929-57-7

Basic information

• Product Name: 1,6-DIISOCYANOHEXANE
• Synonyms: 1,6-dicyanato-hexan;hexamethylenedi-isocyanicaci;hexamethylenediisocyanicacid;HEXAMETHYLENE DIISOCYANIDE;1,6-DIISOCYANOHEXANE;hexa-1,6-diyl diisocyanide;1,6-DIISOCYANAOHEXANE, 1000MG,NEAT;1,6-Diisocyanohexane,Hexamethylene diisocyanide
• CAS NO: 929-57-7
• Molecular Formula: C₈H₁₂N₂
• Molecular Weight: 136.19
• EINECS: 213-202-0
• Mol File: 929-57-7.mol

Chemical Properties

• Melting Point: 21-23 °C(lit.)
• Boiling Point: 101-103 °C0.5 mm Hg(lit.)
• Flash Point: 219 °F
• Appearance: /
• Density: 0.899 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.443(lit.)
• Storage Temp.: −20°C
• CAS DataBase Reference: 1,6-DIISOCYANOHEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-DIISOCYANOHEXANE(929-57-7)
• EPA Substance Registry System: 1,6-DIISOCYANOHEXANE(929-57-7)

Safety Data

• Hazard Codes: T
• Statements: 23/24-36
• Safety Statements: 26-36/37/39-45
• RIDADR: 2810
• WGK Germany: 3
• RTECS: MO1530000
• F: 10-13-21
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 929-57-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1,6-DIISOCYANOHEXANE is used as a reactant in the synthesis of complex organic structures, particularly for the formation of unusual tricyclic macroheterocycles. It is utilized in reactions with compounds such as 1,1-diisityl-3,3,3-triisopropyldisilaphosphene and analogous disilaarsene to create unique and potentially valuable chemical entities. This application is significant in the field of organic chemistry, where the development of novel compounds can lead to advances in various industries, including pharmaceuticals, materials science, and agrochemicals.

InChI:InChI=1/C8H12N2/c1-9-7-5-3-4-6-8-10-2/h3-8H2

Upstream product

• 124-09-4 1,6-Hexanediamine 
• 77287-34-4 formamide 
• 67-66-3 chloroform 
• 35161-65-0 hexanediyldiformamide 

Downstream Products

• 1333956-90-3 C₂₄H₃₄N₄O₄ 
• 1333956-79-8 C₃₈H₄₆N₄O₄ 
• 1333956-70-9 C₃₀H₄₆N₄O₂ 
• 61578-93-6 N,N'-hexanediyl bis-(thiocarbamic acid (S-phenyl) ester) 
• 111698-34-1 (+/-)_S-isopropyl phenylsulfinate 

Relevant articles and documents

QTMP, a Novel Thiourea Polymer, Causes DNA Damage to Exert Anticancer Activity and Overcome Multidrug Resistance in Colorectal Cancer Cells

Colorectal cancer (CRC) is one of the most common malignancies, and multidrug resistance (MDR) severely restricts the effectiveness of various anticancer drugs. Therefore, the development of novel anticancer drugs for the treatment of CRC patients with MDR is necessary. Quaternized thiourea main-chain polymer (QTMP) is a self-assembled nanoparticle with good water solubility. Notably, QTMP is not a P-glycoprotein (P-gp) substrate, and it exhibits potent cytotoxic activity against CRC cells, including HCT116/DDP and P-gp-mediated multidrug-resistant Caco2 cells. QTMP also exhibits a strong anticancer activity against SW480 cells in vivo. Interestingly, reactive oxygen species (ROS) and reactive nitrogen species (RNS) production were increased in a concentration-dependent manner in QTMP-treated HCT116, SW480 and Caco2 cells. Importantly, QTMP causes DNA damage in these CRC cells via direct insertion into the DNA or regulation of ROS and/or RNS production. QTMP also induces caspase-dependent apoptosis via overproduction of ROS and RNS. Therefore, QTMP is a promising anticancer therapeutic agent for patients with CRC, including those cancer cells with P-gp-mediated MDR. The present study also indicates that the design and synthesis of anticancer drugs based on thiourea polymers is promising and valuable, thereby offering a new strategy to address MDR, and provides reference resources for further investigations of thiourea polymers.

A Combined Photochemical and Multicomponent Reaction Approach to Precision Oligomers

We introduce the convergent synthesis of linear monodisperse sequence-defined oligomers through a unique approach, combining the Passerini three-component reaction (P-3CR) and a Diels–Alder (DA) reaction based on photocaged dienes. A set of oligomers is prepared resting on a Passerini linker unit carrying an isocyano group for chain extension by P-3CR and a maleimide moiety for photoenol conjugation enabling a modular approach for chain growth. Monodisperse oligomers are accessible in a stepwise fashion by switching between both reaction types. Employing sebacic acid as a core unit allows the synthesis of a library of symmetric sequence-defined oligomers. The oligomers consist of alternating P-3CR and photoblocks with molecular weights up to 3532.16 g mol?1, demonstrating the successful switching from P-3CR to photoenol conjugation. In-depth characterization was carried out including size-exclusion chromatography (SEC), high-resolution electrospray ionization mass spectrometry (ESI-MS) and NMR spectroscopy, evidencing the monodisperse nature of the precision oligomers.

Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates

A new method for the synthesis of secondary thiocarbamates from readily available isocyanides and thiosulfonates with broad functional group tolerance is reported. The reaction proceeds under mild reaction conditions in isopropanol and is catalyzed by inexpensive sodium iodide.

Self-assembly of an azobenzene-containing polymer prepared by a multi-component reaction: Supramolecular nanospheres with photo-induced deformation properties

In this article, we have synthesized a polymer containing regulated azobenzene groups by one-pot multi-component polymerization (MCP) based on Passerini reaction, and investigated its self-assembly behavior and photo-induced deformation properties. We found that this molecule can form spherical structures with sizes ranging from hundreds of nanometers to several micrometers when dissolved in THF. NMR and FTIR studies indicate that there are associated hydrogen bonds among the molecules in the aggregates, which are responsible for the formation of the nanospheres. By controlling the stirring rate as the THF suspension is dropped into water, the nanospheres can be sorted according to their size. In this way, we have obtained nanospheres with relatively uniform diameter. When irradiated by UV light in the aqueous medium, the nanospheres tend to aggregate into large clusters, while in dry state they are ready to merge into island-like structures, showing a good photo-induced deformation property.

Synthesis and antiproliferative activity of aromatic and aliphatic bis[aminomethylidene(bisphosphonic)] acids

A series of aromatic and aliphatic bis[aminomethylidene(bisphosphonic)] acids was synthesized in the reaction of triethylphosphite with isonitriles followed by hydrolysis or dealkylation. The in vitro anti-proliferative effect of all synthesized tetraphosphonic acids against MCF-7 breast cancer cells, J774E macrophages and HL-60 promyelocytic leukemia cells was determined. Three aromatic derivatives (5a, 5f and 5j) showed a similar or higher anti-proliferative activity than zoledronic acid.

Multicomponent synthesis of artificial nucleases and their RNase and DNase activity

The synthesis of new, artificial ribonucleases containing two amino acid residues connected by an aliphatic linker has beendeveloped. Target molecules were synthesized via a catalytic three-component Ugi reaction from aliphatic diisocyanides. Preliminaryinvestigations proved unspecific nuclease activity of the new compounds towards single-stranded RNA and doublestrandedcircular DNA .

Reaction of Bidentate Isonitrile Ligands with Iron Carbonyls

Reaction of the bidentate isonitriles CN(CH2)nNC ( n =2, 3, 4, or 6) with (cp = η-cyclopentadienyl) yields exclusively 2> derivatives which are fluxional in solution and exist in three isomeric forms (bridged-bridged, bridged-terminal, and terminal-terminal with respect to the bonding mode of the bidentate isonitrile).The proportion of the isomers containing terminally bound isonitrile increases with the length of the alkyl chain.The complexes may be protonated to yield 2>2 salts (n = 2 or 6) and may be cleaved with I2 to give and 2nNC>> (n = 2 or 6).Reaction ofCN(CH2)nNC (n = 2 or 6 with or yields exclusively 2nNC>>