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1-(9-Ethyl-9H-carbazol-3-yl)ethanone, commonly referred to as Ethylcarbazole ketone, is a chemical compound characterized by the molecular formula C17H15NO. It is a ketone derivative of carbazole, a heterocyclic aromatic organic compound. Ethylcarbazole ketone is recognized for its versatile applications in various fields, including organic synthesis, pharmaceuticals, agrochemicals, and dyes. Its potential in the development of organic electronic materials and optoelectronic devices is also noteworthy. Furthermore, its antioxidant and anti-inflammatory properties suggest its potential as a new drug candidate. Careful handling and adherence to safety guidelines are essential when working with this chemical due to its hazardous nature.

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  • 1484-04-4 Structure
  • Basic information

    1. Product Name: 1-(9-ETHYL-9H-CARBAZOL-3-YL)ETHANONE
    2. Synonyms: 1-(9-ETHYL-9H-CARBAZOL-3-YL)ETHANONE;3-acetyl-9-ethylcarbazole;3-acetyl-N-ethylcarbazole;1-(9-ethyl-3-carbazolyl)ethanone;1-(9-ethylcarbazol-3-yl)ethanone;1-(9-Ethyl-9H-carbazol-3-yl)
    3. CAS NO:1484-04-4
    4. Molecular Formula: C16H15NO
    5. Molecular Weight: 237.3
    6. EINECS: 237-182-8
    7. Product Categories: N/A
    8. Mol File: 1484-04-4.mol
  • Chemical Properties

    1. Melting Point: 115 °C
    2. Boiling Point: 353.5°C at 760 mmHg
    3. Flash Point: 167.6°C
    4. Appearance: /
    5. Density: 1.12g/cm3
    6. Vapor Pressure: 3.58E-05mmHg at 25°C
    7. Refractive Index: 1.609
    8. Storage Temp.: Inert atmosphere,Room Temperature
    9. Solubility: N/A
    10. CAS DataBase Reference: 1-(9-ETHYL-9H-CARBAZOL-3-YL)ETHANONE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 1-(9-ETHYL-9H-CARBAZOL-3-YL)ETHANONE(1484-04-4)
    12. EPA Substance Registry System: 1-(9-ETHYL-9H-CARBAZOL-3-YL)ETHANONE(1484-04-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1484-04-4(Hazardous Substances Data)

1484-04-4 Usage

Uses

Used in Organic Synthesis:
1-(9-Ethyl-9H-carbazol-3-yl)ethanone is used as a reactant in organic synthesis for the production of a variety of chemical compounds. Its unique structure allows for the creation of diverse organic molecules, contributing to the advancement of chemical research and development.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 1-(9-Ethyl-9H-carbazol-3-yl)ethanone serves as an intermediate in the synthesis of various drugs. Its presence in the production process aids in the development of new medications, potentially improving treatment options for a range of health conditions.
Used in Agrochemicals:
1-(9-Ethyl-9H-carbazol-3-yl)ethanone is utilized in the agrochemical sector, where it plays a role in the synthesis of compounds used in agricultural applications. Its contribution to the development of agrochemicals can enhance crop protection and yield.
Used in Dyes:
1-(9-ETHYL-9H-CARBAZOL-3-YL)ETHANONE is also employed in the dye industry, where it contributes to the creation of various dyes used in different applications, including textiles and other industrial processes.
Used in Organic Electronic Materials and Optoelectronic Devices:
1-(9-Ethyl-9H-carbazol-3-yl)ethanone has been studied for its potential in the development of organic electronic materials and optoelectronic devices. Its properties make it a promising candidate for use in the advancement of electronic and optoelectronic technologies.
Used in Drug Development:
Due to its antioxidant and anti-inflammatory properties, 1-(9-Ethyl-9H-carbazol-3-yl)ethanone is considered a potential candidate for the development of new drugs. Its ability to combat oxidative stress and inflammation may lead to innovative therapeutic solutions in medicine.

Check Digit Verification of cas no

The CAS Registry Mumber 1484-04-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,8 and 4 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1484-04:
(6*1)+(5*4)+(4*8)+(3*4)+(2*0)+(1*4)=74
74 % 10 = 4
So 1484-04-4 is a valid CAS Registry Number.
InChI:InChI=1/C16H15NO/c1-3-17-15-7-5-4-6-13(15)14-10-12(11(2)18)8-9-16(14)17/h4-10H,3H2,1-2H3

1484-04-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(9-Ethyl-9H-carbazol-3-yl)ethanone

1.2 Other means of identification

Product number -
Other names 1-(9-ethylcarbazol-3-yl)ethanone

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:1484-04-4 SDS

1484-04-4Synthetic route

N-ethylcarbazole
86-28-2

N-ethylcarbazole

acetyl chloride
75-36-5

acetyl chloride

N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

Conditions
ConditionsYield
With bismuth(III) chloride In dichloromethane at 20℃; Friedel Crafts acylation;81%
With zinc(II) chloride In dichloromethane at 20℃; for 6h; Friedel Crafts acylation;80%
With zinc(II) chloride Friedel-Crafts Acylation;
N-ethylcarbazole
86-28-2

N-ethylcarbazole

acetic anhydride
108-24-7

acetic anhydride

N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

Conditions
ConditionsYield
Stage #1: N-ethylcarbazole; acetic anhydride With boron trifluoride diethyl etherate at 20℃; for 4h;
Stage #2: With hydrogenchloride; water
80.4%
With aluminum (III) chloride In dichloromethane at 0 - 20℃; Friedel-Crafts Acylation;70%
With aluminum (III) chloride In dichloromethane at 20℃; for 4h;70.47%
N-ethylcarbazole
86-28-2

N-ethylcarbazole

Acetyl bromide
506-96-7

Acetyl bromide

N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

Conditions
ConditionsYield
Stage #1: N-ethylcarbazole; Acetyl bromide With tin(IV) chloride In dichloromethane at 20℃; for 24h;
Stage #2: With hydrogenchloride In dichloromethane; water Cooling with ice;
80%
With aluminum (III) chloride In 1,2-dichloro-ethane at 20℃; for 5h;74%
With aluminum (III) chloride In 1,2-dichloro-ethane74%
N-ethylcarbazole
86-28-2

N-ethylcarbazole

C10H12N2O4
137131-39-6

C10H12N2O4

A

N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

B

ethyl 5-(1-cyano-2-ethoxy-2-oxoethylidene)prolinate
1355624-73-5

ethyl 5-(1-cyano-2-ethoxy-2-oxoethylidene)prolinate

C

ethyl 5-[2-amino-1-(ethoxycarbonyl)-2-oxoethylidene]prolinate

ethyl 5-[2-amino-1-(ethoxycarbonyl)-2-oxoethylidene]prolinate

D

ethyl 5-[1-cyano-2-(9-ethyl-9H-carbazol-3-yl)-2-oxoethylidene]prolinate
1355624-71-3

ethyl 5-[1-cyano-2-(9-ethyl-9H-carbazol-3-yl)-2-oxoethylidene]prolinate

Conditions
ConditionsYield
With Eaton′s Reagent at 60℃; for 30h; Inert atmosphere;A 1%
B 20%
C 9%
D 40%
N-ethylcarbazole
86-28-2

N-ethylcarbazole

acetyl chloride
75-36-5

acetyl chloride

A

N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

B

1,1′-(9-ethyl-9H-carbazole-3,6-diyl)diethanone
1483-97-2

1,1′-(9-ethyl-9H-carbazole-3,6-diyl)diethanone

Conditions
ConditionsYield
With carbon disulfide; aluminium trichloride
9H-carbazole
86-74-8

9H-carbazole

acetyl chloride
75-36-5

acetyl chloride

N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

Conditions
ConditionsYield
With aluminium trichloride
N-ethylcarbazole
86-28-2

N-ethylcarbazole

acetic anhydride
108-24-7

acetic anhydride

A

N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

B

1,1′-(9-ethyl-9H-carbazole-3,6-diyl)diethanone
1483-97-2

1,1′-(9-ethyl-9H-carbazole-3,6-diyl)diethanone

Conditions
ConditionsYield
With aluminum (III) chloride Friedel Crafts acylation;
9H-carbazole
86-74-8

9H-carbazole

N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / water; acetone / 12 h / Reflux
2.1: tin(IV) chloride / dichloromethane / 24 h / 20 °C
2.2: Cooling with ice
View Scheme
Multi-step reaction with 2 steps
1.1: potassium hydroxide / N,N-dimethyl-formamide / 0.67 h / 20 °C
1.2: 10 h / 20 °C
2.1: boron trifluoride diethyl etherate / 4 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / 20 °C
2: zinc(II) chloride / dichloromethane / 24 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h
1.2: 2 h / 20 °C
2.1: aluminum (III) chloride / dichloromethane / 0.5 h / 20 °C
2.2: 6 h / 0 - 20 °C
View Scheme
2-amino-5-phenyl-1,3,4-thiadiazole
2002-03-1

2-amino-5-phenyl-1,3,4-thiadiazole

N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

C24H20N4S

C24H20N4S

Conditions
ConditionsYield
With choline chloride; oxalic acid at 70℃;95.1%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

2-amino-5-(4'-bromophenyl)-1,3,4-oxadiazole
33621-62-4

2-amino-5-(4'-bromophenyl)-1,3,4-oxadiazole

C24H19BrN4O

C24H19BrN4O

Conditions
ConditionsYield
With choline chloride; oxalic acid at 70℃;88.2%
With toluene-4-sulfonic acid at 20℃; for 0.25h; Reagent/catalyst; Schiff Reaction;81.6%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

4-(Diethylamino)salicylaldehyde
17754-90-4

4-(Diethylamino)salicylaldehyde

7-diethylamino-2-(9-ethyl-9H-carbazol-3-yl)chromen-1-ium

7-diethylamino-2-(9-ethyl-9H-carbazol-3-yl)chromen-1-ium

Conditions
ConditionsYield
With sulfuric acid at 90℃; for 2h;88%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

5-(4-nitrophenyl)-1,3,4-oxadiazol-2-amine
51891-79-3

5-(4-nitrophenyl)-1,3,4-oxadiazol-2-amine

C24H19N5O3

C24H19N5O3

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃; for 0.25h; Reagent/catalyst; Schiff Reaction;87.5%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

thiosemicarbazide
79-19-6

thiosemicarbazide

C17H18N4S

C17H18N4S

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃; for 0.25h;86.9%
5-methyl-1,3,4-thiadiazol-2-amine
108-33-8

5-methyl-1,3,4-thiadiazol-2-amine

N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

C19H18N4S

C19H18N4S

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃; for 0.25h; Reagent/catalyst;86.7%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

2-(9-ethyl-9H-carbazol-3-yl)-2-oxoacetaldehyde

2-(9-ethyl-9H-carbazol-3-yl)-2-oxoacetaldehyde

Conditions
ConditionsYield
With selenium(IV) oxide In 1,4-dioxane; water at 100℃;86.3%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

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

N,N-dimethyl-formamide

(Z)-3-chloro-3-(9-ethyl-9H-carbazol-3-yl)prop-2-enal
741686-55-5

(Z)-3-chloro-3-(9-ethyl-9H-carbazol-3-yl)prop-2-enal

Conditions
ConditionsYield
With trichlorophosphate at 20℃; for 0.416667h;86%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

hydrazine carboxamide
4426-72-6, 51433-48-8

hydrazine carboxamide

C17H18N4O

C17H18N4O

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃; for 0.266667h;83.2%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

methyl naphthalene-2-carboxylate
2459-25-8

methyl naphthalene-2-carboxylate

(2Z)-1-(9-ethyl-9H-carbazol-2-yl)-3-hydroxy-3-naphthalen-2-yl-prop-2-en-1-one
1219036-86-8

(2Z)-1-(9-ethyl-9H-carbazol-2-yl)-3-hydroxy-3-naphthalen-2-yl-prop-2-en-1-one

Conditions
ConditionsYield
With sodium ethanolate In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;81%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

indole-2,3-dione
91-56-5

indole-2,3-dione

2-(9-ethyl-9H-carbazol-3-yl)quinoline-4-carboxylic acid

2-(9-ethyl-9H-carbazol-3-yl)quinoline-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: indole-2,3-dione With cetyltrimethylammonium hydroxide In water at 20℃; for 0.166667h; Pfitzinger Quinoline Synthesis; Sonication; Green chemistry;
Stage #2: N-ethyl-3-acetylcarbazole In water at 35℃; for 6h; Temperature; Pfitzinger Quinoline Synthesis; Sonication; Green chemistry;
78%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane
5123-13-7

5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane

(+)-(R)-1-(9-ethyl-9H-carbazol-3-yl)-1-phenylethan-1-ol

(+)-(R)-1-(9-ethyl-9H-carbazol-3-yl)-1-phenylethan-1-ol

Conditions
ConditionsYield
With hydrogenchloride; bis(1,5-cyclooctadiene)nickel (0); sodium methylate; C67H68N2 In cyclohexane; water at 50℃; for 24h; Inert atmosphere; enantioselective reaction;78%
2,6-bis(methoxycarbonyl)pyridine
5453-67-8

2,6-bis(methoxycarbonyl)pyridine

N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

methyl 6-(3-(9-ethylcarbazol-3-yl)-oxopropanoyl)-2-pyridinecarboxylate
1219496-90-8

methyl 6-(3-(9-ethylcarbazol-3-yl)-oxopropanoyl)-2-pyridinecarboxylate

Conditions
ConditionsYield
With sodium In toluene at 120℃; for 6h; Claisen condensation;76%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

malononitrile
109-77-3

malononitrile

2-(1-(9-ethyl-9H-carbazole-3-yl)ethylidene)malononitrile

2-(1-(9-ethyl-9H-carbazole-3-yl)ethylidene)malononitrile

Conditions
ConditionsYield
With ammonium acetate; acetic acid In toluene at 100℃; for 2h; Knoevenagel Condensation; Green chemistry;76%
With ammonium acetate; acetic acid at 110℃; Knoevenagel Condensation;
2,6-bis(methoxycarbonyl)pyridine
5453-67-8

2,6-bis(methoxycarbonyl)pyridine

N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

1,1'-(pyridine-2,6-diyl)-bis-3-(9-ethylcarbazol-3-yl)-1,3-propanedione
1219496-91-9

1,1'-(pyridine-2,6-diyl)-bis-3-(9-ethylcarbazol-3-yl)-1,3-propanedione

Conditions
ConditionsYield
With sodium In toluene at 120℃; for 6h; Claisen condensation;74%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

2-aminobenzaldehyde
529-23-7

2-aminobenzaldehyde

9-ethyl-3-(quinolin-2-yl)-9H-carbazole

9-ethyl-3-(quinolin-2-yl)-9H-carbazole

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 4h; Reflux;72%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

9-butyl-9H-carbazole-3-carbaldehyde
67707-09-9

9-butyl-9H-carbazole-3-carbaldehyde

3-(9-butyl-9H-carbazol-3-yl)-1-(9-ethyl-9H-carbazol-3-yl)prop-2-en-1-one

3-(9-butyl-9H-carbazol-3-yl)-1-(9-ethyl-9H-carbazol-3-yl)prop-2-en-1-one

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 24h;72%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

1‐(9‐ethyl‐9H‐carbazol‐3‐yl)‐3‐(4‐nitrophenyl)prop‐2‐en‐1‐one
1447733-62-1

1‐(9‐ethyl‐9H‐carbazol‐3‐yl)‐3‐(4‐nitrophenyl)prop‐2‐en‐1‐one

Conditions
ConditionsYield
With potassium hydroxide In methanol; water at 20℃; for 24h;69.2%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

1,3,5-tris(9-ethyl-9H-carbazol-3-yl)benzene
1395347-13-3

1,3,5-tris(9-ethyl-9H-carbazol-3-yl)benzene

Conditions
ConditionsYield
With thionyl chloride In ethanol at 80℃; for 8h; Reagent/catalyst; Inert atmosphere;68%
With thionyl chloride; ethanol for 8h; Reflux;42%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

ethyl thieno[3,2,-b]thiophene-2-carboxylate
201004-08-2

ethyl thieno[3,2,-b]thiophene-2-carboxylate

(2Z)-1-(9-ethyl-9H-carbazol-2-yl)-3-hydroxy-3-thieno[3,2-b]thiophen-2-ylprop-2-en-1-one
1219036-84-6

(2Z)-1-(9-ethyl-9H-carbazol-2-yl)-3-hydroxy-3-thieno[3,2-b]thiophen-2-ylprop-2-en-1-one

Conditions
ConditionsYield
With sodium ethanolate In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;65%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

6-amino-benzo[1,3]dioxole-5-carbaldehyde
23126-68-3

6-amino-benzo[1,3]dioxole-5-carbaldehyde

9-ethyl-3-(6,7-methylenedioxyquinolin-2-yl)-9H-carbazole
1246524-48-0

9-ethyl-3-(6,7-methylenedioxyquinolin-2-yl)-9H-carbazole

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 5h; Reflux;65%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

methyl 4-methoxybenzoate
121-98-2

methyl 4-methoxybenzoate

C24H21NO3

C24H21NO3

Conditions
ConditionsYield
Stage #1: N-ethyl-3-acetylcarbazole With sodium hydride In tetrahydrofuran at 65℃; for 0.5h; Inert atmosphere;
Stage #2: methyl 4-methoxybenzoate In tetrahydrofuran at 65℃; for 24h; Inert atmosphere;
65%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

(2-aminophenyl)(phenyl)methanone
2835-77-0

(2-aminophenyl)(phenyl)methanone

9-ethyl-3-(4-phenylquinolin-2-yl)-9H-carbazole
1239875-14-9

9-ethyl-3-(4-phenylquinolin-2-yl)-9H-carbazole

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 7h; Reflux;59%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

3‐(4‐bromophenyl)‐1‐(9‐ethyl‐9H‐carbazol‐3‐yl)prop‐2‐en‐1‐one

3‐(4‐bromophenyl)‐1‐(9‐ethyl‐9H‐carbazol‐3‐yl)prop‐2‐en‐1‐one

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 24h;57%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

methyl 4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoate
85292-39-3

methyl 4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzoate

1-(9-ethyl-9H-carbazol-3-yl)-3-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]propane-1,3-dione
1191034-17-9

1-(9-ethyl-9H-carbazol-3-yl)-3-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]propane-1,3-dione

Conditions
ConditionsYield
With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Inert atmosphere; Reflux;56%
N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

4-(diphenylamino)benzoic acid methyl ester
25069-30-1

4-(diphenylamino)benzoic acid methyl ester

1-(4-diphenylamino-phenyl)-3-(9-ethyl-9H-carbazol-3-yl)-propane-1,3-dione

1-(4-diphenylamino-phenyl)-3-(9-ethyl-9H-carbazol-3-yl)-propane-1,3-dione

Conditions
ConditionsYield
Stage #1: N-ethyl-3-acetylcarbazole With sodium hydride In tetrahydrofuran at 66℃; for 12h; Claisen Condensation; Reflux;
Stage #2: 4-(diphenylamino)benzoic acid methyl ester In tetrahydrofuran Reflux; Inert atmosphere;
56%
N-ethyl-3-carbazolealdehyde
7570-45-8

N-ethyl-3-carbazolealdehyde

N-ethyl-3-acetylcarbazole
1484-04-4

N-ethyl-3-acetylcarbazole

1,3-bis(9-ethyl-9H-carbazol-3-yl)prop-2-en-1-one
24122-88-1

1,3-bis(9-ethyl-9H-carbazol-3-yl)prop-2-en-1-one

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 24h;55%
With base Aldol condensation;

1484-04-4Relevant articles and documents

A short route to heteroarylcarbazoles: Synthesis of new pyrazolylcarbazoles and carbazolylquinolines

Nagarajan, Rajagopal,Perumal, Paramasivan T.

, p. 1269 - 1273 (2004)

A short synthesis of pyrazolylcarbazoles from 9-alkyl-carbazoles in three steps is reported. The acetylcarbazoles prepared by the acetylation of carbazoles with acetic anhydride catalyzed by BiCl3 were converted into chloroaldehydes with Vilsmeier reagent. Condensation of chloroaldehydes with hydrazine followed by cyclization yield the pyrazolylcarbazoles. Carbazolyl chalcones were prepared by the condensation of carbazole-3-aldehyde with o-aminoacetophenone and cyclized to carbazolylquinolone using several catalysts. Cyclization of carbazolyl chalcones with the Vilsmeier reagent yields a mixture of carbazolylquinoline carbaldehydes.

Facile procedure for the synthesis of 3-acetyl-9-ethylcarbazole and corresponding functionalized bis-diketone compounds

Tang, Rui-Ren,Zhang, Wei

, p. 601 - 606 (2010)

Acetylation-substituted N-ethylcarbazole at the 3-position was synthesized in 80% yield using ZnCl2 as catalyst, and its corresponding functionalized bis-diketone compounds 2a and 2b were prepared by Claisen condensation with acceptable yields.

A New and Facile Method for the Synthesis of Nitrocarbazoles by Urea Nitrate

Nagarajan, Rajagopal,Muralidharan,Perumal, Paramasivan T.

, p. 1259 - 1264 (2004)

Urea nitrate in acetic acid is found to be an effective and mild nitrating agent for the preparation of mono nitrocarbazoles.

Pure Organic Room Temperature Phosphorescence from Excited Dimers in Self-Assembled Nanoparticles under Visible and Near-Infrared Irradiation in Water

Wang, Xiao-Fang,Xiao, Hongyan,Chen, Peng-Zhong,Yang, Qing-Zheng,Chen, Bin,Tung, Chen-Ho,Chen, Yu-Zhe,Wu, Li-Zhu

, p. 5045 - 5050 (2019)

Pure organic room temperature phosphorescence (RTP) has unique advantages and various potential applications. However, it is challengeable to achieve organic RTP under visible and near-infrared (NIR)-light excitation, especially in aqueous solution. Herei

A facile method for the synthesis of acetylcarbazoles and carbazole aldehydes

Nagarajan, Rajagopal,Perumal, Paramasivan T.

, p. 2127 - 2133 (2004)

Acetylation of 9-alkylcarbazoles with acetic anhydride catalyzed by PPh3. HClO4 was reported to give acetylcarbazoles. Carbazole aldehydes were easily synthesized by the Vilsmeier reaction of 9-alkylcarbazoles under microwave condition in good yields.

HS? facilitated sulfur pyran realizing hydrogen sulfide detection and imaging in HepG2 cells and chlorella

Chao, Jianbin,Xu, Miao,Zhang, Yongbin,Huo, Fangjun,Liu, Yaoming,Wang, Xiaolu,Yin, Caixia

, p. 227 - 232 (2019)

The new carbazole-based fluorescent probe CA-1 was designed and synthesized for the high selective detection of H2S based on HS? facilitated sulfur pyran resulting in UV–Vis and fluorescent spectra changes. At the same time, the probe showed good sensitivity to the detection of H2S with a low detection limit of 0.16 μM. The detection process can be monitored by naked eye: with the addition of H2S, the probe system changed from yellow to pink. Importantly, the probe could be applied in monitoring H2S in HepG2 cells and Chlorella. These results indicate that CA-1 can be used as a promising fluorescent probe for the detection of H2S in situ.

Influence of thiophene spacer and auxiliary acceptor on the optical properties of 4-(Diethylamino)-2-hydroxybenzaldehyde based D-π-A-π-D Colorants with N-alkyl donors: Experimental, DFT and Z-scan study

Raikwar, Manish M.,Patil, Dinesh S.,Mathew, Elizabeth,Varghese, Manu,Joe, Issac H.,Sekar, Nagaiyan

, p. 45 - 58 (2019)

We report here design and synthesis of four new D-π-A-π-D type dyes (4 and 5) with triphenylamine/N-ethyl carbazole as fixed rotor/donor and N, N-diethyl amine as a secondary donor having dicyanovinylene as a common acceptor. The Influence of π-linker (thiophene) along with an auxillary cyano group on the nonlinear and linear optical properties is investigated. Molecules with thiophene spacer (4b and 5b) exhibit progressive variation in their absorption and emission profiles reflecting the effect of π-linker, compared to those devoid of thiophene spacer (4a and 5a). The dyes display solvent dependent emission [e.g. 4b (toluene = 689 nm) and 5b (DMSO = 795 nm)] suggesting a more polarized photo-excited state arising as a result of enhanced intramolecular charge transfer in the excited state. The solvatochromic nature is supportive of a general solvent effect, which is confirmed by solvent polarity plots (Weller's and Rettig's plot). The trends in the optical properties were also validated by time dependent density functional theory computations which further reveals charge transfer (from secondary donor to acceptor) for the long wavelength absorption. Dye with the highest charge transfer dipole moment relatively has the maximum two-photon absorption cross-section area (4b = 246–399 GM) which was established using theoretical two-level model. Non-linear optical properties were investigated using solvatochromic two-level model and computationally using global and range separated hybrid functionals. The dyes show high first-order hyperpolarizability (β0) in the range of 191–1162 × 10?30 e.s.u. and second-order hyperpolarizability (γ0) in the range of 491–6,704 × 10?36 e.s.u. Z-scan results show 4a (3.79 × 10?13 e.s.u.) possesses a higher value of third order nonlinear susceptibility in DMSO. Thus, the dyes can be considered as promising candidates for NLO application in material science.

A Solid-State Fluorescent Material Based on Carbazole-Containing Difluoroboron β-Diketonate: Multiple Chromisms, the Self-Assembly Behavior, and Optical Waveguides

Chen, Peng-Zhong,Zhang, Han,Niu, Li-Ya,Zhang, Yi,Chen, Yu-Zhe,Fu, Hong-Bing,Yang, Qing-Zheng

, (2017)

A carbazole-containing difluoroboron β-diketonate complex (BCZ), which shows strong fluorescence in both the solid state and in organic solutions, is reported. The crystalline materials of BCZ obtained from different solvents display different emission colors. Single-crystal analysis reveals that the enhanced overlap between adjacent molecules induces increased excited-state delocalization and is responsible for the variation of the emission colors from yellow to red. The emission colors of the materials are effectively tuned by external stimuli such as grinding, heating, and solvent vapor. The powder X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, and 1H NMR studies on materials of BCZ reveal that the thermochromic properties of BCZ are closely related to the removal of solvent molecules from the crystalline powders upon heating. Moreover, uniform 1D microstructures of BCZ obtained by solvent exchange in solution exhibit optical waveguide property with low optical loss.

Synthesis and application of colorimetric carbazole fluorescent probe for detecting hydrogen sulfide

-

Paragraph 0015, (2018/12/13)

The invention belongs to the technical field of a fluorescent probe, and provides synthesis and application of a colorimetric carbazole fluorescent probe for detecting hydrogen sulfide. The fluorescent probe is 5-chlorine-2-cyano-5-[3-(9-ethyl carbazole)] penta-2,4-ethyl dienoate. 3-acetyl-N-ethyl carbazole is synthesized by using N-ethyl carbazole as a raw material; 3-chlorine-3-[3-(9-ethyl carbazole)] acraldehyde is synthesized; and the 3-chlorine-3-[3-(9-ethyl carbazole)] acraldehyde and ethyl cyanoacetate are dissolved into absolute ethyl alcohol, a catalyst piperidine is added to performa reaction and obtain a crude product, and the crude product is dried to recrystallize the absolute ethyl alcohol, thereby obtaining the fluorescent probe. The probe reacts with the hydrogen sulfide to cause changes of a fluorescence signal and a solution color, and naked eye detection on the hydrogen sulfide can be implemented. The probe has excellent selectivity, is high in detection sensitivity, has a detection limit of 0.16 muM, and can be used for detecting the hydrogen sulfide in cells and chlorella by combining a laser confocal scanning microscopical technique.

Fluorescent probe of reversible sulfur dioxide/sulphurous acid (hydrogen) salt

-

Paragraph 0025; 0026, (2018/06/16)

The invention provides a fluorescent probe of reversible sulfur dioxide/sulphurous acid (hydrogen) salt, with the chemical name of 7-diethylin-2-(9-ethyl-9H-carbazole-3) benzo iso-pyran oxonium ion. The fluorescent probe can detect sulfur dioxide/sulphurous acid (hydrogen) salt in a solution, cells, tissues or a living body, wherein the living body includes fish, mice, rat, guinea pig and rabbit;and reversibility is realized by formaldehyde. The fluorescent probe is simple in synthesis steps, easily available in material, high in yield and suitable for industrial application.

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