93-05-0

Usage

Uses

Used in Dye Industry:
N,N-Diethyl-1,4-phenylenediamine is used as a dye intermediate for the synthesis of various dyes, contributing to the production of a wide range of colored compounds used in different applications.
Used in Diazo Copying Process:
In the diazo copying process, N,N-Diethyl-1,4-phenylenediamine serves as a source of diazonium compounds, which are essential for the formation of diazo dyes and the reproduction of images on copying paper.
Used in Scientific Research:
N,N-Diethyl-1,4-phenylenediamine is employed as a reference probe in the study of rapid chlorination rate constants. This application aids researchers in understanding and measuring the kinetics of chemical reactions, which is crucial for various scientific and industrial applications.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

N,N-Diethyl-1,4-phenylenediamine 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. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

N,N-Diethyl-1,4-phenylenediamine is probably combustible.

Safety Profile

Poison by ingestion, skin contact, subcutaneous, and intravenous routes. Human systemic skin effects by skin contact: hemorrhage, allergic dermatitis, and primary irritation. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also AMINES.

Upstream product

• 13059-73-9 C₁₉H₁₉N₃O₂ 
• 87986-73-0 N,N-diethyl-4-(phenylazo)-benzeneamine 
• 39868-95-6 4-(4-Diethylamino-phenylazo)-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 76712-19-1 N,N-diethyl-N'-(4-nitro-benzylidene)-p-phenylenediamine 
• 120-22-9 N,N-diethyl-4-nitrosoaniline 
• 104007-17-2 2-[(4-diethylaminophenylamino)methylene]malonic acid diethyl ester 
• 106-39-8 bromochlorobenzene 
• 6283-63-2 4-[N,N-diethylamino]-aniline sulfate 
• 29812-35-9 N,N-Diethyl-p-benzochinondiimin 
• 91-66-7 N,N-diethylaniline 
• 547-58-0 methyl orange 
• 2216-15-1 1-diethylamino-4-nitrobenzene 
• 350-46-9 4-Fluoronitrobenzene 
• 64-17-5 ethanol 

Downstream Products

• 117985-07-6 4-Diethylamino-phenylimino-3-methyl-1-phenyl-2-pyrazolin-5-on 
• 111583-59-6 4-(4-diethylamino-phenylimino)-5-methyl-2-p-tolyl-2,4-dihydro-pyrazol-3-one 
• 68719-66-4 5-amino-4-(4-diethylamino-phenylimino)-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 118717-23-0 4-(4-diethylamino-phenylimino)-2,5-diphenyl-2,4-dihydro-pyrazol-3-one 
• 76712-19-1 N,N-diethyl-N'-(4-nitro-benzylidene)-p-phenylenediamine 
• 101578-08-9 N-(4-diethylamino-phenyl)-N'-phenyl-urea 
• 125983-31-5 chloro-acetic acid-(4-diethylamino-anilide) 
• 5775-53-1 N,N-diethyl-N',N'-dimethyl-p-phenylenediamine 
• 74347-02-7 N,N'-bis-(4-diethylamino-phenyl)-thiourea 
• 32387-68-1 (4-diethylamino-anilino)-methanesulfonic acid 
• 49645-14-9 N,N'-diethyl-N,N'-p-phenylene-bis-formamide 
• 2363-99-7 4-[[4-(diethylamino)phenyl]imino]-1(4H)-naphthalenone 

Relevant academic research and scientific papers

Photoreductive chlorine elimination from a Ni(iii)Cl2complex supported by a tetradentate pyridinophane ligand

Herein we report the isolation, characterization, and photoreactivity of a stable NiIIIdichloride complex supported by a tetradentate pyridinophane N-donor ligand. Upon irradiation, this complex undergoes an efficient photoreductive chlorine elimination reaction, both in solution and the solid-state. Subsequently, the NiIIICl2species can be regeneratedviaa reaction with PhICl2

Optimization of WZ4003 as NUAK inhibitors against human colorectal cancer

NUAK, the member of AMPK (AMP-activated protein kinase) family of protein kinases, is phosphorylated and activated by the LKB1 (liver kinase B1) tumor suppressor protein kinase. Recent work has indicated that NUAK1 is a key component of the antioxidant stress response pathway, and the inhibition of NUAK1 will suppress the growth and survival of colorectal tumors. As a promising target for anticancer drugs, few inhibitors of NUAK were developed. With this goal in mind, based on NUAK inhibitor WZ4003, a series of derivatives has been synthesized and evaluated for anticancer activity. Compound 9q, a derivative of WZ4003 by removing a methoxy group, was found to be the most potential one with stronger inhibitory against NUAK1/2 enzyme activity, tumor cell proliferation and inducing apoptosis of tumor cells. By in vivo efficacy evaluations of colorectal SW480 xenografts, 9q suppresses tumor growth more effectively with an excellent safety profile in vivo and is therefore seen as a suitable candidate for further investigation.

Preparation method of cationic blue dye

The invention belongs to the technical field of dyes, and particularly relates to a preparation method of a cationic blue dye. According to the invention, a compound II is used as a diazonium component and a compound I is used as a coupling component for synthesizing the cationic blue dye for the first time; and the method has the advantages of simple process, environmental friendliness, high product purity, high yield and the like. The results of multiple production experiments with scales not below pilot tests show that mother liquor (such as mother liquor in steps 2, 3 and 4) in the reaction process can be cyclically used 6-8 times without treatment, so the amount of high-salt, high-COD and high-chroma wastewater is greatly reduced, a working environment is effectively improved while product yield is further increased and reaction reagent cost is saved, and the product still keeps high purity; and thus, product quality is guaranteed, production cost is reduced, and obvious economicbenefits, social benefits and environmental benefits are produced.

Co/Cu bimetallic ZIF as New heterogeneous catalyst for reduction of nitroarenes and dyes

Nowadays one of the great challenges is to design new bimetallic catalysts with enhanced catalytic activity, selectivity and recycling properties. In this work, the preparation of new Co/Cu bimetallic Zeolitic Imidazolate Framework (Co-Cu/ZIF) as an efficient catalyst for the reduction of nitro compounds and organic dyes is described. Co-Cu/ZIF was characterized with different techniques such as SEM, TEM, XRD, XPS, TGA, FT-IR and UV–vis absorption indicating formation of entirely uniform cubic particles. Using this catalyst, structurally different aromatic nitro compounds were reduced efficiently to corresponding amines in excellent yields. Kinetic studies revealed that the reduction rates of nitrophenol isomers follow 3-NP > 4-NP > 2-NP order. The catalytic activity of Co-Cu/ZIF was further investigated in the reduction of organic dyes such as methyl orange (MO) and rhodamine B (RhB). This catalyst was recycled for at least ten runs in the reduction of 4-nitrophenol without a noticeable decrease in activity and reused catalyst was characterized.

Discovery of benzo[d]oxazole derivatives as the potent type-I FLT3-ITD inhibitors

Fms-like tyrosine kinase 3 (FLT3) has been considered as a potential drug target for the treatment of acute myeloid leukemia (AML), because of its high and aberrant expression in AML patients, especially the patients with FLT3-ITD mutation. Initiating from a hit compound (IC50: 500 nM against FLT3-ITD), a series of compounds were designed and synthesized based on benzo[d]oxazole-2-amine scaffold to discover new potent FLT3-ITD inhibitors. During the medicinal chemistry works, flexible molecular docking was used to provide design rationale and study the binding modes of the target compounds. Through the mixed SAR exploration based on the enzymatic and cellular activities, compound T24 was identified with potent FLT3-ITD inhibitory (IC50: 0.41 nM) and anti-proliferative (IC50: 0.037 μM against MV4-11 cells) activities. And the binding mode of T24 with “DFG-in” FLT3 was simulated by a 20-ns molecular dynamics run, providing some insights into further medicinal chemistry efforts toward novel FLT3 inhibitors in AML therapy.

Catalyst-Directed Chemoselective Double Amination of Bromo-chloro(hetero)arenes: A Synthetic Route toward Advanced Amino-aniline Intermediates

A chemoselective sequential one-pot coupling protocol was developed for preparing several amino-anilines in high yield as building blocks for active pharmaceutical ingredients (APIs). Site (Cl vs Br on electrophile) and nucleophile (amine vs imine) selectivity is dictated by the catalyst employed. A Pd-crotyl(t-BuXPhos) precatalyst selectively coupled the Ar-Br of the polyhaloarene with benzophenone imine, even in the presence of a secondary amine, while Pd-based RuPhos or (BINAP)Pd(allyl)Cl coupled the Ar-Cl site with secondary amines.

A NIR turn-on fluorescent probe applied in cytochrome P450 reductase detection and hypoxia imaging in tumor cells

In?vivo monitoring of the hypoxic area is urgently required. Near infrared (NIR) fluorescence-active fluorophores with excellent photo stability are preferable for in?vivo imaging. A novel rational designed turn-on fluorescent probe with high selectivity and long-wavelength was synthesized which was applied in bioreductase (cytochrome P450 reductase which overexpressed in tumor cells) and hypoxia detection. The NIR probe (AZO-DCM) is based on a photo stability fluorophore dicyanomethylene-4H-pyran dye (DCM) with an azo bond as probe quencher and hypoxic trigger. After reacted with cytochrome P450 reductase, azo bond was cleaved and DCM released with fluorescent on. The designed probe showed high anti-interference ability which cannot disturb by many interfering substances, such as biothiols, inorganic salts (included sulfite salt) and amino acid. AZO-DCM performed good selectivity and sensitivity to cytochrome P450 reductase and hypoxia. The fluorescent intensity was increased more than 150-fold after response to cytochrome P450 reductase and NADH system in 4?min. The reaction mechanism also proved by HPLC experiment. Probe AZO-DCM displayed excellent properties in identifying different hypoxic status of tumor cells in?vivo.

Discovery of Potent, Selective Stem Cell Factor Receptor/Platelet Derived Growth Factor Receptor Alpha (c-KIT/PDGFRα) Dual Inhibitor for the Treatment of Imatinib-Resistant Gastrointestinal Stromal Tumors (GISTs)

Stem cell factor receptor (c-KIT) and platelet derived growth factor receptor alpha (PDGFRα) kinases play an important role in gastrointestinal stromal tumors (GISTs). Here, we have discovered an c-KIT/PDGFRα dual inhibitor, compound 31, with single-digit nanomolar potency against c-KIT and PDGFRα. Compared to Imatinib (1), 31 showed better antiproliferative efficacy against various TEL-c-KIT/PDGFRα-BaF3 isogenic cells, including three 1-resistant BaF3 cell lines, as well as against GIST-T1 and GIST-882 cell lines. Furthermore, compound 31 showed a good KinomeScan selectivity (468 kinases) (S score (1) = 0.01 at 1 μM concentration), good metabolic stability in liver microsomes, and no hERG inhibitory activity. It was worth noting that 31 inhibited GIST-T1 tumor growth (TGI = 81.5%) and even the BaF3-TEL-cKIT-T670I tumor progression (TGI = 41.9%, 1-resistant GISTs) at a dosage of 100 mg/kg/day without exhibiting apparent toxicity.

Combination of 4-anilinoquinazoline, arylurea and tertiary amine moiety to discover novel anticancer agents

In present study, 4-anilinoquinazolines scaffold, arylurea and tertiary amine moiety were combined to design, synthesize gefitinib analogs and discover novel anticancer agents. A series of 4-anilinoquinazoline derivatives (1, 2, 3 and 4) bearing arylurea and tertiary amine moiety at its 6-position were synthesized. Their antiproliferative activities in vitro were evaluated via MTT assay against A431 cell and A549 cell. The SAR of the title compounds was discussed. The compounds 2d, 2i and 2j with potent antiproliferative activities were evaluated their inhibitory activity against EGFR-TK. Compound 2j displayed potent inhibitory activity against EGFR-TK. In addition, compound 2j, at 50 mg/kg, can completely inhibit cancer growth in established nude mouse A549 xenograft model in vivo. These results suggest that the 4-anilinoquinazoline derivatives bearing diarylurea and tertiary amino moiety at its 6-position can serve as anticancer agents and EGFR inhibitors.

TGF-beta SIGNAL TRANSDUCTION INHIBITOR

The present invention provides a compound represented by the following formula (I) or a physiologically acceptable salt thereof, and use thereof for the prophylaxis or treatment of TGF-β-related diseases: wherein Y is a hydrogen atom and the like; R2 is and the like; R3 is —NR8—R9— and the like; R4, R5, R6 and R7 are the same or different and each is a hydrogen atom and the like; and X is and the like.