1,2-Cyclopentanedicarboxylicacid, (1R,2S)-rel- supplier

Name
CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID
EINECS
CAS No. 1461-96-7
Article Data28
CAS DataBase
Density 1.396 g/cm³
Solubility
Melting Point 132-136℃
Formula C₇H₁₀O₄
Boiling Point 378.6 °C at 760 mmHg
Molecular Weight 158.154
Flash Point 196.9 °C
Transport Information
Appearance
Safety 26
Risk Codes 36/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1,2-Cyclopentanedicarboxylicacid, cis- (8CI,9CI);1,2-cis-Cyclopentanedicarboxylic acid;cis-1,2-Cyclopentanedicarboxylic acid;
PSA 74.60000
LogP 0.57190

Synthetic route

: 1655-07-8
ethyl 2-oxocyclohexane carboxylate

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

Conditions

Conditions	Yield
Stage #1: ethyl 2-oxocyclohexane carboxylate In chloroform at 0 - 20℃; Stage #2: With potassium hydroxide In water at 0 - 20℃; Favorskii rearrangement;	74%
Stage #1: ethyl 2-oxocyclohexane carboxylate With bromine In chloroform at 0 - 20℃; Stage #2: With potassium hydroxide In water at 0℃; for 6h; Stage #3: With hydrogenchloride In water pH=5;	63%
Multi-step reaction with 2 steps 1: Br2 / CH2Cl2 2: aq. KOH; aq. HCl View Scheme

: 30132-23-1
ethyl 3-bromo-2-oxocyclohexanecarboxylate

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

Conditions

Conditions	Yield
With potassium hydroxide Favorskii rearrangement;	73%
With hydrogenchloride; potassium hydroxide
Multi-step reaction with 2 steps 1: aq. NaOH / ethanol 2: (i) AcCl, (ii) OH- View Scheme

: 79692-84-5
2,4-dimethoxybicyclo<3.2.1>octane

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

Conditions

Conditions	Yield
	54%

: 3128-15-2
cyclopent-1-ene-1,2-dicarboxylic acid

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

Conditions

Conditions	Yield
With platinum Hydrogenation;

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

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

Conditions

Conditions	Yield
With acetic anhydride Loesen in Wasser oder in Kalilauge und Ansaeuern;
(i) AcCl, (ii) OH-; Multistep reaction;
Multi-step reaction with 2 steps 1: 1.5 h / 200 °C 2: H2O / Heating View Scheme

: 62732-15-4
cis-1,2-divinylcyclopentane

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

Conditions

Conditions	Yield
(i) O3, AcOH, (ii) aq. H2O2; Multistep reaction;

: 19042-30-9
exo-cis-6,7-Dihydroxy-cis-bicyclo<3,2,0>heptan

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

Conditions

Conditions	Yield
With potassium dichromate; sulfuric acid at 15 - 20℃; for 1h;

: 35878-28-5, 743438-34-8
cyclopentane-cis-1,2-dicarboxylic acid anhydride

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

Conditions

Conditions	Yield
With water Heating;

: 124-38-9
carbon dioxide

: 201230-82-2
carbon monoxide

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

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); (c-C6H11)2PCH2CH2-2-pyridyl; sulfuric acid 1) THF, 20 deg C, 48 h, 2) THF, room temperature, 10 h; Yield given. Multistep reaction;

: 118577-36-9
ethyl 5-bromo-2-oxocyclohexanecarboxylate

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

Conditions

Conditions	Yield
With potassium hydroxide at 0℃; for 2h; Yield given;

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

KOH-solution: KOH-solution

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

Conditions

Conditions	Yield
durch Ansaeuern; anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2);

(+-)-cis-bicyclo<3.2.0>heptan-6-one: (+-)-cis-bicyclo<3.2.0>heptan-6-one

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

Conditions

Conditions	Yield
With nitric acid

1-cyano-cyclopentane-dicarboxylic acid-(1.2)-diethyl ester: 1-cyano-cyclopentane-dicarboxylic acid-(1.2)-diethyl ester

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

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

Conditions

Conditions	Yield
With hydrogenchloride Isolierung ueber das Anhydrid;

: 13756-54-2
rac-bicyclo[3.2.0]hept-2-en-6-one

: 7697-37-2
nitric acid

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

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

...Expand

: 7647-01-0
hydrogenchloride

: 143102-48-1
Ethyl 1-cyanocyclopentane-1,2-dicarboxylate

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

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

Conditions

Conditions	Yield
optically inactive substance of bp 3.5: 135-136deg;

...Expand

: 50708-47-9
1,1,2,2-Cyclopentantetracarbonsaeure-tetraethylester

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: glacial acetic acid; concentrated sulfuric acid; water 2: acetic acid anhydride / Loesen in Wasser oder in Kalilauge und Ansaeuern View Scheme

: 91972-94-0
cis-1,2-Cyclopentan-diessigsaeure-bis-dimethylamid

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 2: (i) aq. H2O2, (ii) (thermolysis) 3: (i) O3, AcOH, (ii) aq. H2O2 View Scheme

: 95259-54-4
(cis-cyclopentane-1,2-diyl)-di-acetic acid

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: (i) SOCl2, (ii) /BRN= 605257/ 2: LiAlH4 3: (i) aq. H2O2, (ii) (thermolysis) 4: (i) O3, AcOH, (ii) aq. H2O2 View Scheme

: 104282-33-9
cis-1.2-Bis-<2-dimethylamino-ethyl>-cyclopentan

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) aq. H2O2, (ii) (thermolysis) 2: (i) O3, AcOH, (ii) aq. H2O2 View Scheme

: (3aR,3bS,6aR,6bS)-Hexahydro-1,3-dioxa-cyclobutadicyclopenten-2-one

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH / 2 h / 60 °C 2: K2Cr2O7, H2SO4 / 1 h / 15 - 20 °C View Scheme

cis-1,2-cyclopentanecarboxylic acid: cis-1,2-cyclopentanecarboxylic acid

: 3128-15-2
cyclopent-1-ene-1,2-dicarboxylic acid

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

Conditions

Conditions	Yield
With hydrogen; aluminum nickel In phosphorus pentaoxide; ethanol

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

: 35878-28-5, 743438-34-8
cyclopentane-cis-1,2-dicarboxylic acid anhydride

Conditions

Conditions	Yield
With acetic anhydride for 20h; Reflux;	89%
With acetic anhydride for 10h; Heating;	85%
With acetic anhydride for 20h; Heating;	81%

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

: 75658-83-2
cis-1,2-bis(hydroxymethyl)cyclopentane

Conditions

Conditions	Yield
With lithium aluminium tetrahydride	65%
With lithium aluminium tetrahydride In diethyl ether
With Trimethyl borate; dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃;
Multi-step reaction with 2 steps 1: 220 °C 2: LiAlH4 View Scheme
Multi-step reaction with 2 steps 1: diethyl ether 2: LiAlH4 View Scheme

: 186581-53-3, 908094-01-9
diazomethane

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

: 4841-91-2
dimethyl cis-1,2-cyclopentanedicarboxylate

Conditions

Conditions	Yield
With diethyl ether
In methanol

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

: 63243-23-2, 933775-94-1
cis-hexahydro-cyclopentimidazol-2-one

Conditions

Conditions	Yield
With chloroform; tris-(2-chloro-ethyl)-amine; sulfuric acid anschliessendes Erhitzen mit wss. HCl und Behandeln des Reaktionsprodukts in wss. KOH mit COCl2 in Toluol;

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

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

Conditions

Conditions	Yield
With hydrogenchloride at 180℃;

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

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

Conditions

Conditions	Yield
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;

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

: 5763-49-5, 35878-28-5, 147148-10-5
cis-cyclopentane-1,2-dicarboxylic acid-anhydride

Conditions

Conditions	Yield
With acetic anhydride

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

: 13195-85-2
cis-Cyclopentan-1,2-dicarbamid

Conditions

Conditions	Yield
(i) SOCl2, (ii) aq. NH3; Multistep reaction;

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

: 4380-96-5
[5-(thiophen-2-yl)thiophen-2-yl]methanamine

: (1R,2S)-2-[([2,2']Bithiophenyl-5-ylmethyl)-carbamoyl]-cyclopentanecarboxylic acid

Conditions

Conditions	Yield
Stage #1: cis-1,2-cyclopentanedicarboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran Stage #2: [5-(thiophen-2-yl)thiophen-2-yl]methanamine In tetrahydrofuran

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

: methyl (3aS,7aS)-6-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-5-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: borane dimethyl sulfide complex; trimethylborate / tetrahydrofuran / 0 - 20 °C 2.1: phosphorus tribromide / -10 - 85 °C 3.1: ethanol / 100 °C 4.1: DOWEX 550A (OH), activated / H2O 5.1: 130 - 200 °C / 200 Torr 6.1: 99 percent / benzene / 48 h / 20 °C 7.1: H2 / PtO2 / tetrahydrofuran / 20 °C / 760 Torr 8.1: hydroquinidine (anthraquinone-1,4-diyl) diether / diethyl ether / 72 h / -18 °C 9.1: oxalyl chloride / toluene / 20 °C 10.1: H2; 2,6-lutidine / Pd/C / tetrahydrofuran / 20 °C / 2068.59 Torr 11.1: triethylamine-zinc chloride complex / benzene / 20 - 40 °C 12.1: O3 / methanol; CH2Cl2 / -7 °C 13.1: PhSeCl; pyridine / CH2Cl2 / 0.5 h / 0 °C 13.2: 48 percent / aq. H2O2 / CH2Cl2 / 0.5 h / 0 °C View Scheme

Yield

Multi-step reaction with 13 steps
1.1: borane dimethyl sulfide complex; trimethylborate / tetrahydrofuran / 0 - 20 °C
2.1: phosphorus tribromide / -10 - 85 °C
3.1: ethanol / 100 °C
4.1: DOWEX 550A (OH), activated / H2O
5.1: 130 - 200 °C / 200 Torr
6.1: 99 percent / benzene / 48 h / 20 °C
7.1: H2 / PtO2 / tetrahydrofuran / 20 °C / 760 Torr
8.1: hydroquinidine (anthraquinone-1,4-diyl) diether / diethyl ether / 72 h / -18 °C
9.1: oxalyl chloride / toluene / 20 °C
10.1: H2; 2,6-lutidine / Pd/C / tetrahydrofuran / 20 °C / 2068.59 Torr
11.1: triethylamine-zinc chloride complex / benzene / 20 - 40 °C
12.1: O3 / methanol; CH2Cl2 / -7 °C
13.1: PhSeCl; pyridine / CH2Cl2 / 0.5 h / 0 °C
13.2: 48 percent / aq. H2O2 / CH2Cl2 / 0.5 h / 0 °C
View Scheme

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

: 932698-05-0
6-formyl-octahydro-indene-5-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: borane dimethyl sulfide complex; trimethylborate / tetrahydrofuran / 0 - 20 °C 2: phosphorus tribromide / -10 - 85 °C 3: ethanol / 100 °C 4: DOWEX 550A (OH), activated / H2O 5: 130 - 200 °C / 200 Torr 6: 99 percent / benzene / 48 h / 20 °C 7: H2 / PtO2 / tetrahydrofuran / 20 °C / 760 Torr 8: hydroquinidine (anthraquinone-1,4-diyl) diether / diethyl ether / 72 h / -18 °C 9: oxalyl chloride / toluene / 20 °C 10: H2; 2,6-lutidine / Pd/C / tetrahydrofuran / 20 °C / 2068.59 Torr View Scheme

Yield

Multi-step reaction with 10 steps
1: borane dimethyl sulfide complex; trimethylborate / tetrahydrofuran / 0 - 20 °C
2: phosphorus tribromide / -10 - 85 °C
3: ethanol / 100 °C
4: DOWEX 550A (OH), activated / H2O
5: 130 - 200 °C / 200 Torr
6: 99 percent / benzene / 48 h / 20 °C
7: H2 / PtO2 / tetrahydrofuran / 20 °C / 760 Torr
8: hydroquinidine (anthraquinone-1,4-diyl) diether / diethyl ether / 72 h / -18 °C
9: oxalyl chloride / toluene / 20 °C
10: H2; 2,6-lutidine / Pd/C / tetrahydrofuran / 20 °C / 2068.59 Torr
View Scheme

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

: 926644-62-4
6-oxo-octahydro-indene-5-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: borane dimethyl sulfide complex; trimethylborate / tetrahydrofuran / 0 - 20 °C 2: phosphorus tribromide / -10 - 85 °C 3: ethanol / 100 °C 4: DOWEX 550A (OH), activated / H2O 5: 130 - 200 °C / 200 Torr 6: 99 percent / benzene / 48 h / 20 °C 7: H2 / PtO2 / tetrahydrofuran / 20 °C / 760 Torr 8: hydroquinidine (anthraquinone-1,4-diyl) diether / diethyl ether / 72 h / -18 °C 9: oxalyl chloride / toluene / 20 °C 10: H2; 2,6-lutidine / Pd/C / tetrahydrofuran / 20 °C / 2068.59 Torr 11: triethylamine-zinc chloride complex / benzene / 20 - 40 °C 12: O3 / methanol; CH2Cl2 / -7 °C View Scheme

Yield

Multi-step reaction with 12 steps
1: borane dimethyl sulfide complex; trimethylborate / tetrahydrofuran / 0 - 20 °C
2: phosphorus tribromide / -10 - 85 °C
3: ethanol / 100 °C
4: DOWEX 550A (OH), activated / H2O
5: 130 - 200 °C / 200 Torr
6: 99 percent / benzene / 48 h / 20 °C
7: H2 / PtO2 / tetrahydrofuran / 20 °C / 760 Torr
8: hydroquinidine (anthraquinone-1,4-diyl) diether / diethyl ether / 72 h / -18 °C
9: oxalyl chloride / toluene / 20 °C
10: H2; 2,6-lutidine / Pd/C / tetrahydrofuran / 20 °C / 2068.59 Torr
11: triethylamine-zinc chloride complex / benzene / 20 - 40 °C
12: O3 / methanol; CH2Cl2 / -7 °C
View Scheme

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

: 932698-11-8
octahydro-2-oxa-s-indacene-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: borane dimethyl sulfide complex; trimethylborate / tetrahydrofuran / 0 - 20 °C 2: phosphorus tribromide / -10 - 85 °C 3: ethanol / 100 °C 4: DOWEX 550A (OH), activated / H2O 5: 130 - 200 °C / 200 Torr 6: 99 percent / benzene / 48 h / 20 °C 7: H2 / PtO2 / tetrahydrofuran / 20 °C / 760 Torr View Scheme

1,2-Cyclopentanedicarboxylicacid, (1R,2S)-rel- Specification

This chemical is called 1,2-Cyclopentanedicarboxylicacid, (1R,2S)-rel-, and its IUPAC name is (1R,2S)-cyclopentane-1,2-dicarboxylic acid. With the molecular formula of C₇H₁₀O₄, its molecular weight is 158.15. The CAS registry number of this chemical is 1461-96-7.

Other characteristics of the 1,2-Cyclopentanedicarboxylicacid, (1R,2S)-rel- can be summarised as followings: (1)ACD/LogP: 0.07; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 4; (8)#H bond donors: 2; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 52.6 Å²; (11)Index of Refraction: 1.535; (12)Molar Refractivity: 35.27 cm³; (13)Molar Volume: 113.2 cm³; (14)Polarizability: 13.98×10^-24cm³; (15)Surface Tension: 64.6 dyne/cm; (16)Density: 1.396 g/cm³; (17)Flash Point: 196.9 °C; (18)Enthalpy of Vaporization: 68.79 kJ/mol; (19)Boiling Point: 378.6 °C at 760 mmHg; (20)Vapour Pressure: 8.88E-07 mmHg at 25°C.

You can still convert the following datas into molecular structure:
1.SMILES: O=C(O)[C@@H]1CCC[C@@H]1C(=O)O
2.InChI: InChI=1/C7H10O4/c8-6(9)4-2-1-3-5(4)7(10)11/h4-5H,1-3H2,(H,8,9)(H,10,11)/t4-,5+
3.InChIKey: ASJCSAKCMTWGAH-SYDPRGILBZ

Product Name

CIS-CYCLOPENTANE-1,2-DICARBOXYLIC ACID

Synthetic route

1,2-Cyclopentanedicarboxylicacid, (1R,2S)-rel- Specification

Related Products

Hot Products