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2235-15-6

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2235-15-6 Usage

Uses

1-Acenaphthenone is a product of the photolysis (and microbial metabolism) of acenaphthene, a polycyclic hydrocarbon that has potential to act as polyploidizing agents in plants.

Check Digit Verification of cas no

The CAS Registry Mumber 2235-15-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,2,3 and 5 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 2235-15:
(6*2)+(5*2)+(4*3)+(3*5)+(2*1)+(1*5)=56
56 % 10 = 6
So 2235-15-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H8O/c13-11-7-9-5-1-3-8-4-2-6-10(11)12(8)9/h1-6H,7H2

2235-15-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2H-acenaphthylen-1-one

1.2 Other means of identification

Product number -
Other names 2-Acenaphthenone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2235-15-6 SDS

2235-15-6Synthetic route

acenaphthylene
208-96-8

acenaphthylene

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With oxygen; isobutyraldehyde In acetonitrile at 60℃; for 3h;98%
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In fluorobenzene at 100℃; under 7500.6 Torr;87%
With iodosylbenzene; iron(III) tetraphenylporphyrin In dichloromethane for 1h;58%
With iodosylbenzene; μ-oxo dimer of iron(III)porphyrinate In methanol at 21.9℃; for 3h; Product distribution; Mechanism; catalysts also Fe(III)porphyrinate, Fe(III)tetraphenylporphyrinate; protic and aprotic solvents; inhibition effect by phenanthrene; by-products;28%
With dinitrogen monoxide at 300℃; under 367754 Torr;
1-acenaphthenol
6306-07-6

1-acenaphthenol

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With potassium dichromate; sulfuric acid In diethyl ether; water at 0℃; for 0.666667h;97%
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In 1,2-dichloro-ethane at 120℃; under 7600 Torr; for 7.5h;95%
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In 1,2-dichloro-ethane at 120℃; under 7500.6 Torr; for 7.5h;95%
1-acenaphthenol
6306-07-6

1-acenaphthenol

A

benzoic acid
65-85-0

benzoic acid

B

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With dibenzoyl peroxide In dichloromethane for 3h; Ambient temperature; Irradiation;A n/a
B 84%
acenaphthene
83-32-9

acenaphthene

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; V2O5/TiO2 In water at 80℃; for 8h; Sealed tube; Green chemistry;82%
With potassium permanganate; sulfuric acid; triethylamine In chloroform Ambient temperature;76%
With tetrakis(pyridine)silver(II) peroxodisulfate In acetonitrile for 1h; Heating;60%
acenaphthene quinone
82-86-0

acenaphthene quinone

A

decacyclene
191-48-0

decacyclene

B

2-hydroxyacenaphthylen-1-one
33928-29-9

2-hydroxyacenaphthylen-1-one

C

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With TiCl3-1,2-dimethoxyethane; copper; zinc In 1,2-dimethoxyethane for 1h; Heating;A n/a
B 80%
C 5%
1-formyl-2-(1-pyrrolidinyl)acenaphthylene
160771-19-7

1-formyl-2-(1-pyrrolidinyl)acenaphthylene

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 0.5h; Heating;62%
methanol
67-56-1

methanol

acenaphthene
83-32-9

acenaphthene

A

1-methoxyacenaphthene
21857-35-2

1-methoxyacenaphthene

B

1-acenaphthenol
6306-07-6

1-acenaphthenol

C

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; oxygen In water at 20℃; for 0.0833333h;A 14%
B 12%
C 59%
naphthalen-1-yl-acetyl chloride
5121-00-6

naphthalen-1-yl-acetyl chloride

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 20℃; for 3h;58%
With aluminium trichloride In carbon disulfide
With aluminum (III) chloride In carbon disulfide for 2h; Inert atmosphere; Reflux;
acenaphthene
83-32-9

acenaphthene

A

1-acenaphthenol
6306-07-6

1-acenaphthenol

B

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With N-hydroxyphthalimide; 1,4-diamino-2,3-dichloroanthraquinone; oxygen In acetonitrile at 80℃; under 1875.15 - 2250.18 Torr; for 10h;A 25 % Chromat.
B 54%
With N-hydroxyphthalimide; bromine; oxygen; acridine yellow In acetonitrile at 100℃; under 2250.18 Torr; for 24h;
With Cr2O4(2-)*Cu(2+); dihydrogen peroxide In acetonitrile at 50℃; for 10h;
1-hydroperoxy-1,2-dihydroacenaphthylene
119951-85-8

1-hydroperoxy-1,2-dihydroacenaphthylene

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With perchloric acid In methanol at 60℃; for 2h;50%
With sodium hydroxide In methanol; water at 30℃; Rate constant;
2-diazoacenaphthen-1-one
2008-77-7

2-diazoacenaphthen-1-one

A

1,1'-Bi(acenaphthen-1-ylidene)-2,2'-dione
24141-18-2

1,1'-Bi(acenaphthen-1-ylidene)-2,2'-dione

B

1,2-acenaphthenothiophene
203-42-9

1,2-acenaphthenothiophene

C

acenaphtho<1,2-c><1,2,3>thiadiazole

acenaphtho<1,2-c><1,2,3>thiadiazole

D

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With Lawessons reagent; N,N,N,N,N,N-hexamethylphosphoric triamide In benzene Heating;A 17%
B 12%
C 48%
D 13%
4-chloro-n-butyric anhydride
20496-01-9

4-chloro-n-butyric anhydride

acenaphthylene
208-96-8

acenaphthylene

A

acenaphthene
83-32-9

acenaphthene

B

1-Acenaphthen-1-yl-4-chloro-butan-1-one
88970-55-2

1-Acenaphthen-1-yl-4-chloro-butan-1-one

C

4-Chloro-butyric acid 1-[2H-acenaphthylen-(1Z)-ylidene]-4-chloro-butyl ester

4-Chloro-butyric acid 1-[2H-acenaphthylen-(1Z)-ylidene]-4-chloro-butyl ester

D

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given;A 6%
B 46%
C n/a
D 8.5%
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given;A 6%
B 46%
C 8.5%
D 8.5%
4-chloro-n-butyric anhydride
20496-01-9

4-chloro-n-butyric anhydride

acenaphthylene
208-96-8

acenaphthylene

A

acenaphthene
83-32-9

acenaphthene

B

1-Acenaphthen-1-yl-4-chloro-butan-1-one
88970-55-2

1-Acenaphthen-1-yl-4-chloro-butan-1-one

C

4-Chloro-butyric acid 1-[2H-acenaphthylen-(1E)-ylidene]-4-chloro-butyl ester

4-Chloro-butyric acid 1-[2H-acenaphthylen-(1E)-ylidene]-4-chloro-butyl ester

D

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given;A 6%
B 46%
C 3.5%
D 8.5%
acetic anhydride
108-24-7

acetic anhydride

acenaphthylene
208-96-8

acenaphthylene

A

acenaphthene
83-32-9

acenaphthene

B

Acetic acid 1-[2H-acenaphthylen-(1Z)-ylidene]-ethyl ester

Acetic acid 1-[2H-acenaphthylen-(1Z)-ylidene]-ethyl ester

C

Acetic acid 1-[2H-acenaphthylen-(1E)-ylidene]-ethyl ester

Acetic acid 1-[2H-acenaphthylen-(1E)-ylidene]-ethyl ester

D

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given;A 9%
B 43%
C 18%
D n/a
acenaphthene
83-32-9

acenaphthene

A

(R)-1,2-dihydroacenaphthylen-1-ol
6306-07-6, 92720-77-9, 121961-98-6, 121961-97-5

(R)-1,2-dihydroacenaphthylen-1-ol

B

(S)-(+)-1,2-dihydroacenaphthylen-1-ol
121961-98-6

(S)-(+)-1,2-dihydroacenaphthylen-1-ol

C

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With 5-chloro-4,9-(chlorobenzene-2,3-diyl)-2,4-dihydroxy-3a,4,9,9a-tetrahydro-1H-benzo[f]isoindole-1,3(2H)-dione; oxygen; cobalt(II) acetate In acetonitrile at 60℃; under 760.051 Torr; for 10h;A n/a
B n/a
C 35%
2-diazoacenaphthen-1-one
2008-77-7

2-diazoacenaphthen-1-one

A

1,8-Naphthalic anhydride
81-84-5

1,8-Naphthalic anhydride

B

1,1'-Bi(acenaphthen-1-ylidene)-2,2'-dione
24141-18-2

1,1'-Bi(acenaphthen-1-ylidene)-2,2'-dione

C

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With oxygen; isopropyl alcohol for 2h; Ambient temperature; Irradiation;A 25%
B 2%
C 24%
carbon dioxide
124-38-9

carbon dioxide

acenaphthylene
208-96-8

acenaphthylene

methyl iodide
74-88-4

methyl iodide

A

acenaphthene
83-32-9

acenaphthene

trans-1,2-dicarbomethoxy-1,2-dihydroacenaphthylene
5673-04-1, 5673-22-3, 51869-93-3, 56137-60-1, 93012-10-3

trans-1,2-dicarbomethoxy-1,2-dihydroacenaphthylene

C

Acetic acid 1-[2H-acenaphthylen-(1E)-ylidene]-ethyl ester

Acetic acid 1-[2H-acenaphthylen-(1E)-ylidene]-ethyl ester

D

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
1.) electrolysis at -1.7 V (0.1 M TBAI), DMF, -35 deg C; 2) overnight; Yield given. Multistep reaction. Further byproducts given;A 9%
B n/a
C 18%
D n/a
4-chloro-n-butyric anhydride
20496-01-9

4-chloro-n-butyric anhydride

acenaphthylene
208-96-8

acenaphthylene

A

Cyclopropanecarboxylic acid 1-[2H-acenaphthylen-(1Z)-ylidene]-4-chloro-butyl ester

Cyclopropanecarboxylic acid 1-[2H-acenaphthylen-(1Z)-ylidene]-4-chloro-butyl ester

B

4-Chloro-butyric acid [2H-acenaphthylen-(1E)-ylidene]-cyclopropyl-methyl ester

4-Chloro-butyric acid [2H-acenaphthylen-(1E)-ylidene]-cyclopropyl-methyl ester

C

4-Chloro-butyric acid 1-[2H-acenaphthylen-(1Z)-ylidene]-4-chloro-butyl ester

4-Chloro-butyric acid 1-[2H-acenaphthylen-(1Z)-ylidene]-4-chloro-butyl ester

D

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
In N,N-dimethyl-formamide electrolysis at -1.7 V (0.1 M TBAI); Further byproducts given;A 3%
B 4%
C 11%
D 8%
1,2-dihydroacenaphthylen-1-yl iodoacetate

1,2-dihydroacenaphthylen-1-yl iodoacetate

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
In acetonitrile for 5h; Irradiation;11%
4-Chloro-butyric acid 1-[2H-acenaphthylen-(1Z)-ylidene]-4-chloro-butyl ester

4-Chloro-butyric acid 1-[2H-acenaphthylen-(1Z)-ylidene]-4-chloro-butyl ester

A

Cyclopropanecarboxylic acid 1-[2H-acenaphthylen-(1Z)-ylidene]-4-chloro-butyl ester

Cyclopropanecarboxylic acid 1-[2H-acenaphthylen-(1Z)-ylidene]-4-chloro-butyl ester

B

4-Chloro-butyric acid [2H-acenaphthylen-(1E)-ylidene]-cyclopropyl-methyl ester

4-Chloro-butyric acid [2H-acenaphthylen-(1E)-ylidene]-cyclopropyl-methyl ester

C

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With acenaphthylene anion radical In N,N-dimethyl-formamide Yield given. Yields of byproduct given;A n/a
B n/a
C 7%
naphth-1-yl acetic acid
86-87-3

naphth-1-yl acetic acid

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With PPA
Multi-step reaction with 2 steps
1: SOCl2
2: AlCl3 / CS2
View Scheme
Stage #1: naphth-1-yl acetic acid With thionyl chloride; pyridine In dichloromethane at 20℃; for 3h; Friedal Craft reaction;
Stage #2: With carbon disulfide; aluminum (III) chloride
2-acetylacenaphthenone
71739-32-7

2-acetylacenaphthenone

diethyl ether
60-29-7

diethyl ether

phenylmagnesium bromide

phenylmagnesium bromide

A

acetophenone
98-86-2

acetophenone

B

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

acenaphthenequinone monoxime
33489-49-5

acenaphthenequinone monoxime

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With hydrogenchloride; iron; acetic acid
1,2-dibromoacenaphthene
14209-08-6

1,2-dibromoacenaphthene

A

1,1'-biacenaphthylenyliden-2-one
477-77-0

1,1'-biacenaphthylenyliden-2-one

B

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With hydrogenchloride; ethanol
1-acenaphthenol
6306-07-6

1-acenaphthenol

chromium(lll) acetate
1066-30-4

chromium(lll) acetate

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

2,2-Dichlor-1(2H)-acenaphthenon
13152-85-7

2,2-Dichlor-1(2H)-acenaphthenon

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With acetic acid; zinc
1,2-dihydroacenaphthylene-1,2-diol
17976-92-0

1,2-dihydroacenaphthylene-1,2-diol

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With sodium ethanolate; methyl iodide
With hydrogenchloride
2-phenylimino-acenaphthen-1-one
83165-56-4

2-phenylimino-acenaphthen-1-one

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With hydrogenchloride; iron; acetic acid
acenaphthene
83-32-9

acenaphthene

acetone
67-64-1

acetone

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
Einwirkung von Sonnenlicht;
naphthalen-1-yl-acetyl chloride
5121-00-6

naphthalen-1-yl-acetyl chloride

chlorobenzene
108-90-7

chlorobenzene

A

1-(4-chloro-phenyl)-2-[1]naphthyl-ethanone

1-(4-chloro-phenyl)-2-[1]naphthyl-ethanone

B

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With aluminium trichloride
allyldioxazaborolidine
115345-15-8

allyldioxazaborolidine

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

C15H14O
1254364-00-5

C15H14O

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃;99%
1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

(S)-(+)-1,2-dihydroacenaphthylen-1-ol
121961-98-6

(S)-(+)-1,2-dihydroacenaphthylen-1-ol

Conditions
ConditionsYield
With formic acid; C29H38N3O2RuS; triethylamine In ethyl acetate at 40℃; for 24h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;96%
With (+)-β-chlorodiisopinocampheylborane In tetrahydrofuran at -25℃; for 11h; under argon atmosphere;
With borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; dichloromethane; toluene at -30℃;
3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

2-(m-chlorobenzylidene)-1-acenaphthenone

2-(m-chlorobenzylidene)-1-acenaphthenone

Conditions
ConditionsYield
With hydrogenchloride In acetic acid for 3h;95%
1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

acenaphthene quinone
82-86-0

acenaphthene quinone

Conditions
ConditionsYield
With N-Bromosuccinimide; dimethyl sulfoxide Ambient temperature;95%
With N-Bromosuccinimide In dimethyl sulfoxide for 24h; Product distribution; Ambient temperature; further halogenating agents; variation of concentration, temperature and time;95%
Multi-step reaction with 2 steps
1: ethanol; aqueous NaOH-solution
2: diluted aqueous sulfuric acid
View Scheme
1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

(R)-1,2-dihydroacenaphthylen-1-ol
6306-07-6, 92720-77-9, 121961-98-6, 121961-97-5

(R)-1,2-dihydroacenaphthylen-1-ol

Conditions
ConditionsYield
With formic acid; C38H40ClN2O3RhS; triethylamine In neat (no solvent) at 24 - 30℃; for 5.5h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;95%
With (-)-diisopinocamphenylborane chloride In tetrahydrofuran at -25℃; for 11h; under argon atmosphere;
1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

1-acenaphthenol
6306-07-6

1-acenaphthenol

Conditions
ConditionsYield
With hydrogen In methanol at 100℃; under 30003 Torr; Temperature; Autoclave;94.2%
With sodium tetrahydroborate In methanol at 20℃; for 2h;87%
With hydrogen; nickel at 230℃;
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

2-bromoacenaphthylene-1-carbaldehyde
663599-33-5

2-bromoacenaphthylene-1-carbaldehyde

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With phosphorus tribromide In chloroform at 0 - 20℃; for 0.583333h;
Stage #2: 1(2H)-acenaphthylenone In chloroform at 20℃; for 12h;
94%
With phosphorus tribromide
Stage #1: N,N-dimethyl-formamide With phosphorus tribromide In chloroform at 20℃; Cooling with ice;
Stage #2: 1(2H)-acenaphthylenone In chloroform at 20℃; for 8.16667h;
With phosphorus tribromide In chloroform at 20℃; for 12h;
Stage #1: N,N-dimethyl-formamide With phosphorus(V) oxybromide In chloroform at 0 - 20℃; for 1.5h; Inert atmosphere;
Stage #2: 1(2H)-acenaphthylenone In chloroform at 20℃; for 16h;
6.0 g
1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

2-bromoacenaphthylen-1(2H)-one
16269-27-5

2-bromoacenaphthylen-1(2H)-one

Conditions
ConditionsYield
With copper(ll) bromide In ethyl acetate Reflux;91%
With N-Bromosuccinimide; dichloromethane59%
With carbon disulfide; bromine
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

o-chlorobenzylidine acenaphthenone

o-chlorobenzylidine acenaphthenone

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 1h; Ambient temperature;91%
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

2-(m-bromobenzylidene)-1-acenaphthenone

2-(m-bromobenzylidene)-1-acenaphthenone

Conditions
ConditionsYield
With hydrogenchloride In acetic acid for 3h;91%
ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

2-trifluoroacetyl-1-acenaphthenone

2-trifluoroacetyl-1-acenaphthenone

Conditions
ConditionsYield
Stage #1: ethyl trifluoroacetate, With sodium hydride In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: 1(2H)-acenaphthylenone In tetrahydrofuran for 2h; Reflux;
89%
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

methyl 2-oxo-1,2-dihydroacenaphthylene-1-carboxylate

methyl 2-oxo-1,2-dihydroacenaphthylene-1-carboxylate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 65℃; for 3h; Inert atmosphere;89%
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

O-chlorobenzylidineacenaphthenone
122733-68-0

O-chlorobenzylidineacenaphthenone

Conditions
ConditionsYield
With alkaline hydroxide In ethanol at 0℃;87.7%
benzaldehyde
100-52-7

benzaldehyde

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

benzylidine acenaphthenone
70312-09-3

benzylidine acenaphthenone

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 1h; Ambient temperature;87%
6-(naphthalen-1-yl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile
454703-35-6

6-(naphthalen-1-yl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

10-(naphthalen-1-yl)-8-(piperidin-1-yl)fluoranthene-7-carbonitrile
1225222-95-6

10-(naphthalen-1-yl)-8-(piperidin-1-yl)fluoranthene-7-carbonitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.216667h;85%
1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

6-(4-methoxyphenyl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile
757235-52-2

6-(4-methoxyphenyl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile

10-(4-methoxyphenyl)-8-(piperidin-1-yl)fluoranthene-7-carbonitrile
1537881-59-6

10-(4-methoxyphenyl)-8-(piperidin-1-yl)fluoranthene-7-carbonitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.2h;84%
1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

6-(4-methoxyphenyl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile
757235-52-2

6-(4-methoxyphenyl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile

10-(4-methoxyphenyl)-8-(pyrrolidin-1-yl)fluoranthene-7-carbonitrile

10-(4-methoxyphenyl)-8-(pyrrolidin-1-yl)fluoranthene-7-carbonitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 25℃; for 0.25h;84%
trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

4,4-dimethyl-1-phenyl-1-penten-3-one
538-44-3

4,4-dimethyl-1-phenyl-1-penten-3-one

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

4-phenyl-2-t-butyl-1-oxoniafluoranthene trifluoromethanesulphonate
85973-31-5

4-phenyl-2-t-butyl-1-oxoniafluoranthene trifluoromethanesulphonate

Conditions
ConditionsYield
at 100℃; for 5h;83%
1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

1,2,2a,3,4,5-hexahydro-acenaphthylene
480-72-8

1,2,2a,3,4,5-hexahydro-acenaphthylene

Conditions
ConditionsYield
With triethylsilane; 2C2H3F3O*BF3 In dichloromethane at 20℃; for 4h;82%
With nickel; decalin at 230℃; Hydrogenation;
ethane-1,2-dithiol
540-63-6

ethane-1,2-dithiol

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane82%
With toluene-4-sulfonic acid In benzene for 12h; Heating;
2-oxo-4-(piperidin-1-yl)-6-(pyren-1-yl)-2H-pyran-3-carbonitrile
1122565-64-3

2-oxo-4-(piperidin-1-yl)-6-(pyren-1-yl)-2H-pyran-3-carbonitrile

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

8-(piperidin-1-yl)-10-(pyren-1-yl)fluoranthene-7-carbonitrile
1225222-96-7

8-(piperidin-1-yl)-10-(pyren-1-yl)fluoranthene-7-carbonitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.25h;82%
6-(1-naphthyl)-2-oxo-4-pyrrolidin-1-yl-2H-pyran-3-carbonitrile
454703-34-5

6-(1-naphthyl)-2-oxo-4-pyrrolidin-1-yl-2H-pyran-3-carbonitrile

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

10-(naphthalen-1-yl)-8-(pyrrolidin-1-yl)fluoranthene-7-carbonitrile
1225222-94-5

10-(naphthalen-1-yl)-8-(pyrrolidin-1-yl)fluoranthene-7-carbonitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.2h;82%
1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

2-oxo-4-(piperidin-1-yl)-6-(thiophen-2-yl)-2H-pyran-3-carbonitrile
757235-61-3

2-oxo-4-(piperidin-1-yl)-6-(thiophen-2-yl)-2H-pyran-3-carbonitrile

10-phenyl-8-(pyrrolidin-1-yl)fluoranthene-7-carbonitrile
1537881-57-4

10-phenyl-8-(pyrrolidin-1-yl)fluoranthene-7-carbonitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.2h;82%
2-oxo-6-phenyl-4-(pyrrolidin-1-yl)-2H-pyran-3-carbonitrile
454703-31-2

2-oxo-6-phenyl-4-(pyrrolidin-1-yl)-2H-pyran-3-carbonitrile

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

10-phenyl-8-(pyrrolidin-1-yl)fluoranthene-7-carbonitrile
1537881-57-4

10-phenyl-8-(pyrrolidin-1-yl)fluoranthene-7-carbonitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 27℃; for 0.2h;82%
6-(4-nitrophenyl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile

6-(4-nitrophenyl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile

1(2H)-acenaphthylenone
2235-15-6

1(2H)-acenaphthylenone

10-(4-nitrophenyl)-8-(piperidin-1-yl)fluoranthene-7-carbonitrile

10-(4-nitrophenyl)-8-(piperidin-1-yl)fluoranthene-7-carbonitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 25℃; for 0.25h;81%

2235-15-6Relevant articles and documents

Oxidation of alkyl aromatics to ketones by tert-butyl hydroperoxide on manganese dioxide catalyst

Burange, Anand S.,Kale, Sandip R.,Jayaram, Radha V.

, p. 2989 - 2992 (2012)

The catalytic activity of the manganese oxide was investigated for the oxidative functionalization of alkylaromatics to benzylic ketones using tert-butyl hydroperoxide (TBHP) as an oxidant. Manganese oxides of different types were tested for this reaction. Of all the oxides, the nano amorphous manganese dioxide exhibited significant catalytic activity and selectivity for the reaction. The nano amorphous MnO2/TBHP catalytic system could also be reused for six consecutive cycles with no considerable loss in catalytic activity.

The electron as a protecting group. 3. Generation of acenaphthyne radical anion and the determination of the heat of formation of a strained cycloalkyne

Broadus,Kass

, p. 4189 - 4196 (2001)

Acenaphthyne dicarboxylate (12) was transferred into the gas phase from solution via electrospray ionization and subsequently was sequentially fragmented in a Fourier transform mass spectrometer to afford acenaphthyne radical anion (9). Structural confirmation of 9 was achieved by converting it to acenaphthenone enolate (13) and demonstrating that this species is identical to the ion produced upon deprotonation of acenaphthenone (5). The reactivity of 9 was explored, and since an electron can serve as a protecting group, we were able to measure the heat of hydrogenation (98 ± 4 kcal mol-1) and the heat of formation (160 ± 4 kcal mol-l) of acenaphthyne (1) via the application of a thermodynamic cycle. Its strain energy (68 kcal mol-1) and acenaphthylene's (10H) first and second C-H bond dissociation energies (117 ± 4 and 84 ± 2 kcal mol-1) also were obtained. Ab initio and density functional theory calculations were carried out on the species of interest to explore their geometries and energetics. Our results were interpreted in comparison to cyclopentyne, and its predicted heat of formation (98 kcal mol-l) and strain energy (59 kcal mol-1) are reported.

-

Ramirez,F.,Ramanathan,N.

, p. 3041 - 3042 (1961)

-

Conjugated Biradical Intermediates: Spectroscopic, Kinetic, and Trapping Studies of 2,2-Dimethyl-1,3-perinaphthadiyl

Hasler, Erich,Gassmann, Ernst,Wirz, Jacob

, p. 777 - 788 (1985)

The biradical 2,2-dimethyl-1,3-perinaphthadiyl (a) was generated from different precursors, the naphthocyclopropane 1 and the azo copound 2, and from each by three different pathways (pyrolysis, direct photolysis, and triplet sensitization, Scheme 1).The combined evidence from flash photolysis, low-temperature spectroscopy, and product analyses provides a detailed mechanistic picture of the formation and decay of this reactive intermediate which is persistent at 77 K in the triplet ground state (3a) and rather long-lived (400 μs) at room temperature.When formed in its lowest singlet state (1a), the biradical is too short-lived to undergo intersystem crossing to 3a or bimolecular reactions.Thus, 3a is formed exclusively from the excited triplet state of the precursor compounds, 31* or 32*.The monomolecular decay of 3a is retarded by the spin barrier; 3a initiates the polymerization of acrylonitrile and is trapped by 3O2.

Polyethylene glycol radical-initiated benzylic C-H bond oxygenation in compressed carbon dioxide

Wang, Jin-Quan,He, Liang-Nian

, p. 1637 - 1640 (2009)

The PEG radical originating from the thermal/oxidative degradation of PEG in dense CO2 was successfully applied to the oxygenation of benzylic hydrocarbons under organic solvent-free conditions. In addition, in our study, dense CO2 could improve the oxygenation reaction.

High-efficient metal-free aerobic oxidation of aromatic hydrocarbons by N, N-dihydroxypyromellitimide and 1,4-diamino-2,3-dichloroanthraquinone

Chen, Chen,Lv, Zhenguo,Wang, Huibin,Yang, Yuanyuan,Ye, Yicheng,Zhang, Qiaohong,Zhu, Zhuwei

, (2021/12/30)

Metal-free organic catalytic system combining with N, N-dihydroxypyromellitimide (NDHPI) and 1,4-diamino-2,3-dichloroanthraquinone (DADCAQ) was developed for the selective oxidation of hydrocarbon. Being able to simultaneously show good catalytic activity for the oxidation of hydrocarbon and alcohol, NDHPI/DADCAQ was found to be efficient for the conversion of hydrocarbon to ketone. In addition, due to its specific molecular structure, NDHPI was found to be more stable and could supply a PIDNO (pyromellitimide N, N-dioxyl free radical) during the catalytic process. So, higher catalytic activity could be obtained than the famous NHPI even with only half usage, which resolved the problem of high usage (usually 10 mol%) for the organic N-OH compounds to some extent. With 5 mol% NDHPI and 1.25 mol% DADCAQ being used under the conditions of 110 °C and 0.3 MPa molecular oxygen for 7 h, high conversion of ethylbenzene (89.6%), tetralin (98.8%), indene (96.9%), and inert toluene (50.7%) could be selectively converted to the products of acetophenone (93.4%), α-tetralone (97.3%), 1-indanone (98.9%), and benzoic acid (92.4%), respectively.

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

Li, Zhibin,Zhang, Yan,Li, Kuiliang,Zhou, Zhenghong,Zha, Zhenggen,Wang, Zhiyong

, p. 2134 - 2141 (2021/09/29)

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]

Ruthenium-Catalyzed Dehydrogenation of Alcohols with Carbodiimide via a Hydrogen Transfer Mechanism

Sueki, Shunsuke,Matsuyama, Mizuki,Watanabe, Azumi,Kanemaki, Arata,Katakawa, Kazuaki,Anada, Masahiro

, p. 4878 - 4885 (2020/06/02)

Ruthenium-catalyzed oxidative dehydrogenation of alcohols using carbodiimide as an efficient hydrogen acceptor has been developed. The protocol exhibits wide substrate scope with good to excellent yields. The results of the kinetic analysis indicated that the reaction mechanism includes the hydrogen transfer process and that the addition of carbodiimide is essential for the reaction system, and the resulting amidine also could react as a hydrogen acceptor.

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