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Naphthol AS-E

Product Name
Naphthol AS-E
CAS No.
92-78-4
Chemical Name
Naphthol AS-E
Synonyms
nAS-E;C.I. 37510;Naftol AS-E;NAPTHOL AS-E;NAPHTHOL AS-E;Amarthol AS-E;DaitoGrounderE;AcnaNaphtholPC;Kiwa Grounder E;92-78-4 Naphthol AS-E
CBNumber
CB4723659
Molecular Formula
C17H12ClNO2
Formula Weight
297.74
MOL File
92-78-4.mol
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Naphthol AS-E Property

Melting point:
255°C
Boiling point:
416.5±30.0 °C(Predicted)
Density 
1.399±0.06 g/cm3(Predicted)
vapor pressure 
0Pa at 25℃
storage temp. 
Sealed in dry,Room Temperature
solubility 
soluble in Dimethylformamide
pka
8.69±0.40(Predicted)
form 
Beige solid
Colour Index 
37510
color 
White to Light yellow to Dark green
LogP
2.97 at 23℃ and pH7.2
CAS DataBase Reference
92-78-4(CAS DataBase Reference)
EPA Substance Registry System
2-Naphthalenecarboxamide, N-(4-chlorophenyl)-3-hydroxy- (92-78-4)
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Safety

HS Code 
2924.29.7790
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
S504041
Product name
4'-CHLORO-3-HYDROXY-2-NAPHTHANILIDE
Purity
AldrichCPR
Packaging
25mg
Price
$179
Updated
2024/03/01
Sigma-Aldrich
Product number
217505
Product name
CBP-CREB Interaction Inhibitor
Packaging
250mg
Price
$99.4
Updated
2024/03/01
TCI Chemical
Product number
C2103
Product name
4'-Chloro-3-hydroxy-2-naphthanilide
Purity
>97.0%(N)
Packaging
25g
Price
$146
Updated
2024/03/01
TRC
Product number
C587828
Product name
4''-Chloro-3-hydroxy-2-naphthanilide
Packaging
5g
Price
$60
Updated
2021/12/16
Biosynth Carbosynth
Product number
FA41321
Product name
C.I.Azoic Coupling Component 10
Packaging
10g
Price
$55
Updated
2021/12/16
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Naphthol AS-E Chemical Properties,Usage,Production

Uses

Naphthol AS-E is mainly used for dyeing cotton, and also for dyeing viscose fiber and silk. It is often used in combination with blue base or blue salt to dye dark blue and navy blue.

Preparation

4-Chlorobenzenamine and 3-Hydroxy-2-naphthoic acid condensation.

General Description

A cell-permeable naphthamide compound that effectively blocks the interaction between the KIX domain of CBP and the KID domain of CREB in HEK293T-based and cell-free Renilla luciferase (RLuc) complementation assays (IC50 = 2.26 and 2.9 M, respectively) by directly binding to CBP′s KIX domain (Kd ~8.6 M using a recombinant KIX). Shown to inhibit CRE- (cAMP response element) dependent transcription activity induced by forskolin in a HEK293T-based RLuc reporter assay (IC50<2.5 M), while exhibiting little effect against the KID-independent CREB-VP16 transcription activity. Also reported to inhibit the enzymatic activity of Firefly luciferase (IC50 ~1 M), but not that of RLuc.

Biological Activity

NaphtholAS-E is a potent, cell-permeable inhibitor of the KIX-KID interaction. NaphtholAS-E directly binds to the KIX domain of CBP (Kd: 8.6μM) and blocks the interaction between the KIX and KID domains (IC50: 2.26μM). NaphtholAS-E can be used in cancer research.

Synthesis

Naphthol AS-E is synthesized with 2,3-acid and p-chloroaniline as raw materials and chlorobenzene as solvent. First, 2,3-acid is made into sodium salt, and then condensed with p-chloroaniline in the presence of PCl3, and the finished product is obtained by neutralization, distillation, filtration and drying.

in vitro

CREB (cyclic AMP-response element-binding protein) is a downstream transcription factor of a multitude of signaling pathways emanating from receptor tyrosine kinases or G-protein coupled receptors.CREB can not be activated until it is phosphorylated at Ser133 and its subsequent binding to CREB-binding protein (CBP) through the kinase-inducible domain (KID) in CREB and KID-interacting (KIX) domain in CBP.In a cell-based CREB Renilla luciferase reporter assay, Naphthol AS-E inhibits CREB-mediated gene transcription with an IC 50 of 2.29 μM. In HEK293T-based complementation assay, Naphthol AS-E dose-dependently inhibited Renilla luciferase activity with an IC 50 of 2.9 μM by directly binding to CBP's KIX domain (K d ~8.6 μM using a recombinant KIX).Naphthol AS-E exhibits low μM activity in inhibiting the proliferation of all these cancer cells, which is consistent with its cellular CREB inhibition potency. The average GI 50 values for A549, MCF-7, MDA-MB-231 and MDA-MB-468 are approximately 2.9μM, 2.81μM, 2.35μM and 1.46μM, respectively.Naphthol AS-E (2.5 μM-10 μM; 48 hours) decreases the expression of anti-apoptotic protein Bcl-2. The expression of VEGF is also decreased.

Properties and Applications

light yellow microstrip red uniform powder, melting point for 258 ~ 259 ℃. Insoluble in water solution and sodium carbonate, soluble in adjacent two chlorobenzene, ethanol and glacial acetic acid. Sodium hydroxide solution for yellow in the liquid. Sensitive to air. Mainly used for cotton fabrics, viscose and silk dyeing, general is not used for printing, and can be used as organic pigments intermediate. This product to cotton affinity is higher, coupled ability medium.

Naphthol AS-E Preparation Products And Raw materials

Raw materials

Preparation Products

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Naphthol AS-E Suppliers

Alfa Chemistry
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View Lastest Price from Naphthol AS-E manufacturers

Career Henan Chemical Co
Product
Naphthol AS-E 92-78-4
Price
US $1.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
100KG
Release date
2018-12-24

92-78-4, Naphthol AS-ERelated Search:


  • NAPHTHOL AS-E
  • NAPTHOL AS-E
  • N-(4-CHLOROPHENYL)-3-HYDROXY-2-NAPHTHAMIDE
  • c.i. azoic coupling component 10
  • AZOIC COUPLING COMPONENT 10
  • 4'-CHLORO-3-HYDROXY-2-NAPHTHANILIDE
  • AcnaNaphtholPC
  • DaitoGrounderE
  • n-(4-chlorophenyl)-3-hydroxy-2-naphthalenecarboxamid
  • 2-Hydroxy-3-Naphthoyl-p-Chloraniline
  • 2-Naphthalenecarboxamide-N-(4-chlorophenyl)-3-hydroxy
  • 4′-Chlor-3-hydroxy-2-naphthanilid
  • Naphthol AS-E (C.I. 37510)
  • 4''-CHLORO-3-HYDROXY-2-NAPHTHANILIDE 97.0+%(T)
  • C.I. 37510
  • Amarthol AS-E
  • Kiwa Grounder E
  • Naftol AS-E
  • CBP-CREB Interaction Inhibitor
  • N-(4-Chlorophenyl)-3-hydroxynaphthalene-2-carboxamide
  • N-(4-Chlorophenyl)-3-hydroxy-2-naphthamide Naphthol AS-E Azoic Coupling Component 10
  • nAS-E
  • N-(4-Chlorophenyl)-3-hydroxy-2-naphthalenecarboxamide
  • CBP-CREB Interaction Inhibitor - CAS 92-78-4 - Calbiochem
  • 4'-Chloro-3-hydroxy-2-naphthanilide &gt
  • Naphthol AS-E ISO 9001:2015 REACH
  • Naphthol AS-E (4'-Chloro-3-hydroxy-2-naphthanilide)
  • C.I.Azoic Coupling Component 10:C.I.37510
  • 92-78-4 Naphthol AS-E
  • 4'-Chloro-3-hydroxy-2-naphthanilide
  • 92-78-4
  • AMINE
  • Substrates
  • Intermediates of Dyes and Pigments