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4-Hydroxy-2-butanone

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Name

4-Hydroxy-2-butanone

EINECS 209-693-6
CAS No. 590-90-9 Density 0.987 g/cm3
PSA 37.30000 LogP -0.04220
Solubility miscible with water, ethanol and ether Melting Point 15°C (estimate)
Formula C4H8O2 Boiling Point 156.3 °C at 760 mmHg
Molecular Weight 88.1063 Flash Point 55.5 °C
Transport Information UN 1993 Appearance Colorless liquid
Safety 16 Risk Codes 10
Molecular Structure Molecular Structure of 590-90-9 (4-Hydroxy-2-butanone) Hazard Symbols R10:;
Synonyms

1-Hydroxybutan-3-one;2-Hydroxyethyl methyl ketone;3-Ketobutan-1-ol;3-Ketobutanol;3-Oxo-1-butanol;3-Oxobutanol;4-Butanol-2-one;4-Hydroxy-2-butanone;Methylolacetone;Monomethylolacetone;NSC 41219;

Article Data 131

4-Hydroxy-2-butanone Synthetic route

927-74-2

1-butyn-4-ol

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.
5754-32-5

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

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%
625-34-3

3-oxobutyraldehyde

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%
50-00-0

formaldehyd

67-64-1

acetone

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%
72064-43-8

tert-butyldimethylsilyl 4-phenylbutyl ether

590-90-9

1-Hydroxy-3-butanone

Conditions
ConditionsYield
With sodium periodate In tetrahydrofuran; water at 25℃;92%
120591-36-8

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

590-90-9

1-Hydroxy-3-butanone

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

1.3-butanediol

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%
110-88-3

1,3,5-Trioxan

67-64-1

acetone

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%
598-32-3

2-hydroxy-3-butene

A

107-89-1

acetaldol

B

590-90-9

1-Hydroxy-3-butanone

C

513-86-0, 52217-02-4

3-hydroxy-2-butanon

D

78-94-4

methyl vinyl ketone

E

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%
598-32-3

2-hydroxy-3-butene

A

107-89-1

acetaldol

B

590-90-9

1-Hydroxy-3-butanone

C

513-86-0, 52217-02-4

3-hydroxy-2-butanon

D

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-Hydroxy-2-butanone Specification

The IUPAC name of 2-Butanone, 4-hydroxy- is 4-hydroxybutan-2-one. With the CAS registry number 590-90-9 and EINECS 209-693-6, it is also named as 3-Ketobutan-1-ol. The product's categories are Straight Chain Compounds; Ketone. It is colorless liquid which is miscible with water, ethanol and ether and flammable. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.79; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.78; (4)ACD/LogD (pH 7.4): -0.78; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 8.92; (8)ACD/KOC (pH 7.4): 8.92; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.411; (14)Molar Refractivity: 22.14 cm3; (15)Molar Volume: 89.1 cm3; (16)Polarizability: 8.77×10-24 cm3; (17)Surface Tension: 32.5 dyne/cm; (18)Density: 0.987 g/cm3; (19)Flash Point: 55.5 °C; (20)Enthalpy of Vaporization: 45.77 kJ/mol; (21)Boiling Point: 156.3 °C at 760 mmHg; (22)Vapour Pressure: 1.05 mmHg at 25°C.

Preparation of 2-Butanone, 4-hydroxy-: It can be obtained by (+-)-butane-1,3-diol. This reaction needs reagents N-hydroxyphthalimide, O2, Co(acac)2 and solvent acetonitrile by heating. The reaction time is 12 hours. The yield is 61 % Chromat.

2-Butanone, 4-hydroxy- can be obtained by (+-)-butane-1,3-diol

Uses of 2-Butanone, 4-hydroxy-: It is used as pharmaceutical intermediate and in organic synthesis. For example, it can react with 3,4-dihydro-2H-pyran to get 4-tetrahydropyran-2-yloxy-butan-2-one. This reaction needs reagent p-toluenesulfonic acid and solvent CH2Cl2 at temperature of 0 °C. The reaction time is 1 hours. The yield is 92%.

2-Butanone, 4-hydroxy- can react with 3,4-dihydro-2H-pyran to get 4-tetrahydropyran-2-yloxy-butan-2-one

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C(C)CCO
2. InChI:InChI=1/C4H8O2/c1-4(6)2-3-5/h5H,2-3H2,1H3
3. InChIKey:LVSQXDHWDCMMRJ-UHFFFAOYAN

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