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

Name
4-(Trimethylsilyl)-3-butyn-2-one
EINECS 628-294-1
CAS No. 5930-98-3
Article Data34
CAS DataBase
Density 0.875 g/cm³
Solubility
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
Hazard Symbols Xi
Synonyms Methyltrimethylsilylethynyl ketone;4-(Trimethylsilyl)-3-butyn-2-one;1-(Trimethylsilyl)-1-butyn-3-one;(Acetylethynyl)trimethylsilane;
PSA 17.07000
LogP 1.45620

Synthetic route

: 86934-41-0
2-(trimethylsilylethynyl)-1,3-dioxane

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

Conditions

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 141-78-6
ethyl acetate

: 1066-54-2
trimethylsilylacetylene

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 66324-10-5
tert-butyldimethyl(1-phenylvinyloxy)silane

: 122124-63-4
3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-1-phenyl-5-trimethylsilanyl-pent-4-yn-1-one

Conditions

Conditions	Yield
triphenylmethyl perchlorate In dichloromethane at -78℃; for 6h;	97%

: 873-83-6
4-Amino-2,6-dihydroxypyrimidine

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 6-amino-5-(3-oxo-but-1-enyl)-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
In dimethyl sulfoxide at 110℃; for 72h;	97%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 13506-88-2
4-trimethylsilanyl-butan-2-one

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In pentane at 20℃; under 760.051 Torr; for 20h;	97%
With palladium on activated charcoal; hydrogen In pentane at 10℃; for 12h;

: 100643-27-4, 143504-99-8
2,6-diamino-3H-pyrimidin-4-one

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: E-2,4-diamino-5-(3-oxobut-1-enyl)pyrimidine-6-one

Conditions

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 72h; Micheal addition;	96%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 868-85-9
Dimethyl phosphite

: C9H19O4PSi

Conditions

Conditions	Yield
With C34H36F4N4P(1+)*Cl(1-); potassium tert-butylate In tetrahydrofuran at -78℃; for 17h; Inert atmosphere; enantioselective reaction;	96%

: 109-80-8
1.3-propanedithiol

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 1023592-10-0
1-(2-(trimethylsilyl)-1,3-dithian-2-yl)propan-2-one

Conditions

Conditions	Yield
magnesium oxide In tetrahydrofuran at 20℃; for 1h; double Michael addition;	95%
With potassium tert-butylate In tert-butyl alcohol at 0 - 20℃; Inert atmosphere;	35%
With potassium tert-butylate In isopropyl alcohol at 0℃; for 1h; Inert atmosphere;	4.8 g

: 2434-53-9
6-amino-1-methyluracil

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 1,7-dimethyl-1H-pyrido[2,3-d]pyrimidine-2,4-dione

Conditions

Conditions	Yield
With zinc dibromide In dimethyl sulfoxide at 110℃; for 72h; Bohlmann-Rahtz heteroannulation;	94%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 622-79-7
benzyl azide

: 80819-67-6
1-(1-benzyl-1H-1,2,3-triazol-4-yl)ethan-1-one

Conditions

Conditions	Yield
With triethylamine; copper(I) bromide In N,N-dimethyl-formamide at 100℃; for 1.5h;	94%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 766-77-8
Dimethylphenylsilane

: 1360896-21-4
(E)-3-dimethyl(phenyl)silyl-4-trimethylsilyl-3-buten-2-one

Conditions

Conditions	Yield
With bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In toluene at 20℃; for 14h; Inert atmosphere; optical yield given as %de; stereoselective reaction;	94%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 1308317-96-5, 1308318-08-2
Mes2P-C{=C(H)-Ph}-AltBu2

: C41H57AlOPSi(1-)*H(1+)

Conditions

Conditions	Yield
In pentane at -50 - 20℃; for 2h; Inert atmosphere; Schlenk technique;	94%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 2-hydrazino-4-(trifluoromethyl)pyrimidine

: (Z)-4-(trifluoromethyl)-2-(2-(4-(trimethylsilyl)but-3-yn-2-ylidene)hydrazinyl)pyrimidine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene Reflux; Inert atmosphere;	93%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 123-54-6
acetylacetone

: 1721-25-1
1-(2,6-dimethylpyridin-3-yl)ethan-1-one

Conditions

Conditions	Yield
With ammonium acetate; 1-methyl-1H-imidazolium trifluoroacetate at 20℃; for 24h; Bohlmann-Rahtz pyridine synthesis;	92%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 626-34-6, 7318-00-5, 41867-20-3
ethyl aminocrotonate

: Ethyl 2,6-dimethyl-4-(trimethylsilyl)pyridine-3-carboxylate

Conditions

Conditions	Yield
With zinc dibromide In toluene for 5h; Heating;	90%
With acetic acid In toluene at 50℃; Bohlmann-Rahtz pyridine synthesis;	79%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 41867-20-3
ethyl (E)-3-aminobut-2-enoate

: Ethyl 2,6-dimethyl-4-(trimethylsilyl)pyridine-3-carboxylate

Conditions

Conditions	Yield
With zinc dibromide In toluene for 5h; Bohlmann-Rahtz reaction; Heating;	90%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 141-97-9
ethyl acetoacetate

: 1721-13-7
ethyl 2,6-dimethylnicotinate

Conditions

Conditions	Yield
With ammonium acetate In ethanol for 24h; Bohlmann-Rahtz reaction; Heating;	90%
With ammonium acetate In ethanol for 24h; Heating;	90%
With ammonium acetate; acetic acid In toluene for 20h; Heating;	75%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 50-01-1
guanidine hydrochloride

: 108-52-1
4-Methyl-pyrimidin-2-ylamin

Conditions

Conditions	Yield
With sodium carbonate In acetonitrile at 120℃; for 0.666667h; microwave irradiation;	90%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 105-45-3
acetoacetic acid methyl ester

: methyl 2,6-dimethylpyridine-3-carboxylate

Conditions

Conditions	Yield
With ammonium acetate; 1-methyl-1H-imidazolium trifluoroacetate at 20℃; for 24h; Bohlmann-Rahtz pyridine synthesis;	90%

: 558-13-4
carbon tetrabromide

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 1086594-82-2
(4,4-dibromo-3-methylbut-3-en-1-yn-1-yl)trimethylsilane

Conditions

Conditions	Yield
With triphenylphosphine In dichloromethane at 20℃; under 75.0075 Torr;	90%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.166667h; Stage #2: 4-trimethylsilyl-3-butyn-2-one In dichloromethane at 0 - 20℃;	89%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: C35H30BF10P

: C42H42BF10OPSi

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 168h;	89%

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 121522-26-7
5-((tert-butyldimethylsilyl)oxy)pent-3-yn-2-yl diethyl phosphate

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; (R)-Chirald In diethyl ether at -78℃; for 5h;	86%
With [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2, 3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]-ruthenium In dichloromethane; isopropyl alcohol at 20℃; for 2h; Inert atmosphere;	85%
With isopropyl alcohol; NADPH Lactobacillus kefir dehydrogenase, 50 mM phosphate 2 mM magnesium chloride buffer, pH 7.1;	25%
With NADP; magnesium chloride; rec Lactobacillus brevis alcohol dehydrogenase In sodium hydroxide; triethylamine; isopropyl alcohol at 20℃; for 16h; pH=6.5;

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: Irritant Xi
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.

Product Name

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

Synthetic route

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

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

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

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