18229-85-1

Basic information

• Product Name: 1,1-diethoxyhex-3-yne
• Synonyms: 1,1-diethoxyhex-3-yne;1,1-Diethoxy-3-hexyne;3-Hexyne-1-al diethyl acetal;Einecs 242-111-9
• CAS NO: 18229-85-1
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.24872
• EINECS: 242-111-9
• Mol File: 18229-85-1.mol

Chemical Properties

• Boiling Point: 216.7°Cat760mmHg
• Flash Point: 66.4°C
• Appearance: /
• Density: 0.896g/cm³
• Vapor Pressure: 0.203mmHg at 25°C
• Refractive Index: 1.437
• CAS DataBase Reference: 1,1-diethoxyhex-3-yne(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-diethoxyhex-3-yne(18229-85-1)
• EPA Substance Registry System: 1,1-diethoxyhex-3-yne(18229-85-1)

Safety Data

• Hazardous Substances Data: 18229-85-1(Hazardous Substances Data)

Usage

Type of compound

Alkyne

Structural feature

Two ethoxy (C2H5O) groups attached to a hex-3-yne skeleton

Common use

Reagent in organic chemistry synthesis reactions

Specific application

Formation of carbon-carbon bonds

Additional uses

Production of various organic compounds, including pharmaceuticals, pesticides, and flavoring agents

Research and development

Utilized in the development of new materials and chemical processes in the industry

Role in organic chemistry

Significant and versatile building block for numerous applications

InChI:InChI=1/C10H18O2/c1-4-7-8-9-10(11-5-2)12-6-3/h10H,4-6,9H2,1-3H3

Upstream product

• 18229-78-2 2-hexynyl aldehyde diethyl acetal 
• 13397-78-9 4,4-diethoxybut-1-yne 
• 75-03-6 ethyl iodide 
• 89533-67-5 3-hexyn-1-al 
• 122-51-0 orthoformic acid triethyl ester 
• 627-19-0 1-Pentyne 

Downstream Products

• 73545-18-3 (Z)-3-hexenal diethyl acetal 
• 6789-80-6 (3Z)-hexenal 

Relevant articles and documents

Clean and Efficient Oxidation of Homoallylic and Homopropargylic Alcohols into β,γ-Unsaturated Aldehydes by The Dess-Martin Periodinane

We describe the first efficient oxidation of homoallylic and homopropargylic alcohols to the corresponding very sensitive and unstable β,γ-unsaturated aldehydes by using Dess-Martin periodinane with a new neutral and anhydrous extraction protocol.

Total synthesis of 17-isolevuglandin E4 and the structure of C22-PGF(4α)

The isolevuglandin 17-isoLGE4 (10-acetyl-11-formyl-14-hydroxynonadeca-4(Z),7(Z),12(E),16(Z)-tet raenoic acid) is a levulinaldehyde derivative that is expected to be generated during the free radical-induced oxidation of docosahexaenoic acid. A total synthesis was executed to facilitate detection and identification of 17-isoLGE4 in biological samples. Conjugate addition of a higher order vinyl cyanocuprate to a γ-alkoxy enone achieved the final carbon-carbon bond formation to complete a convergent elaboration of the 17-isoLGE4 carbon, skeleton. Attempted construction of the requisite vinyl nucleophile synthon using hydrostannylation of an alkyne was foiled by tri-n-butylstannyl radical-promoted isomerization of acis to a trans double bond. Derivatization of 17-isoLGE4 with methoxylamine under anhydrous or wet conditions generated bismethoximes of 17-isoLGE4 or the isomerized Δ11-17-isoLGE4 respectively. Analysis of the mass spectrum of a bismethoxime-pentafluorobenzyl ester-trimethylsilyl ether derivative of 17-isoLGE4 provided presumptive evidence that an incorrect structure was proposed earlier for C22-PGF(4α), the only F4-isoprostane which is produced enzymatically. We conclude that the 22-carbon analogue of PGF(2α), produced from docosahexaenoic acid by a cyclooxygenase from trout gill, does not have the same side chains as 17-isoLGE4. Furthermore, we now propose that mass spectral data reported for 'C22-PGF(4α)' support a 14-PGF(4α) structure rather than the 17-PGF(4α) structure suggested previously.