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4-(Trimethylsilyl)-3-butyn-2-one
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Name

4-(Trimethylsilyl)-3-butyn-2-one

 EINECS 628-294-1
CAS No. 5930-98-3 Density 0.875 g/cm3
PSA 17.07000 LogP 1.45620
Solubility N/A Melting Point 99 °C
Formula C7H12OSi Boiling Point 144.6 °C at 760 mmHg
Molecular Weight 140.257 Flash Point 41.2 °C
Transport Information UN 1224 3/PG 3 Appearance clear slightly yellow liquid
Safety 16-26-36-37/39 Risk Codes 10-36/37/38
Molecular Structure Molecular Structure of 5930-98-3 (4-(Trimethylsilyl)-3-butyn-2-one) Hazard Symbols IrritantXi
Synonyms

Methyltrimethylsilylethynyl ketone;4-(Trimethylsilyl)-3-butyn-2-one;1-(Trimethylsilyl)-1-butyn-3-one;(Acetylethynyl)trimethylsilane;

Article Data 34

4-(Trimethylsilyl)-3-butyn-2-one Synthetic route

86934-41-0

2-(trimethylsilylethynyl)-1,3-dioxane

5930-98-3

4-trimethylsilyl-3-butyn-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) BuLi / 1.) THF, -65 deg C, 30 min; 2.) THF, overnight, -65 deg C to 25 deg C
2: 63 percent / H2SO4 / acetone; H2O / 5 h / Heating
View Scheme
1066-54-2

trimethylsilylacetylene

5930-98-3

4-trimethylsilyl-3-butyn-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) THF, EtMgBr, RT, 1 h; 2.) diethyl ether, -25 deg C for 45 min then 1 h at RT then 15 min at 30 deg C
2: 81 percent / p-toluenesulfonic acid / benzene / Heating
3: 1.) BuLi / 1.) THF, -65 deg C, 30 min; 2.) THF, overnight, -65 deg C to 25 deg C
4: 63 percent / H2SO4 / acetone; H2O / 5 h / Heating
View Scheme
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / 0 °C / Schlenk technique
1.2: 12 h / 0 - 20 °C / Schlenk technique
2.1: Dess-Martin periodane / dichloromethane / 0.5 h / 0 °C
View Scheme

(η5-C5H4Si(CH3)3)2Ti(CCC(CH3)3)2CuCCSi(CH3)3

75-36-5

acetyl chloride

A

((C5H4Si(CH3)3)2Ti(CCC(CH3)3)2)CuCl

B

5930-98-3

4-trimethylsilyl-3-butyn-2-one

141-78-6

ethyl acetate

1066-54-2

trimethylsilylacetylene

5930-98-3

4-trimethylsilyl-3-butyn-2-one

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: ethyl acetate With boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
5930-98-3

4-trimethylsilyl-3-butyn-2-one

6999-19-5, 103253-60-7, 121522-26-7, 121522-27-8

(S)-4-trimethylsilyl-3-butyn-2-ol

Conditions
ConditionsYield
With potassium hydroxide; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide In isopropyl alcohol at 28℃; for 12h;99%
Stage #1: 4-trimethylsilyl-3-butyn-2-one With (R)-(+)-3,3'-bis(4-fluorophenyl)-[1,1'-binaphthalene]-2,2'-diol; dibutylmagnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; lithium chloride In n-heptane; toluene at -40℃; for 3h; Inert atmosphere; Sealed tube;
Stage #2: With methanol In n-heptane; toluene at -40 - 20℃; for 0.5h; Inert atmosphere; Sealed tube; enantioselective reaction;		98%
With formic acid; triethylamine; N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide In dichloromethane at 10 - 20℃; Inert atmosphere;96%
5930-98-3

4-trimethylsilyl-3-butyn-2-one

Me2CuLi

Me2CuLi

81357-01-9

4-trimethylsilylpent-3-en-2-one

Conditions
ConditionsYield
In diethyl ether at -78℃;99%
5930-98-3

4-trimethylsilyl-3-butyn-2-one

626-34-6, 7318-00-5, 41867-20-3

ethyl aminocrotonate

480453-20-1

(4E)-2-amino-3-ethoxycarbonylhepta-2,4-dien-6-one

Conditions
ConditionsYield
In ethanol at 50℃; for 5h; Michael addition;98%
In ethanol at 50℃; for 6h; Michael addition;82%
5930-98-3

4-trimethylsilyl-3-butyn-2-one

1670-14-0

benzamidine monohydrochloride

34771-48-7

4-methyl-2-phenylpyrimidine

Conditions
ConditionsYield
With sodium carbonate In acetonitrile at 120℃; for 0.666667h; microwave irradiation;98%
1694-31-1

tert-butyl acetoacetate

5930-98-3

4-trimethylsilyl-3-butyn-2-one

2-methyl-2-propyl 2,6-dimethylpyridine-3-carboxylate

Conditions
ConditionsYield
With ammonium acetate In ethanol for 24h; Bohlmann-Rahtz reaction; Heating;98%
With ammonium acetate In ethanol for 24h; Heating;98%
31469-25-7

1,1-bis(trimethylsiloxy)-2-methylprop-1-ene

5930-98-3

4-trimethylsilyl-3-butyn-2-one

1448604-95-2

3-hydroxy-2,2,3-trimethyl-5-(trimethylsilyl)pent-4-ynoic acid

Conditions
ConditionsYield
Stage #1: 4-trimethylsilyl-3-butyn-2-one With boron trifluoride diethyl etherate In diethyl ether at 0℃; for 0.05h; Inert atmosphere;
Stage #2: 1,1-bis(trimethylsiloxy)-2-methylprop-1-ene In diethyl ether at 0 - 20℃; for 4h; Inert atmosphere;		98%

4-(Trimethylsilyl)-3-butyn-2-one Chemical Properties


Systematic Name: 4-(Trimethylsilyl)but-3-yn-2-one
SMILES: O=C(C#C[Si](C)(C)C)C 
InChI: InChI=1/C7H12OSi/c1-7(8)5-6-9(2,3)4/h1-4H3 
InChIKey: NQEZDDPEJMKMOS-UHFFFAOYAH 
Empirical Formula: C7H12OSi
Molecular Weight: 140.2551 
Index of Refraction: 1.428
Molar Refractivity: 41.23 cm3
Molar Volume: 160.2 cm3
Surface Tension: 23.5 dyne/cm
Density: 0.875 g/cm3
Flash Point: 41.2 °C
Enthalpy of Vaporization: 38.16 kJ/mol
Boiling Point: 144.6 °C at 760 mmHg
Vapour Pressure: 5.06 mmHg at 25 °C
Product Categories: Alkynes; Internal; Organic Building Blocks
storage temp. of 4-(Trimethylsilyl)-3-butyn-2-one (CAS NO.5930-98-3): Flammables area

4-(Trimethylsilyl)-3-butyn-2-one Safety Profile

Hazard Codes:IrritantXi
Risk Statements: 10-36/37/38 
R10:Flammable. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 16-26-36-37/39 
S16:Keep away from sources of ignition. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.
RIDADR: UN 1224 3/PG 3
WGK Germany of 4-(Trimethylsilyl)-3-butyn-2-one (CAS NO.5930-98-3): 3

4-(Trimethylsilyl)-3-butyn-2-one Specification

 4-(Trimethylsilyl)-3-butyn-2-one (CAS NO.5930-98-3), its Synonyms are 3-Butyn-2-one, 4-(trimethylsilyl)- ; 4-(Trimethylsilyl)but-3-yn-2-one . It is clear slightly yellow liquid.

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