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Thermo Scientific Chemicals
1,9-Decadiyne, 97%
CAS: 1720-38-3 | C10H14 | 134.22 g/mol
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化學識別
CAS1720-38-3
IUPAC Namedeca-1,9-diyne
Molecular FormulaC10H14
InChI KeyILVDYAGPHFWNQI-UHFFFAOYSA-N
SMILESC#CCCCCCCC#C
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規格
規格表
規格表Refractive Index1.4480-1.4530 @ 20?C
Assay (GC)≥96.0%
FormLiquid
Appearance (Color)Clear colorless to yellow
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Insoluble in water.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents.
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.
Solubility
Insoluble in water.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents.
RUO – Research Use Only
General References:
- Haruki Okawa,; Motoyoshi Sekiya,; Junichiro Osawa,; Tatsuo Wada,; Akira Yamada,; Hiroyuki Sasabe,; Toshiyuki Uryu. A Nonlinear Optical Waveguide of Poly(1,9-decadiyne). Polymer Journal. 1991, 23 147-153.
- Christophe Feuvrie,; Jérôme Blanchet,; Martine Bonin,; Laurent Micouin. Synthesis and Reactivity of Mixed Alkynylalanes by Direct Triethylamine-Catalyzed Alumination of Terminal Alkyne. Org. Lett.,. 2004 , 6(14),2333-2336.