17830-03-4

Basic information

• Product Name: 9-Iodo-o-carborane
• Synonyms: 9-Iodo-o-carborane
• CAS NO: 17830-03-4
• Molecular Formula: C₂H₁₁B₁₀I
• Molecular Weight: 259.03
• Mol File: 17830-03-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 9-Iodo-o-carborane(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Iodo-o-carborane(17830-03-4)
• EPA Substance Registry System: 9-Iodo-o-carborane(17830-03-4)

Safety Data

• Hazardous Substances Data: 17830-03-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
9-Iodo-o-carborane is used as a versatile reactant in Pd-catalyzed coupling reactions of amides with iodoand diiodocarborane. This application allows for the synthesis of aminocarboranes and diamidocarboranes, which are important intermediates in the development of new pharmaceuticals, materials, and chemical compounds.
Used in Fluorescence Microscopy Imaging:
In the field of biochemistry and molecular biology, 9-Iodo-o-carborane is utilized as a reactant in the carborane-enhanced two-photon absorption of tribranched fluorophores. This enhancement enables more efficient and sensitive fluorescence microscopy imaging, which is crucial for studying cellular processes and structures at a high resolution.
Used in Pharmaceutical Development:
Due to its unique properties, 9-Iodo-o-carborane can be incorporated into the design and synthesis of new pharmaceutical agents. Its electron-accepting nature and thermal stability make it a promising candidate for the development of drugs targeting various diseases and conditions.
Used in Material Science:
9-Iodo-o-carborane's strong electron-accepting characteristics and stability also make it suitable for use in the development of new materials with unique electronic, optical, and thermal properties. These materials can be applied in various industries, such as electronics, energy, and aerospace.

Upstream product

• 16872-09-6 1,2-dicarba-closo-dodecaborane⁽¹²⁾ 
• 7553-56-2 iodine 
• 17157-02-7 9-iodo-m-carborane 
• 81353-28-8 phenyl-9-o-carboranyliodonium tetrafluoroborate 
• 7446-70-0 aluminium trichloride 
• 7789-23-3 potassium fluoride 

Downstream Products

• 16872-09-6 1,2-dicarba-closo-dodecaborane⁽¹²⁾ 
• 92-52-4 biphenyl 
• 123462-83-9 9-(p-hydroxyphenyl)-o-carborane 
• 123482-14-4 9-(p-methoxyphenyl)-o-carborane 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 16872-10-9 1-methyl-o-carborane 
• 123462-81-7 9-(o-carboran-1-ylmethyl)-o-carborane 
• 22043-65-8 3-amino-1,2-dicarbaborane 
• 75563-94-9 9-phenyl-1,2-dicarba-closo-dodecaborane⁽¹²⁾ 
• 75563-93-8 9-benzyl-1,2-carborane 
• 17702-35-1 9,12-diiodo-1,2-dicarba-closo-dodecarborane⁽¹²⁾ 
• 80746-63-0 9-phenylethynyl-1,2-dicarba-closo-dodecaborane⁽¹²⁾ 
• 65664-41-7 9-p-fluorophenyl-o-carborane 
• 82378-25-4 9-(4-methylphenyl)-1,2-dicarba-closo-dodecaborane 

Relevant articles and documents

Quantitative Assessment of Substitution NMR Effects in the Model Series of o-Carborane Derivatives: α-Shift Correlation Method

The principles of a new α-shift correlation (ASC) NMR method are demonstrated on a model series of substituted derivatives of o-carborane for which reliable NMR data are available. This graphical method revealed an acceptable linear correlation between α(11B) or α(13C) shifts and those induced by substituents in unsubstituted (u) positions of the carborane cluster. The linearity holds for all nuclei involved in skeletal bonding: Δδ(N)u = g × α (where N = 11B, 13C, and 1H). The factor g (slope of the correlation line × 102) becomes an important measure of sensitivity of a given cage position to substituent changes. The β, γ, and δ = A (= antipodal) shifts can be therefore derived from the α-shift, are linearly proportional, and reflect additive character in double substitution. The ASC method appears to be an important tool for quantitative assessment of substituent NMR effects in all exo-substituted boron-cluster systems.

Designed synthesis of new ortho-carborane derivatives: From mono- to polysubstituted frameworks

The use of nucleophilic and electrophilic processes allow the designed synthesis of several B-iodinated derivatives of o-carborane. Because of the straightforward Pd-catalyzed conversion of B-I to B-C bond with Grignard reagents, such as methylMgBr and biPhenylMgBr, both, symmetrical 3,6-R 2-1,2-closo-C2B10H10 and asymmetrical 3-I-6-Me-1,2-closo-C2B10H10 could be obtained. Not only conventional reactions in solution have been studied but also a highly efficient, clean and fast solvent-free procedure has provided successful results to regioselectively produce B-iodinated o-carborane derivatives by a careful control of the reaction conditions. The high number of nonequivalent leaving groups in boron iodinated o-carborane derivatives opens the possibility through B-C coupling to materials with novel possibilities and to self-assembling due to the enhanced polarizability of the C-H bond.