8-Chloro-1-octyne

• CAS: 24088-97-9
• Catalog Number: ACM24088979
• Category: Main Products
• Molecular Weight: 144.64
• Molecular Formula: C₈H₁₃Cl
• Synonyms: 1-Octyne,8-chloro; 1-Chloro-7-octyne; 8-chloro-oct-1-yne; 8-Chlor-oct-1-in; chloro-1 octyne-7; 8-Chloro-1-octyne
• IUPAC Name: 8-chlorooct-1-yne
• Canonical SMILES: C#CCCCCCCCl
• InChI Key: HQHUHJPIECZMCX-UHFFFAOYSA-N
• Boiling Point: 183.3ºC at 760mmHg
• Flash Point: 60.2ºC
• Density: 0.928g/cm³
• Exact Mass: 144.07100

Case Study

Synthesized sialosides for influenza detection using 8-chloro-1-octyne

He, Yun. (2014).

Glycan microarrays composed of O-linked sialosides have become an important tool for studying the binding profile of influenza viruses. However, since viral NA can hydrolyze O-linked terminal sialic acids, NA inhibitors or low temperatures are required when performing binding assays. The synthesis of NA-resistant sialosides containing different glycosidic bonds (C-, S-, and N-) using 8-chloro-1-octyne and others is described. The stability of these sialosides is compared to O-linked sialosides, and the ability of these molecules to capture influenza viruses at ambient temperature without the addition of NA inhibitors is demonstrated. Each influenza virus strain exhibits a unique binding pattern on the microarray.
41 (377 mg, 0.73 mmol) and 8-chloro-1-octyne (126 mg, 1.09 mmol, 1.5 eq) were placed in an aluminum foil flask, 10 ml of acetonitrile was added, followed by N,N-diisopropylethylamine (361 ul, 2.18 mmol, 3 eq) and copper (I) iodide (277 mg, 1.46 mmol, 2 eq). The reaction mixture was stirred at 60 °C overnight, concentrated and loaded onto a silica gel column. Hexane/acetone (2:3) was used as the eluent to give 5 (405 mg, 84%).

8-Chloro-1-octyne for modular introduction of peroxides

Horn, Alissa, and Patrick H. Dussault. RSC advances 10.72 (2020): 44408-44429.

8-Chloro-1-octyne (3.3914 g, 23.45 mmol) was reacted with sodium iodide via Finkelstein exchange to generate 8-iodo-1-octyne (91% yield), which was used without further purification. This iodinated intermediate then underwent nucleophilic substitution with tert-butyl hydroperoxide in the presence of CsOH to generate 8-(tert-Butylperoxy)-1-octyne, a peroxy-substituted alkyne substrate. The synthesized peroxyalkyne can serve as a substrate for CuAAC reaction with azides in the presence of Cu(I) to generate peroxy-substituted 1,2,3-triazoles. This reaction is effective in both organic and biphasic media and has been used for the functionalization of gold nanoparticles, the first reported process of this kind.
Unfunctionalized peroxyalkynes can be readily assembled on the corresponding chloroalkynes via Finkelstein exchange, followed by nucleophilic displacement of the iodide with tert-butyl hydroperoxide in the presence of CsOH. Iodination of the terminal alkynes afforded the corresponding iodoalkynes in good yields.

Custom Q&A

What is the molecular formula of 8-Chloro-1-octyne?

The molecular formula is C8H13Cl.

What are the synonyms for 8-Chloro-1-octyne?

The synonyms are 8-chlorooct-1-yne, 1-Octyne, 8-chloro-, 1-chloro-7-octyne, and 1-chlorooct-7-yne.

What is the IUPAC name of 8-Chloro-1-octyne?

The IUPAC name is 8-chlorooct-1-yne.

What is the InChI code of 8-Chloro-1-octyne?

The InChI code is InChI=1S/C8H13Cl/c1-2-3-4-5-6-7-8-9/h1H,3-8H2.

What is the InChIKey of 8-Chloro-1-octyne?

The InChIKey is HQHUHJPIECZMCX-UHFFFAOYSA-N.

What is the canonical SMILES of 8-Chloro-1-octyne?

The canonical SMILES is C#CCCCCCCCl.

What is the CAS number of 8-Chloro-1-octyne?

The CAS number is 24088-97-9.

What is the molecular weight of 8-Chloro-1-octyne?

The molecular weight is 144.64 g/mol.

How many rotatable bonds are there in 8-Chloro-1-octyne?

There are 5 rotatable bonds.

Is 8-Chloro-1-octyne a covalently-bonded unit?

Yes, it is a covalently-bonded unit.