10303-95-4

Basic information

• Product Name: 1,3-Adamantanediamine
• Synonyms: 1,3-Diaminoadamantane;1,3-Adamantanediamine;Tricyclo[3.3.1.13,7]decane-1,3-diamine;4. 1,3-diaminoadamantane;(3-amino-1-adamantyl)amine dihydrochloride;Tricyclo(3.3.1.1(sup 3,7))decane-1,3-diamine, dihydrochloride
• CAS NO: 10303-95-4
• Molecular Formula: C₁₀H₁₈N₂
• Molecular Weight: 166.26
• Mol File: 10303-95-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 249 °C
• Flash Point: 122 °C
• Appearance: /
• Density: 1.153
• Vapor Pressure: 0.0241mmHg at 25°C
• Refractive Index: 1.597
• PKA: 10.73±0.40(Predicted)
• CAS DataBase Reference: 1,3-Adamantanediamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Adamantanediamine(10303-95-4)
• EPA Substance Registry System: 1,3-Adamantanediamine(10303-95-4)

Safety Data

• Hazardous Substances Data: 10303-95-4(Hazardous Substances Data)

Usage

Uses

1,3-Adamantanediamine is used in preparation method of SSZ-13 molecular sieve from β molecular sieve.

Preparation

1,3-Adamantanediamine synthesis: 1,3-Adamantane dicarboxylic acid (12 g) was mixed with 50 mL of SOCl2 and the mixture was refluxed for 3 h. Excessive SOCl2 was evaporated and 1,3-adamantane dicarbonyl dichloride was obtained as white solid, dissolved in dried benzene and added to cold ammonia solution slowly, during which a white precipitate was formed gradually filtered and then washed the precipitate several times with water to give 1,3-disaminoacyladamantane as white solid, recrystallized from ethanol. White solid, yield 10.58 g (89 %).

Purification Methods

Purify it by zone refining. The dibenzoyl derivative has m 248o, and the dihydrochloride salt has m 310o (360o) after recrystallisation from aqueous EtOH or EtOH/Et2O. [Prelog & Seiwerth Chem Ber 74 1769 1941, Stetter & Wulff Chem Ber 93 1366 1960.]

InChI:InChI=1/C10H18N2/c11-9-2-7-1-8(4-9)5-10(12,3-7)6-9/h7-8H,1-6,11-12H2

Upstream product

• 62472-39-3 1,3-adamantane-dicarbonamide 
• 876-53-9 1,3-dibromoadamantane 
• 281-23-2 adamantane 
• 908245-26-1 1,3-diazidoadamantane 
• 59940-35-1 N,N'-(adamantane-1,3-diyl)diacetamide 

Downstream Products

• 55100-59-9 1,3-dinitroadamantane 
• 876-53-9 1,3-dibromoadamantane 
• 281-23-2 adamantane 
• 103307-81-9 N,N'-adamantane-1,3-diyl-bis-benzamide 

Relevant articles and documents

Efficient synthesis of 1,3-adamantanedicarboxylic acid and 1,3-diaminoadamantane

1,3-Adamantane dicarboxylic acid was efficiently synthesized from 1-adamantane carboxylic acid by one-pot method. 1,3- Diaminoadamantane was synthesized from 1,3-adamantane dicarboxylic acid via amidation reaction and Hofmann degradation. The structure was confirmed by NMR spectra, etc.

INHIBITORS OF CYCLIN-DEPENDENT KINASE 7 (CDK7)

The present invention provides novel compounds of Formula (I) and pharmaceutically acceptable salts, solvates, hydrates, tautomers, stereoisomers, isotopically labeled derivatives, and compositions thereof. Also provided are methods and kits involving the compounds or compositions for treating or preventing proliferative diseases (e.g., cancers (e.g., leukemia, melanoma, multiple myeloma), benign neoplasms, angiogenesis, inflammatory diseases, autoinflammatory diseases, and autoimmune diseases) in a subject. Treatment of a subject with a proliferative disease using a compound or composition of the invention may inhibit the aberrant activity of cyclin-dependent kinase (e.g., CDK7), and therefore induce cellular apoptosis and/or inhibit transcription in the subject.

Synthesis and characterization of 1,3-diaminoadamantane

A polycyclic diamine, 1,3-diaminoadamantane has been synthesized from adamantane using trifluoroacetic acid and urea with diphenyl ether as solvent.