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003013

003013-1g



(Trimethylsilyl)acetylene


CAS Number: 1066-54-2
   
Molecular Formula: C5H10Si
   
Molecular Weight: 98.22
   
MDL Number: MFCD00008569


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003013-1g
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003013-5g
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003013-10g
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003013-25g
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003013-100g
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003013-500g
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Purity:98%
Bp:53°
Density:0.695
Refractive Index:1.3880
 
Pictograms:
Signal Word:Danger
Hazard Statements:H225, H302, H316
Precautionary Statements:P210, P233, P280
UN#:UN1993
Packing Group:II
Hazard Class:3
Flash Point:-34°
Risk Statements:11-36/37/38
Safety Statements:9-16-33-23-24/25-26-28-36/37/39
SDS: See MSDS
 
Limited Quantities:1.0 L (0.3 gallon) (liquid)
Excepted Quantities:Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

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An acetylene molecule protected on one end by the trimethylsilyl group. It is used in alkynylations, e.g. the Sonogashira reaction. Has been used as  substrate for nickel-catalyzed cross-coupling with benzonitriles,1 for pyrazole syntheses via 1,3-dipolar cycloaddition of diazo compounds to acetylenes,2 direct addition of TMS-acetylene to aldimines catalyzed by a commercially available Ir(I) complex,3 synthesis for the (Z)-14-methyl-9-pentadecenoic acid 4 and sonogashira coupling of a variety of para substituted aryl halides.5

1. Tetrahedron Lett. 2004, 45, 4989.
2. Heterocycles 2006, 68, 1961.
3. Org. Lett. 2001, 3, 4319.
4. ARKIVOC 2007, (viii), 49.
5. Green Chem. 2009, 11, 1821.

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