3-Cyclopentene-1-carboxylic acid supplier

Name
3-Cyclopentene-1-carboxylic acid
EINECS 236-047-0
CAS No. 7686-77-3
Article Data28
CAS DataBase
Density 1.189 g/cm³
Solubility
Melting Point
Formula C₆H₈O₂
Boiling Point 227.3 °C at 760 mmHg
Molecular Weight 112.128
Flash Point 101.1 °C
Transport Information
Appearance Clear colorless to slightly yellow liquid
Safety 24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 3-Cyclopentenecarboxylicacid;3-Cyclopentenylcarboxylic acid;4-Carboxycyclopentene;Cyclopent-1-ene-4-carboxylic acid;
PSA 37.30000
LogP 1.03720

Synthetic route

: 88326-51-6
Dimethyl 3-cyclopentene-1,1-dicarboxylate

: 7686-77-3
3-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
at 185 - 195℃; for 1h;	100%
at 180℃; for 1h; Neat (no solvent);	93%
at 170 - 175℃; for 2h;	89%

: 99-67-2
2-allyl-4-pentenoic acid

: 7686-77-3
3-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 40℃; for 1h; Schlenk technique;	98%

: 58101-60-3
methyl cyclopent-3-ene-1-carboxylate

: 7686-77-3
3-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
With water; lithium hydroxide In tetrahydrofuran at 25℃; for 15h;	90%

: 84646-68-4
Dimethyl 3-cyclopentene-1,1-dicarboxylate

: 7686-77-3
3-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: Dimethyl 3-cyclopentene-1,1-dicarboxylate With water; potassium hydroxide In ethanol at 45℃; for 14h; Inert atmosphere; Stage #2: at 180℃; for 1h; Inert atmosphere;	73%
Multi-step reaction with 2 steps 1: 45percent KOH / aq. ethanol / 15 h / Heating 2: 100 percent / 1 h / 185 - 195 °C View Scheme
Multi-step reaction with 2 steps 1: water; potassium hydroxide / ethanol / 1 h / Reflux 2: 1 h / 180 °C / Neat (no solvent) View Scheme

: 58101-60-3
methyl cyclopent-3-ene-1-carboxylate

: 75-05-8
acetonitrile

A: 7686-77-3
3-cyclopentene-1-carboxylic acid

B: 97820-85-4
3-(cyclopent-3-en-1-yl)-3-oxopropanenitrile

Conditions

Conditions	Yield
With potassium tert-butylate; isopropyl alcohol In 2-methyltetrahydrofuran at 20℃; for 2h; Inert atmosphere;	A n/a B 29%

...Expand

: 67886-24-2, 67886-30-0, 77983-99-4, 2348-89-2
(+/-)-cyclopent-2-enecarboxylic acid

: 74-88-4
methyl iodide

A: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 6240-43-3, 6240-44-4, 24070-68-6
cis-3-methylcyclopentanecarboxylic acid

: 4541-43-9, 5454-78-4, 18335-62-1, 97276-84-1, 109716-77-0, 109716-78-1, 134877-06-8
acide methyl-2 cyclopentanecarboxylique-1 cis

Conditions

Conditions	Yield
With pyridine; bis(1,5-cyclooctadiene)nickel (0); sulfuric acid 1) THF, room temperature, 24 h, 2) THF, room temperature, 24 h; Yield given. Multistep reaction;	A 10% B n/a C 4%

...Expand

: 124-38-9
carbon dioxide

: 1781-66-4
cyclopent-3-enyl bromide

: 7686-77-3
3-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
(i) Mg, Et2O, (ii) /BRN= 1900390/; Multistep reaction;
With magnesium 1.) ether, RT, 5 h; Yield given. Multistep reaction;

: 7686-78-4
diethyl 2-vinylcyclopropane-1,1-dicarboxylate

: 7686-77-3
3-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
Heating;
Multi-step reaction with 3 steps 1: 94 percent / 480 °C 2: KOH / H2O; ethanol / 6 h / Heating 3: 180 °C View Scheme

: 4492-41-5
cyclopent-3-ene-1-carbonitrile

: 7686-77-3
3-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide

cyclopentene-(3)-carbaldehyde-(1): cyclopentene-(3)-carbaldehyde-(1)

: 7686-77-3
3-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
With barium dihydroxide; water; silver(l) oxide
With sodium hydroxide at 350℃;

: 21622-00-4
Cyclopent-3-ene-1,1-dicarboxylic acid diethyl ester

: 7686-77-3
3-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / H2O; ethanol / 6 h / Heating 2: 180 °C View Scheme

: 14320-38-8
cyclopent-3-enol

: 7686-77-3
3-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) TsCl, Py, (ii) /BRN= 3587243/ 2: aq. NaOH View Scheme

: 3195-24-2
diallylmalonic acid diethyl ester

: 7686-77-3
3-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: water; potassium hydroxide / ethanol / 4 h / Reflux 2: neat (no solvent) / 3 h / 140 °C / Microwave irradiation 3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / 40 °C / Schlenk technique View Scheme

: 4372-31-0
2,2-diallylmalonic acid

: 7686-77-3
3-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: neat (no solvent) / 3 h / 140 °C / Microwave irradiation 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / 40 °C / Schlenk technique View Scheme

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 74-88-4
methyl iodide

: 124346-92-5
1-Methylcyclopent-3-ene-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 3-cyclopentene-1-carboxylic acid With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -30 - 25℃; for 15h; Stage #2: methyl iodide In tetrahydrofuran; n-heptane; ethylbenzene at -30 - 25℃; for 2h;	100%
Stage #1: 3-cyclopentene-1-carboxylic acid With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 20℃; for 12h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at -40 - 20℃; for 18h; Inert atmosphere;	87%
Stage #1: 3-cyclopentene-1-carboxylic acid With tert.-butyl lithium In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at -78℃;	70%

: 67-56-1
methanol

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 58101-60-3
methyl cyclopent-3-ene-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 3-cyclopentene-1-carboxylic acid With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 20℃; for 4h; Stage #2: methanol In dichloromethane	99%
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide	85%
With sulfuric acid at 0 - 80℃; for 6h;	80%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 3400-45-1
cyclopentanecarboxylic acid

Conditions

Conditions	Yield
With palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Schlenk technique; Inert atmosphere;	99%
With palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Sealed tube; Inert atmosphere; chemoselective reaction;	99%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 25125-21-7
4-(hydroxymethyl)cyclopentene

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 23℃; for 0.5h;	98%
With lithium aluminium tetrahydride In diethyl ether for 6h; Heating;	97%
With lithium aluminium tetrahydride In tetrahydrofuran at 66℃; for 6h; Reduction;	95%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 89415-65-6, 140451-75-8
(3S*,4S*)-3,4-dibromocyclopentanecarboxylic acid

Conditions

Conditions	Yield
With Oxalyl bromide; dimethyl sulfoxide In dichloromethane at -10 - 20℃; Inert atmosphere; stereoselective reaction;	96%
With hydrogen bromide; dimethyl sulfoxide In chloroform; water at 65℃; for 12h;	61%
With bromine In cyclohexane

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 248275-70-9
cyclopent-3-enecarboxylic acid methoxy-methyl-amide

Conditions

Conditions	Yield
Stage #1: 3-cyclopentene-1-carboxylic acid With 1,1'-carbonyldiimidazole In dichloromethane for 0.75h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane	96%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;	71%
Stage #1: 3-cyclopentene-1-carboxylic acid With 1,1'-carbonyldiimidazole In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Sealed tube; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere; Sealed tube;

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 74-88-4
methyl iodide

: 58101-60-3
methyl cyclopent-3-ene-1-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 16h;	96%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	96%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 16h;	96%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; Schlenk technique; Inert atmosphere;	87%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	86%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 111-27-3
hexan-1-ol

: hexyl 3-cyclopentene-1-carboxylate

Conditions

Conditions	Yield
With glucose-diphenylaminium tosylate-derived carbon solid acid (GDTCSA) In n-heptane at 80℃; for 5h;	96%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 130505-94-1
(1RS,4SR,6RS)-6-bromo-2-oxabicyclo<2.2.1>heptan-3-one

Conditions

Conditions	Yield
With trimethylsilyl bromide; N-ethyl-N,N-diisopropylamine In 1,4-dioxane; dimethyl sulfoxide for 12h; Heating;	95%
With trimethylsilyl bromide; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In chloroform for 12h; Heating;	40%
With trimethylsilyl bromide; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In chloroform for 12h; Heating;	40%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 100-39-0
benzyl bromide

: 130762-09-3
benzyl cyclopent‐3‐ene‐1‐carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 2h;	95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	94%
With tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate In dichloromethane; water at 20℃; for 16h;	70%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 22393-62-0
BnBr

: 130762-09-3
benzyl cyclopent‐3‐ene‐1‐carboxylate

Conditions

Conditions	Yield
With potassium carbonate In [(2)H6]acetone; ethyl acetate; Petroleum ether	95%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 129413-75-8, 138847-69-5
(E)-(5-bromopent-3-en-1-yl)benzene

: (E)-1-(5-phenylpent-2-en-1-yl)cyclopent-3-ene-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 3-cyclopentene-1-carboxylic acid With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #2: (E)-(5-bromopent-3-en-1-yl)benzene In tetrahydrofuran; hexane at -40 - 20℃; Inert atmosphere;	92%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 147221-33-8
1-methyl-1-phenylethyl 2,2,2-trichloroacetimidoate

: 1105703-39-6
2-phenylpropan-2-yl cyclopent-3-enecarboxylate

Conditions

Conditions	Yield
In dichloromethane; cyclohexane at 20℃; for 16h;	90%

: 64-17-5
ethanol

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 21622-01-5
ethyl 3-cyclopentene-1-carboxylate

Conditions

Conditions	Yield
With thionyl chloride at 5 - 20℃; for 1.5h;	89.42%
With thionyl chloride at 5 - 20℃; for 0.5h;	84%
With thionyl chloride at -10℃; for 4h; Inert atmosphere; Schlenk technique; Reflux;	80%
With thionyl chloride at 0 - 20℃;	54%
With thionyl chloride at 10 - 35℃;

: 1458-98-6
2-methyl-3-bromo-1-propene

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 1-(2-methylallyl)cyclopent-3-ene-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 3-cyclopentene-1-carboxylic acid With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #2: 2-methyl-3-bromo-1-propene In tetrahydrofuran; hexane at -40 - 20℃; Inert atmosphere;	89%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 3-amino-6-bromo-isothiazolo[4,3-b]pyridine

: N-(6-bromo-isothiazolo[4,3-b]pyridin-3-yl)cyclopent-3-enecarboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	89%

: 6940-76-7
1-iodo-3-chloro-propane

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 1-(3-chloropropyl)cyclopent-3-ene-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 3-cyclopentene-1-carboxylic acid With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -10 - 20℃; for 2h; Inert atmosphere; Stage #2: 1-iodo-3-chloro-propane In tetrahydrofuran at -10 - 0℃; for 0.5h; Inert atmosphere;	89%
Stage #1: 3-cyclopentene-1-carboxylic acid With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -20 - 20℃; Stage #2: 1-iodo-3-chloro-propane In tetrahydrofuran; hexane at -20 - 20℃;

: 1592-38-7
2-Naphthalenemethanol

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: naphthalen-2-ylmethyl cyclopent-3-enecarboxylate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;	88%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 62-53-3
aniline

: 7686-79-5
3-cyclopentenecarboxylic acid phenyl amide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	87%
Stage #1: 3-cyclopentene-1-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h; Stage #2: aniline With dmap In dichloromethane at 20℃; for 16h;

N-hydroxyphthalimide: N-hydroxyphthalimide

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 1,3-dioxoisoindolin-2-yl cyclopent-3-ene-1-carboxylate

Conditions

Conditions	Yield
With dmap; diisopropyl-carbodiimide In DClO4 for 12h; Inert atmosphere;	86%
With dmap; diisopropyl-carbodiimide In dichloromethane for 1h;	60%
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;	46%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 3744-80-7
cyclopent-3-ene-1-carboxylic acid chloride

Conditions

Conditions	Yield
With thionyl chloride Heating;	85%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 5h; Chlorination;	80%
With thionyl chloride

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: trans-3,4-dichlorocyclopentanecarboxylic acid

Conditions

Conditions	Yield
With oxalyl dichloride; 1,1'-sulfinylbisbenzene In dichloromethane at -78 - 20℃; for 1h; Inert atmosphere;	85%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 115-11-7
isobutene

: 84694-13-3
tert-butyl cyclopent-3-ene-1-carboxylate

Conditions

Conditions	Yield
With sulfuric acid In diethyl ether for 96h; Ambient temperature;	84%
With sulfuric acid In diethyl ether at -78 - 20℃; for 96h; Sealed tube;	16.98 g

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 108-00-9
N,N-dimethylethylenediamine

: C10H17NO2

Conditions

Conditions	Yield
Stage #1: 3-cyclopentene-1-carboxylic acid With 4-methyl-morpholine In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: With isobutyl chloroformate In tetrahydrofuran for 0.25h; Stage #3: N,N-dimethylethylenediamine In tetrahydrofuran for 2h;	84%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 75-65-0
tert-butyl alcohol

: 84694-13-3
tert-butyl cyclopent-3-ene-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 3-cyclopentene-1-carboxylic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 5 - 20℃; Stage #2: tert-butyl alcohol With triethylamine In dichloromethane at 5 - 20℃;	83%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 103-69-5
N-ethyl-N-phenylamine

: N-ethyl-N-phenylcyclopent-3-ene-1-carboxamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;	83%

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 67-63-0
isopropyl alcohol

: isopropyl cyclopent-3-ene-1-carboxylate

Conditions

Conditions	Yield
With thionyl chloride at 0℃; for 5h; Inert atmosphere; Reflux;	82%

3-Cyclopentene-1-carboxylic acid Chemical Properties

Product Name: 3-Cyclopentene-1-carboxylic acid (CAS NO.7686-77-3)

Molecular Formula: C₆H₈O₂
Molecular Weight: 112.13g/mol
Mol File: 7686-77-3.mol
Boiling point: 227.3 °C at 760 mmHg
Storage Temperature: Refrigerator (+4°C)
Flash Point: 101.1 °C
Density: 1.189 g/cm³
Refractive index: n20/D 1.469(lit.)
Index of Refraction: 1.522
Molar Refractivity: 28.76 cm³
Molar Volume: 94.2 cm³
Surface Tension: 48.2 dyne/cm
Enthalpy of Vaporization: 51.1 kJ/mol
Vapour Pressure: 0.0282 mmHg at 25°C
XLogP3-AA: 0.9
H-Bond Donor: 1
H-Bond Acceptor: 2
Structure Descriptors of 3-Cyclopentene-1-carboxylic acid (CAS NO.7686-77-3):
IUPAC Name: cyclopent-3-ene-1-carboxylic acid
Canonical SMILES: C1C=CCC1C(=O)O
InChI: InChI=1S/C6H8O2/c7-6(8)5-3-1-2-4-5/h1-2,5H,3-4H2,(H,7,8)
InChIKey: XVSYDLITVYBCBD-UHFFFAOYSA-N
Product Categories: ACIDHALIDE; pharmacetical; INTERMEDIATESOFDOLASETRONMESYLATE; Carboxylic Acids; Organic acids; API intermediates; Carboxylic Acids; Ring Systems; C6; Carbonyl Compounds

3-Cyclopentene-1-carboxylic acid Safety Profile

Safety Information of 3-Cyclopentene-1-carboxylic acid (CAS NO.7686-77-3):
Hazard Codes Xi Irritant
Risk Statements 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 24/25-36-26
S24/25:Avoid contact with skin and eyes.
S36:Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany 3
Hazard Note Irritant

3-Cyclopentene-1-carboxylic acid Specification

3-Cyclopentene-1-carboxylic acid , its CAS NO. is 7686-77-3, the synonyms are 3-Cyclopentenecarboxylic acid ; Cyclopentene-1-CarboxylicAcid ; 3-Cyclopentenecarboxylic .

Product Name

3-Cyclopentene-1-carboxylic acid

Synthetic route

3-Cyclopentene-1-carboxylic acid Chemical Properties

3-Cyclopentene-1-carboxylic acid Safety Profile

3-Cyclopentene-1-carboxylic acid Specification

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