Product Name

  • Name

    2,2-DIMETHYLCYCLOPENTANONE

  • EINECS
  • CAS No. 4541-32-6
  • Article Data48
  • CAS DataBase
  • Density 0.9±0.1 g/cm3
  • Solubility
  • Melting Point
  • Formula C7H12O
  • Boiling Point 148.1±8.0 °C at 760 mmHg
  • Molecular Weight 112.172
  • Flash Point 32.778 °C
  • Transport Information UN 1224 3/PG 3
  • Appearance clear colorless to yellow liquid
  • Safety 16-29-33
  • Risk Codes 10
  • Molecular Structure Molecular Structure of 4541-32-6 (2,2-DIMETHYLCYCLOPENTANONE)
  • Hazard Symbols
  • Synonyms 2,2-Dimethyl-1-cyclopentanone;
  • PSA 17.07000
  • LogP 1.76560

Synthetic route

1-(trimethylsilyloxy)cyclopentene
19980-43-9

1-(trimethylsilyloxy)cyclopentene

methyl iodide
74-88-4

methyl iodide

A

2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

B

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

C

cis-2,5-dimethylcyclopentanone
6672-39-5

cis-2,5-dimethylcyclopentanone

(+/-)-trans-2,5-dimethylcyclopentanone
83664-37-3

(+/-)-trans-2,5-dimethylcyclopentanone

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; methyllithium; dimethyl zinc(II) In tetrahydrofuran at -78℃; for 10h;A 98%
B n/a
C n/a
D n/a
With methyllithium In tetrahydrofuran at 0℃; for 3h; Further byproducts given;A 79%
B n/a
C n/a
D n/a
5,5-dimethylcyclopent-2-enone
17197-84-1

5,5-dimethylcyclopent-2-enone

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol for 6h; Ambient temperature;96%
With lithium tri(t-butoxy)aluminum hydride In tetrahydrofuran at -78℃; for 2h;66%
1-(2-hydroxyprop-2-yl)cyclobutanol
99767-31-4

1-(2-hydroxyprop-2-yl)cyclobutanol

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Rearrangement;93%
2-bromomethyl-2-methylcyclopentanone

2-bromomethyl-2-methylcyclopentanone

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With acetic acid; zinc at 110℃; for 2h;92%
5-iodo-2,2-dimethylpentanenitrile
56475-44-6

5-iodo-2,2-dimethylpentanenitrile

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
Stage #1: 5-iodo-2,2-dimethylpentanenitrile With n-hexyllithium In tetrahydrofuran; hexane at -20 - -5℃; for 1.33333h;
Stage #2: With oxalic acid In tetrahydrofuran; hexane; water at -5 - 20℃;
81%
With magnesium; ethylene dibromide In diethyl ether
1-(trimethylsilyloxy)cyclopentene
19980-43-9

1-(trimethylsilyloxy)cyclopentene

methyl iodide
74-88-4

methyl iodide

A

2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

B

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

C

2,2,5-trimethylcyclopentanone
4573-09-5

2,2,5-trimethylcyclopentanone

D

cis-2,5-dimethylcyclopentanone
6672-39-5

cis-2,5-dimethylcyclopentanone

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran at 0℃; for 3h; Further byproducts given;A 79%
B n/a
C n/a
D n/a
With methyllithium 1.) THF, 2.) 0 deg C, 3 h; Multistep reaction. Further byproducts given. Yields of byproduct given;
1-(trimethylsilyloxy)cyclopentene
19980-43-9

1-(trimethylsilyloxy)cyclopentene

methyl iodide
74-88-4

methyl iodide

A

2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

B

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

C

2,2,5-trimethylcyclopentanone
4573-09-5

2,2,5-trimethylcyclopentanone

D

cis-2,5-dimethylcyclopentanone
6672-39-5

cis-2,5-dimethylcyclopentanone

(+/-)-trans-2,5-dimethylcyclopentanone
83664-37-3

(+/-)-trans-2,5-dimethylcyclopentanone

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran at 0℃; for 3h; Product distribution; var. temp., times, and reagent systems; other lithium enolates;A 79%
B n/a
C n/a
D n/a
E n/a
trans-1,2-dimethylcyclopentan-1,2-diol
6296-92-0, 33046-19-4, 33046-20-7

trans-1,2-dimethylcyclopentan-1,2-diol

1-(2-hydroxyprop-2-yl)cyclobutanol
99767-31-4

1-(2-hydroxyprop-2-yl)cyclobutanol

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With phosphoric acid; phosphorus pentoxide at 45℃; for 0.166667h; Rearrangement;66%
1-(1-Methyl-1-methylselanyl-ethyl)-cyclobutanol
112126-07-5

1-(1-Methyl-1-methylselanyl-ethyl)-cyclobutanol

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With potassium hydroxide; chloroform; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 20℃; for 1h;63%
2,2-dimethyl-adipic acid-anhydride

2,2-dimethyl-adipic acid-anhydride

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
bei langsamer Destillation;
2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With diethyl ether; sodium amide anschliessend Behandeln mit Methyljodid, zuletzt auf dem Dampfbad;
2,2-dimethyladipic acid
763-06-4

2,2-dimethyladipic acid

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With thorium hydroxide at 280 - 290℃;
With barium dihydroxide at 285℃;
cis-1,2-dimethyl-1,2-cyclopentanediol
33046-19-4

cis-1,2-dimethyl-1,2-cyclopentanediol

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With sulfuric acid
With D3+; oxygen; trimethylamine at 37.5℃; Product distribution; Irradiation; trans compound and various conditions investigated;
rac-2,2-dimethylcyclopentanol
37617-33-7

rac-2,2-dimethylcyclopentanol

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With potassium permanganate at 20℃; Erwaermen des Reaktionsprodukts auf 50grad;
With chromium(VI) oxide; sulfuric acid In acetone
cyclopentanone
120-92-3

cyclopentanone

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With sodium tert-pentoxide; dimethyl sulfate
In carbonic acid dimethyl ester
2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

methyl iodide
74-88-4

methyl iodide

A

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

B

2,5-dimethylcyclopentanone
4041-09-2

2,5-dimethylcyclopentanone

Conditions
ConditionsYield
With sodium amide
3-methylcyclohexen-2-one
1193-18-6

3-methylcyclohexen-2-one

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With hydrogenchloride; mercury; zinc
With titanium tetrachloride; lithium trimethylstannyl 1.) THF, 0 deg C, 15 min, 2.) CH2Cl2, -78 deg C, 15 min; Yield given. Multistep reaction;
2,2-dimethylhexanedinitrile
2941-44-8

2,2-dimethylhexanedinitrile

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
(i) NaNH2, Et2O, (ii) H2SO4, AcOH; Multistep reaction;
cyclopentanone
120-92-3

cyclopentanone

dimethyl sulfate
77-78-1

dimethyl sulfate

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With sodium tert-pentoxide In diethyl ether; benzene
With sodium tert-pentoxide In toluene at 20 - 35℃; for 28h;5.2 g
2-<(n-butylthio)methylene>cyclopentanone
32116-72-6

2-<(n-butylthio)methylene>cyclopentanone

methyl iodide
74-88-4

methyl iodide

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
(i) Li, liq. NH3, H2O, Et2O, (ii) /BRN= 969135/; Multistep reaction;
2,2-dimethyl-4-pentenal
5497-67-6

2,2-dimethyl-4-pentenal

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
(PPh3)2Co(dppe) In acetonitrile; benzene at 70℃; for 3h; Yield given;
2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

methyl iodide
74-88-4

methyl iodide

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With n-butyllithium; diisopropylamine 1.) hexane, THF, -78 deg C, 0.5 h, then 0 deg C, 3 h 2.) 3 h; Yield given. Multistep reaction;
2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

methyl iodide
74-88-4

methyl iodide

A

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

B

2,5-dimethylcyclopentanone
4041-09-2

2,5-dimethylcyclopentanone

C

2,2,5-trimethylcyclopentanone
4573-09-5

2,2,5-trimethylcyclopentanone

D

2,2,5,5-tetramethylcyclopentanone
4541-35-9

2,2,5,5-tetramethylcyclopentanone

Conditions
ConditionsYield
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

methyl iodide
74-88-4

methyl iodide

A

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

B

2,5-dimethylcyclopentanone
4041-09-2

2,5-dimethylcyclopentanone

C

2,4-dimethylcyclopentanone
1121-33-1, 6672-40-8

2,4-dimethylcyclopentanone

Conditions
ConditionsYield
With (2-pyrr)2Mg electrogenerated base In N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane at -50℃; for 1.5h; Product distribution; other temperatures, time, recyclization;
2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

sodium amide

sodium amide

methyl iodide
74-88-4

methyl iodide

A

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

B

2,5-dimethylcyclopentanone
4041-09-2

2,5-dimethylcyclopentanone

α.α-dimethyl-adipic acid

α.α-dimethyl-adipic acid

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With acetic anhydride
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

6,6-dimethyltetrahydro-2H-pyran-2-one
2610-95-9

6,6-dimethyltetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With potassium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane; water for 5h; Baeyer-Villiger Ketone Oxidation; Reflux;100%
With trifluoroacetyl peroxide at 0℃;99%
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 18h; Baeyer-Villiger Ketone Oxidation;77%
With dihydrogen peroxide; trifluoroacetic anhydride at 20℃; Baeyer-Villiger oxidation;67%
With Mg10Al2(OH)24CO3; oxygen; benzaldehyde In 1,2-dichloro-ethane at 40℃; for 24h;61%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

(R)-1-phenyl-ethyl-amine
3886-69-9

(R)-1-phenyl-ethyl-amine

(R,E)-N-(2,2-dimethylcyclopentylidene)-1-phenylethanamine
167321-13-3

(R,E)-N-(2,2-dimethylcyclopentylidene)-1-phenylethanamine

Conditions
ConditionsYield
With titanium tetrachloride; triethylamine In dichloromethane at 20℃; for 16h; Cooling with ice;100%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

2-(aminooxy)-2-methylpropanoic acid hydrochloride

2-(aminooxy)-2-methylpropanoic acid hydrochloride

2-(((2,2-dimethylcyclopentylidene)amino)oxy)-2-methylpropanoic acid

2-(((2,2-dimethylcyclopentylidene)amino)oxy)-2-methylpropanoic acid

Conditions
ConditionsYield
With sodium acetate In methanol Reflux;100%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

ketene t-butyldimethylsilyl methyl acetal
77086-38-5

ketene t-butyldimethylsilyl methyl acetal

methyl 2-(1-((tert-butyldimethylsilyl)oxy)-2,2-dimethylcyclopentyl)acetate

methyl 2-(1-((tert-butyldimethylsilyl)oxy)-2,2-dimethylcyclopentyl)acetate

Conditions
ConditionsYield
Stage #1: 2,2-dimethylcyclopentanone With bis(trifluoromethanesulfonyl)amide In diethyl ether at -78 - 23℃; Mukaiyama Aldol Addition; Schlenk technique; Inert atmosphere;
Stage #2: ketene t-butyldimethylsilyl methyl acetal In diethyl ether at -20℃; for 0.5h; Mukaiyama Aldol Addition; Schlenk technique; Inert atmosphere;
98%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

5-((dimethylamino)methylene)-2,2-dimethylcyclopentanone

5-((dimethylamino)methylene)-2,2-dimethylcyclopentanone

Conditions
ConditionsYield
In toluene at 100℃; for 22h;97%
In toluene at 100℃; for 22h; Temperature;97%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

2,2-Dimethyl-1-trimethylsilanyloxy-cyclopentanecarbonitrile
586398-08-5

2,2-Dimethyl-1-trimethylsilanyloxy-cyclopentanecarbonitrile

Conditions
ConditionsYield
With zinc(II) iodide In benzene for 7.5h; Ambient temperature;95%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

tert-Butoxybis(dimethylamino)methane
5815-08-7

tert-Butoxybis(dimethylamino)methane

5-((dimethylamino)methylene)-2,2-dimethylcyclopentanone

5-((dimethylamino)methylene)-2,2-dimethylcyclopentanone

Conditions
ConditionsYield
at 20 - 110℃; for 2.75h; Inert atmosphere;95%
at 110℃; for 1h; Inert atmosphere;94%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

2-Trifluoromethylbenzaldehyde
447-61-0

2-Trifluoromethylbenzaldehyde

5-[1-(2-trifluoromethylphenyl)-meth-(E)-ylidene]-2,2-dimethylcyclopentanone
1253105-70-2

5-[1-(2-trifluoromethylphenyl)-meth-(E)-ylidene]-2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 0 - 20℃;94%
N,N-phenylbistrifluoromethane-sulfonimide
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

5,5-dimethylcyclopent-1-en-1-yl trifluoromethanesulfonate
153580-03-1

5,5-dimethylcyclopent-1-en-1-yl trifluoromethanesulfonate

Conditions
ConditionsYield
Stage #1: 2,2-dimethylcyclopentanone With lithium diisopropyl amide In tetrahydrofuran; n-heptane at -78℃; for 1h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78℃; for 1h;
92%
Stage #1: 2,2-dimethylcyclopentanone With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.75h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran; hexane at -78 - 20℃; for 3h;
50%
Stage #1: 2,2-dimethylcyclopentanone With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 3h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78℃; for 1h;
28%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2-chloro-3,3-dimethylcyclopent-1-ene-1-carbaldehyde

2-chloro-3,3-dimethylcyclopent-1-ene-1-carbaldehyde

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: 2,2-dimethylcyclopentanone In dichloromethane at 20 - 40℃; for 17h; Inert atmosphere;
91.93%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

malononitrile
109-77-3

malononitrile

cyano (2,2-dimethylcyclopentylidene) acetonitrile
303156-60-7

cyano (2,2-dimethylcyclopentylidene) acetonitrile

Conditions
ConditionsYield
With ammonium acetate; acetic acid In toluene Heating / reflux;91%
With piperidine; benzoic acid In benzene for 100h; Condensation; Heating;61%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

ethyl 2-(3,3-dimethyl-2-oxo-cyclopentyl)-2-oxo-acetate
856256-48-9

ethyl 2-(3,3-dimethyl-2-oxo-cyclopentyl)-2-oxo-acetate

Conditions
ConditionsYield
Stage #1: 2,2-dimethylcyclopentanone; oxalic acid diethyl ester With ethanol; sodium ethanolate; sodium hydride at 0 - 20℃; for 6.25h;
Stage #2: With hydrogenchloride In ethanol; water at 0℃;
90%
With sodium ethanolate
In ethanol
With sodium ethanolate In ethanol at -15 - 20℃; Inert atmosphere;8.2 g
With sodium ethanolate In ethanol at -15 - 20℃; Inert atmosphere;8.2 g
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

1-(2-hydroxy-1-((4-methoxybenzyl)oxy)propan-2-yl)cyclopropane-1-carbaldehyde

1-(2-hydroxy-1-((4-methoxybenzyl)oxy)propan-2-yl)cyclopropane-1-carbaldehyde

(E)-5-((1-(2-hydroxy-1-((4-methoxybenzyl)oxy)propan-2-yl)cyclopropyl)methylene)-2,2-dimethylcyclopentan-1-one

(E)-5-((1-(2-hydroxy-1-((4-methoxybenzyl)oxy)propan-2-yl)cyclopropyl)methylene)-2,2-dimethylcyclopentan-1-one

Conditions
ConditionsYield
Stage #1: 2,2-dimethylcyclopentanone With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; pentane at 0℃; for 0.25h; Aldol Condensation; Inert atmosphere;
Stage #2: 1-(2-hydroxy-1-((4-methoxybenzyl)oxy)propan-2-yl)cyclopropane-1-carbaldehyde In tetrahydrofuran; N,N-dimethyl-formamide; pentane at 0℃; for 0.25h; Inert atmosphere;
90%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

2,4-difluorobenzaldehyde
1550-35-2

2,4-difluorobenzaldehyde

5-[1-(2,4-difluorophenyl)-meth-(E)-ylidene]-2,2-dimethylcyclopentanone
1253245-30-5

5-[1-(2,4-difluorophenyl)-meth-(E)-ylidene]-2,2-dimethylcyclopentanone

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 0 - 20℃;88%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

Diethyl carbonate
105-58-8

Diethyl carbonate

ethyl 3,3-dimethyl-2-oxocyclopentane-1-carboxylate

ethyl 3,3-dimethyl-2-oxocyclopentane-1-carboxylate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil for 24h; Reflux;88%
With sodium hydride
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

allyl alcohol
107-18-6

allyl alcohol

C13H20O

C13H20O

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel (0) In methanol at 80℃; for 18h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;87%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

rac-2,2-dimethylcyclopentanol
37617-33-7

rac-2,2-dimethylcyclopentanol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 20℃; for 3h;86%
With borane-THF; L-proline In tetrahydrofuran for 0.166667h; Reduction;78%
With sodium tetrahydroborate In isopropyl alcohol at 25℃; for 20h; Kinetics;
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

2-Iodobenzyl bromide
40400-13-3

2-Iodobenzyl bromide

5-(2-iodobenzyl)-2,2-dimethylcyclopentanone

5-(2-iodobenzyl)-2,2-dimethylcyclopentanone

Conditions
ConditionsYield
Stage #1: 2,2-dimethylcyclopentanone With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Schlenk technique; Inert atmosphere;
Stage #2: 2-Iodobenzyl bromide In tetrahydrofuran; hexane at -78 - 0℃; for 1.5h; Schlenk technique; Inert atmosphere;
85%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

benzaldehyde
100-52-7

benzaldehyde

(E)-2-benzylidene-5,5-dimethylcyclopentanone
146513-79-3

(E)-2-benzylidene-5,5-dimethylcyclopentanone

Conditions
ConditionsYield
With sodium methylate In methanol for 16h; Ambient temperature;84%
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

C11H18O2

C11H18O2

Conditions
ConditionsYield
Stage #1: 2,3-dihydro-2H-furan With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - 0℃; for 1h;
Stage #2: 2,2-dimethylcyclopentanone In tetrahydrofuran; pentane at -78 - 20℃; for 6h;
Stage #3: With Dowex-50X In dichloromethane at 20℃; for 24h; Further stages.;
81%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

(R)-2,2-dimethylcyclopentan-1-ol
109530-56-5

(R)-2,2-dimethylcyclopentan-1-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran for 1h; in air;80%
Stage #1: 2,2-dimethylcyclopentanone With (4R,5R)-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylic acid In tetrahydrofuran for 0.25h; Cooling with ice;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran for 2h; optical yield given as %ee;
80%
With (+)-diiso-2-ethylapophosphate pinacylboraneheptane In ethyl acetate at -25℃; for 24h;68%
With diisopinocamphenylchloroborane Yield given;
With Octanethiol; 2,4-dinitrobenzenesulfonic acid; (2S,4S)-pentane-2,4-diol In benzene for 1.5h; Reflux; optical yield given as %ee;36 %Spectr.
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

methyl 3,3-dimethyl-2-oxocyclopentyl-1-carboxylate
80969-68-2

methyl 3,3-dimethyl-2-oxocyclopentyl-1-carboxylate

Conditions
ConditionsYield
With sodium hydride In methanol at 82℃; for 5h;79.5%
2,2-dimethylcyclopentanone
4541-32-6

2,2-dimethylcyclopentanone

phenoxyamine hydrochloride
6092-80-4

phenoxyamine hydrochloride

2,2-dimethylcyclopentan-1-one O-phenyl oxime

2,2-dimethylcyclopentan-1-one O-phenyl oxime

Conditions
ConditionsYield
With pyridine at 20℃; for 18h; Inert atmosphere;79%

2,2-Dimethylcyclopentanone Specification

The 2,2-Dimethylcyclopentanone, with the CAS registry number 4541-32-6, is also known as Cyclopentanone, 2,2-dimethyl-. It belongs to the product categories of C7 to C8; Carbonyl Compounds; Ketones. This chemical's molecular formula is C7H12O and formula weight is 112.17. What's more, its IUPAC name is called 2,2-dimethylcyclopentan-1-one. This chemical is clear colorless to yellow liquid.

Physical properties of 2,2-Dimethylcyclopentanone: (1)ACD/LogP: 1.23; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.23; (4)ACD/LogD (pH 7.4): 1.23; (5)ACD/BCF (pH 5.5): 5.07; (6)ACD/BCF (pH 7.4): 5.07; (7)ACD/KOC (pH 5.5): 111.31; (8)ACD/KOC (pH 7.4): 111.31; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.438; (13)Molar Refractivity: 32.51 cm3; (14)Molar Volume: 123.6 cm3; (15)Surface Tension: 27.1 dyne/cm; (16)Density: 0.907 g/cm3; (17)Flash Point: 32.8 °C; (18)Enthalpy of Vaporization: 38.51 kJ/mol; (19)Boiling Point: 148.1 °C at 760 mmHg; (20)Vapour Pressure: 4.29 mmHg at 25°C.

Preparation: this chemical can be prepared by 5,5-dimethyl-cyclopent-2-enone. This reaction will need reagent lithium tri-t-butoxyaluminium hydride and solvent tetrahydrofuran. The reaction time is 2 hours with reaction temperature of -78 ℃. The yield is about 66%.

Uses of 2,2-Dimethylcyclopentanone: it can be used to produce 5,5-dimethyl-1-morpholinocyclopentene. This reaction will need reagent p-toluenesulfonic acid and solvent toluene with reaction time of 36 hours. The yield is about 75%.

When you are using this chemical, please be cautious about it as the following:
This chemical is flammable. You should keep it away from sources of ignition - No smoking. In addition, please do not empty into drains. Besides, you should take precautionary measures against static discharges.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1(CCCC1=O)C
(2)InChI: InChI=1S/C7H12O/c1-7(2)5-3-4-6(7)8/h3-5H2,1-2H3
(3)InChIKey: FTGZMZBYOHMEPS-UHFFFAOYSA-N

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