154010-96-5

Basic information

• Product Name: 3-AZETIDINOL, 1-[(4-METHYLPHENYL)SULFONYL]-
• Synonyms: 3-AZETIDINOL, 1-[(4-METHYLPHENYL)SULFONYL]-;N-p-tosyl-3-azetidinol;1-[(4-Methylphenyl)sulfonyl]-3-azetidinol;1-Tosyl-3-azetidinol;1-Tosylazetidin-3-ol
• CAS NO: 154010-96-5
• Molecular Formula: C₁₀H₁₃NO₃S
• Molecular Weight: 227.28
• Mol File: 154010-96-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-AZETIDINOL, 1-[(4-METHYLPHENYL)SULFONYL]-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AZETIDINOL, 1-[(4-METHYLPHENYL)SULFONYL]-(154010-96-5)
• EPA Substance Registry System: 3-AZETIDINOL, 1-[(4-METHYLPHENYL)SULFONYL]-(154010-96-5)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 154010-96-5(Hazardous Substances Data)

Upstream product

• 76543-27-6 1-(p-toluenesulfonyl) azetidin-3-one 
• 18621-18-6 azetion-3-ol hydrochloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 154010-95-4 1-(p-Toluenesulfonyl)-3-(tert-butyldimethylsiloxy)azetidine 
• 883909-30-6 1-(p-toluenesulfonyl)-3-(tetrahydropyran-2-yloxy)azetidine 
• 70-55-3 toluene-4-sulfonamide 
• 154010-94-3 3-(p-toluenesulfonamido)propane-2-ol-1-(p-toluenesulfonate) t-butyldimethylsilyl ether 
• 154010-93-2 3-(p-toluenesufonamido)propane-2-ol-1-(p-toluenesulfonate) 

Relevant articles and documents

Ring-Expansion Reactions of Epoxy Amides and Enamides: Functionalized Azetidines, Dihydrofurans, Diazocanes, or Dioxa-3-azabicyclonon-4-enes?

Functionalized azetidines, 2,3-dihydrofurans, or the unorthodox dioxa-3-azabicyclonone-4-ene motifs are the products from transition metal-free reaction between N-oxiranylmethyl benzenesulfonamide and β-chloro-cinnamaldehyde, depending on whether one uses

Regioselective Synthesis of 3-Hydroxy-4,5-alkyl-Substituted Pyridines Using 1,3-Enynes as Alkynes Surrogates

The poor regioselectivity of the [4 + 2] cycloaddition of 3-azetidinones with internal alkynes bearing two alkyl substituents via nickel-catalyzed carbon-carbon activation is addressed using 1,3-enynes as substrates. The judicious choice of substitution on the enyne enables complementary access to each regioisomer of 3-hydroxy-4,5-alkyl-substituted pyridines, which are important building blocks in medicinal chemistry endeavors.

1,5-rhodium shift in rearrangement of N -arenesulfonylazetidin-3-ols into benzosultams

Benzosultams are synthesized in an enantiopure form starting from α-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by β-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.

Improved synthesis of an energetic material, 1,3,3-trinitroazetidine (TNAZ) exploiting 2-iodoxy benzoic acid (IBX) as an oxidising agent

Tetrahydropyranyl protected 1,3-dihalo-2-propanol reacts with p-toluene sulfonamide in the presence of K2CO3 to give corresponding N-p-tosyl-3-azetidinol. Deprotection and oxidation with iodoxy benzoic acid followed by oximation of N-p-tosyl-3-azetidinone readily affords the corresponding azetidine oxime in almost quantitative yield. The subsequent oxidative nitrolysis of oxime gives 1,3,3-trinitroazetidine (TNAZ) through a new sequence of reactions with excellent purity (> 99%) and moderate yield (40%).

Synthesis of 1,3,3-Trinitroazetidine via the Oxidative Nitrolysis of N-p-Tosyl-3-azetidinone Oxime

The tert-butyldimethylsilyl ether of 1,3-dibromo-2-propanol reacted with p-toluenesulfonamide in the presence of K2CO3 to give the corresponding N-p-tosyl-3-azetidinol.The same azetidinol was obtained when the similarly silyl-protected 3-(p-toluenesulfonamido)propan-2-ol 1(p-toluenesulfonate) was treated with LiH.Desilylation and oxidation of the N-p-tosyl-3-azetidinol followed by oximation readily afforded N-p-tosyl-3-azetidinone oxime.Oxidative nitrolysis of the latter intermediate delivered 1,3,3-trinitroazetidine through a new sequence of reactions.

Novel Syntheses of 1,3,3-Trinitroazetidine

Alternative methods for the synthesis of 1,3,3-trinitroazetidine (TNAZ) from epichlorohydrin, and benzhydrylamine have been developed.These approaches employ N-sulfonyl-3-(hydroxyimino)azetidines as penultimate intermediates and represent an improvement over previously published methods which require either diazo containing intermediates or involve low yielding procedures.Parallel methods employing N-benzhydryl- and N-benzyl-3-(hydroxyimino)azetidine were also investigated as alternate routes to TNAZ

Synthesis of 1,3,3-Trinitroazetidine

The t-butyldimethylsilyl ether of 3-(p-toluenesulfonamido)propane-2-ol-1-(p-toluenesulfonate) on treatment with LiH undergoes ring closure to the corresponding azetidine which is readily converted to N-tosyl-3-azetidinone oxime.By oxidative nitrolysis the latter affords 1,3,3-trinitroazetidine.