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Chicago sky blue 6B is a synthetic dye with the molecular formula C16H10N2O2 and a molecular weight of 270.27. Its chemical structure consists of a benzene ring, a pyridine ring, and an azo group, which gives it high stability, as well as good light and climate resistance. The physical state is usually a dark blue powder with high purity. Its particle size is usually in the micrometer range and can be screened through a sieve. Its density is relatively high, about 1.4-1.5g/cm ³, Insoluble in water, but soluble in organic solvents. Its chemical properties make it widely applicable in multiple fields. It can be used for dyeing and printing materials such as ink, coatings, plastics, rubber, paper, and textiles.
Due to its structural characteristics, it also has good acid and alkali resistance and can be used in solutions with different pH values.It also has good heat resistance and light resistance, and can maintain color stability in high temperature and strong light environments. It also has low sublimation and good migration resistance, and can maintain bright colors for a long time. Can be used in the laboratory. It is more than 99% pure material obtained through our organic chemistry technology.
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Chemical Formula |
C34H29N6NaO16S4 |
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Exact Mass |
928.86 |
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Molecular Weight |
900 |
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Addition information of chemical compound: Storage conditions Room Temp, Color index 24410, Form Powder, Water solubility Soluble in water (1 mg/ml)., Stability Stable. Probably combustible. Incompatible with strong oxidizing agents.
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Chicago sky blue 6B is a synthetic dye with a molecular weight of 928.86. It appears as a blue-green or blue powder and is easily soluble in water to form a bright blue solution. It turns blue green when diluted with concentrated sulfuric acid and red purple when diluted with concentrated nitric acid. Its unique chemical properties make it occupy an important position in traditional industries, biological sciences, and cutting-edge research fields.
Traditional industrial field: Core raw materials for dyeing and coloring
1. Dyeing of cellulose fabrics
It is a classic dye for dyeing cellulose fabrics such as cotton, linen, and viscose. The dyeing principle is based on the hydrogen bonding and van der Waals forces between dye molecules and cellulose fibers, forming stable physical adsorption. At 60-80 ℃, the affinity of dyes for cellulose reaches its peak, with excellent absorption and outstanding discharge properties (i.e. the ability to remove some dyes through chemical treatment to form patterns), making it suitable for printing processes with complex patterns. In addition, it can also be used for dyeing silk, nylon, and viscose/nylon blended fabrics, expanding its application range.
2. Paper and ink manufacturing
In the paper industry, as a coloring agent, it can give the paper a uniform blue tone and enhance the visual effect. Its water solubility makes it easy to mix with pulp, and it has high color fastness and is not easily faded. In the field of ink, its bright blue solution is used to produce blue ink, which is widely used in writing, printing, and artistic creation.
Biological Science Field: Multivariate Tools from Tissue Staining to Cell Labeling
1. Biological tissue staining
Plays an important role in biological staining, especially suitable for staining neural tissue, connective tissue, and organelles. Pontamine sky blue blue background can clearly highlight the details of organizational structure, making it easy to observe under a microscope. For example, in neuroscience research, it is used to label neurons and nerve fibers in rat brain slices, assisting in electrophysiological recording and morphological analysis.
2. Immunofluorescence immunohistochemistry background counterstaining
In immunofluorescence experiments, as a background counterstain, it can effectively reduce tissue spontaneous fluorescence and enhance the contrast of target signals. Its structure is related to glutamate and it is an effective and competitive VGLUT (vesicular glutamate transporter) inhibitor, but it does not affect the function of plasma membrane transporters.This characteristic makes it uniquely valuable in neurotransmitter transport research.
3. Electrode fillers for electrophysiological recording
Used as a filler for glass transfer electrodes in electrophysiological recordings of rat brain slices. Its blue solution can visually display the electrode position, facilitating precise positioning and operation, while avoiding chemical damage to the tissue.
Research Experiment Field: Auxiliary Reagents from Biochemical Analysis to Drug Development
1. Biochemical research reagents
Widely used in biochemical experiments, such as:
Enzyme activity assay: As an indicator for enzymatic reactions, enzyme activity is quantitatively analyzed through color changes.
Protein precipitation: Its sulfate form can selectively precipitate proteins for protein purification and separation.
Nucleic acid research: As a staining agent for nucleic acid electrophoresis, it assists in visualizing DNA/RNA bands.
2. Spectral analysis standards
In UV visible spectrophotometry, the stable absorption peak of chicago sky blue 6B (such as λ max ≈ 620nm) makes it a standard substance for calibrating instruments. In addition, the complex formed with lanthanide ions can be used for photometric determination of antibiotic residues in human serum and urine samples, with high sensitivity at the Danak level.
3. Cell culture and labeling
In cell biology research, it is used to label cell membranes or organelles and observe dynamic changes in cells through fluorescence microscopy. Its low toxicity makes it suitable for live cell imaging and can be combined with other fluorescent dyes to achieve multi parameter analysis.
Frontier research fields: exploration from neuroprotection to disease models
1. Development of neuroprotective agents
Research has shown that it can inhibit amyloid beta induced neuronal toxicity and protect PC12 cells from apoptosis. Its mechanism may be related to clearing reactive oxygen species (ROS) and stabilizing mitochondrial membrane potential, providing candidate molecules for the development of Alzheimer's disease treatment drugs.
2. Prion research tools
It is the first small molecule PrP ligand capable of inhibiting A β binding, which inhibits A β - induced neurotoxicity by blocking the interaction between A β and PrP. This discovery provides new ideas for the mechanism research of prion diseases and Alzheimer's disease.
3. Construction of disease models
In animal models, it is used to induce specific disease phenotypes. For example, it can cause thyroid dysfunction and blood glucose changes in mice, providing a tool for metabolic disease research. In addition, its carcinogenicity and mutagenicity assessment (such as its impact on embryonic development) provides data support for toxicological studies.
Special application areas: from industrial testing to safety protection
1. Testing of industrial chemicals
As an indicator, chicago sky blue 6B is used to detect heavy metal ions (such as Pb ² ⁺, Cd ² ⁺) in industrial wastewater, with a detection limit as low as ppb. The color change of the complex formed with metal ions is obvious, which facilitates rapid qualitative analysis.
2. Laboratory safety and protection
Although Pontidine Blue is widely used in scientific research, its toxicity cannot be ignored.
According to toxicological data, intravenous ingestion of 2260 mg/kg in rodents can cause stomach discomfort and lung abnormalities, while intraperitoneal ingestion of 200 mg/kg has an impact on embryonic development. Therefore, experimental operations need to be carried out in a fume hood, wearing protective gloves and goggles, and stored away from sources of fire and oxidants.
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It is an organic pigment with special physical properties, and the following are two common synthesis methods:
Method 1:
Step 1:
Add 250g of 3-aminopyridine, 135g of sodium carbonate, 400mL of water, and 100mL of methanol to a three necked bottle, stir and heat until reflux occurs. At this time, 3-aminopyridine exists in the form of sodium salt, which is beneficial for subsequent nucleophilic substitution reactions.
Chemical equation:
3-aminopyridine reacts with sodium carbonate to obtain 3-aminopyridine sodium salt: (CH3) 2NH2C5H4NH2 (aq) + Na2CO3 (s) → (CH3)2NH2C5H4NH2Na (aq) + NaHCO3 (aq)
Step 2:
Add 200mL of bromomethane dropwise and maintain the reaction temperature at around 90 ° C. After about 3 hours of dripping, bromomethane acts as a nucleophilic reagent to attack the nucleophilic center of 3-aminopyridine sodium salt and carry out nucleophilic substitution reaction.
Chemical equation:
(CH3)2NH2C5H4NH2Na (aq) + CH3Br (aq) → (CH3)2NH2C5H4NBr (aq) + NaBr (aq) + H2O (l)
Step 3:
Reflux for another 2 hours to allow the reaction to proceed fully. Cool the reaction solution to room temperature, filter to remove the generated sodium bromide, transfer the filtrate to a separating funnel, separate the organic phase, wash with 5% sodium hydroxide solution to neutral, and then wash with sodium chloride solution. The organic phase is the crude product.
Chemical equation:
CH3Br (aq) + NaOH (aq) → CH3ONa (aq) + NaBr (aq) + H2O (l)
Step 4:
The crude product was subjected to vacuum distillation, and a fraction of 135 ℃/0.4kPa was collected to obtain approximately 80g of light yellow oily substance with a yield of 68.5%. This step is to purify the product and remove other unreacted substances and solvents.
Chemical equation:
(CH3)2NH2C5H4NBr (aq) → (CH3)2NH2C5H4NBr (l) + HBr (g)
(CH3)2NH2C5H4NBr (l) → (CH3)2NH2C5H4NBr (g) + HBr (g)
Method 2:
Step 1:
Add 20g of 3-aminopyridine or 6-aminopyridine, 2g of catalyst, 200mL of methanol, and 100mL of water to a 250mL three necked bottle, and heat to reflux. In this step, 3-aminopyridine or 6-aminopyridine reacts with methanol and water under the action of a catalyst to produce intermediate products such as 3-methoxymethyl pyridine or 6-methoxymethyl pyridine.
Chemical equation:
3-Aminopyridine reacts with methanol and water to obtain 3-methoxymethyl pyridine:
(CH3)2NH2C5H4NH2 (aq) + CH3OH (aq) + H2O (l) → (CH3)2NHC5H4N (CH3)OH (aq)
6-Aminopyridine reacts with methanol and water to obtain 6-methoxymethyl pyridine:
C5H5N(CH3)2 (aq) + CH3OH (aq) + H2O (l) → C5H5N(CH3)CH2OH (aq)
Step 2:
Add 25g of formaldehyde dropwise and complete the dropwise addition within 4 hours. Formaldehyde, as another nucleophilic reagent, attacks the nucleophilic centers of 3-methoxymethyl pyridine or 6-methoxymethyl pyridine for nucleophilic substitution reactions.
Chemical equation:
(CH3)2NHC5H4N (CH3)OH (aq) + HCHO (aq) → (CH3)2NHC5H4N(CH3)CH2OH (aq) + H2O (l)
C5H5N(CH3)CH2OH (aq) + HCHO (aq) → C5H5N(CH3)CH2CH2OH (aq) + H2O (l)
Step 3:
After the formaldehyde is added dropwise, continue reflux for 1 hour to allow the reaction to proceed fully. After stopping the heating, cool the reaction solution to room temperature. Then transfer the reaction solution to a separating funnel, separate the organic phase, and wash with a dilute hydrochloric acid solution.
Step 4:
Distill the organic phase and collect the fraction at 130 ℃/0.4kPa to obtain approximately 15g of the chicago sky blue 6B with a yield of 78%. This step is also to purify the product and remove other unreacted substances and solvents. During the distillation process, these organic solvents will gradually be separated as the temperature increases.
I. Origins of Industrial Dye Development
Also known as pontamine sky blue and direct blue 1 (C.I.24410), this compound emerged amid the industrial boom of aniline dyes in Germany at the start of the 20th century, developed by the AGFA Aniline Works in Germany. At that time, the textile industry was in urgent demand for water-soluble direct blue dyes with excellent wash fastness. The research team utilized dianisidine as the diazo parent and Chicago acid as the coupling component to synthesize a bisazo blue dye via double diazotization-coupling reactions.
It was named pontamine sky blue for its clear sky-blue shade. Large-scale industrial production was realized around 1910, and the dye was launched into textile markets across Europe and America.
II. Expansion of Cross-Disciplinary Applications
In its early years, it was solely used for dyeing cotton and viscose fibers. In the mid-20th century, researchers discovered that its multiple sulfonate groups enable strong binding to proteins and nucleic acids, and it was gradually adopted as a counterstain in histopathology.
Breakthrough neuroscience studies in the 1990s verified its ability to competitively inhibit vesicular glutamate transporters, granting it dual functions as both a dye and a pharmacological probe.Continuous optimization of synthetic processes gave rise to high-purity reagent-grade variants. Nowadays, it is widely applied in immunofluorescence staining and inflammatory target screening, evolving from a conventional textile dye into a core laboratory reagent for life sciences, carrying forward a century-long lineage of research and practical utilization.
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