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Neutral red powder, also known as dimethyldiaminophenazine chloride or toluene red. It is an acid-base indicator, CAS 553-24-2, chemical formula (CH3) 2NC6H3N2C6H2CH3NH2HCl. Green crystalline powder, easily soluble in water and red in color, soluble in ethanol and yellow in color. Its solution is used to stain vacuoles in cells, which can identify cell viability. Live cells are stained red, while dead cells do not change color. This is opposite to Tai Pan Lan. Mainly used as an acid-base indicator, its pH color change range is 6.8-8.0, and its color ranges from red to orange yellow. Alkalinity indicators for water, nitrite, and urine; Hydrolysis indicator used for fat in organizational chemistry; Nissl staining of nerve cells. Co used with Jiana Green for in vitro staining of blood; Photometric determination of iodine ions; Preparation of neutral red test paper. In addition, it can also be used as an oxidation-reduction indicator, biological staining agent, neutral red dye, etc.
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Chemical Formula |
C15H17ClN4 |
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Exact Mass |
289 |
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Molecular Weight |
299 |
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m/z |
288 (100.0%), 289 (16.2%), 290 (32.0%), 291 |
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Elemental Analysis |
C, 62.39; H, 5.39; Cl, 12.28; N, 19.40 |
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Neutral red powder is a commonly used indicator used for acid-base titration and oxidation-reduction reactions. The process of producing neutral red from N, N-dimethyl-p-nitrosoaniline hydrochloride and toluene-2,4-diamine involves multiple reactions in organic synthesis. The following are the detailed steps and chemical equations:
Preparation of p-nitrosamine hydrochloride: Firstly, react p-nitrosamine with hydrochloric acid to generate p-nitrosamine hydrochloride.
Chemical equation:
H2N-C6H4-NO2 + HCl → H2N-C6H4-NO2 · HCl
N. N-Dimethylation: React the p-nitroaniline hydrochloride obtained in the previous step with N, N-dimethylformamide (DMF) and triethylamine (TEA) for N, N-dimethylation.
Chemical equation:
H2N-C6H4-NO2 · HCl + C3H7NO + C6H15N → N, N-dimethyl-p-nitrosoaniline hydrochloride
Preparation of toluene-2,4-diamine: Nitrate toluene under the catalysis of concentrated sulfuric acid to obtain p-nitrotoluene. Then, use reducing agents such as iron powder and hydrochloric acid to reduce the p-nitrotoluene obtained in the previous step to toluene-2,4-diamine.
Chemical equation:
C6H5-NO2 + H2 + Fe + HCl → C6H3(NH2)-2H
Coupling reaction: The N, N-dimethyl-p-nitrosoaniline hydrochloride obtained in step one is coupled with the toluene 2,4-diamine obtained in step two in an organic solvent (such as acetonitrile or THF) in the presence of a catalyst (such as TEA or Pyridine) for coupling reaction.
Chemical equation:
N. N-dimethyl-p-nitrosoaniline hydrochloride+C6H3 (NH2) -2H → C15H17ClN4+HCl+catalyst
Purification: Purify the reaction product through column chromatography or recrystallization to obtain a high-purity neutral red.
Add dimethylaniline to a 5 ℃ hydrochloric acid aqueous solution, stir to dissolve it, and then add sodium nitrite aqueous solution while stirring for reaction, with the temperature controlled at 5-10 ℃:
After stirring for 1 hour, filter and crystallize p-nitrosodimethylaniline hydrochloride. Wash with a small amount of water and set aside. Dissolve ferrous sulfate in hot water at 90 ℃, then add 2,4-diaminotoluene, stir thoroughly to dissolve, and slowly add the prepared p-nitrosodimethylaniline hydrochloride. Stir for reaction:
After 1 hour, add an appropriate amount of hydrochloric acid and filter. Inject hydrogen chloride gas into the filtrate, let it stand, wait for crystallization to complete, filter, and dry to obtain neutral red finished product.
Neutral red powder, chemical name 3-amino-7-dimethylamino-2-methylphenazine hydrochloride (or 3-amino-6-dimethylamino-2-methylphenazine hydrochloride), CAS number 553-24-2, molecular formula C ₁ H ₁ ClN ₄, molecular weight 288.78. It is a dark green crystalline powder that is easily soluble in water (red) and ethanol (yellow), with weak alkalinity and a pH range of 6.4-8.0 (red to yellow). As a classic phenazine dye, neutral red is widely used in chemical indicators, biological staining, industrial analysis and other fields. Its core applications can be summarized into the following categories:
One of the core functions of neutral red is to serve as an acid-base indicator, with a color change range covering neutral to weakly alkaline environments (pH 6.8-8.0), gradually transitioning from red to orange yellow. This characteristic makes it an ideal tool for monitoring the acidity and alkalinity of solutions in laboratories and industries:
Laboratory application: In titration analysis, it is commonly used to indicate the endpoint of weak or neutral solutions. For example, in the experiment of titrating hydrochloric acid with ammonia water, when the solution approaches neutrality, it turns from red to yellow, indicating the titration endpoint intuitively.
Industrial testing: can be used to detect the alkalinity of liquids such as water, urine, nitrite, etc. For example, in food processing, neutral red test strips are used to quickly determine the acidity or alkalinity of beverages, ensuring stable product quality.
Environmental monitoring: In wastewater treatment, it can indicate the degree of completion of neutralization reactions, help adjust pH to a safe range (such as 6-9), and avoid harm to the ecosystem.
Neutral red is an indispensable staining tool in biological research, and its weak alkaline properties enable it to selectively bind to acidic components within cells, thereby distinguishing live cells from dead cells or labeling specific organelles:
Cell viability testing
Neutral red staining is a classic method for detecting cell viability. The vacuoles of living cells are acidic and can absorb neutral red and dissociate cations, making the vacuoles appear cherry red; Dead cells are unable to maintain their vacuolar structure due to protoplast degeneration. Neutral red cations bind to negatively charged protoplasts and nuclei, causing the nuclei to stain instead of vacuoles. This principle is widely applied to:
Drug toxicity testing: Evaluate the killing effect of chemotherapy drugs on cancer cells through neutral red staining.
Organizational engineering: detecting the activity of stem cell cultures and optimizing cell expansion conditions.
Food Microbiology: Rapid identification of the survival status of microorganisms in food, such as the activity detection of lactic acid bacteria.
Organ and tissue staining
Lysosome staining: Neutral red can mark the acidic environment of lysosomes and is used to study autophagy processes or lysosome related diseases.
Golgi apparatus staining: Combined with Janus Green B, neutral red can enhance the contrast of the Golgi apparatus and facilitate microscopic observation.
Neuronal staining: Neutral red is used to label Nissl bodies of neurons, assisting in the study of neuronal damage mechanisms in neurodegenerative diseases such as Alzheimer's disease.
Fat hydrolysis indicator: In tissue chemistry, neutral red can indicate lipase activity and reflect the degree of fat breakdown through color changes.
Blood and Immunological Research
In vitro in vivo staining of blood: Neutral red combined with Jianna green can distinguish between red blood cells and white blood cells, or mark parasites (such as malaria parasites) in the blood.
Immunofluorescence staining: As a background staining agent, neutral red can enhance the contrast of fluorescent markers and improve the clarity of immunohistochemical images.
Industrial analysis: precise detection of specific ions and substances
The chemical properties of neutral red make it a multifunctional reagent in industrial analysis, particularly suitable for ion detection and substance quantification
1. Iodine ion photometric determination
Neutral red forms a colored complex with iodide ions (I ⁻), and its absorbance is proportional to the concentration of iodide ions. By using spectrophotometry, the iodine content in water samples or food can be quantitatively determined, such as monitoring the iodine concentration in salt iodization processes.
2. Metal ion detection
Neutral red can form colored ion complexes with metal ions such as mercury (Hg ² ⁺) and indium (In ³ ⁺), and is used for qualitative detection of metal ions in wastewater or ores.
For example, in electronic waste recycling, neutral red can quickly screen for materials containing indium.
3. Nitrite detection
Neutral red powder reacts with nitrite to produce orange red compounds, which can be measured for nitrite residues in food (such as cured meat) or environmental water samples using colorimetric methods to ensure compliance with safety standards (such as the EU limit of 0.5-3 mg/kg).
Clinical and pathological diagnosis: auxiliary disease detection and treatment
The application of neutral red in the medical field extends to clinical diagnosis and pathological research, providing visualization tools for disease detection:
1. Tumor diagnosis
The neutral red staining method is used to distinguish the activity and necrotic areas of tumor cells. For example, after surgical resection of the tumor, the cell activity of the edge tissue can be quickly evaluated through neutral red staining to guide subsequent treatment (such as whether to expand the resection range).
Infection detection
Neutral red can be used to mark the acidic metabolites of bacteria or fungi and assist in the diagnosis of infectious diseases. For example, in sputum samples, neutral red staining can distinguish the activity of Mycobacterium tuberculosis and improve diagnostic accuracy.
Cell therapy monitoring
In stem cell therapy, neutral red staining is used to evaluate the survival rate and proliferation ability of transplanted cells. For example, in corneal repair surgery, the engraftment of stem cells in the corneal stromal layer is monitored by neutral red staining.
Neutral red has become a classic reagent in biology and chemistry teaching due to its easy operation and low cost
Cell Biology Experiments
The neutral red staining method is widely used in teaching experiments to help students understand cell structure and function. For example, by observing onion epidermal cells stained with neutral red, students can intuitively understand the relationship between the acidic environment of vacuoles and cell activity.
microbiology teaching
In microbial cultivation experiments, neutral red is used to distinguish between live and dead bacteria, assisting students in mastering the method of measuring microbial growth curves.
Research on Chemical Indicators
Neutral red, as a model compound, is used to study the color changing mechanism and structure property relationship of phenazine dyes, providing theoretical basis for the development of new indicators.
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