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642-31-9

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642-31-9 Usage

Chemical Properties

yellow powder

Uses

9-Anthraldehyde is used to prepare asymmetrical tridentate Schiff base ligands, 2-(9-anthrylmethyl-ideneamino)-4-methyl-phenol and functionalized ligand like 2-(anthracen-9-ylidene)-4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione through Knoevenangel condensation with the diphosphine ligand 4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione. It is also used as an intermediate for dyes, pigment, active pharmaceutical ingredients and other organic compounds. Further, it is involved in the Diels Alder reaction with benzenediazonium-2-carboxylate.

General Description

The Diels-Alder reaction of 9-anthracenecarboxaldehyde with benzenediazonium-2-carboxylate was studied.

Purification Methods

9-Anthraldehyde [642-31-9] M 206.2, m 104-105o. Crystallise the aldehyde from acetic acid or EtOH. [Masnori et al. J Am Chem Soc 108 1126 1986, Beilstein 7 IV 1738.]

Check Digit Verification of cas no

The CAS Registry Mumber 642-31-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,4 and 2 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 642-31:
(5*6)+(4*4)+(3*2)+(2*3)+(1*1)=59
59 % 10 = 9
So 642-31-9 is a valid CAS Registry Number.
InChI:InChI=1/C15H10O/c16-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)15/h1-10H

642-31-9 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (A11258)  9-Anthraldehyde, 98%   

  • 642-31-9

  • 25g

  • 499.0CNY

  • Detail
  • Alfa Aesar

  • (A11258)  9-Anthraldehyde, 98%   

  • 642-31-9

  • 100g

  • 1652.0CNY

  • Detail
  • Alfa Aesar

  • (A11258)  9-Anthraldehyde, 98%   

  • 642-31-9

  • 500g

  • 7807.0CNY

  • Detail
  • Aldrich

  • (278688)  9-Anthracenecarboxaldehyde  97%

  • 642-31-9

  • 278688-5G

  • 241.02CNY

  • Detail
  • Aldrich

  • (278688)  9-Anthracenecarboxaldehyde  97%

  • 642-31-9

  • 278688-25G

  • 638.82CNY

  • Detail
  • Aldrich

  • (278688)  9-Anthracenecarboxaldehyde  97%

  • 642-31-9

  • 278688-100G

  • 1,956.24CNY

  • Detail

642-31-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 9-Anthraldehyde

1.2 Other means of identification

Product number -
Other names anthracene-9-carbaldehyde

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:642-31-9 SDS

642-31-9Synthetic route

9-hydroxymethylanthracene
1468-95-7

9-hydroxymethylanthracene

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With potassium carbonate; chlorobenzene In toluene at 105℃; for 24h;100%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In N,N-dimethyl-formamide at 23 - 25℃; for 7.5h;100%
With polymeric complex of oxodiperoxochromium(VI) compound and pyrazine (Pyz-CrO5)n In dichloromethane for 0.6h; Ambient temperature;99%
anthracene
120-12-7

anthracene

trifluoromethanesulphonyloxy-methylene-N,N-dimethyliminium trifluoromethanesulphonate
132407-64-8

trifluoromethanesulphonyloxy-methylene-N,N-dimethyliminium trifluoromethanesulphonate

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
In dichloromethane at 37℃; for 48h;98%
9-anthracenealdehyde oxime
18004-57-4

9-anthracenealdehyde oxime

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With cethyltrimethylammonium permanganate In dichloromethane at 25℃; for 0.25h;96%
With polymeric complex of oxodiperoxochromium(VI) compound and pyrazine (Pyz-CrO5)n In dichloromethane for 0.9h; Ambient temperature;90%
Dichloromethyl methyl ether
4885-02-3

Dichloromethyl methyl ether

anthracene
120-12-7

anthracene

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at 0 - 20℃;95%
3-(anthracene-9-yl)acrylaldehyde
38982-12-6

3-(anthracene-9-yl)acrylaldehyde

A

acetaldehyde
75-07-0

acetaldehyde

B

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydroxide; water at 150℃; for 0.166667h; Reagent/catalyst; Microwave irradiation; Green chemistry;A n/a
B 93%
anthracene
120-12-7

anthracene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With silica gel; trichlorophosphate for 0.025h; Formylation; Microwave irradiation (300 W);92%
With trichlorophosphate In chlorobenzene for 2h; Schlenk technique; Inert atmosphere; Reflux;85%
With trichlorophosphate In 1,2-dichloro-ethane at 40℃; for 1h; Vilsmeier Haack formylation; ultrasound irradiation;80%
9-vinylanthracene
2444-68-0

9-vinylanthracene

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With sodium periodate In water; ethyl acetate; acetonitrile at 0℃; for 3h;92%
With aluminum oxide; potassium permanganate In dichloromethane at 20℃; for 48h;30%
With isobutyraldehyde In acetonitrile at 80℃; for 24h;
potassium cyanide
151-50-8

potassium cyanide

9-cyano-10-anthracenocarboxaldehyde
93496-78-7

9-cyano-10-anthracenocarboxaldehyde

A

9-cyanoanthracene
1210-12-4

9-cyanoanthracene

B

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
In ethanol; water at 80℃; for 31h;A 91%
B 9.4%
9-(dipropionyloxymethyl)anthracene
848030-49-9

9-(dipropionyloxymethyl)anthracene

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In methanol at 20℃; for 9h;91%
C18H16S2
130614-22-1

C18H16S2

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With eosin y In water; acetonitrile at 20℃; for 2h; Irradiation;91%
9-methylanthracene
779-02-2

9-methylanthracene

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; acetic acid for 0.5h; Heating;90%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; acetic acid for 0.5h; Product distribution; Heating; other alkyl- and cycloalkylene-aromatic hydrocarbons;90%
With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In water Reflux;87%
With nickel-doped graphene carbon nitride nanoparticles; air In ethanol at 25℃; for 8h; Irradiation; Green chemistry;85%
anthracene
120-12-7

anthracene

N-methyl-N-phenylformamide
93-61-8

N-methyl-N-phenylformamide

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With trichlorophosphate In 1,2-dichloro-benzene at 89.84 - 94.84℃; for 2h; Vielsmeyer reaction;89%
With trichlorophosphate In 1,2-dichloro-benzene at 0 - 90℃;84%
With trichlorophosphate In 1,2-dichloro-benzene at 100℃; for 1h;81%
9-(azidomethyl)anthracene
195133-98-3

9-(azidomethyl)anthracene

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With MoO2(S2CNEt2)2; oxygen In water for 10h; Heating;88%
Stage #1: 9-(azidomethyl)anthracene With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 4h; Inert atmosphere;
Stage #2: With water In dimethyl sulfoxide; mineral oil for 0.25h; Inert atmosphere;
72%
(9-anthrylmethyl)dimethylsulfonium hydrogensulfate

(9-anthrylmethyl)dimethylsulfonium hydrogensulfate

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With ethanol In dimethyl sulfoxide at 30℃; sonic bath;86%
α,α-diacetoxy-9-methylanthracene
111354-83-7

α,α-diacetoxy-9-methylanthracene

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In methanol at 20℃; for 12h;85%
With carbon tetrabromide In acetonitrile for 8h; Heating;75%
With indium(III) chloride In water at 20℃;
9-anthracenecarboxaldehyde dimethyl acetal
98178-26-8

9-anthracenecarboxaldehyde dimethyl acetal

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
perchloric acid In methanol; water at 25 - 30℃; for 0.5h;82%
With water In methanol at 25 - 30℃; for 0.5h;82%
With iron(III) In dimethylsulfoxide-d6
9-anthrylacetic acid
6624-23-3

9-anthrylacetic acid

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With potassium carbonate In chloroform at 20℃; for 24h; Irradiation; Inert atmosphere;82%
corresponding thioacetal

corresponding thioacetal

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With dibenzoyl peroxide80%
bromo-9 methoxymetyl-10 anthracene
86170-60-7

bromo-9 methoxymetyl-10 anthracene

A

9-(methoxymethyl)anthracene
2584-79-4

9-(methoxymethyl)anthracene

B

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

C

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With potassium phenolate In N,N,N,N,N,N-hexamethylphosphoric triamide at 100℃; for 4h;A 4%
B 5%
C 77%
(anthracen-9-yl)methyl methyl sulfide
61574-53-6

(anthracen-9-yl)methyl methyl sulfide

1,4-diphenyl-but-2-yne-1,4-dione
1087-09-8

1,4-diphenyl-but-2-yne-1,4-dione

A

1,2,4,5-tetrabenzoylbenzene
3867-56-9

1,2,4,5-tetrabenzoylbenzene

B

C32H24O2S

C32H24O2S

C

hexabenzoylbenzene

hexabenzoylbenzene

D

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 15h; Diels-Alder Cycloaddition; Reflux;A 1%
B 76%
C 1%
D 10%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

9-Bromoanthracene
1564-64-3

9-Bromoanthracene

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
Stage #1: tert-butylisonitrile; 9-Bromoanthracene With triethylsilane; palladium diacetate; sodium carbonate; CyJohnPhos In N,N-dimethyl-formamide at 65℃; for 8h; Inert atmosphere; Sealed tube; Green chemistry;
Stage #2: With water Green chemistry;
67%
9-hydroxymethylanthracene
1468-95-7

9-hydroxymethylanthracene

A

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

B

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With osmium(VIII) oxide; trimethylamine-N-oxide In tetrahydrofuran; pyridine; water at 65℃;A 64%
B n/a
(anthracen-9-yl)methyl methyl sulfide
61574-53-6

(anthracen-9-yl)methyl methyl sulfide

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

A

(anthracen-9-yl)methyl acetate
16430-32-3

(anthracen-9-yl)methyl acetate

B

C23H20O6

C23H20O6

C

C22H20O4S

C22H20O4S

D

1,2-bis(methoxycarbonyl)-1-methylthioethylene
87281-45-6

1,2-bis(methoxycarbonyl)-1-methylthioethylene

E

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With acetic acid for 3h; Diels-Alder Cycloaddition; Reflux;A 63%
B 1%
C 1%
D 18%
E 6%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With manganese(IV) oxide In chloroform at 60℃; for 4h;60%
2-(3-indole)-ethanol
526-55-6

2-(3-indole)-ethanol

9-anthracenecarboxaldehyde dimethyl acetal
98178-26-8

9-anthracenecarboxaldehyde dimethyl acetal

A

1-(anthracen-9-yl)-1,3,4,9-tetrahydropyrano[3,4-b]indole

1-(anthracen-9-yl)-1,3,4,9-tetrahydropyrano[3,4-b]indole

B

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With camphor-10-sulfonic acid In chloroform for 16h; Reagent/catalyst; Solvent; Pictet-Spengler Synthesis; Schlenk technique; Inert atmosphere;A 60%
B 13 %Spectr.
tris(dichloromethyl)amine
25891-29-6

tris(dichloromethyl)amine

anthracene
120-12-7

anthracene

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With titanium tetrachloride In chlorobenzene at 0 - 20℃; for 12h;48%
<9,10-dihydro-10-(methoxymethylene)-9-trimethylsilyl>antracene
88920-44-9

<9,10-dihydro-10-(methoxymethylene)-9-trimethylsilyl>antracene

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With silica gel In hexane for 20h;47%
(anthracen-9-yl)methyl methyl sulfide
61574-53-6

(anthracen-9-yl)methyl methyl sulfide

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

A

dimethyl (dimethyl-oxo-1H-benzo[de]anthracene-2,3-dicarboxylate)

dimethyl (dimethyl-oxo-1H-benzo[de]anthracene-2,3-dicarboxylate)

B

C22H20O4S

C22H20O4S

C

C36H38O24

C36H38O24

D

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene for 10h; Solvent; Diels-Alder Cycloaddition; Reflux;A 10%
B 44%
C 1%
D 9%
(anthracen-9-yl)methyl methyl sulfide
61574-53-6

(anthracen-9-yl)methyl methyl sulfide

1,4-diphenyl-but-2-yne-1,4-dione
1087-09-8

1,4-diphenyl-but-2-yne-1,4-dione

A

(anthracen-9-yl)methyl acetate
16430-32-3

(anthracen-9-yl)methyl acetate

B

1,2,4,5-tetrabenzoylbenzene
3867-56-9

1,2,4,5-tetrabenzoylbenzene

C

C32H24O2S

C32H24O2S

D

hexabenzoylbenzene

hexabenzoylbenzene

E

5,6,-11,12-tetrahydro-4b,12[1',2']:6,10b[1'',2'']dibenzenochrysene
55614-27-2

5,6,-11,12-tetrahydro-4b,12[1',2']:6,10b[1'',2'']dibenzenochrysene

F

2-(methylthio)-1,4-diphenylbut-2-ene-1,4-dione
63113-55-3, 63113-56-4

2-(methylthio)-1,4-diphenylbut-2-ene-1,4-dione

G

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With acetic acid for 13h; Diels-Alder Cycloaddition; Reflux;A 14%
B 1%
C 42%
D 2%
E 6%
F 10%
G 19%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

9-(methoxymethyl)anthracene carbanion
135598-25-3

9-(methoxymethyl)anthracene carbanion

A

9-neopentylantracene
63383-01-7

9-neopentylantracene

B

<9,10-dihydro-10-(methoxymethylene)-9-trimethylsilyl>antracene
88920-44-9

<9,10-dihydro-10-(methoxymethylene)-9-trimethylsilyl>antracene

C

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
A 36%
B 40%
C 16%
A 36%
B 40%
C n/a
9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

9-Anthracenecarboxylic acid
723-62-6

9-Anthracenecarboxylic acid

Conditions
ConditionsYield
With cobalt(II) 2,9,16,23-phthalocyanine tetrasulfonic acid In water; acetonitrile at 20℃; under 760.051 Torr; for 150h; UV-irradiation;100%
With (bipyH2)-CrOCl5 In dichloromethane at 28 - 30℃; for 12h;95%
With dihydrogen peroxide In water; acetonitrile at 45℃; for 1h; chemoselective reaction;78%
2,4,5,7-tetranitro-9H-fluorene
29210-71-7

2,4,5,7-tetranitro-9H-fluorene

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

9-(9-anthrylmethylene)-2,4,5,7-tetranitrofluorene

9-(9-anthrylmethylene)-2,4,5,7-tetranitrofluorene

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;100%
9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

crosslinked polystyrene-supported phosphonium salt of 2-bromomethylnaphthalene

crosslinked polystyrene-supported phosphonium salt of 2-bromomethylnaphthalene

1-<2>Naphthyl-2-<9>anthryl-aethylen
1654-47-3

1-<2>Naphthyl-2-<9>anthryl-aethylen

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane for 2h; Ambient temperature;100%
ethylamine
75-04-7

ethylamine

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

[1-Anthracen-9-yl-meth-(Z)-ylidene]-ethyl-amine

[1-Anthracen-9-yl-meth-(Z)-ylidene]-ethyl-amine

Conditions
ConditionsYield
at 20℃; under 750.06 Torr; Solid phase reaction; gas-solid reaction;100%
In methanol for 9h; Reflux;84%
9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

methylamine
74-89-5

methylamine

N-(9-anthrylmethylidene)methylamine
73356-20-4

N-(9-anthrylmethylidene)methylamine

Conditions
ConditionsYield
at 20℃; under 750.06 Torr; Solid phase reaction; gas-solid reaction;100%
In tetrahydrofuran; methanol
In ethanol
Trimethylenediamine
109-76-2

Trimethylenediamine

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

N-((anthracen-10-Yl)methylene)-N′-((anthracen-9-Yl)methylene)propane-1,3-diamine

N-((anthracen-10-Yl)methylene)-N′-((anthracen-9-Yl)methylene)propane-1,3-diamine

Conditions
ConditionsYield
With acetic acid In ethanol Heating;100%
In methanol; N,N-dimethyl-formamide for 4h; Heating;94%
With acetic acid In methanol for 12h; Reflux;85.32%
1,4-diaminobutane
110-60-1

1,4-diaminobutane

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

1,2-bis[(anthracen-9-ylmethylene)amino]butane-1,4-diamine

1,2-bis[(anthracen-9-ylmethylene)amino]butane-1,4-diamine

Conditions
ConditionsYield
With acetic acid In ethanol Heating;100%
In methanol; dichloromethane for 4h; Heating;
In methanol; dichloromethane for 4h; Reflux;
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

N1-(anthracene-9-methylene)benzene-1,2-diamine
94963-64-1

N1-(anthracene-9-methylene)benzene-1,2-diamine

Conditions
ConditionsYield
With acetic acid In toluene for 2h; Reflux;100%
With acetic acid In toluene for 2h; Reflux;94%
In ethanol at 20℃; for 6h;88%
In methanol at -5℃; for 6h;70%
(4-(but-3-en-1-yloxy)phenyl)methanamine
865539-68-0

(4-(but-3-en-1-yloxy)phenyl)methanamine

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

AnCH=NC6H4OCH2CH2CH=CH2
1202814-43-4

AnCH=NC6H4OCH2CH2CH=CH2

Conditions
ConditionsYield
In toluene Molecular sieve; Reflux;100%
(5S)-5-benzylpyrrolidine-2,4-dione
69358-30-1

(5S)-5-benzylpyrrolidine-2,4-dione

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

C26H19NO2

C26H19NO2

Conditions
ConditionsYield
With L-proline In ethanol at 20℃;100%
3,6-dioxa-1,8-diaminooctane
929-59-9

3,6-dioxa-1,8-diaminooctane

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

C36H32N2O2

C36H32N2O2

Conditions
ConditionsYield
With acetic acid In toluene for 2h; Reflux;100%
9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

9-hydroxymethylanthracene
1468-95-7

9-hydroxymethylanthracene

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 20℃; for 0.5h;99%
With sodium tetrahydroborate In ethanol at 20℃; for 0.5h;99%
With sodium tetrahydroborate In tetrahydrofuran for 2h; Reflux;99%
nitromethane
75-52-5

nitromethane

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

(E)‐9‐(2‐nitrovinyl)anthracene
55446-60-1

(E)‐9‐(2‐nitrovinyl)anthracene

Conditions
ConditionsYield
With cyclohexylamine at 120℃; Microwave irradiation;99%
With piperdinium acetate at 90℃; for 2.5h; Knoevenagel Condensation; Inert atmosphere;99%
With ammonium acetate; acetic acid for 6h; Reflux;52%
9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

benzylamine
100-46-9

benzylamine

1-(anthracen-9-yl)-N-benzylmethanimine
14607-11-5

1-(anthracen-9-yl)-N-benzylmethanimine

Conditions
ConditionsYield
With magnesium sulfate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;99%
With magnesium sulfate; triethylamine In dichloromethane for 120h; Ambient temperature;52%
In toluene for 24h; Schiff Reaction; Reflux; Dean-Stark;26%
(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

(S)-9-(anthracen-9-ylmethylene)-α-phenylethylamine
820975-26-6

(S)-9-(anthracen-9-ylmethylene)-α-phenylethylamine

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 20℃; for 12h;99%
In tetrahydrofuran; ethanol Heating;
With acetic acid In toluene for 6h; Reflux;
(S)-(+)-2-(N-methylamino)-3-phenylpropanol
84773-29-5

(S)-(+)-2-(N-methylamino)-3-phenylpropanol

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

(2S,4S)-2-(9-anthracenyl)-3-methyl-4-benzyl oxazolidine
917599-26-9

(2S,4S)-2-(9-anthracenyl)-3-methyl-4-benzyl oxazolidine

Conditions
ConditionsYield
With magnesium sulfate In tetrahydrofuran at 20℃; for 6h;99%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

C19H19NOSi
118736-05-3

C19H19NOSi

Conditions
ConditionsYield
at 20℃; for 0.5h; Glovebox;99%
With C32H39Br2MgN2(1-)*C16H32LiO4(1+) In chloroform-d1 at 20℃; for 3h; Inert atmosphere; Glovebox;99%
With Zr(IV) metal-organic framework with 1,4-benzenedicarboxylate in anhydrous form In dichloromethane at 40℃; for 46h; Inert atmosphere; Reflux;50%
9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

benzyl alcohol
100-51-6

benzyl alcohol

allyl-trimethyl-silane
762-72-1

allyl-trimethyl-silane

10-(1-(benzyloxy)but-3-enyl)anthracene
1313615-64-3

10-(1-(benzyloxy)but-3-enyl)anthracene

Conditions
ConditionsYield
With perchloric acid supported on silica gel In dichloromethane; acetonitrile at 20℃; for 0.5h; Hosomi-Sakurai reaction;99%
With 50 wt% silicomolybdic acid/SiO2 In acetonitrile at 20℃; for 1h; Hosomi-Sakurai reaction;82%
9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-(anthracene-9-ylmethoxy)pinacolborane
1373393-13-5

2-(anthracene-9-ylmethoxy)pinacolborane

Conditions
ConditionsYield
With C27H44AlN3 In benzene at 20℃; for 0.333333h; Inert atmosphere; Glovebox;99%
With catalyst:C4H9Mg(2,6-iPr2C6H3NCCH3)CH In benzene-d6 pinacolborane reacted with aldehyde in C6D6 at 25°C catalized by nBuMg(2,6-iPrC6H3NCCH3)2CH 0.1-0.5 mol% for 0.75 h;84%
With [HC{(Me)CN(2,6-iPr2C6H3)}2MgnBu] In benzene-d6 at 20℃; for 0.75h; Inert atmosphere; Sealed tube;96 %Spectr.
(1-bromovinyl)triisopropylsilane
1352211-40-5

(1-bromovinyl)triisopropylsilane

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

C26H34OSi
1414296-37-9

C26H34OSi

Conditions
ConditionsYield
Stage #1: (1-bromovinyl)triisopropylsilane With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: 9-anthracene aldehyde In tetrahydrofuran at -78℃; for 1h;
99%
9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

phenylboronic acid
98-80-6

phenylboronic acid

1-(9-anthracyl)-(1-phenyl)methanol

1-(9-anthracyl)-(1-phenyl)methanol

Conditions
ConditionsYield
With potassium phosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; C22H19OP In 1,4-dioxane at 70℃; Inert atmosphere; enantioselective reaction;99%
C6H5NHBO2C2(CH3)4
857402-61-0

C6H5NHBO2C2(CH3)4

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

(E)-N-(9-Anthrylmethylene)benzenamine
796-34-9

(E)-N-(9-Anthrylmethylene)benzenamine

Conditions
ConditionsYield
In benzene-d6 at 25℃; for 1h; Inert atmosphere; Schlenk technique;99%
9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

malononitrile
109-77-3

malononitrile

2‐(anthracen‐9‐ylmethylene)malononitrile
55490-87-4

2‐(anthracen‐9‐ylmethylene)malononitrile

Conditions
ConditionsYield
With C88H68Cl4Hg2N4O4P4 In methanol at 60℃; for 4h; Catalytic behavior; Knoevenagel Condensation;98%
With triethylamine In ethanol at 20℃; for 2h;90%
With Zn(1+)*C5H8NO2(1-) In water at 80℃; for 0.166667h; Knoevenagel Condensation;84%
9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

9-trans-styryl-anthracene
42196-97-4

9-trans-styryl-anthracene

Conditions
ConditionsYield
With crosslinked polymer-supported phosphonium salt of benzyl chloride; cetyltrimethylammonim bromide In sodium hydroxide; dichloromethane for 2h; Product distribution; Ambient temperature; without catalysts; other polymer supported phosphonium salt;98%
Multi-step reaction with 2 steps
1: NaOAc, Ac2O / 145 - 150 °C
2: (i) Cu, quinoline, (ii) I2, xylene
View Scheme
9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

crosslinked polystyrene-supported phosphonium salt of benzyl chloride

crosslinked polystyrene-supported phosphonium salt of benzyl chloride

9-trans-styryl-anthracene
42196-97-4

9-trans-styryl-anthracene

Conditions
ConditionsYield
With sodium hydroxide; cetyltrimethylammonim bromide In dichloromethane for 2h; Ambient temperature;98%
aminomethyl-dimethyl-phosphine oxide
97578-19-3

aminomethyl-dimethyl-phosphine oxide

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

(9-anthracenylmethylene-iminomethyl)-dimethyl-phosphine oxide

(9-anthracenylmethylene-iminomethyl)-dimethyl-phosphine oxide

Conditions
ConditionsYield
In benzene at 20℃; for 4h;98%
9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

chitosan, intrinsic viscosity 230 ml/g, fraction of N-acetylated units 0.09

chitosan, intrinsic viscosity 230 ml/g, fraction of N-acetylated units 0.09

chitosan, intrinsic viscosity 230 ml/g, fraction of N-acetylated units 0.09, N-(9-anthracenemethyl)-labelled

chitosan, intrinsic viscosity 230 ml/g, fraction of N-acetylated units 0.09, N-(9-anthracenemethyl)-labelled

Conditions
ConditionsYield
Stage #1: 9-anthracene aldehyde; chitosan, intrinsic viscosity 230 ml/g, fraction of N-acetylated units 0.09 In methanol; acetic acid at 20℃; for 24h;
Stage #2: With sodium cyanoborohydride at 20℃; for 12h;
98%
9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

anthracene
120-12-7

anthracene

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In ethyl acetate at 150℃; under 12929 Torr; for 0.833333h; Microwave irradiation; Molecular sieve;98%
With palladium nanoparticles supported on fibrous silica In cyclohexane at 130℃; for 20h; Molecular sieve;98%
With palladium diacetate In cyclohexane at 140℃; for 24h; Molecular sieve; air;97%

642-31-9Relevant articles and documents

Regulating signal enhancement with coordination-coupled deprotonation of a hydrazone switch

Foy, Justin T.,Ray, Debdas,Aprahamian, Ivan

, p. 209 - 213 (2014)

Proton relay plays an important role in many biocatalytic pathways. In order to mimic such processes in the context of molecular switches, we developed coordination-coupled deprotonation (CCD) driven signaling and signal enhancement sequences. This was ac

A new acetal as a fluorescent probe for highly selective detection of Fe3+ and its application in bioimaging

Wang, Min,Zhang, Yong-Ming,Zhao, Qin-Yi,Fu, Zhen-Hai,Zhang, Zhi-Hong

, (2019)

A simple fluorescent probe L for Fe3+ was easily synthesized based on anthracene. Among the various metal ions including Fe2+, this probe exhibited high sensitivity and good selectivity toward Fe3+ with turn-off fluorescence mode in DMSO-HEPES buffer solution (20 mM, pH = 7.0, 1:1 (v/v)). When adequate Fe3+ ion was added into the solution of probe L, its molecular structure transferred from anthraldehyde dimethyl acetal to anthraldehyde, resulting in fluorescence quenching with a low detection limit of 3.08 μM. 1H NMR spectra and TLC analysis further supported this concept. Finally, this probe was successfully applied in bioimaging.

REACTION OF BENZOYL PEROXIDE WITH THIOACETALS

Puzin, Yu. I.,Leplyanin, G. V.,Tolstikov, G. A.

, p. 638 - 639 (1990)

-

Nickel(II)-Catalyzed Selective (E)-Olefination of Methyl Heteroarenes Using Benzyl Alcohols via Acceptorless Dehydrogenative Coupling Reaction

Balamurugan, Gunasekaran,Ramesh, Rengan

, (2021/11/30)

An efficient catalytic protocol for the synthesis of selective (E)-olefins by the newly synthesized nickel complexes via greener acceptorless dehydrogenative coupling methodology is presented. Two nickel(II) N, S chelating complexes were structurally characterized with the aid of spectral and single crystal X-ray diffraction methods. Olefination of 2-methylheteroarenes with benzyl alcohols via acceptorless dehydrogenative coupling is achieved by inexpensive nickel(II) catalysts. The present olefination protocol is simple and furnishes the desired 2-alkenylheteroarenes in 35 h and yields in the range of 40–93 %. The dehydrogenative coupling reaction proceeds via the generation of an aldehyde intermediate and produces water and hydrogen as sole by-products. The wide substrate scope of this catalytic reaction covered the synthesis of drug intermediates.

Catalytic study of the copper-based magnetic nanocatalyst on the aerobic oxidation of alcohols in water

Dehkordi, S. Saeid Saei,Albadi, Jalal,Jafari, Abbas Ali,Samimi, Heshmat Allah

, p. 2527 - 2538 (2021/03/24)

A copper-based magnetic nanocatalyst has been prepared by co-precipitation method and characterized by FESEM, EDS, TEM, XRD, XRF, ICP–OES, FTIR, and BET analysis. This new nanocatalyst displays a good activity toward the aerobic oxidation of a wide range of alcohols in water. Moreover, it is recyclable up to five following runs by simple filtration without any significant loss of its catalytic activity.

Magnetic spent coffee ground as an efficient and green catalyst for aerobic oxidation of alcohols and tandem oxidative Groebke–Blackburn–Bienaymé reaction

Farhid, Hassan,Shaabani, Ahmad

, p. 1199 - 1209 (2020/11/09)

Abstract: In this work, magnetic spent coffee ground as a green, inexpensive, and abundant material was synthesized and characterized by a variety of techniques, including X-ray diffraction pattern, thermal gravimetric analysis, scanning electron microscopy, energy-dispersive spectroscopy, inductively coupled plasma optical emission spectrometry, and Fourier transform infrared spectroscopy. The magnetic spent coffee ground was successfully utilized as a catalyst in aerobic oxidation of primary and secondary benzylic alcohols and tandem oxidative Groebke–Blackburn–Bienaymé reaction. Graphic abstract: [Figure not available: see fulltext.].

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