22287-35-0

Basic information

• Product Name: bicyclo[1.1.1]pentan-1-aMine
• Synonyms: bicyclo[1.1.1]pentan-1-aMine;Bicyclo[1.1.1]pentan-1-aMine hydrochloride;Bicyclo[1.1.1]pent-1-ylamine hydrochloride;EOS-60771;BICYCLO[1.1.1]PENTAN-1-AMINE HYDROCHORIDE;bicyclo[1.1.1]pentan-3-amine
• CAS NO: 22287-35-0
• Molecular Formula: C₅H₉N*ClH
• Molecular Weight: 83.13166
• Product Categories: organic building block
• Mol File: 22287-35-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 242-244 °C
• Appearance: /
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Soluble in water
• CAS DataBase Reference: bicyclo[1.1.1]pentan-1-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: bicyclo[1.1.1]pentan-1-aMine(22287-35-0)
• EPA Substance Registry System: bicyclo[1.1.1]pentan-1-aMine(22287-35-0)

Safety Data

• Hazardous Substances Data: 22287-35-0(Hazardous Substances Data)

Usage

Description

Bicyclo[1.1.1]pentan-1-amine, also known as 1-bicyclo[1.1.1]pentylamine, is an organic compound with a unique bicyclic structure. It is a versatile building block in organic synthesis and possesses amine functional groups that enable various chemical reactions and interactions.

Uses

Used in Pharmaceutical Industry:
Bicyclo[1.1.1]pentan-1-amine is used as a precursor in the synthesis of a potent quinolone antibacterial agent, U-87947E, for the development of new antibiotics to combat bacterial infections.
Used in Chemical Synthesis:
Bicyclo[1.1.1]pentan-1-amine is used as a starting material to synthesize bisbicyclo[1.1.1]pentyldiazene, which can be further utilized in various chemical reactions and applications.
Used in Click Chemistry Applications:
Bicyclo[1.1.1]pentan-1-amine can be used to prepare bicyclo[1.1.1]pentane-derived azides, which are valuable intermediates in click chemistry. These azides can be employed in the synthesis of a wide range of compounds, including pharmaceuticals, bioconjugates, and materials, due to the high reactivity and selectivity of click chemistry reactions.

Upstream product

• 136863-38-2 1-azido-3-iodobicyclo<1.1.1>pentane 
• 1581682-03-2 biclyclo [1.1.1]pentyl-1-azide 
• 22287-28-1 bicyclo[1.1.1]pentane-1-carboxylic acid 

Downstream Products

• 1046861-46-4 Imidazole-1-carboxylic acid bicyclo[1.1.1]pent-1-ylamide 
• 1403865-19-9 ethyl 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxylate 
• 1403864-84-5 2-(bicyclo[1.1.1]pentan-1-ylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)pyrimidine-5-carbonitrile 

Relevant articles and documents

Bicyclo[1.1.1]pentane-Derived Building Blocks for Click Chemistry

Syntheses of bicyclo[1.1.1]pentane-derived azides and terminal alkynes – interesting substrates for click reactions – are described. With a few exceptions, these compounds were prepared in two or three steps starting from common synthetic intermediates – the corresponding carboxylic acids. The key step in the synthesis of 1-azidobicyclo[1.1.1]pentanes is a copper-catalysed diazo-transfer reaction with imidazole-1-sulfonyl azide. The preparation of bicyclo[1.1.1]pentyl-substituted alkynes relies on a Seyferth–Gilbert homologation with dimethyl 1-diazo-2-oxopropylphosphonate (Ohira–Bestmann reagent). Both types of target compounds were found to be suitable substrates for click reactions, and thus they are promising building blocks for medicinal, combinatorial and bioconjugate chemistry. A practically important side result of this study was a multigram preparation of Boc-monoprotected 1,3-diaminobicyclo[1.1.1]pentane – a representative bicyclic conformationally restricted diamine derivative.

PROPELLANE DERIVATES AND SYNTHESIS

Disclosed herein are compounds of the general Formula (I), and methods of synthesizing substituted bicyclo[1.1.1 jpentanes. The synthetic methods described herein use a [1.1.1]propellane, a Group VIII transition metal compound, a hydride source and a reagent that can contribute a substituent to form a substituted bicycIo[1.1.1 ]pentane, such as a compound of the general Formula (I).

A new route to bicyclo[1.1.1]pentan-1-amine from 1-azido-3-iodobicyclo[1.1. 1]pentane

From a medicinal chemistry perspective, bicyclo[1.1.1]pentan-1-amine (1) has served as a unique and important moiety. Synthetically, however, this compound has received little attention, and only one scalable route to this amine has been demonstrated. Reduction of an easily available and potentially versatile intermediate, 1-azido-3-iodobicyclo[1.1.1]pentane (2), can offer both a flexible and scalable alternative to this target. Herein, we describe our scrutiny of this reportedly elusive transformation and report our ensuing success with this endeavor.