tert-butyl N-{3-aminobicyclo[1.1.1]pentan-1-yl}carbamate

📋Basic Information

English translation: N-{3-Amino-2-cyclopenten-1-yl}carbamate tert-butyl ester
English name: tert-Butyl (3-aminobicyclo[1.1.1]pentan-1-yl)carbamate
CAS Number: 1638767-25-5
Molecular formula: C₁₀H₁₈N₂O₂
Molecular weight: 198.26 g/mol
MDL Number: MFCD27987307
Appearance: White to light yellow powder or crystals
Alternative names and structural features
This compound is also known as N1-Boc-dibenzocycloheptane-1,3-diamine, or 1-(Boc-amino) dibenzocycloheptane-3-amine.
The core structure of this molecule is a highly strained, sp³-carbon-rich bicyclo[1.1.1]pentane (BCP) framework. Additionally, the molecule contains a free amino group (-NH₂) and a Boc-protected amino group (-NH-Boc) simultaneously. This “one free and one protected” design gives it high selectivity and flexibility in the synthesis process.

💡Core properties

Physical properties:
Boiling point: Approximately 288.9 °C (at 760 mmHg).
Melting point: approximately 122 °C.
Density: Approximately 1.14 ± 0.1 g/cm³ (calculated value at 20 °C).
Flash point: Approximately 128.5 °C (calculated value).
Solubility: Slightly soluble in water (7.3 g/L at 25°C).
Computational properties:
LogP: Approximately 1.14.
Topological Polar Surface Area (TPSA): It is 64.35 Ų, which is a parameter used to measure the polarity of a molecule.
Hydrogen bond: Contains 2 hydrogen bond donors (-NH₂ and -NH-) and 3 hydrogen bond acceptors (N and O atoms)

📌Main Applications

Drug synthesis intermediates: As a crucial BCP bridging cyclization building block, they are used to synthesize a variety of active compounds, such as those that can be used to prepare tetrazole-based eIF2B (eukaryotic translation initiation factor 2B) activators. The BCP framework is often used as a bioelectronic equivalent of the benzene ring and is introduced into drug molecules to improve their physicochemical properties and metabolic stability.
PROTAC development: The rigid three-dimensional structure of the BCP framework also makes it an ideal linker construction unit for protein degradation targeting chimeras (PROTACs) in the development process, helping to optimize the conformation and performance of the molecule.

⚠️Operation and Safety Information

GHS Hazard Statement: Based on the safety data sheets provided by multiple suppliers, this substance is classified as hazardous and has the following risks:
H302: Harmful by ingestion.
H315: Causes skin irritation.
H319: Causes severe eye irritation.
H335: May cause respiratory irritation.
Precautionary statement: During operation, one should follow the basic laboratory safety guidelines:
P261: Avoid inhaling dust.
P280: Wear protective gloves / protective clothing / protective goggles.
P305 + P351 + P338: If it gets into your eyes, rinse them with water for a few minutes carefully. If you are wearing contact lenses and can easily remove them, remove them and continue rinsing.
P302 + P352: In case of skin contact, wash thoroughly with plenty of soap and water.
P403 + P233 + P235: Store in a well-ventilated area, keep the container sealed, and maintain low temperature.
Storage conditions:
Temperature: It is usually stored at a low temperature of 2-8°C. Some suppliers also accept storage at room temperature in a dark and low-temperature environment (<15°C), but it must be sealed under an inert gas (such as argon).
Long-term storage: If stored in powder form, it is recommended to keep it at -20°C for 3 years; if dissolved in a solvent, it can be stored at -80°C for 6 months.
Sensitivity: This compound is sensitive to air. It should be stored in a sealed container and protected from light to prevent deterioration.

Product Manager Email: Lucy@coreychem.com