125224-64-8

Basic information

• Product Name: (1R)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane dihydrobromide
• Synonyms: (1S,4S)-2-Methyl-2,5-diazabicyclo2.2.1heptanedihydrobromide;(1R)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane dihydrobromide;(1R,4R)-5-Methyl-2,5-diaz...;(1R,4R)-5-Methyl-2,5-diazabicyclo[2.2.1]heptane dihydrobroMide;(1R,4R)-2-methyl-2,5-diazabicyclo[2.2.1]heptane dihydrobromide
• CAS NO: 125224-64-8
• Molecular Formula: 2BrH*C₆H₁₂N₂
• Molecular Weight: 274
• Product Categories: Chiral
• Mol File: 125224-64-8.mol

Chemical Properties

• Melting Point: 220-225 °C
• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: (1R)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane dihydrobromide(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane dihydrobromide(125224-64-8)
• EPA Substance Registry System: (1R)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane dihydrobromide(125224-64-8)

Safety Data

• Hazardous Substances Data: 125224-64-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1R)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane dihydrobromide is used as a reactant in organic synthesis for the preparation of a wide range of pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure and reactivity make it a valuable intermediate in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (1R)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane dihydrobromide is used as a key intermediate in the synthesis of various drugs, particularly those targeting the central nervous system. Its ability to form a stable bicyclic structure allows for the development of molecules with specific biological activities.
Used in Agrochemical Industry:
(1R)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane dihydrobromide is also utilized in the agrochemical industry for the synthesis of pesticides and other crop protection agents. Its unique structure can be modified to create molecules with targeted pest control properties, contributing to the development of more effective and environmentally friendly agrochemicals.
Used in Research and Development:
In the field of research and development, (1R)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane dihydrobromide serves as a valuable compound for exploring new reaction pathways and understanding the fundamental principles of organic chemistry. Its unique structure and reactivity make it an ideal candidate for studying various chemical transformations and mechanisms.

InChI:InChI=1/C6H12N2.2BrH/c1-8-4-5-2-6(8)3-7-5;;/h5-7H,2-4H2,1H3;2*1H/t5?,6-;;/m1../s1

Upstream product

• 125109-58-2 (1S,4S)-2-(4-Tolylsulfonyl)-5-methyl-2,5-diazabicyclo<2.2.1>heptane 
• 125224-63-7 (1R,4R)-2-(4-Tolylsulfonyl)-5-methyl-2,5-diazabicyclo<2.2.1>heptane 
• 5234-75-3 (2S,4R)-1-(4-tolylsulfonyl)-4-<(4-tolylsulfonyl)oxy>-2-<<(4-tolylsulfonyl)oxy>methyl>pyrrolidine 
• 20275-18-7 N--trans-4-hydroxy-L-proline 
• 132666-67-2 (2S,4R)-ethyl 4-hydroxypyrrolidine-2-carboxylate 
• 116143-07-8 Ethyl (2R,4S)-4-Hydroxy-N-tosyl-2-pyrrolidinecarboxylate 
• 51-35-4 4R-4-hydroxyproline 
• 77449-99-1 (2R,4R)-2-ethoxycarbonyl-4-hydroxypyrrolidine hydrochloride 
• 116143-06-7 4-(acetyloxy)-1-<(4-methylphenyl)sulfonyl>-D-proline ethyl ester 
• 116143-08-9 (2R,4S)-2-(Hydroxymethyl)-4-hydroxy-1-(4-tolylsulfonyl)pyrrolidine 
• 125109-57-1 (2S,4R)-1-(4-Tolylsulfonyl)-2-(chloromethyl)-4-((4-tolylsulfonyl)oxy)pyrrolidine 
• 125109-57-1 (2R,4S)-1-(4-Tolylsulfonyl)-2-(chloromethyl)-4-((4-tolylsulfonyl)oxy)pyrrolidine 
• 116143-09-0 (3S,5R)-1-[(4-methylphenyl)sulfonyl]-3-[(4-methylphenyl)sulfonyloxy]-5-[(4-methylphenyl)sulfonyloxymethyl]pyrrolidine 
• 2584-71-6 cis-hydroxy-D-proline 

Downstream Products

• 767291-68-9 (1S,4S)-(+)-2,5-dimethyl-2,5-diazabicyclo[2.21]heptane 
• 1152113-38-6 4-chloro-5-fluoro-6-((1S,4S)-5-methyl-2,5-diazazbicyclo[2.2.1]hept-2-yl)-2(1H)-pyrimidinone hydrazone 
• 1152110-12-7 (1S,4S)-2-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-5-methyl-2,5-diazazbicyclo[2.2.1]heptane 
• 1182190-24-4 2-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl]-5-nitrotoluene 
• 1338705-94-4 2-chloro-3,4-bis((4-methoxybenzyl)oxy)-N-(((1S,4S)-2-methyl-2-azabicyclo[2.2.1]heptan-5-yl)methyl)benzamide 
• 1195780-48-3 6-[1-cyclobutyl-3-methyl-4-[[(1R,4R)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl]carbonyl]-1H-pyrazol-5-yl]-13-cyclohexyl-3-methoxy-N-[(1-methylethyl)sulfonyl]-7H-indolo[2,1-a][2]benzazepine-10-carboxamide 
• 1195780-68-7 C₄₂H₅₀N₆O₅S 
• 1182181-38-9 4-(6-(morpholin-4-yl)pyridin-3-yl)-N-(3-methyl-4-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl)pyrimidin-2-amine 
• 1182190-43-7 [3-methyl-4-((1S,4S)-2-methyl-2,5-diazabicyclo[2.2.1]heptan-5-yl)phenyl][N,N-bis(tert-butoxycarbonyl)]guanidine 
• 1182181-08-3 4-(6-(N,N-dimethylamino)pyridin-3-yl)-N-(3-methyl-4-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl)pyrimidin-2-amine 
• 1182190-51-7 4-(6-(chloro)pyridin-3-yl)-N-(3-methyl-4-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl)pyrimidin-2-amine 
• 1182190-21-1 3-methyl-4-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]aniline 

Relevant articles and documents

Synthesis of novel derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane and their evaluation as potential ligands in asymmetric catalysis

Thirty-seven (most of them novel) chiral derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane (2-36, 38, 39) were prepared from (S)-trans-4-hydroxyproline. A selection of these chiral ligands were examined as potential ligands in the preparation of catalysts for the enantioselective addition of diethylzinc to aldehydes and as chiral Lewis acid activators in the asymmetric Diels-Alder reaction. In the former system, diamine 30 induced up to 92 % enantiomeric excess in the formation of (S)-phenyl ethyl carbinol, whereas in the case of the cycloaddition reaction between cyclopentadiene and 3-acryloyloxazolidin-2-one the catalytic complex formed between dimeric derivative 8 and copper triflate [Cu(OTf)2] afforded the expected product in a 95:5 endo/exo ratio and up to 72 % ee for the major diastereomeric product. Finally, some of the novel chiral diamines prepared in this work were also evaluated as potential organocatalysts in the asymmetric amination of ethyl α-phenyl-α-cyano acetate. Bifunctional derivative 12 provided the animated product in excellent yield and with up to 40 % ee. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Preparation of 2,5-diazabicyclo[2.2.1]heptanes and intermediates

(R,R)-2,5-Diazabicyclo[ 2.2.1]heptanes are prepared from a compound of the formula STR1 wherein X and R2 are as defined herein, by heating with tosylchloride in pyridine, reacting the formed compound of the formula STR2 with a C1 -C6 alkylamine or ammonia, and reducing or hydrolyzing the formed compound of the formula STR3 wherein R1 is hydrogen or C1 -C6 alkyl.