132723-93-4

Basic information

• Product Name: 1-Benzyl-1,4,8,11-tetraazacyclotetradecane
• Synonyms: 1-Benzyl-1,4,8,11-tetraazacyclotetradecane;N-Benzyl-1,4,8,11-tetraazacyclotetradecane, min. 98%;N-Benzyl-1,4,8,11-tetraazacyclotetradecane,Min.98%;1,4,8,11-Tetraazacyclotetradecane, 1-(phenylMethyl)-;N-Benzylcyclam;Mono-N-Benzyl-Cyclam
• CAS NO: 132723-93-4
• Molecular Formula: C₁₇H₃₀N₄
• Molecular Weight: 290.45
• Product Categories: organic amine
• Mol File: 132723-93-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 434.3°Cat760mmHg
• Flash Point: 226.4°C
• Appearance: white to yellow/Powder
• Density: 0.949g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.493
• Sensitive: Hygroscopic
• CAS DataBase Reference: 1-Benzyl-1,4,8,11-tetraazacyclotetradecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyl-1,4,8,11-tetraazacyclotetradecane(132723-93-4)
• EPA Substance Registry System: 1-Benzyl-1,4,8,11-tetraazacyclotetradecane(132723-93-4)

Safety Data

• Hazardous Substances Data: 132723-93-4(Hazardous Substances Data)

Usage

General Description

1-Benzyl-1,4,8,11-tetraazacyclotetradecane, also known as cyclam, is a chemical compound that belongs to the class of macrocyclic compounds. It is a large, cyclic molecule containing four nitrogen atoms that form a tetraazacyclotetradecane ring structure. The benzyl group attached to the molecule provides it with a unique structure and chemical properties. Cyclam is commonly used in coordination chemistry and as a chelating agent for metal ions, due to its ability to form stable complexes with a variety of metal ions. It has also been studied for potential applications in medical imaging, drug delivery, and catalysis. Cyclam is a versatile compound with potential for a wide range of applications in the fields of chemistry and biotechnology.

InChI:InChI=1/C17H30N4/c1-2-6-17(7-3-1)16-21-14-5-10-19-12-11-18-8-4-9-20-13-15-21/h1-3,6-7,18-20H,4-5,8-16H2

Upstream product

• 295-37-4 1,4,8,11-Tetraazacyclotetradecane 
• 100-39-0 benzyl bromide 
• 439211-82-2 cis-10b-methyldecahydro-3a,5a,8a,10a-tetraazapyrene 
• 170161-27-0 1,4,8-tris(tert-butoxycarbonyl)-1,4,8,11-tetraazacyclotetradecane 
• 4741-99-5 3,7-diazanonane-1,9-diamine 
• 439211-80-0 cis-9a-methyloctahydro-1H,4H,7H-1,3a,6a,9-tetraazaphenalene 
• 74199-16-9 cis-4,7,11,14-tetraazaperhydropyrene 
• 98-88-4 benzoyl chloride 
• 80799-52-6 Cyclamphosphine oxide 

Downstream Products

• 176252-17-8 Mo(CO)3(C₁₀H₂₃N₄(CH₂C₆H₅)) 
• 578737-58-3 Co⁽²⁺⁾*(C₃H₆)2(C₂H₄)2N₄H₃CH₂C₆H₅*NO₃^(1-)*PF₆^(1-)=[Co((C₃H₆)2(C₂H₄)2N₄H₃CH₂C₆H₅)(NO₃)]PF₆ 
• 578737-62-9 Cd⁽²⁺⁾*(C₃H₆)2(C₂H₄)2N₄H₃CH₂C₆H₅*NO₃^(1-)*PF₆^(1-)=[Cd((C₃H₆)2(C₂H₄)2N₄H₃CH₂C₆H₅)(NO₃)]PF₆ 
• 578737-63-0 [Pb((C₃H₆)2(C₂H₄)2N₄H₃CH₂C₆H₅)(NO₃)2] 

Relevant articles and documents

Regioselective N-functionalization of tetraazacycloalkanes

Bisaminal type compounds obtained by condensation of pyruvic aldehyde with the suitable open-chain tetraamine followed by cyclization with either dibromoethane or dibromopropane can be regioselectively quaternized by a wide range of alkylating agents. Removal of the bisaminal bridge yields the monosubstituted tetraazamacrocycle or bismacrocycle. Further functionalization allows the preparation of bifunctional ligands or trisubstituted macrocycles. The structure of six compounds was solved by X-ray diffraction, and the unexpected results are rationalized according to the molecular modeling calculations.

A convenient method for the preparation of mono N-alkylated cyclams and cyclens in high yields

Selective and high yield synthesis of mono N-substituted derivatives of cyclam and cyclen can be achieved by using a direct and general synthetic method with very mild reaction conditions.

Crystal structures and reactivity of 3a,5a,8a,10a-tetraazaperhydropyrene derivatives. An alternative approach to selective nitrogen alkylation of 1,4,8,11-tetraazacyclotetradecane (cyclam)

1-Alkyl and 1,8-dialkyl-1,4,8,11-tetraazacyclotetradecanes (alkyl = benzyl or methyl) were synthesised through cis-aminal of cyclam which was obtained by reaction of glyoxal and cyclam. The corresponding trans-aminal was synthesised from the respective li