51599-68-9

Basic information

• Product Name: Pyrrolidine, 1-(methylsulfonyl)- (9CI)
• Synonyms: Pyrrolidine, 1-(methylsulfonyl)- (9CI);1-Methanesulfonyl-pyrrolidine
• CAS NO: 51599-68-9
• Molecular Formula: C₅H₁₁NO₂S
• Molecular Weight: 149.21134
• Product Categories: THIOL
• Mol File: 51599-68-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pyrrolidine, 1-(methylsulfonyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolidine, 1-(methylsulfonyl)- (9CI)(51599-68-9)
• EPA Substance Registry System: Pyrrolidine, 1-(methylsulfonyl)- (9CI)(51599-68-9)

Safety Data

• Hazardous Substances Data: 51599-68-9(Hazardous Substances Data)

Upstream product

• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 10321-62-7 1-(phenylmethylsulfonyl)pyrrolidine 
• 154323-57-6 almotriptan 
• 1041377-70-1 1-phenyl-2-(pyrrolidin-1-ylsulfonyl)ethan-1-one 
• 93407-31-9 diphenylmethanesulfonyl-pyrrolidine 
• 92-52-4 biphenyl 
• 123-75-1 pyrrolidine 

Relevant articles and documents

Mechanisms of Hydrolysis of (Trimethylsilyl)methanesulfonyl Chloride. Sulfene-Enamine Reactions in Water

Kinetic, product analysis, and deuteration experiments are consistent with the following mechanisms of hydrolysis of (trimethylsilyl)methanesulfonyl chloride (1) (in 0.01 M KCl at 1 deg C): (a) pH /= 10.0, attack of hydroxide anion (i) at silicon to yield sulfene (5) and (ii) at an α-hydrogen to form (trimethylsilyl)sulfene (4), in each case followed by trapping of the sulfene to give either methanesulfonate (3) or (trimethylsilyl)methanesulfonate (6) salts.Aqueous potassium fluoride catalyzes the hydrolysis of 1 with formation of the methanesulfonate 3, evidently by way of silicophilic attack of fluoride anion on 1 with formation of sulfene (5).Reaction of 1 with an enamine 7 in water (at pH 8 or 9), with or without fluoride, gives two characteristic sulfene-enamine products, (i) the four-membered cycloadduct 8 and (ii) the methylsulfonyl aldehyde 9.The same or related products are also obtained from methanesulfonyl, 2-propanesulfonyl, and phenylmethanesulfonyl chlorides and enamines in water (at pH 9).Hydrolysis of 1 is also catalyzed by aniline or triethylamine evidently giving 5.