74725-77-2

Basic information

• Product Name: 1-iodopentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane
• Synonyms: Iodocubane
• CAS NO: 74725-77-2
• Molecular Formula: C₈H₇I
• Molecular Weight: 230.0456
• Mol File: 74725-77-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 234.6°C at 760 mmHg
• Flash Point: 120.5°C
• Density: 2.5g/cm³
• Vapor Pressure: 0.0801mmHg at 25°C
• Refractive Index: 1.87
• CAS DataBase Reference: 1-iodopentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-iodopentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane(74725-77-2)
• EPA Substance Registry System: 1-iodopentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane(74725-77-2)

Safety Data

• Hazardous Substances Data: 74725-77-2(Hazardous Substances Data)

Usage

Molecular structure

Pentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane derivative with an iodine atom The compound features a complex, unique structure based on a pentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane core with an iodine atom attached to one of the carbon atoms.

Synthetic compound

Not found in nature 1-iodopentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane is not a naturally occurring compound and must be synthesized in a laboratory.

Potential applications

Organic synthesis and chemical research Due to its intricate structure and potentially unique reactivity, the compound may have applications in these fields, although more research is needed to confirm its benefits.

Challenges

Synthesis and handling The complex nature of 1-iodopentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane may present difficulties in its synthesis and handling, requiring specialized techniques and equipment.

Ongoing research

Properties and potential uses Studies on 1-iodopentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane are still ongoing, and further research is needed to fully understand its characteristics and potential benefits.

Upstream product

• 277-10-1 cubane 
• 53578-15-7 cubane-1-carboxylic acid 
• 60462-14-8 Cubancarbonsaeurechlorid 
• 97229-08-8 1,4-diiodocubane 
• 79-37-8 oxalyl dichloride 
• 3811-73-2 2-mercaptopyridine-1-oxide sodium salt 

Downstream Products

• 97229-08-8 1,4-diiodocubane 

Relevant articles and documents

The cubane paradigm in bioactive molecule discovery: Further scope, limitations and the cyclooctatetraene complement

The cubane phenyl ring bioisostere paradigm was further explored in an extensive study covering a wide range of pharmaceutical and agrochemical templates, which included antibiotics (cefaclor, penicillin G) and antihistamine (diphenhydramine), a smooth muscle relaxant (alverine), an anaesthetic (ketamine), an agrochemical instecticide (triflumuron), an antiparasitic (benznidazole) and an anticancer agent (tamibarotene). This investigation highlights the scope and limitations of incorporating cubane into bioactive molecule discovery, both in terms of synthetic compatibility and physical property matching. Cubane maintained bioisosterism in the case of the Chagas disease antiparasitic benznidazole, although it was less active in the case of the anticancer agent (tamibarotenne). Application of the cyclooctatetraene (COT) (bio)motif complement was found to optimize benznidazole relative to the benzene parent, and augmented anticancer activity relative to the cubane analogue in the case of tamibarotene. Like all bioisosteres, scaffolds and biomotifs, however, there are limitations (e.g. synthetic implementation), and these have been specifically highlighted herein using failed examples. A summary of all templates prepared to date by our group that were biologically evaluated strongly supports the concept that cubane is a valuable tool in bioactive molecule discovery and COT is a viable complement.

Halogenation of cubane under phase-transfer conditions: Single and double C - H-bond substitution with conservation of the cage structure

The first highly selective C - H chlorination, bromination, and iodination of cubane (1) utilizing polyhalomethanes as halogen sources under phase-transfer (PT) conditions is described. Isomeric dihalocubanes with all possible combinations of chlorine, bromine, and iodine in ortho, meta, and para positions were also prepared by this method; m-dihalo products form preferentially. Ab initio and density functional theory (DFT) computations were used to rationalize the pronounced differences in the reactions of 1 with halogen (Hal·) vs carbon-centered trihalomethyl (Hal3C·) radicals (Hal = Cl, Br), For Hal3C radicals the C - H abstraction pathway is less unfavorable (ΔG?298 = 21.6 kcal/mol for C3C· and 19.4 kcal/mol for Br3C· at B3LYP/6-311+G**//B3LYP/6-31G**) than the fragmentation of the cubane skeleton via SH2-attack on one of the carbon atoms of 1 (ΔG?298 = 33.8 and 35.1 kcal/mol, respectively). In stark contrast, the reaction of 1 with halogen atoms preferentially follows the fragmentation pathway (ΔG?298 = 2.1 and 7.5 kcal/mol) and C - H abstraction is more unfavorable (ΔG?298 = 4.6 and 12.0 kcal/mol). Our computational results nicely agree with the behavior of 1 under PT halogenation conditions (where Hal3C· is involved in the activation step) and under free-radical photohalogenation with Hal2 (Della E. W., et al. J. Am. Chem. Soc. 1992, 114, 10730). The incorporation of a second halogen atom preferentially in the meta position of halocubanes demonstrates the control of the regioselectivity by molecular orbital symmetry.

Initiation and bonding of diamond and other thin films

A method for initiating and bonding thin films on substrates is described. The method employs an interlayer comprising a self-assembling monolayer (SAM). The SAM is formed from monomers, one end of which are capable of bonding to the substrate, and the other end of which form a surface similar to, and capable of initiating the formation of a film. Additionally, compositions for monomers, methods for SAM formation, and methods for film formation are disclosed. In a preferred embodiment the thin film is comprised of diamond.