1-Bromohexadecane CAS 112-82-3

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1-Bromohexadecane, also known as bromohexadecane in Chinese, is an important organic compound with extensive applications in the chemical industry. Presented as a colorless to light yellow transparent liquid. This clear appearance indicates that its molecular arrangement is relatively orderly and the impurity content is low. At room temperature, good fluidity indicates moderate intermolecular interactions, allowing the liquid to flow smoothly. The melting point is relatively low, generally between 16 and 18 ° C.

Melting point 16-18 ° C (lit.), Boiling point 190 ° C11 mm Hg (lit.), Density 0.999 g / ml at 25 ° C (lit.), Vapor density 10.6 (vs air), Vapor pressure < 1 mm Hg (20 ° C), Refractive index N20 / D 1.4609 (lit.), Flash point > 230 ° f, Storage conditions: insert atmosphere, room temperature, Solubility: diffcult to mix, Form: liquid after melting, Specific gravity 1.000 (20 / 4 ℃), Color: clear amber to brown black, Water solubility (insoluble), BRN 773989, Stability Incompatible with strong oxidizing agents.

This means that at slightly below room temperature, bromochexane will transition from solid to liquid. This property enables brominated hexadecane to maintain good fluidity in low-temperature environments, providing convenience for its application in cold regions. Insoluble in water, but easily soluble in organic solvents such as alcohols and ethers. The density is similar to that of water, but slightly heavier than water. Therefore, when mixed with water, it tends to sink to the bottom of the water. It can induce Gram positive bacterial membrane damage and inhibit the production of virulence factors such as metalloproteinases, which are involved in the pathogenesis of certain infections. Therefore, it can be used to treat microbial infections caused by Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Candida albicans. This discovery opens up new avenues for application in the field of antibacterial therapy.

The following are the detailed steps and corresponding chemical equations:

Step 1: Preparation and heating

Prepare reaction materials:

-Add hexadecanol (molecular formula: C16H34O, melting point approximately 48 ℃) into the reactor.
-Add an appropriate amount of red phosphorus (P4) as a catalyst and reducing agent for the bromination reaction. Red phosphorus reacts with hexadecanol to form some intermediate products, laying the foundation for the bromination reaction.
P4+6C16H34OH → Intermediate product

Heating and melting:

-Start heating the reaction mixture to melt hexadecanol and mix thoroughly with red phosphorus.

Step 2: Bromination reaction

Dropwise addition of bromine:

-When the reaction mixture reaches 100 ℃, slowly add bromine (Br ₂) dropwise. The addition of bromine is a crucial step in the bromination reaction, which undergoes a substitution reaction with hexadecanol, introducing bromine atoms to generate haloalkanes.
C16H34OH + Br2 → C16H33Br + HBr
Here, Br2 will gradually react with hexadecanol, replacing the hydrogen atom to produce 1-bromochexane (C16H33Br) and hydrogen bromide (HBr).

Temperature control:

-Control the reaction temperature within the range of 120-130 ℃, maintain appropriate reaction conditions to promote the progress of the reaction, and ensure efficient reaction without losing control.

Reaction time:

-After adding bromine dropwise, continue the reaction at a controlled temperature for about 6 hours to fully complete the bromination reaction.

Step 3: Remove hydrogen bromide and purify

Washing and layering:

-Cool the reaction mixture to below 50 ℃, then add a saturated aqueous solution of sodium chloride (NaCl). This step helps to separate the organic phase and the aqueous phase, while also helping to remove residual hydrogen bromide and other impurities.
C16H33Br + NaCl → C16H33Br + NaCl
Here, C16H33Br represents the organic phase of 1-bromochexane, and NaCl_ {aq} represents the sodium chloride solution in the aqueous phase.

Excluding hydrogen bromide:

-After the reaction is complete, continue heating to remove residual hydrogen bromide (HBr). This step is to ensure the purity and stability of the final product.
HBr → HBr

Wash with water to neutral-Wash the organic phase multiple times with water until the pH of the washing solution approaches neutrality. This step helps to thoroughly remove residual salts and other water-soluble impurities.

Through the above steps, you can obtain high-purity 1-bromohexane, which is a long-chain halogenated alkane suitable for various organic synthesis reactions. The entire synthesis process covers important reaction conditions and operational steps in organic chemistry, ensuring the purity and stability of the final product.

1-Bromohexadecane, also known as bromohexadecane, has attracted widespread attention in scientific research and pharmaceutical fields in recent years as an organic compound with unique chemical structure and properties. Especially in its application as an effective inhibitor of fatty acid synthase (FAS), it provides new strategies and ideas for the treatment of diseases related to fatty acid synthesis.

1. Inhibiting fatty acid synthesis

 

It synthase is a key enzyme responsible for catalyzing de novo synthesis of fatty acids in living organisms. It converts simple carbon sources (such as acetyl CoA) into long-chain fatty through a series of complex chemical reactions. Long chain fatty are not only an important component of cell membranes, but also participate in various biological processes such as energy storage and signal transduction. Therefore, inhibiting the activity of fatty acid synthase can effectively reduce the synthesis of fatty, which is of great significance for the treatment of obesity, diabetes, cardiovascular diseases and other diseases related to abnormal fatty synthesis.

2. Treating obesity

 

Obesity is a disease caused by excessive accumulation of fat in the body due to energy intake exceeding energy expenditure. Research has shown that the activity of fatt synthase in obese patients often increases abnormally, leading to excessive fatty synthesis. As an effective inhibitor of fatty synthase, it can reduce the synthesis of fatty and achieve weight loss by inhibiting the activity of the enzyme. In addition, due to its specific inhibitory effect on the synthesis of fatty, its side effects may be smaller and its safety may be higher compared to other weight loss drugs.

3. Improve diabetes symptoms

 

Diabetes is a metabolic disease characterized by hyperglycemia. Studies have shown that the activity of fatty synthase in diabetes patients is often abnormally elevated, leading to excessive fatty synthesis. Excess fatty acids will not only aggravate insulin resistance, but also damage pancreatic β cells through oxidative stress and other ways, further exacerbating the condition of diabetes. As an effective inhibitor of fatty synthase, it can improve insulin resistance and pancreatic beta cell function by inhibiting the synthesis of fatty, thus improving the symptoms of diabetes patients.

4. Reduce the risk of cardiovascular disease

 

Cardiovascular disease is a serious threat to human health, including coronary heart disease, myocardial infarction, stroke, etc. Research has shown that the activity of fatty synthase in cardiovascular disease patients often increases abnormally, leading to excessive fatty synthesis. Excess fatty will lead to abnormal blood lipids, atherosclerosis and other diseases, thus increasing the risk of cardiovascular disease. As an effective inhibitor of fatty synthase, it can reduce the level of blood lipids and atherosclerosis by inhibiting the synthesis of fatty, thus reducing the risk of cardiovascular disease.

5. Other potential applications

 

In addition to the above applications, as an effective inhibitor of fatty acid synthase, 1-bromohexadecane may also have potential application value in other fields. For example, in the field of tumor therapy, some tumor cells have abnormally active fatty synthesis pathways, and inhibiting the activity of fatty synthase can inhibit the growth and proliferation of tumor cells; In the field of neurological diseases, some neurological diseases are also related to abnormal fatty metabolism. By regulating the activity of fatty synthase, related symptoms can be improved.

Adverse reaction

This drug (chemical formula: C ₁₆ H ∝③ Br, CAS number: 112-82-3) is a long-chain brominated alkane commonly used in organic synthesis, surfactant preparation, and materials science. As a laboratory chemical and industrial intermediate, its safety is highly concerned. Although there is limited toxicological data available, a systematic analysis of its potential adverse reactions can be conducted based on its chemical properties (such as long-chain alkane structure, presence of bromine atoms) and the characteristics of similar compounds.

Oral exposure

Rat oral LD ₅₀>2000 mg/kg indicates that the acute toxicity of it is low under a single high-dose oral exposure. However, it should be noted that the LD ₅₀ value only reflects half of the lethal dose, and actual exposure may still cause non lethal acute symptoms.
Potential risks: Long chain alkane compounds may irritate the mucosa in the gastrointestinal tract due to their low solubility, leading to digestive system symptoms such as nausea, vomiting, and abdominal pain. The presence of bromine atoms may enhance lipid solubility and promote compound penetration through biological membranes, but there is currently no direct evidence to support its exacerbation of acute toxicity.

Skin contact

SDS often indicates "skin corrosion/irritation: no data" (such as supplier reports from Fisher Scientific, Thermo Fisher Scientific, etc.), but GHS classification (Angene, 2021) classifies it as skin irritation category 2 (H315), suggesting that it may cause skin irritation.
Potential risks: Long chain alkanes may cause dryness, erythema, or mild inflammation through physical actions such as peeling off skin oils. The lipophilicity of bromoalkanes may enhance skin permeability, but the specific mechanism needs further investigation.

Inhalation Exposure

In SDS, it is often labeled as "Inhalation Toxicity: No Data", but GHS classification (Angene, 2021) classifies it as respiratory irritation category 3 (H335), indicating that high concentration inhalation may cause respiratory irritation.
Potential risk:It is liquid at room temperature (melting point 17.3 ° C, boiling point 336 ° C), but heating or spray operation may produce volatile organic compounds (VOCs). Long chain alkanes can deposit in the respiratory tract, causing coughing, throat discomfort, or shortness of breath; Bromine atoms may exacerbate inflammatory reactions through oxidative stress.

Obtained by bromination of hexadecanol. Put hexadecanol (melting point 48 ℃) into a reaction pot, stir, heat, melt, and add red phosphorus. At 100 ℃, stir thoroughly while adding bromine dropwise. Control the temperature between 120-130 ℃ and complete the dropwise addition after about 6 hours. Continue the reaction and remove all hydrogen bromide. Cool to below 50 ℃, if saturated with sodium chloride aqueous solution, stir and wash, let stand for layering, separate the lower waste liquid, wash with water until neutral, distill, collect the fraction at 200-230 ℃ (2kPa) to obtain it.

Solubility

Organic solvent: Easily soluble in ether, extremely slightly soluble in methanol, indicating that its non-polar carbon chain (C₁₆H₃₃) dominates the solubility, while the polarity of the bromine atom (Br) is relatively weak.

Water solubility: Almost insoluble in water, consistent with the typical properties of long-chain alkyl bromides, due to the excessively long carbon chain making water molecules difficult to overcome its hydrophobic effect.

Safety and toxicity

Stinginess: Has irritancy to the skin (H315), eyes (H319), and respiratory tract (H335), and should be operated in a well-ventilated area and wear protective equipment.

Storage conditions: Should be sealed and stored in a cool, dry place, away from fire sources and strong oxidants to prevent decomposition or combustion.

Chemical structure and reactivity

Molecular formula: C₁₆H₃₃Br, composed of a straight-chain alkyl group of 16 carbon atoms and a terminal bromine atom.

Reaction site: The bromine atom acts as a leaving group and can participate in nucleophilic substitution reactions (such as reacting with sodium alcohol, amines to form ethers or amine derivatives); the α-carbon (the carbon adjacent to the bromine) may be activated due to the induction effect, but the stability of the long-chain alkyl group is higher, and the reactivity is lower than that of short-chain brominated alkanes.

Stability: Stable at room temperature, but avoid strong oxidants (such as potassium permanganate, concentrated nitric acid) to prevent the bromine atom from being oxidized to bromate or causing carbon chain breakage.

Refractive index and optical properties

The refractive index (n²⁰/D) is 1.461. This value reflects the arrangement of carbon chains and the electronic effects of bromine atoms in the molecule, and is valuable for purity identification and structural analysis.

Thermodynamic properties

Melting enthalpy (ΔvapH): Partial data is 71.90 kJ/mol (Joback calculation value), reflecting the energy required to break the intermolecular forces (van der Waals forces) during melting.

Critical properties: The critical temperature and pressure have not been determined, but the critical temperature of long-chain alkanes is usually high, and it requires high-pressure conditions to liquefy.

Overall, 1-Bromohexadecane combines stable physical properties and moderate reactivity, making it a highly practical intermediate in organic synthesis. Its low melting point and good liquidity at room temperature allow for convenient operation in industrial production and laboratory preparation. As a typical long-chain alkyl halide, it serves as a key raw material for the preparation of surfactants, phase transfer catalysts, and various organic derivatives. With reliable chemical stability and easy processing characteristics, it continues to play an essential role in fine chemical synthesis, material modification, and daily chemical production.

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