N,N-Diethylaniline hydrochloride

• CAS: 5882-45-1
• Catalog Number: ACM5882451
• Category: Main Products
• Molecular Weight: 185.69
• Molecular Formula: C₁₀H₁₆ClN
• Synonyms: n,n-diethyl-anilinhydrochloride;n,n-diethylaniliniumchloride;n,n-diethyl-benzenaminhydrochloride;DIETHYLPHENYLAMINE HYDROCHLORIDE;BENZENAMINE, N,N-DIETHYL-, HYDROCHLORIDE;N,N-Diethylphenylamine hydrochloride;N,N-DIETHYLANILINE HYDROCHLORIDE;N,N-diethylbe
• IUPAC Name: N,N-diethylaniline;hydrochloride
• SMILES: CCN(CC)C1=CC=CC=C1.Cl
• InChI Key: PQCWTNQXCXUEAO-UHFFFAOYSA-N
• Boiling Point: 213.5ºC at 760mmHg
• Flash Point: 97.8ºC
• Appearance: White crystalline powder or mass
• EC Number: 227-556-9
• Exact Mass: 185.09700

Case Study

Immunotoxicity Assessment of N,N-Diethylaniline in CBA/N Mice

Li, Qing, et al. Toxicology, 2000, 150(1-3), 179-189.

The research examined how N,N-diethylaniline affects immune function in CBA/N mice while this synthetic intermediate is utilized in the production of dyes and organic materials. The researchers chose N,N-diethylaniline hydrochloride for analysis because N,N-diethylaniline is insoluble in water.
Experimental Design
The study divided mice into four groups for subcutaneous injections of N,N-diethylaniline at doses of 0, 100, 200, and 400 mg/kg. Measured body weight and spleen weight and assessed splenocyte count, natural killer (NK) and cytotoxic T lymphocyte (CTL) activity along with lymphocyte proliferation stimulated by Con A/LPS on days 3 and 7. The phenotypes of splenocytes were measured using flow cytometry to identify B cells along with total T cells and CD4+/CD8+ T cells as well as NK cells macrophages and nucleated erythrocytes.
Key Results
NK and CTL activity in the spleen showed dose-dependent suppression in groups exposed to the treatment while spontaneous lymphocyte proliferation increased at doses of 200 and 400 mg/kg. Mice that underwent treatment showed substantial increases in spleen weight and splenocyte counts, which were accompanied by higher amounts of macrophages and nucleated erythrocytes as well as B cells in their spleens. The administration of N,N-diethylaniline resulted in no changes to LPS/Con A-induced lymphocyte proliferation rates or NK/T cell proportions and did not affect body weight. These findings suggest selective inhibition of NK and CTL functions, independent of changes in cell numbers, implicating functional impairment rather than quantitative cell loss.

N,N-Diethylaniline Hydrochloride Used in the Synthesis of N,N-Diethylaniline Borane

Mahale, Rajendra D., et al. Organic Process Research & Development, 2012, 16(4), 710-713.

This study detailed the synthesis of N,N-diethylaniline borane (DEANB) utilizing N,N-diethylaniline hydrochloride (10) and sodium borohydride (NaBH4) as starting materials, along with its subsequent in situ application in the asymmetric reduction of prochiral ketones.
Optimization of conditions for the synthesis of DEANB
The initial method involved introducing solid 10 into a suspension of sodium borohydride in dimethoxyethane, followed by the asymmetric reduction of the prochiral ketone within the same reaction vessel (See Table 1, entry 1). However, researchers recognized that this approach posed safety risks at larger scales due to the release of flammable hydrogen gas. Thus, it was modified the procedure by dissolving 10 in dichloromethane and then introducing this solution to the sodium borohydride suspension gradually at room temperature, while keeping other reaction conditions unchanged (See Table 1, entry 2).
Attempts to substitute dimethoxyethane with dichloromethane and tetrahydrofuran (THF) in the reaction did not yield any conversion (See Table 1, entries 3-4). Additionally, altering the order of addition by placing 11 before 10 resulted in an incomplete reaction and reduced enantioselectivity (80%) (See Table 1, entry 5). It was determined that maintaining an equimolar ratio of 10 and sodium borohydride was crucial for achieving improved enantioselectivity (See Table 1, entries 6-8).

A report on the in vitro induction of blood lymphocytes by N,N-diethylaniline hydrochloride

Li, Qing, and Masayasu Minami. Mutation Research/Genetic Toxicology and Environmental Mutagenesis 395.2-3 (1997): 151-157.

N,N-Diethylaniline is a reagent used in organic synthesis and is an important intermediate in dye manufacturing. To assess its genotoxicity, its ability to induce sister chromatid exchange (SCE) in human lymphocytes was examined. In the absence and presence of a mixture of N,N-diethylaniline and S-9, N,N-diethylaniline significantly increased the frequency of SCEs. These results indicate that N,N-diethylaniline possesses genotoxicity.
The non-specific cytotoxicity of a mixture of N,N-diethylaniline hydrochloride and S-9 was examined using human lymphocytes to determine the optimal concentration for in vitro SCE testing, where N,N-diethylaniline does not inhibit lymphocyte proliferation but can induce SCEs. Lymphocytes were isolated from the peripheral blood of four healthy subjects and then seeded into triplicate of RPMI 1640 containing 10% FBS, 5^10-5 M 2-ME and 3% PHA-M, and incubated at 37°C in 5% CO2 for 24 hours.

One-pot synthesis of oxazol-5(4H)-one using N,N-diethylaniline hydrochloride

Fujita, Hikaru, and Munetaka Kunishima. Chemical and Pharmaceutical Bulletin 60.7 (2012): 907-912.

A one-pot synthesis method for oxazol-5(4H)-one was developed, which can be used for the activation of carboxylic acids in aqueous solvents. Oxazolinones are prepared by N-acylation of an amino acid with a carboxylic acid, followed by cyclization dehydration of the resulting N-acyl amino acid by the addition of N,N-diethylaniline hydrochloride. This process is simplified and readily implemented because both reactions are efficiently carried out in aqueous solvents using the same coupling agent, DMT-MM.
DMT-MM was added to a solution of carboxylic acid and N-methylmorpholine acetone/H₂O at room temperature. After stirring for 15-30 min, a solution of amino acid and sodium hydroxide in water was added, and the mixture was stirred at room temperature. After the reaction was complete, dichloromethane, N,N-diethylaniline hydrochloride, and DMT-MM were added sequentially, and the mixture was stirred at room temperature for 2-8 h. The reaction mixture was poured into an organic solvent (hexane, EtOAc, or hexane/EtOAc), and washed twice with water, twice with 1% HCl, water, and a saturated NaCl aqueous solution. The organic layer was dried over MgSO₄, filtered, and the solvent was evaporated under reduced pressure to give oxazoline.