100944-14-7

Basic information

• Product Name: (1S,4S)-2,5-DIAZABICYCLO[2.2.1]HEPTANE DIHYDROBROMIDE
• Synonyms: (1S,4S)- 2,5-DIAZABICYCLO[2.2.1]HEPTANE 2 HBR;2,5-Diazabicyclo[2.2.1]heptane, hydrobromide (1:2)
• CAS NO: 100944-14-7
• Molecular Formula: 2BrH*C₅H₁₀N₂
• Molecular Weight: 259.97
• Mol File: 100944-14-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 261.8 °C at 760 mmHg
• Flash Point: 112.1 °C
• Appearance: /
• CAS DataBase Reference: (1S,4S)-2,5-DIAZABICYCLO[2.2.1]HEPTANE DIHYDROBROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4S)-2,5-DIAZABICYCLO[2.2.1]HEPTANE DIHYDROBROMIDE(100944-14-7)
• EPA Substance Registry System: (1S,4S)-2,5-DIAZABICYCLO[2.2.1]HEPTANE DIHYDROBROMIDE(100944-14-7)

Safety Data

• Hazardous Substances Data: 100944-14-7(Hazardous Substances Data)

Usage

General Description

(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide, also known as DHβE, is a chemical compound with potential pharmaceutical applications. It is a potent and selective antagonist of the α4β2 nicotinic acetylcholine receptor, which plays a key role in nicotine addiction. DHβE has been studied for its potential use in smoking cessation therapies and as a tool in neuroscience research to understand the role of nicotinic acetylcholine receptors in various physiological and pathological conditions. The compound has also been investigated for its potential as an analgesic and as a treatment for nicotine dependence. DHβE is commonly used in research settings to study the effects of nicotinic acetylcholine receptor antagonism on behavior and neurochemistry.

Upstream product

• 100944-15-8 (1S,4S)-2-Benzyl-2,5-diazabicyclo<2.2.1>heptane dihydrobromide 
• 5234-72-0 (1S,4S)-5-Benzyl-2-tosyl-2,5-diazabicyclo<2.2.1>heptane 

Downstream Products

• 1032278-89-9 (1S,4S)-2,5-bis[2-(2-hydroxyphenyl)acetyl]diazabicyclo[2.2.1]heptane 

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.