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4-Hydroxy-2-butanone, also known as Glycerol, is a colorless to pale yellow liquid that is an important pharmaceutical intermediate. It is a beta-hydroxy ketone that is butan-2-one substituted by a hydroxy group at position 4. The gas phase reaction of the OH radicals with 4-hydroxy-2-butanone has been investigated by the absolute rate method.

590-90-9

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590-90-9 Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-2-butanone is used as a pharmaceutical intermediate for the preparation of fused benzazepine molecules, which are selective D3 receptor antagonists with pharmaceutical activity. It is also used in the preparation of verrucarin and mevalonic acid lactone, further contributing to its importance in the pharmaceutical field.
Used in Chemical Industry:
4-Hydroxy-2-butanone is used as a chemical intermediate for the preparation of 3-buten-2-one through dehydration over an anatase titanium dioxide catalyst. This application highlights its versatility in chemical synthesis and its role in the production of various compounds.
Used in Synthesis of Specific Compounds:
4-Hydroxy-2-butanone is used as a key component in the synthesis of 4-methyl-5-hydroxymethylthiazole, (±)-lineatin, and beta-hydroxylactones. These compounds have various applications in different industries, showcasing the diverse utility of 4-Hydroxy-2-butanone in chemical synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 590-90-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 0 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 590-90:
(5*5)+(4*9)+(3*0)+(2*9)+(1*0)=79
79 % 10 = 9
So 590-90-9 is a valid CAS Registry Number.
InChI:InChI=1/C4H8O2/c1-4(6)2-3-5/h5H,2-3H2,1H3

590-90-9 Well-known Company Product Price

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  • Alfa Aesar

  • (L11456)  4-Hydroxy-2-butanone, 95%   

  • 590-90-9

  • 25g

  • 258.0CNY

  • Detail
  • Alfa Aesar

  • (L11456)  4-Hydroxy-2-butanone, 95%   

  • 590-90-9

  • 100g

  • 696.0CNY

  • Detail

590-90-9SDS

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-hydroxybutan-2-one

1.2 Other means of identification

Product number -
Other names 2-Butanone, 4-hydroxy-

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:590-90-9 SDS

590-90-9Synthetic route

1-butyn-4-ol
927-74-2

1-butyn-4-ol

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With silver hexafluoroantimonate; disodium chloro[1,3-bis(2,6-diisopropyl-4-sodiumsulfonatophenyl)imidazol-2-ylidene]gold(I); water at 60℃; for 2h;99%
With 2CHF3O3S*C29H35NO6P2Pt; water; sodium dodecyl-sulfate at 80℃; Micellar solution;11 %Chromat.
With cis-dichlorido[1-(3-sodiumsulfonatepropyl)-3-(2,4,6-trimethylphenyl)imidazol-2-ylidene](dimethylsulfoxide)platinum(II); water at 80℃; for 24h; Inert atmosphere; Schlenk technique;23 %Spectr.
2-(2-methyl-1,3-dioxolan-2-yl)ethanol
5754-32-5

2-(2-methyl-1,3-dioxolan-2-yl)ethanol

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With oxalic acid; silica gel In dichloromethane Ambient temperature;98%
With cerium(III) chloride; sodium iodide In acetonitrile for 21h; Ambient temperature;91%
With oxalic acid; silica gel In dichloromethane at 20℃;87%
3-oxobutyraldehyde
625-34-3

3-oxobutyraldehyde

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With bis(η5-cyclopentadienyl)hafnium dihydride In isopropyl alcohol at 80℃; for 8h; Product distribution; other dicarbonyl compounds, α,β-unsaturated carbonyl compounds; other temperature; other group IVA metallocene complexes;95%
With bis(η5-cyclopentadienyl)hafnium dihydride In isopropyl alcohol at 80℃; for 8h;95%
formaldehyd
50-00-0

formaldehyd

acetone
67-64-1

acetone

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With D-Prolin at 20℃; for 24h; Reagent/catalyst; Inert atmosphere;92.3%
ambersep 900 OH at 50℃; for 23.5h; Product distribution / selectivity;13%
Amberlyst A 26 OH at 50℃; for 23.5h; Product distribution / selectivity;10%
tert-butyldimethylsilyl 4-phenylbutyl ether
72064-43-8

tert-butyldimethylsilyl 4-phenylbutyl ether

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With sodium periodate In tetrahydrofuran; water at 25℃;92%
4-(tert-butyldimethylsilyloxy)butan-2-one
120591-36-8

4-(tert-butyldimethylsilyloxy)butan-2-one

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With sodium periodate In tetrahydrofuran; water at 25℃;92%
1.3-butanediol
18826-95-4, 107-88-0

1.3-butanediol

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 4.25h; Oxidation;90%
With 3,3-dimethyldioxirane In acetone90%
With sodium bromate; sodium hydrogensulfite In acetonitrile for 2h; Heating;90%
1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

acetone
67-64-1

acetone

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With magnesium hydroxide; water In methanol at 50℃; for 10h; Reagent/catalyst; Temperature; Sealed tube;82%
2-hydroxy-3-butene
598-32-3

2-hydroxy-3-butene

A

acetaldol
107-89-1

acetaldol

B

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

C

3-hydroxy-2-butanon
513-86-0, 52217-02-4

3-hydroxy-2-butanon

D

methyl vinyl ketone
78-94-4

methyl vinyl ketone

E

crotonaldehyde
123-73-9

crotonaldehyde

Conditions
ConditionsYield
With hydrogenchloride; lithium tetrachloropalladate(II); p-benzoquinone In water at 25℃; for 0.5h; Rate constant; Mechanism; Kinetics; equilibrium constants;A 8%
B 10%
C 79%
D 0.7%
E 2.3%
2-hydroxy-3-butene
598-32-3

2-hydroxy-3-butene

A

acetaldol
107-89-1

acetaldol

B

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

C

3-hydroxy-2-butanon
513-86-0, 52217-02-4

3-hydroxy-2-butanon

D

crotonaldehyde
123-73-9

crotonaldehyde

Conditions
ConditionsYield
hydrogenchloride; lithium tetrachloropalladate(II); p-benzoquinone In water at 25℃; for 0.5h; Further byproducts given;A 8%
B 10%
C 79%
D 2.3%
4-(benzyloxy)-2-butanone
6278-91-7

4-(benzyloxy)-2-butanone

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate under 760 Torr; Ambient temperature;71%
homoalylic alcohol
627-27-0

homoalylic alcohol

A

2-isopropoxytetrahydrofuran
20191-91-7

2-isopropoxytetrahydrofuran

B

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

C

tetrahydrofuran-2'-yl ether
71780-57-9

tetrahydrofuran-2'-yl ether

Conditions
ConditionsYield
With oxygen; copper dichloride; Pd(MeCN)2Cl(NO2) 1.) 55 deg C, 2 h; 2.) 30 deg C, 3 h;A n/a
B 70%
C n/a
homoalylic alcohol
627-27-0

homoalylic alcohol

isopropyl alcohol
67-63-0

isopropyl alcohol

A

2-isopropoxytetrahydrofuran
20191-91-7

2-isopropoxytetrahydrofuran

B

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

C

tetrahydrofuran-2'-yl ether
71780-57-9

tetrahydrofuran-2'-yl ether

Conditions
ConditionsYield
With oxygen; copper dichloride; Pd(MeCN)2Cl(NO2) 1.) 55 deg C, 2 h; 2.) 30 deg C, 3 h;A n/a
B 70%
C n/a
1.3-butanediol
18826-95-4, 107-88-0

1.3-butanediol

A

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

B

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With crosslinked poly-4-vinylpyridine hydrobromide In acetonitrile at 50℃; for 21.5h; electric current, 60mA, 10-30V; Yield given;A n/a
B 59%
(E/Z)-2-buten-1-ol
6117-91-5

(E/Z)-2-buten-1-ol

A

acetaldol
107-89-1

acetaldol

B

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

C

methyl vinyl ketone
78-94-4

methyl vinyl ketone

D

1-Hydroxy-2-butanone
5077-67-8

1-Hydroxy-2-butanone

E

crotonaldehyde
123-73-9

crotonaldehyde

Conditions
ConditionsYield
With hydrogenchloride; lithium tetrachloropalladate(II); p-benzoquinone In water at 25℃; for 0.5h; Rate constant; Mechanism; Kinetics; equilibrium constants;A 39%
B 49%
C 0.9%
D 2.6%
E 8.5%
(E/Z)-2-buten-1-ol
6117-91-5

(E/Z)-2-buten-1-ol

A

acetaldol
107-89-1

acetaldol

B

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

C

1-Hydroxy-2-butanone
5077-67-8

1-Hydroxy-2-butanone

D

crotonaldehyde
123-73-9

crotonaldehyde

Conditions
ConditionsYield
hydrogenchloride; lithium tetrachloropalladate(II); p-benzoquinone In water at 25℃; for 0.5h; Further byproducts given;A 39%
B 49%
C 2.6%
D 8.5%
(1-methylcyclopropyl)amine
22936-83-0

(1-methylcyclopropyl)amine

A

ethene
74-85-1

ethene

B

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With lithium hypochlorite In water Ambient temperature;A 36%
B 3%
1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide
78-18-2

1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide

methyl vinyl ketone
78-94-4

methyl vinyl ketone

A

2,12-Tridecanedione
73154-83-3

2,12-Tridecanedione

B

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

C

2-oxodecanoic acid
333-60-8

2-oxodecanoic acid

D

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With titanium(III) chloride; acetic acid for 3h; Ambient temperature; Yields of byproduct given. Title compound not separated from byproducts;A 26%
B n/a
C n/a
D n/a
With titanium(III) chloride; acetic acid for 3h; Ambient temperature; Yield given. Title compound not separated from byproducts;A 26%
B n/a
C n/a
D n/a
oxirane
75-21-8

oxirane

acetaldehyde
75-07-0

acetaldehyde

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
at 120 - 180℃;
3-buten-1-yne
689-97-4

3-buten-1-yne

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With mercury(II) sulfate at 70 - 90℃;
With mercury(II) sulfate at 70 - 90℃;
methyl vinyl ketone
78-94-4

methyl vinyl ketone

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With sulfuric acid at 25℃;
With calcium hydroxide; formaldehyd at 25℃;
With sulfuric acid
With potassium carbonate
formaldehyd
50-00-0

formaldehyd

acetone
67-64-1

acetone

A

3-(hydroxymethyl)but-3-en-2-one
73255-29-5

3-(hydroxymethyl)but-3-en-2-one

B

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With potassium hydroxide
With potassium carbonate at 30 - 35℃;
methyl propargyl alcohol
764-01-2

methyl propargyl alcohol

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With mercury(II) diacetate; acetic acid
4-hydroxy-3-phenylsulfanyl-butan-2-one
13492-60-9

4-hydroxy-3-phenylsulfanyl-butan-2-one

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With hydrogen; nickel In 1,4-dioxane
2-methyl-1-buten-4-ol
763-32-6

2-methyl-1-buten-4-ol

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With ozone-containing oxygen; dimethylsulfide 1.) methanol, -78 deg C, 2.) -78 deg C -> room temperature; Yield given. Multistep reaction;
4,5-dihydro-1-(3-oxobutyl)-4-phenyl-1H-1,2,3,4-tetrazole-5-thione
58408-33-6

4,5-dihydro-1-(3-oxobutyl)-4-phenyl-1H-1,2,3,4-tetrazole-5-thione

A

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

B

1-Phenyl-1H-tetrazole-5-thiol anion
53079-79-1

1-Phenyl-1H-tetrazole-5-thiol anion

Conditions
ConditionsYield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant;
homoalylic alcohol
627-27-0

homoalylic alcohol

A

1.3-butanediol
18826-95-4, 107-88-0

1.3-butanediol

B

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With oxygen; cobalt(II) bis(salicylidene-γ-iminopropyl)methylamine
1.3-butanediol
18826-95-4, 107-88-0

1.3-butanediol

A

1,3-butanediol
24621-61-2

1,3-butanediol

B

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
at 30℃; for 43h; Kluyveromyces lactis IFO 1267, potassium phosphate buffer;A 38 mmol
B n/a
at 30℃; for 43h; Kluyveromyces lactis IFO 1267, potassium phosphate buffer;
1.3-butanediol
18826-95-4, 107-88-0

1.3-butanediol

A

acetaldol
107-89-1

acetaldol

B

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

C

acetaldehyde
75-07-0

acetaldehyde

D

methyl vinyl ketone
78-94-4

methyl vinyl ketone

E

butanone
78-93-3

butanone

F

iso-butanol
78-92-2, 15892-23-6

iso-butanol

Conditions
ConditionsYield
L-1930 Product distribution; various catalysts, temp.;
1.3-butanediol
18826-95-4, 107-88-0

1.3-butanediol

A

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

B

acetone
67-64-1

acetone

C

butanone
78-93-3

butanone

Conditions
ConditionsYield
MK-I at 120℃; under 760 Torr; Product distribution; Thermodynamic data; 150 - 220 deg C, different catalysts, E(excit.);A 29.46 % Chromat.
B 0.6 % Chromat.
C 3.3 % Chromat.
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

4-chloro-2-butanone
6322-49-2

4-chloro-2-butanone

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 14h; Inert atmosphere;100%
With hydrogenchloride; water at 0℃;
With thionyl chloride; benzene at 75℃;
With thionyl chloride In dichloromethane at 20℃;1.06 g
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

trityl chloride
76-83-5

trityl chloride

4-(trityloxy)butan-2-one
800380-59-0

4-(trityloxy)butan-2-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h;100%
With pyridine
With pyridine
triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

4-((triisopropylsilyl)oxy)butan-2-one
98264-29-0

4-((triisopropylsilyl)oxy)butan-2-one

Conditions
ConditionsYield
With 1H-imidazole at 20℃; for 19.5h; Inert atmosphere;100%
With 1H-imidazole
With 1H-imidazole In dichloromethane at 20℃;
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

4-(tert-butyldimethylsilyloxy)butan-2-one
120591-36-8

4-(tert-butyldimethylsilyloxy)butan-2-one

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃; for 18h;100%
With dmap; triethylamine In dichloromethane at 20℃; for 2h;98%
With 1H-imidazole In dichloromethane for 1.5h; Inert atmosphere;94%
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

4-nitrooxy-2-butanone

4-nitrooxy-2-butanone

Conditions
ConditionsYield
With N-nitro-2,4,6-trimethylpyridinium tetrafluoroborate In acetonitrile at 0℃; for 2h;100%
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

tert-Butyldiphenylsilyl β-hydroxybutanone
97250-25-4

tert-Butyldiphenylsilyl β-hydroxybutanone

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃; for 16h; Cooling with ice;100%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

4-(tetrahydropyran-2-yloxy)butan-2-one
20705-59-3

4-(tetrahydropyran-2-yloxy)butan-2-one

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 4h;99%
With toluene-4-sulfonic acid In dichloromethane at 0℃; for 1h;92%
Stage #1: 3,4-dihydro-2H-pyran; 1-Hydroxy-3-butanone With toluene-4-sulfonic acid In dichloromethane; water at 0℃; for 2h;
Stage #2: With sodium hydrogencarbonate for 0.5h;
83%
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

(+)-(1S,11R)-[1-Methoxy-2,2,3,3,7,7,8,8,11,12,12,13,13,17,17,18,18-heptadecamethyl-10,20-diaza-decahydroporphinato(2-)]nickel

(+)-(1S,11R)-[1-Methoxy-2,2,3,3,7,7,8,8,11,12,12,13,13,17,17,18,18-heptadecamethyl-10,20-diaza-decahydroporphinato(2-)]nickel

(+)-(1S,11R)-[1-(3'-Oxo-1'-butoxy)-2,2,3,3,7,7,8,8,11,12,12,13,13,17,17,18,18-heptadecamethyl-10,20-diaza-decahydroporphinato(2-)]-nickel

(+)-(1S,11R)-[1-(3'-Oxo-1'-butoxy)-2,2,3,3,7,7,8,8,11,12,12,13,13,17,17,18,18-heptadecamethyl-10,20-diaza-decahydroporphinato(2-)]-nickel

Conditions
ConditionsYield
(+)-(1R)-(1,2,2,3,3,7,7,8,8,12,12,13,13,17,17,18,18-Heptadecamethyl-10,20-diaza-octahydroporphinato)nickel-perchlorat In toluene byproducts: methanol; mixt. refluxed for 2 h while methanol removed by mol. sieve; solvent evapd., residue dissolved in hexane/acetonitrile, washed, filtered, solvent evapd., residue dried at 60°C, 0.01 Torr for 24 h;98.7%
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

(R)-butane-1,3-diol
6290-03-5

(R)-butane-1,3-diol

Conditions
ConditionsYield
With <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3; hydrogen In methanol at 50℃; under 38000 Torr; for 24h;98%
With hydrogen; dichloro(benzene)ruthenium(II) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In ethanol at 30℃; under 76000.1 Torr; for 40h; Yields of byproduct given. Title compound not separated from byproducts;96%
With methanol; phosphate buffer at 30℃; for 6.5h; Candida boidinii KK912 (IFO 10574);60%
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

1.3-butanediol
18826-95-4, 107-88-0

1.3-butanediol

Conditions
ConditionsYield
With hydrogen; sodium hydroxide In water at 25℃; under 7500.75 Torr; for 1h; Pressure; Reagent/catalyst; Solvent; Temperature; Autoclave;98%
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); isopropyl alcohol In water at 82℃; for 6h; Inert atmosphere; Schlenk technique; chemoselective reaction;91%
With potassium borohydride In tetrahydrofuran; water at 45℃; for 4h; Reagent/catalyst; Temperature; Cooling with ice;83%
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

Octanal
124-13-0

Octanal

1,3-butanediol monooctanoate

1,3-butanediol monooctanoate

Conditions
ConditionsYield
With bis(cyclopentadienyl)dihydrozirconium In tetrahydrofuran for 5h; Ambient temperature;98%
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

4-((p-toluenesulfonyl)oxy)-2-butanone
446876-96-6

4-((p-toluenesulfonyl)oxy)-2-butanone

Conditions
ConditionsYield
With pyridine In dichloromethane for 4h; Cooling with ice;98%
With pyridine In dichloromethane at 0 - 20℃;75%
With pyridine75%
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

1,3-butanediol
24621-61-2

1,3-butanediol

Conditions
ConditionsYield
With Ru2Cl4-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt3; hydrogen In methanol at 50℃; under 38000 Torr; for 24h;97%
at 30℃; for 48h; Candida parapsilosis IFO 1396;60%
With sodium perborate; (+)-β-chlorodiisopinocampheylborane 1.) THF, 0 deg C, 12 h; 2.) THF, EE, H2O, 0 deg C, 30 min; Yield given. Multistep reaction;
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

benzoyl chloride
98-88-4

benzoyl chloride

3-oxobutyl benzoate
29342-27-6

3-oxobutyl benzoate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 3h;96%
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

bromo-acetic acid-(3-oxo-butyl ester)
89641-46-3

bromo-acetic acid-(3-oxo-butyl ester)

Conditions
ConditionsYield
With pyridine at 0℃;96%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

4-((trimethylsilyl)oxy)-3-butanone
81852-67-7

4-((trimethylsilyl)oxy)-3-butanone

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;95%
With triethylamine In diethyl ether94%
With triethylamine In dichloromethane at 25℃; for 2h;80%
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

isobutyraldehyde
78-84-2

isobutyraldehyde

3-hydroxybutyl isobutyrate

3-hydroxybutyl isobutyrate

Conditions
ConditionsYield
With bis(cyclopentadienyl)dihydrozirconium In tetrahydrofuran for 5h; Ambient temperature;95%
With scandium tris(trifluoromethanesulfonate) In tetrahydrofuran at 20℃; for 2.5h; Reduction; Tishchenko;
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

aniline
62-53-3

aniline

4-phenylamino-butan-2-one
6220-79-7

4-phenylamino-butan-2-one

Conditions
ConditionsYield
With iodine In dimethyl sulfoxide at 20℃; for 8h; Solvent; Reagent/catalyst; Inert atmosphere;94%
With iodine In dimethyl sulfoxide at 20℃; for 8h; Reagent/catalyst; Solvent; Time;94%
With tert.-butylnitrite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In dimethyl sulfoxide at 20℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Time; Inert atmosphere;88%
1H-imidazole
288-32-4

1H-imidazole

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

sodium sulfate
7757-82-6

sodium sulfate

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

4-tert.Butyldiphenylsiloxybutan-2-one

4-tert.Butyldiphenylsiloxybutan-2-one

Conditions
ConditionsYield
In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane94%
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

benzyl bromide
100-39-0

benzyl bromide

4-(benzyloxy)-2-butanone
6278-91-7

4-(benzyloxy)-2-butanone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine at 150℃; for 1h; Inert atmosphere; Neat (no solvent);94%
With N-ethyl-N,N-diisopropylamine at 150℃; for 2h;22.2%
With N-ethyl-N,N-diisopropylamine at 150℃; for 2h; Inert atmosphere;
With N-ethyl-N,N-diisopropylamine at 150℃; for 2h; Inert atmosphere;
With N-ethyl-N,N-diisopropylamine at 150℃; for 2h; Inert atmosphere;
2-Methoxypropene
116-11-0

2-Methoxypropene

1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

4-(1-Methoxy-1-methyl-ethoxy)-butan-2-one
82495-49-6

4-(1-Methoxy-1-methyl-ethoxy)-butan-2-one

Conditions
ConditionsYield
With trichlorophosphate93%
With toluene-4-sulfonic acid In tetrahydrofuran
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

2-[(4-methoxybenzyl)oxy]-3-nitropyridine
350848-02-1

2-[(4-methoxybenzyl)oxy]-3-nitropyridine

4-((4-methoxybenzyl)oxy)butan-2-one
85846-38-4

4-((4-methoxybenzyl)oxy)butan-2-one

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.0833333h;93%
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

4-(methoxymethoxy)butan-2-one
26822-73-1

4-(methoxymethoxy)butan-2-one

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 17h; Reflux; Inert atmosphere;93%
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

m,p-dichloroaniline
95-76-1

m,p-dichloroaniline

4-((3,4-dichlorophenyl)amino)-2-butanone

4-((3,4-dichlorophenyl)amino)-2-butanone

Conditions
ConditionsYield
With iodine In dimethyl sulfoxide at 20℃; for 8h; Inert atmosphere;93%
With iodine In dimethyl sulfoxide at 20℃; for 8h;93%
With tert.-butylnitrite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In dimethyl sulfoxide at 20℃; for 9h; Inert atmosphere; Green chemistry;86%
With tert.-butylnitrite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In dimethyl sulfoxide at 20℃; for 9h; Inert atmosphere;86%
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

ethyl vinyl ether
109-92-2

ethyl vinyl ether

4-(1-ethoxyethoxy)butan-2-one
25368-66-5

4-(1-ethoxyethoxy)butan-2-one

Conditions
ConditionsYield
With pyridine; p-toluenesulfonic acid monohydrate In dichloromethane at 20℃;92%
With cobalt(II) chloride In acetonitrile Ambient temperature;81%
With hydrogenchloride
1-Hydroxy-3-butanone
590-90-9

1-Hydroxy-3-butanone

chlorodimethyl(1,1,2-trimethylpropyl)silane
67373-56-2

chlorodimethyl(1,1,2-trimethylpropyl)silane

4-dimethylthexylsilyloxy-2-butanone
140139-14-6

4-dimethylthexylsilyloxy-2-butanone

Conditions
ConditionsYield
With dmap In dichloromethane92%

590-90-9Relevant academic research and scientific papers

Chemoselective Oxidation of Secondary Hydroxy Groups by the Molybdenum Hexacarbonyl/Cetylpyridinium Chloride/t-Butyl Hydroperoxide System

Yamawaki, Kazumasa,Yoshida, Tsutomu,Suda, Takashi,Ishii, Yasutaka,Ogawa, Masaya

, p. 59 - 60 (1986)

The system molybdenum hexacarbonyl/cetylpyridinium chloride/t-butyl hydroperoxide in benzene is used for the chemoselective oxidation of secondary hydroxy compounds to the corresponding carbonyl derivatives.

Enzymatic syntheses of 13C-enriched geranylgeranyl diphosphate and casbene from 13C-labeled isopentenyl diphosphate

Huang, Qiulong,Huang, Kexue,Scott

, p. 2033 - 2036 (1998)

Geranylgeranyl diphosphate and casbene were synthesized in high yields from [4-13c]-3-methyl-3- butenyl diphosphate, using coupled enzyme reactions.

HIGHLY SELECTIVE OXIDATION OF SECONDARY HYDROXYL FUNCTIONS USING THE VO(acac)2-t-BuOOH SYSTEM

Kaneda, Kiyotomi,Kawanishi, Yasuyuki,Jitsukawa, Koichiro,Teranishi, Shiichiro

, p. 5009 - 5010 (1983)

The VO(acac)2-t-BuOOH system shows high oxidation reactivity for secondary alkohols to give ketones.

Process for preparing 4-hydroxy-2-butanone

-

Paragraph 0024-0044, (2020/12/31)

The invention provides a process for preparing 4-hydroxy-2-butanone. Amino acid is used as a catalyst to catalyze the condensation reaction of formaldehyde and acetone at normal temperature, so as tosynthesize 4-hydroxy-2-butanone in one step. The yield of the prepared 4-hydroxy-2-butanone is high, the purity reaches 98%, the production cost is reduced, the corrosion effect caused by the use of astrong base catalyst is avoided, the catalyst and the solvent can be recycled for 10 times or more, and the whole synthesis process is economical and environment-friendly.

Hydroxycarbonyl compound (by machine translation)

-

Paragraph 0070, (2020/01/31)

After the separated and purified efficiently and easily by hydroxycarbonyl compound [a] of production method. [Solution] a carbonyl compound having a hydrogen atom at α-position with paraformaldehyde, acidic or basic catalyst is added to the environment is not reacting with the method. Figure 1 [drawing] (by machine translation)

Preparation method of hydroxyl ketone compound

-

Paragraph 0024-0036; 0039-0048; 0055-0059, (2020/07/12)

The invention discloses a preparation method of a hydroxyl ketone compound. The method comprises a step of converting dihydric alcohol into a hydroxyl ketone compound in the presence of a copper-basedcatalyst, namely a conversion step, and the reaction conditions of the conversion step are as follows: the reaction temperature is 200-400 DEG C, the reaction pressure is 0.01-0.5 MPa, and the liquidhour space velocity is 0.1-10 h. The method has a high raw material conversion rate and high selectivity of the hydroxyl ketone compound with terminal hydroxyl, and is easy to implement industrially.

Reductive Electrochemical Activation of Molecular Oxygen Catalyzed by an Iron-Tungstate Oxide Capsule: Reactivity Studies Consistent with Compound i Type Oxidants

Bugnola, Marco,Shen, Kaiji,Haviv, Eynat,Neumann, Ronny

, p. 4227 - 4237 (2020/05/05)

The reductive activation of molecular oxygen catalyzed by iron-based enzymes toward its use as an oxygen donor is paradigmatic for oxygen transfer reactions in nature. Mechanistic studies on these enzymes and related biomimetic coordination compounds designed to form reactive intermediates, almost invariably using various "shunt" pathways, have shown that high-valent Fe(V)=O and the formally isoelectronic Fe(IV) =O porphyrin cation radical intermediates are often thought to be the active species in alkane and arene hydroxylation and alkene epoxidation reactions. Although this four decade long research effort has yielded a massive amount of spectroscopic data, reactivity studies, and a detailed, but still incomplete, mechanistic understanding, the actual reductive activation of molecular oxygen coupled with efficient catalytic transformations has rarely been experimentally studied. Recently, we found that a completely inorganic iron-tungsten oxide capsule with a keplerate structure, noted as {Fe30W72}, is an effective electrocatalyst for the cathodic activation of molecular oxygen in water leading to the oxidation of light alkanes and alkenes. The present report deals with extensive reactivity studies of these {Fe30W72} electrocatalytic reactions showing (1) arene hydroxylation including kinetic isotope effects and migration of the ipso substituent to the adjacent carbon atom ("NIH shift"); (2) a high kinetic isotope effect for alkyl C - H bond activation; (3) dealkylation of alkylamines and alkylsulfides; (4) desaturation reactions; (5) retention of stereochemistry in cis-alkene epoxidation; and (6) unusual regioselectivity in the oxidation of cyclic and acyclic ketones, alcohols, and carboxylic acids where reactivity is not correlated to the bond disassociation energy; the regioselectivity obtained is attributable to polar effects and/or entropic contributions. Collectively these results also support the conclusion that the active intermediate species formed in the catalytic cycle is consistent with a compound I type oxidant. The activity of {Fe30W72} in cathodic aerobic oxidation reactions shows it to be an inorganic functional analogue of iron-based monooxygenases.

High purity 1,3-butanediol and its preparation method

-

Paragraph 0172; 0181; 0182, (2019/05/25)

The present invention relates to a high purity 1,3-butanediol and a preparation method thereof. The preparation method of the present invention comprises: a step (a) of mixing distilled water, a buffer solution and paraformaldehyde to obtain a mixture, and heating the mixture to prepare formaldehyde; a step (b) of mixing formaldehyde of the step (a) (s100) with acetone, and making the formaldehyde of the step (a) react with the acetone to prepare a mixed solution as an intermediate; a step (c) of reducing the intermediate of the step (b) (s200) to prepare 1,3-butanediol; and a step (d) of deodorizing/purifying 1,3-butanediol of the step (c) (s300). According to the present invention, the high purity 1,3-butanediol prepared by the preparation method not only can be used as raw material for various resins such as polyester resins, alkyd resins, urethane resins, urethane coatings and the like as industrial uses, but also can be diversely used in other fabric softeners, pharmaceuticals, dyestuffs and others. Further, the high purity 1,3-butanediol not only can be used as a moisturizer for a cosmetic composition, perfume and hair since slight intoxication is not generated although the high purity 1,3-butanediol is stored for a long period, but also can be used in a preparation for spice of food products or the like.(AA) Start(BB) End(S10) Step of preparing high purity formaldehyde(S200) Step of preparing an intermediate(S300) Step of reducing the intermediate(S400) Step of performing deodorizing and purifying operationsCOPYRIGHT KIPO 2019

Production method of 4-hydroxy-2-butanone

-

Paragraph 0018-0027, (2019/10/01)

Belonging to the field of fine chemicals, the invention discloses a production method of 4-hydroxy-2-butanone, and solves the problem of low yield of existing synthetic methods. The method provided bythe invention includes the steps of: adding 1, 3-butanediol, a catalyst, an assistant, water and a water-carrying agent into a reaction kettle, and performing heating to 55-60DEGC; adding hydrogen peroxide dropwise into the mixed solution, and conducting reduced pressure distillation of water; stopping adding hydrogen peroxide, and further performing stirring for 1-1.5h to distill the water-carrying agent out; controlling the temperature of the system not higher than 60DEGC, and conducting reduced pressure rectification to obtain the final product 4-hydroxy-2-butanone. By adding the assistant, 1, 3-butanediol can better participate in the reaction, and the conversion rate can be improved. The chemical reaction carried out in the invention is carried out under a negative pressure condition, and the temperature is controlled not higher than 60DEG C, thus avoiding the generation of methyl vinyl ketone; and in a negative pressure system, the reaction can be fully carried out under a low temperature condition, the product is easier to distill, and impurities are not easily produced.

Aerobic Oxidation of Secondary Alcohols with Nitric Acid and Iron(III) Chloride as Catalysts in Fluorinated Alcohol

Mo?ina, ?tefan,Iskra, Jernej

, p. 14579 - 14586 (2019/11/14)

Fluorinated alcohols as solvents strongly influence and direct chemical reaction through donation of strong hydrogen bonds while being weak acceptors. We used 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as the activating solvent for a nitric acid and FeCl3-catalyzed aerobic oxidation of secondary alcohols to ketones. Reaction proceeded selectively with excellent yields with no reaction on the primary alcohol group. Oxidation of benzyl alcohols proceeds selectively to aldehydes with only HNO3 as the catalyst, while reaction on tertiary alcohols proceeds through dehydration and dimerization. A mechanistic study showed in situ formation of NOCl that converts alcohol into alkyl nitrite, which in the presence of Fe3+ ions and fluorinated alcohol decomposes into ketone. The study indicates that iron(III) acts also as the single-electron transfer catalyst in regeneration of NOCl reactive species.

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