfonyl chloride are solved, and an obtained product is high in yield and free of other side reaction, and is not required to be separated by virtue of a method of column chromatography and the like.

Ionic liquid brush as an efficient and reusable heterogeneous catalytic assembly for the tosylation of phenols and alcohols in neat water

A very efficient and reusable heterogeneous ionic liquid brush assembly was developed. The catalyst exhibits high catalytic activity for the tosylation of phenols and alcohols in neat water. Moreover, the catalyst shows outstanding stability and reusability, and it can be simply and effectively recovered and reused five times without noticeable loss of catalytic activity.

The influence of electronic perturbations on the Sulfur-Fluorine Gauche Effect Dedicated to Prof. Dr. Antonio Togni on the occasion of his 60th birthday.

Herein, a solution phase NMR conformer population analysis is employed to probe the effect of remote electronic perturbations on the conformational equilibria of a series of para-substituted β-fluorosulfides (1), sulfoxides (2) and sulfone derivatives (3). Conformations that allow for stabilizing stereoelectronic (σC-H → σ?C-F) and electrostatic (Fδ-...Sδ+) interactions predominate: this is consistent with the Sulfur-Fluorine Gauche Effect. The molar fractions (χ) of the two possible gauche conformers correlate linearly with the electron-withdrawing aptitude of the para-substituent, rendering the system ideally suited for a Hammett-type analysis. Despite the clear influence that the remote para-substituents have on conformer population, this is superseded by the oxidation state on sulfur (II, IV, VI), where an increased preference for the gauche conformer follows the trend: sulfide sulfone sulfoxide. It is envisaged that this proof of concept in controlling conformer population, either by proximal (oxidation state) or remote tuning (para-substituent), will find application in molecular design.