*Product Photos
| Item | Salicylonitrile 2-Cyanophenol o-Cyanophenol |
| Purity | 99.8 |
| CAS NO. | 611-20-1 |
Product Introduction
1. Core Definition & Basic Information
It is an aromatic nitrile compound containing an aromatic ring, a hydroxyl group and a cyano group. Its molecular formula is C₇H₅NO, molecular weight is 119.12, and EINECS number is 210-259-3. In its molecular structure, the hydroxyl group (-OH) and cyano group (-CN) are located at the ortho-position of the benzene ring. This unique substituent arrangement endows it with both the active hydrogen characteristics of phenolic compounds and the nucleophilic reactivity of nitrile compounds, resulting in high chemical activity. It serves as an important bifunctional synthetic intermediate in the fine chemical industry and is widely applied in the chain synthesis of high-value-added products.
2. Detailed Physicochemical Properties
2.1 Appearance & Odor
Industrial-grade products appear as off-white to light brown crystalline powder with uniform particle size and no obvious caking. High-purity reagent-grade products are white to pale yellow acicular crystals with regular crystalline morphology and good gloss. Both types of products have a characteristic pungent odor typical of aromatic nitriles. The odor intensity decreases slightly with the increase of purity, which does not affect their chemical stability.
2.2 Key Physical Parameters
- Melting Point: 92-95℃ (The melting point range narrows when purity ≥ 98.0%; for every 1% increase in purity, the melting point fluctuation range decreases by 0.3-0.5℃)
- Boiling Point: 273.1℃ (under standard atmospheric pressure of 760mmHg). It has low decomposition risk during atmospheric distillation and is suitable for conventional separation and purification processes.
- Flash Point: 109.6℃. It is classified as a combustible solid and must be kept away from open flames and high-temperature heat sources.
- Density: Approximately 1.22g/cm³ (at 25℃), with a bulk density of 0.6-0.7g/cm³, facilitating metering during industrial feeding.
- Solubility: At 25℃, its solubility in water is about 5g/L. It is miscible with common organic solvents such as ether, acetone, toluene and other similar solvents in any proportion, and has better solubility in polar aprotic solvents like DMF and DMSO, suitable for various synthetic systems including homogeneous catalysis and heterogeneous reactions.
- Vapor Pressure: 0.0035mmHg (at 25℃). It has low volatility at room temperature, leading to minimal risk of vapor accumulation during operation.
2.3 Chemical Characteristics
The ortho-effect of the hydroxyl group significantly enhances the reactivity of the cyano group, enabling it to undergo various organic reactions such as hydrolysis, reduction, substitution and cyclization. Hydrolysis reaction can produce salicylic acid; reduction reaction can yield corresponding amino-containing aromatic compounds; condensation with aromatic amine compounds can construct heterocyclic structures. These chemical characteristics lay the structural foundation for its applications in multiple fields.
3. Product Specifications & Quality Control
Industrial Grade: Purity ≥ 98.0% (tested by High-Performance Liquid Chromatography, area normalization method), suitable for large-scale synthesis of pesticides and chemical intermediates.
Reagent Grade: Purity ≥ 99.0% (tested by HPLC). Some high-end reagent-grade products can reach a purity of over 99.5%, meeting the stringent impurity control requirements of pharmaceutical synthesis and laboratory precision research and development.
Impurity Control: Single impurity content ≤ 0.3%, total impurity content ≤ 1.0%. The content of key harmful impurities (such as heavy metals and chloride ions) is ≤ 10ppm, complying with international environmental standards for chemical raw materials.
Moisture Content: ≤ 0.5% (tested by Karl Fischer method), preventing catalyst deactivation or increased side reactions in synthetic processes caused by moisture.
Appearance Requirement: Free of visible mechanical impurities (screened through a 40-mesh standard sieve), with uniform color and luster, conforming to the morphological standards of the corresponding grade.
4. Core Functions & Application Fields
The core function of 2-hydroxybenzonitrile (also referred to as o-hydroxybenzonitrile, salicylonitrile) is to serve as a high-performance bifunctional synthetic intermediate. Relying on the synergistic reactivity of its ortho-hydroxyl and cyano groups, it plays a key role in "structural construction" and "functional introduction" in the synthesis of downstream products. The specific application scenarios and mechanisms are as follows:
4.1 Pesticide Field: Core Raw Material for Methoxyacrylate Fungicides
Application Products: Azoxystrobin, a world-leading high-efficiency, broad-spectrum and low-toxicity fungicide, widely used in the prevention and control of fungal diseases in various crops such as rice, wheat, corn, cotton, vegetables and fruits.
Mechanism of Action: As a key precursor of the "benzene ring-heterocycle" structure in the azoxystrobin molecule, this product constructs the core active skeleton of azoxystrobin through condensation reaction with substituted phenoxyacetone, hydroxylamine and other raw materials. Its purity directly affects the yield of the condensation reaction (the synthetic yield corresponding to industrial-grade products is about 85-90%, while that of reagent-grade products can be increased to over 92%).
Application Value: Azoxystrobin exerts its fungicidal effect by inhibiting the mitochondrial respiration of fungi, and has protective, curative and eradicative effects on dozens of fungal diseases such as rice blast, powdery mildew and downy mildew. The stable supply of 2-hydroxybenzonitrile is the core guarantee for the industrial production of such pesticides, helping to improve the quality and efficiency of agricultural production.
4.2 Pharmaceutical Field: Intermediate for Cardiovascular Drugs
Application Products: a clinically commonly used non-selective β-receptor blocker with weak α-receptor blocking activity.
Mechanism of Action: In the synthesis of this pharmaceutical product, 2-hydroxybenzonitrile introduces the o-hydroxyphenyl structure through ring-opening and amination reactions with relevant raw materials. This structure is the key pharmacophore for bunolol to bind to β-receptors, directly affecting the bioavailability and pharmacological activity of the drug.
Application Value: Bunolol is mainly used clinically in the treatment of hypertension, angina pectoris, arrhythmia, glaucoma and other diseases, with stable antihypertensive effect and few side effects. The high purity and reaction selectivity of 2-hydroxybenzonitrile are important prerequisites for ensuring the quality and safety of bunolol.
4.3 Fine Chemical Field: Intermediate for Functional Materials & Fragrance Synthesis
Liquid Crystal Materials Direction: The aromatic ring structure of 2-hydroxybenzonitrile has good rigidity. The hydroxyl and cyano groups can act as hydrogen bond donors and acceptors between molecules, participating in the self-assembly and arrangement of liquid crystal molecules. By condensing with other liquid crystal mesogens (such as relevant aromatic and ester structures), liquid crystal materials with specific phase transition temperature and response speed can be prepared, which are applied in liquid crystal displays, liquid crystal sensors and other electronic devices to improve the display clarity and stability of the devices.
Fragrance Synthesis Direction: 2-hydroxybenzonitrile can be converted into aromatic compounds with floral and fruity characteristics (such as o-hydroxybenzoate esters and o-hydroxybenzyl alcohol derivatives) through multi-step reactions such as hydrolysis, esterification and reduction. These compounds have fresh and long-lasting aromas, and can be used in the preparation of perfumes, essences, cosmetic fragrances and food additives, enriching the fragrance types of fragrance products.
4.4 Other Application Fields
Organic Synthetic Reagent: Used in the construction of heterocyclic compounds and modification of aromatic molecular structures in laboratory organic synthesis reactions.
Dye Intermediate: Introducing different chromophores through substitution reactions to synthesize dyes with specific colors, applied in textile, printing and other industries.
Corrosion Inhibitor Raw Material: Its hydroxyl and cyano groups can form an adsorption film on the metal surface to inhibit metal corrosion, suitable for the corrosion protection of industrial equipment and pipelines.
5. Storage & Operation Specifications
5.1 Storage Conditions
Environmental Requirements: Sealed and stored in a dry, cool and well-ventilated warehouse. The relative humidity of the warehouse should be controlled at 50-70%, and the storage temperature should be below 30℃ to avoid direct sunlight.
Isolation Requirements: Keep away from fire sources and heat sources (such as boilers and heaters). Store separately from strong oxidants and acidic substances with an isolation distance of not less than 10 meters. Prohibit mixed storage (to prevent hydrolysis and oxidation side reactions of cyano groups).
Shelf Life & Packaging Maintenance: The shelf life is 12 months in the original packaging. After opening, seal it with a sealing clip in a timely manner to avoid moisture absorption. It is recommended to use up the product within 3 months after opening.
Warehouse Management: The warehouse should be equipped with dry powder fire extinguishers, sand and other fire-fighting equipment, and ventilation devices should be installed. Smoking and open flames are prohibited in the warehouse. Regularly check whether the packaging is damaged or leaking.
5.2 Operation Specifications & Safety Protection
Personal Protection: During operation, must wear KN95 grade protective masks complying with GB 2626-2019 standard (to prevent dust inhalation), chemical-resistant nitrile gloves (to avoid direct skin contact) and goggles (to prevent dust or solution from splashing into the eyes). Wear protective clothing when necessary.
Operating Environment: Carry out feeding, weighing, transferring and other operations in a fume hood or well-ventilated operating area. Avoid generating a large amount of dust during operation. If dissolution is required, slowly add the product to the solvent and stir to prevent local overheating.
Emergency Treatment:
- Skin Contact: Immediately rinse the contact area with a large amount of flowing water for more than 15 minutes. Seek medical attention if redness, swelling, itching and other discomfort occur.
- Eye Contact: Immediately rinse the eyes with an eyewash for 15 minutes (keep the eyelids open), then seek medical attention.
- Inhalation: Quickly move to a place with fresh air, keep the respiratory tract unobstructed. Seek medical attention if symptoms such as cough and chest tightness occur.
- Leakage Treatment: For small leaks, cover and absorb with sand or dry lime, and collect into a sealed container. For large leaks, demarcate a warning area, collect and transfer to a safe place with explosion-proof equipment for disposal to avoid environmental pollution.
6.FAQ
Q: What are the core application scenarios and functions of 2-hydroxybenzonitrile?
A: It is mainly applied in three fields: first, as the core synthetic raw material for methoxyacrylate fungicides (such as azoxystrobin) to help prevent and control fungal diseases in agriculture; second, as an intermediate for cardiovascular drugs to participate in the construction of drug pharmacophores; third, used in the synthesis of liquid crystal materials and fragrances to endow products with specific functions and properties. Its core function is to serve as a bifunctional synthetic intermediate, providing structural support and functional introduction for downstream high-value-added products.
Q: What key conditions should be focused on when storing 2-hydroxybenzonitrile, and why?
A: Three key points need to be focused on: first, sealed and moisture-proof (moisture content ≤ 0.5%), because moisture will cause catalyst deactivation or side reactions in synthetic reactions; second, low-temperature storage (temperature below 30℃) to avoid product volatilization or oxidation caused by high temperature; third, isolated storage (away from strong oxidants and acids) to prevent hydrolysis and oxidation side reactions of cyano groups that affect product quality. The shelf life is 12 months in the original packaging. Seal and use it as soon as possible after opening.
Q: What are the differences in appearance and application of 2-hydroxybenzonitrile with different purity grades?
A: In terms of appearance, industrial-grade products (≥ 98.0%) are off-white to light brown crystalline powder, while reagent-grade products (≥ 99.0%) are white to pale yellow acicular crystals. The higher the purity, the lighter the color and the more regular the crystalline morphology. In terms of application, industrial-grade products are suitable for large-scale pesticide and chemical synthesis, while reagent-grade products are suitable for pharmaceutical synthesis, laboratory precision research and development and other scenarios with higher impurity control requirements. High-purity products can improve the yield and purity of downstream synthetic reactions.
India
