(TRIISOPROPYLSILYL)ACETYLENE

(TRIISOPROPYLSILYL)ACETYLENE Basic information

Product Name:	(TRIISOPROPYLSILYL)ACETYLENE
Synonyms:	(TRIISOPROPYLSILYL)ACETYLENE;(Triisopropylsilyl)Acetylene 98+%;(Triisopropylsilyl)acetylene,Ethynyltriisopropylsilane;(TRIISOPROPYLSILYL)ACETYLENE 97%;Triiopropyl silyl acetylene;[Tris(isopropyl)silyl]acetylene;Ethynyl[tris(isopropyl)]silane, Ethynyl[tris(prop-2-yl)]silane;(Triisopropylsilyl)acetylene, 97% 25GR
CAS:	89343-06-6
MF:	C11H22Si
MW:	182.38
EINECS:	629-580-9
Product Categories:	Acetylenes;Ethynylsilanes;Functionalized Acetylenes;Si (Classes of Silicon Compounds);Si-(C)4 Compounds
Mol File:	89343-06-6.mol

(TRIISOPROPYLSILYL)ACETYLENE Chemical Properties

Melting point	50-51 °C
Boiling point	50-52 °C/0.6 mmHg (lit.)
density	0.813 g/mL at 25 °C (lit.)
refractive index	n20/D 1.4527(lit.)
Fp	133 °F
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
solubility	Miscible with organic solvents.
form	liquid
color	Clear, colourless
Specific Gravity	0.813
Hydrolytic Sensitivity	4: no reaction with water under neutral conditions
BRN	3536241
InChIKey	KZGWPHUWNWRTEP-UHFFFAOYSA-N
CAS DataBase Reference	89343-06-6(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36/37/39-37/39
RIDADR	UN 1993 3/PG 3
WGK Germany	3
TSCA	N
HazardClass	3.2
PackingGroup	III
HS Code	29319090

MSDS Information

Provider	Language
ACROS	English
SigmaAldrich	English

(TRIISOPROPYLSILYL)ACETYLENE Usage And Synthesis

Chemical Properties	clear colorless liquid
Physical properties	colorless clear liquid; bp 50–52 °C at 0.8 hPa (0.6 mmHg), flash point 56 °C (closed cup); d = 0.813.
Uses	(Triisopropylsilyl)acetylene (TIPS-acetylene) is an easily handled and inexpensive monoprotected acetylene used as an attractive substitute for trimethylsilylacetylene (TMSacetylene). The bulkier silyl protecting group of TIPS-acetylene provides stability in a wider range of reaction conditions than TMS-acetylene. Its higher boiling point also provides better handling and safety than TMS-acetylene (bp 87–88°C at 12 hPa (9 mmHg)). The general utility of TIPS-acetylene is often highlighted in the transition metal-catalyzed C–C bond formations， including but not limited to transition metal-catalyzed Coupling Reactions；Reaction of TIPS-acetylide with Electrophiles；Synthesis of Polyynes；Transition Metal-catalyzed Cross-addition of TIPSacetylene to Alkynes；Hydroalkynylation；Direct Alkynylation；Conjugate Addition；Cycloaddition；Ring-opening Reactions etc.
Uses	(Triisopropylsilyl)acetylene may be used as reagent for the rhodium-catalyzed asymmetric alkynylation of various α,β-unsaturated ketones. It may be used as reagent in the enantioselective synthesis of β-alkynylated nitroalkanes.
General Description	Asymmetric addition of (triisopropylsilyl)acetylene to α,β,γ,δ-unsaturated carbonyl compounds in the presence of a cobalt/Duphos catalyst is reported. A Sonogashira coupling reaction between 1-bromo-3-iodo-5-tertbutylbenzene and (triisopropylsilyl)acetylene is reported.

(TRIISOPROPYLSILYL)ACETYLENE Preparation Products And Raw materials

Preparation Products

5-Ethynylisophthalic acid-->4-ETHYNYLBENZYL ALCOHOL 97-->(3-(1-(triisopropylsilyl)-5-(triMethylsilyl) penta-1,4-diyn-3-ylidene)penta-1,4-diyne- 1,5-diyl)bis(triisopropylsilane)-->TIPS-anthracene-->(3-(dibroMoMethylene)-5-(triisopropylsilyl) penta-1,4-diynyl)triMethylsilane-->1,3-Cyclopentadiene-1,3-dicarboxylic acid, 2,4-dimethyl-5-[[tris(1-methylethyl)silyl]methylene]-, 1,3-diethyl ester

(TRIISOPROPYLSILYL)ACETYLENE

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