Product Name

  • Name

    Cyclopentanecarbaldehyde

  • EINECS 212-829-7
  • CAS No. 872-53-7
  • Article Data153
  • CAS DataBase
  • Density 1.029 g/cm3
  • Solubility Soluble in water and ethanol
  • Melting Point
  • Formula C6H10O
  • Boiling Point 133.3 °C at 760 mmHg
  • Molecular Weight 98.1448
  • Flash Point 36 °C
  • Transport Information UN 1989 3/PG 3
  • Appearance clear colorless to light yellow liquid
  • Safety 16-26-36
  • Risk Codes 10-36/37/38
  • Molecular Structure Molecular Structure of 872-53-7 (Cyclopentanecarbaldehyde)
  • Hazard Symbols IrritantXi
  • Synonyms Cyclopentylformaldehyde;Formylcyclopentane;NSC 17492;Cyclopentyl aldehyde;Cyclopentanealdehyde;Cyclopentanecarboxaldehyde;
  • PSA 17.07000
  • LogP 1.37550

Synthetic route

Sodium; 1-oxa-spiro[2.4]heptane-2-carboxylate
89848-73-7

Sodium; 1-oxa-spiro[2.4]heptane-2-carboxylate

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With sulfuric acid stream of steam under a carbon dioxide atmosphere;100%
cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With erbium(III) triflate In dichloromethane for 5h; Heating;99%
With thorium dioxide at 330℃;
With phthalic anhydride
With magnesium bromide ethyl etherate Verdampfen des Aethers und Zersetzen des Reaktionsprodukts mit Wasser;
With aluminum oxide; lithium bromide In toluene for 2h; Heating;
carbon monoxide
201230-82-2

carbon monoxide

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

A

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

B

Cyclopentane
287-92-3

Cyclopentane

Conditions
ConditionsYield
With hydrogen; N-dodecyl-N-(2-hydroxyethyl)-N,N-dimethylammonium bromide; {Rh(cod)[μ-S(CH2)3Si(OMe)3]}2; triphenylphosphine In water; butan-1-ol at 80℃; under 10350.8 Torr; for 15h; microemulsion/sol-gel;A 98.5%
B 1.5%
...Expand
cyclohexene
110-83-8

cyclohexene

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
Stage #1: cyclohexene With ammonium iodide; water; sodium dodecyl-sulfate for 0.5h;
Stage #2: With Oxone at 20℃; for 0.13h; regioselective reaction;		95%
With iodobenzene complex with boron trifluoride etherate In dichloromethane at -15 - -10℃; for 0.25h;60%
With iodosylbenzene; sulfuric acid for 72h; Ambient temperature;44%
cyclopentanecarboxylic acid
3400-45-1

cyclopentanecarboxylic acid

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With thexylchloroborane-Me2SO4 In dichloromethane for 0.25h; Ambient temperature;89%
Multi-step reaction with 2 steps
1: lithium aluminium hydride / diethyl ether
2: pyridinium chlorochromate
View Scheme
N′-(cyclopentylmethylene)-4-methylbenzenesulfonohydrazide
36601-82-8

N′-(cyclopentylmethylene)-4-methylbenzenesulfonohydrazide

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With Cr-MCM-41 zeolite on silica gel for 0.116667h; microwave irradiation;88%
cyclopentanecarbaldehyde oxime
70341-45-6

cyclopentanecarbaldehyde oxime

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With Cr-MCM-41 zeolite on silica gel for 0.133333h; microwave irradiation;86%
cyclohexene
110-83-8

cyclohexene

A

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

B

cyclohexanone
108-94-1

cyclohexanone

C

Cyclohex-2-enol
822-67-3

Cyclohex-2-enol

Conditions
ConditionsYield
With dipotassium peroxodisulfate; copper(II) sulfate In water; acetonitrile at 60℃; for 6h;A 80%
B 2%
C 7%
...Expand
1-amino-cyclopentanemethanol
3637-61-4

1-amino-cyclopentanemethanol

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With Celite; pyridinium chlorochromate In dichloromethane at 20℃; for 16h;78%
With dipyridinium dichromate In dichloromethane for 24h; Ambient temperature;10%
With copper oxide-chromium oxide catalyst at 300℃;
N-Formylpiperidine
2591-86-8

N-Formylpiperidine

cyclopentylmagnesium bromide
33240-34-5

cyclopentylmagnesium bromide

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
In diethyl ether for 15h; Ambient temperature;72%
4-morpholinecarboxaldehyde
4394-85-8

4-morpholinecarboxaldehyde

cyclopentylmagnesium bromide
33240-34-5

cyclopentylmagnesium bromide

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
In diethyl ether for 0.5h; Ambient temperature;69%
carbon monoxide
201230-82-2

carbon monoxide

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

A

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

B

cyclopentane-1,3-bis(carboxaldehyde)
4750-17-8

cyclopentane-1,3-bis(carboxaldehyde)

Conditions
ConditionsYield
With 2,2'-bis((diphenylphosphino)methyl)-1,1'-biphenyl; dirhodium tetraacetate; hydrogen; triethylamine In toluene at 100℃; under 22502.3 Torr; for 3h; Kinetics; Reagent/catalyst; Autoclave;A 56%
B 18%
With dirhodium tetraacetate; hydrogen; triethylamine; bis-diphenylphosphinomethane In toluene at 100℃; under 22502.3 Torr; for 3h; Kinetics; Autoclave;A 9%
B 10%
...Expand
methanol
67-56-1

methanol

cyclohexene
110-83-8

cyclohexene

A

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

B

3-methoxycyclohexene
2699-13-0

3-methoxycyclohexene

C

1,2-dimethoxycyclohexane
19752-95-5

1,2-dimethoxycyclohexane

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; sulfuric acid at -15℃; for 2.33333h;A 42%
B n/a
C n/a
...Expand
N-Formylpiperidine
2591-86-8

N-Formylpiperidine

Cyclopentyl bromide
137-43-9

Cyclopentyl bromide

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With iodine; magnesium In tetrahydrofuran; diethyl ether at 20℃; for 1.5h;37.8%
Stage #1: Cyclopentyl bromide With iodine; magnesium In tetrahydrofuran at 20℃;
Stage #2: N-Formylpiperidine In diethyl ether at 20℃; for 1.5h;		37.8%
carbon monoxide
201230-82-2

carbon monoxide

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With dirhodium tetraacetate; 2,3-bis(diphenylphosphino)bicyclo-[2.2.1]hept-5-ene; hydrogen; triethylamine In toluene at 100℃; under 22502.3 Torr; for 3h; Kinetics; Reagent/catalyst; Autoclave;29%
1,2-Cyclohexanediol
931-17-9

1,2-Cyclohexanediol

A

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

B

hexahydrobenzo[d][1,3]dioxol-2-one

hexahydrobenzo[d][1,3]dioxol-2-one

Conditions
ConditionsYield
With isocyanate de chlorosulfonyle In benzene 1.) 0 deg C, 2.) reflux, 0.5 h;A 10%
B n/a
carbon monoxide
201230-82-2

carbon monoxide

acetone
67-64-1

acetone

cyclopentene
142-29-0

cyclopentene

A

(R)-4-cyclopentyl-4-hydroxy-2-butanone

(R)-4-cyclopentyl-4-hydroxy-2-butanone

B

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

C

(S)-4-cyclopentyl-4-hydroxy-2-butanone

(S)-4-cyclopentyl-4-hydroxy-2-butanone

Conditions
ConditionsYield
With triphenyl phosphite; hydrogen; acetylacetonatodicarbonylrhodium(l); L-proline at 40℃; for 72h; Title compound not separated from byproducts.;A n/a
B 6%
C n/a
...Expand
Tetrahydropyran-2-methanol
100-72-1

Tetrahydropyran-2-methanol

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With aluminum oxide at 420 - 450℃;
phthalic anhydride
85-44-9

phthalic anhydride

cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

A

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

B

1,2-Cyclohexanediol
931-17-9

1,2-Cyclohexanediol

C

cyclohexa-1,3-diene
1165952-91-9

cyclohexa-1,3-diene

...Expand
1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

trans-2-hydroxycyclohexyl p-toluenesulfonate
15051-90-8, 89959-75-1, 99835-44-6, 132961-67-2

trans-2-hydroxycyclohexyl p-toluenesulfonate

A

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

B

1,2-Cyclohexanediol
931-17-9

1,2-Cyclohexanediol

...Expand
1-cyclopentene-1-carboxaldehyde
6140-65-4

1-cyclopentene-1-carboxaldehyde

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With diethyl ether; palladium Hydrogenation;
With hydrogen; palladium on activated charcoal
With hydrogen; palladium on activated charcoal In methanol
1-Methylol-1-hydroxycyclopentan
74397-18-5

1-Methylol-1-hydroxycyclopentan

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With sulfuric acid
1,2-Cyclohexanediol
931-17-9

1,2-Cyclohexanediol

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With phthalic anhydride
cyclopentanecarbaldehyde diethylacetal
32122-35-3

cyclopentanecarbaldehyde diethylacetal

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With sulfuric acid
With diclazuril; water-d2 In acetone at 23℃; Rate constant;
2-Iodo-cyclohexanol
28141-32-4

2-Iodo-cyclohexanol

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With silver nitrate
With sodium bromate; sulfuric acid; sodium bromide In methanol; 1,2-dichloro-ethane at 0 - 10℃;
(+/-)-trans-2-sulfooxy-1-methoxy-cyclohexane

(+/-)-trans-2-sulfooxy-1-methoxy-cyclohexane

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
Erhitzen;
trans-1,2-cyclohexandiol
1460-57-7

trans-1,2-cyclohexandiol

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With carbon dioxide; sulfuric acid at 150℃;
With nitric acid at 85℃;
With aluminum oxide; nitrogen at 250 - 300℃; unter vermindertem Druck;
With aluminum oxide; water at 250 - 300℃; unter vermindertem Druck;
Multi-step reaction with 2 steps
1: (i) NaIO4, (ii) KOH
2: H2 / Pd-C
View Scheme
trans-2-chlorocyclohexanol
6628-80-4

trans-2-chlorocyclohexanol

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
nachfolgend Einw. von Magnesiumbromid-aetherat;
trans-2-chlorocyclohexanol
6628-80-4

trans-2-chlorocyclohexanol

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

Conditions
ConditionsYield
With ethylmagnesium bromide nachfolgend Einw. von Magnesiumbromid-aetherat;
trans-2-chlorocyclohexanol
6628-80-4

trans-2-chlorocyclohexanol

A

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

B

1,2-Cyclohexanediol
931-17-9

1,2-Cyclohexanediol

Conditions
ConditionsYield
With sulfuric acid
With calcium chloride
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

(E)-ethyl 3-cyclopentylprop-2-enoate
2931-23-9, 17343-83-8

(E)-ethyl 3-cyclopentylprop-2-enoate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0℃; for 1h; Wadsworth-Horner-Emmons reaction;
Stage #2: cyclopentanealdehyde In tetrahydrofuran at -78 - 20℃; for 1h;		100%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #2: cyclopentanealdehyde In tetrahydrofuran at 20℃; for 17h; Inert atmosphere;		58%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

aniline
62-53-3

aniline

(N-phenyl)aminomethylcyclopentane
84257-36-3

(N-phenyl)aminomethylcyclopentane

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol; water at 20℃; for 0.5h;100%
Stage #1: cyclopentanealdehyde; aniline With 1-{6-[dibutyl(chloro)stannyl]hexyl}-3-methyl-1H-imidazolium iodide at 20℃; for 0.166667h;
Stage #2: With phenylsilane at 20℃; for 4h;		88%
Stage #1: cyclopentanealdehyde; aniline In dichloromethane at 20℃; for 4h;
Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;		70%
With tetra(n-butyl)ammonium hydrogensulfate; dimethyl sulfoxide at 20℃; for 5h; Electrolysis;12%
ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate dihydrochloride

ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate dihydrochloride

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-1-(cyclopentylmethyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylate
876160-33-7

ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-1-(cyclopentylmethyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylate

Conditions
ConditionsYield
Stage #1: ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate dihydrochloride; cyclopentanealdehyde With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 0.0833333h;
Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 2h;
Stage #3: With sodium hydrogencarbonate In water; 1,2-dichloro-ethane		100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

(S)-1-(2,5-dioxo-1-phenylpyrrolidin-3-yl)cyclopetanecarboxaldehyde
1242461-34-2

(S)-1-(2,5-dioxo-1-phenylpyrrolidin-3-yl)cyclopetanecarboxaldehyde

Conditions
ConditionsYield
With (S)-3-amino-3-phenylpropanoic acid; caesium carbonate In dichloromethane at 20℃; for 48h; Michael Addition; enantioselective reaction;100%
With NH2-Phg-(D-Pro)-Gly-Leu-OH In acetonitrile at 20℃; for 72h; Michael Addition; enantioselective reaction;95%
Stage #1: cyclopentanealdehyde With dmap; tert-butyl (2S,3R)-2-amino-3-hydroxybutanoate; SULFAMIDE In dichloromethane at 23℃; for 0.0333333h; Michael addition;
Stage #2: N-phenyl-maleimide In dichloromethane at 23℃; for 16h; Michael addition; optical yield given as %ee; enantioselective reaction;		93%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

methyl 2-{(2R,4S,5S)-5-amino-4-[4-(trifluoromethyl)phenyl]tetrahydro-2H-pyran-2-yl}acetate hydrochloride
1316756-78-1

methyl 2-{(2R,4S,5S)-5-amino-4-[4-(trifluoromethyl)phenyl]tetrahydro-2H-pyran-2-yl}acetate hydrochloride

methyl 2-{(2R,4S,5S)-5-[bis(cyclopentylmethyl)amino]-4-[4-(trifluoromethyl)phenyl]tetrahydro-2H-pyran-2-yl}acetate
1316757-04-6

methyl 2-{(2R,4S,5S)-5-[bis(cyclopentylmethyl)amino]-4-[4-(trifluoromethyl)phenyl]tetrahydro-2H-pyran-2-yl}acetate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 20℃; for 6h;100%
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

(R)-1-(2,5-dioxo-1-phenylpyrrolidin-3-yl)cyclopentane-1-carbaldehyde
1319746-63-8

(R)-1-(2,5-dioxo-1-phenylpyrrolidin-3-yl)cyclopentane-1-carbaldehyde

Conditions
ConditionsYield
With L-Asp(t-Bu); potassium hydroxide In dichloromethane at 20℃; for 48h; Michael Addition; enantioselective reaction;100%
With C64H94N6O4S2 In dichloromethane at 20℃; Michael Addition; enantioselective reaction;95%
With 2-({[(1R,2R)-2-aminocyclohexyl]amino}{[3,5-bis(trifluoromethyl)benzyl]amino}methylidene)-2,3-dihydro-1H-indene-1,3-dione; benzoic acid In para-xylene at 40℃; for 48h; Michael Addition; enantioselective reaction;95%
With 1-[(1R,2R)-2-aminocyclohexyl]-3-[4-(n-perfluorooctyl)phenyl]-thiourea; benzoic acid In dichloromethane at 20℃; for 76h; asymmetric Michael addition; optical yield given as %ee; enantioselective reaction;92%
With 1H-imidazole; 1-[(1S,2S)-2-aminocyclohexyl]-2,3-diisopropylguanidine In water; N,N-dimethyl-formamide at 0℃; for 96h; Michael Addition; enantioselective reaction;92%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

cyclopentylmethyl cyclopentanecarboxylate

cyclopentylmethyl cyclopentanecarboxylate

Conditions
ConditionsYield
With [(ImtBuN)U{N(SiMe3)2}3] In benzene-d6 at 20℃; for 12h; Reagent/catalyst;100%
With C48H69N3Th In benzene-d6 at 20℃; for 3h; Reagent/catalyst; Tishchenko-Claisen Dismutation; Glovebox; Inert atmosphere;100 %Spectr.
With C38H53N3Th In benzene-d6 at 20℃; for 24h; Reagent/catalyst; Time; Glovebox;
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

benzylamine
100-46-9

benzylamine

(E)-N-benzyl-1-cyclopentylmethanimine

(E)-N-benzyl-1-cyclopentylmethanimine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 21h;100%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

nitromethane
75-52-5

nitromethane

(R)-(-)-2-nitro-(1-cyclopentyl)ethanol

(R)-(-)-2-nitro-(1-cyclopentyl)ethanol

Conditions
ConditionsYield
With C36H44N4O4S2; copper(I) bromide In methanol at 20℃; for 36h; Henry reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
With potassium hydroxide; potassium iodide; C55H69F12N7S2*ClH In water; toluene at 0℃; for 5h;76%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

[N-(p-tolylsulfonyl)imino]phenyliodinane
55962-05-5

[N-(p-tolylsulfonyl)imino]phenyliodinane

N-tosylcyclopentanecarboxamide
121239-32-5

N-tosylcyclopentanecarboxamide

Conditions
ConditionsYield
Ru(5,10,15,20-tetrakis(p-tolyl)porphyrinato)(CO) In dichloromethane at 20℃; for 0.5h;99%
With pyridine; iron(II) chloride In dichloromethane at 20℃; for 18h; Molecular sieve; Inert atmosphere;99%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

1-methoxy-2-((E)-2-nitrovinyl)benzene
3316-24-3

1-methoxy-2-((E)-2-nitrovinyl)benzene

A

(R)-1-[1-(2-methoxyphenyl)-2-nitroethyl]cyclopentanecarbaldehyde
1198362-14-9

(R)-1-[1-(2-methoxyphenyl)-2-nitroethyl]cyclopentanecarbaldehyde

B

(S)-1-[1-(2-methoxyphenyl)-2-nitroethyl]cyclopentanecarbaldehyde

(S)-1-[1-(2-methoxyphenyl)-2-nitroethyl]cyclopentanecarbaldehyde

Conditions
ConditionsYield
7,7-dimethyl-2(R)-hydroxy-bicyclo[2.2.1]heptane-1-carboxylic acid-[pyrrolidin-2(S)-ylmethyl]amide at 0℃; for 12h; Product distribution / selectivity; Michael addition reaction;A 99%
B n/a
With 7,7-dimethyl-2(R)-hydroxy-bicyclo[2.2.1]heptane-1-carboxylic acid-[pyrrolidin-2(S)-ylmethyl]amide; benzoic acid at 0℃; for 12h; asymmetric Michael reaction; Neat (no solvent); optical yield given as %ee; enantioselective reaction;
With (3R,5S)-5-[{{(1S)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}methylthio}methyl]pyrrolidin-3-ol In toluene at 0℃; for 120h; Michael addition; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
...Expand
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

(E)-1-methoxy-3-(2-nitrovinyl)benzene
3179-09-7, 55446-68-9

(E)-1-methoxy-3-(2-nitrovinyl)benzene

(R)-1-[1-(3-methoxyphenyl)-2-nitroethyl]cyclopentanecarbaldehyde
1198362-15-0

(R)-1-[1-(3-methoxyphenyl)-2-nitroethyl]cyclopentanecarbaldehyde

Conditions
ConditionsYield
With 7,7-dimethyl-2(R)-hydroxy-bicyclo[2.2.1]heptane-1-carboxylic acid-[pyrrolidin-2(S)-ylmethyl]amide; benzoic acid at 0℃; for 12h; asymmetric Michael reaction; Neat (no solvent); optical yield given as %ee; enantioselective reaction;99%
7,7-dimethyl-2(R)-hydroxy-bicyclo[2.2.1]heptane-1-carboxylic acid-[pyrrolidin-2(S)-ylmethyl]amide at 0℃; for 12h; Product distribution / selectivity; Michael addition reaction;99%
With C64H94N6O4S2 In dichloromethane at 20℃; for 84h; Michael Addition; enantioselective reaction;72%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

methyl 3-amino-5-chloro-2-methylbenzoate
294190-18-4

methyl 3-amino-5-chloro-2-methylbenzoate

methyl 5-chloro-3-((cyclopentylmethyl)amino)-2-methylbenzoate
1403596-65-5

methyl 5-chloro-3-((cyclopentylmethyl)amino)-2-methylbenzoate

Conditions
ConditionsYield
Stage #1: cyclopentanealdehyde; methyl 3-amino-5-chloro-2-methylbenzoate With acetic acid In methanol at 20℃; for 8h;
Stage #2: With methanol; sodium cyanoborohydride at 0 - 20℃;		99%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

nitromethane
75-52-5

nitromethane

(S)-1-Cyclopentyl-2-nitro-ethanol

(S)-1-Cyclopentyl-2-nitro-ethanol

Conditions
ConditionsYield
With (2S,5R)-2-(methylaminomethyl)-1-methyl-5-phenylpyrrolidine; triethylamine; copper dichloride In tetrahydrofuran at -20℃; for 44h; Henry Nitro Aldol Condensation; Inert atmosphere; Schlenk technique; enantioselective reaction;99%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

[(ImDippN)Th{N(SiMe3)2}3]

[(ImDippN)Th{N(SiMe3)2}3]

(bis(trimethylsilyl)amino)(cyclopentyl)methyl cyclopentanecarboxylate

(bis(trimethylsilyl)amino)(cyclopentyl)methyl cyclopentanecarboxylate

Conditions
ConditionsYield
In benzene-d6 for 3h;99%
methanol
67-56-1

methanol

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

(dimethoxymethyl)cyclopentane
20117-79-7

(dimethoxymethyl)cyclopentane

Conditions
ConditionsYield
With phosphoric acid functionalized ethanolamine grafted polyacrylonitrile fiber at 65℃; for 0.333333h; Green chemistry;99%
With titanium tetrachloride; triethylamine In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere;77%
With thio-xanthene-9-one for 1.5h; Irradiation; Sealed tube; Green chemistry;75%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

3-cyclopentaneacrylonitrile
591769-05-0

3-cyclopentaneacrylonitrile

Conditions
ConditionsYield
With HT-O-t-Bu In N,N-dimethyl-formamide for 2.5h; Wadsworth-Emmons reaction; Heating;98%
Stage #1: diethyl 1-cyanomethylphosphonate With potassium tert-butylate In tetrahydrofuran at 0 - 20℃;
Stage #2: cyclopentanealdehyde In tetrahydrofuran at 0 - 20℃; for 64h;		89%
Stage #1: diethyl 1-cyanomethylphosphonate With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h; Cooling with ice;
Stage #2: cyclopentanealdehyde In tetrahydrofuran at 0 - 20℃;		67%
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 49h;46%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

dibenzylamine
103-49-1

dibenzylamine

N,N-dibenzyl-1-cyclopentyl-3-(trimethylsilyl)-2-propyn-1-amine
872713-34-3

N,N-dibenzyl-1-cyclopentyl-3-(trimethylsilyl)-2-propyn-1-amine

Conditions
ConditionsYield
With (R)-1-(2-(diphenylphosphanyl)naphthalen-1-yl)isoquinoline; copper(I) bromide In toluene at 20℃;98%
With (R)-1-(2-(diphenylphosphanyl)naphthalen-1-yl)isoquinoline; 4 A molecular sieve; copper(I) bromide In decane; toluene at 20℃; for 144h;98%
With (R)-1-(2-(diphenylphosphanyl)naphthalen-1-yl)isoquinoline; 4 A molecular sieve; copper(I) bromide In toluene at 20℃; for 144h;98%
With (S)-1-(2-(diphenylphosphanyl)naphthalen-1-yl)isoquinoline; copper(I) bromide In toluene at 20℃; for 43h; Schlenk technique; Inert atmosphere; Molecular sieve; enantioselective reaction;97%
With C44H30F5N2P; copper(I) bromide In toluene at 0℃; for 24h; Molecular sieve; enantioselective reaction;70%
...Expand
bis(4-chlorobenzyl) diazene-1,2-dicarboxylate

bis(4-chlorobenzyl) diazene-1,2-dicarboxylate

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

C22H22Cl2N2O5
1191377-66-8

C22H22Cl2N2O5

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium trifluoromethanesulfonimide at 40℃; for 2h;98%
Nitroethane
79-24-3

Nitroethane

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

(1R,2R)-1-cyclopentyl-2-nitropropan-1-ol
1239610-43-5

(1R,2R)-1-cyclopentyl-2-nitropropan-1-ol

Conditions
ConditionsYield
With 4-methyl-morpholine; C31H33CuF6N5O6S2 In 1,4-dioxane at 0℃; for 24h; Henry reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;98%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

di-isopropyl azodicarboxylate
2446-83-5

di-isopropyl azodicarboxylate

1-cyclopentylcarbonyl-1,2-hydrazinedicarboxylic acid 1,2-diisopropyl ester
1259419-00-5

1-cyclopentylcarbonyl-1,2-hydrazinedicarboxylic acid 1,2-diisopropyl ester

Conditions
ConditionsYield
In water at 20℃; for 8h;98%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

1-nitro-4-(2-nitrovinyl)benzene
3156-41-0

1-nitro-4-(2-nitrovinyl)benzene

(R)-1-[1-(4-nitrophenyl)-2-nitroethyl]cyclopentanecarbaldehyde
1609238-77-8

(R)-1-[1-(4-nitrophenyl)-2-nitroethyl]cyclopentanecarbaldehyde

Conditions
ConditionsYield
With C13H28N2; benzoic acid In neat (no solvent) at 4℃; for 12h; Michael Addition; Green chemistry; stereoselective reaction;98%
Stage #1: cyclopentanealdehyde With (S)-1-(pyrrolidine-2-ylmethyl)-1H-pyrazole; benzoic acid In neat (no solvent) at 0℃; for 0.333333h;
Stage #2: 1-nitro-4-(2-nitrovinyl)benzene In neat (no solvent) at 0℃; for 24h; Michael Addition; enantioselective reaction;		95%
Stage #1: cyclopentanealdehyde With (S)-2-(pyrrolidin-2-ylmethoxy)isoindoline-1,3-dione; 4-nitro-benzoic acid In neat (no solvent) at 0℃; for 0.333333h; Michael Addition;
Stage #2: 1-nitro-4-(2-nitrovinyl)benzene In neat (no solvent) at 0℃; for 48h; Michael Addition; enantioselective reaction;		93%
Stage #1: cyclopentanealdehyde With (S)-1-(pyrrolidin-2-ylmethoxy)-1H-benzo[d][1,2,3]triazole; benzoic acid In water at 0℃; for 0.333333h;
Stage #2: 1-nitro-4-(2-nitrovinyl)benzene In water at 0℃; for 36h; Michael Addition; enantioselective reaction;		91%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

anthranilic acid amide
28144-70-9

anthranilic acid amide

(R)-2-cyclopentyl-2,3-dihydroquinazolin-4(1H)-one

(R)-2-cyclopentyl-2,3-dihydroquinazolin-4(1H)-one

Conditions
ConditionsYield
With (11aR)-10,11,12,13-tetrahydro-5-hydroxy-3,7-bis[2,4,6-triisopropylphenyl]-5-oxide-diindeno[7,1-de:1',7’-fg][1,3,2]dioxaphosphocin In m-xylene at 25℃; for 12h; enantioselective reaction;98%
(R)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid
192330-11-3

(R)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

(2R)-4-(tert-butoxycarbonyl)-1-(cyclopentylmethyl)piperazine-2-carboxylic acid
869681-92-5

(2R)-4-(tert-butoxycarbonyl)-1-(cyclopentylmethyl)piperazine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (R)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid; cyclopentanealdehyde With acetic acid In tetrahydrofuran for 0.5h;
Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran for 12.0833h;		97.4%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

1-nitro-2-(4-chlorophenyl)ethylene
101671-01-6

1-nitro-2-(4-chlorophenyl)ethylene

(R)-1-[1-(4-chlorophenyl)-2-nitroethyl]cyclopentanecarbaldehyde
1198362-24-1

(R)-1-[1-(4-chlorophenyl)-2-nitroethyl]cyclopentanecarbaldehyde

Conditions
ConditionsYield
With 7,7-dimethyl-2(R)-hydroxy-bicyclo[2.2.1]heptane-1-carboxylic acid-[pyrrolidin-2(S)-ylmethyl]amide; benzoic acid at 0℃; for 1h; asymmetric Michael reaction; Neat (no solvent); optical yield given as %ee; enantioselective reaction;97%
7,7-dimethyl-2(R)-hydroxy-bicyclo[2.2.1]heptane-1-carboxylic acid-[pyrrolidin-2(S)-ylmethyl]amide at 0℃; for 24h; Product distribution / selectivity; Michael addition reaction;97%
With C64H94N6O4S2 In dichloromethane at 20℃; for 60h; Michael Addition; enantioselective reaction;84%
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

(2-amino-4,5-difluoro-phenyl)-carbamic acid tert-butyl ester
1000698-88-3

(2-amino-4,5-difluoro-phenyl)-carbamic acid tert-butyl ester

Benzyl isocyanide
88333-03-3, 10340-91-7

Benzyl isocyanide

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

N-benzyl-2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclopentyl-acetamide
1265885-28-6

N-benzyl-2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclopentyl-acetamide

Conditions
ConditionsYield
Stage #1: cyclopentanealdehyde; (2-amino-4,5-difluoro-phenyl)-carbamic acid tert-butyl ester In methanol at 20℃; for 0.0833333h;
Stage #2: Benzyl isocyanide; para-chlorobenzoic acid In methanol for 19h;		97%
...Expand
cyclopentanealdehyde
872-53-7

cyclopentanealdehyde

methyl 3-(benzofuran-2-yl)-3-oxopropanoate

methyl 3-(benzofuran-2-yl)-3-oxopropanoate

C18H18O4
1272564-90-5

C18H18O4

Conditions
ConditionsYield
With piperidine; acetic acid In benzene at 100℃; for 16h; Knoevenagel condensation; Inert atmosphere; optical yield given as %de;97%

Cyclopentanecarbaldehyde Chemical Properties

Molecule structure of Cyclopentanecarbaldehyde (CAS NO.872-53-7):

IUPAC: Cyclopentanecarbaldehyde 
Molecular Weight: 98.143 g/mol
Molecular Formula: C6H10O 
Density: 0.919 g/mL at 25 °C(lit.)
Boiling Point: 140-141 °C(lit.)
Flash Point: 36 °C
Index of Refraction: 1.535
Molar Refractivity: 29.66 cm3
Molar Volume: 95.2 cm3
Polarizability: 11.76×10-24 cm3
Surface Tension: 37 dyne/cm 
Enthalpy of Vaporization: 37.08 kJ/mol
Vapour Pressure: 8.51 mmHg at 25 °C
XLogP3-AA: 1.3
H-Bond Acceptor: 1
Rotatable Bond Count: 1
Tautomer Count: 2
Exact Mass: 98.073165
MonoIsotopic Mass: 98.073165
Topological Polar Surface Area: 17.1
Heavy Atom Count: 7
Complexity: 62.6 
Canonical SMILES: C1CCC(C1)C=O
InChI: InChI=1S/C6H10O/c7-5-6-3-1-2-4-6/h5-6H,1-4H2
InChIKey: VELDYOPRLMJFIK-UHFFFAOYSA-N
EINECS 212-829-7
Product Categories: Cycloalkanes; Aldehydes; C1 to C6; Carbonyl Compounds

Cyclopentanecarbaldehyde Uses

 Cyclopentanecarbaldehyde (CAS NO.872-53-7) is used as an important pharmaceutical intermediate.

Cyclopentanecarbaldehyde Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 10-36/37/38 
R10:Flammable. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 16-26-36 
S16:Keep away from sources of ignition. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
RIDADR: UN 1989 3/PG 3
WGK Germany: 3

Cyclopentanecarbaldehyde Specification

 Cyclopentanecarbaldehyde (CAS NO.872-53-7) is clear colorless to light yellow liquid.

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