629-74-3

Basic information

• Product Name: 1-HEXADECYNE
• Synonyms: 1-HEXADECYNE;N-TETRADECYLACETYLENE;TIMTEC-BB SBB008791;1-Hexadecyne 90%;hexadec-1-yne;1-Hexadecyne, 98+%;1-Hexadecyne,tech.90%;1-HEXADECYNE, 90+%
• CAS NO: 629-74-3
• Molecular Formula: C₁₆H₃₀
• Molecular Weight: 222.41
• EINECS: 211-106-3
• Product Categories: Acetylenes;Acetylenic Hydrocarbons
• Mol File: 629-74-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 15°C
• Boiling Point: 148°C 10mm
• Flash Point: >110°C
• Appearance: /
• Density: 0,797 g/cm3
• Vapor Pressure: 0.00515mmHg at 25°C
• Refractive Index: 1.4420
• BRN: 1702804
• CAS DataBase Reference: 1-HEXADECYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-HEXADECYNE(629-74-3)
• EPA Substance Registry System: 1-HEXADECYNE(629-74-3)

Safety Data

• Statements: 11
• Safety Statements: 24/25
• TSCA: Yes
• Hazardous Substances Data: 629-74-3(Hazardous Substances Data)

Usage

General Description

1-Hexadecyne is a linear alkyne with the chemical formula C16H30. It is a clear, colorless liquid with a faint odor and a melting point of around -10 degrees Celsius. 1-Hexadecyne is commonly used in organic synthesis and chemical research as a building block for the preparation of various compounds. It is also used as a reagent in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. Additionally, 1-Hexadecyne is known for its potential application in the field of materials science, particularly in the development of functionalized surfaces and coatings. While it is generally considered to have low toxicity, proper handling and safety precautions should be observed when working with 1-Hexadecyne due to its flammability and potential irritant effects. Overall, 1-Hexadecyne serves as a valuable chemical intermediate in the preparation of diverse chemical products and materials.

InChI:InChI=1/C16H30/c1-3-5-7-9-11-13-15-16-14-12-10-8-6-4-2/h1H,4-16H2,2H3

Upstream product

• 36653-82-4 1-Hexadecanol 
• 112-71-0 1-Bromotetradecane 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 6920-24-7 hexadecane-1,2-diol 
• 2765-11-9 n-pentadecanal 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 629-73-2 1-Hexadecene 
• 2834-02-8 heptadec-2-ynoic acid 
• 63758-87-2 1,2-dibromohexadecane 
• 313990-60-2 1-bromohexadec-1-ene 
• 629-75-4 2-hexadecyne 
• 111-83-1 1-bromo-octane 
• 81216-13-9 8-bromooct-1-yne 
• 74-86-2 acetylene 

Downstream Products

• 629-75-4 2-hexadecyne 
• 67471-17-4 15,17-dotriacontadiyne 
• 150240-39-4 chaetomellic anhydride A 

Relevant articles and documents

SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes

Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C=C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).

Total synthesis of (-)-goniotrionin

A stereoselective total synthesis of the reported structure of goniotrionin (4) has been accomplished. The key steps involved the opening of a chiral epoxide, a highly diastereoselective Mukaiyama aerobic oxidative cyclization, a selective 1,2-syn Mukaiyama aldol reaction, and a Noyori reduction.

Claisen rearrangements based on vinyl fluorides

2-Fluoroalk-1-en-3-ols (4), available from terminal alkenes (1) by bromofluorination, subsequent dehydrobromination of the 1-bromo-2-fluoroalkanes (2) to form 2-fluoroalkenes (3) and selenium dioxide mediated allylic oxidation with tert-butylhydroperoxide, undergo Johnson-Claisen rearrangement on treatment with trimethyl orthoacetate to give methyl 4-fluoroalk-4-enoates (7) in high yields. In contrast Ireland-Claisen rearrangement of 3-acetoxy-2-fluorodec-1-ene (9b) with triethylamine and TMSOTf in ether failed. Instead of the expected formation of a carboxylic acid, selective C-silylation of the α-position to the carboxyl group to form 14 occurred. However, Ireland-Claisen rearrangement was successful with corresponding chloroacetates 10 and propionates 11 of four 2-fluoroalk-1-en-3-ols (4) to give 2-chloro-4-fluoroalk- 4-enecarboxylic acids (15) or its 2-methyl derivatives 16, respectively, in moderate yields. These [3,3]-sigmatropic rearrangements are diastereoselective giving trans-configured double bonds, exclusively. Corresponding esters derived from (Z)-2-fluorocyclododec-2-enol (22), did rearrange to yield mixtures of diastereomers much less selectively. Also 2-fluorodec-2-enol (6), which was prepared by rearrangement of 2-fluoro-2-octyloxirane (5) with TMSOTf and triethylamine, was successfully applied as a starting material for [3,3]-sigmatropic rearrangements. The corresponding 3-(1-fluoroethenyl)alkanoic acid derivatives 17 and 18 were formed in moderate yield. 2-Fluoroalk-1-en-3-ol esters prepared in two steps from 2-fluoroalk-1-enes undergo Claisen rearrangements to form 2-substistuted 4-fluoroalk-4-enecarboxylic acids.