6963-32-2

Usage

Uses

Used in Synthetic Chemistry:
2,3-dibromopropylammonium bromide is used as a reagent for the synthesis of azetidine rings attached to secondary amines. It facilitates the formation of these rings through a strain-release amination process, which is a valuable method for constructing complex molecular structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3-dibromopropylammonium bromide is used as a key intermediate in the synthesis of various drug molecules. Its ability to form azetidine rings with secondary amines makes it a valuable tool for the development of new pharmaceutical compounds with potential therapeutic applications.
Used in Research and Development:
2,3-dibromopropylammonium bromide is utilized in research and development settings to explore new synthetic pathways and methodologies. Its unique reactivity and ability to generate "spring loaded" electrophiles make it an attractive candidate for studying novel chemical reactions and mechanisms.

InChI:InChI=1/C3H7Br2N/c4-1-3(5)2-6/h3H,1-2,6H2

Upstream product

• 107-11-9 1-amino-2-propene 
• 106-98-9 1-butylene 
• 78888-18-3 N-tert-butoxycarbonylprop-2-en-1-amine 

Downstream Products

• 156697-67-5 (2,3-Dibromo-propyl)-[1-p-tolyl-meth-(E)-ylidene]-amine 
• 19540-05-7 1-azabicyclo<1.1.0>butane 
• 188818-01-1 N-benzylidene-2,3-dibromopropylamine 
• 244088-62-8 2-(bromomethyl)-1-(4-methylbenzenesulfonyl)aziridine 
• 302355-79-9 4-(azetidin-3-yl)morpholine 
• 160676-82-4 C₁₆H₁₆BrN 
• 5120-12-7 1-Benzenesulfonyl-2-(bromomethyl)ethylenimine 
• 50487-77-9 N-(2,3-dibromopropyl)benzamide 
• 156697-66-4 N-benzylidene-2,3-dibromopropan-1-amine 
• 156697-72-2 2,3-dibromo-N-(4-chlorobenzylidene)propan-1-amine 

Relevant academic research and scientific papers

Strain-Release-Driven Homologation of Boronic Esters: Application to the Modular Synthesis of Azetidines

Azetidines are important motifs in medicinal chemistry, but there are a limited number of methods for their synthesis. Herein, we present a new method for their modular construction by exploiting the high ring strain associated with azabicyclo[1.1.0]butane. Generation of azabicyclo[1.1.0]butyl lithium followed by its trapping with a boronic ester gives an intermediate boronate complex which, upon N-protonation with acetic acid, undergoes 1,2-migration with cleavage of the central C-N bond to relieve ring strain. The methodology is applicable to primary, secondary, tertiary, aryl, and alkenyl boronic esters and occurs with complete stereospecificity. The homologated azetidinyl boronic esters can be further functionalized through reaction of the N-H azetidine, and through transformation of the boronic ester. The methodology was applied to a short, stereoselective synthesis of the azetidine-containing pharmaceutical, cobimetinib.

SOLID FORMS OF 3-((1R,3R)-1-(2,6-DIFLUORO-4-((1-(3-FLUOROPROPYL)AZETIDIN-3-YL)AMINO)PHENYL)-3-METHYL-1,3,4,9-TETRAHYDRO-2H-PYRIDO[3,4-B]INDOL-2-YL)-2,2-DIFLUOROPROPAN-1-OL AND PROCESSES FOR PREPARING FUSED TRICYCLIC COMPOUNDS COMPRISING A SUBSTITUTED PHENYL OR PYRIDINYL MOIETY, INCLUDING METHODS OF THEIR USE

Provided herein are solid forms, salts such as compound B, and formulations of 3-((lR,3R)-l-(2,6-difluoro-4-((l-(3-fluoropropyl) azetidin-3-yl)amino)phenyl)-3-methyl-l,3,4,9-tetrahydro-2H- pyrido[3,4-b]indol-2-yl)-2,2-difluoropropan-l-ol, processes and synthesis thereof, and methods of their use in the treatment of cancer.

An improved, gram-scale synthesis of protected 3-haloazetidines: Rapid diversified synthesis of azetidine-3-carboxylic acids

Azetidines are increasingly important heterocycles found in a variety of natural products and pharmaceutical compounds. Protected 3-haloazetidines, widely used and versatile building blocks in medicinal chemistry, have been prepared in a one-pot, gram-scale strain-release reaction of 1-azabicyclo[1.1.0]butane from commercially available starting materials. These intermediates were subsequently used to prepare a series of high value azetidine-3-carboxylic acid derivatives including the first reported synthesis of 1-(tert-butoxy-carbonyl)-3-((trifluoromethyl)thio)azetidine-3-carboxylic acid. (Figure pressented)

Method for synthetizing Tebipenem intermediate

The invention discloses a method for synthetizing a Tebipenem intermediate, and belongs to the field of chemical pharmacy. 2- methylthio-4, 5- thiazoline is synthetized by using ethanolamine as a raw material, a disulfide bond and a C-N coupling and breaking disulfide bond are formed through addition, cyclization, open loop and hydrolysis by using allyl amine as a raw material, and finally the Tebipenem intermediate namely 1- ( 4,5- thiazoline -2- base) azetidine -3- mercaptide hydrochloride is synthetized. The method disclosed by the invention is simple and easy to operate, high in yield, low in pollution and suitable for industrial production.

Carbonic anhydrase II as host protein for the creation of a biocompatible artificial metathesase

An artificial metathesase results from incorporation of an Hoveyda-Grubbs catalyst bearing an arylsulfonamide anchor within human carbonic anhydrase II. The optimization of the catalytic performance is achieved upon combining both chemical and genetic means. Up to 28 TONs were obtained within four hours under aerobic physiological conditions.

Ring opening reactions of 1-arenesulfonyl-2-(bromomethyl)aziridines

The reactivity of 1-arenesulfonyl-2-(bromomethyl)aziridines with respect to lithium dialkylcyanocuprates and lithium dialkylcuprates (Gilman reagents) has been evaluated for the first time, pointing to the conclusion that these substrates can be applied successfully as synthetic equivalents for the 2-aminopropane dication synthon towards 2-alkylaziridines and α-branched N-tosylamides in good yields.

Improved synthesis of an energetic material, 1,3,3-trinitroazetidine exploiting 1-azabicyclo [1.1.0]Butane

Expeditious synthesis of 1-nitroso-3-nitroazetidine (6), a useful key intermediate for the synthesis of 1,3,3-trinitroazetidine (4), was investigated by using 1-azabicyclo[1.1.0]butane (3) and NaNO2 in the presence of some acids. The most efficient method was achieved in 26% yield by treatment of 3 with NaNO2 in the presence of H2SO4. Conversion of 6 into 4 was also carried out.

Novel efficient synthesis of 1-azabicyclo[1.1.0]butane and its application to the synthesis of 1-(1,3-thiazolin-2-yl)azetidine-3-thiol useful for the pendant moiety of an oral 1β-methyicarbapenem antibiotic L- 084

1-Azabicyclo[1.1.0]butane 2 was successfully synthesized by treatment of 2,3dibromopropylamine hydrobromide 4 with organolithium compounds and was readily converted to 1-(1,3-thiazolin-2-yl)azetidine-3-thiol hydrochloride 1 and versatile azetidine derivatives 9 and 10.

Preparation of (+)- and (-)-2,3-Dibromo-1-propanols

The enantiomers of 2,3-dibromo-1-propanol were obtained by diazotization of the diastereomeric d-tartrate salts of 2,3-dibromopropylamine.The products of the reaction contained approximately 13percent of the secondary alcohol 1,3-dibromo-2-propanol which was separated by either column chromatography on silica gel or preparative GLC to obtain the primary alcohols (+)-2,3-dibromo-1-propanol (26D +13.8 deg) and (-)-2,3-dibromo-1-propanol (24D -12.8 deg).NMR and EI mass spectra of the primary and secondary dibromopropanols clearly distinguished the structuralisomers from one another.The optical isomers will be used to examine possible stereoselective differences in mutagenic potency, since 2,3-dibromo-1-propanol is a mutagenic metabolite of the potent mutagen and carcinogen tris(2,3-dibromopropyl) phosphate.

Components of the Green Deathcap Toadstool Amanita phalloides, LVIII. - Some Dithiolanes Derived from Ketophalloidin as Reagents in Biochemical Research

Ketophalloidin (2), obtained from phalloidin (1) by oxidation with periodate, was transformed into the dithiolanecarboxylic acid 3 by reaction with 2,3-dimercaptopropionic acid, and into the (aminomethyl)dithiolane 4 by reaction with 3-amino-1,2-propanedithiol.Compound 4 was the starting material for the following derivatives: the N-(3-carboxypropionyl) compound 5, the N-iodoacetyl compound 6 and, by nucleophilic substitution of iodide by azide, for the azidoacetyl compound 8.A fluorescent phallotoxin (7) was obtained by reaction of 4 with fluorescein isothiocyanate.All phallotoxins described in this paper specifically bind, like phalloidin, to the receptor protein actin.Derivatives 6 and 7, as radioactively labeled molecules, are suitable for a covalent fixation to actin (affinity labeling); the functional derivatives 3,4 and 5 have been conjugated to bovine serum albumin, and the amino compound 4 has been covalently attached to activated sepharose in order to generate an adsorbent for affinity chromatography