(R)-(+)-Methyl p-tolyl sulfoxide

Base Information

• Chemical Name: (R)-(+)-Methyl p-tolyl sulfoxide
• CAS No.: 1519-39-7
• Molecular Formula: C8H10OS
• Molecular Weight: 154.233
• Hs Code.: 2930909090
• European Community (EC) Number: 604-821-0
• DSSTox Substance ID: DTXSID00448185
• Wikidata: Q72491734
• Mol file: 1519-39-7.mol

Synonyms:(R)-(+)-Methyl p-tolyl sulfoxide;1519-39-7;(R)-1-methyl-4-(methylsulfinyl)benzene;(R)-METHYL P-TOLYLSULFOXIDE;1-methyl-4-[(R)-methylsulfinyl]benzene;Benzene, 1-methyl-4-[(R)-methylsulfinyl]-;(r)-methyl p-tolyl sulfoxide;SCHEMBL1094237;DTXSID00448185;FEVALTJSQBFLEU-SNVBAGLBSA-N;(R)-(+)-methyl p-tolylsulfoxide;CS-M1249;MFCD00151502;(R)-(+)-methyl rho-tolyl sulfoxide;AKOS015890843;Sulfoxide, methyl p-tolyl, (R)-()-;CS-13842;(R)-(+)-Methyl p-tolyl sulfoxide, 99%;Benzene, 1-methyl-4-(methylsulfinyl)-, (R)-;1-[(R)-METHANESULFINYL]-4-METHYLBENZENE;AB-131/40227926;J-008866

Chemical Property of (R)-(+)-Methyl p-tolyl sulfoxide

Chemical Property:

• Vapor Pressure: 0.00574mmHg at 25°C
• Melting Point: 73-75 °C(lit.)
• Refractive Index: 1.59
• Boiling Point: 282.4 °C at 760 mmHg
• Flash Point: 124.6 °C
• PSA: 36.28000
• Density: 1.15 g/cm³
• LogP: 2.59810
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 154.04523611
• Heavy Atom Count: 10
• Complexity: 125

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-(+)-Methyl p-tolyl sulfoxide 99% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)C
• Isomeric SMILES: CC1=CC=C(C=C1)[S@](=O)C

Technology Process of (R)-(+)-Methyl p-tolyl sulfoxide

There total 77 articles about (R)-(+)-Methyl p-tolyl sulfoxide 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: 98.0%

(S)-1-(bromomethylsulfinyl)-4-methylbenzene (31350-96-6) + phenylboronic acid (98-80-6) → biphenyl (92-52-4,1594-86-1) + (R)-methyl p-tolyl sulfoxide (1519-39-7) + (R)-1-(benzylsulfinyl)-4-methylbenzene (4820-08-0,10381-70-1,68680-65-9,4820-07-9)

Guidance literature:

With cesium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; Heating;

DOI:10.1021/jo0487552

Reference yield: 97.0%

4-methoxyphenylboronic acid (5720-07-0) + (S)-1-(bromomethylsulfinyl)-4-methylbenzene (31350-96-6) → (R)-(+)-4-methoxybenzyl 4'-methylphenyl sulfoxide + (R)-methyl p-tolyl sulfoxide (1519-39-7) + 4,4'-Dimethoxybiphenyl (2132-80-1)

Guidance literature:

With cesium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; Heating;

DOI:10.1021/jo0487552

Reference yield: 97.0%

methylmagnesium bromide (75-16-1) + (-)-menthyl p-toluenesulfinate (1517-82-4) → (R)-methyl p-tolyl sulfoxide (1519-39-7)

Guidance literature:

In toluene; at -60 - -20 ℃;

DOI:10.1021/jo00274a032

upstream raw materials:

methyl magnesium iodide

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

4-methylphenyl methylsulfide

Methyl p-tolyl sulfoxide

Downstream raw materials:

5-oxo-6-(p-tolylsulfinyl)hexanoic acid

[(R)-1-Furan-2-yl-2-((R)-toluene-4-sulfinyl)-ethyl]-phenyl-amine

[(S)-1-Furan-2-yl-2-((R)-toluene-4-sulfinyl)-ethyl]-phenyl-amine

2-<(4-methylphenyl)sulfinyl>-1-(2-pyridyl)ethanone

Refernces

• 1、 Fernandez, Inmaculada,Valdivia, Victoria,Leal, Manuel Pernia,Khiar, Noureddine. "C2-symmetric bissulfoxides as organocatalysts in the allylation of benzoyl hydrazones: Spacer and concentration effects". . p. 2215 - 2218. Retrieved 2007.
• 2、 Di Stefano, Stefano,Mazzonna, Marco,Bodo, Enrico,Mandolini, Luigi,Lanzalunga, Osvaldo. "Photoinversion of sulfoxides as a source of diversity in dynamic combinatorial chemistry". . p. 142 - 145. Retrieved 2011.
• 3、 Sprout, Christopher M.,Seto, Christopher T.. "Using enzyme inhibition as a high throughput method to measure the enantiomeric excess of a chiral sulfoxide". . p. 5099 - 5102. Retrieved 2005.
• 4、 Superchi, Stefano,Donnoli, Maria Irene,Rosini, Carlo. "Enantiopure p,p'-disubstituted 1,2-diphenylethane-1,2-diols as chiral inducers in the Ti-mediated oxidation of sulfides: A case of reversal of asymmetric induction by fluorine substitution". . p. 8541 - 8544. Retrieved 1998.
• 5、 Corey,Weigel,Chamberlin,et al.. "Total synthesis of maytansine". . p. 6613 - 6615. Retrieved 1980.
• 6、 Abo, Mitsuru,Okubo, Akira,Yamazaki, Sunao. "Preparative asymmetric deoxygenation of alkyl aryl sulfoxides by Rhodobacter sphaeroides f.sp. denitrificans". . p. 345 - 348. Retrieved 1997.
• 7、 Reetz, Manfred T.,Merk, Claudia,Naberfeld, Guido,Rudolph, Joachim,Griebenow, Nils,Goddard, Richard. "3,3'-Dinitro-octahydrobinaphthol: A new chiral ligand for metal-catalyzed enantioselective reactions". . p. 5273 - 5276. Retrieved 1997.
• 8、 Gawronski, J. K.,Polonski, T.,Lightner, D. A.. "SULFOXIDES AS CHIRAL COMPLEXATION AGENTS. CONFORMATIONAL ENANTIOMER RESOLUTION AND INDUCED CIRCULAR DICHROISM OF BILIRUBINS". . p. 8053 - 8066. Retrieved 1990.
• 9、 Tarallo, Vincenzo,Sudarshan, Kasireddy,Nosek, Vladimír,Mí?ek, Jirí. "Development of a simple high-throughput assay for directed evolution of enantioselective sulfoxide reductases". supporting information. p. 5386 - 5388. Retrieved 2020/06/04.
• 10、 Yang, Jiawei,Wen, Yuanmei,Peng, Liaotian,Chan, Yu,Cheng, Xiaoling,Chen, Yongzheng. "Identification of MsrA homologues for the preparation of (R)-sulfoxides at high substrate concentrations". . p. 3381 - 3388. Retrieved 2019/04/01.