50635-72-8

Basic information

• Product Name: (-)-(R)-1-chloroethyl p-tolyl sulfoxide
• CAS NO: 50635-72-8
• Molecular Weight: 202.705
• Mol File: 50635-72-8.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (-)-(R)-1-chloroethyl p-tolyl sulfoxide(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(R)-1-chloroethyl p-tolyl sulfoxide(50635-72-8)
• EPA Substance Registry System: (-)-(R)-1-chloroethyl p-tolyl sulfoxide(50635-72-8)

Safety Data

• Hazardous Substances Data: 50635-72-8(Hazardous Substances Data)

Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 1519-40-0 (+)-(R)-ethyl p-tolyl sulfoxide 
• 106-45-6 para-thiocresol 
• 62961-00-6 (S)-1-(ethylsulfinyl)-4-methylbenzene 
• 622-63-9 ethyl p-tolyl sulfide 
• 6378-07-0 ethyl (p-tolyl)sulfoxide 

Downstream Products

• 223392-43-6 (R_S)-1-chloroethyl (4-methylphenyl) sulfoxide 
• 119487-87-5 (2R,3R)-3-(4-Chloro-phenyl)-2-methyl-1-phenyl-2-((S)-toluene-4-sulfinyl)-aziridine 
• 119487-86-4 (2R,3R)-2-Methyl-1,3-diphenyl-2-((S)-toluene-4-sulfinyl)-aziridine 
• 152994-51-9 (R)-2-Chloro-2-(toluene-4-sulfonyl)-heptan-3-one 
• 152994-45-1 (R)-2-Chloro-2-(toluene-4-sulfonyl)-pentan-3-one 
• 121174-10-5 (R)-3-Chloro-2-methyl-3-((R)-toluene-4-sulfinyl)-butan-2-ol 

Relevant articles and documents

Chain Extension of Boronic Esters with Lithiooxiranes Generated by Sulfoxide-Metal Exchange - Stereocontrolled Access to 2°/2°, 2°/3°, and 3°/3° Vicinal Diols and Related Compounds

Lithiooxiranes [LiCR1(O)CR2R3, R1 = H, Me; R2/R3 = H/Ph, H/tBu, Me/Ph], generated by sulfoxide-lithium exchange from stereodefined sulfinyl epoxides (with use of PhLi or tBuLi, THF, at or below -90 °C), were employed for the stereospecific reagent-controlled homologation of boronic esters R0-Bpin (R0 = BnCH2, allyl, cHex, Ph). Addition of TBSOTf to the intermediate ate complexes gave β-silyloxyboronates that were converted to vicinal diol monosilyl ethers by oxidative work-up with aq. NaOOH. The 2°/2° (4-32 %, dr > 98:2), 2°/3° (21-66 %, dr ≥ 65:35), and 3°/3° (59-68 %, dr ≥ 95:5) contiguous stereodiad-containing compounds created in this manner were typically obtained in a highly stereocontrolled manner. In general, cis-sulfinyl epoxides afforded anti-like stereodiads, whereas trans-sulfinyl epoxides afforded syn-like stereodiads; however, as a result of its suspected configurational instability, LiCMe(O)CHPh gave anti-like 2°/3° motifs regardless of sulfinyl epoxide stereochemistry.

Novel synthesis of optically active 2-ethylhexanoic acid, 2-ethylhexanol, and 2-ethylhexylamine via the asymmetric favorskii rearrangement

The asymmetric Favorskii rearrangement of optically active α-haloketones, which are easily prepared from chiral menthyl-4- toluenesulfoxide in several steps using primary or secondary amines, yields their corresponding secondary or tertiary chiral amides.

Facile Synthesis of α-Chlorosulfoxide Using the N,N'-Dichloro-p-toluenesulfonamide

Various unsymmetrical and symmetrical dialkyl sulfoxides or alkyl aryl sulfoxides reacted with N,N'-dichloro-p-toluenesulfonamide to yield the corresponding α-chlorosulfoxide in excellent yields under mild and neutral conditions in high regioselectivity of monochlorination at α-position of sulfoxides.