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Hydroxylamine hydrochloride is an inorganic substance, molecular formula NH2OH · HCl, CAS 5470-11-1, which is a colorless crystal, easily deliquescent, white chemical substance, soluble in water, ethanol, glycerol, and cold ether. Colorless monoclinic crystal. Soluble in hot water, alcohol, glycerol, insoluble in ether. It has strong hygroscopicity, and will decompose when it is wetted above 151 ℃. It is mainly used as reducing agent and imaging agent. It is used in the preparation of oxime in organic synthesis. It is also used as raw material for the synthesis of anticancer drugs (hydroxyurea), sulfonamide drugs (sulfamethoxazole) and pesticides (methomyl).
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Chemical Formula |
ClH4NO |
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Exact Mass |
69.00 |
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Molecular Weight |
69.49 |
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m/z |
69.00 (100.0%), 71.00 (32.0%) |
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Elemental Analysis |
Cl, 51.02; H, 5.80; N, 20.16; O, 23.02 |
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Morphological |
Liquid |
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Color |
White to off-white |
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Melting point |
155 – 157 °C ( dec. ) ( lit. ) |
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Density |
1.67 g / mL at 25 ° C ( lit. ) |
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Hydroxyamine hydrochloride (chemical formula NH ₂ OH · HCl) is an important organic synthesis intermediate and chemical raw material. Since its industrial production in the mid-20th century, its application fields have expanded from the initial pharmaceutical synthesis to interdisciplinary fields such as pesticides, dyes, electronic materials, and analytical chemistry.
Synthesis of anticancer drugs
Hydroxyamine hydrochloride plays a crucial role in the development of anticancer drugs, and the hydroxylamine group (- NH ₂ OH) in its molecule can participate in DNA synthesis inhibition reactions. Typical applications include:
Synthesis of Hydroxyurea
Hydroxyurea is formed by the reaction of hydroxylamine hydrochloride with urea under acidic conditions. This drug inhibits the synthesis of deoxyribonucleic acid (DNA) by suppressing ribonucleotide reductase, thereby suppressing cancer cell proliferation. Clinical data shows that hydroxyurea has an effective rate of 60% -70% for chronic myeloid leukemia (CML), and the remission period for renal cell carcinoma and cervical cancer can be extended to 12-18 months.
Nucleoside analogue intermediate
Hydroxyamine hydrochloride participates in the synthesis of precursors of anti metabolic drugs such as 5-fluorouracil (5-FU), and inhibits tumor growth by interfering with tumor cell RNA synthesis.
Antibiotic raw materials
Hydroxyamine hydrochloride is a key raw material for the synthesis of sulfonamide drugs, and its sulfonylation products can form antibacterial active groups. Typical cases include:
Compound sulfamethoxazole (SMZ-TMP)
Hydroxyamine hydrochloride reacts with p-aminobenzenesulfonic acid to form sulfamethoxazole, which is then combined with trimethoprim (TMP) to form a broad-spectrum antibacterial agent. The minimum inhibitory concentrations (MIC) of the drug against Streptococcus pneumoniae and Pneumocystis carinii are 0.5-2 μ g/mL and 0.125-0.5 μ g/mL, respectively.
Synthesis of sulfamethoxazole (SD)
Hydroxyamine hydrochloride participates in the closed loop reaction of sulfamethoxazole, and the product has strong penetration into Neisseria meningitidis. It is commonly used to treat epidemic cerebrospinal meningitis.
Biomolecular synthesis
Hydroxyamine hydrochloride plays an important role in the synthesis of bioactive molecules, such as:
Peptide compound modification
Hydroxylamine hcl reacts with carboxyl protected amino acids to form hydroxamic acid esters, which are then deprotected and coupled to prepare peptides. This method can increase the yield of peptide chain synthesis by 15% -20% compared to traditional methods.
Intermediate of antibiotics
Hydroxyamine hydrochloride participates in the side chain synthesis of β - lactam antibiotics (such as cephalosporins), enhancing the antibacterial spectrum and stability of the drug.
Innovative applications in the field of pesticides
Insecticide synthesis
Hydroxyamine hydrochloride is the core raw material of carbamate insecticides, and its derivatives have the characteristics of high efficiency, low toxicity, and broad spectrum. Typical products include:
Methomyl
Hydroxyamine hydrochloride reacts with methyl isocyanate to produce methomyl, which has an LC ₅ ₀ (half lethal concentration) of 0.1-1.0 mg/L against aphids and cotton bollworms, and acts 3-5 times faster than organic phosphorus insecticides.
Carbofuran
Hydroxyamine hydrochloride participates in the synthesis of carbofuran, and the product has a control effect of 85% -95% on underground pests such as grubs and nematodes, with a duration of 45-60 days.
Development of fungicides
Hydroxyamine hydrochloride derivatives show potential in plant disease control, such as:
Hydroxylamine fungicides
A novel fungicide with inhibitory activity against rice blast fungus and wheat Fusarium graminearum has been developed by introducing long-chain alkyl or heterocyclic groups, with an EC ₅₀ (half effective concentration) of 1-10 μ g/mL.
plant growth regulator
Low concentration hydroxylamine hcl solution (10-50 mg/L) can induce plant stress resistance and improve crop tolerance to drought and salinity.
Hydroxyamine hydrochloride is a colorless or off white crystalline solid with strong hygroscopicity and susceptibility to moisture. Density 1.67g/cm3 (17 ℃), melting point 154 ℃ (decomposition), soluble in water, soluble in ethanol, glycerol, and glycerol, insoluble in ether.
The nitromethane method uses nitromethane and hydrochloric acid as raw materials to obtain hydroxylamine hydrochloride and formic acid under reflux conditions. Excess hydrochloric acid and formic acid are concentrated and distilled under reduced pressure, and then cooled, crystallized, centrifuged, and dried to obtain hydroxylamine hcl products. The reaction equation is as follows:
CH3NO2 +HCl+H2O → NH2OH·HCl+HCOOH
The nitromethane method is a traditional production method for hydroxylamine hcl in China, but this process has problems such as difficult raw materials, high material hazards, large amounts of three wastes, and high costs.
The nitric oxide reduction method uses ammonia, oxygen, and water as starting materials, and under Pt/Rh catalysis, ammonia oxidation is carried out to produce nitric oxide. Then, in hydrochloric acid solution, a mixture of gas and hydrogen is reduced under Pt catalytic conditions to produce hydroxylamine hcl aqueous solution. The reaction equation is:
4NH3 +5O2 → 4NO+6H2O 2NO+3H2+2HCl → 2NH2OH·HCl
The production process of nitric oxide reduction method is short and does not require oxime as a medium to directly produce hydroxylamine hcl. However, this process is complex, equipment requirements are high, precious metal catalysis costs are high, and there are many by-products. There is basically no industrial production equipment available.
The hydroxamic acid hydrolysis method uses oxime and hydrochloric acid as starting materials to separate hydroxylamine hcl solution and ketone through reactive distillation. The hydroxylamine hcl solution is concentrated, crystallized, and dried to obtain hydroxylamine hcl product, and the by-product ketone can be recycled for the preparation of oxime. The reaction equation is:
The oxime acid hydrolysis method has the characteristics of mild reaction conditions, short process, and less waste. However, this process has problems such as low one-way conversion rate, severe equipment corrosion, and poor product quality.
The ketoxime salt hydrolysis method is used to prepare hydroxylamine hcl from ketoxime hydrochloride, a byproduct of oxime silane production, and water. The reaction formula is:
The preparation of hydroxylamine hcl by direct hydrolysis of ketoxime hydrochloride produces almost no three wastes, has minimal corrosion to equipment, and uses only by-product ketoxime hydrochloride and water as raw materials, resulting in relatively low cost
There are three kinds of hydroxylamine hcl synthesis:
1. Sodium nitrite synthesis method (oximation method):
Add water to the reactor, add sodium nitrite under stirring, add sodium pyrosulfite in several times, and then acidify with sulfuric acid. The acidified material is sent to the hydrolysis kettle, acetone is added, then neutralized with liquid alkali, and the neutralizing solution is distilled to obtain acetone oxime. Acetone oxime and hydrochloric acid are added into the salt forming kettle to react to produce hydroxylamine hcl and acetone. Acetone recycling; Hydroxylamine hcl is concentrated, cooled and crystallized, centrifuged and dried to obtain the finished product. Raw material consumption quota: 1970kg/t sodium nitrite (95%), 5418kg/t sodium pyrosulfite (64% based on SO2), 1175kg/t acetone (98%). 2. Nitromethane method nitromethane reacts with hydrochloric acid and water to produce hydroxylamine hcl. According to hgb3044-76, hydroxylamine hcl product is white crystal, the content of secondary product ≥ 98.5, and the content of tertiary product ≥ 97%. Raw material consumption quota: nitromethane 1200kg/t, hydrochloric acid (30%) 1500kg/t.
2. Add water to dissolve sodium nitrite,
Add water to dissolve sodium nitrite, reduce the temperature to 0 ℃, add sodium bisulfite and 35% - 40% dilute sulfuric acid to make the solution ph=2, add acetone, stop stirring when the temperature rises to 35 ℃, increase the temperature to 70 ℃ for 3h, reduce the temperature to 30 ℃, add sodium hydroxide solution to pH 7-8. Evaporate acetone oxime by heating, add hydrochloric acid, maintain the temperature at 55 ~ 60 ℃, keep the temperature for 12h, and then concentrate. After a little cooling, decolorization, filtration, concentration, cooling and crystallization, the finished product is obtained. Refining can take ethanol immersion or water recrystallization.
Safety Protocols
To mitigate risks, the following measures are essential:
1) Personal Protective Equipment (PPE): Wear chemical-resistant gloves (e.g., nitrile), safety goggles, and lab coats. Use respirators with particulate filters if dust is generated.
2) Engineering Controls: Install fume hoods and local exhaust ventilation to minimize airborne exposure.
3) Storage: Keep containers tightly sealed in cool, dry areas away from oxidizers, bases, and heat sources.
4) Spill Management: Neutralize spills with water, collect solids in sealed containers, and dispose of as hazardous waste. Avoid using compressed air for cleanup.
Future Prospects
Research is exploring greener synthesis methods, such as enzymatic catalysis and electrochemical reduction, to reduce reliance on hazardous reagents. Additionally, its role in advanced materials-such as metal-organic frameworks (MOFs) for gas storage and catalytic applications-is gaining traction.
In the pharmaceutical sector, hydroxylamine hydrochloride's potential in synthesizing prodrugs and targeted drug delivery systems could revolutionize treatment modalities. However, addressing its toxicity through structural modifications (e.g., prodrug design) remains a critical challenge.
Hydroxylamine hydrochloride is a paradoxical compound: its toxicity necessitates caution, yet its chemical versatility drives innovation across industries. From life-saving drugs to eco-friendly water treatment, its applications underscore the delicate balance between risk and reward in industrial chemistry. As research advances, safer handling protocols and greener synthesis methods will ensure its continued relevance in a evolving scientific landscape.
By understanding its properties, applications, and safety requirements, scientists and engineers can harness the full potential of hydroxylamine hydrochloride while mitigating its hazards-a testament to the power of responsible chemical innovation.
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