13074-65-2

Basic information

• Product Name: 2-N-HEXYLCYCLOPENTANONE
• Synonyms: 2-hexyl-cyclopentanon;hexylcyclopentanone;JASMATONE;2-N-HEXYLCYCLOPENTANONE;2-HEXYLCYCLOPENTANONE;2-hexylcyclopentan-1-one;Cyclopentanone, 2-hexyl-;2-Hexylcyclopentan-1-on
• CAS NO: 13074-65-2
• Molecular Formula: C₁₁H₂₀O
• Molecular Weight: 168.28
• EINECS: 235-970-6
• Mol File: 13074-65-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 108-110°C 10mm
• Flash Point: 112°C
• Appearance: light yellow liquid
• Density: 0,89 g/cm3
• Vapor Pressure: 2.1Pa at 20℃
• Refractive Index: 1.4495
• Storage Temp.: 2-8°C
• Water Solubility: 59.5mg/L at 20℃
• BRN: 2041950
• CAS DataBase Reference: 2-N-HEXYLCYCLOPENTANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-N-HEXYLCYCLOPENTANONE(13074-65-2)
• EPA Substance Registry System: 2-N-HEXYLCYCLOPENTANONE(13074-65-2)

Safety Data

• RTECS: GY4972000
• TSCA: Yes
• Hazardous Substances Data: 13074-65-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 98, p. 248, 1976 DOI: 10.1021/ja00417a048

Synthetic route

1-hexene (592-41-6) + cyclopentanone (120-92-3) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
With tert.-butylhydroperoxide at 150 - 160℃; under 12000.9 - 13501.1 Torr;	68%
With di-tert-butyl peroxide at 130℃; for 6.5h;	43.5%
With 7-azaindoline; chlorobis(cyclooctene)rhodium(I) dimer; tert-Octylamine; toluene-4-sulfonic acid; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene In water at 130℃; for 48h; Catalytic behavior; regioselective reaction;
With di-tert-butyl peroxide at 140 - 160℃; Autoclave;

2-hexylidenecyclopentanone (17373-89-6) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
With hydrogen; palladium on activated charcoal
Ir(CO)(PPh3)2Cl at 240℃;

1-hexene (592-41-6) + lithium cyclopent-1-enolate (37160-52-4) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
Yield given. Multistep reaction;

(2-Hexyl-cyclopent-1-enylsulfanyl)-benzene (58567-72-9) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
With water; titanium tetrachloride; acetic acid

1-Trimethylsiloxy-2-n-hexylcyclopenten (39834-30-5) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
(hydrolysis);
With hydrogenchloride

1-bromo-hexane (111-25-1) + 2-cyclopentylidene-1,1-dimethylhydrazine (14090-60-9) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
With potassium dihydrogenphosphate; n-butyllithium; phosphonic Acid 1.) THF, -30 deg C, 1 h, 2.) 25 deg C, 2 h, 3.) 25 deg C, overnight; Yield given. Multistep reaction;

(+-)-1-hexyl-cyclopenten-(2)-one-(5) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
With ethanol; nickel Hydrogenation;

1-hexyl-cyclopenten-(1)-one-(5) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
With ethanol; nickel Hydrogenation;

1-hexylidene-cyclopentanone-(2) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
Hydrogenation;

cyclopentanone (120-92-3) + 2-methyl-phenethyl magnesium chloride → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
Multi-step reaction with 2 steps 2: 1.) n-BuLi, 3.) KH2OP4, H3PO3 / 1.) THF, -30 deg C, 1 h, 2.) 25 deg C, 2 h, 3.) 25 deg C, overnight View Scheme

hexanal (66-25-1) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) aq. KOH, (ii) oxalic acid 2: H2 / Pd-C View Scheme
Multi-step reaction with 2 steps 1: (i) benzene, (ii) aq. HCl 2: Ir(CO)(PPh3)2Cl / 240 °C View Scheme

2-Hexyl-2-methyl-1-oxa-spiro[2.2]pentane (39834-28-1) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) LiNEt2, (ii) /BRN= 1209232/ 2: 330 °C 3: aq. HCl View Scheme

2-(1-Trimethylsiloxycyclopropyl)oct-1-en (39834-29-2) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0 h / 330 °C 2: (hydrolysis) View Scheme
Multi-step reaction with 2 steps 1: 330 °C 2: aq. HCl View Scheme

[1-(1-Methylene-heptyl)-cyclopropylsulfanyl]-benzene (58567-67-2) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 350 °C 2: TiCl4, AcOH, H2O View Scheme

2-(1-Phenylsulfanyl-cyclopropyl)-octan-2-ol (63365-75-3) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2, Py 2: 350 °C 3: TiCl4, AcOH, H2O View Scheme

hexyl-methyl-ketone (111-13-7) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) KOH, (ii) Et2NLi, (iii) /BRN= 1209232/ 2: 0 h / 330 °C 3: (hydrolysis) View Scheme

hexanal (66-25-1) + cyclopentanone (120-92-3) → 2-hexylcyclopentanone (13074-65-2)

Conditions	Yield
With hydrogen at 140℃; under 26252.6 Torr; for 6.66667h; Autoclave;	75 %Chromat.

2-hexylcyclopentanone (13074-65-2) → (6S)-6-hexyltetrahydropyran-2-one (108861-13-8) + (R)-2-n-hexylcyclopentanone (214335-64-5)

Conditions	Yield
With YP-Gal; cyclomaltooctaose; engineered bakers' yeast cell culture at 30℃; for 60h; Baeyer-Villiger oxidation;	A 88% B 78%

chloro-trimethyl-silane (75-77-4) + 2-hexylcyclopentanone (13074-65-2) → 1-Trimethylsiloxy-2-n-hexylcyclopenten (39834-30-5)

Conditions	Yield
With pyridine; sodium iodide In acetonitrile	87%
With pyridine; sodium iodide In acetonitrile

2-hexylcyclopentanone (13074-65-2) → 6-hexyltetrahydro-2H-pyran-2-one (710-04-3)

Conditions	Yield
With MoOBr3; dihydrogen peroxide; acetic anhydride; acetic acid at 50 - 70℃; for 6h;	86%
With urea hydrogen peroxide adduct; acetic acid at 60℃; under 750.075 Torr; for 6h; Baeyer-Villiger oxidation;	78%
With Candida antarctica lipase; dihydrogen peroxide; n-tetradecanoic acid In toluene for 144h;	73%

2-hexylcyclopentanone (13074-65-2) → 2-(n-hexyl)-2-cyclopenten-1-one (95-41-0) + 2-chloro-2-hexylcyclopentanone (83593-56-0)

Conditions	Yield
With sulfuryl dichloride In tetrachloromethane for 1h; temp.: RT to 40 deg C;	A n/a B 78%

2-hexylcyclopentanone (13074-65-2) + ethylene glycol (107-21-1) → 6-hexyl-1,4-dioxaspiro[4.4]nonane (87735-16-8)

Conditions	Yield
With GdPO4*(MoO2)0.5PMo12O40 In toluene Reflux; Dean-Stark;	61.8%
With P0.17Mo2.4CoBr0.27O6.8 In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 6h;	57%

2-hexylcyclopentanone (13074-65-2) → 2-(n-hexyl)-2-cyclopenten-1-one (95-41-0) + (E)-2-n-hexylidenecyclopentanone (103517-11-9)

Conditions	Yield
With CuCl2*2H2O In ethanol; water Heating; 2:1 molar ratio of salt to ketone;	A 56% B n/a
With CuCl2*2H2O In ethanol; water Heating;	A 56% B n/a

2-hexylcyclopentanone (13074-65-2) + 3,4-dimethoxy-benzaldehyde (120-14-9) → 5-hexyl-2-veratrylidene-cyclopentanone (102600-88-4)

Conditions	Yield
With potassium hydroxide

2-hexylcyclopentanone (13074-65-2) → 2-(n-hexyl)-2-cyclopenten-1-one (95-41-0)

Conditions	Yield
With N-Bromosuccinimide; aniline 1) CCl4, reflux, 3 h, 2) rt, 15 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: 78 percent / sulfuryl chloride / CCl4 / 1 h / temp.: RT to 40 deg C 2: 94 percent Chromat. / 0.5 h / 60 °C / 15 Torr View Scheme

2-hexylcyclopentanone (13074-65-2) → (R)-6-hexyl-tetrahydro-2H-pyran-2-one (108861-12-7) + (6S)-6-hexyltetrahydropyran-2-one (108861-13-8) + 2-Hexyl-cyclopentanone + 2-Hexyl-cyclopentanone

Conditions	Yield
In water at 30℃; for 1.5h; pH 7.1; NADPH-dependent biotransformation by partially purified monooxygenase from (+)-camphor grown Ps. putida NCIMB 10007; further monooxygenases; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
In water at 30℃; for 1.5h; pH 7.1; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

sulfuric acid (7664-93-9) + 2-hexylcyclopentanone (13074-65-2) + K2S2O8 + K2SO4 → 6-hexyltetrahydro-2H-pyran-2-one (710-04-3)

Conditions	Yield
at 0 - 10℃; Erwaermen des Reaktionsprodukts mit 5prozent ig. wss. Schwefelsaeure auf dem Dampfbad;

2-hexylcyclopentanone (13074-65-2) → 5-Hexyl-bicyclo[3.1.0]hexan-1-ol (229638-73-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaI; pyridine / acetonitrile 2: Et2Zn / hexane 3: ClSiMe3; methanol / 0.25 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 87 percent / NaI, pyridine / acetonitrile 2: 90 percent / Et2Zn / hexane / 0.25 h / 25 °C 3: MeOH, Me3SiCl / 0.25 h / 25 °C View Scheme

2-hexylcyclopentanone (13074-65-2) → (5-Hexyl-bicyclo[3.1.0]hex-1-yloxy)-trimethyl-silane (211234-63-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaI; pyridine / acetonitrile 2: Et2Zn / hexane View Scheme
Multi-step reaction with 2 steps 1: 87 percent / NaI, pyridine / acetonitrile 2: 90 percent / Et2Zn / hexane / 0.25 h / 25 °C View Scheme

2-hexylcyclopentanone (13074-65-2) → (-)-2-hexyl-2-methylcyclopentanone

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent / NaI, pyridine / acetonitrile 2: 90 percent / Et2Zn / hexane / 0.25 h / 25 °C 3: MeOH, Me3SiCl / 0.25 h / 25 °C 4: DMAP / CH2Cl2 / 2 h / 25 °C 5: NaOH / methanol / 4 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: 87 percent / NaI, pyridine / acetonitrile 2: 90 percent / Et2Zn / hexane / 0.25 h / 25 °C 3: NaOH / methanol / 4 h / 60 °C View Scheme

2-hexylcyclopentanone (13074-65-2) → (+)-2-hexyl-2-methylcyclopentanone

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent / NaI, pyridine / acetonitrile 2: 90 percent / Et2Zn / hexane / 0.25 h / 25 °C 3: MeOH, Me3SiCl / 0.25 h / 25 °C 4: DMAP / CH2Cl2 / 2 h / 25 °C 5: NaOH / methanol / 4 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: 87 percent / NaI, pyridine / acetonitrile 2: 90 percent / Et2Zn / hexane / 0.25 h / 25 °C 3: NaOH / methanol / 4 h / 60 °C View Scheme

2-hexylcyclopentanone (13074-65-2) → ((1R,5R)-5-Hexyl-bicyclo[3.1.0]hex-1-yloxy)-trimethyl-silane

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent / NaI, pyridine / acetonitrile 2: 90 percent / Et2Zn / hexane / 0.25 h / 25 °C 3: MeOH, Me3SiCl / 0.25 h / 25 °C 4: DMAP / CH2Cl2 / 2 h / 25 °C 5: 1.) Lipozyme, t-BuOMe, 1-propanol, 2.) Et3N / 1.) 36 deg C, 8 h, 2.) 25 deg C, 18 h View Scheme

2-hexylcyclopentanone (13074-65-2) → ((1S,5S)-5-Hexyl-bicyclo[3.1.0]hex-1-yloxy)-trimethyl-silane

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent / NaI, pyridine / acetonitrile 2: 90 percent / Et2Zn / hexane / 0.25 h / 25 °C 3: MeOH, Me3SiCl / 0.25 h / 25 °C 4: DMAP / CH2Cl2 / 2 h / 25 °C 5: 1.) Lipozyme, t-BuOMe, 1-propanol, 2.) Et3N / 1.) 36 deg C, 8 h, 2.) 25 deg C, 18 h View Scheme

2-hexylcyclopentanone (13074-65-2) → Chloro-acetic acid 5-hexyl-bicyclo[3.1.0]hex-1-yl ester (211234-74-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / NaI, pyridine / acetonitrile 2: 90 percent / Et2Zn / hexane / 0.25 h / 25 °C 3: MeOH, Me3SiCl / 0.25 h / 25 °C 4: DMAP / CH2Cl2 / 2 h / 25 °C View Scheme

2-hexylcyclopentanone (13074-65-2) → Chloro-acetic acid (1R,5R)-5-hexyl-bicyclo[3.1.0]hex-1-yl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / NaI, pyridine / acetonitrile 2: 90 percent / Et2Zn / hexane / 0.25 h / 25 °C 3: MeOH, Me3SiCl / 0.25 h / 25 °C 4: 1.) DMAP, 2.) Lipozyme, t-BuOMe, 1-propanol / 1.) CHCl2, 25 deg C, 2 h, 2.) 36 deg C, 8 h View Scheme

2-hexylcyclopentanone (13074-65-2) → Chloro-acetic acid (1S,5S)-5-hexyl-bicyclo[3.1.0]hex-1-yl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / NaI, pyridine / acetonitrile 2: 90 percent / Et2Zn / hexane / 0.25 h / 25 °C 3: MeOH, Me3SiCl / 0.25 h / 25 °C 4: 1.) DMAP, 2.) Lipozyme, t-BuOMe, 1-propanol / 1.) CHCl2, 25 deg C, 2 h, 2.) 36 deg C, 8 h View Scheme

Upstream product

• 17373-89-6 2-hexylidenecyclopentanone 
• 592-41-6 1-hexene 
• 37160-52-4 lithium cyclopent-1-enolate 
• 120-92-3 cyclopentanone 
• 39834-29-2 2-(1-Trimethylsiloxycyclopropyl)oct-1-en 
• 66-25-1 hexanal 
• 111-13-7 hexyl-methyl-ketone 
• 63365-75-3 2-(1-Phenylsulfanyl-cyclopropyl)-octan-2-ol 
• 58567-67-2 [1-(1-Methylene-heptyl)-cyclopropylsulfanyl]-benzene 
• 39834-28-1 2-Hexyl-2-methyl-1-oxa-spiro[2.2]pentane 
• 111-25-1 1-bromo-hexane 
• 14090-60-9 2-cyclopentylidene-1,1-dimethylhydrazine 
• 39834-30-5 1-Trimethylsiloxy-2-n-hexylcyclopenten 
• 58567-72-9 (2-Hexyl-cyclopent-1-enylsulfanyl)-benzene 

Downstream Products

• 102600-88-4 5-hexyl-2-veratrylidene-cyclopentanone 
• 95-41-0 2-(n-hexyl)-2-cyclopenten-1-one 
• 103517-11-9 (E)-2-n-hexylidenecyclopentanone 
• 83593-56-0 2-chloro-2-hexylcyclopentanone 
• 710-04-3 6-hexyltetrahydro-2H-pyran-2-one 
• 25235-82-9 5-Hydroxyundecansaeure 

Relevant articles and documents

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Kinetic Patterns of Condensation of Alkyl- and Cycloalkylcyclopentanones with Dihydric Alcohols in the Presence of Polyoxomolybdate Modified with Oxides of Rare-Earth Elements

The results of condensation of C5–C7 alkyl- and cycloalkyl-substituted cyclopentanones with diatomic vicinal alcohols in the presence of polyoxomolybdate modified with gadolinium oxide are considered. Kinetic patterns are investigated and a kinetic model of the process is proposed. It was established that alkyl- and cycloalkyl derivatives of dioxaspironone are formed directly by two parallel-consecutive routes and through the stages of the preparation of the corresponding hemiacetal. The ratio of the rate constants of these routes depends on the composition and structure of the starting ketones and diols.

Enzymatic resolution of bicyclo[n.1.0]alkan-1-ols derivatives: Preparation of optically active α-substituted α-methylcycloalkanones

Optically active α-methyl α-substituted cycloalkanones are prepared by a chemoenzymatic sequence which involves a Lipozyme-catalyzed transesterification of 1-(chloroacetoxy)bicyclo[n.1.0]alkanes and ring opening of these cyclopropanol derivatives.