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502-49-8 Cyclooctan-1-one
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502-49-8 Usage

Chemical Properties

colorless to white crystalline low melting solid

Uses

Cyclooctanone is a aliphatic cycle that exhibited inhibitory activity towards aldosterone synthase, a promising therapeutic target for the treatment of cardiovascular diseases related to abnormally high aldosterone level.

Purification Methods

Purify the ketone by sublimation after drying with Linde type 13X molecular sieves. The semicarbazone has m 168-169o (from dioxane) [Kohler et al. J Am Chem Soc 61 1060 1939]. The oxime has m 36-37o after subliming at high vacuum or distillation and has b 128-129o /14mm. The iso-oxime has m 72-73o [Ruzicka et al. Helv Chim Acta 32 548 1949]. [Beilstein 7 III 77, 7 IV 49.]
InChI:InChI=1/C8H14O/c9-8-6-4-2-1-3-5-7-8/h1-7H2

502-49-8 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (B20911)  Cyclooctanone, 98%    502-49-8 500g 3380.0CNY Detail
Alfa Aesar (B20911)  Cyclooctanone, 98%    502-49-8 100g 845.0CNY Detail
Alfa Aesar (B20911)  Cyclooctanone, 98%    502-49-8 25g 282.0CNY Detail

502-49-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Cyclooctanone

1.2 Other means of identification

Product number -
Other names CYCLOOCTANONE

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:502-49-8 SDS

502-49-8Synthetic route

cyclooctanol
696-71-9

cyclooctanol

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; sodium tungstate In tert-butyl alcohol at 90℃; for 0.5h;100%
With ruthenium trichloride; iodobenzene; potassium peroxomonosulfate In water; acetonitrile at 20℃; for 0.5h;100%
With ruthenium trichloride; iodobenzene; potassium peroxymonosulfate In water; acetonitrile at 20℃; for 0.5h; Inert atmosphere;100%
Cyclooctan
292-64-8

Cyclooctan

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With hydrogenchloride; FeH6Mo6O24(3-)*3H3N*3H(1+)*7H2O; tetrabutylammomium bromide; dihydrogen peroxide In 1,4-dioxane; water at 85℃; for 24h;98%
With oxygen; isobutyraldehyde; vanadium-substituted V-MCM-41 (A) zeolite In acetone at 25℃; for 24h;83%
With potassium permanganate; borontrifluoride acetic acid In acetonitrile at 23℃; for 0.166667h;55%
Cyclooctene oxide
286-62-4

Cyclooctene oxide

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With lithium iodide In xylene at 140℃; for 6h;98%
With lithium iodide In xylene at 140℃; for 6h; Product distribution; other temperatures, other times; various concentrations of catalyst; other catalyst; without a solvent;
cyclooctylamine
5452-37-9

cyclooctylamine

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With zinc dichromate trihydrate at 20℃; grinding; neat (no solvent); chemoselective reaction;98%
With 3-carboxypyridinium dichromate In acetonitrile at 20℃; for 0.25h;97%
With potassium permanganate; copper(II) sulfate In dichloromethane for 24h; Heating;90%
cyclooctyl methyl ether
13213-32-6

cyclooctyl methyl ether

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
Stage #1: cyclooctyl methyl ether With bromine In dichloromethane; water for 1h; Reflux;
Stage #2: With dihydrogen peroxide In dichloromethane; water for 4h; Reflux;
97%

A

cycloactanone
502-49-8

cycloactanone

B

cyclooctanol
696-71-9

cyclooctanol

Conditions
ConditionsYield
With tetrachloromethane; copper(II) choride dihydrate; chromium(III) acetylacetonate; water at 150℃; for 12h; Sealed tube;A 4%
B 96%
ethyl 2-oxocyclooctane-1-carboxylate
4017-56-5

ethyl 2-oxocyclooctane-1-carboxylate

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With sodio-propane-1,2-diol in anhydrous propane-1,2-diol at 80 - 85℃; for 0.5h;95%
cyclooctanone semicarbazone
40338-24-7

cyclooctanone semicarbazone

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With hydrogenchloride; Tonsil In ethyl acetate for 2h; Heating;94.1%
carbon monoxide
201230-82-2

carbon monoxide

cis-1,2-epoxycyclooctane
4925-71-7

cis-1,2-epoxycyclooctane

A

cycloactanone
502-49-8

cycloactanone

trans-9-oxa-bicyclo[6.2.0]decan-10-one

trans-9-oxa-bicyclo[6.2.0]decan-10-one

Conditions
ConditionsYield
With [(salph)Cr(THF)2][Co(CO)4] In 1,2-dimethoxyethane at 60℃; under 5171.48 Torr; for 24h;A 3%
B 94%
1,1-dimethoxycyclooctane
25632-03-5

1,1-dimethoxycyclooctane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With dimethylboron bromide In dichloromethane; 1,2-dichloro-ethane at -78℃; for 1h;93%
With dimethylboron bromide; sodium hydrogencarbonate 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction;
1,4-dioxaspiro<4.7>dodecane
183-03-9

1,4-dioxaspiro<4.7>dodecane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With dimethylboron bromide In dichloromethane; 1,2-dichloro-ethane at -78℃; for 1h;92%
With Montmorillonite K 10; water In acetone for 0.5h; Heating;87%
indium(III) chloride In methanol; water for 1.5h; Heating;85%
With dimethylboron bromide; sodium hydrogencarbonate 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction;
3,3-dimethyl-1,5-dioxaspiro<5.7>tridecane
27889-58-3

3,3-dimethyl-1,5-dioxaspiro<5.7>tridecane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With dimethylboron bromide In dichloromethane; 1,2-dichloro-ethane at -78℃; for 1h;91%
With dimethylboron bromide; sodium hydrogencarbonate 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction;
2-bromocyclooctan-1-one
39261-18-2

2-bromocyclooctan-1-one

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With diphosphorus tetraiodide In dichloromethane at 25℃; for 7h;91%
(Z)-Cyclooctene
931-88-4, 931-87-3

(Z)-Cyclooctene

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; C21H19N5Pd(2+)*2BF4(1-) In decane; acetonitrile at 70℃; for 24h; Temperature; Wacker Oxidation;90%
With dihydrogen peroxide; tetraphenylphosphonium; sodium hydrogencarbonate; WO(O2)(QO)4 In acetonitrile at 25℃; for 0.5h;74%
Stage #1: cis-Cyclooctene With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
Stage #2: With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide In tetrahydrofuran; dichloromethane at 20℃; Molecular sieve;
53%
1,1-bis(phenylthio)cyclooctane
85895-35-8

1,1-bis(phenylthio)cyclooctane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid In dichloromethane for 1h; Ambient temperature;87%
cis-1,2-epoxycyclooctane
4925-71-7

cis-1,2-epoxycyclooctane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In toluene at 0℃; for 2h;87%
t-BuOSmI2 In tetrahydrofuran at 60℃; for 4h;83%
cyclooctanol
696-71-9

cyclooctanol

Dess-Martin periodane
87413-09-0

Dess-Martin periodane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
In dichloromethane at 25℃; for 2.1h; Product distribution; Mechanism; var. primary and secondary alcohols, var. 12-I-5 species; other solvents and relation time, var. concentrations of oxidant, in the presence of different labile groups in the molecule;86%
(cyclooctyloxy)trimethylsilane
40756-11-4

(cyclooctyloxy)trimethylsilane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With sodium bromate; ammonium chloride In water; acetonitrile at 80℃; for 0.833333h;82%
(Z)-Cyclooctene
931-88-4, 931-87-3

(Z)-Cyclooctene

A

cycloactanone
502-49-8

cycloactanone

B

cis-1,2-epoxycyclooctane
4925-71-7

cis-1,2-epoxycyclooctane

Conditions
ConditionsYield
With oxygen; magnesium oxide supported polytitazane-tin tetrachloride In 1,4-dioxane at 80℃; for 20h;A n/a
B 81%
Cyclooctan
292-64-8

Cyclooctan

A

cycloactanone
502-49-8

cycloactanone

B

cyclooctanol
696-71-9

cyclooctanol

Conditions
ConditionsYield
With CoO40W12(5-)*3C30H24CoN6*9.5H2O*2H(1+); dihydrogen peroxide In acetonitrile at 80℃; for 9h; Inert atmosphere;A 80%
B 19%
With [Fe4III(μ-O)2(μ-acetate)6(2,2'-bipyridine)2(H2O)2](NO3-)(OH-); dihydrogen peroxide; acetic acid In water; acetonitrile at 32℃; for 3h; Catalytic behavior; Overall yield = 89 %Spectr.;A 77%
B 13%
With oxygen; copper diacetate; acetaldehyde In dichloromethane; acetonitrile at 70℃; under 760.051 Torr; for 24h; Catalytic behavior; Inert atmosphere;A 74%
B 8%
1,2-dicyclooctylidenehydrazine
53867-57-5

1,2-dicyclooctylidenehydrazine

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With HOF* CH3CN In dichloromethane at 0℃; for 0.0166667h;80%
{[Cp*Ru(CO)2]2(μ-H)}+OTf-

{[Cp*Ru(CO)2]2(μ-H)}+OTf-

cyclooctanol
696-71-9

cyclooctanol

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With hydrogen In 1,2-dichloro-benzene80%
Cyclooctan
292-64-8

Cyclooctan

A

cycloactanone
502-49-8

cycloactanone

B

cyclooctylhydroperoxide
5130-47-2

cyclooctylhydroperoxide

Conditions
ConditionsYield
With HO40PVW11(14-)*4C16H36N(1+); dihydrogen peroxide In acetonitrile at 80℃; for 12h; Inert atmosphere;A 23%
B 77%
With 5,10,15,20-tetrakis(4-chlorophenyl)porphyrinatocopper(II); T(o-Cl)PPCo; oxygen at 110℃; under 10501.1 Torr; for 8h;
cyclooctanone thioketal
183-04-0

cyclooctanone thioketal

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With formaldehyd; water; acetone; Amberlyst 15 at 80℃; for 10h;76%
(+/-)-trans-2-bromo-1-hydroxycyclooctane
1502-14-3, 74305-06-9, 84402-56-2

(+/-)-trans-2-bromo-1-hydroxycyclooctane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Ambient temperature; Irradiation;76%
With di-tert-butyl diperoxyoxalate In cyclohexane Heating;93 % Chromat.
Dichloromethyl methyl ether
4885-02-3

Dichloromethyl methyl ether

B-methoxyborocane
60579-50-2

B-methoxyborocane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
74%
In not given IR, PMR, mass spectral data, GLC;;74%
(Pyrrolidinylmethylene)cyclooctane
76902-54-0

(Pyrrolidinylmethylene)cyclooctane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With potassium dichromate; sulfuric acid In diethyl ether at 25℃; for 1h;73%
Cyclooctene oxide
286-62-4

Cyclooctene oxide

A

cycloactanone
502-49-8

cycloactanone

B

cycloheptanecarboxaldehyde
4277-29-6

cycloheptanecarboxaldehyde

Conditions
ConditionsYield
at 600℃;A 71%
B 14%
With aluminum oxide; lithium bromide at 180℃; for 0.5h; Yield given. Yields of byproduct given;
(E)-1-trimethylsilyloxy-1-cyclooctene
50338-42-6

(E)-1-trimethylsilyloxy-1-cyclooctene

A

cycloactanone
502-49-8

cycloactanone

B

2-hydroxycylooctanone
496-82-2

2-hydroxycylooctanone

Conditions
ConditionsYield
With tris(cetylpyridinium) 12-tungstophosphate; dihydrogen peroxide In dichloromethane for 6h; Heating;A 14%
B 71%
With tris(cetylpyridinium) 12-tungstophosphate; dihydrogen peroxide In dichloromethane at 20℃; for 16h; oxidative cleavage;A 20 % Chromat.
B 45 % Chromat.
cycloactanone
502-49-8

cycloactanone

cyclooctanone oxime
1074-51-7

cyclooctanone oxime

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In ethanol at 90 - 100℃; for 2h;100%
With ammonium chloride; Amberlyst A-21 In ethanol for 1h; Ambient temperature;95%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux;90%
cycloactanone
502-49-8

cycloactanone

cyclooctanol
696-71-9

cyclooctanol

Conditions
ConditionsYield
With aluminum oxide; sodium tetrahydroborate In hexane at 30℃; for 3h;100%
With hydrogen In ethanol at 130℃; under 30003 Torr; for 20h; Autoclave;97%
With chloro-trimethyl-silane; calcium hydride; zinc(II) chloride In tetrahydrofuran at 40℃; for 0.5h;92%
cycloactanone
502-49-8

cycloactanone

2-chlorocyclooctanone
4828-34-6

2-chlorocyclooctanone

Conditions
ConditionsYield
Stage #1: cycloactanone With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: With methyl chlorosulfate In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
100%
With ammonium cerium(IV) nitrate at 25 - 28℃; for 5.5h;86%
With p-toluenesulfonyl chloride; lithium diisopropyl amide In tetrahydrofuran -78 deg C to room t., 1 h;69%
cycloactanone
502-49-8

cycloactanone

methyl iodide
74-88-4

methyl iodide

2-methylcyclooctanone
10363-27-6

2-methylcyclooctanone

Conditions
ConditionsYield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 20℃;100%
Stage #1: cycloactanone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at -78℃; for 0.666667h;
62%
With sodium amide
With lithium diisopropyl amide 1.) THF, -78 deg C, 30 min, 2.) THF, RT, 40 h; Yield given. Multistep reaction;
Stage #1: cycloactanone With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; Further stages.;
cycloactanone
502-49-8

cycloactanone

1-chloroethyl p-tolyl sulfoxide
50635-71-7, 50635-72-8, 31350-93-3

1-chloroethyl p-tolyl sulfoxide

1-<1-chloro-1-(p-tolylsulfinyl)ethyl>-1-cyclooctanol
159763-14-1

1-<1-chloro-1-(p-tolylsulfinyl)ethyl>-1-cyclooctanol

Conditions
ConditionsYield
at -70℃;100%
With n-butyllithium; diisopropylamine In tetrahydrofuran at -65℃; for 0.416667h;37%
cycloactanone
502-49-8

cycloactanone

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

cyclooctanone p-tolylsulfonylhydrazone
2567-85-3

cyclooctanone p-tolylsulfonylhydrazone

Conditions
ConditionsYield
In ethanol at 100℃; for 1h;100%
In ethanol at 100℃; for 1.66667h; Inert atmosphere;100%
In methanol at 20℃; Schlenk technique;100%
cycloactanone
502-49-8

cycloactanone

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

methyl 2-oxocyclooctanecarboxylate
5452-73-3

methyl 2-oxocyclooctanecarboxylate

Conditions
ConditionsYield
With sodium hydride In 1,4-dioxane at 90℃; Reflux;100%
Stage #1: carbonic acid dimethyl ester With sodium hydride In tetrahydrofuran at 5 - 10℃; for 0.5h; Inert atmosphere;
Stage #2: cycloactanone In tetrahydrofuran for 4.5h; Reflux; Inert atmosphere;
88%
Stage #1: carbonic acid dimethyl ester With sodium hydride In tetrahydrofuran at 5 - 10℃; for 0.5h;
Stage #2: cycloactanone In tetrahydrofuran for 4.5h; Reflux;
88%
cycloactanone
502-49-8

cycloactanone

acrolein
107-02-8

acrolein

2-(2-propen-1-ol)cyclooctanone
916853-97-9

2-(2-propen-1-ol)cyclooctanone

Conditions
ConditionsYield
Stage #1: cycloactanone With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 0℃;
Stage #2: acrolein In tetrahydrofuran; hexane at -78℃; Further stages.;
100%
98%
Stage #1: cycloactanone With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 0℃; for 1h;
Stage #2: acrolein In tetrahydrofuran; hexane at -78℃; for 0.0166667h;
Stage #1: cycloactanone With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.75h;
Stage #2: acrolein In tetrahydrofuran; hexane at -78℃;
cycloactanone
502-49-8

cycloactanone

Bromoform
75-25-2

Bromoform

1-(Tribromomethyl)cyclooctan-1-ol
258504-47-1

1-(Tribromomethyl)cyclooctan-1-ol

Conditions
ConditionsYield
Stage #1: Bromoform With lithium diisopropyl amide In tetrahydrofuran; hexane at -100℃; for 0.166667h; Metallation;
Stage #2: cycloactanone With boron trifluoride diethyl etherate In tetrahydrofuran; diethyl ether; hexane at -90℃; for 4h; Addition;
100%
cycloactanone
502-49-8

cycloactanone

t-butoxycarbonylhydrazine
870-46-2

t-butoxycarbonylhydrazine

N'-cyclooctylidene-hydrazinecarboxylic acid tert-butyl ester
339058-79-6

N'-cyclooctylidene-hydrazinecarboxylic acid tert-butyl ester

Conditions
ConditionsYield
In methanol at 20℃;100%
cycloactanone
502-49-8

cycloactanone

3-amino-4-cyano-5-methylsulfanyl-1H-pyrrole-2-carboxylic acid ethyl ester
124476-10-4

3-amino-4-cyano-5-methylsulfanyl-1H-pyrrole-2-carboxylic acid ethyl ester

8-amino-6-methylsulfanyl-2,5-diaza-tricylo[7.6.0.03,7]-pentadeca-1,3,6,8-tetraene-4-carboxylic acid ethyl ester

8-amino-6-methylsulfanyl-2,5-diaza-tricylo[7.6.0.03,7]-pentadeca-1,3,6,8-tetraene-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
With aluminium trichloride In 1,2-dichloro-ethane at 115 - 120℃; for 2h; Friedlaender cyclization reaction;100%
cycloactanone
502-49-8

cycloactanone

C32H60BO4(1-)*Na(1+)

C32H60BO4(1-)*Na(1+)

Conditions
ConditionsYield
With sodium tetrahydroborate at 60℃; for 0.5h; Ball milling; neat (no solvent); regiospecific reaction;100%
cycloactanone
502-49-8

cycloactanone

5-fluorouridine
316-46-1

5-fluorouridine

5-fluoro-1-[(3a'R,4'R,6'R,6a'R)-3a',4',6',6a'-tetrahydro-6'-(hydroxymethyl)spiro[cyclooctane-1,2'-furo[3,4-d][1,3]dioxol]-4'-yl]pyrimidine-2,4(1H,3H)-dione

5-fluoro-1-[(3a'R,4'R,6'R,6a'R)-3a',4',6',6a'-tetrahydro-6'-(hydroxymethyl)spiro[cyclooctane-1,2'-furo[3,4-d][1,3]dioxol]-4'-yl]pyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 4h;100%
cycloactanone
502-49-8

cycloactanone

3-(4-fluorophenyl)-3-oxopropionitrile
4640-67-9

3-(4-fluorophenyl)-3-oxopropionitrile

4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocyclooctane[b]pyridine-(1H)-ketone
132812-72-7

4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocyclooctane[b]pyridine-(1H)-ketone

Conditions
ConditionsYield
With 1-ethyl-3-methylimidazolium tetrafluoroborate at 120℃; for 1h;99.8%
With methanesulfonic acid; phosphorus pentoxide at 50℃; for 15h;95%
With PPA Heating;64%
With phosphoric acid; toluene-4-sulfonic acid In toluene Reflux; Dean-Stark; Large scale;54%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

cycloactanone
502-49-8

cycloactanone

(cyclooct-1-enyloxy)-trimethylsilane
50338-42-6

(cyclooct-1-enyloxy)-trimethylsilane

Conditions
ConditionsYield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; Inert atmosphere;99%
With triethylamine In N,N-dimethyl-formamide for 15h; Reflux;93%
With triethylamine In N,N-dimethyl-formamide
cycloactanone
502-49-8

cycloactanone

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

1-((trimethylsilyl)oxy)cyclooctanecarbonitrile
50361-50-7

1-((trimethylsilyl)oxy)cyclooctanecarbonitrile

Conditions
ConditionsYield
With C29H46LaN3Si2 at 15℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique;99%
With n-butyllithium In tetrahydrofuran; hexane for 2h; Ambient temperature;96.7%
potassium-exchanged zirconium hydrogen phosphate In dichloromethane for 20h; Heating;95%
cycloactanone
502-49-8

cycloactanone

N,N-dimethyl(methylene)ammonium chloride
30354-18-8

N,N-dimethyl(methylene)ammonium chloride

2-(Dimethylamino)methylcyclooctan-1-one
28118-62-9

2-(Dimethylamino)methylcyclooctan-1-one

Conditions
ConditionsYield
In acetonitrile for 72h; Ambient temperature;99%
cycloactanone
502-49-8

cycloactanone

potassium terbutylate

potassium terbutylate

cycloheptanone
502-42-1

cycloheptanone

A

α-(α'-cycloheptenyl)-β-hydroxycarbonyl-ethyl propionate
187819-58-5

α-(α'-cycloheptenyl)-β-hydroxycarbonyl-ethyl propionate

B

2,4,5,6,7,8-hexahydroazulene
32405-96-2

2,4,5,6,7,8-hexahydroazulene

Conditions
ConditionsYield
With hydrogenchloride In water; N,N-dimethyl-formamideA 99%
B n/a
cycloactanone
502-49-8

cycloactanone

1-((trimethylsilyl)oxy)cyclooctanecarbonitrile
50361-50-7

1-((trimethylsilyl)oxy)cyclooctanecarbonitrile

Conditions
ConditionsYield
n-butyllithium In tetrahydrofuran99%
potassium cyanide

potassium cyanide

cycloactanone
502-49-8

cycloactanone

1,3-diazaspiro[4.7]dodecane-2,4-dione
710-94-1

1,3-diazaspiro[4.7]dodecane-2,4-dione

Conditions
ConditionsYield
Stage #1: potassium cyanide; cycloactanone In ethanol; water at 60℃; for 11h; Inert atmosphere;
Stage #2: With hydrogenchloride In ethanol; water at 0℃; for 15h;
99%
With ammonium carbonate In methanol; water at 140℃; for 0.133333h; Sealed vial; Microwave irradiation;85%
cycloactanone
502-49-8

cycloactanone

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-((trimethylsilyl)ethynyl)cyclooctanol
1403824-58-7

1-((trimethylsilyl)ethynyl)cyclooctanol

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: cycloactanone In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
99%
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: cycloactanone In tetrahydrofuran; hexane at 0 - 25℃; for 2h; Inert atmosphere;
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: cycloactanone In tetrahydrofuran; hexane at 20℃; for 2h;
cycloactanone
502-49-8

cycloactanone

octane-1,8-dioic acid
505-48-6

octane-1,8-dioic acid

Conditions
ConditionsYield
With oxygen; trifluoroacetic acid; sodium nitrite at 0 - 20℃; for 5.25h; Product distribution / selectivity;98%
With dihydrogen peroxide In water; acetonitrile at 90℃; for 11h; Green chemistry;92%
With dihydrogen peroxide; ortho-tungstic acid In water at 90℃; for 20h;85%
cycloactanone
502-49-8

cycloactanone

cyclooctane-1,2-dione
3008-37-5

cyclooctane-1,2-dione

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In tetrahydrofuran at 20℃; for 0.2h;98%
With perchloric acid; tripropylammonium fluorochromate (VI) In water; acetic acid at 24.9℃; Rate constant; Thermodynamic data; ΔH(activ.), ΔS(activ.), ΔG(activ.); further temperatures (308-328 K);
With selenium(IV) oxide In ethanol
furan
110-00-9

furan

cycloactanone
502-49-8

cycloactanone

1-(furan-2-yl)cyclooctanol
115754-91-1

1-(furan-2-yl)cyclooctanol

Conditions
ConditionsYield
Stage #1: furan With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexanes at -78℃; for 1h; Inert atmosphere;
Stage #2: cycloactanone In tetrahydrofuran; hexanes at -78℃; for 1h; Inert atmosphere;
Stage #3: With ammonium chloride In tetrahydrofuran; hexanes; water
98%
With n-butyllithium; toluene-4-sulfonic acid Multistep reaction;
Stage #1: furan With n-butyllithium In diethyl ether; hexane at 0℃;
Stage #2: cycloactanone In diethyl ether; hexane at 0 - 20℃;
cycloactanone
502-49-8

cycloactanone

trimethylsulfoxonium bromide

trimethylsulfoxonium bromide

1-oxaspiro[2,7]-decane
185-88-6

1-oxaspiro[2,7]-decane

Conditions
ConditionsYield
With potassium hydroxide In water; acetonitrile at 60℃; for 3h;98%
cycloactanone
502-49-8

cycloactanone

formic acid ethyl ester
109-94-4

formic acid ethyl ester

2-hydroxymethylenecyclooctan-1-one sodium salt

2-hydroxymethylenecyclooctan-1-one sodium salt

Conditions
ConditionsYield
With ethanol; sodium In diethyl ether98%
With ethanol; sodium In diethyl ether at 20℃; for 48h; Inert atmosphere;

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