1720-38-3

Basic information

• Product Name: 1,9-DECADIYNE
• Synonyms: TIMTEC-BB SBB008879;1,9-DECADIYNE;Decadiyne;deca-1,9-diyne;1,9-Decadiyne, 97+%;1,9-Decadiyne (6CI, 7CI, 8CI, 9CI);1,9-Decanediyne;1,9-Decadiyne,98%
• CAS NO: 1720-38-3
• Molecular Formula: C₁₀H₁₄
• Molecular Weight: 134.22
• EINECS: 217-012-9
• Product Categories: Acetylenes;Acetylenic Hydrocarbons
• Mol File: 1720-38-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: -6.35°C (estimate)
• Boiling Point: 80-81 °C (10 mmHg)
• Flash Point: 60°C
• Appearance: Clear yellow/Liquid
• Density: 0.822
• Vapor Pressure: 1.04mmHg at 25°C
• Refractive Index: 1.449-1.453
• Storage Temp.: Flammables area
• Water Solubility: Insoluble in water.
• BRN: 1734594
• CAS DataBase Reference: 1,9-DECADIYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,9-DECADIYNE(1720-38-3)
• EPA Substance Registry System: 1,9-DECADIYNE(1720-38-3)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: 1993
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 1720-38-3(Hazardous Substances Data)

Usage

Chemical Properties

Clear yellow liquid

Uses

One-step synthesis of carbametacyclophane 3 from 1,9-decadiyne and diethyl acetylenedicarboxylate is described. The use of 1,9-decadiyne as a nucleophile led only to the monoalkynylation product, a selectivity that would be difficult to achieve with a catalytic in situ metalation process. 1,9-decadiyne reacts with iodobenzene (excess) to afford the bis-Sonogashira coupling product in excellent yield. 1,9-Decadiyne was dihydrated and gave 2,9-decanedione in 92% yield.

InChI:InChI=1/C10H14/c1-3-5-7-9-10-8-6-4-2/h1-2H,5-10H2

Upstream product

• 629-03-8 1 ,6-dibromohexane 
• 1066-26-8 sodium acetylide 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 1647-16-1 1,10-decadiene 
• 629-09-4 1,6-diiodohexane 
• 88736-98-5 1,10-bis(trimethylsilyl)-1,9-decadiyne 
• 110-52-1 1,4-dibromo-butane 
• 106-96-7 propargyl bromide 

Downstream Products

• 102747-75-1 1,6-bis-(3-phenyl-isoxazol-5-yl)-hexane 
• 1647-16-1 1,10-decadiene 
• 69300-15-8 2-methyl-decanenitrile 
• 16538-91-3 decane-2,9-dione 
• 45037-67-0 decanedial 
• 31699-38-4 dodeca-2,10-diyne 
• 1022081-30-6 C₂₈H₂₆O₂ 
• 49769-20-2 1,10-diphenyl-1,9-decadiyne 

Relevant articles and documents

Cyclic Diynes by Alkyne Metathesis

The preparation of α,ω-diynes with methyl groups at the termini (11a-i) is described. The methylene groups between the alkyne units vary between n = 12 (a) and n = 4 (i). Ring closing metathesis with Mo(CO) 6/CF3C6H4OH yielded the monocyclic alkyne 12a with 11a as starting material, whereas 11b-g yielded the cyclic diynes 13b-g. Detailed structural parameters were obtained for 13b and 13c by X-ray crystallography.

Intramolecular cyclohexadienone annulations of fischer carbene complexes: Model studies for the synthesis of phomactins

The intramolecular cyclohexadienone annulation of chromium carbene complexes is examined as a method to provide general access to the Phomactin family of natural products. The importance of the stereochemistry of the carbene complex and the number of carbons in the tether connecting the carbene complex and the alkyne are probed. Additionally, the degree of the 1,4-asymmetric induction is examined.