Product Name

  • Name

    tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione

  • EINECS 227-286-1
  • CAS No. 5763-49-5
  • Density 1.309 g/cm3
  • Solubility
  • Melting Point
  • Formula C7H8O3
  • Boiling Point 289.2 °C at 760 mmHg
  • Molecular Weight 140.139
  • Flash Point 140.4 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 5763-49-5 (tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione)
  • Hazard Symbols
  • Synonyms 1,2-Cyclopentanedicarboxylicanhydride (6CI,7CI,8CI);1H-Cyclopenta[c]furan-1,3(3aH)-dione, tetrahydro-;Tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione;Tetrahydrocyclopenta[c]furan-1,3-dione;
  • PSA 43.37000
  • LogP 0.48610

Synthetic route

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

Conditions
ConditionsYield
at 150 - 160℃; anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2);
Multi-step reaction with 2 steps
1: concentrated hydrochloric acid / 180 °C
2: acetyl chloride / 140 °C / im Einschlussrohr
View Scheme
With acetic anhydride for 20h; Heating / reflux;
trans-1,2-cyclopentanedicarboxylic acid
80656-14-0

trans-1,2-cyclopentanedicarboxylic acid

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

Conditions
ConditionsYield
at 300℃; anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2);
With acetic anhydride anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2);
With acetyl chloride at 140℃; im Einschlussrohr; anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2);
With acetic anhydride anschliessend Erhitzen auf 170grad bei 20 mmHg Druck; anhydride of/the/ trans-cyclopentane-dicarboxylic acid-(1.2);
Multi-step reaction with 2 steps
1: acetic acid anhydride / Loesen in Wasser oder in Kalilauge und Ansaeuern
2: 150 - 160 °C
View Scheme
1,1,2,2-Cyclopentantetracarbonsaeure-tetraethylester
50708-47-9

1,1,2,2-Cyclopentantetracarbonsaeure-tetraethylester

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: glacial acetic acid; concentrated sulfuric acid; water
2: acetic acid anhydride / Loesen in Wasser oder in Kalilauge und Ansaeuern
3: 150 - 160 °C
View Scheme
Multi-step reaction with 2 steps
1: glacial acetic acid; concentrated sulfuric acid; water
2: acetic acid anhydride
View Scheme
(trans)-1,2-cyclopentanedicarboxylic acid
21917-20-4

(trans)-1,2-cyclopentanedicarboxylic acid

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

Conditions
ConditionsYield
In benzene8.60 g (81%)
methanol
67-56-1

methanol

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

(+/-)-cis-2-(methoxycarbonyl)cyclopentane carboxylic acid

(+/-)-cis-2-(methoxycarbonyl)cyclopentane carboxylic acid

Conditions
ConditionsYield
at 50 - 55℃; for 5h;98%
at 50 - 55℃; for 16h;
carbon tetrabromide
558-13-4

carbon tetrabromide

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

3-(dibromomethylene)hexahydro-1H-cyclopenta[c]furan-1-one

3-(dibromomethylene)hexahydro-1H-cyclopenta[c]furan-1-one

Conditions
ConditionsYield
Stage #1: carbon tetrabromide With triphenylphosphine In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #2: With triethylamine In tetrahydrofuran for 0.0833333h; Inert atmosphere;
Stage #3: 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione In tetrahydrofuran at 0 - 20℃; Inert atmosphere;		24%
(R)-Phenylglycinol
56613-80-0

(R)-Phenylglycinol

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

2-((R)-2-Hydroxy-1-phenyl-ethylcarbamoyl)-cyclopentanecarboxylic acid
86331-36-4, 95462-66-1

2-((R)-2-Hydroxy-1-phenyl-ethylcarbamoyl)-cyclopentanecarboxylic acid

Conditions
ConditionsYield
In tetrahydrofuran 1.) 0 deg C, 15 min; 2.) r.t., 1 h;
methylamine
74-89-5

methylamine

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

N-Methylcyclopentane-1,2-dicarboximide
71099-01-9

N-Methylcyclopentane-1,2-dicarboximide

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

KOH-solution

KOH-solution

cis-1,2-cyclopentanedicarboxylic acid
1461-96-7

cis-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
durch Ansaeuern; anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2);
2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

air

air

trans-1,2-cyclopentanedicarboxylic acid
80656-14-0

trans-1,2-cyclopentanedicarboxylic acid

Conditions
ConditionsYield
anhydride of/the/ trans-cyclopentane-dicarboxylic acid-(1.2);
2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2)

anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2)

Conditions
ConditionsYield
bei der Destillation unter vermindertem Druck; anhydride of/the/ trans-cyclopentane-dicarboxylic acid-(1.2);
thiazol-2-ylzinc(II) bromide
173382-28-0

thiazol-2-ylzinc(II) bromide

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

trans-2-(1,3-thiazol-2-ylcarbonyl)cyclopentanecarboxylic acid

trans-2-(1,3-thiazol-2-ylcarbonyl)cyclopentanecarboxylic acid

Conditions
ConditionsYield
Stage #1: thiazol-2-ylzinc(II) bromide; 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃;
Stage #2: With sodium hydroxide In tetrahydrofuran; diethyl ether; water
Stage #3: With hydrogenchloride In water pH=1;
2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

(1S,5R)-3-oxabicyclo[3.3.0]octan-2-one
75658-84-3

(1S,5R)-3-oxabicyclo[3.3.0]octan-2-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: tetrahydrofuran / 1.) 0 deg C, 15 min; 2.) r.t., 1 h
2: sodium acetate / 3 h / 100 °C
3: 1 N HCl in MeOH / 2 h / Heating
4: 94 percent / NaAlH2(OCH2CH2OCH3)2 / toluene / 4 h / -78 °C
5: 96 percent / NaBH4 / aq. ethanol / 4 h / 50 °C
6: 2 N H2SO4 / 2 h / 80 °C
View Scheme
2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

(3aS,6aR)-hexahydro-1H-cyclopenta[c]furan-1-one
121960-86-9

(3aS,6aR)-hexahydro-1H-cyclopenta[c]furan-1-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: tetrahydrofuran / 1.) 0 deg C, 15 min; 2.) r.t., 1 h
2: sodium acetate / 3 h / 100 °C
3: 1 N HCl in MeOH / 2 h / Heating
4: 94 percent / NaAlH2(OCH2CH2OCH3)2 / toluene / 4 h / -78 °C
5: 96 percent / NaBH4 / aq. ethanol / 4 h / 50 °C
6: 2 N H2SO4 / 2 h / 80 °C
View Scheme
2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

2-Hydroxymethyl-cyclopentanecarboxylic acid ((R)-2-hydroxy-1-phenyl-ethyl)-amide
86331-50-2

2-Hydroxymethyl-cyclopentanecarboxylic acid ((R)-2-hydroxy-1-phenyl-ethyl)-amide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: tetrahydrofuran / 1.) 0 deg C, 15 min; 2.) r.t., 1 h
2: sodium acetate / 3 h / 100 °C
3: 1 N HCl in MeOH / 2 h / Heating
4: 94 percent / NaAlH2(OCH2CH2OCH3)2 / toluene / 4 h / -78 °C
5: 96 percent / NaBH4 / aq. ethanol / 4 h / 50 °C
View Scheme
2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

2-((R)-2-Hydroxy-1-phenyl-ethyl)-tetrahydro-cyclopenta[c]pyrrole-1,3-dione
86331-31-9

2-((R)-2-Hydroxy-1-phenyl-ethyl)-tetrahydro-cyclopenta[c]pyrrole-1,3-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran / 1.) 0 deg C, 15 min; 2.) r.t., 1 h
2: sodium acetate / 3 h / 100 °C
3: 1 N HCl in MeOH / 2 h / Heating
View Scheme
2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

3-Hydroxy-2-((R)-2-hydroxy-1-phenyl-ethyl)-hexahydro-cyclopenta[c]pyrrol-1-one
86331-45-5, 95462-61-6

3-Hydroxy-2-((R)-2-hydroxy-1-phenyl-ethyl)-hexahydro-cyclopenta[c]pyrrol-1-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrahydrofuran / 1.) 0 deg C, 15 min; 2.) r.t., 1 h
2: sodium acetate / 3 h / 100 °C
3: 1 N HCl in MeOH / 2 h / Heating
4: 94 percent / NaAlH2(OCH2CH2OCH3)2 / toluene / 4 h / -78 °C
View Scheme
2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

Acetic acid (R)-2-(1,3-dioxo-hexahydro-cyclopenta[c]pyrrol-2-yl)-2-phenyl-ethyl ester
86338-97-8

Acetic acid (R)-2-(1,3-dioxo-hexahydro-cyclopenta[c]pyrrol-2-yl)-2-phenyl-ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran / 1.) 0 deg C, 15 min; 2.) r.t., 1 h
2: sodium acetate / 3 h / 100 °C
View Scheme
2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

N-methylcyclopentane-1,1-dicarboximide
71099-04-2

N-methylcyclopentane-1,1-dicarboximide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 51 percent / acetonitrile / 8 h / Irradiation
View Scheme
benzylamine
100-46-9

benzylamine

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

N-benzyl-3-azabicyclo[3.3.0]octane-2,4-dione
111939-08-3

N-benzyl-3-azabicyclo[3.3.0]octane-2,4-dione

Conditions
ConditionsYield
In tetrahydrofuran for 18h; Heating / reflux;
3,5-Dichloroaniline
626-43-7

3,5-Dichloroaniline

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

C13H13Cl2NO3
1190849-68-3

C13H13Cl2NO3

Conditions
ConditionsYield
In tetrahydrofuran at 55℃;
(S)-1-(((S)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)piperidin-3-amine

(S)-1-(((S)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)piperidin-3-amine

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione
5763-49-5

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione

2-((S)-1-(((S)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)piperidin-3-yl)tetrahydrocyclopenta[c]pyrrole-1,3(2H,3aH)-dione hydrochloride

2-((S)-1-(((S)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)piperidin-3-yl)tetrahydrocyclopenta[c]pyrrole-1,3(2H,3aH)-dione hydrochloride

Conditions
ConditionsYield
Stage #1: (S)-1-(((S)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)piperidin-3-amine; 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Reflux;
Stage #2: With hydrogenchloride In water at 20℃;		0.33 g

1,2-Cyclopentanedicarboxylic anhydride Specification

The 1,2-Cyclopentanedicarboxylic anhydride , with the CAS registry number 5763-49-5, is also known as 1H-Cyclopenta[c]furan-1,3(3aH)-dione, tetrahydro-. Its EINECS number is 227-286-1. This chemical's molecular formula is C7H8O3 and molecular weight is 140.14. What's more, its systematic name is tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione.

Physical properties of 1,2-Cyclopentanedicarboxylic anhydride are: (1)ACD/LogP: -0.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.32; (4)ACD/LogD (pH 7.4): -0.32; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 15.9; (8)ACD/KOC (pH 7.4): 15.9; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 43.37 Å2; (13)Index of Refraction: 1.513; (14)Molar Refractivity: 32.2 cm3; (15)Molar Volume: 106.9 cm3; (16)Polarizability: 12.76×10-24cm3; (17)Surface Tension: 45.5 dyne/cm; (18)Density: 1.309 g/cm3; (19)Flash Point: 140.4 °C; (20)Enthalpy of Vaporization: 52.85 kJ/mol; (21)Boiling Point: 289.2 °C at 760 mmHg; (22)Vapour Pressure: 0.00223 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1OC(=O)C2CCCC12
(2)Std. InChI: InChI=1S/C7H8O3/c8-6-4-2-1-3-5(4)7(9)10-6/h4-5H,1-3H2
(3)Std. InChIKey: NMSRALOLNIBERV-UHFFFAOYSA-N

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