Ethyl p-toluenesulfonate

Base Information

• Chemical Name: Ethyl p-toluenesulfonate
• CAS No.: 80-40-0
• Deprecated CAS: 1195611-43-8
• Molecular Formula: C9H12O3S
• Molecular Weight: 200.258
• Hs Code.: 29041000
• European Community (EC) Number: 201-276-7
• NSC Number: 8887
• UNII: 2160N0YURF
• DSSTox Substance ID: DTXSID2058833
• Nikkaji Number: J3.853I
• Wikidata: Q27253524
• Mol file: 80-40-0.mol

Synonyms:Ethyl p-toluenesulfonate;80-40-0;Ethyl 4-methylbenzenesulfonate;Ethyl tosylate;Ethyl p-tosylate;ETHYL P-METHYLBENZENESULFONATE;Benzenesulfonic acid, 4-methyl-, ethyl ester;Ethyl p-TS;ethyl p-toluene sulfonate;p-Toluenesulfonic acid, ethyl ester;Ethyl-p-toluenesulfonate;Ethyl PTS;Ethyl 4-toluenesulfonate;p-Toluolsulfonsaeure aethyl ester;ethyl 4-methylbenzene-1-sulfonate;Ethyl toluene-4-sulphonate;NSC 8887;toluene-4-sulfonic acid ethyl ester;Ethyl p-methyl benzenesulfonate;CCRIS 1028;HSDB 5235;p-Toluenesulfonic Acid Ethyl Ester;EINECS 201-276-7;Ethylester kyseliny p-toluensulfonove;Ethyl toluene-4-sulfonate;4-Methylbenzenesulfonic acid ethyl ester;BRN 0611213;UNII-2160N0YURF;p-Toluolsulfonsaeure aethyl ester [German];AI3-08004;2160N0YURF;Ethylester kyseliny p-toluensulfonove [Czech];NSC-8887;4-11-00-00248 (Beilstein Handbook Reference);Mittel AEP;ethyl p-toluensulfonate;ethyltoluen-4-sulfonat;ethyl-p-toluene-sulfonate;ethyl-p-toluene sulphonate;Ethyl para-toluenesulfonate;ethyl paratoluene sulphonate;p-toluenesulfonic acid ethyl;WLN: 2OSWR D1;SCHEMBL76249;Ethyl p-toluenesulfonate, 98%;DTXSID2058833;Ethyl 4-methylbenzenesulfonate #;NSC8887;ethyl 4-methyl-1-benzenesulfonate;MFCD00009100;STL268850;Ethyl ester of p-Toluenesulfonic acid;ETHYL P-TOLUENESULFONATE [MI];AKOS000120217;CS-W015611;4-methyl-benzenesulfonic acid ethyl ester;LS-154168;FT-0626235;T0268;EN300-18116;H11959;A839902;Q27253524;Z57169563;F0001-2084;Ethyl p-toluenesulfonate, certified reference material, TraceCERT(R)

Chemical Property of Ethyl p-toluenesulfonate

Chemical Property:

• Appearance/Colour: Clear colorless to brownish liquid after melting
• Vapor Pressure: 0.00142mmHg at 25°C
• Melting Point: 29-33 °C(lit.)
• Refractive Index: n20/D 1.511(lit.)
• Boiling Point: 306.2 °C at 760 mmHg
• Flash Point: 157.8 °C
• PSA: 51.75000
• Density: 1.175 g/cm³
• LogP: 2.80100
• Storage Temp.: Store below +30°C.
• Sensitive.: Moisture Sensitive
• Solubility.: 1.24g/l
• Water Solubility.: Insoluble
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 200.05071541
• Heavy Atom Count: 13
• Complexity: 232

Purity/Quality:

99% ^*data from raw suppliers

EthylTosylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-40-22
• Safety Statements: 26-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Benzenesulfonic Acid Derivatives
• Canonical SMILES: CCOS(=O)(=O)C1=CC=C(C=C1)C
• Uses: Ethyl p-toluenesulfonate can be used in the manufacture of organic synthesis, and also can be used as intermediate of methylation reagent and sensitive material. It also is flexibilizer of cellulose acetate. For ethylation. 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. It was used in a study to develop a fast and accurate method for determination of residues of some common alkylating agents employed in drug synthesis by in situ derivatization-headspace-gas chromatography-mass spectrometry.

Technology Process of Ethyl p-toluenesulfonate

There total 83 articles about Ethyl p-toluenesulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

ethanol (64-17-5) + p-toluenesulfonyl chloride (98-59-9) → ethyl ester of p-toluenesulfonic acid (80-40-0)

Guidance literature:

With potassium carbonate; for 0.0833333h;

DOI:10.1016/j.tet.2007.03.083

Reference yield: 78.0%

ethanol (64-17-5) + toluene-4-sulfonic acid (104-15-4) → ethyl ester of p-toluenesulfonic acid (80-40-0)

Guidance literature:

Fe⁽³⁺⁾-exchanged montmorillonite clay; In 1,2-dichloro-ethane; at 80 ℃; for 2h;

DOI:10.1016/S0040-4020(00)00626-8

Reference yield: 78.0%

α-benzoyl-α-(p-tolylsulfonyl)diazomethane (1666-24-6) + (2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester (21728-28-9) → ethyl 5,6-dihydro-5-oxo-pyrazolo[1,5-c]quinazoline-1-carboxylate + benzoic acid ethyl ester (93-89-0,99341-95-4) + ethyl ester of p-toluenesulfonic acid (80-40-0)

Guidance literature:

With potassium carbonate; In ethanol; at 80 ℃; for 1h;

DOI:10.1021/acs.joc.0c00078

upstream raw materials:

ethanol

toluene-p-sulfonyl bromide

Ethyl p-toluenesulfinate

1-p-toluenesulfonyl-2-p-toluenesulfonylimino-1,2-dihydropyridine

Downstream raw materials:

(3-ethyl-benzothiazol-2-yl)-(1-ethyl-[4]quinolyl)-methinium ; iodide

1,3,5-tris-(1-ethyl-[4]quinolyl)-[2.2.0] pentamethine diium; diiodide

(3-ethyl-benzothiazol-2-yl)-(3-ethyl-benzoxazol-2-yl)-methinium ; iodide

3-ethyl-2-methylbenzothiazolium p-toluenesulfonate

Refernces

• 1、 -. "Method for the Preparation of Diamine Derivative". Paragraph 0284-0288. . Retrieved 2021/03/23.
• 2、 Ramu, Gopathi,Tangella, Yellaiah,Ambala, Srinivas,Nagendra Babu, Bathini. "Regioselective Ring Expansion of 3-Ylideneoxindoles with Tosyldiazomethane (TsDAM): A Metal-Free and Greener Approach for the Synthesis of Pyrazolo-[1,5- c]quinazolines". . p. 5370 - 5378. Retrieved 2020/05/19.