16355-92-3

Basic information

• Product Name: 1,10-DIIODODECANE
• Synonyms: 1,10-diiodo-decan;DECAMETHYLENE DIIODIDE;1,10-DIIODODECANE;1,10-DIIODODECANE TECH;1,10-diiodododecane;1,10-Diiododecane,97%
• CAS NO: 16355-92-3
• Molecular Formula: C₁₀H₂₀I₂
• Molecular Weight: 394.07
• EINECS: 240-415-6
• Product Categories: Iodine Compounds;Alkyl;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 16355-92-3.mol

Chemical Properties

• Melting Point: 33-35 °C(lit.)
• Boiling Point: 197-200 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 2,35 g/cm3
• Vapor Pressure: 9.34E-05mmHg at 25°C
• Refractive Index: 1.4824 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in methanol.
• Sensitive: Light Sensitive
• BRN: 1738614
• CAS DataBase Reference: 1,10-DIIODODECANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,10-DIIODODECANE(16355-92-3)
• EPA Substance Registry System: 1,10-DIIODODECANE(16355-92-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: 2811
• WGK Germany: 3
• F: 8
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 16355-92-3(Hazardous Substances Data)

Usage

Uses

1. Used as an Alkylating Agent:
1,10-Diiododecane is used as an alkylating agent in the synthesis of symmetrical and unsymmetrical bis-cryptophanes. It serves as a crucial component in the formation of these complex organic molecules, which have potential applications in various fields, including pharmaceuticals and materials science.
2. Used as a Crosslinking Reagent:
In the field of polymer chemistry, 1,10-diiododecane acts as a crosslinking reagent for tetrabutylammonium polygalacturonic acid. This application is significant in enhancing the properties of polymers, such as their mechanical strength, stability, and durability.
3. Used in the Production of Decane:
1,10-Diiododecane is also utilized to produce decane at a temperature of 20°C. Decane is an important hydrocarbon with various industrial applications, such as in the production of lubricants, solvents, and fuels.
4. Used in Chemical Synthesis:
Due to its unique chemical properties, 1,10-diiododecane is employed in various chemical synthesis processes, where it serves as a valuable intermediate or reagent for the production of different organic compounds.

InChI:InChI=1/C10H20I2/c11-9-7-5-3-1-2-4-6-8-10-12/h1-10H2

Upstream product

• 61575-02-8 1,10-diphenoxy-decane 
• 10034-85-2 hydrogen iodide 
• 110-40-7 diethyl sebacate 
• 112-47-0 1,10-Decanediol 
• 10471-28-0 diethyl dodecanedioate 
• 53463-68-6 1-bromo-10-decanol 
• 4101-68-2 1,10-dibromodecane 
• 32366-73-7 decane-1,10-diyl dimethanesulfonate 
• 40339-97-7 (5-iodo-pentyl)-phenyl ether 
• 111-20-6 1,10-decanedioic acid 
• 2162-98-3 1,10-dichlorodecane 

Downstream Products

• 578-95-0 10H-acridin-9-one 
• 82136-01-4 1,10-bis(phenylthio)decane 
• 426-64-2 1,10-bis-heptafluorobutyryloxy-decane 
• 4543-66-2 1,12-dodecanedinitrile 
• 124-18-5 decane 
• 112-95-8 icosane 
• 91346-98-4 1,10-dinitrodecane 
• 111-23-9 N,N'''-1,10-decanediylbisguanidine 
• 860519-07-9 1-(10-iodo-decyloxy)-4-methoxy-benzene 
• 31719-07-0 N₁,N₁₀-dibenzyldecane-1,10-diamine 
• 1420-40-2 N,N,N,N',N',N'-hexamethyldecanediammonium iodide 
• 117688-82-1 N,N''-(1,10-decanediyl)bis(N,N'-dicyclohexyl-4-morpholinecarboximidamide) 
• 19102-90-0 dimethyl hexadecanedioate 
• 1191-67-9 decane-1,10-dithiol 

Relevant articles and documents

Highly Selective Radical Monoreduction of Dihalides Confined to a Dynamic Supramolecular Host

Reduction of alkyl dihalide guests (2–5 and 7) with trialkylsilanes (R3SiH) was performed in water-soluble host 1 to investigate the effects of confinement on fast radical reactions (k≥103 m?1 s?1). High selectivity (>95 %) for mono-reduced products was observed for primary and secondary dihalide guests under mild conditions. The results highlight the importance of host–guest complexation rates to modulate the product selectivity in radical reactions.

Inhibition of protein kinase Cα by dequalinium analogues: Dependence on linker length and geometry

Analogues of a bipartite compound, dequalinium (DECA) (quinolinium, 1,1'-(1,10-decanediyl)bis(4-amino-2-methyl diiodide)), were tested for inhibition of protein kinase Cα (PKCα). In vitro assays of monomeric and dimeric analogues support a model in which DECA inhibits PKCα by an obligatory two-point contact, a unique mechanism among PKC inhibitors. The presence of unsaturation in the center of the C10-alkyl linker produced geometric isomers with different inhibitory potencies: cis IC50 = 52 ± 12 μM and trans IC50 = 12 ± 3 μM, where the trans isomer was equipotent to that of the saturated C10-DECA. DECA analogues with longer, saturated linkers (C12, C14, or C16) exhibited enhanced inhibitory potencies which reached a plateau with the C14-linker (IC50 = 2.6 ± 0.2 μM). Metastatic melanoma cells treated with 250 nM C12-, C14-, or C16-DECA and irradiated with long-wave UV light (which causes irreversible inhibition of PKCα by DECA) confirmed the linker-dependent inhibition of intracellular PKCα activity.

A Simple Convenient Procedure for Iodination of Alcohols and Reductive Iodination of Carbonyl Compounds using N,N-Diethylaniline-Borane-I2 system.

Alcohols, carboxylic acids and carbonyl compounds give the corresponding alkyl iodides in moderate to good yields on reaction with N,N-diethylaniline-borane complex and iodine.

Low-Frequency Raman Spectra of Even α,ο-Disubstituted n-Alkanes

Low-frequency Raman spectra of even α,ο-disubstituted n-alkanes have been recorded.The major features in the spectra arise from whole-chain longitudinal and bending vibrations.The effects of end group, chain lenght, and temperature on the frequencies of these vibrations are described, and the frequencies of the longitudinal vibrations are interpreted in terms of the chain model of Minoni and Zerbi.

Probing the Existence of a Metastable Binding Site at the β2-Adrenergic Receptor with Homobivalent Bitopic Ligands

Herein, we report the development of bitopic ligands aimed at targeting the orthosteric binding site (OBS) and a metastable binding site (MBS) within the same receptor unit. Previous molecular dynamics studies on ligand binding to the β2-adrenergic receptor (β2AR) suggested that ligands pause at transient, less-conserved MBSs. We envisioned that MBSs can be regarded as allosteric binding sites and targeted by homobivalent bitopic ligands linking two identical pharmacophores. Such ligands were designed based on docking of the antagonist (S)-alprenolol into the OBS and an MBS and synthesized. Pharmacological characterization revealed ligands with similar potency and affinity, slightly increased β2/β1AR-selectivity, and/or substantially slower β2AR off-rates compared to (S)-alprenolol. Truncated bitopic ligands suggested the major contribution of the metastable pharmacophore to be a hydrophobic interaction with the β2AR, while the linkers alone decreased the potency of the orthosteric fragment. Altogether, the study underlines the potential of targeting MBSs for improving the pharmacological profiles of ligands.

BIVALENT BROMODOMAIN LIGANDS, AND METHODS OF USING SAME

Described herein are compounds capable of modulating one or more biomolecules substantially simultaneously, e.g., modulating two or more binding domains (e.g., bromodomains) on a protein or on different proteins. For example, in one aspect, a bivalent compound or a pharmaceutically acceptable salt, stereoisomer, metabolite, or hydrate thereof is provided. In another aspect, a method of treating a disease associated with a protein having tandem bromodomains in a patient in need thereof is provided. The method comprises administering to the patient the bivalent compound as described.

New synthesis of (11Z,13Z)-11,13-Hexadecadienal, the female sex pheromone of the navel orangeworm

(11Z,13Z)-11,13-Hexadecadienal, the female sex pheromone of the navel orangeworm (Amyelois transitella), was synthesized from commercially available 10-bromo-1-decanol in a 27% overall yield (8 steps). The synthesis was achieved by using 10-iododecanal, trimethylsilylacetylene and (Z)-1-bromo-12-butene as the key building blocks, employing Sonogashira-Hagihara coupling and Brown's hydroboration-protonolysis as the key reactions. The terminal formyl group was installed in the earlier stage of the synthesis rather than in the final step. This procedure enabled the multi-gram-scale preparation of this economically important pheromone.

The synthesis of phosphates of long-chain ω-hydroxyalkyl esters of 11-deoxyprostaglandin E1

Di(p-methylbenzyl) phosphates of ω-hydroxyalkyl esters of 11-deoxyprostaglandin E1 were synthesized from disubstituted 1,10-decane and 1,22-docosane derivatives for studying the permeability of bilayer membranes.

Sharpless AD strategy towards the γ-methyl butenolide unit of acetogenins: Enantioselective synthesis of butenolide I and II with mosquito larvicidal activity

A novel synthetic strategy toward the γ-methyl butenolides has been established based on Sharpless asymmetric dihydroxylation in high yields and good enantiopurity. The route could be expanded to the synthesis of α,γ-disubstituted butenolide units of naturally occurring annonaceous acetogenins. Utilizing this strategy, three simple natural products with butenolide segments were synthesized enantioselectively.

Quantum interference effects in self-assembled asymmetric disulfide monolayers: Comparisons between experiment and ab initio/Monte Carlo theories

Electron transfer measurements between solution redox probes and a Au electrode coated with self-assembled monolayers of symmetric and asymmetric ??-hydroxyalkane disulfides are used to probe the quantum interference between hydrocarbon chains of different lengths. While ab initio theory predicts a measurable destructive interference effect between hydrocarbon chains differing in length by a single methylene unit, electron transfer rates for the ferricyanide and horse heart cytochrome c are more consistent with rates estimated in the absence of the interference effect. The discrepancy between theory and experiment is discussed in light of possible interchain electronic coupling and phase segregation within the monolayers and limitations of the theoretical models.