132747-20-7

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;(1S,4S)-(+)-2,5-DIAZABICYCLO[2.2.1]HEPTANE DIHYDROBROMIDE;(1S,4S)-2,5-DIAZABICYCLO[2.2.1]HEPTANE DIHYDROBROMIDE;(1S,2S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide;(1S,4S)-2,5-DIAZABICYLO[2.2.1]HEPTANE DIHYDROBROMIDE;(1S,4S)-2,5-DIAZABICYCLO[2.2.1]HEPTANE DIHYDROBROMIDE 97+%;(1S,2S)-2,5-Diazabicyclo2.2.1üheptane dihydrobromide, 98%
• CAS NO: 132747-20-7
• Molecular Formula: 2BrH*C₅H₁₀N₂
• Molecular Weight: 259.97
• EINECS: -0
• Product Categories: Chiral
• Mol File: 132747-20-7.mol

Chemical Properties

• Melting Point: 300 °C (dec.)(lit.)
• Boiling Point: 261.8 °C at 760 mmHg
• Flash Point: 112.1 °C
• Appearance: /
• Vapor Pressure: 0.00765mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• Sensitive: Hygroscopic
• BRN: 4258260
• 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(132747-20-7)
• EPA Substance Registry System: (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide(132747-20-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 132747-20-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is used as a reagent for the synthesis and characterization of new piperazine-type inhibitors for mitochondrial ubiquinone reductase, which are useful in the treatment of CXCR4-mediated diseases.
Used in Chemical Synthesis:
(1S,4S)-(+)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is used as a starting material for the synthesis of chiral diazabicyclic ligands, applicable in the preparation of dicopper(II) complexes.
Used in Catalyst Preparation:
(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is used as a precursor in the preparation of diazabicyclo[2.2.1]heptane derivatives as catalysts, which are applicable in asymmetric catalysis reactions.
Used in Organic Chemistry:
(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is used as an organocatalyst in the Biginelli reaction of aromatic aldehydes with ethyl acetoacetate and urea, facilitating the synthesis of heterocyclic compounds.

InChI:InChI=1/C5H10N2.2BrH/c1-4-2-6-5(1)3-7-4;;/h4-7H,1-3H2;2*1H

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.