p-Tolyl sulfoxide

Base Information

• Chemical Name: p-Tolyl sulfoxide
• CAS No.: 1774-35-2
• Molecular Formula: C14H14OS
• Molecular Weight: 230.331
• Hs Code.: 2930909090
• European Community (EC) Number: 217-203-7
• NSC Number: 73128
• DSSTox Substance ID: DTXSID40170296
• Nikkaji Number: J48.038J
• Wikidata: Q72469914
• ChEMBL ID: CHEMBL1366230
• Mol file: 1774-35-2.mol

Synonyms:p-Tolyl sulfoxide;1774-35-2;Di-p-tolyl sulfoxide;Ditolyl sulfoxide;4,4'-Sulfinylbis(methylbenzene);Sulfoxide, ditolyl;Benzene, 1,1'-sulfinylbis[4-methyl-;Ditolyl sulphoxide;4,4'-Ditolyl sulfoxide;1-methyl-4-(4-methylphenyl)sulfinylbenzene;4,4'-Dimethyl diphenyl sulfoxide;Toluene, 4,4'-sulfinylbis-;Bis(p-tolyl)sulphoxide;NSC 73128;p-TOLUENE, 1,1'-SULFINYLBIS-;EINECS 217-203-7;Benzene, 1,1'-sulfinylbis(4-methyl-;BRN 2048587;bis(4-methylphenyl) sulfoxide;1-methyl-4-(4-methylbenzenesulfinyl)benzene;4,4/'-Dimethyldiphenylsulfoxide;4,4'-Dimethyldiphenylsulfoxide;Benzene, 1,1'-sulfinylbis(4-methyl- (9CI);4-06-00-02173 (Beilstein Handbook Reference);Toluene,4'-sulfinylbis-;p-Tolyl sulfoxide, 97%;p-Toluene,1'-sulfinylbis-;bis(4-methylphenyl)sulfoxide;NCIOpen2_003744;4,4-Dimethyldiphenylsulfoxide;Bis(p-methylphenyl) sulfoxide;MLS000105795;SCHEMBL235851;WLN: 1R DSO&R D1;CHEMBL1366230;MJWNJEJCQHNDNM-UHFFFAOYSA-;DTXSID40170296;Benzene,1'-sulfinylbis[4-methyl-;HMS2406I07;4,4''-Sulfinylbis(Methylbenzene);BAA77435;NSC73128;MFCD00008546;NSC-73128;AKOS005167035;AC-4577;AS-62176;SMR000102772;LS-154088;1-methyl-4-(4-methylphenyl)sulfinyl-benzene;FT-0743507;T1075;4-methyl-1-[(4-methylphenyl)sulfinyl]benzene;Benzene,1-methyl-4((phenylmethyl)sulfinyl))-;D92446;1-Methyl-4-[(4-methylphenyl)sulfinyl]benzene #;A812257;W-108838

Chemical Property of p-Tolyl sulfoxide

Chemical Property:

• Vapor Pressure: 1.39E-05mmHg at 25°C
• Melting Point: 94-96 °C(lit.)
• Refractive Index: 1.641
• Boiling Point: 378.3 °C at 760 mmHg
• Flash Point: 182.6 °C
• PSA: 36.28000
• Density: 1.19 g/cm³
• LogP: 4.33580
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 230.07653624
• Heavy Atom Count: 16
• Complexity: 211

Purity/Quality:

98% ^*data from raw suppliers

p-Tolyl Sulfoxide >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: CC1=CC=C(C=C1)S(=O)C2=CC=C(C=C2)C

Technology Process of p-Tolyl sulfoxide

There total 47 articles about 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: 96.0%

di-(p-tolyl)sulfane (620-94-0) → di(p-tolyl) sulfoxide (1774-35-2)

Guidance literature:

With o-iodosobenzoic acid; In water; acetic acid; for 2h;

DOI:10.1080/00397919208020500

Reference yield: 91.0%

3-[(4-methylphenyl)sulfinyl]propanoic acid tert-butyl ester (911820-09-2) + bis(4-methylphenyl)iodonium trifluoromethanesulfonate (123726-16-9) → di(p-tolyl) sulfoxide (1774-35-2)

Guidance literature:

With potassium hydroxide; In water; toluene; at 20 ℃; for 24h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.8b03046

Reference yield: 85.0%

di-(p-tolyl)sulfane (620-94-0) → bis(4-methylphenyl) sulfone (599-66-6) + di(p-tolyl) sulfoxide (1774-35-2)

Guidance literature:

With [bis(acetoxy)iodo]benzene; In chloroform; at 40 ℃; for 72h;

DOI:10.1246/bcsj.72.2351

upstream raw materials:

toluene

para-methylphenylmagnesium bromide

di-(p-tolyl)sulfane

1-benzenesulfinyl-4-methyl-benzene

Downstream raw materials:

benzyl 4-methylphenyl sulfoxide

2,8-dimethyldibenzothiophene

bis(4-methylphenyl) sulfone

tris(4-methylphenyl)sulfonium chloride

Refernces

An asymmetric synthesis of esters and γ-lactones with simultaneous construction of vicinal stereogenic carbons at the α- and β-position starting from optically active 1-chlorovinyl p-tolyl sulfoxides

10.1016/j.tetasy.2008.01.040

The research presented in the scholarly article focuses on the asymmetric synthesis of esters and c-lactones with the simultaneous construction of vicinal stereogenic carbons at the a- and ?-positions. The process starts with optically active 1-chlorovinyl p-tolyl sulfoxides, which are synthesized from aldehydes or unsymmetrical ketones and (R)-(-)-chloromethyl p-tolyl sulfoxide in two or three steps. These sulfoxides react with the lithium enolate of carboxylic acid tert-butyl esters to yield adducts with high 1,3- and 1,4-chiral induction from the stereogenic sulfur center, with the adducts then converted to optically active esters and c-lactones. The study investigates the diastereomeric excess (de) and enantiomeric excess (ee) of these adducts and c-lactones, using techniques such as 1H NMR spectroscopy, HPLC with chiral stationary columns, and specific rotation measurements to determine the stereochemistry of the products. The reaction's generality was tested with various substrates, and the results showed high yields and selectivity, although some cases exhibited lower diastereoselectivity. The research was supported by a Grant-in-Aid for Scientific Research from the Japanese government.