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5930-98-3 Usage

Chemical Properties

clear slightly yellow liquid

Uses

4-(Trimethylsilyl)-3-butyn-2-one (TMSB) has been used to investigate its asymmetric bioreduction to (S)-4-(trimethylsilyl)-3-butyn-2-ol {(S)-TMSBOL} by employing biocompatible water-immiscible ionic liquids (ILs). TMSB may be used for the synthesis of entecavir (BMS-200475).

General Description

4-(Trimethylsilyl)-3-butyn-2-one is a ketone. Its asymmetric bioreduction to enantiopure {(S)-TMSBOL in various hydrophilic ionic liquid (ILs) solvent systems has been reported.

Check Digit Verification of cas no

The CAS Registry Mumber 5930-98-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,9,3 and 0 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 5930-98:
(6*5)+(5*9)+(4*3)+(3*0)+(2*9)+(1*8)=113
113 % 10 = 3
So 5930-98-3 is a valid CAS Registry Number.
InChI:InChI=1/C14H15NO2/c1-8-7-11-9(2)15-13-10(14(11)17-8)5-4-6-12(13)16-3/h4-6,8H,7H2,1-3H3

5930-98-3 Well-known Company Product Price

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  • TCI America

  • (T2973)  4-(Trimethylsilyl)-3-butyn-2-one  >97.0%(GC)

  • 5930-98-3

  • 5mL

  • 590.00CNY

  • Detail
  • TCI America

  • (T2973)  4-(Trimethylsilyl)-3-butyn-2-one  >97.0%(GC)

  • 5930-98-3

  • 25mL

  • 1,790.00CNY

  • Detail
  • Aldrich

  • (418676)  4-(Trimethylsilyl)-3-butyn-2-one  97%

  • 5930-98-3

  • 418676-5G

  • 875.16CNY

  • Detail

5930-98-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names 4-trimethylsilylbut-3-yn-2-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5930-98-3 SDS

5930-98-3Synthetic route

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

2-(trimethylsilylethynyl)-1,3-dioxane

4-trimethylsilyl-3-butyn-2-one
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
trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

4-trimethylsilyl-3-butyn-2-one
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

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

acetyl chloride
75-36-5

acetyl chloride

A

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

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

B

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

4-trimethylsilyl-3-butyn-2-one

ethyl acetate
141-78-6

ethyl acetate

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

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

4-trimethylsilyl-3-butyn-2-one

(S)-4-trimethylsilyl-3-butyn-2-ol
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%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

Me2CuLi

Me2CuLi

4-trimethylsilylpent-3-en-2-one
81357-01-9

4-trimethylsilylpent-3-en-2-one

Conditions
ConditionsYield
In diethyl ether at -78℃;99%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

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

ethyl aminocrotonate

(4E)-2-amino-3-ethoxycarbonylhepta-2,4-dien-6-one
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%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

benzamidine monohydrochloride
1670-14-0

benzamidine monohydrochloride

4-methyl-2-phenylpyrimidine
34771-48-7

4-methyl-2-phenylpyrimidine

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

tert-butyl acetoacetate

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

4-trimethylsilyl-3-butyn-2-one

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

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%
1,1-bis(trimethylsiloxy)-2-methylprop-1-ene
31469-25-7

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

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

4-trimethylsilyl-3-butyn-2-one

3-hydroxy-2,2,3-trimethyl-5-(trimethylsilyl)pent-4-ynoic acid
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
5930-98-3

4-trimethylsilyl-3-butyn-2-one

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

tert-butyldimethyl(1-phenylvinyloxy)silane

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

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

Conditions
ConditionsYield
triphenylmethyl perchlorate In dichloromethane at -78℃; for 6h;97%
4-Amino-2,6-dihydroxypyrimidine
873-83-6

4-Amino-2,6-dihydroxypyrimidine

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

4-trimethylsilyl-3-butyn-2-one

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

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

Conditions
ConditionsYield
In dimethyl sulfoxide at 110℃; for 72h;97%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

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

4-trimethylsilanyl-butan-2-one

Conditions
ConditionsYield
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;
2,6-diamino-3H-pyrimidin-4-one
100643-27-4, 143504-99-8

2,6-diamino-3H-pyrimidin-4-one

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

4-trimethylsilyl-3-butyn-2-one

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

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

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 72h; Micheal addition;96%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

Dimethyl phosphite
868-85-9

Dimethyl phosphite

C9H19O4PSi

C9H19O4PSi

Conditions
ConditionsYield
With C34H36F4N4P(1+)*Cl(1-); potassium tert-butylate In tetrahydrofuran at -78℃; for 17h; Inert atmosphere; enantioselective reaction;96%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

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

4-trimethylsilyl-3-butyn-2-one

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

1-(2-(trimethylsilyl)-1,3-dithian-2-yl)propan-2-one

Conditions
ConditionsYield
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
6-amino-1-methyluracil
2434-53-9

6-amino-1-methyluracil

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

4-trimethylsilyl-3-butyn-2-one

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

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

Conditions
ConditionsYield
With zinc dibromide In dimethyl sulfoxide at 110℃; for 72h; Bohlmann-Rahtz heteroannulation;94%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

benzyl azide
622-79-7

benzyl azide

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

1-(1-benzyl-1H-1,2,3-triazol-4-yl)ethan-1-one

Conditions
ConditionsYield
With triethylamine; copper(I) bromide In N,N-dimethyl-formamide at 100℃; for 1.5h;94%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

Dimethylphenylsilane
766-77-8

Dimethylphenylsilane

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

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

Conditions
ConditionsYield
With bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In toluene at 20℃; for 14h; Inert atmosphere; optical yield given as %de; stereoselective reaction;94%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

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

Mes2P-C{=C(H)-Ph}-AltBu2

C41H57AlOPSi(1-)*H(1+)

C41H57AlOPSi(1-)*H(1+)

Conditions
ConditionsYield
In pentane at -50 - 20℃; for 2h; Inert atmosphere; Schlenk technique;94%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

2-hydrazino-4-(trifluoromethyl)pyrimidine

2-hydrazino-4-(trifluoromethyl)pyrimidine

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

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Reflux; Inert atmosphere;93%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

acetylacetone
123-54-6

acetylacetone

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

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

Conditions
ConditionsYield
With ammonium acetate; 1-methyl-1H-imidazolium trifluoroacetate at 20℃; for 24h; Bohlmann-Rahtz pyridine synthesis;92%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

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

ethyl aminocrotonate

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

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

Conditions
ConditionsYield
With zinc dibromide In toluene for 5h; Heating;90%
With acetic acid In toluene at 50℃; Bohlmann-Rahtz pyridine synthesis;79%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

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

ethyl (E)-3-aminobut-2-enoate

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

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

Conditions
ConditionsYield
With zinc dibromide In toluene for 5h; Bohlmann-Rahtz reaction; Heating;90%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

ethyl acetoacetate
141-97-9

ethyl acetoacetate

ethyl 2,6-dimethylnicotinate
1721-13-7

ethyl 2,6-dimethylnicotinate

Conditions
ConditionsYield
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%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

guanidine hydrochloride
50-01-1

guanidine hydrochloride

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

4-Methyl-pyrimidin-2-ylamin

Conditions
ConditionsYield
With sodium carbonate In acetonitrile at 120℃; for 0.666667h; microwave irradiation;90%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

methyl 2,6-dimethylpyridine-3-carboxylate

methyl 2,6-dimethylpyridine-3-carboxylate

Conditions
ConditionsYield
With ammonium acetate; 1-methyl-1H-imidazolium trifluoroacetate at 20℃; for 24h; Bohlmann-Rahtz pyridine synthesis;90%
carbon tetrabromide
558-13-4

carbon tetrabromide

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

4-trimethylsilyl-3-butyn-2-one

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

(4,4-dibromo-3-methylbut-3-en-1-yn-1-yl)trimethylsilane

Conditions
ConditionsYield
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%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

C35H30BF10P

C35H30BF10P

C42H42BF10OPSi

C42H42BF10OPSi

Conditions
ConditionsYield
In dichloromethane at 20℃; for 168h;89%
4-trimethylsilyl-3-butyn-2-one
5930-98-3

4-trimethylsilyl-3-butyn-2-one

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

5-((tert-butyldimethylsilyl)oxy)pent-3-yn-2-yl diethyl phosphate

Conditions
ConditionsYield
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;

5930-98-3Relevant articles and documents

Merging Asymmetric [1,2]-Additions of Lithium Acetylides to Carbonyls with Type II Anion Relay Chemistry

O'brien, Kevin T.,Smith, Amos B.

, p. 7655 - 7659 (2019)

An enantioselective three-component coupling reaction has been developed, enabling the union of a variety of lithium acetylides and electrophiles exploiting an achiral linchpin via an anionic reaction cascade. This Type II Anion Relay Chemistry tactic is initiated via an enantioselective [1,2]-carbonyl addition exploiting BINOL catalysis to access an enantioenriched alkoxide intermediate. Migration of charge across the linchpin via a [1,4]-Brook rearrangement with electrophile capture affords a three-component propargyl ether adduct. Herein, we report the development, scope, and limitations of this reaction sequence.

Phosphine-Catalyzed Intermolecular Annulations of Fluorinated ortho-Aminophenones with Alkynones – The Switchable [4+2] or [4+2]/[3+2] Cycloaddition

Zhang, Yanshun,Sun, Yaoliang,Wei, Yin,Shi, Min

supporting information, p. 2129 - 2135 (2019/03/13)

A phosphine-catalyzed intermolecular annulation reaction of functionalized ortho-aminoacetophenones with alkynones has been disclosed in this paper. A variety of 2-alkynylquinolines and benzo-fused indolizine were selectively afforded in moderate to good yields at different reaction temperatures and with different phosphine catalysts via the in situ generated zwitterionic intermediate derived from alkynone and phosphine. (Figure presented.).

Aerobic oxidation of propargylic alcohols to αβ,-unsaturated alkynals or alkynones catalyzed by fe(NOH, TEMPO and sodium chloride in toluene

Liu, Jinxian,Xie, Xi,Ma, Shengming

experimental part, p. 1569 - 1576 (2012/06/30)

A practical aerobic oxidation of propargylic alcohols using Fe(NOH, TEMPO and sodium chloride in toluene at room temperature was applied to various type of propargylic alcohols affording ,-unsaturated alkynals or alkynones in good to excellent yields. This protocol could be applied in academic laboratories as well as in industrial-scale production.

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