1,2,4,5-Benzenetetramine Tetrahydrochloride

• CAS: 4506-66-5
• Catalog Number: ACM4506665-4
• Category: Main Products
• Molecular Weight: 284.01
• Molecular Formula: C6H2(NH2)4·4HCl
• Synonyms: 1,2,4,5-Tetraaminobenzene tetrahydrochloride
• IUPAC Name: benzene-1,2,4,5-tetramine;tetrahydrochloride
• InChI: 1S/C6H10N4.4ClH/c7-3-1-4(8)6(10)2-5(3)9;;;;/h1-2H,7-10H2;4*1H
• InChI Key: BZDGCIJWPWHAOF-UHFFFAOYSA-N
• Melting Point: ≥300 °C (lit.)
• Appearance: dark gray solid
• Application: This product is suitable for scientific research.
• Assay: ≥95%; ≥95.0% (AT)
• Complexity: 90.3
• CompoundIs Canonicalized: Yes
• Covalently-Bonded Unit Count: 5
• Defined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• EC Number: 224-822-6
• Exact Mass: 283.994307g/mol
• Features And Benefits: 1. High quality products; 2. Fast delivery; 3. Additional products can be ordered, please contact us for details
• Formal Charge: 0
• Heavy Atom Count: 14
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 8
• Isotope Atom Count: 0
• MDL Number: MFCD00012970
• Monoisotopic Mass: 281.997257g/mol
• NACRES: NA.23
• PubChem ID: 24858402
• Quality Level: 100
• Rotatable Bond Count: 0
• Topological Polar Surface Area: 104Ų
• Undefined Atom Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0

Case Study

Enhancing Lithium Metal Battery Performance with 1,2,4,5-Benzenetetramine Tetrahydrochloride Additive

Lin, Zhihua, et al. Advanced Electronic Materials 10.4 (2024): 2300772.

Achieving highly stable lithium metal batteries (LMBs) requires a high-quality, inorganic-rich Solid Electrolyte Interphase (SEI). This case study examined the application of 1,2,4,5-Benzenetetramine Tetrahydrochloride (BHCL) as a novel, dual-function electrolyte additive designed to construct a LiCl-rich inorganic SEI layer, thereby improving lithium metal anode stability and overall battery performance.
Mechanism:
BHCL's structure enables synergistic effects: on one hand, BHCL's four high-donor-number amines have strong complexation affinity with Li+, which can bring BHCL near the Li metal surface; on the other hand, BHCL's phenyl group is electron-withdrawing, which will reduce its LUMO energy and thus increase the solvent stability; furthermore, free chloride ions in BHCL are incorporated into the solvation sheath, leading to the formation of a rigid, flat, and dense LiCl-rich SEI layer upon its decomposition.
Key Results:
Experimental results indicated the proposed theory and the positive effect of BHCL on LMB performance. Li||Li symmetric cells cycled for more than 2500 hours with ≈45 mV overpotential at 1 mA cm-2; Li||Cu cells delivered a high coulombic efficiency (CE) of 98.1% after 100 cycles at 0.5 mA cm-2; and the Li||LFP full cell also showed a significantly enhanced cycling stability and a reduced polarization.

Preclinical Assessment of Y15 (1,2,4,5-Benzenetetramine Tetrahydrochloride) as a FAK Inhibitor

Golubovskaya, Vita, et al. Archives of toxicology 89 (2015): 1095-1101.

The case study is a preclinical characterization of Y15 (1,2,4,5-benzenetetramine tetrahydrochloride), a selective and potent FAK inhibitor with antitumor activity for its in vivo pharmacokinetics, metabolic stability, and toxicity. The primary preclinical studies were carried out in mice.
Key Findings:
· Pharmacokinetics: Rapid absorption of Y15 was observed after IP administration (30 mg/kg). maximum plasma concentration (C_max) is reached within 4.8 minutes.
· Metabolism: Mouse and human liver microsomes were used for metabolic stability studies. Y15 demonstrated rapid metabolic turnover. The observed half-life (t_1/2) was 6.9 minutes in mouse liver microsomes and 11.6 minutes in human liver microsomes.
· Toxicity & Tolerability: Single-dose MTD (po) = 200 mg/kg. Multiple-dose MTD (po) = 100 mg/kg/day for 7 days. No mortality or statistically significant reduction in body weight was seen at 30 mg/kg (ip) for 28 days and 100 mg/kg (po) for 7 days. No drug-related clinically significant changes were seen in clinical chemistry, hematology, or histopathology of major organs at these doses and durations.
· This work established that 1,2,4,5-benzenetetramine tetrahydrochloride possesses a favorable initial safety and pharmacokinetic profile. Its rapid absorption and metabolism, combined with a well-tolerated dose range without significant toxicological findings.

Pharmacokinetic Study of the FAK Inhibitor Y15 (1,2,4,5-phenyltetramine tetrahydrochloride)

Golubovskaya, Vita, et al. Archives of toxicology 89.7 (2015): 1095-1101.

Y15 (1,2,4,5-phenyltetramine tetrahydrochloride) is a potent and specific inhibitor of focal adhesion kinase (FAK), inhibiting its autophosphorylation activity, reducing cancer cell viability, and blocking tumor growth. The pharmacokinetics of Y15 in mouse plasma, its metabolic stability in mouse and human liver microsomes, and its toxicity in mice were analyzed. Mouse pharmacokinetic studies demonstrated that following intraperitoneal administration of 30 mg/kg, Y15 was rapidly absorbed in mice, reaching maximum plasma concentrations within 4.8 minutes. Y15 was rapidly metabolized in mouse and human liver microsomes, with half-lives of t = 6.9 and 11.6 minutes, respectively. In a 7-day oral study, the maximum tolerated dose of Y15 was 200 mg/kg after a single dose, and 100 mg/kg after repeated administration. Y15 did not result in any statistically significant differences in mortality or body weight at 30 mg/kg administered intraperitoneally (IP) or 100 mg/kg administered orally (PO) during the 28-day study.
CD-1 mice were dosed with Y15 at 30 mg/kg or 100 mg/kg via intraperitoneal (IP) or oral (PO) administration, respectively. At the designated time points, animals were euthanized, and blood was collected by cardiac puncture and stored in K2eDTA tubes. Plasma was isolated by centrifuging the blood at 6000 rpm for 5 minutes to pellet the cells. The supernatant was stored at -80°C until analysis.

1,2,4,5-Benzenetetramine tetrahydrochloride as a battery additive

Lin, Zhihua, et al. Advanced Electronic Materials 10.4 (2024): 2300772.

Strategies for achieving highly stable lithium metal batteries (LMBs) have been extensively explored. A highly amine-rich 1,2,4,5-benzenetetramine tetrahydrochloride (BHCL) was developed as a bifunctional electrolyte additive for LMBs. The high donor number of amine groups increases lithium affinity, while the strongly inductive phenyl groups prevent solvent decomposition. Free chloride ions replace anions, mediating the formation of a rigid inorganic LiCl-rich SEI layer. This study provides a promising design principle for multifunctional electrolyte additives.
Lithium symmetric cells were fabricated and tested to determine the optimal amount of 1,2,4,5-benzenetetramine tetrahydrochloride (BHCL) as an electrolyte additive under various current capacity conditions. As little as 0.5 wt% BHCL in the electrolyte significantly improved cycling stability and stabilized hysteresis voltage. When the BHCL additive content increased to 2 wt%, the overpotential began to increase and the electrolyte viscosity also increased significantly (Figure S8, Supporting Information). The optimal content of BHCL additive was set to 0.5 wt%.

The synthesis of carbon dots using 1,2,4,5-benzenetetramine tetrahydrochloride as a carbon source

Zhao, Dan, et al. RSC advances 9.51 (2019): 29533-29540.

The synthesis of long-wavelength carbon dots (CDs), especially those that emit red light, has been a focus of research, and the carbon source is crucial in this process. Red-emitting CDs (CD-tetra) were synthesized via a one-step solvothermal method using 1,2,4,5-benzenetetramine tetrahydrochloride as a novel carbon source and ethanol as a solvent. The CDs exhibited a quantum yield (QY) as high as 30.2%. The CDs exhibited significant variation in particle size and elemental composition. Under optimal conditions, a linear relationship was established between the decrease in CD-tetra fluorescence intensity and MB concentration in the range of 0.05-9.5 mM. The limit of detection (LOD) was 10 nM, demonstrating a promising approach for detecting MB.
CDs were synthesized using a one-step solvothermal method. The synthesis method is as follows: 1,2,4,5-benzenetetramine tetrahydrochloride was dissolved in ethanol and stirred for 10 minutes under nitrogen. The mixture was then transferred to a stainless steel-lined autoclave and maintained at 170 °C for 5.5 h. Subsequently, the reaction solution was cooled.

Synthesis of a π-conjugated microporous polymer from 1,2,4,5-benzenetetramine tetrahydrochloride

Briega-Martos, Valentín, et al. ACS Catalysis 7.2 (2017): 1015-1024.

To produce hydrogen peroxide in small electrochemical devices, a selective catalyst for the oxygen reduction reaction (ORR) is required to reach the desired species. This paper reports the synthesis, characterization, ORR electrochemical behavior, and reaction mechanism of an aza-fused π-conjugated microporous polymer with high selectivity for hydrogen peroxide. The polymer was synthesized by the condensation polymerization of 1,2,4,5-benzenetetramine tetrahydrochloride and triquinoline octahydrate. A cobalt-modified version of the material was also prepared by a simple post-synthesis treatment with a Co(II) salt. The characterization of the material is consistent with the formation of a conductive, robust, porous, covalently laminar polyaza structure.
532.5 mg (1.875 mmol) of 1,2,4,5-benzenetetramine tetrahydrochloride was dissolved in 15 mL of anhydrous DMF, and 390 mg (1.25 mmol) of triquinoline octahydrate was dissolved in 5 mL of anhydrous DMF. The mixture was then refluxed under argon for 48 hours. The solid was purified by hot extraction with methanol using Soxhlet for 24 hours. The resulting solid was dried under vacuum at 150°C for 24 hours. The yield was 304.6 mg (91%). TGA analysis indicated a mass loss of approximately 7% between 20 and 250°C, which was attributed to solvent trapped in the pores. Chemical decomposition of the material began at 250°C.

Custom Q&A

What is the product name of the compound with cas number 4506-66-5?

The product name is 1,2,4,5-Benzenetetramine Tetrahydrochloride.

What is the IUPAC name of the compound?

The IUPAC name is benzene-1,2,4,5-tetramine tetrahydrochloride.

What is the molecular weight of this compound?

The molecular weight is 284.01.

What is the appearance of 1,2,4,5-Benzenetetramine Tetrahydrochloride?

The appearance is a dark gray solid.

What is the purity of this compound?

The purity is ≥95%.

What category does this compound fall under?

It falls under CHN Containing Functional Groups category.

What are the synonyms for 1,2,4,5-Benzenetetramine Tetrahydrochloride?

The synonyms are 1,2,4,5-Tetraaminobenzene tetrahydrochloride.

What is the melting point of this compound?

The melting point is ≥300°C.

What is the molecular formula of this compound?

The molecular formula is C6H2(NH2)4·4HCl.

What is the EC number of this compound?

The EC Number is 224-822-6.