59346-69-9

Basic information

• Product Name: 1-bromopentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane
• Synonyms: 1-Bromocubane; Bromocubane; pentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane, 1-bromo-
• CAS NO: 59346-69-9
• Molecular Formula: C₈H₇Br
• Molecular Weight: 183.0452
• Mol File: 59346-69-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 204.1°C at 760 mmHg
• Flash Point: 59.1°C
• Density: 2.436g/cm³
• Vapor Pressure: 0.383mmHg at 25°C
• Refractive Index: 1.969
• CAS DataBase Reference: 1-bromopentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-bromopentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane(59346-69-9)
• EPA Substance Registry System: 1-bromopentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane(59346-69-9)

Safety Data

• Hazardous Substances Data: 59346-69-9(Hazardous Substances Data)

Usage

Explanation

Different sources of media describe the Explanation of 59346-69-9 differently. You can refer to the following data:
1. A bicyclic compound is a type of organic molecule that contains two rings of carbon atoms. In this case, the compound has two fused rings.
3. Bromine Atom Attachment
2. The bromine atom is attached to one of the carbon atoms in the molecule, which can be used for further chemical reactions and modifications.
4. Organic Synthesis
3. The compound is used in organic synthesis, which is the process of creating new organic compounds by forming or breaking chemical bonds.
5. Building Block in Pharmaceutical Production
4. It serves as a building block or intermediate in the production of various pharmaceuticals and fine chemicals, which are used in the development of drugs and other chemical products.
6. Reagent in Chemical Reactions
5. The compound can be used as a reagent to introduce a bromine atom into other organic compounds, which can be useful for creating new molecules with specific properties.
7. Versatile Compound
6. Due to its unique structure and properties, 1-bromopentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane is a versatile compound that can be used in various applications in the field of organic chemistry.
8. Importance in New Molecule and Material Development
7. The compound plays a significant role in the development of new molecules and materials, as it can be used as a starting point for creating a wide range of organic compounds with different properties and applications.

Upstream product

• 277-10-1 cubane 
• 60462-14-8 Cubancarbonsaeurechlorid 
• 53578-15-7 cubane-1-carboxylic acid 

Downstream Products

• 59346-70-2 1,4-dibromocubane 

Relevant articles and documents

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.

Synthesis of Bridgehead Halides by Barton Halodecarboxylation

Bridgehead carboxylic acids can be converted into their corresponding chlorides very efficiently under Barton halodecarboxylation conditions.Addition of the acid chloride to a suspension of the sodium salt of 1-hydroxypyridine-2(1H)-thione in boiling carbon tetrachloride under irradiation leads to excellent yields of the bridgehead chloride via the derived thiohydroxamic ester.In a useful modification for the synthesis of volatile halides, either 1,1,1-trichloro-2,2,2-trifluoroethane or trichlorofluoromethane can be employed as substitute solvents.It is found that the Barton procedure is applicable to the synthesis of labile bromides such as 1-bromobicycloheptane for which the usual Hunsdiecker reaction fails.For these, and other brominations, 2-bromo-2-chloro-1,1,1-trifluoroethane ('Halothane') is shown to function as an efficient solvent/bromine atom donor.