187437
Bis(trimethylsilyl)acetylene
99%
Synonym(s):
BTMSA
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About This Item
Linear Formula:
(CH3)3SiC≡CSi(CH3)3
CAS Number:
Molecular Weight:
170.40
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
238-671-9
Beilstein/REAXYS Number:
906870
MDL number:
Assay:
99%
Quality Segment
assay
99%
refractive index
n
bp
136-137 °C (lit.)
mp
21-24 °C (lit.)
density
0.752 g/mL at 25 °C (lit.)
storage temp.
2-8°C
SMILES string
C[Si](C)(C)C#C[Si](C)(C)C
InChI
1S/C8H18Si2/c1-9(2,3)7-8-10(4,5)6/h1-6H3
InChI key
ZDWYFWIBTZJGOR-UHFFFAOYSA-N
General description
Bis(trimethylsilyl)acetylene (BTMSA) participates as nucleophile in Friedel-Crafts type acylations and alkylations. BTMSA undergoes rhodium catalyzed addition reaction with diarylacetylenes. It undergoes cycloaddition with 1,5-hexadiynes in the presence of CpCo(CO)2 (Cp=cyclopentadienyl) to form benzocyclobutenes. Structure of BTMSA was characterized by a centre of inversion present on triple bond (length=1.208(3)Å). TiCl4-Et2AlCl catalyzed Diels-Alder reaction of BTMSA with norbornadiene has been reported.
Application
Bis(trimethylsilyl)acetylene (BTMSA) was used as starting reagent in the synthesis of functionalized 4-R-1,2-bis(trimethylsilyl)benzenes. It was also used in the synthesis of (+)-brasilenyne and (β-diketanato)Ag(BTMSA).
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
35.6 °F - closed cup
flash_point_c
2 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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