1636-39-1

Basic information

• Product Name: BICYCLOPENTYL
• Synonyms: BICYCLOPENTYL;1,1'-Bicyclopentyl;(1α,1'α)-1,1'-Bi(cyclopentane);1,1'-Bicyclopentane;1α-(Cyclopentane-1α-yl)cyclopentane;1β-(Cyclopentane-1α-yl)cyclopentane;Cyclopentylcyclopentane;Dicyclopentyl
• CAS NO: 1636-39-1
• Molecular Formula: C₁₀H₁₈
• Molecular Weight: 138.25
• EINECS: 216-666-2
• Mol File: 1636-39-1.mol
• Article Data: 32

Chemical Properties

• Melting Point: -35.352--35.331 °C
• Boiling Point: 188.7°C (rough estimate)
• Flash Point: 51.6°C
• Appearance: /
• Density: 0.8102 (estimate)
• Vapor Pressure: 0.891mmHg at 25°C
• Refractive Index: 1.4860 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Hexanes (Slightly)
• Stability: Volatile
• CAS DataBase Reference: BICYCLOPENTYL(CAS DataBase Reference)
• NIST Chemistry Reference: BICYCLOPENTYL(1636-39-1)
• EPA Substance Registry System: BICYCLOPENTYL(1636-39-1)

Safety Data

• Hazardous Substances Data: 1636-39-1(Hazardous Substances Data)

Usage

Uses

1,?1''-?Bicyclopentyl along with butanal mixtures are used to produce high density aviation fuel.

InChI:InChI=1/C10H18/c1-2-6-9(5-1)10-7-3-4-8-10/h9-10H,1-8H2

Synthetic route

Cyclopentyl bromide (137-43-9) → bicyclopentyl (1636-39-1)

Conditions	Yield
With triethanolamine; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; [Ni(2,2′:6′,2''-terpyridine)(pyridine)(CH3CN)2](PF6)2 In acetonitrile at 23 - 28℃; for 12h; Reagent/catalyst; Inert atmosphere; Sealed tube; Irradiation;	96%
With manganese; (1,2-dimethoxyethane)dichloronickel(II); 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In N,N-dimethyl-formamide at 40℃; for 18h;	82%
With Ni(0)*2EC*Py complex In acetonitrile at 20℃; for 4h; Inert atmosphere;	48%

2-cyclopentylidenecyclopentan-1-one (825-25-2) → bicyclopentyl (1636-39-1)

Conditions	Yield
With hydrogen at 250℃; under 45004.5 Torr; for 48h; Autoclave;	95.8%
With Ni-doped silica; hydrogen In neat (no solvent) at 179.84℃; under 45004.5 Torr; Reagent/catalyst; Temperature; Flow reactor;	93%
With hydrogen at 180℃; under 30003 Torr; Autoclave;	91%
Multi-step reaction with 2 steps 1: H2 / Raney-Ni / ethanol 2: N2H4*H2O, aq. NaOH / bis-(2-hydroxy-ethyl) ether View Scheme

(1,1'-bicyclopentyl)-2-one (2866-71-9, 3063-68-1, 4884-24-6, 2865-81-8, 14112-41-5) → bicyclopentyl (1636-39-1)

Conditions	Yield
With hydrogen In neat (no solvent) at 200℃; under 37503.8 Torr; for 36h; Autoclave;	93%
With sodium hydroxide; hydrazine hydrate In diethylene glycol

Cyclopentyl bromide (137-43-9) → bicyclopentyl (1636-39-1) + cyclopentylmagnesium bromide (33240-34-5)

Conditions	Yield
With tetrahydrofuran; magnesium chloride at 37℃; Product distribution; Mechanism; effect of solvent deuteration, other reagents;	A 2% B 71%

Cyclopentyl bromide (137-43-9) + bromobenzene (108-86-1) → biphenyl (92-52-4) + Cyclopentane (287-92-3) + cyclopentylbenzene (700-88-9) + bicyclopentyl (1636-39-1) + benzene (71-43-2)

Conditions	Yield
With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 4,4'-Dimethoxy-2,2'-bipyridin; NiI2*3.5H2O; sodium iodide; zinc at 20 - 60℃; for 25h; chemoselective reaction;	A n/a B n/a C 63% D n/a E n/a

Cyclopentane (287-92-3) + percarbonate de O,O-tert-butyle et O-isopropyle (65700-06-3) → 1-cyclopentyl-propan-2-one (1122-98-1) + bicyclopentyl (1636-39-1) + 2,5-hexanedione (110-13-4) + tert-butyl alcohol (75-65-0)

Conditions	Yield
at 130℃; for 2.5h; Further byproducts given;	A 57% B n/a C n/a D n/a

bicyclopentyl-1,1'-diene (934-02-1) → bicyclopentyl (1636-39-1)

Conditions	Yield
With ethanol; platinum Hydrogenation;
With hydrogen; palladium on activated charcoal In diethyl ether for 2h; Ambient temperature; Yield given;
Multi-step reaction with 2 steps 1: diethyl ether / Irradiation 2: H2 / PtO2 / pentane; acetic acid View Scheme

1,1,2,2-tetrachloroethylene (127-18-4) + Cyclopentane (287-92-3) → Trichloroethylene (79-01-6) + bicyclopentyl (1636-39-1) + Cyclopentyl-trichlorethylen (55255-41-9)

Conditions	Yield
at 26℃; Irradiation;

cyclopentanealdehyde (872-53-7) → bicyclopentyl (1636-39-1)

Conditions	Yield
With 2,2-Dimethylbutane Irradiation;

1,10‐dichlorodec‐5‐yne (14093-35-7) → 5-decyne (1942-46-7) + bicyclopentyl (1636-39-1) + pentylidenecyclopentane (53366-55-5)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 36h; Heating;

Cyclopentane (287-92-3) → Trichloroethylene (79-01-6) + bicyclopentyl (1636-39-1) + Cyclopentyl-trichlorethylen (55255-41-9)

Conditions	Yield
With 1,1,2,2-tetrachloroethylene at 26℃; Irradiation;

1-cyclopent-2-en-1-ylcyclopentene (17385-32-9) → bicyclopentyl (1636-39-1)

Conditions	Yield
With hydrogen; platinum(IV) oxide In acetic acid; pentane

3-Cyclopentylidenecyclopentene (28749-02-2) → bicyclopentyl (1636-39-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal

3-Hydroxy-1-cyclopentyl-cyclopentan (103983-43-3) → bicyclopentyl (1636-39-1)

Conditions	Yield
(i) Al2O3, (ii) H2, PtO2, EtOAc; Multistep reaction;

dicyclopentylzinc (20525-74-0) → bicyclopentyl (1636-39-1)

Conditions	Yield
In diethyl ether (electrolysis);

cyclopentyl-lithium (23473-12-3) → bicyclopentyl (1636-39-1)

Conditions	Yield
In diethyl ether (electrolysis);

C10H18Cd → bicyclopentyl (1636-39-1)

Conditions	Yield
In diethyl ether (electrolysis);

2a,3,3a,5a,6,6a,6b,6c-octahydro-3,6-cyclo-cyclopenta[3,4]pentaleno[1,6-cd]pyrazole (54107-03-8) → bicyclopentyl (1636-39-1)

Conditions	Yield
(i) (pyrolysis), (ii) H2, PtO2, MeOH; Multistep reaction;

cyclopentylmagnesium bromide (33240-34-5) → bicyclopentyl (1636-39-1)

Conditions	Yield
With thallium(I) bromide In tetrahydrofuran; benzene Heating;
In diethyl ether (electrolysis);

tetrahydrofuran (109-99-9) + Cyclopentane (287-92-3) → octahydro-2,2′-bifuran (1592-33-2) + 2-cyclopentyltetrahydrofuran (90645-71-9) + bicyclopentyl (1636-39-1)

Conditions	Yield
With mercury at 50℃; for 72h; Irradiation; Yield given. Yields of byproduct given;

tetrahydrofuran (109-99-9) → octahydro-2,2′-bifuran (1592-33-2) + bicyclopentyl (1636-39-1)

Conditions	Yield
With mercury at 50℃; for 72h; Product distribution; Irradiation; other temperature, other time;

bicyclopentyl (1636-39-1) → tetradecachloro-[1,1']bicyclopent-1-enyl (27396-27-6)

Conditions	Yield
With chlorine at 175℃; UV-Licht;

bicyclopentyl (1636-39-1) → Bicyclopenty-1-yl-hydroperoxide (4884-26-8)

Conditions	Yield
With oxygen

bicyclopentyl (1636-39-1) → Bicyclopentyl-1,1'-diyl bis-hydroperoxide (4884-27-9)

Conditions	Yield
With oxygen

Upstream product

• 109-99-9 tetrahydrofuran 
• 7567-22-8 bromocyclooctatetraene 
• 23473-12-3 cyclopentyl-lithium 
• 287-92-3 Cyclopentane 
• 96-41-3 Cyclopentanol 
• 120-92-3 cyclopentanone 
• 825-25-2 2-cyclopentylidenecyclopentan-1-one 
• 5181-75-9 bicyclopentyl-1,1'-diol 
• 96-40-2 2-cyclopenten-1-yl chloride 
• 66953-28-4 anti-tricyclo<4.2.1.1^2,5>dec-2-en-9-one 
• 91-17-8 decalin 
• 7133-21-3 cyclohexyl-cyclopentyl sulfide 
• 64-17-5 ethanol 
• 2690-17-7 3-cyclopentylcyclopent-1-ene 

Downstream Products

• 493-01-6 cis-decalin 
• 493-02-7 trans-Decalin 
• 91-20-3 naphthalene 
• 119-64-2 tetralin 
• 3875-51-2 isopropylcyclopentane 
• 4850-32-2 sec-butylcyclopentane 
• 4737-43-3 2-cyclopentyl-pentane 
• 4737-44-4 3-cyclopentyl-pentane 
• 4752-31-2 (±)-(1R*,4aS*,8aS*)-9-methylenedecahydro-1,4a-(epoxymethano)naphthalene 

Related news

High-energy components of “designer gasoline and designer diesel fuel” I. Heat capacities, enthalpy increments, vapor pressures, critical properties, and derived thermodynamic functions for BICYCLOPENTYL (cas 1636-39-1) between the T=(10 and 600) K07/24/2019

Measurements leading to the calculation of the standard thermodynamic properties for gaseous bicyclopentyl (Chemicals s registry number [1636-39-1]) are reported. Experimental methods include adiabatic heat-capacity calorimetry, comparative ebulliometry, and differential-scanning calorimetry (d....detailed

Relevant articles and documents

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