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3-Hexyne is an organic compound with the chemical formula C6H10, featuring a triple bond between the third and fourth carbon atoms in a hexane chain. It is a colorless liquid with a distinctive odor and is used as a building block in various chemical reactions.

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  • 928-49-4 Structure
  • Basic information

    1. Product Name: 3-HEXYNE
    2. Synonyms: C2H5CequivCC2H5;Hex-3-yne;3-HEXYNE;Dithylacetylene;DIETHYLACETYLENE;3-Hexyne,99%;3-Hexene-D10;ethylpropylacetylene
    3. CAS NO:928-49-4
    4. Molecular Formula: C6H10
    5. Molecular Weight: 82.14
    6. EINECS: 213-173-4
    7. Product Categories: Acetylenes;Acetylenic Hydrocarbons;Alkynes;Internal;Organic Building Blocks
    8. Mol File: 928-49-4.mol
  • Chemical Properties

    1. Melting Point: -103.1°C
    2. Boiling Point: 81-82 °C(lit.)
    3. Flash Point: 6 °F
    4. Appearance: Clear colorless to pale yellow/Liquid
    5. Density: 0.723 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 186 mm Hg ( 37.7 °C)
    7. Refractive Index: n20/D 1.411(lit.)
    8. Storage Temp.: Flammables area
    9. Solubility: 0.559g/l
    10. Water Solubility: Not miscible in water.
    11. BRN: 1731158
    12. CAS DataBase Reference: 3-HEXYNE(CAS DataBase Reference)
    13. NIST Chemistry Reference: 3-HEXYNE(928-49-4)
    14. EPA Substance Registry System: 3-HEXYNE(928-49-4)
  • Safety Data

    1. Hazard Codes: F,Xn,Xi
    2. Statements: 11-36/37/38-65
    3. Safety Statements: 16-26-36-62-33-7/9
    4. RIDADR: UN 3295 3/PG 2
    5. WGK Germany: 3
    6. RTECS:
    7. HazardClass: 3
    8. PackingGroup: II
    9. Hazardous Substances Data: 928-49-4(Hazardous Substances Data)

928-49-4 Usage

Uses

Used in Organometallic Chemistry:
3-Hexyne is used as a reactant in the synthesis of fused hetero-hydropyridyl ligands bonded to the Ru(p-cymene) organometallic moiety. This application is significant in the development of new organometallic complexes with potential applications in catalysis, materials science, and medicinal chemistry.
Used in Organic Synthesis:
3-Hexyne is used as a reactant in the preparation of [4+2] cycloaddition products by reacting with borole. This reaction is an important method for constructing complex organic molecules and has applications in the synthesis of natural products, pharmaceuticals, and other bioactive compounds.

Purification Methods

Purify as for 1-hexyne above. [Beilstein 1 IV 1009.]

Check Digit Verification of cas no

The CAS Registry Mumber 928-49-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,2 and 8 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 928-49:
(5*9)+(4*2)+(3*8)+(2*4)+(1*9)=94
94 % 10 = 4
So 928-49-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H10/c1-3-5-6-4-2/h3-4H2,1-2H3

928-49-4 Well-known Company Product Price

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  • Alfa Aesar

  • (L02682)  3-Hexyne, 99%   

  • 928-49-4

  • 5g

  • 248.0CNY

  • Detail
  • Alfa Aesar

  • (L02682)  3-Hexyne, 99%   

  • 928-49-4

  • 25g

  • 1012.0CNY

  • Detail
  • Aldrich

  • (306894)  3-Hexyne  99%

  • 928-49-4

  • 306894-5G

  • 362.70CNY

  • Detail
  • Aldrich

  • (306894)  3-Hexyne  99%

  • 928-49-4

  • 306894-25G

  • 1,329.12CNY

  • Detail

928-49-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name hex-3-yne

1.2 Other means of identification

Product number -
Other names EINECS 213-173-4

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:928-49-4 SDS

928-49-4Relevant articles and documents

Isolable Copper(I) ?2-Cyclopropene Complexes

Noonikara-Poyil, Anurag,Ridlen, Shawn G.,Dias, H.V.Rasika

, p. 17860 - 17865 (2020/11/30)

Treatment of bis(pyrazolyl)borate ligand supported [(CF3)2Bp]Cu(NCMe) with 1,2,3-trisubstituted cyclopropenes produced thermally stable copper(I) ?2-cyclopropene complexes amenable to detailed solution and solid-state analysis. The [(CF3)2Bp]Cu(NCMe) also catalyzed [2 + 1]-cycloaddition chemistry of terminal and internal alkynes with ethyl diazoacetate affording cyclopropenes, including those used as ligands in this work. The tris(pyrazolyl)borate [(CF3)2Tp]Cu(NCMe) is a competent catalyst for this process as well. The treatment of [(CF3)2Tp]Cu with ethyl 2,3-diethylcycloprop-2-enecarboxylate substrate gave an O-bonded rather than a ?2-cyclopropene copper complex.

A novel approach for rhodium(iii)-catalyzed C-H functionalization of 2,2′-bipyridine derivatives with alkynes: A significant substituent effect

Wu, Shaonan,Wang, Zhuo,Bao, Yinwei,Chen, Chen,Liu, Kun,Zhu, Bolin

supporting information, p. 4408 - 4411 (2020/05/05)

We described a novel approach for the C-H functionalization of 2,2′-bipyridine derivatives with alkynes. DFT calculations and experimental data showed a significant substituent effect at the 6-position of 2,2′-bipyridine, which weakened the adjacent N-Rh bond and provided the possibility of subsequent rollover cyclometalation, C-H activation, and functionalization.

Rhodium(iii)-catalyzed unreactive C(sp3)-H alkenylation of N-alkyl-1H-pyrazoles with alkynes

Li, Tongyu,Liu, Chang,Wu, Shaonan,Chen, Chen C.,Zhu, Bolin

supporting information, p. 7679 - 7683 (2019/08/30)

The first example of pyrazole-directed rhodium(iii)-catalyzed unreactive C(sp3)-H alkenylation with alkynes has been described, which showed a relatively broad substrate scope with good functional group compatibility. Moreover, we demonstrated that the transitive coordinating center pyrazole could be easily removed under mild conditions.

A Mild Rhodium Catalyzed Direct Synthesis of Quinolones from Pyridones: Application in the Detection of Nitroaromatics

Biswas, Aniruddha,Giri, Dipanjan,Das, Debapratim,De, Anurima,Patra, Sanjib K.,Samanta, Rajarshi

, p. 10989 - 10996 (2017/10/27)

A rhodium catalyzed direct regioselective oxidative annulation by double C-H activation is described to synthesize highly substituted quinolones from pyridones. The reaction proceeds at mild conditions with broad scope and wide functional group tolerance. These novel quinolones were explored to recognize nitroaromatic compounds.

Lewis acid activation of molybdenum nitrides for alkyne metathesis

Finke, Aaron D.,Moore, Jeffrey S.

supporting information; experimental part, p. 7939 - 7941 (2011/01/04)

The substantial kinetic barrier to molybdenum nitride-alkyne metathesis is facilitated by precomplexation of the borane Lewis acid B(C6F 5)3, providing convenient access to metathesis-active molybdenum alkylidynes. Spectroscopic and X-ray structural analysis suggest MoN bond weakening upon borane complexation.

Development of a well-defined silica-supported tungstenocarbyne complex as efficient heterogeneous catalyst for alkyne metathesis

Merle, Nicolas,Taoufik, Mostafa,Nayer, Morad,Baudouin, Anne,Roux, Erwan Le,Gauvin, Régis M.,Lefebvre, Frédéric,Thivolle-Cazat, Jean,Basset, Jean-Marie

, p. 1733 - 1737 (2008/09/18)

The interaction of [W({triple bond, long}C-tBu)(CH2-tBu)(OAr)2] (Ar = 2,6-iPr2C6H3) (1), with the hydroxyl groups of a silica dehydroxylated at 700 °C leads to [({triple bond, long}SiO)W(OAr)2({triple bond, long}C-tBu)] (2) which was characterized by IR, solid-state NMR and mass balance analysis. This well-defined surface species is an efficient catalyst for the metathesis of pent-2-yne.

Highly active molybdenum-alkylidyne catalysts for alkyne metathesis: Synthesis from the nitrides by metathesis with alkynes

Gdula, Robyn L.,Johnson, Marc J. A.

, p. 9614 - 9615 (2007/10/03)

Terminal nitrido complexes N≡Mo(OC(CF3)2Me)3 (4), N≡Mo(OC(CF3)2Me)3(NCMe) (4-NCMe), and NMo(OC(CF3)3)3(NCMe) (5-NCMe) react irreversibly with 3-hexyne at elevated temperature in hydrocarbon solution to form the corresponding propylidyne complexes EtC≡Mo(OC(CF3)2Me)3 (3) and EtC≡Mo(OC(CF3)3)3 (6), long known as exceptionally active catalysts for alkyne metathesis. The propylidyne complexes are isolated as the more readily crystallized 1,2-dimethoxyethane (DME) adducts for convenience; 3-DME is isolated in 61% yield on a multigram scale. Copyright

A highly active, heterogeneous catalyst for alkyne metathesis

Weissman, Haim,Plunkett, Kyle N.,Moore, Jeffrey S.

, p. 585 - 588 (2007/10/03)

(Chemical Equation Presented) An alkylidyne molybdenum amide complex is attached to nontoxic, amorphous silica to form a highly active, recyclable heterogeneous catalyst for alkyne metathesis. The catalyst does not undergo alkyne polymerization, can be utilized at a loading of 1 mol% at room temperature, and has shown unprecedented metathesis activity for the homodimerization of 2-propynylthiophene, a substrate that was previously problematic for alkyne metathesis.

HETEROGENEOUS ALKYNE METATHESIS

-

Page/Page column 7; 8, (2008/06/13)

The present invention provides heterogeneous organometallic catalysts for alkyne metathesis, including the metathesis of internal alkynes. Organometallic precursors are covalently bonded to the oxygen atoms of metal oxide supports to form catalysts having carbyne functionality. The heterogeneous catalysts provide improved turn-over frequencies at lower reaction temperatures than conventional catalysts.

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