Methyl 5-oxopentanoate supplier

Name
methyl 5-oxopentanoate
EINECS
CAS No. 6026-86-4
Article Data100
CAS DataBase
Density 1.013 g/cm³
Solubility
Melting Point 200-201 °C (decomp)
Formula C₆H₁₀O₃
Boiling Point 189.1 °C at 760 mmHg
Molecular Weight 130.144
Flash Point 72.1 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Glutaraldehydicacid, methyl ester (6CI,7CI,8CI);5-Oxopentanoic acid methyl ester;Methyl4-formylbutanoate;Methyl 4-formylbutyrate;Methyl 5-oxopentanoate;Methyl5-oxovalerate;Methyl glutaraldehydate;Methyl g-formylbutyrate;g-Formylbutyric acid methyl ester;
PSA 43.37000
LogP 0.52860

Synthetic route

: 14273-92-8
methyl 5-hydroxypentanoate

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With oxalyl dichloride; triethylamine In dichloromethane; dimethyl sulfoxide at -78 - 0℃; for 0.833333h; stereoselective reaction;	99%
Stage #1: methyl 5-hydroxypentanoate With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5h; Swern oxidation; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at -78 - 20℃; Swern oxidation; Inert atmosphere; Stage #3: With water; ammonium chloride In dichloromethane	95%
Stage #1: methyl 5-hydroxypentanoate With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5h; Stage #2: With triethylamine In dichloromethane at -78℃;	95%

: 1501-26-4
methyl 4-(chlorocarbonyl)butyrate

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; hydrogen; palladium on activated charcoal	95%
With 2,6-dimethylpyridine; hydrogen; palladium on activated charcoal In tetrahydrofuran	77%
With triethylsilane; palladium on activated charcoal for 1h; Ambient temperature;	72%

: 67-56-1
methanol

: 142-29-0
cyclopentene

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
Stage #1: methanol; cyclopentene With sodium hydrogencarbonate; ozone In dichloromethane at -78℃; Stage #2: With acetic anhydride; triethylamine In dichloromethane at 0℃; for 4.25h; Inert atmosphere;	95%
With oxygen; sodium hydrogencarbonate; ozone In dichloromethane at -78℃;	92%
Stage #1: methanol; cyclopentene With sodium hydrogencarbonate; ozone In dichloromethane at -78℃; Stage #2: With acetic anhydride; triethylamine In dichloromethane; benzene for 4h;	89%

: C7H13N3O3

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With (Bu4N)2S2O8 In 1,2-dichloro-ethane at 80℃; for 0.5h; oxidative cleavage;	91%

: 2396-80-7
methyl 5-hexenoate

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With potassium osmate(VI); sodium periodate In tetrahydrofuran; water at 20℃; for 3h;	76%
With potassium osmate(VI) dihydrate; sodium periodate In tetrahydrofuran; water at 20℃; for 3h;	59%
With sodium periodate; potassium osmate monohydrate In tetrahydrofuran; water at 20℃; for 3h;
Stage #1: methyl 5-hexenoate With ozone In dichloromethane at -78℃; for 1h; Stage #2: With dimethylsulfide In dichloromethane at -78 - 20℃;

: 30428-74-1
methyl 4-(N,N-diethylcarbamoyl)butyrate

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With Schwartz's reagent for 0.25h;	74%

: 1072-59-9
1-methoxycyclopentene

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With pyridine; ozone In methanol for 2h; Ring cleavage;	68%
With ozone In methanol at -78℃;	34%
With dimethylsulfide; ozone In methanol at -78℃;

: 542-28-9
3,4,5,6-tetrahydro-2H-pyran-2-one

: 67-56-1
methanol

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
Stage #1: 3,4,5,6-tetrahydro-2H-pyran-2-one; methanol With triethylamine at 20℃; for 18h; Stage #2: With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine at 20℃; for 14h;	65%
With sulfuric acid; pyridinium chlorochromate 1) reflux, 5 h, 2) CH2Cl2,, 23 deg C, 2 h; Yield given. Multistep reaction;
Stage #1: 3,4,5,6-tetrahydro-2H-pyran-2-one; methanol With sulfuric acid at 70℃; for 5h; Stage #2: With pyridinium chlorochromate In dichloromethane at 20℃; for 2h; Further stages.;
Stage #1: 3,4,5,6-tetrahydro-2H-pyran-2-one; methanol With sulfuric acid for 12h; Reflux; Stage #2: With pyridinium chlorochromate In dichloromethane at 29℃; for 5h;
Stage #1: 3,4,5,6-tetrahydro-2H-pyran-2-one; methanol With sulfuric acid Reflux; Stage #2: With oxalyl dichloride In dichloromethane; dimethyl sulfoxide at -78℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #3: With triethylamine In dichloromethane; dimethyl sulfoxide at 20℃; for 2h; Inert atmosphere; Schlenk technique;

: 108-24-7
acetic anhydride

: 142-29-0
cyclopentene

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
Stage #1: cyclopentene With sodium hydrogencarbonate; ozone In methanol; dichloromethane; benzene at 78℃; Stage #2: acetic anhydride With triethylamine In methanol; dichloromethane; benzene at 0℃; for 4h; Inert atmosphere;	60%
With oxygen; sodium hydrogencarbonate; ozone; triethylamine 1.) CH2Cl2, CH3OH, -70 deg C, 1.34 h, 2.) CH2Cl2, CH3OH, a) -20 deg C, 5 h, b) 8 deg C, 15 h; Yield given. Multistep reaction;

: 186581-53-3, 908094-01-9
diazomethane

: 142-29-0
cyclopentene

A: 6026-86-4
methyl 4-formylbutanoate

B: 1119-40-0
Dimethyl glutarate

C: 111-30-8
Glutaraldehyde

Conditions

Conditions	Yield
Stage #1: cyclopentene With ozone In dichloromethane at -78℃; Stage #2: With Merrifield resin-bound piperidine In dichloromethane at 20℃; for 24h; Stage #3: diazomethane In dichloromethane; ethyl acetate	A 59% B 14% C 23%

...Expand

: 67-56-1
methanol

: 99440-98-9
2-hydroxycyclopentanone

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene at 20℃; for 2h; Ring cleavage; methylation;	52%

: 5454-83-1
5-bromovaleric acid methyl ester

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With disodium hydrogenphosphate In dimethyl sulfoxide at 150℃; for 0.166667h;	43%

: 3240-34-4
[bis(acetoxy)iodo]benzene

: 62528-04-5
5-(4-methoxycarbonylbutyl)-3-methylthio-1,4-diphenyl-1,2,4-triazolium iodide

A: 6026-86-4
methyl 4-formylbutanoate

B: 13136-15-7
1,4-Diphenyl-3-methylmercapto-1,2,4-triazolium iodide

Conditions

Conditions	Yield
With iodine; sodium methylate; potassium iodide 1.) CHCl3, reflux, 30 min, 2.) MeOH, room temp, 15 min; Yield given. Multistep reaction;	A n/a B 35%

...Expand

: 10316-66-2
2-hydroxy-2-cyclohexen-1-one

A: 110-94-1
1,5-pentanedioic acid

B: 5746-02-1
5-oxopentanoic acid

C: 6026-86-4
methyl 4-formylbutanoate

D: 22191-05-5
methyl 5-methoxycarbonyl-2-hydroxypentanoate

E: 86544-11-8
methyl 5-carboxy-2-hydroxypentanoate

F: 139125-23-8
2-Oxo-hexanedioic acid dimethyl ester

Conditions

Conditions	Yield
With oxygen; CuCl2*2H2O In methanol at 25℃; under 760 Torr; for 5h; Mechanism; various 1,2-cyclohexanediones;	A n/a B 8% C 5% D 12% E 8% F 3%

...Expand

: 67-56-1
methanol

: 5-oxo-valeryl chloride

: 6026-86-4
methyl 4-formylbutanoate

: 86290-14-4
2,2-dimethoxy-3,4-dihydropyrane

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With hydrogenchloride
With oxonium; sodium chloride In dichloromethane for 8h; Ambient temperature; pH= 4; Yield given;

: 623-43-8
crotonic acid methyl ester

: 201230-82-2
carbon monoxide

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With hydrogen; Rh catalyst at 150℃;

: 542-28-9
3,4,5,6-tetrahydro-2H-pyran-2-one

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With methanol; hydrogen cation; pyridinium chlorochromate 2.) CH2Cl2; Yield given. Multistep reaction;
With swern reagent Multistep reaction;
Multi-step reaction with 2 steps 1: (COCl)2; DMSO; Et3N View Scheme

: 67-56-1
methanol

: 930-29-0
1-chlorocyclopent-1-ene

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With dimethylsulfide; sodium methylate; ozone 1.) -78 deg C, 2.) -78 deg C, 3.) 1h; Yield given. Multistep reaction;

: 13392-69-3
valeric acid

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With pyridinium chlorochromate Multistep reaction;

: 5-Hydroperoxy-5-methoxy-pentanal

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With acetic anhydride; triethylamine for 24h; Ambient temperature; Yield given;

: 201991-68-6
(8Z,11Z,14Z)-5,6-Dihydroxy-icosa-8,11,14-trienoic acid methyl ester

A: 6026-86-4
methyl 4-formylbutanoate

B: 13552-98-2
(3Z,6Z,9Z)-pentadeca-3,6,9-trienal

Conditions

Conditions	Yield
With lead(IV) acetate In dichloromethane at 78℃; for 0.333333h;

: 67-56-1
methanol

: 22498-31-3
2-nitrocyclopentan-1-one

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With potassium hydroxide; potassium permanganate; magnesium sulfate 1.) reflux, 8 h, 2.) H2O, room temperature, 12 h; Yield given. Multistep reaction;

: 23068-91-9
methyl 5,5-dimethoxyvalerate

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid; water In tetrahydrofuran at 17 - 22℃; for 5h;

: 7647-01-0
hydrogenchloride

: 86290-14-4
2,2-dimethoxy-3,4-dihydropyrane

: 6026-86-4
methyl 4-formylbutanoate

: 67-56-1
methanol

: 142-29-0
cyclopentene

A: 4454-05-1
2-methoxy-3,4-dihydro-2H-pyran

B: 6026-86-4
methyl 4-formylbutanoate

C: 23068-91-9
methyl 5,5-dimethoxyvalerate

D: 1119-40-0
Dimethyl glutarate

E: 4454-02-8
1,1,5,5-tetramethoxy-pentane

F: 111-30-8
Glutaraldehyde

G cis- and trans-2,6-dimethoxytetrahydropyran, CH3Cl: cis- and trans-2,6-dimethoxytetrahydropyran, CH3Cl

Conditions

Conditions	Yield
With hydrogenchloride; ozone Product distribution; Mechanism; -78 deg to r.t.;	A n/a B 2 % Chromat. C 46 % Chromat. D 23 % Chromat. E 27 % Chromat. F 1 % Chromat. G n/a

...Expand

: 200956-99-6
5,6-Epoxyeicosatrienoic acid methyl ester

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) 10:1 formic acid-acetic anhydride; 2) sodium methoxide / 1) 12h, 25 deg C; 2) methanol, 2h, 25 deg C 2: lead tetraacetate / CH2Cl2 / 0.33 h / 78 °C View Scheme

: 108-55-4
glutaric anhydride,

: 6026-86-4
methyl 4-formylbutanoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.) SOCl2 2: reduction View Scheme

: 3724-55-8
methyl but-3-enoate

: 201230-82-2
carbon monoxide

A: 6026-86-4
methyl 4-formylbutanoate

B: 65038-34-8
3-formyl-butyric acid methyl ester

Conditions

Conditions	Yield
With hydrogen; acetic acid; acetylacetonatodicarbonylrhodium(l) In tetrahydrofuran at 40℃; under 7500.75 Torr; for 4h; Title compound not separated from byproducts.;
With dicarbonyl(acetylacotonato)rhodium(I); C59H50N4O2P2 In dichloromethane at 40℃; for 24h; regioselective reaction;
With acetylacetonatodicarbonylrhodium(l); [(C6H5)2PC6H4CONHC6H3C2NH(CH3)]2CH(C2H5); hydrogen; triethylamine In dichloromethane at 40℃; under 15001.5 Torr; for 24h; Autoclave; Schlenk technique; Inert atmosphere; regioselective reaction;

...Expand

: 6026-86-4
methyl 4-formylbutanoate

: 868-59-7
L-cysteine ethyl ester hydrochloride

: 226888-62-6
(R)-2-(3-Methoxycarbonyl-propyl)-thiazolidine-4-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With magnesium sulfate; potassium carbonate In toluene Ambient temperature;	100%

: 6026-86-4
methyl 4-formylbutanoate

: 1402910-17-1
(E)-isopropyl 4-(4-chlorophenyl)-2-oxobut-3-enoate

: isopropyl 4-(4-chlorophenyl)-2-hydroxy-3-(3-methoxy-3-oxopropyl)-3,4-dihydro-2H-pyran-6-carboxylate

Conditions

Conditions	Yield
With trans-perhydroindolic acid; ortho-chlorobenzoic acid In isopropyl alcohol at 20℃; for 72h; Michael Addition;	99%

: 6026-86-4
methyl 4-formylbutanoate

: 1402910-12-6
(E)-isopropyl 4-(2-fluorophenyl)-2-oxobut-3-enoate

: isopropyl 4-(2-fluorophenyl)-2-hydroxy-3-(3-methoxy-3-oxopropyl)-3,4-dihydro-2H-pyran-6-carboxylate

Conditions

Conditions	Yield
With trans-perhydroindolic acid; ortho-chlorobenzoic acid In isopropyl alcohol at 20℃; for 72h; Michael Addition;	99%

: 6026-86-4
methyl 4-formylbutanoate

: 1239709-09-1
pent-3-yn-1-yltriphenylphosphonium iodide

: 1326454-05-0
(Z)-dec-5-en-8-ynoic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol for 3h; Wittig Olefination; Reflux; stereoselective reaction;	99%

: 6026-86-4
methyl 4-formylbutanoate

: 108-98-5
thiophenol

: 896730-40-8
5,5-bis-phenylsulfanyl-pentanoic acid methyl ester

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -50℃; for 0.5h;	98%

: 6026-86-4
methyl 4-formylbutanoate

: 679841-28-2
benzyl 2-oxo-4-phenylbut-3-enoate

: benzyl 2-hydroxy-3-(3-methoxy-3-oxopropyl)-4-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

Conditions

Conditions	Yield
With trans-perhydroindolic acid; ortho-chlorobenzoic acid In isopropyl alcohol at 20℃; for 72h; Michael Addition;	98%

: 6026-86-4
methyl 4-formylbutanoate

: N-methylcamphanylpiperazine

: 76782-82-6
tert-Butyldimethyl(prop-2-ynyloxy)silane

: C28H50N2O3Si

Conditions

Conditions	Yield
With copper(I) bromide In toluene at 25℃; for 24h; diastereoselective reaction;	98%

...Expand

: 6026-86-4
methyl 4-formylbutanoate

: 154-09-6, 526-53-4, 2899-29-8, 52485-52-6
L-tryptophanol

: 778591-55-2
(6S,12bR)-1,2,3,6,7,12b-hexahydro-6-(hydroxymethyl)indolo[2,3-a]quinolizin-4(12H)-one

Conditions

Conditions	Yield
Stage #1: methyl 4-formylbutanoate; L-tryptophanol In toluene for 48h; Heating; Stage #2: With hydrogenchloride In ethanol; water at 20℃; for 20h; Further stages.;	95%

: 6026-86-4
methyl 4-formylbutanoate

: isopropyl (E)-2-oxo-4-phenylbut-3-enoate

: isopropyl 2-hydroxy-3-(3-methoxy-3-oxopropyl)-4-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

Conditions

Conditions	Yield
With trans-perhydroindolic acid; ortho-chlorobenzoic acid In isopropyl alcohol at 20℃; for 72h; Reagent/catalyst; Time; Solvent;	95%

: 6026-86-4
methyl 4-formylbutanoate

: C14H13F3O3

: isopropyl 2-hydroxy-3-(3-methoxy-3-oxopropyl)-4-[4-(trifluoromethyl)phenyl]-3,4-dihydro-2H-pyran-6-carboxylate

Conditions

Conditions	Yield
With trans-perhydroindolic acid; ortho-chlorobenzoic acid In isopropyl alcohol at 20℃; for 72h; Michael Addition;	95%

: 6026-86-4
methyl 4-formylbutanoate

: 80582-39-4
(2S)-2-amino-3-(3,4-dimethoxyphenyl)-1-propanol

: 3-(3,4-dimethoxy-benzyl)-hexahydro-oxazolo[3,2-a]pyridin-5-one

Conditions

Conditions	Yield
In toluene Heating;	94%

: 6026-86-4
methyl 4-formylbutanoate

: 1402910-15-9
(E)-isopropyl 4-(3-bromophenyl)-2-oxobut-3-enoate

: isopropyl 4-(3-bromophenyl)-2-hydroxy-3-(3-methoxy-3-oxopropyl)-3,4-dihydro-2H-pyran-6-carboxylate

Conditions

Conditions	Yield
With trans-perhydroindolic acid; ortho-chlorobenzoic acid In isopropyl alcohol at 20℃; for 72h; Michael Addition;	94%

Methyl 5-oxopentanoate Specification

The Methyl 5-oxopentanoate, with the CAS registry number 6026-86-4, is also known as Pentanoic acid, 5-oxo-, methyl ester. This chemical's molecular formula is C₆H₁₀O₃ and molecular weight is 130.1418. Its systematic name is called methyl 5-oxopentanoate.

Physical properties of Methyl 5-oxopentanoate: (1)ACD/LogP: 0.33; (2)ACD/LogD (pH 5.5): 0.33; (3)ACD/LogD (pH 7.4): 0.33; (4)ACD/BCF (pH 5.5): 1.05; (5)ACD/BCF (pH 7.4): 1.05; (6)ACD/KOC (pH 5.5): 35.96; (7)ACD/KOC (pH 7.4): 35.96; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 5; (10)Index of Refraction: 1.41; (11)Molar Refractivity: 31.8 cm³; (12)Molar Volume: 128.3 cm³; (13)Surface Tension: 31.6 dyne/cm; (14)Density: 1.013 g/cm³; (15)Flash Point: 72.1 °C; (16)Enthalpy of Vaporization: 42.53 kJ/mol; (17)Boiling Point: 189.1 °C at 760 mmHg; (18)Vapour Pressure: 0.579 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=CCCCC(=O)OC
(2)InChI: InChI=1/C6H10O3/c1-9-6(8)4-2-3-5-7/h5H,2-4H2,1H3
(3)InChIKey: YBTZROCKNUIONO-UHFFFAOYAV

Product Name

methyl 5-oxopentanoate

Synthetic route

Methyl 5-oxopentanoate Specification

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