80262-44-8

Basic information

• Product Name: CUCURBITURIL
• Synonyms: CUCURBITURIL;Cucurbituril[6];1H,4H,14H,17H-2,16:3,15-Dimethano-5H,6H,7H,8H,9H,10H,11H,12H,13H,18H,19H,20H,21H,22H,23H,24H,25H,26H-2,3,4a,5a,6a,7a,8a,9a,10a,11a,12a,13a,15,16,17a,18a,19a,20a,21a,22a,23a,24a,25a,26a-tetracosaazabispentaleno1,6:5,6,7cycloocta1,2,3:3,4pentaleno1,6:5,6,7c;Cucurbit[6]uril hydrate;Curcubit[6]uril;Cucurbit[6]uril (CB[6]) hydrate, 99+%;Cucurbit[6]uril hydrate contains acid of crystalization;cucurbit[6]uril
• CAS NO: 80262-44-8
• Molecular Formula: C₃₆H₃₆N₂₄O₁₂
• Molecular Weight: 996.82
• Product Categories: Chelation/Complexation Compounds;Others;Synthetic Reagents;Amine-Functional Polymers;Chelation/Complexation Compounds;Chemical Synthesis;Hydrophilic Polymers;Materials Science;Polymer Science;Polymers;Synthetic Reagents
• Mol File: 80262-44-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: ~470 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: white/solid
• Density: 2.66g/cm³
• Refractive Index: 2.341
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.02±0.20(Predicted)
• BRN: 4933186
• CAS DataBase Reference: CUCURBITURIL(CAS DataBase Reference)
• NIST Chemistry Reference: CUCURBITURIL(80262-44-8)
• EPA Substance Registry System: CUCURBITURIL(80262-44-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 80262-44-8(Hazardous Substances Data)

Usage

General Description

Cucurbituril is a family of complex molecules that are part of the larger class of compounds known as macrocyclic hosts. These hollow, pumpkin-shaped molecules exhibit unique properties because of their capability to form host-guest complexes with a wide range of compounds. This function allows them to capture and contain other molecules, which have applications in numerous scientific fields, such as drug delivery, molecular switching, and supramolecular chemistry. Cucurbiturils are highly selective and stable, and their structures can be manipulated and controlled for a particular function. Their extraordinary chemistry, combined with the ability to tailor their structures, makes them useful in many different biochemical applications.

InChI:InChI=1/C36H36N24O12/c61-25-37-1-38-14-16-42(26(38)62)4-46-18-20-50(30(46)66)8-54-22-24-58(34(54)70)11-57-23-21-53(33(57)69)7-49-19-17-45(29(49)65)3-41(25)15-13(37)39-2-40(14)28(64)44(16)6-48(18)32(68)52(20)10-56(22)36(72)60(24)12-59(23)35(71)55(21)9-51(19)31(67)47(17)5-43(15)27(39)63/h13-24H,1-12H2/t13-,14+,15+,16-,17-,18+,19+,20-,21-,22+,23+,24-

Upstream product

• 280774-26-7 C₅H₁₃N*C₃₆H₃₆N₂₄O₁₂ 
• 50-00-0 formaldehyd 
• 496-46-8 glycouril 
• 101241-21-8 3a,6a-diphenylglycoluril 
• 848440-50-6 glycoluril dimer 
• 950526-89-3 glycoluril tetramer 
• 950526-90-6 C₂₈H₃₀N₂₀O₁₀ 
• 496-46-8 glycoluril 
• 462-95-3 formaldehyde diethyl acetal 

Downstream Products

• 462-94-2 1,5-diaminopentane 

Relevant articles and documents

Synthesis of Disubstituted Cucurbit[6]uril and Its Rotaxane Derivative

(Matrix Presented) Synthesis of diphenyl cucurbit[6]uril (CB[6]) has been achieved via co-oligomerization of diphenyl glycoluril and unsubstituted glycoluril. The unsymmetrically substituted CB[6], Ph2CB[B], was further converted to a rotaxane incorporating bis(dinitrophenyl)spermine.

PROCESS FOR THE PREPARATION OF CUCURBITURIL DERIVATIVES

This invention relates to cucurbituril and/or one or more derivatives thereof with low formaldehyde content, to a process of manufacturing said cucurbituril and/or one or more derivatives thereof and to the use of said cucurbituril and/or one or more derivatives thereof, in particular in consumer and industrial products, and in industrial processes.

Cucurbit[n]uril formation proceeds by step-growth cyclo-oligomerization

In contrast to the high yield formation of cucurbit[n]uril (CB[n]) from a 1:2 ratio of glycoluril to formaldehyde, the condensation of glycoluril with less than 2 equiv of formaldehyde delivers a reaction mixture that contains glycoluril oligomers (2-6) and CB[n] compounds that lack one or more methylene bridges known as nor-seco-cucurbit[n]urils (ns-CB[n]). In this paper we report the chromatographic purification of C-shaped glycoluril oligomers (dimer-hexamer), their characterization in solution, and their X-ray crystal structures. Quite interestingly, despite being acyclic glycoluril pentamer 5 and hexamer 6 retain the ability to bind to guests typical of CB[6] but are also able to expand their cavity to accommodate larger guests like cationic adamantane derivatives. We performed product resubmission experiments with glycoluril oligomers 2-6 and found preferences for the formation of specific ring sizes during CB[n] formation. A comprehensive mechanistic scheme is proposed that accounts for the observed formation of 2-6 and ns-CB[n]. Overall, the experiments establish that a step-growth cyclo-oligomerization process operates during CB[n] formation.