Bis(trimethylsilyl)acetylene

HCID 84564
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Basic information

CAS
14630-40-1
Standard SMILES
C[Si](C)(C)C#C[Si](C)(C)C
InChIKey
ZDWYFWIBTZJGOR-UHFFFAOYSA-N
Molecular formula
C8H18Si2
Average molar mass
170.4 g/mol
Monoisotopic mass
170.09470364

Names & identifiers

Preferred name
Bis(trimethylsilyl)acetylene
IUPAC
trimethyl(2-trimethylsilylethynyl)silane
English name
Bis(trimethylsilyl)acetylene
Molecular formula
C8H18Si2
Molecular weight
170.4

Names & synonyms

Bis(trimethylsilyl)acetylene14630-40-1Silane, 1,2-ethynediylbis[trimethyl-ethyne-1,2-diylbis(trimethylsilane)Silane, 1,1'-(1,2-ethynediyl)bis[1,1,1-trimethyl-EINECS 238-671-9Silane, 1,2-ethynediylbis(trimethyl-DTXSID3065798Silane, 1,1'-(1,2-ethynediyl)bis(1,1,1-trimethyl-RefChem:569326DTXCID6034764Silane, 1,2ethynediylbis(trimethyl
Show more names
BSTMABis(trimethylsilyl)ethyneDK079DK080ICLA-002TIMTEC-BB SBB008997Ethynylbistrimethylsilanel
Silane, 1,1'(1,2ethynediyl)bis(1,1,1trimethyl238-671-9InChI=1/C8H18Si2/c1-9(2,3)7-8-10(4,5)6/h1-6H1,2-Bis(trimethylsilyl)ethynetrimethyl(2-trimethylsilylethynyl)silaneBTMSAC8H18Si21,2-bis-trimethylsilanyl-ethyne

Database identifiers

CAS
14630-40-1
PubChem CID
84564
DTXSID
DTXSID3065798
EC Number
238-671-9
Nikkaji
J2.272.452E、J47.009K

Properties

Computed structural properties

Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
2
Heavy atoms
10

Experimental & physicochemical properties

Chemical ClassesMetals -> Metalloid Compounds (Silicon)
SpringerMaterials Properties29Si nuclear magnetic resonance spectrum
Physical DescriptionClear colorless liquid; mp = 21-24 deg C; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
21 · 21-24 °C(lit.)
Boiling point
136 · 136-137 °C(lit.)
Density
0.752 g/mL · 0.752 g/mL at 25 °C(lit.)
refractive index
20 · n20/D 1.427(lit.)
Flash point
29 °C · 29 °C
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H225 (83.7%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationBis(trimethylsilyl)acetylene: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin and strong eye irritant; [Sigma-Aldrich MSDS] See Trimethylsilylacetylene and 1-Phenyl-2-(trimethylsilyl)acetylene.
Hazard Classes and CategoriesFlam. Liq. 2 (83.7%)

Safety data

F
10
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
ridadr
UN 1993 3/PG 2
hs_code
29310095

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationSilane, 1,1'-(1,2-ethynediyl)bis[1,1,1-trimethyl-: ACTIVE
Applications · 3 items

UsesIn the presence of CpCo(CO)2 (cat. no. 245259), undergoes cycloaddition with 1,5-hexadiynes to form benzocyclobutenes.1

UsesBTMSA is used as starting reagent in the synthesis of functionalized 4-R-1,2-bis(trimethylsilyl)benzenes. It is also used in the synthesis of (+)-brasilenyne2 and (β-diketanato)Ag(BTMSA). Bis(trimethylsilyl)acetylene is a ligand that binds to a central metal ion (e.g. Titanium) to create a coordination complex. One of its complexes, Permethyltitanocene-bis(trimethylsilyl)acetylene, is a catalyst for the head-to-tail dimerization of 1-alkynes (e.g. 3-Penten-1-yne [P227430]).

General DescriptionBis(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)). TiCl4-Et2AlCl catalyzed Diels-Alder reaction of BTMSA with norbornadiene has been reported.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]

Related reactions

42 records
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Compound notes

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