77-55-4

Basic information

• Product Name: 1-Phenylcyclopentanecarboxylic acid
• Synonyms: RARECHEM AL BO 1511;PHENYLCYCLOPENTANECARBOXYLIC ACID;AKOS BC-0226;1-PHENYL-1-CYCLOPENTANECARBOXYLIC ACID;1-PHENYLCYCLOPENTANE-1-CARBOXYLIC ACID;1-PHENYLCYCLOPENTANECARBOXYLIC ACID;ASISCHEM D50957;1-Phenyl-1-cyclopentanecarboxylic acid 99%
• CAS NO: 77-55-4
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.24
• EINECS: 201-037-7
• Product Categories: C11 to C12;Carbonyl Compounds;Carboxylic Acids
• Mol File: 77-55-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 159-161 °C(lit.)
• Boiling Point: 285.75°C (rough estimate)
• Flash Point: 157.1 °C
• Appearance: Cream to gray-brown/Powder
• Density: 1.0486 (rough estimate)
• Vapor Pressure: 3.73E-05mmHg at 25°C
• Refractive Index: 1.4970 (estimate)
• Storage Temp.: 2-8°C
• Solubility: slightly sol. in Methanol
• PKA: 4.39±0.20(Predicted)
• BRN: 1638653
• CAS DataBase Reference: 1-Phenylcyclopentanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenylcyclopentanecarboxylic acid(77-55-4)
• EPA Substance Registry System: 1-Phenylcyclopentanecarboxylic acid(77-55-4)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38-34
• Safety Statements: 37/39-26-45-36/37/39-27
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 77-55-4(Hazardous Substances Data)

Usage

Chemical Properties

CREAM TO GREY-BROWN POWDER

Uses

1-Phenyl-1-cyclopentanecarboxylic acid was used to prepare precursors required for solid phase synthesis of isoxazole and isoxazoline derivatives.

InChI:InChI=1/C12H14O2/c13-11(14)12(8-4-5-9-12)10-6-2-1-3-7-10/h1-3,6-7H,4-5,8-9H2,(H,13,14)/p-1

Synthetic route

2-allyl-2-phenylpent-4-enoic acid → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
Stage #1: 2-allyl-2-phenylpent-4-enoic acid With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In tetrahydrofuran at 40℃; for 0.5h; Inert atmosphere; Stage #2: With formic acid; sodium hydride In tetrahydrofuran at 80℃; for 24h; Inert atmosphere;	97%

C13H14O2 → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
With dihydrogen peroxide In water; ethyl acetate at 20℃; for 12h; Green chemistry; regioselective reaction;	92%
With dihydrogen peroxide In ethyl acetate at 20℃; regioselective reaction;	92%

1-phenyl-1-cyclopentanecarboxaldehyde (21573-69-3) → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
With potassium sulfite; copper(l) chloride; potassium bromide In cyclohexane at 160℃; for 8h; Temperature;	91%
With silver(l) oxide

1-phenyl-1-cyclopentanecarbonitrile (77-57-6) → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
With potassium hydroxide In ethanol for 96h; Heating;	68%
With sulfuric acid
With potassium hydroxide at 200℃;

1-phenyl-N-(quinolin-8-yl)cyclopentanecarboxamide (908520-36-5) → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
Stage #1: 1-phenyl-N-(quinolin-8-yl)cyclopentanecarboxamide With ozone In dichloromethane at -78℃; Inert atmosphere; Stage #2: With lithium hydroxide monohydrate; dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 48h; Inert atmosphere;	53%

1,4-dibromo-butane (110-52-1) + t-butyl phenylacetate (16537-09-0) → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
(i) aq. NaOH, Cl, DMSO, (ii) aq. H2SO4, AcOH; Multistep reaction;

formic acid (64-18-6) + 1-phenylcyclopentanol (10487-96-4) → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
With sulfuric acid at 20 - 25℃; for 2h;

1-Methyl-1-(1-phenyl-cyclopentanecarbonyloxymethyl)-pyrrolidinium; chloride → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
In water at 37℃; Rate constant; pH 7.4;

1,4-dibromo-butane (110-52-1) + diethyl ether (60-29-7) + sodium compound of phenylacetonitrile → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) + amide of 1-phenyl-cyclopentane-carboxylic acid-(1)

Conditions	Yield
und folgender Hydrolyse des Reaktionsprodukts mit alkoh.KOH;

1,4-dibromo-butane (110-52-1) + sodium-compound of phenylacetonitrile → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) + 1-phenyl-cyclopentane-carboxylic acid-(1)-amide

Conditions	Yield
With diethyl ether Behandeln des Reaktionsprodukts mit aethanol. Kalilauge;

phenylacetonitrile (140-29-4) → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaNH2 2: methanol. KOH / 200 °C View Scheme
Multi-step reaction with 2 steps 1: NaOH 2: aqueous KOH / 130 - 140 °C View Scheme
Multi-step reaction with 2 steps 1: NaNH2 2: KOH; diethylene glycol / 190 °C View Scheme

phenylacetonitrile (140-29-4) + n-butyl halide → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: liq. NH3, NaNH2 2: KOH / bis-(2-hydroxy-ethyl) ether View Scheme
Multi-step reaction with 2 steps 1: NaNH2 2: (acid hydrolysis) View Scheme

2-(hydroxymethylene)cyclohexanone (823-45-0) → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: toluene / 0.17 h / 20 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere 2.1: dihydrogen peroxide / ethyl acetate; water / 12 h / 20 °C / Green chemistry View Scheme

cyclohexanone (108-94-1) → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / mineral oil; methanol; toluene / 12 h / 0 - 20 °C / Inert atmosphere 2.1: toluene / 0.17 h / 20 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere 3.1: dihydrogen peroxide / ethyl acetate; water / 12 h / 20 °C / Green chemistry View Scheme

benzeneacetic acid methyl ester (101-41-7) → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium iodide; sodium hydride / tetrahydrofuran 2.1: sodium hydroxide; water / ethanol / 90 °C 3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / tetrahydrofuran / 0.5 h / 40 °C / Inert atmosphere 3.2: 24 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C 1.2: 1,4-halobutane / 18.17 h / 0 - 50 °C 2.1: sodium hydroxide / methanol; water / 3 h / Reflux View Scheme

methyl 2-phenyl-2-(prop-2-enyl)pent-4-enoate (242482-24-2) → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / ethanol / 90 °C 2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / tetrahydrofuran / 0.5 h / 40 °C / Inert atmosphere 2.2: 24 h / 80 °C / Inert atmosphere View Scheme

1-phenyl-1-cyclopentanecarboxylic acid methyl ester (4535-96-0) → 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4)

Conditions	Yield
With sodium hydroxide In methanol; water for 3h; Reflux;

diazomethane (186581-53-3, 908094-01-9) + 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → 1-phenyl-1-cyclopentanecarboxylic acid methyl ester (4535-96-0)

Conditions	Yield
In diethyl ether at 20℃; for 24h;	98%

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) + potassium phenyltrifluoborate → C18H18O2

Conditions	Yield
With dipotassium hydrogenphosphate; oxygen; palladium diacetate; p-benzoquinone In tetr-butanol at 100℃; under 22801.5 Torr; for 48h;	98%

methanol (67-56-1) + 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → 1-phenyl-1-cyclopentanecarboxylic acid methyl ester (4535-96-0)

Conditions	Yield
With thionyl chloride at 20℃; for 17h; Cooling with ice; Inert atmosphere;	97%
With hydrogenchloride for 2h; Heating;	88%
sulfuric acid Heating / reflux;

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) + phenyl(2,4,6-triisopropylphenyl)iodonium trifluoromethanesulfonate (312727-69-8) → 2,4,6-triisopropylphenyl 1-phenylcyclopentane-1-carboxylate

Conditions	Yield
With potassium tert-butylate In toluene at 0℃; for 1.25h; Reflux;	94%

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → 1-hydroxymethyl-1-phenylcyclopentane (59115-90-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 18h; Reflux;	93%
With borane-THF In tetrahydrofuran for 2h; Ambient temperature;	75%
Multi-step reaction with 2 steps 1: 88 percent / HCl / 2 h / Heating 2: 88 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

N-(3-phenylpropyl)-6-amino-4a-(3-methoxyphenyl)-8a-methyloctahydroisoquinoline + 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → 1-phenylcyclopentanecarboxylic acid [4a-(3-methoxyphenyl)-8a-methyl-2-(3-phenylpropyl)octahydroisoquinolin-6-yl]amide

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran at 20℃; for 2h;	92%

tert-butyl (1S,4R,5R,7S)-7-amino-5-(3-isopropoxyphenyl)-4-methyl-2-azabicyclo[3.3.1]nonane-2-carboxylate (911422-98-5) + 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → tert-butyl (1S,4R,5R,7S)-5-(3-isopropoxyphenyl)-4-methyl-7-{[(1-phenyl-1-cyclopentyl)carbonyl]amino}-2-azabicyclo[3.3.1]nonane-2-carboxylate (911423-02-4)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran at 20℃; for 4h;	92%

cis-N-(3-phenylpropyl)-6-amino-4a-(3-methoxyphenyl)-8a-methyloctahydroisoquinoline + 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → 1-phenylcyclopentanecarboxylic acid cis-[4a-(3-methoxyphenyl)-8a-methyl-2-(3-phenylpropyl)octahydroisoquinolin-6-yl]amide

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran at 20℃; for 2h;	92%

phenylglyoxylic acid ethyl ester (1603-79-8) + 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → ethyl 2-hydroxy-2-phenyl-2-(1-phenylcyclopentyl)acetate

Conditions	Yield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate In dimethyl sulfoxide at 40℃; for 1h; Glovebox; Inert atmosphere; Irradiation;	91%

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → 1-(4-iodophenyl)cyclopentanecarboxylic acid (135569-28-7)

Conditions	Yield
With sodium iodate; sulfuric acid; iodine at 20 - 70℃; for 72h;	89%

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → 1-(4-nitro-phenyl)-cyclopentanecarboxylic acid (52648-77-8)

Conditions	Yield
With sulfuric acid; nitric acid at 0 - 20℃; for 3h;	87%
With sulfuric acid; nitric acid In acetic anhydride at 10℃; for 3h; Yield given;

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) + phenethylamine (64-04-0) → N-phenethyl-1-phenylcyclopentane-1-carboxamide

Conditions	Yield
With C36H24B4N2O3 In toluene at 80℃; for 14h; Molecular sieve;	86%
With oxygen; potassium carbonate; eosin y In toluene at 20℃; Irradiation; Green chemistry;	86%

4-ethoxycarbonylpyrazole (37622-90-5) + 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → ethyl 1-(1-phenylcyclopentyl)-1H-pyrazole-4-carboxylate

Conditions	Yield
With 2,4,6-trimethyl-pyridine; tert-butylammonium hexafluorophosphate(V) In dichloromethane for 2.5h; Molecular sieve; Electrochemical reaction;	86%

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → cyclopentylbenzene (700-88-9)

Conditions	Yield
With 2,6-dimethylpyridine; 4,4'-dichlorodiphenyl disulfide; 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate In 1,2-dichloro-ethane at 20℃; for 14h; Irradiation; Inert atmosphere;	82%

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) + 4-methoxycarbonylphenyl bromide (619-42-1) → methyl 4-((1-phenylcyclopentane-1-carbonyl)oxy)benzoate

Conditions	Yield
With nickel(II) bromide dimethoxyethane; 4,4'-Dimethoxy-2,2'-bipyridin; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl acetamide at 20℃; for 10h; Inert atmosphere; Glovebox; Electrolysis;	82%

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) + carbon monoxide (201230-82-2) → 1-(2-carboxyphenyl)cyclopentanecarboxylic acid (41058-64-4)

Conditions	Yield
With dipotassium hydrogenphosphate; sodium acetate; palladium diacetate; silver carbonate In 1,4-dioxane at 150℃; under 760.051 Torr; for 18h;	80%

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) + 9-(3-amino-3,5-dideoxy-β-D-xylofuranosyl)-N6-cyclopentyladenine (423774-22-5) → 9-(3,5-dideoxy-3-{[(1-phenylcyclopentyl)carbonyl]amino}-β-D-xylofuranosyl)-N6-cyclopentyladenine

Conditions	Yield
With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane at 20℃; for 2h;	79%

(+)-(1S,4R,5R,7S)-5-(3-isopropoxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]nonan-7-amine + 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → N-[(1S,4R,5R,7S)-5-(3-isopropoxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]non-7-yl]-1-phenylcyclopentanecarboxamide

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran at 20℃;	78%

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) + 4-methylphenyl methylsulfide (623-13-2) → (p-tolylthio)methyl 1-phenylcyclopentane-1-carboxylate

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In methanol; acetonitrile at 20℃; for 6h; Inert atmosphere; Electrochemical reaction;	77%

8-amino quinoline (578-66-5) + 1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → 1-phenyl-N-(quinolin-8-yl)cyclopentanecarboxamide (908520-36-5)

Conditions	Yield
With thionyl chloride; oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Schlenk technique;	76%

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → spiro-2-one

Conditions	Yield
With [bis(acetoxy)iodo]benzene; potassium acetate; palladium diacetate; N-acetylglycine In tert-butyl alcohol at 100℃; for 12h; Solvent; Reagent/catalyst; Temperature; Time; Sealed tube;	69%

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) + 6-(1-methyl-1H-pyrazol-4-yl)-4-(6-(piperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile dihydrochloride → 6-(1-methyl-1H-pyrazol-4-yl)-4-(6-(4-(1-phenylcyclopentanecarbonyl)piperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile

Conditions

Yield

Stage #1: 1-phenyl-1-cyclopentanecarboxylic acid With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl acetamide at 20℃; for 0.416667h; Stage #2: 6-(1-methyl-1H-pyrazol-4-yl)-4-(6-(piperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile dihydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide

68%

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) + methyllithium (917-54-4) → 1-(1-phenylcyclopentyl)ethan-1-one (4046-09-7)

Conditions	Yield
In diethyl ether 1.) 0 deg C; 2.) 2 h, reflux;	67%
In diethyl ether Heating;

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) → 1,1'-Diphenyl-1,1'-bicyclopentyl (59358-70-2)

Conditions	Yield
With C44H32N4(2+)*2F6P(1-); sodium hydroxide In water; acetonitrile at 20℃; for 18h; Irradiation;	65%
Multi-step reaction with 2 steps 2: sodium; toluene View Scheme

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) + monomethyl monopotassium malonate (38330-80-2) → 3-oxo-3-(1-phenyl-cyclopentyl)-propionic acid methyl ester (880352-58-9)

Conditions	Yield
Stage #1: 1-phenyl-1-cyclopentanecarboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 2h; Stage #2: monomethyl monopotassium malonate With magnesium chloride In tetrahydrofuran at 50℃;	65%

1-phenyl-1-cyclopentanecarboxylic acid (77-55-4) + 1-Phenyl-3-buten-1-ol (80735-94-0) → allyl 1-phenylcyclopentanecarboxylate

Conditions	Yield
With palladium diacetate; silver carbonate In 1,2-dichloro-benzene at 100℃; for 24h; Inert atmosphere;	65%

Upstream product

• 21573-69-3 1-phenyl-1-cyclopentanecarboxaldehyde 
• 110-52-1 1,4-dibromo-butane 
• 60-29-7 diethyl ether 
• 908520-36-5 1-phenyl-N-(quinolin-8-yl)cyclopentanecarboxamide 
• 4535-96-0 1-phenyl-1-cyclopentanecarboxylic acid methyl ester 
• 242482-24-2 methyl 2-phenyl-2-(prop-2-enyl)pent-4-enoate 
• 101-41-7 benzeneacetic acid methyl ester 
• 108-94-1 cyclohexanone 
• 823-45-0 2-(hydroxymethylene)cyclohexanone 
• 140-29-4 phenylacetonitrile 
• 64-18-6 formic acid 
• 10487-96-4 1-phenylcyclopentanol 
• 16537-09-0 t-butyl phenylacetate 
• 77-57-6 1-phenyl-1-cyclopentanecarbonitrile 

Downstream Products

• 77-22-5 caramiphen 
• 29885-29-8 1-Phenyl-cyclopentan-1-carbonsaeure-<2-(tert.-butyl-methyl-amino)-ethylester> 
• 4535-96-0 1-phenyl-1-cyclopentanecarboxylic acid methyl ester 
• 59115-90-1 1-hydroxymethyl-1-phenylcyclopentane 
• 52648-77-8 1-(4-nitro-phenyl)-cyclopentanecarboxylic acid 
• 15811-02-6 bis-(1-phenyl-cyclopentyl)-ketone 
• 59358-70-2 1,1'-Diphenyl-1,1'-bicyclopentyl 
• 68580-51-8 1-Phenyl-cyclopentanecarboperoxoic acid tert-butyl ester 
• 17380-74-4 1-phenylcyclopentylamine 
• 135569-28-7 1-(p-iodophenyl)cyclopentanecarboxylic acid 
• 457077-86-0 C₁₂H₁₃N₃O 
• 880352-58-9 3-oxo-3-(1-phenyl-cyclopentyl)-propionic acid methyl ester 
• 908520-36-5 1-phenyl-N-(quinolin-8-yl)cyclopentanecarboxamide 
• 5296-89-9 1-phenylcyclopentane-1-carboxamide 

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