132-32-1

Basic information

• Product Name: 3-Amino-9-ethylcarbazole
• Synonyms: TIMTEC-BB SBB000498;2-AMINO-9-ETHYL CARBAZOLE;9-ETHYLCARBAZOL-3-AMINE;9-ETHYL-9H-CARBAZOL-3-YLAMINE;AEC;AEC BUFFER;AEC SINGLE SOLUTION (RED);AEC SUBSTRATE BUFFER
• CAS NO: 132-32-1
• Molecular Formula: C₁₄H₁₄N₂
• Molecular Weight: 210.27
• EINECS: 205-057-7
• Product Categories: Intermediates of Dyes and Pigments;Carbazoles (for Conduting Polymer Research);Carbazoles;Functional Materials;Reagents for Conducting Polymer Research;Biochemistry;Enzyme;Substrates;carbazole;buffer
• Mol File: 132-32-1.mol

Chemical Properties

• Melting Point: 85-88 °C(lit.)
• Boiling Point: 355C
• Flash Point: 208.4 °C
• Appearance: /tablet
• Density: 1,15g/cm
• Vapor Pressure: 2.72E-07mmHg at 25°C
• Refractive Index: 1.6180 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 4.99±0.30(Predicted)
• Water Solubility: <0.1 g/100 mL at 20 C
• BRN: 174969
• CAS DataBase Reference: 3-Amino-9-ethylcarbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-9-ethylcarbazole(132-32-1)
• EPA Substance Registry System: 3-Amino-9-ethylcarbazole(132-32-1)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38-40-23/24/25-45
• Safety Statements: 45-36/37/39-26-22-53
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: FE3590000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 132-32-1(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 132-32-1 differently. You can refer to the following data:
1. brown fine crystalline powder and chunks
2. 3-Amino-9-ethylcarbazole is a brown or tan, crystalline compound.

Uses

Different sources of media describe the Uses of 132-32-1 differently. You can refer to the following data:
1. 3-Amino-9-ethylcarbazole (AEC) has been used as a chromogen in immunohistochemistry to visualize the cells. It has also been used as a substrate in enzyme-linked immune absorbent spot (ELISpot).
2. 3-Amino-9-ethylcarbazole has been used to visualize the bound primary antibody by using a streptavidin method. It has also been used in visualizing tissue sections from tumour samples.

Definition

A hydrochloride salt and free amine solid compound.

General Description

Tan powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

3-Amino-9-ethylcarbazole neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.

Hazard

Questionable carcinogen; poison.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 3-Amino-9-ethylcarbazole emits toxic fumes.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

Safety Profile

Suspected carcinogen with experimental carcinogenic data. Poison by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx,.

Potential Exposure

Plant workers engaged in the manufacture of 3-Amino-9-ethylcarbazole and its use in pigment manufacture. Laboratory workers using this material in colorimetric enzyme assays and as a biological stain

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Incompatibilities

3-Amino-9-ethylcarbazole neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.

Waste Disposal

Incinerator equipped with a scrubber or thermal unit to reduce nitrogen oxides emissions.

InChI:InChI=1/C14H14N2/c1-2-16-13-6-4-3-5-11(13)12-9-10(15)7-8-14(12)16/h3-9H,2,15H2,1H3

Upstream product

• 86-20-4 9-ethyl-3-nitro-carbazole 
• 67-56-1 methanol 
• 104563-32-8 3-azoxy-9-ethylcarbazole 
• 82298-50-8 9,9'-diethyl-Z-3,3'-azocarbazole 
• 86-28-2 N-ethylcarbazole 
• 168060-16-0 9-(3-Methyl-butyl)-3-nitro-9H-carbazole 
• 64-17-5 ethanol 
• 18908-07-1 3-methoxyphenyl isocyanate 
• 144539-45-7 4-methylene-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 15159-48-5 2,4-oxetanedione 
• 621-29-4 3-tolyl isocyanate 
• 4461-33-0 benzoyl isocyanate 
• 34893-92-0 3,4-dichlorophenyl isocyanate 
• 27593-22-2 2-oxo-6-pentyl-2H-pyran-3-carboxylic acid 

Downstream Products

• 121305-18-8 (9-Ethyl-9H-carbazol-3-yl)-[1-(9-ethyl-9H-carbazol-3-yl)-meth-(E)-ylidene]-amine 
• 80236-33-5 (9-Ethyl-9H-carbazol-3-yl)-[1-p-tolyl-meth-(E)-ylidene]-amine 
• 80236-35-7 [1-(4-Chloro-phenyl)-meth-(E)-ylidene]-(9-ethyl-9H-carbazol-3-yl)-amine 
• 52167-08-5 (9-Ethyl-9H-carbazol-3-yl)-[1-(4-nitro-phenyl)-meth-(E)-ylidene]-amine 
• 82298-51-9 N-(9-ethyl-9H-carbazol-3-yl)benzamide 
• 135523-69-2 [(S)-5-(9-Ethyl-9H-carbazol-3-ylcarbamoyl)-5-(2-nitro-phenylsulfanylamino)-pentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 80236-36-8 4-{[(E)-9-Ethyl-9H-carbazol-3-ylimino]-methyl}-benzonitrile 
• 121305-17-7 [1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-(9-ethyl-9H-carbazol-3-yl)-amine 
• 80236-34-6 (9-Ethyl-9H-carbazol-3-yl)-[1-m-tolyl-meth-(E)-ylidene]-amine 
• 811432-28-7 3-hydroxy-9-ethyl-9H-carbazole 
• 331713-74-7 N-(9-ethyl-9H-carbazol-3-yl)-3-oxobutanamide 

Related news

Structural dependences of the η 6 complexes of 3-Amino-9-ethylcarbazole (cas 132-32-1) with chromium tricarbonyl fragment on third-order optical nonlinearities09/30/2019

Degenerate four-wave mixing measurements, using the 35 ps pulses at 532 nm, have been employed to investigate the third-order nonlinear optical parameters of two chromium tricarbonyl complexes η 6-bonded to 3-amino-9-ethylcarbazole at either the NH2-substituted aryl ring (1) or the unsubstitute...detailed

Novel fluorescence sensor based on covalent immobilization of 3-Amino-9-ethylcarbazole (cas 132-32-1) via electrostatically assembled gold nanoparticle layer09/29/2019

A novel technique of immobilizing indicator dyes by electrostatic adsorption and covalent bonding to fabricate optical sensors was developed. 3-Amino-9-ethylcarbazole (AEC) was attached to the outmost surface of quartz glass slide via aminosilanizing the slide, crosslinking chitosan, adsorbing A...detailed

A novel fluorescence sensor based on covalent immobilization of 3-Amino-9-ethylcarbazole (cas 132-32-1) by using silver nanoparticles as bridges and carriers10/01/2019

A novel technique of covalent immobilization of indicator dyes in the preparation of fluorescence sensors is developed. Silver nanoparticles are used as bridges and carriers for anchoring indicator dyes. 3-amino-9-ethylcarbazole (AEC) was employed as an example of indicator dyes with terminal am...detailed

Relevant articles and documents

A carbazole-based turn-on fluorescent probe for the detection of hydrazine in aqueous solution

A carbazole-based fluorescent probe, 2-(9-ethyl-9H-carbazol-3-yl) isoindoline-1,3-dione, with a low detection limit (2.673 × 10?6 M) for the detection of hydrazine is designed and synthesized based on Gabriel reaction. The probe responds selectively to hydrazine over other amino compounds with marked fluorescence enhancement. Moreover, test paper experiments indicated its great potential in the environment monitoring of hydrazine in aqueous solution.

High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates

Commercially available Pd/C can be used as a catalyst for nitro group reductions with only 0.4 mol % Pd loading. The reaction can be performed using either silane as a transfer hydrogenating agent or simply a hydrogen balloon (μ1 atm pressure). With this technology, a series of nitro compounds was reduced to the desired amines in high chemical yields. Both the catalyst and surfactant were recycled several times without loss of reactivity.

Introduction of a luminescent sensor for tracking trace levels of hydrazine in insect pollinated cropland flowers

In recent years the excessive use of hydazine containing chemical pesticides and insecticides in farming practices is well pronounced, which directly or indirectly impart a great threat towards the total environment. Considering the above fact we are motivated to introduce a new, efficient and simple chemodosimeter (NCD) based on a carbazole-naphthalimide framework to recognize and estimate the mutagenic hydrazine within several affected cropland flowers. ProbeNCDcan detect hydrazine in a nanomolar range (65 nM or 2 ppb) in the presence of other metal ions, anions and amines, which gives it not only great potential but also makes it selective and sensitive. The sensing mechanism is confirmed by UV-vis, emission, and mass spectroscopy, and computational studies. We have successfully characterized probeNCDby1H and13C NMR and mass spectrometry as well as by single crystal analysis.

Copper(II)-Catalyzed Iodinations of Carbazoles: Access to Functionalized Carbazoles

A copper-catalyzed iodination of carbazoles has been developed. Barluenga's reagent IPy2BF4 is used to generate a soft electrophilic halonium species for the iodination of the carbazoles. This report represents the first concept of copper-catalyst-promoted electrophilic halogenation of carbazoles. We demonstrated numerous applications of this methodology synthesizing diverse carbazole derivatives, i.e., both electron-rich and electron-deficient systems.

Use for RL intermediate condensation product synthesis process (by machine translation)

The present invention discloses a use for RL intermediate condensation product synthesis process, the process comprises the steps of: carbazole alkylation N - ethyl carbazole made, by nitration, reduction to generate a 3 - amino - N - ethyl carbazole, then in the organic solvent in the condensation reaction, use for intermediate condensate obtained RL; in this invention the condensation reaction using an alcohol as a solvent to replace the traditional O-chlorobenzene, improves the 3 - amino - N - ethyl carbazole conversion rate, and improves the use for RL crude purity and yield, and the process is stable, simple operation, high safety factor. (by machine translation)

Novel Schiff base compound taking triphenylamine as center and preparation of novel Schiff base compound

The invention provides a novel Schiff base compound taking triphenylamine as a center and having a structural formula I, and a preparation method of the novel Schiff base compound. The preparation method comprises steps of: reacting triphenylamine with DMF and POCl3 to prepare 4,4-diformyltriphenylamine; preparing N-ethylcarbazole from carbazole and bromoethane; nitrifying N-ethylcarbazole to obtain 3-nitro-N-ethylcarbazole; further reducing nitro to obtain 3-amino-N-ethylcarbazole; and finally reacting 4,4-diformyltriphenylamine with 3-nitro-N-ethylcarbazole to obtain the Schiff base compound. The prepared Schiff base compound has carbon-nitrogen double bonds (C=N) and a relatively large pi electron delocalization skeleton, which provides the compound with a relatively large fluorescence absorption coefficient. Due to the presence of lone pair electrons of C=N, the novel Schiff base compound has a potential application to detection of metal ions.

Substituted Carbazoles-A New Class of Anthelmintic Agent

A series of novel carbazoles were synthesized based on structural modifications to lead carbazole 1 (EC100≤2.5M against Haemonchus contortus in vitro), which was revealed in a small molecule screening program as a potentially promising platform for the development of new anthelmintic drugs. Subsequently, analogues 19, 21, 41, 42 (EC100≤ 1.25M, all), and 39 (EC100≤0.625M) were demonstrated to exhibit enhanced in vitro anthelmintic activity over the lead structure, with compound 39 also being shown to be active in vivo against Heligmosomoides polygyrus.

Turn-on trivalent cation selective chemodosimetric probe to image native cellular iron pools

A new turn-on cell permeable chemodosimetric probe 1 has been developed and its application in the selective detection of trivalent cations (Fe 3+/Cr3+/Al3+) at a sub-nanomolar level has been demonstrated. The selectivity of 1 over a broad spectrum of mono- and divalent metal ions was established using fluorescence spectroscopy. Moreover, the changes in the absorption spectra of 1 in the presence of trivalent cations enabled the most bio-relevant metal ion Fe3+ over Cr 3+/Al3+ to be distinguished. The probe was found to be successful in the fluorescence imaging of native cellular iron pools. The fluorescence imaging of the native iron pools of banana pith further supported the high sensitivity of 1 towards Fe3+ present in living systems. To the best of our knowledge, this is the first example of a turn-on chemodosimetric probe to image native cellular Fe3+ pools. This journal is the Partner Organisations 2014.

Carbazole N-substituent effect upon DTMA: Stabilizing and photochromic modulating

Dithienylmaleimide derivatives 7-27 were synthesized by introducing N-substituted carbazole for photo-stabilizing purpose, and the structures were fully confirmed. The photochromism and photo-stability were recorded via UV-vis spectra. Only ortho compounds 8-17 with N-substituents on carbazole moiety showed escalated photochromic change, while compound 7 and the para counterparts 18-27 showed no appreciable photochromism. Additionally, compounds 8-18 exhibited good photo-stability except 17 under 254 nm irradiation. The unstability of 17 may probably due to overrunning hindrance. These photochromic patterns indicated that hindrance and electronic effect mutually paid a decisive influence on the photochromism and photo-stability, which potentially exploited a new way to construct novel photochromic materials with regulable and conceivable performance.

Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts

A method for the Pd-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, including challenging five-membered heterocyclic substrates, is described. Excellent selectivity for monoarylation of ammonia to primary arylamines was achieved under mild conditions or at rt by the use of bulky biarylphosphine ligands (L6, L7, and L4) as well as their corresponding aminobiphenyl palladacycle precatalysts (3a, 3b, and 3c). As this process requires neither the use of a glovebox nor high pressures of ammonia, it should be widely applicable.