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3-Acetyl-1-propanol, also known as 3-Acetopropanol, is a clear colorless liquid that serves as a crucial intermediate in the synthesis of various compounds and acts as a substrate for specific enzymes. Its chemical structure and properties make it a versatile molecule with applications across different industries.

1071-73-4

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1071-73-4 Usage

Uses

Used in Pharmaceutical Industry:
3-Acetyl-1-propanol is used as an intermediate in the synthesis of Didesethyl Chloroquine (D440960), a metabolite of Chloroquine. This application is significant in the development of anti-malarial drugs, as it contributes to the production of effective treatments for the disease.
Used in Enzyme Research:
3-Acetyl-1-propanol is used as a substrate for alcohol dehydrogenase, an enzyme that plays a vital role in the metabolism of alcohols. This application is essential in the study of enzyme kinetics, understanding the mechanisms of alcohol metabolism, and potentially developing new therapeutic strategies for alcohol-related health issues.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 4456, 1953 DOI: 10.1021/ja01114a018Tetrahedron Letters, 26, p. 5713, 1985 DOI: 10.1016/S0040-4039(01)80928-X

Safety Profile

Moderately toxic by ingestion andinhalation. When heated to decomposition it emits acridsmoke.

Check Digit Verification of cas no

The CAS Registry Mumber 1071-73-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,7 and 1 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1071-73:
(6*1)+(5*0)+(4*7)+(3*1)+(2*7)+(1*3)=54
54 % 10 = 4
So 1071-73-4 is a valid CAS Registry Number.
InChI:InChI=1/C5H10O2/c1-5(7)3-2-4-6/h6H,2-4H2,1H3

1071-73-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Acetyl-1-propanol

1.2 Other means of identification

Product number -
Other names 2-Pentanone, 5-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:1071-73-4 SDS

1071-73-4Synthetic route

pent-1-yn-5-ol
5390-04-5

pent-1-yn-5-ol

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With C20H44Cl4N8O4P4Pd2S2; water at 30℃; for 9h; Reagent/catalyst;100%
With cisplatin In water at 37℃; for 120h;67%
With water; mercury(II) sulfate
4-oxopentyl acetate
5185-97-7

4-oxopentyl acetate

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With sodium methylate In methanol for 4.5h; Ambient temperature;96%
4-oxopentyl formate
63305-45-3

4-oxopentyl formate

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With sodium methylate In methanol for 1.5h;95%
1,4-Pentanediol
626-95-9

1,4-Pentanediol

A

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

B

4-oxopentyl acetate
5185-97-7

4-oxopentyl acetate

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII); sodium bromide In acetic acid for 10h; Ambient temperature;A 94%
B 6%
1,4-Pentanediol
626-95-9

1,4-Pentanediol

acetic acid
64-19-7

acetic acid

A

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

B

4-oxopentyl acetate
5185-97-7

4-oxopentyl acetate

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII); sodium bromide for 10h; Ambient temperature;A 94%
B 6%
3-(2-methyl-[1,3]oxathian-2-yl)-propan-1-ol

3-(2-methyl-[1,3]oxathian-2-yl)-propan-1-ol

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene; sodium iodide In dichloromethane at 20℃; for 0.25h; Ring cleavage; De(monothio)acetalization;90%
5-(3-benzyloxypropyl)-1,2,3-oxadiazole 3-oxide

5-(3-benzyloxypropyl)-1,2,3-oxadiazole 3-oxide

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 2h;78%
3-acetyl-2-oxo-4,5-dihydrofuran
517-23-7

3-acetyl-2-oxo-4,5-dihydrofuran

A

4-butanolide
96-48-0

4-butanolide

B

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

C

ethyl 4-hydroxybutanoate
999-10-0

ethyl 4-hydroxybutanoate

D

ethyl 4-(acetyloxy)butanoate
25560-91-2

ethyl 4-(acetyloxy)butanoate

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 200℃; for 2h;A 75%
B 5%
C 8%
D 12%
With sodium hydroxide In ethanol; water at 200℃; for 2h;A 75%
B 3%
C 8%
D 12%
With sodium hydroxide In ethanol; water at 200℃; for 2h; Product distribution; other reagent/educt ratio,;A 15%
B 16%
C 4%
D 62%
With sodium hydroxide In ethanol; water at 200℃; for 2h;A 15%
B 16%
C 4%
D 62%
furfural
98-01-1

furfural

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With hydrogen In water at 80℃; under 1500.15 Torr; for 20.4167h; Pressure; Temperature; Reagent/catalyst; Autoclave;72%
With carbon dioxide; water; hydrogen at 60℃; under 30003 Torr; for 36h; Temperature; Autoclave;
With hydrogen In water at 80℃; under 7500.75 Torr; for 10h; Temperature; Reagent/catalyst; Pressure; Autoclave; Molecular sieve;
With hydrogen In water at 80℃; under 1500.15 Torr; for 20h;
1,4-Pentanediol
626-95-9

1,4-Pentanediol

A

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

B

3-methyltetrahydro-2-furanone
1679-47-6

3-methyltetrahydro-2-furanone

Conditions
ConditionsYield
With aluminum oxide; potassium permanganate; copper(II) sulfate at 20℃; for 36h;A 30%
B 70%
3-diphenylphosphinoyl-5-hydroxypentan-2-one
89625-16-1

3-diphenylphosphinoyl-5-hydroxypentan-2-one

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 60℃; for 2h;65%
With sodium hydroxide In ethanol at 60℃; for 3h;53%
Cyclopropyl methyl ketone
765-43-5

Cyclopropyl methyl ketone

A

2-Methyl-tetrahydro-furan-2-ol
7326-46-7

2-Methyl-tetrahydro-furan-2-ol

B

5-(2-methyl-tetrahydrofuran-2-yloxy)pentan-2-one
7326-47-8

5-(2-methyl-tetrahydrofuran-2-yloxy)pentan-2-one

C

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

D

6-oxaundeca-2,10-dione
93677-66-8

6-oxaundeca-2,10-dione

Conditions
ConditionsYield
With copper(ll) bromide In diethyl ether; water at 180℃; for 6h;A n/a
B n/a
C n/a
D 64%
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

1,4-Pentanediol
626-95-9

1,4-Pentanediol

C

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With hydrogen; toluene-4-sulfonic acid In water at 140℃; under 11251.1 Torr; for 4h; Autoclave;A 19%
B 63%
C 8%
With carbon dioxide; hydrogen In water at 80℃; under 30003 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Temperature; Autoclave;A 8%
B 57%
C 15%
(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With carbon dioxide; hydrogen at 60℃; under 30003 Torr; for 0.25h; Autoclave;62%
1,4-Pentanediol
626-95-9

1,4-Pentanediol

A

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

B

5-methyl-dihydro-furan-2-one
108-29-2

5-methyl-dihydro-furan-2-one

Conditions
ConditionsYield
With tris(cetylpyridinium) 12-tungstophosphate; dihydrogen peroxide In tert-butyl alcohol for 24h; Heating;A 60%
B 30%
With copper chromite; silica gel; stearic acid
With sodium hydroxide; copper chromite; stearic acid
1,4-Pentanediol
626-95-9

1,4-Pentanediol

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone60%
With Celite; silver carbonate In benzene for 1h; Heating;
With water; fluorine; acetonitrile In chloroform at -10 - 0℃;
With Rhodococcus ruber DSM 44541 In acetone at 30℃; for 48h; pH=7.5;
With palladium on activated charcoal at 120 - 300℃; Reagent/catalyst;
furfural
98-01-1

furfural

A

1,4-Pentanediol
626-95-9

1,4-Pentanediol

B

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With hydrogen In water at 80℃; under 1500.15 Torr; for 20.4167h; Pressure; Temperature; Reagent/catalyst; Autoclave;A 17%
B 56%
With hydrogen In water at 80℃; under 1500.15 Torr; for 20h;
3-acetyl-2-oxo-4,5-dihydrofuran
517-23-7

3-acetyl-2-oxo-4,5-dihydrofuran

A

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

B

3-hydroxy-4-(2-hydroxyethyl)-5-methylisoxazole
92745-95-4

3-hydroxy-4-(2-hydroxyethyl)-5-methylisoxazole

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine hydrochloride at 0 - 5℃; for 1h;A 24 % Chromat.
B 48%
1,4-Pentanediol
626-95-9

1,4-Pentanediol

A

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

B

4-oxopentanal
626-96-0

4-oxopentanal

C

5-methyl-dihydro-furan-2-one
108-29-2

5-methyl-dihydro-furan-2-one

Conditions
ConditionsYield
With oxygen In 2,4-dichlorophenoxyacetic acid dimethylamine; toluene at 80℃; for 4h;A n/a
B n/a
C 44%
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

C

1,4-Pentanediol
626-95-9

1,4-Pentanediol

D

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With hydrogen In water at 140℃; under 11251.1 Torr; for 4h; Autoclave;A 26%
B 8%
C 36%
D 18%
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

C

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With carbon dioxide; hydrogen In water at 80℃; under 30003 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Autoclave;A 11%
B 26%
C 10%
pent-1-yn-5-ol
5390-04-5

pent-1-yn-5-ol

A

5-(2-methyl-tetrahydrofuran-2-yloxy)pentan-2-one
7326-47-8

5-(2-methyl-tetrahydrofuran-2-yloxy)pentan-2-one

B

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With cisplatin In water at 37℃; for 48h;A 22%
B n/a
n-Pent-4-enyl alcohol
821-09-0

n-Pent-4-enyl alcohol

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With pyridine; oxygen; isopropyl alcohol; palladium diacetate In toluene at 60℃; for 6h; Oxidation;21%
With Rh(III)(tetra(p-sulfonatophenyl)porphyrinato)(OD2)2(3-); water at 60℃; pH=9; borate buffer;
5-hexenoic acid
1577-22-6

5-hexenoic acid

2-Chloroethyl chloroformate
627-11-2

2-Chloroethyl chloroformate

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
Stage #1: 5-hexenoic acid; 2-Chloroethyl chloroformate With triethylamine In tetrahydrofuran at -20℃; for 0.75h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 3h;
5%
oxirane
75-21-8

oxirane

sodium ethyl acetylacetate enolate
1007476-32-5

sodium ethyl acetylacetate enolate

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
Erwaermen des entstandenen α-Acetyl-butyrolactons mit 5prozentiger HCl;
2-methyltetrahydrofuran
96-47-9

2-methyltetrahydrofuran

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With hydrogenchloride; water; hydrogen; palladium dichloride at 55 - 60℃; under 1520 - 1900 Torr; Product distribution; effect of catalyst poisons;
With diethyl ether; oxygen; dinitrogen tetraoxide at 30 - 40℃;
With calcium hypochlorite; acetic acid at 20℃; for 1h; regioselective reaction;
With diethyl ether; oxygen; manganese(II) acetate at 70℃;
Tetrahydrofurfuryl chloride
3003-84-7

Tetrahydrofurfuryl chloride

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With potassium tert-butylate; tert-butyl alcohol anschliessendes Behandeln mit wss.Schwefelsaeure;
tetrahydrofurfuryl bromide
1192-30-9

tetrahydrofurfuryl bromide

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With potassium hydroxide; triethanolamine anschliessendes Behandeln mit wss.Schwefelsaeure;
2-Methyl-4,5-dihydrofuran
1487-15-6

2-Methyl-4,5-dihydrofuran

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With water
With hydrogenchloride
2-methylfuran
534-22-5

2-methylfuran

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With hydrogenchloride; palladium on activated charcoal; acetone Hydrogenation;
With formic acid; nickel kieselguhr; hydrogen at 150℃; under 77228.3 Torr; Hydrogenation.Reagens 4: Wasser; Reagens 5: Dioxan;
With hydrogen In acetone
With 5%-palladium/activated carbon; water; hydrogen at 28℃; for 3h; Reagent/catalyst; Temperature;448 g
5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

1,4-Pentanediol
626-95-9

1,4-Pentanediol

Conditions
ConditionsYield
With zirconium dioxide hydrate; isopropyl alcohol at 130℃; for 0.666667h; Meerwein-Ponndorf-Verley Reduction;100%
With K12(Ga4(1,5-bis(2,3-dihydroxybenzamido)naphthalene))6; potassium phosphate; borane pyridine In water-d2 at 20℃; Inert atmosphere;68%
With sodium hydroxide; sodium tetrahydroborate In methanol
5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

5-((tert-butyldimethylsilyl)oxy)pentan-2-one
86864-59-7

5-((tert-butyldimethylsilyl)oxy)pentan-2-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide Inert atmosphere;99%
With 1H-imidazole In N,N-dimethyl-formamide for 12h; Ambient temperature;89%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 4.5h; Inert atmosphere;88%
5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

(±)-4-amino-1-pentanol
927-55-9

(±)-4-amino-1-pentanol

Conditions
ConditionsYield
With ammonium hydroxide; hydrogen In ethanol; water at 80℃; under 15001.5 Torr; for 2h; Autoclave;99%
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; sodium hydrogencarbonate
2: nickel; hydrogen
View Scheme
triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

C14H30O2Si

C14H30O2Si

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃;97%
With 1H-imidazole In dichloromethane at 20℃;77%
triethylsilane
617-86-7

triethylsilane

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

5-(triethylsiloxy)pentan-2-one

5-(triethylsiloxy)pentan-2-one

Conditions
ConditionsYield
With 2,3-Dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene In neat (no solvent) at 50℃; for 5h; Glovebox; Inert atmosphere; Schlenk technique; chemoselective reaction;96%
With copper (I) tert-butoxide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 24℃; for 5h;84%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

2-methyl 2-(3'-hydroxypropyl-1')-1,3-dithiane
211873-52-8

2-methyl 2-(3'-hydroxypropyl-1')-1,3-dithiane

Conditions
ConditionsYield
With copper bis(dodecyl sulfate) In water at 20℃; for 6h; Inert atmosphere;96%
With vanadyl trifluoromethanesulfonate In dichloromethane; acetonitrile at 20℃; for 17h; Inert atmosphere; chemoselective reaction;87%
triethylsilyl chloride
994-30-9

triethylsilyl chloride

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

5-(triethylsiloxy)pentan-2-one

5-(triethylsiloxy)pentan-2-one

Conditions
ConditionsYield
With pyridine at 20℃; for 12h;96%
1-methylindole
603-76-9

1-methylindole

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

3-(tetrahydro-2-methylfuran-2-yl)-1-methyl-1H-indole
959977-38-9

3-(tetrahydro-2-methylfuran-2-yl)-1-methyl-1H-indole

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 40℃;96%
pent-1-yn-5-ol
5390-04-5

pent-1-yn-5-ol

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With C20H44Cl4N8O4P4Pd2S2; water at 30℃; for 9h; Reagent/catalyst;100%
With cisplatin In water at 37℃; for 120h;67%
With water; mercury(II) sulfate
4-oxopentyl acetate
5185-97-7

4-oxopentyl acetate

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With sodium methylate In methanol for 4.5h; Ambient temperature;96%
4-oxopentyl formate
63305-45-3

4-oxopentyl formate

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With sodium methylate In methanol for 1.5h;95%
1,4-Pentanediol
626-95-9

1,4-Pentanediol

A

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

B

4-oxopentyl acetate
5185-97-7

4-oxopentyl acetate

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII); sodium bromide In acetic acid for 10h; Ambient temperature;A 94%
B 6%
1,4-Pentanediol
626-95-9

1,4-Pentanediol

acetic acid
64-19-7

acetic acid

A

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

B

4-oxopentyl acetate
5185-97-7

4-oxopentyl acetate

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII); sodium bromide for 10h; Ambient temperature;A 94%
B 6%
3-(2-methyl-[1,3]oxathian-2-yl)-propan-1-ol

3-(2-methyl-[1,3]oxathian-2-yl)-propan-1-ol

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene; sodium iodide In dichloromethane at 20℃; for 0.25h; Ring cleavage; De(monothio)acetalization;90%
5-(3-benzyloxypropyl)-1,2,3-oxadiazole 3-oxide

5-(3-benzyloxypropyl)-1,2,3-oxadiazole 3-oxide

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 2h;78%
3-acetyl-2-oxo-4,5-dihydrofuran
517-23-7

3-acetyl-2-oxo-4,5-dihydrofuran

A

4-butanolide
96-48-0

4-butanolide

B

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

C

ethyl 4-hydroxybutanoate
999-10-0

ethyl 4-hydroxybutanoate

D

ethyl 4-(acetyloxy)butanoate
25560-91-2

ethyl 4-(acetyloxy)butanoate

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 200℃; for 2h;A 75%
B 5%
C 8%
D 12%
With sodium hydroxide In ethanol; water at 200℃; for 2h;A 75%
B 3%
C 8%
D 12%
With sodium hydroxide In ethanol; water at 200℃; for 2h; Product distribution; other reagent/educt ratio,;A 15%
B 16%
C 4%
D 62%
With sodium hydroxide In ethanol; water at 200℃; for 2h;A 15%
B 16%
C 4%
D 62%
furfural
98-01-1

furfural

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With hydrogen In water at 80℃; under 1500.15 Torr; for 20.4167h; Pressure; Temperature; Reagent/catalyst; Autoclave;72%
With carbon dioxide; water; hydrogen at 60℃; under 30003 Torr; for 36h; Temperature; Autoclave;
With hydrogen In water at 80℃; under 7500.75 Torr; for 10h; Temperature; Reagent/catalyst; Pressure; Autoclave; Molecular sieve;
With hydrogen In water at 80℃; under 1500.15 Torr; for 20h;
1,4-Pentanediol
626-95-9

1,4-Pentanediol

A

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

B

3-methyltetrahydro-2-furanone
1679-47-6

3-methyltetrahydro-2-furanone

Conditions
ConditionsYield
With aluminum oxide; potassium permanganate; copper(II) sulfate at 20℃; for 36h;A 30%
B 70%
3-diphenylphosphinoyl-5-hydroxypentan-2-one
89625-16-1

3-diphenylphosphinoyl-5-hydroxypentan-2-one

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 60℃; for 2h;65%
With sodium hydroxide In ethanol at 60℃; for 3h;53%
Cyclopropyl methyl ketone
765-43-5

Cyclopropyl methyl ketone

A

2-Methyl-tetrahydro-furan-2-ol
7326-46-7

2-Methyl-tetrahydro-furan-2-ol

B

5-(2-methyl-tetrahydrofuran-2-yloxy)pentan-2-one
7326-47-8

5-(2-methyl-tetrahydrofuran-2-yloxy)pentan-2-one

C

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

D

6-oxaundeca-2,10-dione
93677-66-8

6-oxaundeca-2,10-dione

Conditions
ConditionsYield
With copper(ll) bromide In diethyl ether; water at 180℃; for 6h;A n/a
B n/a
C n/a
D 64%
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

1,4-Pentanediol
626-95-9

1,4-Pentanediol

C

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With hydrogen; toluene-4-sulfonic acid In water at 140℃; under 11251.1 Torr; for 4h; Autoclave;A 19%
B 63%
C 8%
With carbon dioxide; hydrogen In water at 80℃; under 30003 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Temperature; Autoclave;A 8%
B 57%
C 15%
(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With carbon dioxide; hydrogen at 60℃; under 30003 Torr; for 0.25h; Autoclave;62%
1,4-Pentanediol
626-95-9

1,4-Pentanediol

A

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

B

5-methyl-dihydro-furan-2-one
108-29-2

5-methyl-dihydro-furan-2-one

Conditions
ConditionsYield
With tris(cetylpyridinium) 12-tungstophosphate; dihydrogen peroxide In tert-butyl alcohol for 24h; Heating;A 60%
B 30%
With copper chromite; silica gel; stearic acid
With sodium hydroxide; copper chromite; stearic acid
1,4-Pentanediol
626-95-9

1,4-Pentanediol

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone60%
With Celite; silver carbonate In benzene for 1h; Heating;
With water; fluorine; acetonitrile In chloroform at -10 - 0℃;
With Rhodococcus ruber DSM 44541 In acetone at 30℃; for 48h; pH=7.5;
With palladium on activated charcoal at 120 - 300℃; Reagent/catalyst;
furfural
98-01-1

furfural

A

1,4-Pentanediol
626-95-9

1,4-Pentanediol

B

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With hydrogen In water at 80℃; under 1500.15 Torr; for 20.4167h; Pressure; Temperature; Reagent/catalyst; Autoclave;A 17%
B 56%
With hydrogen In water at 80℃; under 1500.15 Torr; for 20h;
3-acetyl-2-oxo-4,5-dihydrofuran
517-23-7

3-acetyl-2-oxo-4,5-dihydrofuran

A

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

B

3-hydroxy-4-(2-hydroxyethyl)-5-methylisoxazole
92745-95-4

3-hydroxy-4-(2-hydroxyethyl)-5-methylisoxazole

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine hydrochloride at 0 - 5℃; for 1h;A 24 % Chromat.
B 48%
1,4-Pentanediol
626-95-9

1,4-Pentanediol

A

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

B

4-oxopentanal
626-96-0

4-oxopentanal

C

5-methyl-dihydro-furan-2-one
108-29-2

5-methyl-dihydro-furan-2-one

Conditions
ConditionsYield
With oxygen In 2,4-dichlorophenoxyacetic acid dimethylamine; toluene at 80℃; for 4h;A n/a
B n/a
C 44%
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

C

1,4-Pentanediol
626-95-9

1,4-Pentanediol

D

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With hydrogen In water at 140℃; under 11251.1 Torr; for 4h; Autoclave;A 26%
B 8%
C 36%
D 18%
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

C

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With carbon dioxide; hydrogen In water at 80℃; under 30003 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Autoclave;A 11%
B 26%
C 10%
pent-1-yn-5-ol
5390-04-5

pent-1-yn-5-ol

A

5-(2-methyl-tetrahydrofuran-2-yloxy)pentan-2-one
7326-47-8

5-(2-methyl-tetrahydrofuran-2-yloxy)pentan-2-one

B

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With cisplatin In water at 37℃; for 48h;A 22%
B n/a

1071-73-4Relevant articles and documents

Solvent free permanganate oxidations

Shaabani, Ahmad,Lee, Donald G.

, p. 5833 - 5836 (2001)

The oxidations of organic compounds by permanganate under solvent free conditions have been studied. Thiols and primary aromatic amines undergo oxidative coupling reactions to give disulfides and diazenes, respectively, sulfides are oxidized to sulfones, primary and secondary alcohols are converted to aldehydes and ketones, 1,4-diols and cyclic ethers give lactones and arenes are oxidized to the corresponding α-ketones. The experimental procedure is simple and the products are easily isolated in good yields.

Regioselectivity in the Semiconductor-Mediated Photooxidation of 1,4-Pentanediol

Fox, Marye Anne,Ogawa, Haruo,Pichat, Pierre

, p. 3847 - 3852 (1989)

Optimum conditions have been established for the selective semiconductor-photocatalyzed oxidation by long-wavelength ultraviolet light of the primary alcohol functionality in 1,4-pentanediol.On platinized (2percent) TiO2 powder suspended in oxygenated aqueous (4 vol percent) acetonitrile, the initial rate ratio for oxidation of the primary/secondary alcohol site was > 7.Analysis of further oxidation products allowed for mechanistic delineation of the course of the semiconductor-mediated reaction.The selectivity is attributed to the essential role of adsorption, with the criticalphotoinduced electron transfer occurring at the surface of the irradiated particle.ZrO2 and SnO2 samples were much less active than TiO2 as photocatalysts.The effects of oxygen pressure, metal cocatalyst loading, and water content of acetonitrile are discussed.

Analytical methodology for determination of organic aerosol functional group distributions

Kalafut-Pettibone, Alicia J,McGivern, W. Sean

, p. 3553 - 3560 (2013)

Secondary organic aerosol (SOA) particles result from the condensation of oxidized volatile organic compounds (VOC) and consist of a complex mixture that is not conducive to complete compositional analysis. We present a simple methodology for determining the quantities of aldehydes and ketones, alcohols, and carboxylic acids in such samples via derivatization and high-performance liquid chromatography (HPLC) with ultraviolet-visible absorption detection and tandem mass spectrometry (MS/MS). Useful concentration ranges are presented with an examination of the specificity of these compounds in multiply substituted systems. Such data are valuable in modeling the formation of laboratory-generated aerosols and in identifying point sources of field-collected aerosol samples. Calibration curves on standard samples, MS/MS transitions, including collisionally induced dissociation (CID) products, and a quantitative examination of the specificity of the derivatization reagents toward multiple functional groups are presented for a series of aliphatic standard samples. These methods are then applied to filter extracts from SOA derived from 1-iodooctane photolysis at 254 nm to demonstrate the methodology on a complex system. Ultimately, this methodology enables the measurement of variations in the chemical nature of the oxygen within an SOA particle, providing a distribution of functional group concentrations. This article not subject to U.S. Copyright. Published 2013 by the American Chemical Society.

Fe(III)-porphyrin heterogenized on MCM-41: Matrix effects on the oxidation of 1,4-pentanediol

Molinari, Alessandra,Maldotti, Andrea,Bratovcic, Amra,Magnacca, Giuliana

, p. 64 - 69 (2011)

The metal complex iron meso-tetrakis (2,6-dichlorophenyl)porphyrin (Fe IIIP) has been covalently linked on the surface of the mesoporous material MCM-41 and of amorphous SiO2 to give the photocatalysts FeIIIP/MCM-41 and FeIIIP/SiO2 respectively. The effect of porphyrin addition on specific surface area and porosity of these materials has been evaluated by means of BET and BJH model applied to N 2 adsorption/desorption isotherms. It is seen that the MCM-41 sample presents the largest modification due to the presence of porphyrin: the pore size changes in average value and distribution, the pores formed in the presence of porphyrin being smaller and presenting a larger distribution. The photochemical characterization of FeIIIP/MCM-41 reveals that this is a robust photocatalyst able to induce the O2-assisted oxidation of 1,4-pentanediol. In particular, photoexcitation of FeIIIP/MCM-41 causes the conversion of 1,4-pentanediol to the aldehyde derivative compound with 70% regioselectivity. It is noteworthy that this product can be accumulated with no formation of further oxidized compounds. Due to its high specific surface area, which guarantees a good dispersion of the active centres, Fe IIIP/MCM-41 is about four times more efficient than Fe IIIP/SiO2. Moreover, the nature of the support controls the regioselectivity of the photocatalytic process: this is due to both uptake phenomena and steric effects, which can control the approach of the diol to the photoactive iron porphyrin.

Catalytic cascade conversion of furfural to 1,4-pentanediol in a single reactor

Liu, Fei,Liu, Qiaoyun,Xu, Jinming,Li, Lei,Cui, Yi-Tao,Lang, Rui,Li, Lin,Su, Yang,Miao, Shu,Sun, Hui,Qiao, Botao,Wang, Aiqin,Jér?me, Francois,Zhang, Tao

, p. 1770 - 1776 (2018)

The synthesis of bio-based linear diols is the subject of many research studies. However, one of the main obstacles in industrial development is the difficulty in controlling product selectivity. Here, we report the catalytic conversion of furfural to 1,4-pentanediol (PD) in the presence of Ru supported on an ordered mesoporous carbon (CMK-3) under pressure of H2 and CO2 in water. In contrast to previous catalytic pathways, this work is distinct in that it yields 1,4-PD as an exclusive product, instead of a mixture of 1,2- and 1,5-PD as usual. Under optimized conditions, 1,4-PD was obtained in 90% yield, and in a one-pot reaction, directly from furfural. We disclose that the conversion of furfural to 1,4-PD followed an unusual catalytic route. It implies a bifunctional catalytic pathway based on sequential catalytic hydrogenation reactions and an acid-catalyzed Piancatelli's rearrangement.

Tweaking the acid-sensitivity of transiently thermoresponsive Polyacrylamides with cyclic acetal repeating units

De Geest, Bruno G.,Van Herck, Simon

, (2020)

Merging the characteristics of thermoresponsive and stimuli-degradable polymers yields so-called transiently thermoresponsive polymers, which can find application for the design of injectable gels, nanoparticles, etc. within a biomedical context. Among these polymers, only a limited number is reported which shows selective degradation under mild acidic conditions. However, extension of the library of transiently thermoresponsive polymers is desired to broadening the biomaterials toolbox to suit specific needs. Three monomers were developed by modification of 2-hydroxyethylacrylamide (HEAm) via tetrahydropyranylation or -furanylation with 3,4-dihydro-2H-pyran (DHP), 2,3-dihydrofuran (DHF) or 2,3-dihydro-5-methylfuran (MeDHF). The presence of an acetal or ketal bond provided the monomers a pH-dependent hydrolysis behavior ranging from minutes to days. RAFT polymerisation allowed for the construction of homopolymers with temperature responsive behavior and pH-dependent hydrolysis which was strongly influenced by nature of the monomeric repeating units.

Catalytic production of 1,4-pentanediol from furfural in a fixed-bed system under mild conditions

Liu, Fei,Liu, Qiaoyun,Qiao, Botao,Su, Yang,Wang, Aiqin,Zhang, Leilei,Zhang, Tao

, p. 3532 - 3538 (2020)

Furfural is one of the most important biomass-derived chemicals. Its large-scale availability calls for the exploration of new transformation methods for further valorization. Here we report on the direct, one-step conversion of furfural into 1,4-pentanediols (1,4-PeDs) using a combination of Amberlyst-15 and Ru-FeOx/AC catalysts. It is interesting to find that the introduction of a suitable amount of FeOxresults in a great improvement in the dispersion of Ru and a decrease in the Lewis acidity. Both XPS and H2-TPR show that there is electron transfer from Ru to Fe, and the electronic interaction facilitates the reduction of both Ru and Fe species. When used in combination with Amberlyst-15, the Ru-6.3FeOx/AC catalyst afforded the best performance with a 1,4-PeD yield of 86%; by contrast, Ru/AC free of FeOxonly gave levulinic acid as the major product, demonstrating the key role of the acid/metal balance in the one-pot conversion of furfural to 1,4-PeD. Moreover, such a dual catalyst exhibited excellent durability within 175 h time-on-stream.

Palladium(II)-catalyzed oxidation of terminal alkenes to methyl ketones using molecular oxygen

Nishimura, Takahiro,Kakiuchi, Nobuyuki,Onoue, Tomoaki,Ohe, Kouichi,Ucmura, Sakae

, p. 1915 - 1918 (2000)

Palladium(II) acetate catalyzes the aerobic oxidation of terminal alkenes in toluene into the corresponding methyl ketones in the presence of a catalytic amount of pyridine using propan-2-ol as a reductant and molecular oxygen as an oxidant. Two catalytic cycles sharing a Pd(II)-OOH species are proposed. One is the formation of a Pd(II)-H species in the oxidation of propan-2-ol to acetone, followed by reaction with molecular oxygen to give a Pd(II)-OOH species, and the other is peroxypalladation of an alkene with the Pd(II)-OOH species produced to afford a methyl ketone in the presence of H2O2 produced by the former catalytic cycle. The Royal Society of Chemistry 2000.

Ru Nanoparticles on a Sulfonated Carbon Layer Coated SBA-15 for Catalytic Hydrogenation of Furfural into 1, 4-pentanediol

Cui, Kai,Qian, Wei,Shao, Zhengjiang,Zhao, Xiuge,Gong, Honghui,Wei, Xinjia,Wang, Jiajia,Chen, Manyu,Cao, Xiaoming,Hou, Zhenshan

, p. 2513 - 2526 (2021)

Furfural (FFR) is one of the most important biomass-derived chemicals. Its large-scale availability calls for the exploration of new transformation methods for further valorization. Herein, we demonstrate that Ru nanoparticles (Ru NPs)-supported on a sulfonated carbon layer coated SBA-15 can be employed as an efficient bi-functional catalyst for one step conversion of FFR into 1,4-pentanediol (1,4-PeDO). The optimum bi-functional catalyst can afford the full the conversion of FFR and 86% selectivity to 1,4-PeDO. The catalysts have been characterized thoroughly by using a complementary combination of powder X-ray diffraction, N2 adsorption–desorption, scanning/transmission electron microscopy, Fourier transform infrared spectroscopy, elemental analysis, and X-ray photoelectron spectroscopy. The characterization revealed that acidic groups (–SO3H) have been introduced on the surface of the carbon layer coated SBA-15 support after sulfonation with 98% H2SO4 and the surface acidity can be tuned facilely by the sulfonating time. Meantime, Ru(0) sites was highly dispersed via an impregnation and sequential reduction and directly adjacent to the surface –SO3H group. There existed an electronic interaction between Ru(0) sites and sulfonic groups, in which the electronic transfer from sulfonic sites to Ru(0) sites occurred. Br?nsted acid sites (–SO3H) have a significant influence on the FFR conversion and the selectivity to 1,4-PeDO. The ordered mesoporous structure, the appropriate density of acid sites and the electron-rich Ru(0) sites accounted for the the excellent performance of the catalyst for an efficient production of 1,4-PeDO from FFR. Graphic Abstract: [Figure not available: see fulltext.].

Supported gold nanoparticles as a reusable catalyst for synthesis of lactones from diols using molecular oxygen as an oxidant under mild conditions

Mitsudome, Takato,Noujima, Akifumi,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi

, p. 793 - 797 (2009)

The oxidative lactonization of various diols using molecular oxygen as a primary oxidant can be efficiently catalyzed by hydrotalcite-supported Au nanoparticles (Au/HT). For instance, lactonization of 1,4-butanediol gave γ-butyrolactone with an excellent turnover number of 1400. After lactonization, the Au/HT can be recovered by simple filtration and reused without any loss of its activity and selectivity.

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