delta-Valerolactone supplier

Name
delta-Valerolactone
EINECS 208-807-1
CAS No. 542-28-9
Article Data409
CAS DataBase
Density 1.065 g/cm³
Solubility miscible with water
Melting Point -13 °C
Formula C₅H₈O₂
Boiling Point 218 °C at 760 mmHg
Molecular Weight 100.117
Flash Point 81 °C
Transport Information
Appearance clear colorless to pale yellow liquid
Safety 26-39
Risk Codes 41
Molecular Structure
Hazard Symbols Xi
Synonyms Valericacid, 5-hydroxy-, d-lactone (6CI);1-Oxacyclohexan-2-one;2-Oxotetrahydropyran;5-Hydroxypentanoic acid lactone;5-Hydroxypentanoic acid d-lactone;5-Valerolactone;NSC6247;Pentan-5-olide;Pentanoic acid, 5-hydroxy-, d-lactone;Tetrahydro-2-pyranone;Tetrahydro-2H-pyran-2-one;d-Valerolactone;d-Valeryllactone;
PSA 26.30000
LogP 0.71350

Synthetic route

: 3393-45-1
5,6-dihydro-pyran-2-one

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

Conditions

Conditions	Yield
With hydrogen; palladium(II) complex of ferrocenylamine sulfide (1) In acetone under 4137.2 Torr; for 10h;	100%

: 111-29-5
1 ,5-pentanediol

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

Conditions

Conditions	Yield
With sodium hypochlorite; sodium hydrogencarbonate; potassium bromide In dichloromethane at 0℃; for 0.5h; chemoselective reaction;	99%
With sodium bromite In water; acetic acid for 10h; Ambient temperature;	98%
With 4-hydroxy-TEMPO benzoate; sodium bromide In dichloromethane; water NaHCO3-buffered at pH 8.6; electrolysis;	97%

: 120-92-3
cyclopentanone

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

Conditions

Conditions	Yield
With Octanoic acid; dihydrogen peroxide In water at 50℃; for 5h; Baeyer-Villiger oxidation; Ionic liquid; Enzymatic reaction;	99%
With dihydrogen peroxide; lithium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate In water; 1,2-dichloro-ethane at 70℃; for 2h; Time; Temperature; Reagent/catalyst;	99%
With dihydrogen peroxide; polystyrene-bound phenylselenic acid In dichloromethane for 72h; Ambient temperature;	98%

: 13392-69-3
valeric acid

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

Conditions

Conditions	Yield
With molecualar sevies 4A; tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene at 120℃; for 10h;	98%
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 10h; Heating;	96%
With cis-nitrous acid at 25℃; Rate constant;
Equilibrium constant; Rate constant;

: propyl 5-hydroxyvalerate

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

Conditions

Conditions	Yield
With 732 sulfonic acid type cation exchange resin at 150℃; for 2h; Time;	96.31%

: 13107-53-4
ethyl 2-hydroxyethylpropionate

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

Conditions

Conditions	Yield
With 732 sulfonic acid type cation exchange resin at 130℃; for 1.5h;	96.05%

: 1119-46-6
5-chloro-valeric acid

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

Conditions

Conditions	Yield
With sodium hydroxide for 0.166667h; Heating;	96%
With triethylamine at 50℃; under 3750300 Torr; for 3h;	90%
With cyclohexene In gas at 349.5℃; for 0.1h; Rate constant; stoichometry;	44.3%

: 2067-33-6
5-bromopentanoic acid

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

Conditions

Conditions	Yield
With potassium fluoride; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20℃; for 5h;	96%
With Amberlyst A26 (hydrogen carbonate form) 1.) aq. MeOH, 20 deg C, 18 h, 2.) THF, reflux, 18 h; Yield given. Multistep reaction;
With potassium carbonate In water; dimethyl sulfoxide at 50℃; Rate constant;
With 2,3,3-trimethylbenzo[e]indole; potassium iodide In acetonitrile at 80 - 85℃; for 96h;

: 14273-92-8
methyl 5-hydroxypentanoate

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

Conditions

Conditions	Yield
With 732 sulfonic acid type cation exchange resin at 100℃; for 1h; Time;	95.08%
porcine pancreatic lipase In diethyl ether at 26℃;

: 110-63-4
Butane-1,4-diol

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

Conditions

Conditions	Yield
With trichloromelamine In dichloromethane for 12h; Mechanism; Ambient temperature;	95%

: 2508-29-4
5-hydroxypentylamine

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

Conditions

Conditions	Yield
With hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor In water for 15h; pH=5.5; Enzymatic reaction; chemoselective reaction;	95%

: 142-68-7
TETRAHYDROPYRANE

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

Conditions

Conditions	Yield
With potassium permanganate; iron(III) chloride In acetone at -78 - 20℃; for 16h;	92%
With zinc(II) permanganate; silica gel In dichloromethane at 20℃; for 0.17h;	69%
Stage #1: TETRAHYDROPYRANE With [bis(acetoxy)iodo]benzene In nitromethane at 0℃; Stage #2: With tert.-butylhydroperoxide In decane; nitromethane at 0 - 25℃; for 12h;	68%

: 96-41-3
Cyclopentanol

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

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 60℃; for 20h;	92%
With dihydrogen peroxide In water at 20℃; for 7h; Baeyer-Villiger-type reaction;	92%
With water; fluorine In acetonitrile
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 60℃; for 24h; Product distribution; Mechanism; other solvent;

: 4221-03-8
5-hydroxypentanal

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

Conditions

Conditions	Yield
With N-iodo-succinimide; silver(I) acetate In benzene for 3h; Heating;	90%
With dihydrogen peroxide; acetic acid
With manganese(IV) oxide; chloroform
With cobalt(II) acetate at 80 - 90℃; beim Beh. mit Luft;

: trimethylsilyl 5-iodopentanoate

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

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h;	90%

: 64-19-7
acetic acid

: 120-92-3
cyclopentanone

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

B: 26976-70-5
5-acetoxypentanoic acid

Conditions

Conditions	Yield
With peracetic acid 1.) 50-60 deg C, 6 h; 2.) reflux, 29 h;	A n/a B 85.5%
With peracetic acid 1.) 50-60 deg C, 6 h; 2.) reflux, 29 h; Yields of byproduct given;	A n/a B 85.5%

...Expand

: 77023-79-1
(CO)5MnCO(CH2)4OSi(CH3)3

: 59201-86-4
tris(diethylamino)sulfonium difluorotrimethylsiliconate

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

B: 89020-18-8
(CO)5Mn(1-)*{(CH3CH2)2N}3S(1+)=(CO)5Mn{(CH3CH2)2N}3S

Conditions

Conditions	Yield
In tetrahydrofuran flask charged with ((CH3CH2)2N)3SSi(CH3)3F2, NMR standard and THF, complex in THF added dropwise for 0.5 h with stirring, stirred for 2 h; not isolated, detected by IR;	A 85% B n/a

...Expand

: 73819-79-1, 73819-80-4
<α-tetrahydropyrannyloxy>-2 tetrahydropyrone-3 (S*, S*)

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

B: 23462-75-1
5,6-dihydro-2H-pyran-3(4H)-one

: 73819-79-1, 73819-80-4
<α-tetrahydropyrannyloxy>-2 tetrahydropyrone-3 (S*, R*)

Conditions

Conditions	Yield
With further temp. In benzene at 80℃; for 1.5h; Product distribution; Irradiation;	A 82% B 16% C 5%

...Expand

: ethyl valerolactonium tetrafluoroborate

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

B: 41302-32-3
ethyl 5-iodopentanoate

Conditions

Conditions	Yield
With sodium iodide In dichloromethane; acetonitrile	A 18% B 82%

: 7681-84-7
tetrahydrofuran-2-carbaldehyde

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

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In dichloromethane at 20℃; for 5h; Inert atmosphere;	82%

: 4676-84-0
tetrahydropyran-2-yl hydroperoxide

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

Conditions

Conditions	Yield
With tert-butylhypochlorite In acetonitrile at 20℃; for 0.166667h;	78%

: 108-55-4
glutaric anhydride,

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

Conditions

Conditions	Yield
With lithium borohydride In tetrahydrofuran for 0.25h;	77%
With ethanol; sodium

: 109-52-4
valeric acid

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

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

Conditions

Conditions	Yield
With sodium persulfate In water at 85 - 90℃; for 5h;	A 9% B 77%

: C6H11O2(1+)*BF4(1-)

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

B: 14273-88-2
methyl 5-iodopentanoate

Conditions

Conditions	Yield
With sodium iodide In dichloromethane; acetonitrile	A 29% B 71%

: 628-21-7
1,4-Diiodobutane

Mo(CO)6: Mo(CO)6

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

Conditions

Conditions	Yield
With potassium fluoride; 18-crown-6 ether; water In tetrahydrofuran for 20h; Heating;	70%

: 142-68-7
TETRAHYDROPYRANE

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

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

Conditions

Conditions	Yield
With sodium bromate; potassium hydrogensulfate In water at 25 - 30℃; for 20h; Oxidation;	A 69% B 16%
With 2,6-dichloropyridine N-oxide; dichloro(5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)ruthenium(IV) In 1,2-dichloro-ethane at 40℃; for 20h; Reagent/catalyst; Inert atmosphere;	A 56% B 16%

: 108-93-0
cyclohexanol

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

B: 124-04-9
Adipic acid

C: 54812-72-5
monocyclohexyl adipate

D: 108-94-1
cyclohexanone

Conditions

Conditions	Yield
With oxygen at 120℃; for 4.33333h; Further byproducts given;	A 2.7% B 12.4% C 8.9% D 65%

...Expand

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

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

Conditions

Conditions	Yield
With hydrogen In methanol at 375℃; for 5h; Reagent/catalyst; Time; Solvent;	65%
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 2: [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](borohydride)(carbonyl)(hydride)iron(II); potassium carbonate / toluene / 5 h / 150 °C / Inert atmosphere; Green chemistry View Scheme

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

: 37435-69-1
5-hydroxypentanoic acid sodium salt

Conditions

Conditions	Yield
With water; sodium hydroxide at 20℃; Inert atmosphere;	100%
With sodium hydroxide In ethanol at 20 - 80℃; for 2.5h;	100%
With sodium hydroxide at 20℃; for 24h;	83%

: 123-75-1
pyrrolidine

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

: 73200-35-8
5-hydroxy-1-(pyrrolidin-1-yl)pentan-1-one

Conditions

Conditions	Yield
With triethylamine Inert atmosphere; Reflux;	100%
In benzene	82%

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

: 67-56-1
methanol

: 14273-92-8
methyl 5-hydroxypentanoate

Conditions

Conditions	Yield
With Dowex 50W-X8 resin at 20℃; Inert atmosphere; Reflux;	100%
With sulfuric acid for 5h; Heating;	99%
With H+ Dowex resin Heating;	99%

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

: 107-11-9
1-amino-2-propene

: 133055-24-0
N-allyl-5-hydroxypentanamide

Conditions

Conditions	Yield
	100%
In ethanol for 15h; Heating;	63%
With bis(trifluoromethane)sulfonimide lithium In chloroform at 85℃; for 40h;	5%

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

: 109-94-4
formic acid ethyl ester

: Sodium; [2-oxo-dihydro-pyran-(3Z)-ylidene]-methanolate

Conditions

Conditions	Yield
With sodium hydride	100%

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

: 111-29-5
1 ,5-pentanediol

Conditions

Conditions	Yield
With trimethoxysilane; lithium methanolate In tetrahydrofuran for 0.5h; Ambient temperature;	100%
With hydrogen In 1,2-dimethoxyethane at 80℃; under 60006 Torr; for 2h; Reagent/catalyst;	87.7%
With sodium tetrahydroborate; C36H30F6N10Ni4O10(2+)*2C2F3O2(1-); zinc(II) chloride In tetrahydrofuran at 45℃; for 12h;	79%

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

: (E)-benzyl 4,4,4-trifluoro-3-(trifluoromethyl)but-2-enoate

: (3S*,2'S*)-Benzyl 3-pentan-5'-olid-2'-yl-3-(trifluoromethyl)propionate

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) -78 deg C;	100%

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

: 2687-43-6
O-benzylhydoxylamine hydrochloride

: N-(benzyloxy)-5-hydroxypentanamide

Conditions

Conditions	Yield
With trimethylaluminum In tetrahydrofuran; toluene	100%
Stage #1: O-benzylhydoxylamine hydrochloride With trimethylaluminum In tetrahydrofuran; toluene at 0 - 20℃; for 0.833333h; Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In tetrahydrofuran; toluene at 0℃; for 1.5h;	50%

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

: 14273-92-8
methyl 5-hydroxypentanoate

Conditions

Conditions	Yield
With triethylamine In methanol at 20℃; for 1h; Inert atmosphere; Large scale;	100%
Stage #1: 3,4,5,6-tetrahydro-2H-pyran-2-one With sulfuric acid In methanol for 12h; Reflux; Stage #2: With sodium hydrogencarbonate In methanol for 0.166667h; stereoselective reaction;	99%
With sulfuric acid In methanol for 12h; Reflux;	94%
With sulfuric acid In methanol for 21h; Inert atmosphere; Reflux;	85%

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

: 2338-18-3
2-aminoindane hydrochloride

: 1148156-44-8
N-(indan-2-yl)-5-hydroxypentanamide

Conditions

Conditions	Yield
With aluminum (III) chloride; triethylamine In 1,2-dichloro-ethane at 20℃; for 1h;	100%

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

: 536-74-3
phenylacetylene

: 67654-84-6
5-oxo-5-(2-phenylethynyl)-1-pentanol

Conditions

Conditions	Yield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; for 0.166667h; Stage #3: 3,4,5,6-tetrahydro-2H-pyran-2-one In tetrahydrofuran at -78 - 20℃; for 1h;	99%
(i) nBuLi, hexane, THF, (ii) /BRN= 106436/; Multistep reaction;

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

: 95-16-9
1,3-Benzothiazole

: 85450-44-8
1-(benzo[d]thiazol-2-yl)-5-hydroxypentan-1-one

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane -78 deg C, 1 h; to RT, 30 min;	99%
Stage #1: 1,3-Benzothiazole With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water	37%
Stage #1: 1,3-Benzothiazole With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water	6.5 g

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

: 32704-22-6
2-allyl-phenylamine

: 114877-79-1
5-Hydroxy-pentanoic acid (2-allyl-phenyl)-amide

Conditions

Conditions	Yield
With dimethylaluminum chloride In dichloromethane for 1h; Ambient temperature;	99%

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

: 110824-26-5
tert-butyl(diphenyl)(2-propynyloxy)silane

: 137445-61-5
1-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-oct-2-yn-4-one

Conditions

Conditions	Yield
	99%

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

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 187756-41-8
5-hydroxy-N,O-dimethyl-pentanohydroxamic acid

Conditions

Conditions	Yield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With trimethylaluminum In dichloromethane at 0℃; for 0.333333h; Inert atmosphere; Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In dichloromethane at 0℃; for 0.333333h; Inert atmosphere; Stage #3: With hydrogenchloride In dichloromethane; chloroform; water at 0℃; for 1h; Inert atmosphere;	99%
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With trimethylaluminum In hexane; dichloromethane at 0℃; Inert atmosphere; Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In hexane; dichloromethane at 0℃; Inert atmosphere; Stage #3: With hydrogenchloride In hexane; dichloromethane; chloroform; water at 0℃;	92%
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With trimethylaluminum In hexane; dichloromethane at 0℃; for 0.333333h; Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In hexane; dichloromethane at 0℃; for 0.333333h;	92%

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

: 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

: 1,5-bis((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)pentane

Conditions

Conditions	Yield
With C12H36MgN2Si4 In neat (no solvent) at 20℃; for 0.25h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;	99%

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

: Tebbe's reagent

: 38614-15-2
2-methylidenetetrahydropyran

Conditions

Conditions	Yield
In benzene-d6 for 0.25h;	99%

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

: 2798-73-4, 3685-19-6, 3685-20-9
(Z)-1-methoxybut-1-en-3-yne

: 112320-60-2
9-hydroxy-1-methoxynon-1-en-3-yn-5-one

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃; for 1h;	98%
With n-butyllithium 1) THF, -78 deg C, 50 min, 2) -78 deg C, 30 min; Yield given. Multistep reaction;
With n-butyllithium 1.) THF, hexane, -78 deg C, 1 h, 2.) -78 deg C, 1 h; Multistep reaction;

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

: 1468-95-7
9-hydroxymethylanthracene

poly(δ-valerolactone), asymmetric, telechelic, initiated by 9-anthracenemethanol/HCl*Et2O, Mn(NMR)=6900, Mw/Mn=1.1; monomer(s): δ-valerolactone; 9-anthracenemethanol: poly(δ-valerolactone), asymmetric, telechelic, initiated by 9-anthracenemethanol/HCl*Et2O, Mn(NMR)=6900, Mw/Mn=1.1; monomer(s): δ-valerolactone; 9-anthracenemethanol

Conditions

Conditions	Yield
With hydrochloric acid diethyl ether In dichloromethane at 0℃; for 2h; Product distribution; Further Variations:; δ-valerolactone/9-anthracenemethanol ratio;	98%

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

: 540-51-2
2-bromoethanol

poly(δ-valerolactone), asymmetric, telechelic, initiated by 2-bromoethanol/HCl*Et2O, Mn(NMR)=11000, Mw/Mn=1.10; monomer(s): δ-valerolactone; 2-bromoethanol: poly(δ-valerolactone), asymmetric, telechelic, initiated by 2-bromoethanol/HCl*Et2O, Mn(NMR)=11000, Mw/Mn=1.10; monomer(s): δ-valerolactone; 2-bromoethanol

Conditions

Conditions	Yield
With hydrogenchloride; diethyl ether In dichloromethane at 0℃; for 2.5h;	98%

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

: 71-36-3
butan-1-ol

poly(δ-valerolactone), initiated by 1-butanol/HCl*Et2O, Mn(exp)=19000, Mw/Mn=1.06; monomer(s): 1-butanol; δ-valerolactone: poly(δ-valerolactone), initiated by 1-butanol/HCl*Et2O, Mn(exp)=19000, Mw/Mn=1.06; monomer(s): 1-butanol; δ-valerolactone

Conditions

Conditions	Yield
With hydrochloric acid diethyl ether In dichloromethane at 0℃; for 1.5h; Product distribution; Further Variations:; Temperatures; react. times; δ-VL/1-butanol rat.; init. δ-VL conc.; HCl/1-C4H9OH rat.;	98%

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

: 818-61-1
2-hydroxyethyl acrylate

poly(δ-valerolactone), asymmetric, telechelic, initiated by 2-hydroxyethyl acrylate/HCl*Et2O, Mn(NMR)=11000, Mw/Mn=1.08; monomer(s): δ-valerolactone; 2-hydroxyethyl acrylate: poly(δ-valerolactone), asymmetric, telechelic, initiated by 2-hydroxyethyl acrylate/HCl*Et2O, Mn(NMR)=11000, Mw/Mn=1.08; monomer(s): δ-valerolactone; 2-hydroxyethyl acrylate

Conditions

Conditions	Yield
With hydrogenchloride; diethyl ether In dichloromethane at 0℃; for 2.5h;	98%

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

: 7585-39-9
β‐cyclodextrin

polymer; monomer(s): β-cyclodextrin; δ-valerolactone: polymer; monomer(s): β-cyclodextrin; δ-valerolactone

Conditions

Conditions	Yield
at 100℃; for 48h;	98%

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

: 141-78-6
ethyl acetate

: 529510-37-0
ethyl (3R)-3,7-dihydroxyheptanoate

Conditions

Yield

Stage #1: ethyl acetate With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In tetrahydrofuran at -78℃; for 3h; Inert atmosphere;
Stage #3: With ruthenium trichloride; hydrogen; (+)-(R)-[2,3,2',3'-tetrahydro-5,5'-bi(1,4-benzodioxin)-6,6'-diyl]bis(diphenylphosphane) In ethanol at 80℃; under 7500.75 Torr; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

98%

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

: 13472-85-0
2-methoxy-5-bromopyridine

: 1134621-15-0
5-hydroxy-1-(6-methoxypyridin-3-yl)pentan-1-one

Conditions

Conditions	Yield
Stage #1: 2-methoxy-5-bromopyridine With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In diethyl ether; hexane at -78 - 20℃; Inert atmosphere; regioselective reaction;	98%
Stage #1: 2-methoxy-5-bromopyridine With n-butyllithium In diethyl ether; hexane at -78 - 20℃; Inert atmosphere; Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In diethyl ether; hexane at -78 - 20℃; Inert atmosphere; regioselective reaction;	98%
Stage #1: 2-methoxy-5-bromopyridine With n-butyllithium In diethyl ether; hexane at -78℃; for 0.25h; Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In diethyl ether; hexane at -78 - 20℃;	85%

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

: 59145-82-3
N,5-dihydroxypentanamide

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; potassium hydroxide In methanol at 0 - 20℃; Inert atmosphere;	98%
With hydroxylamine hydrochloride; potassium hydroxide In methanol

delta-Valerolactone Specification

The IUPAC name of delta-Valerolactone is oxan-2-one. With the CAS registry number 542-28-9, it is also named as Penta-1,5-lactone. The product's categories are Functional Materials; Lactones & Lactides (for High-Performance Polymer Research); Reagent for High-Performance Polymer Research. It is clear colorless to pale yellow liquid which can polymerize easily. Additionally, this chemical should be sealed in the container and stored in the cool and dry place. Keep away from acids and food chemicals.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.20; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.2; (4)ACD/LogD (pH 7.4): -0.2; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 18.54; (8)ACD/KOC (pH 7.4): 18.54; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.44; (13)Molar Refractivity: 24.79 cm³; (14)Molar Volume: 93.9 cm³; (15)Surface Tension: 33.4 dyne/cm; (16)Enthalpy of Vaporization: 45.44 kJ/mol; (17)Vapour Pressure: 0.129 mmHg at 25°C; (18)Tautomer Count: 2; (19)Exact Mass: 100.05243; (20)MonoIsotopic Mass: 100.05243; (21)Topological Polar Surface Area: 26.3; (22)Heavy Atom Count: 7; (23)Complexity: 78.1.

Preparation of delta-Valerolactone: It can be obtained by many methods. Such as: it can be produced by cyclopentanone that is treated by benzoic acid.

Uses of delta-Valerolactone: It is used as raw material in the production of valeric acid derivatives. And it is also used to produce valerolactam and polyester. In addition, it can react with chloromethyl-oxirane to get 2-chloromethyl-1,4,6-trioxa-sπro[4.5]decane. This reaction needs reagents tetrachloromethane and boron fluoride ether adduct.

When you are using this chemical, please be cautious about it as the following:
It has risk of serious damage to the eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear eye / face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C1OCCCC1
2. InChI:InChI=1/C5H8O2/c6-5-3-1-2-4-7-5/h1-4H2
3. InChIKey:OZJPLYNZGCXSJM-UHFFFAOYAZ

Product Name

delta-Valerolactone

Synthetic route

delta-Valerolactone Specification

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