Bicyclo(2,2,2)-2-octene supplier

Name
2,2,2-BICYCLO-2-OCTENE
EINECS
CAS No. 931-64-6
Article Data39
CAS DataBase
Density 0.93 g/cm³
Solubility
Melting Point 111.4°C
Formula C₈H₁₂
Boiling Point 138.3 °C at 760 mmHg
Molecular Weight 108.183
Flash Point 18.5 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms BICYCLO(2.2.2)OCT-2-ENE;bicyclo[2.2.2]oct-2-ene;3,6-Endoethylenecyclohexene;
PSA 0.00000
LogP 2.36260

Synthetic route

: 94064-42-3
Bicyclo[2.2.2]octanon-(2)-p-toluolsulfonylhydrazonn

: 931-64-6
norbornene

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; methyllithium	99%
With N,N,N,N,-tetramethylethylenediamine; methyllithium In diethyl ether cooling;	99 % Chromat.

: endo-bicyclo<2.2.2>oct-5-en-2-ol mesylate

: 931-64-6
norbornene

Conditions

Conditions	Yield
With lithium triethylborohydride In tetrahydrofuran at 60℃; for 4h;	83%

: 77550-13-1
5-(phenylsulfonyl)bicyclo<2.2.2>oct-2-ene

: 931-64-6
norbornene

Conditions

Conditions	Yield
With disodium hydrogenphosphate; sodium amalgam In tetrahydrofuran; methanol for 3.5h;	78.5%
With sodium amalgam; Na2HPO4 buffer In methanol at -20℃;	78%

: 7131-66-0
Bicyclo<2.2.2>octane-2,3-di-exo-carboxylic anhydride

: 931-64-6
norbornene

Conditions

Conditions	Yield
With lead dioxide at 250℃;

: 51677-42-0
acetic acid bicyclo[2.2.2]oct-2-yl ester

: 931-64-6
norbornene

Conditions

Conditions	Yield
at 400℃;

: 2220-40-8
bicyclo[2.2.2]oct-5-en-2-one

: 931-64-6
norbornene

Conditions

Conditions	Yield
With hydrazine hydrate anschliessend Erhitzen mit Kaliumhydroxid und Diaethylenglykol auf 220grad;

: 74-85-1
ethene

: 1165952-91-9
cyclohexa-1,3-diene

: 931-64-6
norbornene

Conditions

Conditions	Yield
at 250℃;
at 280℃;

: 74-85-1
ethene

: 1165952-91-9
cyclohexa-1,3-diene

: 123-31-9
hydroquinone

: 931-64-6
norbornene

Conditions

Conditions	Yield
at 250℃; under 58840.6 Torr;

...Expand

: 90893-09-7
1-phenyl-3-(bicyclo<2.2.2>octan-2-yl)triazene

A: 931-64-6
norbornene

: 51744-61-7, 51744-62-8, 92015-56-0, 135094-46-1, 145166-92-3
exo-bicyclo<3.2.1>octan-2-yl acetate

C: 285-43-8
tricyclo<3.2.1.02,7>octane

D: 51677-42-0
bicyclo<2.2.2>oct-2-yl-acetate

: 93638-25-6, 93638-27-8
N-(endo-bicyclo<3.2.1>)oct-2-yl-aniline

Conditions

Conditions	Yield
With sodium acetate; acetic acid Product distribution; Mechanism; deamination reactions of amine via triazene;

...Expand

: 90893-13-3
ethyl N-nitroso-N-(bicyclo<3.2.1>octan-2-yl)carbamate

A: 931-64-6
norbornene

: 823-02-9, 61617-43-4, 84235-38-1
Bicyclo<3.2.1>oct-2-ene

C: 93638-23-4
N-(bicyclo<2.2.2>octyl)aniline

D: 285-43-8
tricyclo<3.2.1.02,7>octane

E: 93638-31-4
(1R,3R,5S)-Bicyclo[3.2.1]oct-3-yl-phenyl-amine

: 93638-25-6, 93638-27-8
N-(exo-bicyclo<3.2.1>oct-2-yl)aniline

Conditions

Conditions	Yield
With ethanol Product distribution; Mechanism; deamination reactions of amine via nitrosocarbamate;

...Expand

: 89279-63-0
S-p-tolyl-S-vinyl-N-(p-tolylsulfonyl)sulfoximine

: 1165952-91-9
cyclohexa-1,3-diene

: 931-64-6
norbornene

Conditions

Conditions	Yield
With disodium hydrogenphosphate; sodium amalgam 1.) CHCl3, 110 deg C, 50 h 2.) r.t., 75 min; Yield given. Multistep reaction;

: 90893-12-2, 90893-14-4
ethyl N-nitroso-N-(exo-bicyclo<3.2.1>octan-2-yl)carbamate

A: 931-64-6
norbornene

: 823-02-9, 61617-43-4, 84235-38-1
Bicyclo<3.2.1>oct-2-ene

C: 93638-23-4
N-(bicyclo<2.2.2>octyl)aniline

D: 285-43-8
tricyclo<3.2.1.02,7>octane

E: 93638-29-0
(1S,3S,5R)-Bicyclo[3.2.1]oct-3-yl-phenyl-amine

: 93638-25-6, 93638-27-8
N-(exo-bicyclo<3.2.1>oct-2-yl)aniline

Conditions

Conditions	Yield
With ethanol Product distribution; Mechanism; deamination reactions of amine via nitrosocarbamate;

...Expand

: 3-(Trimethylsilyl)bicyclo<2.2.2>octan-2-carbonsaeure

: 931-64-6
norbornene

Conditions

Conditions	Yield
With potassium hydroxide In ethanol; acetonitrile Ambient temperature; electrolysis: C-anode, Pt-catode;	74 % Chromat.

: trans-2,3-diiodobicyclo<2.2.2>octane

: 931-64-6
norbornene

Conditions

Conditions	Yield
With methyl iodide In gas at 100℃;

: 7131-66-0
Bicyclo<2.2.2>octane-2,3-di-exo-carboxylic anhydride

lead (IV)-oxide: lead (IV)-oxide

: 931-64-6
norbornene

Conditions

Conditions	Yield
at 250℃;

(+-)-2-trimethylammonio-bicyclo<2.2.2>octane hydroxide: (+-)-2-trimethylammonio-bicyclo<2.2.2>octane hydroxide

A: 931-64-6
norbornene

B (+-)-2-dimethylamino-bicyclo<2.2.2>octane: (+-)-2-dimethylamino-bicyclo<2.2.2>octane

Conditions

Conditions	Yield
With potassium hydroxide

: 497-35-8, 139683-15-1
2-methylenebicyclo[2.2.1]heptane

phosphoric acid /kieselguhr: phosphoric acid /kieselguhr

A: 931-64-6
norbornene

B cis-1,2,3,3a,4,6a-hexahydro-pentalene: cis-1,2,3,3a,4,6a-hexahydro-pentalene

C substances of high boiling point: substances of high boiling point

Conditions

Conditions	Yield
at 250℃;

...Expand

: 2716-23-6
bicyclo[2.2.2]octan-2-one

A: 931-64-6
norbornene

B: 285-43-8
tricyclo<3.2.1.0.2.7>octane

Conditions

Conditions	Yield
With pyrographite at -196.15℃;

: 2,2-dibromo-bicyclo[2.2.2]octane

A: 931-64-6
norbornene

B: 285-43-8
tricyclo<3.2.1.0.2.7>octane

Conditions

Conditions	Yield
With methyllithium at 65℃;

: C15H20N2O2S

A: 931-64-6
norbornene

B: 285-43-8
tricyclo<3.2.1.0.2.7>octane

Conditions

Conditions	Yield
at 25℃; Photolysis;

: 13367-29-8
bicyclo[4.2.0]oct-2-ene

: 931-64-6
norbornene

Conditions

Conditions	Yield
at 300℃; Kinetics;

: 13367-29-8, 22567-94-8, 56029-14-2
bicyclo[4.2.0]oct-2-ene

A: 74-85-1
ethene

B: 931-64-6
norbornene

C: 1165952-91-9
cyclohexa-1,3-diene

Conditions

Conditions	Yield
at 275℃; Kinetics; Further Variations:; Temperatures;

...Expand

: 2716-23-6
bicyclo[2.2.2]octan-2-one

: 931-64-6
norbornene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.99 g / methanol 2: 99 percent Chromat. / MeLi; TMEDA / diethyl ether / cooling View Scheme
Multi-step reaction with 2 steps 1: 68 percent / methanol 2: 99 percent / MeLi; TMEDA View Scheme

: 68908-13-4, 2220-40-8, 16196-15-9, 68069-67-0
bicyclo[2.2.2]oct-5-en-2-one

: 931-64-6
norbornene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: H2 / Pd/C / ethanol / 2 h 2: 0.99 g / methanol 3: 99 percent Chromat. / MeLi; TMEDA / diethyl ether / cooling View Scheme

: 1165952-91-9
cyclohexa-1,3-diene

: 931-64-6
norbornene

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 6.9 g / hydroquinone / 90 - 100 °C 2: KOH / dimethylsulfoxide; H2O / 20 h 3: H2 / Pd/C / ethanol / 2 h 4: 0.99 g / methanol 5: 99 percent Chromat. / MeLi; TMEDA / diethyl ether / cooling View Scheme
Multi-step reaction with 4 steps 1.2: 17 percent / KOH / H2O; dimethylsulfoxide 2.1: 89 percent / H2 / Pd/C 3.1: 68 percent / methanol 4.1: 99 percent / MeLi; TMEDA View Scheme

: 2-chlorobicyclo<2.2.2>oct-5-ene-2-carbonitrile

: 931-64-6
norbornene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: KOH / dimethylsulfoxide; H2O / 20 h 2: H2 / Pd/C / ethanol / 2 h 3: 0.99 g / methanol 4: 99 percent Chromat. / MeLi; TMEDA / diethyl ether / cooling View Scheme

: 68069-67-0
(1S,4S)-(-)-bicyclo<2.2.2>oct-5-en-2-one

: 931-64-6
norbornene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 89 percent / H2 / Pd/C 2: 68 percent / methanol 3: 99 percent / MeLi; TMEDA View Scheme

: 6688-07-9, 19245-72-8, 55320-40-6, 68069-65-8, 68069-66-9, 70981-36-1, 74958-54-6, 123001-31-0
5-hydroxybicyclo[2.2.2]oct-2-ene

: 931-64-6
norbornene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: 83 percent / LiBEt3H / tetrahydrofuran / 4 h / 60 °C View Scheme

: 1165952-91-9
cyclohexa-1,3-diene

(methoxyphenylcarbene)molybdenum complex (22): (methoxyphenylcarbene)molybdenum complex (22)

: 931-64-6
norbornene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 2.) aq. NaOH, aq. H2O2 / 1.) room temp., 1 h, 2.) THF, 1 h, 50 deg C 2: pyridine 3: 83 percent / LiBEt3H / tetrahydrofuran / 4 h / 60 °C View Scheme

: 931-64-6
norbornene

A: 272-21-9
3H-benzo-1,2-dithiole

B: 130094-83-6, 130147-95-4
3,4,5-Trithia-tricyclo[5.2.2.02,6]undecane

Conditions

Conditions	Yield
With BPTC In dimethyl sulfoxide at 150℃; for 12h;	A 97% B 98%

: 931-64-6
norbornene

: 280-33-1
bicyclo[2,2,2]octane

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In hexane at 20 - 22℃;	97%
With magnesium; palladium on activated charcoal In methanol Ambient temperature;	96%
With hydrazine hydrate In ethanol for 24h; Reflux;	42%

: 931-64-6
norbornene

: 61382-45-4
(E)-1-iodo-3,3-dimethyl-1-butene

: (R)-2-((E)-3,3-Dimethyl-but-1-enyl)-bicyclo[2.2.2]octane

Conditions

Conditions	Yield
With tetrabutyl-ammonium chloride; potassium formate; palladium diacetate In N,N-dimethyl-formamide at 25℃; for 24h;	96%

: 931-64-6
norbornene

: 35572-83-9
α,α-diphenylbenzenemethanesulfenyl chloride

: endo-2-chloro-exo-1-(triphenylmethyldithio)bicyclo<2.2.2>octane

Conditions

Conditions	Yield
In dichloromethane for 20h; Ambient temperature;	87%

: 931-64-6
norbornene

: 108-98-5
thiophenol

: 92865-78-6
3-(phenylthio)bicyclo[2.2.2]octane

Conditions

Conditions	Yield
at 75 - 80℃; for 0.5h;	85.6%

: 931-64-6
norbornene

: 145964-29-0
(S)-Bicyclo[2.2.2]oct-2-yl-trichloro-silane

Conditions

Conditions	Yield
With trichlorosilane; (Ra)-(2'-methoxy-[1,1']-binaphthalenyl-2-yl)-diphenylphosphine; bis(η3-allyl-μ-chloropalladium(II)) at 0℃; for 24h;	85%

: 4387-36-4
2-iodobenzonitrile

: 931-64-6
norbornene

: C15H16O

Conditions

Conditions	Yield
With palladium diacetate; tetrabutyl-ammonium chloride; triethylamine In N,N-dimethyl-formamide at 100℃; for 48h;	82%

: 91547-45-4
cis-bis(acetonitrile)chloronitropalladium(II)

: 931-64-6
norbornene

: 91443-53-7
[Pd(N(O)OCH(CH(CH2CH2)2CH)CH)Cl]2

Conditions

Conditions	Yield
In acetone under N2, alkene added to soln. of Pd complex in acetone, reacted for 5-10 min; ppt. sepd., washed with acetone, dried overnight in vac.;	80%

: 82582-67-0, 72414-17-6
[Ir(hydrido)2(acetone)2(triphenylphosphine)2](BF4)

: 931-64-6
norbornene

: 79792-66-8
Ir(C8H10){(C6H5)3P}2(1+)*BF4(1-)

Conditions

Conditions	Yield
In dichloromethane reflux, 4h, under N2; the cooled soln. was reduced to 5 mL in vac. and Et2O was added until a solid had pptd., recrystn. from CH2Cl2/Et2O, elem. anal.;	78%

: 931-64-6
norbornene

: 72444-00-9, 90085-73-7, 130985-93-2
trans-2,3-dibromobicyclo<2.2.2>octane

Conditions

Conditions	Yield
With bromine In pyridine; chloroform at -40℃;	72.3%

: 931-64-6
norbornene

: 18684-63-4
bicyclo[2.2.2]octan-2-ol

Conditions

Conditions	Yield
With dimethylsulfide borane complex; dihydrogen peroxide In diethyl ether	70%
With sodium tetrahydroborate; boron trifluoride diethyl etherate In diethylene glycol dimethyl ether

: 931-64-6
norbornene

: 24165-03-5
tritylsulfenyl chloride

: endo-2-chloro-exo-1-(triphenylmethyldithio)bicyclo<2.2.2>octane

Conditions

Conditions	Yield
Ambient temperature;	65%
In dichloromethane for 20h; Ambient temperature;	43%

: 186581-53-3, 908094-01-9
diazomethane

: 931-64-6
norbornene

: 278-80-8
tricyclo<3.2.2.02,4>nonane

Conditions

Conditions	Yield
palladium(II) acetylacetonate In diethyl ether at -10℃;	64%

: 931-64-6
norbornene

: 151-50-8
potassium cyanide

: 143168-90-5
tert-Butyl-[(S)-1-((Z)-2-iodo-vinyl)-hexyloxy]-dimethyl-silane

: 143088-08-8
3-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-bicyclo[2.2.2]octane-2-carbonitrile

Conditions

Conditions	Yield
palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 80℃;	63%

...Expand

: 615-37-2
ortho-methylphenyl iodide

: 931-64-6
norbornene

: 5-methyl-1,2,3,4,4a,8b-hexahydro-1,4-cis,exo-ethanobiphenylene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 105℃; for 24h;	62%

: 931-64-6
norbornene

: 84-11-7
9,10-phenanthrenequinone

: 76036-59-4
C22H20O2

Conditions

Conditions	Yield
In benzene for 40h; Irradiation;	53%

: 533-58-4
2-Iodophenol

: 931-64-6
norbornene

: 1,4-ethano-1,2,3,4,4a,9b-hexahydrodibenzofuran

Conditions

Conditions	Yield
With palladium diacetate; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	52%

: 931-64-6
norbornene

: 33746-54-2
bicyclo<2.2.2>octane-cis-2,3-diol

Conditions

Conditions	Yield
With potassium permanganate; sodium hydroxide In methanol; water; toluene at 5℃;	46%
With potassium permanganate; acetone
With pyridine; osmium(VIII) oxide; diethyl ether Behandeln des Reaktionsprodukts mit Mannit und wss. KOH in CH2Cl2;

: 3437-95-4
2-Iodothiophene

: 931-64-6
norbornene

: (S)-2-Bicyclo[2.2.2]oct-2-yl-thiophene

Conditions

Conditions	Yield
With tetrabutyl-ammonium chloride; potassium formate; palladium diacetate In N,N-dimethyl-formamide at 25℃; for 24h;	39%

: 591-50-4
iodobenzene

: 931-64-6
norbornene

: 1,2,3,4,4a,8b-hexahydro-5-phenyl-1,4-ethanobiphenylene

B: 1,2,3,4,4a,12b-hexahydro-8-phenyl-1,4-ethanotriphenylene

: 1,2,3,4,4a,8b-hexahydro-5-<2'-(3'-phenyl)bicyclo<2.2.2>octyl>-1,4-ethanobiphenylene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	A 18% B 34% C 21%

...Expand

: 931-64-6
norbornene

: 130094-83-6, 130147-95-4
3,4,5-Trithia-tricyclo[5.2.2.02,6]undecane

Conditions

Conditions	Yield
With S2	15%

: 888965-55-7
tert-butyl (2E,4Z)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)penta-2,4-dienoate

: 931-64-6
norbornene

: (Z)-(2S,3R,4R)-4-Tricyclo[3.2.2.02,4]non-3-yl-but-3-enoic acid tert-butyl ester

Conditions

Conditions	Yield
With potassium fluoride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane; water at 80℃; for 3h;	15%
With potassium fluoride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;	15%

: 931-64-6
norbornene

: 619-81-8
cis-cyclohexane-1,4-dicarboxylic acid

Conditions

Conditions	Yield
With dihydrogen peroxide In methanol; formic acid; water; ethyl acetate	13%
With dihydrogen peroxide In methanol; formic acid; water; ethyl acetate	13%
With dihydrogen peroxide In methanol; formic acid; water; ethyl acetate	13%
Multi-step reaction with 2 steps 1: (i) aq. H2O2, HCO2H, Et2O, (ii) LiAlH4 2: CrO3, aq. H2SO4 / acetone View Scheme

: 931-64-6
norbornene

: 2243-67-6
naphthalene-2,6-diamine

: 2,6-bis(1-methylethyl)benzaldehyde

: C52H58N2

Conditions

Conditions	Yield
Stage #1: norbornene; naphthalene-2,6-diamine; 2,6-bis(1-methylethyl)benzaldehyde With boron trifluoride diethyl etherate In dichloromethane for 80h; Reflux; Stage #2: With manganese(IV) oxide In 1,2-dichloro-benzene for 16h; Reflux;	9%

...Expand

: 105-65-7
diisopropyl xanthogen disulfide

: 931-64-6
norbornene

: exo-3,5-dithiatricyclo<6.2.1.02,6>undecan-4-one

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene for 12h; Heating;	3%

: 591-87-7
Allyl acetate

: 931-64-6
norbornene

: 2-methylene-3-vinyl-bicyclo[2.2.2]octane

Conditions

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 80℃; Cycloaddition;	3%

Bicyclo(2,2,2)-2-octene Specification

The Bicyclo(2,2,2)-2-octene is an organic compound with the formula C₈H₁₂. The IUPAC name of this chemical is bicyclo[2.2.2]oct-2-ene. With the CAS registry number 931-64-6, it is also named as 2,2,2-Bicyclo-2-octene.

Physical properties about Bicyclo(2,2,2)-2-octene are: (1)ACD/LogP: 3.31; (2)ACD/LogD (pH 5.5): 3.31; (3)ACD/LogD (pH 7.4): 3.31; (4)ACD/BCF (pH 5.5): 194.03; (5)ACD/BCF (pH 7.4): 194.03; (6)ACD/KOC (pH 5.5): 1511.03; (7)ACD/KOC (pH 7.4): 1511.03; (8)Index of Refraction: 1.506; (9)Molar Refractivity: 34.54 cm³; (10)Molar Volume: 116.2 cm³; (11)Polarizability: 13.69×10^-24cm³; (12)Surface Tension: 33.8 dyne/cm; (13)Density: 0.93 g/cm³; (14)Flash Point: 18.5 °C; (15)Enthalpy of Vaporization: 36.01 kJ/mol; (16)Boiling Point: 138.3 °C at 760 mmHg; (17)Vapour Pressure: 8.41 mmHg at 25°C.

Preparation: this chemical can be prepared by 5-benzenesulfonyl-bicyclo[2.2.2]oct-2-ene. This reaction will need reagent 6 percent sodium amalgam, Na₂HPO₄ and solvent tetrahydrofuran, methanol. The reaction time is 3.5 hours. The yield is about 78.5%.

Uses of Bicyclo(2,2,2)-2-octene: it can be used to produce bicyclo[2.2.2]octane. It will need reagent Raney nickel.

You can still convert the following datas into molecular structure:
(1)SMILES: C\1=C\C2CCC/1CC2
(2)InChI: InChI=1/C8H12/c1-2-8-5-3-7(1)4-6-8/h1-2,7-8H,3-6H2
(3)InChIKey: VIQRCOQXIHFJND-UHFFFAOYAH
(4)Std. InChI: InChI=1S/C8H12/c1-2-8-5-3-7(1)4-6-8/h1-2,7-8H,3-6H2
(5)Std. InChIKey: VIQRCOQXIHFJND-UHFFFAOYSA-N

Product Name

2,2,2-BICYCLO-2-OCTENE

Synthetic route

Bicyclo(2,2,2)-2-octene Specification

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