5-Dibenzosuberenone supplier

Name
5-Dibenzosuberenone
EINECS 218-737-3
CAS No. 2222-33-5
Article Data64
CAS DataBase
Density 1.188 g/cm³
Solubility Soluble in chloroform, ethyl acetate. Insoluble in water.
Melting Point 87-88 °C(lit.)
Formula C₁₅H₁₀O
Boiling Point 363.9 °C at 760 mmHg
Molecular Weight 206.244
Flash Point 160.2 °C
Transport Information
Appearance white to pale yellow or beige crystalline powder
Safety 24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2,3:6,7-Dibenzotropone;5H-Dibenzo[a,d]cycloheptenone;Dibenzo[a,d]cyclohepten-5-one;Dibenzosuberenone;NSC 86151;dibenzo[a,b]cyclohepten-5-one;
PSA 17.07000
LogP 3.35320

Synthetic route

: 39654-52-9
trans-10,11-dibromo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With sodium selenite; rac-cysteine In tetrahydrofuran; water at 0℃; for 0.0833333h;	99%
With dimethyl sulfoxide at 75℃; for 2h;	98%
With hydrogenchloride; samarium In tetrahydrofuran for 0.166667h; Ambient temperature;	96%

: 57295-97-3
10,11-dibromo[(10,11-dihydro-5H-dibenzo[a,d]cyclohept-5-one)]

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; sexithiophene In N,N-dimethyl-formamide for 1h; Inert atmosphere; Irradiation;	99%
With sodium hydride; 2,8,9-trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane hydro-chloride In [D3]acetonitrile for 2h;	92%

: 10354-00-4
5H-dibenzo[a,d]cyclohepten-5-ol

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With Merrifield's resin-bound N-aminoimidazolium chlorochromate In dichloromethane for 2.5h; Heating;	95%
With tert.-butylhydroperoxide In water at 100℃; for 24h;	91%
Stage #1: 5H-dibenzo[a,d]cyclohepten-5-ol With 7,7-dichlorocyclohepta-1,3,5-triene In dichloromethane; dimethyl sulfoxide at -30℃; for 0.333333h; Swern Oxidation; Inert atmosphere; Stage #2: With triethylamine In dichloromethane; dimethyl sulfoxide at -30 - 20℃; for 0.333333h; Swern Oxidation; Inert atmosphere;	88%

: 39654-52-9, 57295-97-3, 123835-95-0
trans-10,11-dibromodibenzosuberenone

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With indium; niobium pentachloride In tetrahydrofuran at 20℃; for 0.166667h; Sonication; chemoselective reaction;	95%
With indium; cobalt(II) chloride hexahydrate In methanol at 20℃; for 1h;	94%
With gallium; bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran at 20℃; for 0.416667h; Inert atmosphere; Ultrasonic irradiation; chemoselective reaction;	92%

: 1087-68-9
5,5-dimethoxy-5H-dibenzocycloheptene

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With dimethylboron bromide In dichloromethane; 1,2-dichloro-ethane at -78℃; for 1h;	93%
With dimethylboron bromide; sodium hydrogencarbonate 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction;

: 101023-29-4
5-(3,3-diphenyl-2,3-dihydro-2-oxoindol-1-yl)dibenzocyclohepten-1-yl diphenylethanoate

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With hydrogenchloride; water In acetic acid for 1h; Heating;	83%

: 4444-44-4
10,11-epoxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-one

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With indium; indium chloride In water; tert-butyl alcohol at 84℃; for 6h;	81%

: 16203-85-3
5-Allyl-dibenzo-cyclohepten-5-ol

: C19H18O

B: 17044-52-9
9.18-Dioxo-4b.4c.9.13b.13c.18-hexahydro-tetrabenzocyclobutadicyclohepten

C: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 2h; Inert atmosphere; Photolysis;	A 81% B 6% C 8%

...Expand

: 55090-29-4
5-phenyl-5H-dibenzocyclohepten-5-ol

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; acetic acid for 4h; Ambient temperature;	79%

: 35066-77-4
5-<(5H-dibenzocyclohepten-5-yl)oxy>-5H-dibenzocycloheptene

A: 256-81-5
suberene

B: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With iodine In neat (no solvent) at 85℃;	A 73% B 79%

: 1210-35-1
10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With bromine at 140℃;	70%
With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide Erhitzen des Reaktionsprodukts mit Triaethylamin;
With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide Erhitzen des Reaktionsprodukts mit Pyridin;

: 16203-85-3
5-Allyl-dibenzo-cyclohepten-5-ol

: C19H18O

B: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 2h; Inert atmosphere; Photolysis;	A 68% B 25%

: 101023-28-3
5-(3,3-dimethyl-2,3-dihydro-2-oxoindol-1-yl)dibenzocyclohepten-1-yl 2-methylpropanoate

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With hydrogenchloride; water In acetic acid for 0.5h; Heating;	51%

: C34H28O2

A: 17044-52-9
9.18-Dioxo-4b.4c.9.13b.13c.18-hexahydro-tetrabenzocyclobutadicyclohepten

B: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 2h; Solvent; Inert atmosphere; Photolysis;	A 12% B 50%

: 1210-34-0
dibenzosuberol

A: 256-81-5
suberene

B: 120-12-7
anthracene

C: 779-02-2
9-methylanthracene

D: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With quartz at 350 - 650℃; Inert atmosphere; Pyrolysis;	A 20% B 15% C 12% D 40%

...Expand

: C34H28O2

A: 15224-49-4
5,5'-bi(5H-dibenzocycloheptenyl)

B: C30H22

C: 17044-52-9
9.18-Dioxo-4b.4c.9.13b.13c.18-hexahydro-tetrabenzocyclobutadicyclohepten

D: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 2h; Solvent; Inert atmosphere; Photolysis;	A 8% B 6% C 22% D 39%
In ethyl acetate at 20℃; for 2h; Inert atmosphere; Photolysis;	A 14% B 8% C 38% D 20%

...Expand

: 6141-56-6
5-diazo-5H-dibenzocycloheptene

A: 256-81-5
suberene

B: 203-64-5
4H-Cyclopenta[def]phenanthrene

C: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
at 450℃; under 1E-05 Torr;	A n/a B 17% C n/a
at 450℃; under 1E-05 Torr; Mechanism;	A n/a B 17% C n/a

...Expand

: 256-81-5
suberene

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With 1,4-dioxane; selenium(IV) oxide

: cis-stilbene-2-carbonyl chloride

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With aluminium trichloride

: 67-56-1
methanol

: 6141-56-6
5-diazo-5H-dibenzocycloheptene

A: 55789-73-6
5-methoxy-5H-dibenzocycloheptene

B: 1087-68-9
5,5-dimethoxy-5H-dibenzocycloheptene

C: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
at 60℃; electrooxidation;	A 56.6 % Spectr. B 30.2 % Spectr. C 7.1 % Spectr.
at 60℃; electrooxidation;	A n/a B 30.2 % Spectr. C n/a

...Expand

: 67-56-1
methanol

: 109217-78-9
C15H10N2(1+)

A: 55789-73-6
5-methoxy-5H-dibenzocycloheptene

B: 1087-68-9
5,5-dimethoxy-5H-dibenzocycloheptene

C: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With tetramethylammonium tetrafluoroborate In acetonitrile at 0 - 50℃; Kinetics; Thermodynamic data; electrolyte effect, substrate concentration, effect of solvent, deuterated solvent (in methanol), ΔH(excit.), ΔS(excit.);

...Expand

: 6141-56-6
5-diazo-5H-dibenzocycloheptene

A: 55789-73-6
5-methoxy-5H-dibenzocycloheptene

B: 1087-68-9
5,5-dimethoxy-5H-dibenzocycloheptene

C: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
In methanol at 60℃; electrooxidation;	A 56.6 % Spectr. B 30.2 % Spectr. C 7.1 % Spectr.

...Expand

: (10S,11S)-10,11-Dichloro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-one

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With 1,5-diselenacyclooctane In chloroform at 90℃; for 95h;	28 % Chromat.

: 3594-99-8
5H-6,7-dihydrodibenzo[a,c]cyclohepten-6-ol

A: 256-81-5
suberene

B: 120-12-7
anthracene

C: 779-02-2
9-methylanthracene

D: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
at 350℃; under 997.58 Torr; Product distribution; Further Variations:; Temperatures; other dibenzocycloalkanols;	A 15 % Spectr. B 4 % Spectr. C 4 % Spectr. D 20 % Spectr.

...Expand

: 833-48-7
dibenzosuberane

A: 1210-35-1
10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one

B: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
With aluminum oxide; Ru(OH)x; oxygen In 1,2-dichloro-benzene at 169.85℃; under 760 Torr; for 5h;

: 61047-37-8
5H-dibenzocyclohepten-5-one hydrazone

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) sodium sulphate, yellow mercuric oxide, potassium hydroxide, Celite / 1.) diethyl ether, ethanol, 3 h, 2.) ethanol, diethyl ether, room temp., overnight 2: 82 percent / benzene / 8 h / Ambient temperature 3: 83 percent / water, hydrochloric acid / acetic acid / 1 h / Heating View Scheme

: 101023-27-2
dibenzocyclohepten-5-ylidene(phenyl)amine N-oxide

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / benzene / 8 h / Ambient temperature 2: 83 percent / water, hydrochloric acid / acetic acid / 1 h / Heating View Scheme

: 4890-85-1
o-phenethylbenzoic acid

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: polyphosphoric acid 2: bromine / Irradiation View Scheme

: 36795-27-4
diphenylethane-2-carboxylic acid chloride

: 2222-33-5
dibenzosuberenon

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3; CS2 2: N-bromo-succinimide; CCl4; dibenzoyl peroxide / Erhitzen des Reaktionsprodukts mit Triaethylamin View Scheme

: 2222-33-5
dibenzosuberenon

: 833-48-7
dibenzosuberane

Conditions

Conditions	Yield
With iodine; hypophosphorous acid In acetic acid for 72h; Reduction; Heating;	100%
With potassium hydroxide; Raney Ni-Al alloy In water at 90℃; for 8h;	92%
With ethanol; platinum Hydrogenation;
With ethanol; sodium

: 74-89-5
methylamine

: 2222-33-5
dibenzosuberenon

: 59864-52-7
N-methyl-5H-dibenzocyclohepten-5-imine

Conditions

Conditions	Yield
With titanium tetrachloride In toluene at -10 - 20℃; Inert atmosphere;	100%
With titanium tetrachloride In benzene for 144h; Ambient temperature;	95%
With titanium tetrachloride In toluene

: 2222-33-5
dibenzosuberenon

: 1021-91-6
N-[tricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,9,12,14-heptaen-2-ylidene]hydroxylamine

Conditions

Conditions	Yield
With hydroxylamine hydrochloride In pyridine for 20h; Reflux; Inert atmosphere;	100%
With pyridine; hydroxylamine hydrochloride for 15.5h; Reflux;	100%
With pyridine; hydroxylamine hydrochloride In ethanol Reflux;	98%

: 2222-33-5
dibenzosuberenon

: 256-81-5
suberene

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; aluminium trichloride In tetrahydrofuran; diethyl ether	99%
With lithium aluminium tetrahydride; aluminium trichloride In diethyl ether	65%
With aluminum isopropoxide at 250℃; for 0.166667h;	50%
With potassium hydroxide; hydrazine hydrate; isopropyl alcohol Reagens 4: Propan-1,3-dion; Abdestillieren des Loesungsmittels und Erhitzen auf 200grad;
With lithium aluminium tetrahydride; aluminium trichloride In tetrahydrofuran; diethyl ether for 2h; Heating; Yield given;

: 5570-77-4
4-chloro-1-methylpiperidine

: 2222-33-5
dibenzosuberenon

: 3967-32-6
5-(1-methyl-4-piperidyl)-5H-dibenzocyclohepten-5-ol

Conditions

Conditions	Yield
Stage #1: 4-chloro-1-methylpiperidine With iodine; magnesium In tetrahydrofuran for 5h; Reflux; Inert atmosphere; Stage #2: With (trimethylsilyl)methylmagnesium chloride; lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether at 20℃; for 0.75h; Inert atmosphere; Stage #3: dibenzosuberenon In tetrahydrofuran; diethyl ether at 0℃; for 2h; Inert atmosphere;	99%
Stage #1: 4-chloro-1-methylpiperidine With magnesium In tetrahydrofuran at 60 - 65℃; for 1h; Inert atmosphere; Large scale; Stage #2: dibenzosuberenon In tetrahydrofuran at 5 - 20℃; for 1h; Temperature; Inert atmosphere; Large scale;

: 497-19-8
sodium carbonate

: 2222-33-5
dibenzosuberenon

: 573-32-0
benzophenone-2,2'-dicarboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride; potassium permanganate In water; acetone at 20℃; for 24h;	99%

: 2222-33-5
dibenzosuberenon

: 10354-00-4
5H-dibenzo[a,d]cyclohepten-5-ol

Conditions

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate In methanol; water	98%
With sodium borohydrid In diethyl ether; water	98%
With sodium borohydrid In diethyl ether; water	98%

: 2222-33-5
dibenzosuberenon

: 76858-21-4
dibenzocyclohepten-5-imine

Conditions

Conditions	Yield
With 1,1,1,3,3,3-hexamethyl-disilazane; scandium tris(trifluoromethanesulfonate) In chlorobenzene at 90℃; for 12h; Inert atmosphere;	98%
With ammonia; titanium tetrachloride In toluene at 25℃; for 16h;	93%
With ammonia; titanium tetrachloride In toluene at 0 - 25℃; for 12.25h;	80.4%
With ammonia; titanium tetrachloride In toluene at 25℃; overnight;	20.6 g
With ammonia; titanium tetrachloride In toluene

: 108-86-1
bromobenzene

: 2222-33-5
dibenzosuberenon

: 55090-29-4
5-phenyl-5H-dibenzocyclohepten-5-ol

Conditions

Conditions	Yield
Stage #1: bromobenzene With magnesium In tetrahydrofuran for 0.333333h; Stage #2: dibenzosuberenon In tetrahydrofuran for 0.5h; Heating;	97%
With magnesium 1) Et2O, 2) Et2O, 2a) reflux, 2 h, 2b) r. t., 2 h; Yield given. Multistep reaction;

: 75-16-1
methylmagnesium bromide

: 2222-33-5
dibenzosuberenon

: 18259-45-5
5-hydroxy-5-methyl-5H-dibenzocycloheptene

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether Ambient temperature;	97%
In tetrahydrofuran; diethyl ether at 15 - 20℃; for 2h;	83%
In diethyl ether for 1h; Heating;	71%

: 143192-60-3
2-(phenylethynyl)phenylacetylene

: 2222-33-5
dibenzosuberenon

: 372967-65-2
5-[[2-(phenylethynyl)phenyl]ethynyl]-5H-dibenzo[a,d]cyclohepten-5-ol

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 2.5h;	97%

: 2052-07-5
2-Bromobiphenyl

: 2222-33-5
dibenzosuberenon

: 121472-88-6
spiro-fluorene-dibenzosuberene

Conditions

Conditions	Yield
Stage #1: 2-Bromobiphenyl; dibenzosuberenon With n-butyllithium In tetrahydrofuran at -78 - 20℃; Stage #2: With hydrogenchloride; acetic acid In water for 0.333333h; Heating;	97%
Stage #1: 2-Bromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: dibenzosuberenon In tetrahydrofuran; hexane for 6h; Stage #3: With hydrogenchloride; acetic acid In water for 12h; Reflux;	94%
Stage #1: 2-Bromobiphenyl; dibenzosuberenon With tert.-butyl lithium In tetrahydrofuran; hexane at -78℃; for 6.5h; Stage #2: With hydrogenchloride; acetic acid In water for 12h; Reflux;	94%
Stage #1: 2-Bromobiphenyl In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: dibenzosuberenon In tetrahydrofuran; hexane for 6h; Stage #3: With hydrogenchloride; acetic acid In water for 12h; Reflux;	94%

: 4110-02-5
tris(trimethylsilyl)silyllithium

: 2222-33-5
dibenzosuberenon

: 8-bis(trimethylsilyl)-5(5-hydroxy-dibenzo[a,d]cyclohepten-5-yl)-1-trimethylsiloxy-4,5-dihydro-dibenzo[a,d]-8-silabicyclo[3,2,1]octane

Conditions

Conditions	Yield
In 1,2-dimethoxyethane -78 deg C to rt;	96%

: 1671-87-0
3,6-di(2'-pyridyl)-1,2,4,5-tetrazine

: 2222-33-5
dibenzosuberenon

: 1,4-di(pyridin-2-yl)-2,4a-dihydro-9H-dibenzo[3,4:6,7]cyclohepta[1,2-d]pyridazin-9-one

Conditions

Conditions	Yield
In toluene at 120℃; for 10h; Diels-Alder Cycloaddition; Sealed tube;	96%
In toluene at 120℃; for 20h; Diels-Alder Cycloaddition;	94%

: 57654-36-1
3,6-di(pyridin-4-yl)-1,2,4,5-tetrazine

: 2222-33-5
dibenzosuberenon

: 1,4-di(pyridin-4-yl)-2,4a-dihydro-9H-dibenzo[3,4:6,7]cyclohepta[1,2-d]pyridazin-9-one

Conditions

Conditions	Yield
In toluene at 125℃; for 16h; Diels-Alder Cycloaddition; Sealed tube;	96%

: 2222-33-5
dibenzosuberenon

: 39654-52-9
trans-10,11-dibromo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

Conditions

Conditions	Yield
With bromine In tetrachloromethane	95%
With bromine In tetrachloromethane for 1.5h;	90%
With bromine In chloroform at 0 - 20℃; Inert atmosphere;	74%

: 2222-33-5
dibenzosuberenon

: 57295-97-3
10,11-dibromo[(10,11-dihydro-5H-dibenzo[a,d]cyclohept-5-one)]

Conditions

Conditions	Yield
With bromine In tetrachloromethane for 5.25h;	95%
With bromine In tetrachloromethane at 20℃; for 1.5h;	92%
With bromine In tetrachloromethane at 20℃; for 1.5h;	92%
With bromine In acetic acid

: 2222-33-5
dibenzosuberenon

: 59864-52-7
N-methyl-5H-dibenzocyclohepten-5-imine

Conditions

Conditions	Yield
With methylamine; titanium tetrachloride In benzene	95%

: 2222-33-5
dibenzosuberenon

: 1730-25-2
allylmagnesium bromide

: 16203-85-3
5-Allyl-dibenzo-cyclohepten-5-ol

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	95%

: 2222-33-5
dibenzosuberenon

: [15N]-5H-dibenzo[a,d]cyclohepten-5-one oxime

Conditions

Conditions	Yield
With pyridine; [15N]hydroxylamine hydrochloride for 16h; Reflux;	95%

: 2166-14-5
1,2,4,5-tetrazine-3,6-dicarboxylic acid dimethyl ester

: 2222-33-5
dibenzosuberenon

: dimethyl-9-oxo-4a,9-dihydro-2H-dibenzo[3,4:6,7]cyclohepta[1,2-d]pyridazin-1,4-dicarboxylate

Conditions

Conditions	Yield
In toluene at 120℃; for 8h; Diels-Alder Cycloaddition;	95%
In toluene at 100℃; for 10h; Diels-Alder Cycloaddition; Sealed tube;	95%

: 36743-38-1
1,2,4,5-tetrazine-3,6-dicarboxamide

: 2222-33-5
dibenzosuberenon

: 9-oxo-4a,9-dihydro-2H-dibenzo[3,4:6,7]cyclohepta[1,2-d]pyridazine-1,4-dicarboxamide

Conditions

Conditions	Yield
In neat (no solvent) at 100℃; for 16h; Diels-Alder Cycloaddition; Sealed tube;	95%

: 2222-33-5
dibenzosuberenon

: 61047-37-8
5H-dibenzocyclohepten-5-one hydrazone

Conditions

Conditions	Yield
With hydrazine hydrochloride; hydrazine hydrate In various solvent(s) Heating;	94%
Multi-step reaction with 2 steps 1: Lawessons reagent / benzene / 24 h / Reflux 2: hydrazine hydrate / benzene; ethanol / 2 h / Reflux View Scheme

: 920-39-8
isopropylmagnesium bromide

: 2222-33-5
dibenzosuberenon

A: 10354-00-4
5H-dibenzo[a,d]cyclohepten-5-ol

B: 123299-71-8
5-isopropyl-5H-dibenzo[a,d]cyclohepten-5-ol

Conditions

Conditions	Yield
Stage #1: isopropylmagnesium bromide With (trimethylsilyl)methylmagnesium chloride; lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether at 20℃; Grignard addition; Stage #2: dibenzosuberenon In tetrahydrofuran; diethyl ether at 0℃; for 3h; Grignard addition;	A 6% B 94%
Stage #1: isopropylmagnesium bromide With (trimethylsilyl)methylmagnesium chloride; lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether at 20℃; for 0.75h; Inert atmosphere; Stage #2: dibenzosuberenon In tetrahydrofuran; diethyl ether at 0℃; for 3h; Inert atmosphere;	A 6% B 94%
In tetrahydrofuran at 0℃; Grignard addition;	A 89% B 11%

...Expand

: 41003-94-5
diethyl isocyanomethylphosphonate

: 2222-33-5
dibenzosuberenon

: 5-(isocyanomethylen)-5H-dibenzo[a,d]cycloheptene

Conditions

Conditions	Yield
Stage #1: diethyl isocyanomethylphosphonate With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Horner-Wadsworth-Emmons Olefination; Stage #2: dibenzosuberenon In tetrahydrofuran for 16h; Horner-Wadsworth-Emmons Olefination;	94%

5-Dibenzosuberenone Specification

The Dibenzosuberenone, with the CAS registry number 2222-33-5 and EINECS registry number 218-737-3, has the systematic name of 5H-dibenzo[a,d][7]annulen-5-one. It is a kind of white to pale yellow or beige crystalline powder, and belongs to the following product categories: Pharmaceutical Intermediates; API intermediates; intermediate of cyclobenzaprine, cyproheptadine; Others chemical reagents. And the molecular formula of the chemical is C₁₅H₁₀O. What's more, it is always used as intermediate of cyproheptadin hydrochloride.

The physical properties of Dibenzosuberenone are as followings: (1)ACD/LogP: 2.49; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.49; (4)ACD/LogD (pH 7.4): 2.49; (5)ACD/BCF (pH 5.5): 46.17; (6)ACD/BCF (pH 7.4): 46.17; (7)ACD/KOC (pH 5.5): 540.7; (8)ACD/KOC (pH 7.4): 540.7; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 17.07 Å²; (13)Index of Refraction: 1.642; (14)Molar Refractivity: 62.75 cm³; (15)Molar Volume: 173.6 cm³; (16)Polarizability: 24.87×10^-24cm³; (17)Surface Tension: 48.1 dyne/cm; (18)Density: 1.188 g/cm³; (19)Flash Point: 160.2 °C; (20)Enthalpy of Vaporization: 61 kJ/mol; (21)Boiling Point: 363.9 °C at 760 mmHg; (22)Vapour Pressure: 1.75E-05 mmHg at 25°C.

Uses of Dibenzosuberenone: It can react with bromoacetic acid ethyl ester to produce Aethyl-(5-hydroxy-5H-dibenzo[a.d]cyclohepten-5-yl)-acetat. This reaction will need reagent zinc, and the menstruum benzene. The reaction time is 4 hours with heating, and the yield is about 82%.

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Avoid contact with skin and eyes; Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C3c1ccccc1\C=C/c2c3cccc2
(2)InChI: InChI=1/C15H10O/c16-15-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)15/h1-10H
(3)InChIKey: SNVTZAIYUGUKNI-UHFFFAOYAC

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	180mg/kg (180mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02244,

Product Name

5-Dibenzosuberenone

Synthetic route

5-Dibenzosuberenone Specification

Related Products

Hot Products