766-00-7

Basic information

• Product Name: 2-CYCLOPENTYLETHANOL
• Synonyms: 2-Cyclopentanethanol;2-Cyclopentylethanol,97%;2-Cyclopentylethan-1-ol;2-Cyclopentylethanol 2-Hydroxyethylcyclopentane;2-Cyclopentylethanol, 98+% SynonyMs 2-Cyclopentaneethanol;Cyclopentylethanol;2-HYDROXYETHYLCYCLOPENTANE;2-CYCLOPENTYLETHANOL
• CAS NO: 766-00-7
• Molecular Formula: C₇H₁₄O
• Molecular Weight: 114.19
• EINECS: 212-156-9
• Mol File: 766-00-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 78-80°C 10mm
• Flash Point: 78-80°C/10mm
• Appearance: /
• Density: 0,92 g/cm3
• Vapor Pressure: 0.376mmHg at 25°C
• Refractive Index: 1.4585
• Storage Temp.: 2-8°C
• Solubility: Chloroform, DMSO, Methanol
• PKA: 15.22±0.10(Predicted)
• BRN: 2069860
• CAS DataBase Reference: 2-CYCLOPENTYLETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CYCLOPENTYLETHANOL(766-00-7)
• EPA Substance Registry System: 2-CYCLOPENTYLETHANOL(766-00-7)

Safety Data

• Safety Statements: 23-24/25
• Hazardous Substances Data: 766-00-7(Hazardous Substances Data)

Usage

Uses

Cyclopentaneethanol is used in the prepartion of phenylalanine derivatives for incorporation into peptides as CD4 mimetic miniproteins interacting with HIV-1 surface glycoprotein. It is also used in the preparation of tertiary amine muscarinic receptor antagonists applied towards the treatment of chronic obstructive pulmonary disease.

InChI:InChI=1/C7H14O/c8-6-5-7-3-1-2-4-7/h7-8H,1-6H2

Synthetic route

2-cyclopent-2-enyl-ethanol (766-02-9) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
Stage #1: 2-cyclopent-2-enyl-ethanol With pyridinium p-toluenesulfonate In 1,2-dichloro-ethane at 80℃; for 20h; Stage #2: With triethylamine In dichloromethane at 20℃; for 6h; Stage #3: With trifluoroacetic acid In methanol; dichloromethane at 140℃; for 0.0666667h; microwave irradiation; Further stages.;	100%
With palladium Hydrogenation;
With platinum Hydrogenation;

2-cyclopentylacetic acid (1123-00-8) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran; toluene at 0 - 20℃; for 16h;	90%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 13h; Deacetylation;	86%
With lithium aluminium tetrahydride In tetrahydrofuran 1) 1h, 90 deg C 2) 3h, reflux;	78%

oxirane (75-21-8) + cyclopentylmagnesium chloride (32916-51-1) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
With diethyl ether at 5℃;

oxirane (75-21-8) + cyclopentylmagnesium bromide (33240-34-5) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
With diethyl ether

ethyl cyclopentylacetate (18322-54-8) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
With ethanol; sodium
With lithium aluminium tetrahydride; diethyl ether
With lithium aluminium tetrahydride In tetrahydrofuran

cyclopentylacetic acid methyl ester (2723-38-8) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
With ethanol; sodium

oxirane (75-21-8) + cyclopenta-1,3-diene (542-92-7) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
(i) KOtBu, tBuOH, (ii) /BRN= 102378/, (iii) H2, PtO2; Multistep reaction;

2-(cyclopent-3-en-1-yl)ethan-1-ol (766-01-8) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
With hydrogen

ethyl cyclopentylideneacetate (1903-22-6) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / 5percent Pd/C / ethanol / 760 Torr 2: LiAlH4 / tetrahydrofuran View Scheme

cyclopentanone (120-92-3) + diluted alcoholic KOH → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaH / benzene 2: H2 / 5percent Pd/C / ethanol / 760 Torr 3: LiAlH4 / tetrahydrofuran View Scheme

(2-oxocyclopent)acetic acid (104115-44-8) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / KOH, hydrazine hydrate / ethane-1,2-diol / Heating; 1) 160-165 deg C 2) 4h, 195-200 deg C 2: 78 percent / 1) LAH / tetrahydrofuran / 1) 1h, 90 deg C 2) 3h, reflux View Scheme

Cyclopentyl bromide (137-43-9) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: xylene 2: ethanol 3: sodium; ethanol View Scheme

ethyl 2-cyclopentyl-3-oxobutanoate (1540-32-5) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol 2: sodium; ethanol View Scheme

toluene-4-sulfonic acid cyclopent-3-enyl ester (36367-85-8) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
Multi-step reaction with 4 steps 2: aq. KOH / ethanol 3: (i) Py, (ii) LiAlH4 4: H2 View Scheme

<α-Cyan-α-(Δ3-cyclopentenyl)>-essigsaeure-ethylester (103095-34-7) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. KOH / ethanol 2: (i) Py, (ii) LiAlH4 3: H2 View Scheme

2-(Δ3-Cyclopentyl)-malonsaeure (771-00-6) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) Py, (ii) LiAlH4 2: H2 View Scheme

bis(3-cyclopentylpropanoyl) peroxide (955017-60-4) → vinylcyclopentane (3742-34-5) + 2-cyclopentyl-ethanol (766-00-7) + 1,4-dicyclopentylbutane (2980-70-3) + 2-cyclopentylethyl 3-cyclopentylpropanoate (955017-64-8)

Conditions	Yield
In hexane at 80℃; Kinetics;	A 7.4 %Chromat. B 8 %Chromat. C 22 %Chromat. D 22 %Chromat.

6-iodohex-1-ene (18922-04-8) + carbon monoxide (201230-82-2) → 2-cyclopentyl-ethanol (766-00-7)

Conditions	Yield
Stage #1: 6-iodohex-1-ene; carbon monoxide With diethoxymethylane; [CuCl(IPrMe)]; lithium methanolate In tetrahydrofuran at 60℃; under 2280.15 Torr; for 16h; Sealed tube; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; diethyl ether at 20℃; for 2h;	68 %Spectr.

2-cyclopentyl-ethanol (766-00-7) → 2-cyclopentylacetaldehyde (5623-81-4)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane at 20℃; for 3h;	100%
With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 4h;	50.9%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -61 - 20℃; Dehydration;	27.4%

2-cyclopentyl-ethanol (766-00-7) + methanesulfonyl chloride (124-63-0) → 2-cyclopentylethyl methanesulfonate (73779-38-1)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 19h;	100%
With triethylamine In dichloromethane at 0℃; for 2h;	100%
With pyridine for 18h;
With triethylamine In dichloromethane at 5℃; for 1h;
With triethylamine In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;

2-cyclopentyl-ethanol (766-00-7) + p-toluenesulfonyl chloride (98-59-9) → 2-cyclopentylethyl 4-methylbenzenesulfonate (786-33-4)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 16h;	98.2%
With dmap; triethylamine In dichloromethane at 20℃; for 16h;
In chloroform at 0 - 20℃; for 3.5h; Inert atmosphere;
With dmap; triethylamine
With pyridine at 0 - 20℃; for 36h;

2-cyclopentyl-ethanol (766-00-7) → sulfamic acid 2-cyclopentylethyl ester (931410-28-5)

Conditions	Yield
Stage #1: With formic acid; isocyanate de chlorosulfonyle In dichloromethane at 0 - 20℃; for 1.33h; Stage #2: 2-cyclopentyl-ethanol With pyridine In dichloromethane at 7℃; for 2h; Stage #3: With sodium hydrogencarbonate In dichloromethane; water; ethyl acetate	95%

isocyanate de chlorosulfonyle (1189-71-5) + 2-cyclopentyl-ethanol (766-00-7) → sulfamic acid 2-cyclopentylethyl ester (931410-28-5)

Conditions	Yield
Stage #1: isocyanate de chlorosulfonyle With formic acid at 0 - 20℃; for 1.33h; Inert atmosphere; Stage #2: 2-cyclopentyl-ethanol With pyridine In dichloromethane at 0 - 7℃; for 2h; Inert atmosphere;	95%

2-cyclopentyl-ethanol (766-00-7) → perhydrocyclopentafuran (5549-40-6, 18320-80-4, 32923-08-3)

Conditions	Yield
With lead(IV) acetate; calcium carbonate In benzene for 48h; Heating;	93%

C16H19IN6O (1160582-86-4) + 2-cyclopentyl-ethanol (766-00-7) → C23H32N6O2 (1160583-04-9)

Conditions	Yield
With copper(l) iodide; Phenanthroline; caesium carbonate In 1,4-dioxane at 100℃; for 16h;	92%

C16H19BrN6O (1160582-80-8) + 2-cyclopentyl-ethanol (766-00-7) → C23H32N6O2 (1160583-04-9)

Conditions	Yield
With sodium hexamethyldisilazane In tetrahydrofuran for 16h; Reflux;	90%

C17H25BrN4O3 (1160582-90-0) + 2-cyclopentyl-ethanol (766-00-7) → C24H38N4O4 (1160582-92-2)

Conditions	Yield
With sodium hexamethyldisilazane In tetrahydrofuran for 16h; Reflux;	88%

2-cyclopentyl-ethanol (766-00-7) → 2-cyclopentyl-1-iodoethane (195442-17-2)

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 2h;	84%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 2h; Inert atmosphere;	84%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 3h; Inert atmosphere;	75%

4-chloroquinoline (611-35-8) + 2-cyclopentyl-ethanol (766-00-7) → C16H18ClNO

Conditions	Yield
With 4,5,6,7-tetrafluoro-1-hydroxybenzo[d][1,2]iodaoxol-3(1H)-one; Ru(bpy)3Cl2 at 30℃; for 24h; Minisci Aromatic Substitution; Inert atmosphere; Irradiation; regioselective reaction;	83%

2-cyclopentyl-ethanol (766-00-7) + 3-methylsulfanyl-4H-[1,2,4]triazole (7411-18-9) → C10H16N4S (1626400-18-7)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 80℃; Mitsunobu Displacement; regioselective reaction;	77%

6-hydroxy-1H-indole (2380-86-1) + 2-cyclopentyl-ethanol (766-00-7) → 6-(2-cyclopentylethoxy)indole (142535-22-6)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran	75%

2-cyclopentyl-ethanol (766-00-7) → (2-bromo-ethyl)-cyclopentane (18928-94-4)

Conditions	Yield
With sulfuric acid; hydrogen bromide for 6h; Heating;	72%
With sulfuric acid; hydrogen bromide
With phosphorus tribromide at -5 - 0℃; zuletzt bei 100grad;

C8H8Br2N2O (1160582-78-4) + 2-cyclopentyl-ethanol (766-00-7) → C15H21BrN2O2 (1160582-98-8)

Conditions	Yield
With sodium hexamethyldisilazane In 1,4-dioxane at 50℃; for 2h;	70%

(2S)-2-(4-tert-butylphenoxy)-3-(4-{2-[(1α,5α,6α)-3-(2,4,5-trifluorobenzyl)-3-azabicyclo[3.1.0]hex-6-ylamino]ethoxy}phenyl)propionic acid (1003879-95-5) + 2-cyclopentyl-ethanol (766-00-7) → (2S)-2-(4-tert-butylphenoxy)-3-(4-{2-[(1α,5α,6α)-3-(2,4,5-trifluorobenzyl)-3-azabicyclo[3.1.0]hex-6-ylamino]ethoxy}phenyl)propionic acid 2-cyclopentylethyl ester

Conditions	Yield
Stage #1: (2S)-2-(4-tert-butylphenoxy)-3-(4-{2-[(1α,5α,6α)-3-(2,4,5-trifluorobenzyl)-3-azabicyclo[3.1.0]hex-6-ylamino]ethoxy}phenyl)propionic acid; 2-cyclopentyl-ethanol With sulfuric acid In benzene for 6h; Heating / reflux; Stage #2: With ammonia In chloroform pH=8;	69%

6-Benzyloxy-3-[3-methyl-4-[(1-pyrrolidinyl)methyl]-benzyl]-2-(4-hydroxyphenyl)benzo[b]thiophene (193966-06-2) + 2-cyclopentyl-ethanol (766-00-7) → 6-Benzyloxy-3-[3-methyl-4-[(1-pyrrolidinyl)methyl]-benzyl]-2-[4-(2-cyclopentylethoxy)phenyl]benzo[b]thiophene (215388-37-7)

Conditions	Yield
With triethanolamine In tetrahydrofuran; SiO2	58%

2-cyclopentyl-ethanol (766-00-7) + triethylammonium N-tert-butylsulfamate → 2-cyclopentylethyl tert-butylsulfamate

Conditions	Yield
Stage #1: triethylammonium N-tert-butylsulfamate With trifluoromethylsulfonic anhydride; Triphenylphosphine oxide In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at -78℃; for 0.25h; Inert atmosphere; Stage #3: 2-cyclopentyl-ethanol In dichloromethane at -78 - 22℃; for 18h; Inert atmosphere;	56%

ethyl 2-((4,6-dihydroxypyrimidin-2-yl)thio)hexanoate (916482-23-0) + 2-cyclopentyl-ethanol (766-00-7) → ethyl 2-(4,6-bis(2-cyclopentylethoxy)pyrimidin-2-ylthio)hexanoate (1231734-03-4)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction; Inert atmosphere; Cooling with ice;	55.3%

Homophthalic acid (89-51-0) + 2-cyclopentyl-ethanol (766-00-7) → 2-[2-(2-cyclopentylethoxy)-2-oxoethyl]benzoic acid (1034706-07-4)

Conditions	Yield
With sulfuric acid In benzene for 6h; Heating;	47%

2-cyclopentyl-ethanol (766-00-7) + 3-(2-fluoro-5-(methylsulfonyl)phenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine → 3-[2-(2-cyclopentylethoxy)-5-(methylsulfonyl)phenyl]-1-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

Conditions	Yield
Stage #1: 2-cyclopentyl-ethanol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.0833333h; Stage #2: 3-(2-fluoro-5-(methylsulfonyl)phenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine In tetrahydrofuran; mineral oil at 60℃; for 12h; Stage #3: With hydrogenchloride In 1,4-dioxane at 70℃; for 12h;	34.5%

Benzyl phenyl sulfone (3112-88-7) + 2-cyclopentyl-ethanol (766-00-7) → C27H28O2S

Conditions	Yield
With ruthenium(bis[2‐(ethylsulfanyl)ethyl]amine)(dichloro)(triphenylphosphine); potassium hexamethylsilazane In toluene at 120℃; for 12h; Schlenk technique; Inert atmosphere; Glovebox;	31%

2-cyclopentyl-ethanol (766-00-7) + N-{3-[5-(3-hydroxyphenyl)[1,3]dioxan-2-yl]propyl}acetamide (1257243-77-8) → N-(3-{5-[3-(2-cyclopentylethoxy)phenyl][1,3]dioxan-2-yl}propyl)acetamide (1257243-97-2)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 2h; Mitsunobu reaction;	14%

2-cyclopentyl-ethanol (766-00-7) + 2-Amino-6-chloropurin (10310-21-1) → 2-amino-6-[(cyclopentylethyl)oxy]purine

Conditions	Yield
With sodium hydride In 1,4-dioxane for 4h; Reflux;	7%

2-cyclopentyl-ethanol (766-00-7) → 4-nitro-benzoic acid-(2-cyclopentyl-ethyl ester)

Upstream product

• 75-21-8 oxirane 
• 32916-51-1 cyclopentylmagnesium chloride 
• 33240-34-5 cyclopentylmagnesium bromide 
• 766-02-9 2-cyclopent-2-enyl-ethanol 
• 2723-38-8 cyclopentylacetic acid methyl ester 
• 18922-04-8 6-iodohex-1-ene 
• 201230-82-2 carbon monoxide 
• 955017-60-4 bis(3-cyclopentylpropanoyl) peroxide 
• 771-00-6 2-(Δ³-Cyclopentyl)-malonsaeure 
• 103095-34-7 <α-Cyan-α-(Δ³-cyclopentenyl)>-essigsaeure-ethylester 
• 36367-85-8 toluene-4-sulfonic acid cyclopent-3-enyl ester 
• 1540-32-5 ethyl 2-cyclopentyl-3-oxobutanoate 
• 137-43-9 Cyclopentyl bromide 
• 104115-44-8 (2-oxocyclopent)acetic acid 

Downstream Products

• 5623-81-4 2-cyclopentylacetaldehyde 
• 791-65-1 2--aethyl-<4-nitro-benzolsulfonat> 
• 1640-89-7 ethylcyclopentane 
• 82166-21-0 methyl cyclohexane 
• 68104-99-4 ethyl 4-cyclopentyl-3-oxobutanoate 
• 857804-04-7 (2-cyclopentyl-ethyl)-hexyl-malonic acid diethyl ester 
• 857804-05-8 (2-cyclopentyl-ethyl)-hexyl-malonic acid 
• 786-33-4 2-cyclopentylethyl 4-methylbenzenesulfonate 
• 96-37-7 methyl-cyclopentane 
• 73779-38-1 2-cyclopentylethyl methanesulfonate 
• 6749-58-2 4-Brom-benzolsulfonsaeure-<2-cyclopentyl-ethylester> 
• 84226-36-8 2-cyclopentylethyl chloride 
• 18928-94-4 (2-bromo-ethyl)-cyclopentane 

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