55183-45-4

Basic information

• Product Name: 5-Hexynoyl chloride
• Synonyms: 5-Hexynoyl chloride
• CAS NO: 55183-45-4
• Molecular Formula: C₆H₇ClO
• Molecular Weight: 130.58
• Mol File: 55183-45-4.mol
• Article Data: 52

Chemical Properties

• Boiling Point: 104-110 °C
• Appearance: /
• Density: 1.089±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 5-Hexynoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hexynoyl chloride(55183-45-4)
• EPA Substance Registry System: 5-Hexynoyl chloride(55183-45-4)

Safety Data

• Hazardous Substances Data: 55183-45-4(Hazardous Substances Data)

Usage

General Description

5-Hexynoyl chloride, also known as hex-5-ynoyl chloride, is a chemical compound with the molecular formula C6H7ClO. This colorless liquid is primarily used as a reagent in organic synthesis and is commonly employed in the production of pharmaceuticals and agrochemicals. It is a reactive compound, capable of undergoing various chemical reactions such as nucleophilic substitution and addition reactions. Additionally, 5-Hexynoyl chloride is known for its potential as a building block for the synthesis of a wide range of organic compounds, making it a versatile and valuable tool in the field of organic chemistry. It is important to handle this compound with caution, as it is corrosive and can cause irritation to the skin, eyes, and respiratory system.

Upstream product

• 14918-21-9 5-hexynonitrile 
• 928-90-5 5-hexyl-1-ol 
• 53293-00-8 hex-5-ynoic acid 

Downstream Products

• 112018-00-5 Tebufelone 
• 124837-37-2 2-methyl-6-trifluoromethylphenol 
• 864936-07-2 C₁₂H₁₂N₂O₃ 
• 864936-05-0 C₁₂H₁₀Cl₃NO 
• 1253176-41-8 1-((2S,3S)-1-(bis(4-methoxy-3,5-dimethyl-phenyl)methyl)-3-phenylaziridin-2-yl)hex-5-yn-1-one 
• 1253176-42-9 1-((2S,3S)-1-(bis(4-methoxy-3,5-dimethyl-phenyl)methyl)-3-cyclohexylaziridin-2-yl)hex-5-yn-1-one 
• 1253176-56-5 1-((2R,3R)-1-(bis(4-methoxy-3,5-dimethyl-phenyl)methyl)-3-phenylaziridin-2-yl)hex-5-yn-1-one 
• 1253176-57-6 1-((2R,3R)-1-(bis(4-methoxy-3,5-dimethyl-phenyl)methyl)-3-cyclohexylaziridin-2-yl)hex-5-yn-1-one 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 1338645-58-1 benzyl N-(5-hexynoyl)-N-[(1S)-1-(1-naphthyl)ethyl]carbamate 
• 1338645-66-1 benzyl N-[(1S)-1-(1-naphthyl)ethyl]-N-{1-[(trimethylsilyl)oxy]-5-hexynyl}carbamate 
• 1338645-82-1 (S)-benzyl N-(1-allyl-5-hexynyl)carbamate 

Relevant articles and documents

Anti-dormant mycobacterial activity and target analysis of nybomycin produced by a marine-derived Streptomyces sp.

Abstract In the course of our search for anti-dormant Mycobacterial substances, nybomycin (1) was re-discovered from the culture broth of a marine-derived Streptomyces sp. on the bioassay-guided separation. Compound 1 showed anti-microbial activity against Mycobacterium smegmatis and Mycobacterium bovis BCG with the MIC of 1.0 μg/mL under both actively growing aerobic conditions and dormancy inducing hypoxic conditions. Compound 1 is also effective to Mycobacterium tuberculosis including the clinically isolated strains. The mechanistic analysis indicated that 1 bound to DNA and induces a unique morphological change to mycobacterial bacilli leading the bacterial cell death.

A flexible synthesis of 68Ga-labeled carbonic anhydrase IX (CAIX)-targeted molecules via CBT/1,2-aminothiol click reaction

We herein describe a flexible synthesis of a small library of68Ga-labeled CAIX-targeted molecules via an orthogonal 2-cyanobenzothiazole (CBT)/1,2-aminothiol click reaction. Three novel CBT-functionalized chelators (1-3) were successfully synthesized and labeled with the positron emitter gallium-68. Cross-ligation between the pre-labeled bifunctional chelators (BFCs) and the 1,2-aminothiol-acetazolamide derivatives (8 and 9) yielded six new68Ga-labeled CAIX ligands with high radiochemical yields. The click reaction conditions were optimized to improve the reaction rate for applications with short half-life radionuclides. Overall, our methodology allows for a simple and efficient radiosynthetic route to produce a variety of68Ga-labeled imaging agents for tumor hypoxia.

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NEW LONG-CHAIN TETRATHIAFULVALENE DERIVATIVES WITH A DIACETYLENE GROUP

The multi-stage synthesis of new long-chain tetrathiafulvalene derivatives containing a diacetylene group at different distances from tetrathiafulvalene moiety - 2-(tetracosa-9,11-diynyl)-, 2-(heptadeca-9,11-diynyl)- and 2-(nonadeca-4,6-diynyl)-6,7-tetrathiafulvalene is described.

Small-molecule fluorophores with large stokes shifts: 9-iminopyronin analogues as clickable tags

The design, synthesis, and both experimental and theoretical studies of several novel 9-(acylimino)- and 9-(sulfonylimino)pyronin derivatives containing either an oxygen or a silicon atom at position 10 are reported. These compounds, especially the Si analogues, exhibit remarkably large Stokes shifts (around 200 nm) while still possessing a high fluorophore brightness, absorption bands in the near-UV and visible part of the spectrum, and high thermal and photochemical stabilities in protic solvents. The reason for the observed large Stokes shifts is an intramolecular charge-transfer excitation of an electron from the HOMO to the LUMO of the chromophore, accompanied by elongation of the C9-N bond and considerable solvent reorganization due to hydrogen bonding to the solvent. Due to the photophysical properties of the studied compounds and their facile and high-yielding synthesis, as well as a simple protocol for their bioorthogonal ligation to a model saccharide using a Huisgen alkyne-azide cycloaddition, they represent excellent candidates for biochemical and biological applications as fluorescent tags and indicators for multichannel imaging. 9-(Acylimino)pyronins alter their optical properties upon protonation and may also be used as pH sensors.

Direct and Enantioselective Aldol Reactions Catalyzed by Chiral Nickel(II) Complexes

A direct and asymmetric aldol reaction of N-acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes is reported. The reaction gives the corresponding O-TIPS-protected anti-aldol adducts in high yields and with remarkable stereocontrol and atom economy. Furthermore, the straightforward removal of the achiral scaffold provides enantiomerically pure intermediates of synthetic interest, which involve precursors for anti-α-amino-β-hydroxy and α,β-dihydroxy carboxylic derivatives. Theoretical calculations explain the observed high stereocontrol.

Decarboxylative Borylation of mCPBA-Activated Aliphatic Acids

A decarboxylative borylation of aliphatic acids for the synthesis of a variety of alkylboronates has been developed by mixing m-chloroperoxybenzoic acid (mCPBA)-activated fatty acids with bis(catecholato)diboron in N,N-dimethylformamide (DMF) at room temperature. A radical chain process is involved in the reaction which initiates from the B-B bond homolysis followed by the radical transfer from the boron atom to the carbon atom with subsequent decarboxylation and borylation.