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4-Amino-1-butanol(N-ABU(4)-OL) is an organic compound with the molecular formula C4H11NO, CAS 13325-10-5, and is an important building block for many bioactive molecules and drugs. It is a colorless to slightly yellow liquid with a special odor. It is usually liquid, with a melting point below 0 ° C at standard temperatures and pressures. It is a polar compound with high water solubility. It has good solubility in polar solvents such as water and alcohols, while its solubility is lower in non-polar solvents. In addition, it is also easily soluble in strong acids such as hydrochloric acid and acetic acid, forming salts. Relatively stable at room temperature, but oxidative degradation may occur under conditions such as light, oxygen, and high temperature. N-ABU(4)-OL has certain stability to acids, bases, and heat, but may decompose under strong oxidants or high temperatures.
It has two active functional groups, amino and alcohol hydroxyl, which give it high reactivity. It can undergo chemical reactions with acids, bases, halogenated hydrocarbons, esters, and other substances. For example, it can react with acids to form salts, react with halogenated hydrocarbons for alkylation or amination, and react with esters for hydrolysis. Has certain biological activity within the organism. For example, it can serve as a substrate or inhibitor for certain enzymatic reactions, participating in metabolic processes within the organism.
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C.F |
C4H11NO |
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E.M |
89 |
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M.W |
89 |
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m/z |
89 (100.0%), 90 (4.3%) |
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E.A |
C, 53.90; H, 12.44; N, 15.71; O, 17.95 |
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Melting point 16-18 ° C (lit.), Boiling point 206 ° C (lit.), Density 0.967 g / ml at 25 ° C (lit.), Refractive index N20 / D ~ 1.462 (lit.), Flashpoint 226 ° f, Storage condition: store below + 30 ° C, Acidity coefficient (PKA) 15.10 ± 0.10 (predicted), Form liquid, Clear colorless to slightly yellow, Water solubility miscible, Air sensitive & hygroscopic, BRN 1731411.
We are the supplier of 4-Amino-1-Butanol.
N-ABU(4)-OL is an important organic compound with various uses, such as synthesizing bioactive molecules, drugs, solvents, and extractants. The following are the detailed steps and corresponding chemical equations of the laboratory synthesis method for product:
Laboratory synthesis method one:
HOCH2CH2CH2CH2OH+NH3+H2SO4 → NH2CH2CH2CH2CH2CH2OH+H2O
Step 1: Add 2.0 g (0.025 mol) of 1,4-butanediol, 2.5 mL of ammonia (30%), and 0.5 mL of sulfuric acid (10%) to a dry 50 mL round bottom flask.
Step 2: Heat the mixture to 150 ° C under nitrogen protection and maintain the reaction for 1 hour.
Step 3: After the reaction is completed, cool to room temperature.
Step 4: Add 25 mL of water and extract 10 mL three times with ether.
Step 5: Combine the ether extraction solution and dry with anhydrous sodium sulfate.
Step 6: Filter to remove sodium sulfate, then distill to remove ether.
Step 7: Collect the fraction at 105 ° C (1.6 kPa) to obtain N-ABU(4)-OL.
Laboratory synthesis method 2:
(CH3)2C=CHCH2OH+NaOH → CH3CHOHCH2CH2ONa+H2O
(CH3)2C=CHCH2OH+HCl → (CH3)2CClCH2CH2OH+NaCl
(CH3)2CClCH2CH2OH+H2O → (CH3)2C(OH)CH2CH2OH+HCl
Step 1: Add 3.0 g (0.033 mol) of 1,4-butanediol, 3.8 g of sodium hydroxide (0.086 mol), and 20 mL of water to a 50 mL round bottom flask.
Step 2: Heat the mixture to 90 ° C under nitrogen protection and maintain the reaction for 3 hours.
Step 3: After the reaction is completed, cool the mixture to room temperature.
Step 4: Add 25 mL of water and 5 mL of hydrochloric acid (37%), and heat to 80 ° C.
Step 5: Cool the mixture to room temperature and filter to remove the generated precipitate.
Step 6: Concentrate the filtrate to about 10 mL and extract it three times with ether, 10 mL each time.
Step 7: Combine the ether extraction solution and dry with anhydrous sodium sulfate.
Step 8: Filter to remove sodium sulfate, then distill to remove ether.
Step 9: Collect the fraction at 105 ° C (1.6 kPa) to obtain N-ABU(4)-OL.
4-amino-1-butanol (CAS number: 13325-10-5) is an important organic compound belonging to amino alcohols, with a molecular formula of C4H11NO and a molecular weight of 89.14. It is a colorless or light yellow transparent liquid at room temperature, with hygroscopicity, soluble in water and common organic solvents (such as chloroform, acetone, ethyl acetate), chemically stable but needs to be stored in a sealed manner away from light and away from acidic substances.
Plays a key role in organic synthesis, especially in the construction of nitrogen-containing compounds, which are widely used. Its amino and hydroxyl functional groups can participate in various reactions, such as salt formation, esterification, etherification, etc., providing synthetic support points for complex molecules.
In the field of medicinal chemistry
Drug molecule modification: As a modifying group for nitrogen-containing drug molecules, amino or hydroxyl groups can be introduced to improve drug solubility, stability, or biological activity. For example, developing new drugs by modifying natural products or lead compounds.
Synthesis of bioactive molecules: used for synthesizing bioactive molecules such as choline and neuropeptides, which play important roles in physiological processes such as nerve conduction and cell signaling.
Specific drug intermediates: As intermediates of complex drugs such as Silipag (a drug used to treat pulmonary arterial hypertension), they participate in key reaction steps.
Materials Science Field
Polymer modification: Introducing it into polymer chains through copolymerization or grafting reactions to improve the flexibility, water resistance, or biocompatibility of materials. For example, in medical polymer materials, their amino groups can react with crosslinking agents to form a three-dimensional network structure.
Functional material synthesis: As ligands or monomers, participate in the construction of new materials such as metal organic frameworks (MOFs) and covalent organic frameworks (COFs), and utilize the coordination ability of their amino groups or hydrogen bonding of their hydroxyl groups to regulate the porosity and selectivity of the materials.
Industrial applications: surfactants and additives
Emulsifiers and cleaning agents
Emulsification: Its hydroxyl group can reduce the interfacial tension between oil and water, while the amino group can provide the electric charge repulsion force to form a stable lotion. For example, in cosmetics, it can be used as an emulsifier to prepare delicate cream or lotion.
Cleaning agent formula: As an additive to alkaline cleaning agents, its amino group can neutralize acidic dirt, and its hydroxyl group enhances its cleaning ability, making it suitable for metal cleaning, glass cleaning, and other scenarios.
Moisturizing agents and fabric finishing agents
Skin care: In skin care products, its moisturizing (hydroxyl) and mild (amino) properties can improve the skin barrier function and reduce water loss. It is commonly used in face cream, lotion and other products.
Textile industry: As a fabric finishing agent, its amino group can form covalent bonds with fibers, hydroxyl group enhances fiber moisture absorption, improves fabric softness and anti-static performance, and is widely used in the processing of natural fibers such as cotton and linen.
Special application: Acid gas absorption and protection group
Acidic gas absorbent
Industrial exhaust gas treatment: The alkaline amino group of N-ABU(4)-OL can react with acidic gases (such as CO ₂, SO ₂) to generate salts and reduce gas acidity. For example, in the treatment of exhaust gas from coal-fired power plants, its solution can absorb SO ₂ and reduce the formation of acid rain.
Laboratory gas purification: As a filler in drying tubes or absorption towers, it selectively absorbs acidic impurities and protects subsequent reaction systems.
Application of protective groups
N-tert-butoxycarbonyl (Boc) protection: The amino group of this product can be protected by Boc groups to form 4- (N-tert-butoxycarbonyl amino) -1-butanol (CAS number: 75178-87-9). This derivative serves as an intermediate in peptide synthesis, protecting the amino group from reaction conditions. Subsequently, the Boc group is removed under acidic conditions to release the target amino group.
Other protection strategies: Its hydroxyl group can also be protected through reactions such as silanization and esterification, for selective reactions of specific functional groups in multi-step synthesis.
Research field: Catalysts and reaction media
Catalyst development
Hydrogenation catalyst: Using this substance as a ligand, it forms a complex with ruthenium salt and can catalyze the hydrogenation of lactam to N-ABU(4)-OL. This reaction is carried out at low temperature and low pressure, with high yield and environmental friendliness, and has industrial application potential.
Asymmetric catalysis: Its chiral center (such as introducing chiral auxiliary) can induce asymmetric synthesis to prepare optically pure compounds for drug or fragrance synthesis.
Reaction medium and solvent
Polar non proton solvent: 4-amino-1-butanol has a moderate polarity and can be used as a reaction medium to promote certain organic reactions (such as Diels Alder reactions), increasing reaction rate or selectivity.
Phase transfer catalyst: Its amino group can form ion pairs with quaternary ammonium salts, promoting substance transfer in two-phase reactions (such as aqueous organic phase) and improving reaction efficiency.
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