147621-21-4

Basic information

• Product Name: 1-(TERT-BUTOXYCARBONYL)AZETIDINE
• Synonyms: 1-(TERT-BUTOXYCARBONYL)AZETIDINE;TERT-BUTYL AZETIDINE-1-CARBOXYLATE;tert-Butyl 1-azetidinecarboxylate;1-Boc-azetidine
• CAS NO: 147621-21-4
• Molecular Formula: C₈H₁₅NO₂
• Molecular Weight: 157.21
• Mol File: 147621-21-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 198.7±9.0 °C(Predicted)
• Appearance: /
• Density: 1.053±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -1.28±0.20(Predicted)
• CAS DataBase Reference: 1-(TERT-BUTOXYCARBONYL)AZETIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(TERT-BUTOXYCARBONYL)AZETIDINE(147621-21-4)
• EPA Substance Registry System: 1-(TERT-BUTOXYCARBONYL)AZETIDINE(147621-21-4)

Safety Data

• Hazardous Substances Data: 147621-21-4(Hazardous Substances Data)

Usage

General Description

1-(tert-butoxycarbonyl)azetidine, also known as TBOC azetidine, is a chemical compound used in organic synthesis and the pharmaceutical industry. It is a derivative of azetidine, a four-membered heterocycle, and contains a tert-butoxycarbonyl (Boc) protecting group. The Boc group is commonly used to protect amines during chemical reactions, as it can be easily removed under mild conditions. TBOC azetidine has been utilized in the preparation of various pharmaceutical compounds and building blocks, and its unique structure and reactivity make it a valuable tool in organic chemistry research. Additionally, the Boc group can be selectively removed to reveal the free amine functionality, making TBOC azetidine a versatile building block for the synthesis of complex molecules.

Upstream product

• 254454-54-1 tert-butyl-3-iodoazetidine-1-carboxylate 
• 503-29-7 azetidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 78797-58-7 azetidine hydrochloride 
• 141699-58-3 3-methanesulfonyloxy-azetidine-1-carboxylic acid tert-butyl ester 
• 34619-03-9 di-tert-butyl dicarbonate 
• 67-64-1 acetone 

Downstream Products

• 141699-55-0 tert-butyl 3-hydroxyazetidine-1-carboxylate 
• 42116-55-2 methyl 3-tert-butoxycarbonylaminopropionate 
• 1063992-92-6 3-[1-(4-difluoromethoxy-benzenesulfonyl)-1H-indol-5-yl]-azetidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Electrophile dependent mechanisms in the asymmetric trapping of α-lithio-N-(tert-butoxythiocarbonyl)azetidine

Sn-Li exchange and ‘poor man's Hoffmann tests’ establish asymmetric trapping of α-lithio-N-(tert-butoxythiocarbonyl) (Botc) azetidine to be controlled by dynamic thermodynamic resolution or dynamic kinetic resolution, depending on the electrophile. Unusually, different configurational stability is seen for the anion generated by lithiation compared to transmetallation. Configurational stability of α-lithio-N-Boc azetidine indicates instability with theN-Botc system is due to the C-S group.

Reducing dehalogenating method of organic halogenated compound

The invention discloses a reducing dehalogenating method of an organic halogenated compound. The reducing dehalogenating method comprises: mixing an organic halogenated compound R-X, a non-noble metalpromoter, a sulfide and an alkali, and carrying out a reducing dehalogenating reaction to obtain a reducing product R-H, wherein R is at least one selected from alkyl and aryl, and X is at least oneselected from iodine, bromine and chlorine. According to the present invention, the types and the ratio (especially the specific type of the promoter) of various raw materials used in the reducing dehalogenating reaction, the corresponding reaction conditions and the like are researched and improved, such that the problems of use of highly-toxic or expensive reagent, poor tolerance of the group, narrow application range of the substrate and the like in the prior art can be effectively solved.

Photoredox-Mediated Direct Cross-Dehydrogenative Coupling of Heteroarenes and Amines

A photoredox-mediated direct cross-dehydrogenative coupling reaction to accomplish α-aminoalkylation of N-heteroarenes is reported. This mild reaction has a broad substrate scope, offers the first general method for synthesis of aminoalkylated N-heteroarenes without the need for substrate prefunctionalization, and is scalable to the gram level. Furthermore, the reaction was found to be applicable to other hydrogen donors besides amines (i.e., ethers, an aldehyde, a formamide, p-xylene, and alkanes), thus enabling the preparation of N-heteroarenes bearing various types of substituents.