Product Name

  • Name

    Naphthol AS-E

  • EINECS 202-189-7
  • CAS No. 92-78-4
  • Article Data10
  • CAS DataBase
  • Density 1.399 g/cm3
  • Solubility
  • Melting Point 255 °C
  • Formula C17H12ClNO2
  • Boiling Point 416.5 °C at 760 mmHg
  • Molecular Weight 297.741
  • Flash Point 205.7 °C
  • Transport Information
  • Appearance off-white powder
  • Safety
  • Risk Codes R42/43
  • Molecular Structure Molecular Structure of 92-78-4 (Naphthol AS-E)
  • Hazard Symbols Xn
  • Synonyms Dycosthol AS-E;Hiltonaphthol AS-E;Kiwa Grounder E;NSC 50684;Naftol AS-E;Naphtazol E;Naphthol ACNA PC;Naphthol AS-E;Naphtoelan E;Napthol ASE;Sanatol E;2-Naphthanilide,4'-chloro-3-hydroxy- (6CI,7CI,8CI);3-Hydroxy-4'-chloro-2-naphthanilide;Acna Naphthol PC;Amanil Naphthol AS-E;Amarthol AS-E;Azoic Coupling Component 10;C.I. 37510;Cibanaphthol RC;Daito Grounder E;
  • PSA 49.33000
  • LogP 4.52410

Synthetic route

4-chloro-aniline
106-47-8

4-chloro-aniline

3-Hydroxy-2-naphthoic acid
92-70-6

3-Hydroxy-2-naphthoic acid

naphthol AS-E
92-78-4

naphthol AS-E

Conditions
ConditionsYield
With phosphorus trichloride In chlorobenzene at 100 - 130℃; for 0.75h; Microwave irradiation;71%
With phosphorus trichloride 1) xylene, 80 deg C, 10 min; 2) xylene, reflux, 2 h; Multistep reaction;
Acylation;
4-Chlorophenyl isothiocyanate
2131-55-7

4-Chlorophenyl isothiocyanate

3-Hydroxy-2-naphthoic acid
92-70-6

3-Hydroxy-2-naphthoic acid

naphthol AS-E
92-78-4

naphthol AS-E

Conditions
ConditionsYield
at 220℃;
3-hydroxy-2-naphthoyl chloride
1734-00-5

3-hydroxy-2-naphthoyl chloride

4-chloro-aniline
106-47-8

4-chloro-aniline

naphthol AS-E
92-78-4

naphthol AS-E

Conditions
ConditionsYield
With sodium acetate In N,N-dimethyl-formamide; chlorobenzene at 5 - 50℃;
[3-[(4-chlorophenyl)carbamoyl]-naphthalen-2-yl] dihydrogen phosphate

[3-[(4-chlorophenyl)carbamoyl]-naphthalen-2-yl] dihydrogen phosphate

naphthol AS-E
92-78-4

naphthol AS-E

Conditions
ConditionsYield
With water at 37℃; for 29.2h; Kinetics;
naphthol AS-E
92-78-4

naphthol AS-E

1-(p-sulphophenyl)-3-methyl-4-amino-5-pyrazolone

1-(p-sulphophenyl)-3-methyl-4-amino-5-pyrazolone

C27H20ClN5O6S

C27H20ClN5O6S

Conditions
ConditionsYield
Stage #1: 1-(p-sulphophenyl)-3-methyl-4-amino-5-pyrazolone With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1h;
Stage #2: naphthol AS-E With sodium carbonate; sodium hydroxide In water at 0 - 5℃; for 4.5h; pH=8 - 9;
80.72%
N-tert-butoxycarbonyl-3-aminopropanol
58885-58-8

N-tert-butoxycarbonyl-3-aminopropanol

naphthol AS-E
92-78-4

naphthol AS-E

tert-butyl (3-((3-((4-Chlorophenyl)carbamoyl)naphthalen-2-yl)oxy)propyl)carbamate
1224567-51-4

tert-butyl (3-((3-((4-Chlorophenyl)carbamoyl)naphthalen-2-yl)oxy)propyl)carbamate

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;78%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;77%
naphthol AS-E
92-78-4

naphthol AS-E

11-amino-3-bromo-13H-acenaphtho[1,2-e]pyridazino[3,2-b]quinazoline-13-one
443288-66-2

11-amino-3-bromo-13H-acenaphtho[1,2-e]pyridazino[3,2-b]quinazoline-13-one

C38H20BrClN6O3

C38H20BrClN6O3

Conditions
ConditionsYield
Stage #1: 11-amino-3-bromo-13H-acenaphtho[1,2-e]pyridazino[3,2-b]quinazoline-13-one With hydrogenchloride; sodium nitrite at 0 - 5℃;
Stage #2: naphthol AS-E In alkaline aq. solution at 0 - 5℃;
70%
oxalyl dichloride
79-37-8

oxalyl dichloride

naphthol AS-E
92-78-4

naphthol AS-E

3-(4-chlorophenyl)-2H-naphtho[2,3-e][1,3]oxazine-2,4-(3H)-dione
58523-68-5

3-(4-chlorophenyl)-2H-naphtho[2,3-e][1,3]oxazine-2,4-(3H)-dione

Conditions
ConditionsYield
In para-xylene at 120℃;52%
naphthol AS-E
92-78-4

naphthol AS-E

tert-butyl N-tosyloxycarbamate
105838-14-0

tert-butyl N-tosyloxycarbamate

3-{[(tert-butoxycarbonyl)amino]oxy}-2-naphthoic acid
1448026-34-3

3-{[(tert-butoxycarbonyl)amino]oxy}-2-naphthoic acid

Conditions
ConditionsYield
Stage #1: naphthol AS-E With potassium hexamethylsilazane In tetrahydrofuran at 0℃; for 0.25h;
Stage #2: tert-butyl N-tosyloxycarbamate With n-butyllithium In tetrahydrofuran at -78 - 0℃;
31%
2,3-Dichloro-1,4-naphthoquinone
117-80-6

2,3-Dichloro-1,4-naphthoquinone

naphthol AS-E
92-78-4

naphthol AS-E

8,13-dioxo-8,13-dihydro-dinaphtho[2,1-b;2',3'-d]furan-6-carboxylic acid-(4-chloro-anilide)
121967-30-4

8,13-dioxo-8,13-dihydro-dinaphtho[2,1-b;2',3'-d]furan-6-carboxylic acid-(4-chloro-anilide)

Conditions
ConditionsYield
With pyridine
naphthol AS-E
92-78-4

naphthol AS-E

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

3-(4-chlorophenyl)-2H-naphtho[2,3-e][1,3]oxazine-2,4-(3H)-dione
58523-68-5

3-(4-chlorophenyl)-2H-naphtho[2,3-e][1,3]oxazine-2,4-(3H)-dione

Conditions
ConditionsYield
In pyridine
naphthol AS-E
92-78-4

naphthol AS-E

[3-[(4-chlorophenyl)carbamoyl]-naphthalen-2-yl] dihydrogen phosphate

[3-[(4-chlorophenyl)carbamoyl]-naphthalen-2-yl] dihydrogen phosphate

Conditions
ConditionsYield
With phosphorus pentachloride In 1,4-dioxane at 50℃; for 1h;
naphthol AS-E
92-78-4

naphthol AS-E

diazotized 1-amino-9.10-dioxo-9.10-dihydro-anthracene-carbaldehyde-(2)

diazotized 1-amino-9.10-dioxo-9.10-dihydro-anthracene-carbaldehyde-(2)

4-(2-formyl-9,10-dioxo-9,10-dihydro-[1]anthrylazo)-3-hydroxy-[2]naphthoic acid-(4-chloro-anilide)

4-(2-formyl-9,10-dioxo-9,10-dihydro-[1]anthrylazo)-3-hydroxy-[2]naphthoic acid-(4-chloro-anilide)

1,5-diaminoanthraquinone
129-44-2

1,5-diaminoanthraquinone

naphthol AS-E
92-78-4

naphthol AS-E

C48H28Cl2N6O6

C48H28Cl2N6O6

Conditions
ConditionsYield
Stage #1: 1,5-diaminoanthraquinone With hydrogenchloride; sodium nitrite Diazotization;
Stage #2: naphthol AS-E With sodium acetate Substitution;
naphthol AS-E
92-78-4

naphthol AS-E

epichlorohydrin
106-89-8

epichlorohydrin

C20H16ClNO3
1174069-46-5

C20H16ClNO3

Conditions
ConditionsYield
With sodium hydroxide In methanol
naphthol AS-E
92-78-4

naphthol AS-E

3-{[(tert-butoxycarbonyl)amino]oxy}-2-naphthoic methanesulfonic anhydride
1448026-35-4

3-{[(tert-butoxycarbonyl)amino]oxy}-2-naphthoic methanesulfonic anhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C
1.2: -78 - 0 °C
2.1: triethylamine / tetrahydrofuran / 4 h / 0 - 20 °C
View Scheme
naphthol AS-E
92-78-4

naphthol AS-E

tert-butyl {3-[(4-chlorophenyl)carbamoyl]naphthalen-2-yl}oxycarbamate
1448026-36-5

tert-butyl {3-[(4-chlorophenyl)carbamoyl]naphthalen-2-yl}oxycarbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C
1.2: -78 - 0 °C
2.1: triethylamine / tetrahydrofuran / 4 h / 0 - 20 °C
3.1: dmap / toluene / 140 °C / Sealed tube
View Scheme
naphthol AS-E
92-78-4

naphthol AS-E

3-[(tert-butylamino)oxy]-N-(4-chlorophenyl)-2-naphthamide
1448026-37-6

3-[(tert-butylamino)oxy]-N-(4-chlorophenyl)-2-naphthamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C
1.2: -78 - 0 °C
2.1: triethylamine / tetrahydrofuran / 4 h / 0 - 20 °C
3.1: dmap / toluene / 140 °C / Sealed tube
4.1: hydrogenchloride / methanol; diethyl ether; chloroform / 20 °C
View Scheme
naphthol AS-E
92-78-4

naphthol AS-E

3-(3-aminopropoxy)-N-(4-chlorophenyl)-2-naphthamide
1224567-47-8

3-(3-aminopropoxy)-N-(4-chlorophenyl)-2-naphthamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C
2: hydrogenchloride / diethyl ether; chloroform; methanol / 20 °C
View Scheme
naphthol AS-E
92-78-4

naphthol AS-E

tert-butyl (3-((3-((3-((3-((4-Chlorophenyl)carbamoyl)-naphthalen-2-yl)oxy)propyl)carbamoyl)naphthalen-2-yl)oxy)-propyl)carbamate

tert-butyl (3-((3-((3-((3-((4-Chlorophenyl)carbamoyl)-naphthalen-2-yl)oxy)propyl)carbamoyl)naphthalen-2-yl)oxy)-propyl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C
2: hydrogenchloride / diethyl ether; chloroform; methanol / 20 °C
3: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 20 °C
View Scheme
naphthol AS-E
92-78-4

naphthol AS-E

2-methyl-5-nitroaniline
99-55-8

2-methyl-5-nitroaniline

pigment red 8

pigment red 8

Conditions
ConditionsYield
Stage #1: 2-methyl-5-nitroaniline With hydrogenchloride In water at 70℃; for 1h;
Stage #2: With sodium nitrite In water for 1.5h;
Stage #3: naphthol AS-E Further stages;
naphthol AS-E
92-78-4

naphthol AS-E

3-(3-aminopropoxy)-N-(4-chlorophenyl)-2-naphthamide hydrochloride
1224567-34-3

3-(3-aminopropoxy)-N-(4-chlorophenyl)-2-naphthamide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 20 °C
2: hydrogenchloride / tetrahydrofuran; water / 20 °C
View Scheme

Naphthol AS-E Chemical Properties

Product Name: 2-Naphthalenecarboxamide,N-(4-chlorophenyl)-3-hydroxy- (CAS NO.92-78-4)


Molecular Formula: C17H12ClNO2
Molecular Weight: 297.74g/mol
Mol File: 92-78-4.mol
EINECS: 202-189-7
Melting Point: 255°C
Boiling point: 416.5 °C at 760 mmHg
Flash Point: 205.7 °C
Density: 1.399 g/cm3
Surface Tension: 63.8 dyne/cm
Enthalpy of Vaporization: 69.57 kJ/mol
Vapour Pressure: 1.57E-07 mmHg at 25°C
XLogP3-AA: 4.8
H-Bond Donor: 2
H-Bond Acceptor: 2
Structure Descriptors of 2-Naphthalenecarboxamide,N-(4-chlorophenyl)-3-hydroxy- (CAS NO.92-78-4):
  IUPAC Name: N-(4-chlorophenyl)-3-hydroxynaphthalene-2-carboxamide
  Canonical SMILES: C1=CC=C2C=C(C(=CC2=C1)C(=O)NC3=CC=C(C=C3)Cl)O
  InChI: InChI=1S/C17H12ClNO2/c18-13-5-7-14(8-6-13)19-17(21)15-9-11-3-1-2-4-12(11)10-16(15)20/h1-10,20H,(H,19,21) 
  InChIKey: OHAXNCGNVGGWSO-UHFFFAOYSA-N
Product Categories: Intermediates of Dyes and Pigments; Substrates

Naphthol AS-E Specification

 2-Naphthalenecarboxamide,N-(4-chlorophenyl)-3-hydroxy- , its CAS NO. is 92-78-4, the synonyms are Acna Naphthol PC ; Amanil Naphthol AS-E ; Azoic Coupling Component 10 ; C.I. 37510 ; C.I. Azoic Coupling Component 10 ; Cibanaphthol RC ; Daito Grounder E ; Hiltonaphthol AS-E ; Naphtanilide E ; Sanatol E ; Tulathol AS-E ; 2-Naphthanilide, 4'-chloro-3-hydroxy- (8CI) ; 4'-Chloro-3-hydroxy-2-naphthanilide .

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