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2-Bromo-5-nitrobenzotrifluoride is an important fluorine-containing organic intermediate, with its structure featuring multiple key functional groups such as bromine atoms, nitro groups, and trifluoromethyl groups. These highly reactive groups make it highly valuable in fine chemicals, pharmaceuticals, and pesticide synthesis, especially as the introduction of the trifluoromethyl group can significantly alter the lipophilicity, metabolic stability, and biological activity of the parent molecule.
In drug development, it is often used as a key framework to construct more potent candidate drug molecules; in the field of materials science, it is a valuable building block for synthesizing special polymers or liquid crystal materials. However, this compound is unstable in nature and has certain toxicity and potential irritancy. Therefore, strict requirements for the operating environment and personnel protection must be met. It must be handled carefully by professionals in a well-ventilated environment to ensure experimental safety and synthesis efficiency.
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C.F |
C7H3BrF3NO2 |
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E.M |
269 |
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M.W |
270 |
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m/z |
269 (100.0%), 271 (97.3%), 270 (7.6%), 272 (7.4%) |
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E.A |
C, 31.14; H, 1.12; Br, 29.59; F, 21.11; N, 5.19; O, 11.85 |
Teniposide, recognized under the trade name VM-26, stands out as a semi-synthetic derivative of podophyllotoxin, renowned for its robust anti-tumor properties. Its primary mode of action involves the inhibition of topoisomerase II, an enzyme integral to DNA replication and repair processes. By targeting this enzyme, teniposide induces DNA strand breaks, effectively interrupting cell division and proliferation. This mechanism renders it highly effective in combating a diverse array of cancers, including but not limited to acute leukemias, lymphomas, and certain solid tumors.
The drug's ability to interfere with the fundamental processes of cancer cell growth makes it a valuable component in various chemotherapy regimens.Its efficacy is further enhanced when used in combination with other chemotherapeutic agents, allowing for a synergistic effect that improves treatment outcomes. Additionally, teniposide's capacity to penetrate the blood-brain barrier positions it as a critical option for treating central nervous system malignancies, where other therapies may be less effective.However, the use of teniposide is not without challenges.
It is associated with significant side effects, such as myelosuppression, which can lead to decreased blood cell counts, and gastrointestinal toxicities.
Close monitoring and supportive care are essential to manage these adverse effects and optimize patient outcomes.
Despite these challenges, teniposide remains a cornerstone in oncology, offering hope and therapeutic benefit to patients with various forms of cancer.
The steps for preparing dispersed blue 360 using 2-Bromo-5-nitrobenzotrifluoride are as follows:
Put 2-bromo-5-nitrothiazole, hydrazine hydrate and 2-Methyltetrahydrofuran into the reactor, stir and keep the temperature at 30-35 ℃ for more than 1h, and add methanol after the reaction. The mass ratio of 2-bromo-5-nitrothiazole to hydrazine hydrate is 1: (0.28-0.4), the mass ratio of 2-bromo-5-nitrothiazole to 2-Methyltetrahydrofuran is 1: (20-40), and the mass ratio of 2-bromo-5-nitrothiazole to methanol is 1: (30-40); After adding methanol, filter, wash the filter cake with methanol, and vacuum dry below 55 ℃ to obtain the solid product 2-hydrazino-5-nitrothiazole.
Put 2-hydrazin-5-nitrothiazole, 3-methyl-4-chloro-N, N-diethylaniline, triethylamine, Copper(I) bromide and butanol into the reactor, replace the reactor with nitrogen, close the reactor, stir and heat up to 60-64 ℃ for 2-2.5 h, and react. The mass ratio of 2-hydrazin-5-nitrothiazole to 3-methyl-4-chloro-N, N-diethylaniline is 1: (1.3-1.38).
And the mass ratio of 2-hydrazin-5-nitrothiazole to triethylamine is 1: (2-3), The mass ratio of 2-hydrazino-5-nitrothiazole to Copper(I) bromide is 1: (0.025-0.1), and the mass ratio of 2-hydrazino-5-nitrothiazole to butanol is 1: (5-10); After the reaction is completed, it is cooled to room temperature, filtered, and the filter cake is washed with a small amount of methanol. The solid product 2-[4-(diethylamino)-2-methylphenyl] hydrazine] -5-nitrothiazole is obtained by drying.
Put 2-[[4-(diethylamino)-2-methylphenyl] hydrazine]-5-nitrothiazole, solvent DMSO, catalyst NH4VO3/CuCl2/H2SO4 into the reactor, stir and heat it up to 80-85 ℃, add the oxidant Sodium perborate in about 1 hour, continue to heat it up to 120-125 ℃ after feeding, and conduct thermal insulation reaction for more than 4 hours.
The mass ratio of 2-[[4-(diethylamino) -2-methylphenyl] hydrazine]-5-nitrothiazole to DMSO is 1: (10-20), The mass ratio of 2-[4- (diethylamino)-2-methylphenyl] hydrazine] -5-nitrothiazole to NH4VO3 is 1: (0.025-0.05), the mass ratio of 2-[4-(diethylamino)-2-methylphenyl] hydrazine]-5-nitrothiazole to CuCl2 is 1: (0.2-0.25), and the mass ratio of 2-[4-(diethylamino)-2-methylphenyl] hydrazine] -5-nitrothiazole to H2SO4 is 1: (0.5-1), The mass ratio of 2-[[4-(diethylamino)-2-methylphenyl] hydrazine] -5-nitrothiazole to Sodium perborate is 1: (1.5-2).
After the reaction is completed, methanol is added dropwise for separation, and the mass ratio of 2-[4-(diethylamino)-2-methylphenyl] hydrazine]-5-nitrothiazole to methanol is 1: (30-60). The filter cake is filtered, washed with a small amount of water, and dried to obtain the target product dispersion blue 360.
in pharmaceutical synthesis
Synthetic anti-tumor drugs
Antitumor drugs are drugs used to treat tumor diseases, which have the effect of inhibiting the growth and spread of tumor cells. 2-Bromo-5-nitrobenzotrifluoride can serve as an important intermediate for the synthesis of anti-tumor drugs. For example, through specific chemical reactions, it can be converted into compounds with anti-tumor activity, such as tiniposide. These drugs are widely used in clinical practice.
Synthetic antibacterial drugs
Antibiotics are drugs used to treat bacterial infections and have the ability to kill or inhibit bacterial growth. It can also serve as an important intermediate for the synthesis of antibacterial drugs. For example, through specific chemical reactions, the substance can be converted into compounds with antibacterial activity, such as cephalosporins. These drugs are widely used in clinical treatment of a variety of bacterial infectious diseases.
Synthetic anti-inflammatory drugs
Anti inflammatory drugs are drugs used to treat inflammatory diseases and have the effect of inhibiting inflammatory reactions. It can also serve as an important intermediate for the synthesis of anti-inflammatory drugs. For example, through specific chemical reactions, it can be converted into compounds with anti-inflammatory activity, such as nonsteroidal anti-inflammatory drugs.
Synthesis of compounds with specific pharmacological activity
This compound has a wide range of applications in pharmaceutical synthesis. Through specific chemical reactions, it can be converted into compounds with specific pharmacological activities, antibacterial drugs, etc. These compounds can inhibit the growth and spread of tumor cells, kill or inhibit the growth of bacteria.
Synthetic dyes and pigments
It can also be widely used in the synthesis of industrial dyes and functional pigments. Through a series of specific chemical synthesis and structural modification reactions, it can be efficiently converted into dye or pigment molecules with unique color tones and stable physicochemical properties. The prepared dyes and pigments feature outstanding coloring performance, excellent color fastness and long-term storage stability, and are widely applicable in many downstream fields including textile dyeing and finishing, printing ink production, as well as industrial coating and paint manufacturing.
Synthetic flavor and essence
It can also be used as an important chemical intermediate for synthetic flavors and essences. Through targeted specific chemical reactions, it can be transformed into high-value compounds with unique aromatic flavors, which are further processed to synthesize refined flavors and essences. These spices and essences possess distinctive fragrance layers and pure taste characteristics, and can be widely applied in food, beverage, daily cosmetics and other related industrial fields.
2-Bromo-5-nitrobenzotrifluoride is a versatile organic compound belonging to the thiazole family, characterized by its unique heterocyclic structure that incorporates both sulfur and nitrogen atoms. This specific molecule features a bromine atom at the 2-position and a nitro (NO2) group at the 5-position of the thiazole ring. This particular substitution pattern imparts unique chemical properties and reactivity profiles to the compound, making it a valuable intermediate in the synthesis of various pharmaceuticals, agrochemicals, and functional materials.
Chemically, 2-Bromo-5-nitrothiazole exists as a stable, crystalline solid with a distinct melting point. Its molecular formula is C3HBrN2O2S.And it has a relatively high molecular weight due to the presence of bromine and the nitro group.
The introduction of the nitro group enhances its polarity and solubility in polar solvents, while the bromine atom serves as a good leaving group in substitution reactions, opening up a wide range of synthetic possibilities.In terms of applications, 2-Bromo-5-nitrothiazole finds utility as a key building block in organic synthesis. For instance, it can undergo cross-coupling reactions with aryl or alkenyl halides to form C-C bonds.
Thereby incorporating the thiazole moiety into more complex molecules. The nitro group can also be reduced to an amino group, providing access to amines that are further functionalized in the synthesis of pharmaceuticals.Additionally, its heterocyclic nature and electronic properties make it suitable for use in the development of luminescent materials, sensors, and electronic devices.Safety-wise, handling 2-Bromo-5-nitrothiazole requires appropriate precautions due to its potential toxicity and reactivity. It should be stored under controlled conditions, away from heat, sparks, and incompatible materials. Users should wear protective equipment and adhere to good laboratory practices to minimize exposure risks.
Adverse reactions
2-Bromo-5-nitrobenzotrifluride (CAS number: 367-67-9) is an aromatic compound containing bromine, nitro, and trifluoromethyl. The compound is stable at room temperature, but may decompose at high temperatures or during combustion to produce toxic gases such as hydrogen fluoride and hydrogen bromide.
As an organic synthesis intermediate, it is widely used in the synthesis of pharmaceuticals, pesticides, and dyes, and its toxicity is mainly attributed to the following structural features:
Nitro (- NO ₂): Nitroaromatic compounds are typically cytotoxic and can damage cell membranes and DNA by producing reactive oxygen species (ROS).Trifluoromethyl (- CF ∝): a strong electron withdrawing group that may enhance the lipophilicity of compounds, promote their penetration into biological membranes, and accumulate in adipose tissue.Bromine atom (- Br): Halogenated hydrocarbons may interfere with thyroid hormone synthesis or metabolism.
Animal experimental data-Oral ingestion: In animal experiments, nitroaromatic compounds may cause gastrointestinal irritation (such as vomiting and diarrhea), and in severe cases, can lead to liver cell necrosis (manifested as elevated serum transaminase) and renal tubular injury (elevated blood urea nitrogen).Skin contact: Yellow crystalline powder may cause contact dermatitis due to mechanical irritation or chemical corrosiveness, manifested as erythema, edema, or blisters.Inhalation exposure: Dust or vapor may irritate the respiratory mucosa, causing coughing, difficulty breathing, or pulmonary edema (when exposed to high concentrations).
Human exposure cases-Laboratory operations: Failure to wear protective equipment during weighing, dissolution, or reaction processes may result in skin or eye contact.
Industrial production: Equipment leakage during synthesis or purification processes may result in inhalation exposure.Suggestion: In the absence of specific LD ₅₀ data, the "precautionary principle" should be followed, and the compound should be considered to have moderate acute toxicity (GHS classification may be Category 4), and corresponding protective measures should be taken.
Carcinogenicity: There is currently no evidence to suggest that this compound has direct carcinogenicity, but nitro compounds may generate DNA adducts after metabolic activation, increasing the risk of gene mutations. The International Agency for Research on Cancer (IARC) has not included it in the list of carcinogens.Mutability: In vitro experiments (such as Ames test) lack data, but nitroaromatic compounds with similar structures (such as 2-nitrotrifluorotoluene) have shown weak mutagenicity in some experiments.Suggestion: Based on structure-activity relationship (SAR) analysis, it should be assumed that the compound has potential mutagenicity and follow the management regulations for genotoxic substances during operation.
FAQ
What is 2 Bromo 5 Fluorobenzotrifluoride used for?
2-Bromo-5-fluorobenzotrifluoride is widely utilized in research focused on: Pharmaceutical Development: This compound serves as a key intermediate in the synthesis of various pharmaceuticals, particularly in the development of anti-cancer agents and other therapeutic drugs.
What is 2 Bromo 5Fluorobenzotrifluoride?
2-Bromo5-Fluorobenzotrifluoride is a fluorinated aromatic halogenated compound, featuring a benzene ring substituted with bromine, fluorine and trifluoromethyl groups. Its special molecular structure endows it with excellent chemical stability and high reaction activity, making it a crucial fine chemical intermediate. It is widely used in organic synthesis, pharmaceutical molecule derivation, agrochemical development and material chemistry research, and can participate in coupling, substitution and cyclization reactions to construct complex fluorine-containing bioactive skeletons.
What are its storage requirements?
Seal and store in cool, dry and dark environment.
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