3-(Trimethylsilyl)-1,2-butadiene
Basic information
- CAS
74542-82-8- Standard SMILES
C=C=C(C)[Si](C)(C)C- InChIKey
BARFIQOXZWRCGW-UHFFFAOYSA-N- Molecular formula
- C7H14Si
- Average molar mass
- 126.27 g/mol
- Monoisotopic mass
- 126.08647698
Names & identifiers
- Preferred name
- 3-(Trimethylsilyl)-1,2-butadiene
- IUPAC
- buta-2,3-dien-2-yl(trimethyl)silane
- English name
- 1-Methyl-1-(trimethylsilyl)allene
- Molecular formula
- C7H14Si
- Molecular weight
- 126.27
Names & synonyms
3-(Trimethylsilyl)-1,2-butadieneRefChem:496459624-581-01-Methyl-1-(trimethylsilyl)allene74542-82-8Trimethyl(1-methyl-1,2-propadienyl)silaneNSC657832Silane,trimethyl(1-methyl-1,2-propadien-1-yl)-T7C73V8VZJNSC-657832NSC 657832UNII-T7C73V8VZJ
Show more names
Buta-2,3-Dien-2-Yl(Trimethyl)Silane3-(Trimethylsilyl)-1,2-butadiene 98%Silane, trimethyl(1-methyl-1,2-propadien-1-yl)-
SCHEMBL7126065CHEMBL1976857DTXSID70996067AKOS015912626(Buta-2,3-dien-2-yl)(trimethyl)silane(Buta-2,3-dien-2-yl)tri(methyl)silaneNCI60_020175trimethyl(1-methylpropa-1,2-dienyl)silane
Database identifiers
- CAS
74542-82-8- PubChem CID
- 376772
- DTXSID
DTXSID70996067- ChEMBL
CHEMBL1976857- UNII
- T7C73V8VZJ
- EC Number
- 624-581-0
- Nikkaji
- J587.462I
Properties
Computed structural properties
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 122
Physicochemical properties
- Boiling point
- 111 · 111-112 °C(lit.)
- Density
- 0.759 g/mL · 0.759 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.444(lit.)
- Flash point
- 19 °F · 19 °F
- solubility
- 2 Cl2, · sol CH2Cl2, benzene, THF, Et2O, and most organic solvents.
- FDA UNII
- 7 C73V8VZJ · T7C73V8VZJ
- Symbol(GHS)
- 2 · GHS02
- Signal word
- Danger
- Hazard statements
- 225 · H225
- Precautionary statements
- 210 · P210
- Hazard Codes
- F
- Risk Statements
- 11 · 11
- Safety Statements
- 16 · 16
- RIDADR
- 1993 · UN 1993 3/PG 2
- WGK Germany
- 3 · 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesFlam. Liq. 2 (100%)
Safety data
- wgk
- 3
- ridadr
- UN 1993 3/PG 2
- risk_code
- 11
- Signal word
- Danger
- Symbol(GHS)
- GHS02
- hazard_code
- F
- safety_code
- 16
- Hazard statements
- H225
- Precautionary statements
- P210
Chemistry & industry
Applications
UsesIt is widely used as propargylic anion equivalents; three-carbon synthons for [3 + 2] annulations leading to five-membered compounds including cyclopentenes,4 dihydrofurans, pyrrolines, isoxazoles, furans, and azulenes.
Uses3-(Trimethylsilyl)-1,2-butadiene may be used for the synthesis of γ-(trimethylsilyl)allylborane.
Preparation methods
Preparation1-methyl-1-(trialkylsilyl)allenes can be conveniently prepared by the method of Vermeer. Silylsubstituted propargyl mesylates thus undergo SN2 displacement by the organocopper reagent generated from methylmagnesium chloride, copper(I) bromide, and lithium bromide 1-Methyl-1-(trimethylsilyl)allene is produced in 52% yield from commercially available (trimethylsilyl)propargyl alcohol in this fashion (eq 1). The t-butyldimethylsilyl and triisopropylsilyl analogs are synthesized by the same method in 90% and 58% yield, respectively. Propargyl alcohols bearing these and other trialkylsilyl groups can be prepared by treatment of propargyl alcohol with n-butyllithium and the appropriate trialkylsilyl chloride. Allenylsilanes bearing other C-1 substituents can be prepared in an analogous manner by using the appropriate Grignard reagents.
Upstream & downstream products
Downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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