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2,5-DIMETHOXYPHENYLLACETONITRILE, CAS 18086-24-3
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The reaction of Benzyl cyanide hydrogenation to Phenethylamine.
It is prepared by catalytic hydrogenation of Benzyl cyanide under pressure. The liquid ammonia is introduced into Benzyl cyanide, cooled and absorbed, mixed with Raney nickel nickel and added into the Autoclave to remove air and introduce hydrogen. React at around 10 MPa at 80-120 ℃ for 3 hours until no hydrogen is absorbed, cool, relieve pressure, and filter. Take the filtrate for vacuum distillation and collect the 90-93 ℃ (2kPa) fraction, which is 2-phenylethylamine. The yield is 90%.
If preparing 2-phenylethylamine hydrochloride (156-28-5), take the above filtrate, adjust it to pH 3-4 with hydrochloric acid below 60 ℃, cool it to 5 ℃, let it stand for 8 hours, and filter to obtain it. Hydrochloride is a sheet-like crystal. Melting point 223-224 ℃ (217 ℃).
DMAN Molecular formula is C10H11NO3, CAS 18086-24-3, and its relative molecular weight is about 193.20. It usually exists in solid form and appears as a white to light yellow crystalline or powdery substance. The refractive index is approximately between 1.529 and 1.532. It is a relatively stable compound that does not undergo significant decomposition under conventional storage conditions. However, it may be sensitive to light and Air sensitivity, so care should be taken to avoid long-term exposure to light and air when storing and using it. It is an organic compound with multiple uses and can be used as a pharmaceutical intermediate for synthesizing other compounds with pharmacological activity. It is widely used in the field of chemical research. It can be used as an organic reagent and intermediate, participating in various organic synthesis reactions. Researchers can use DMAN for the synthesis of new compounds to explore new chemical properties and applications.
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Chemical Formula |
C10H11NO2 |
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Exact Mass |
177 |
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Molecular Weight |
177 |
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m/z |
177 (100.0%), 178 (10.8%) |
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Elemental Analysis |
C, 67.78; H, 6.26; N, 7.90; O, 18.06 |
2,5-Dimethoxyphenylacetonitrile (DMAN) has multiple uses in the field of pesticides. The following is a description of the various uses of DMAN in the field of pesticides:
Insecticides:DMAN is one of the important components of many insecticides. It can be used as an intermediate in the preparation of various insecticides. The structure of DMAN endows it with certain insecticidal activity, and its insecticidal properties can also be enhanced or changed by modifying its structure. According to demand, different types of DMAN derivatives can be synthesized for specific pest control. DMAN derivatives have extensive applications in controlling agricultural pests such as aphids, moths, and beetles.
Herbicides:DMAN can also be used to synthesize various herbicides. The main goal of herbicides is to suppress or kill weeds and protect crops from weed competition. DMAN can serve as an intermediate for herbicides and react with other compounds in chemical reactions to generate effective herbicides. The synthesized DMAN derivatives can exert their effects through leaf absorption or soil conduction, controlling different types of weeds.
Fungicides:DMAN is also widely used in the manufacturing of fungicides. Fungicides are chemicals used to prevent and control crop diseases. DMAN can synthesize various fungicides by reacting with other compounds. These fungicides can be used for the prevention and treatment of diseases related to fungi, bacteria, and viruses. DMAN derivatives protect the health and yield of crops by inhibiting the growth and reproduction of pathogenic microorganisms.
Plant growth regulators:In addition to the insecticides, herbicides, and fungicides mentioned above, DMAN can also be used for the production of plant growth regulators. Plant growth regulators are a class of chemicals that can increase or inhibit plant growth. DMAN derivatives can alter the physiological processes of plants, such as growth rate, flower bud differentiation, and fruit development. Plant growth regulators prepared using DMAN derivatives can promote plant growth and development, increase crop yield, or improve crop quality.
Environmentally friendly pesticides:With the increasing awareness of environmental protection, the demand for environmentally friendly pesticides is also increasing. DMAN derivatives are widely used in the synthesis of environmentally friendly pesticides. These pesticides not only control pests, weeds, and diseases, but also have minimal impact on non target organisms and the environment. The design and synthesis of DMAN derivatives can consider factors such as their degradability, conductivity, and residue exclusion to reduce negative impacts on the environment and ecosystems.
Cosmetics field:In the field of cosmetics, DMAN can be used to synthesize spices and essential oils. Its special chemical structure makes it possible to synthesize highly effective perfume ingredients. Meanwhile, DMAN can also be used as a stabilizer and solvent to help maintain the quality and stability of cosmetic products.
A common synthesis method for 2,5-Dimethoxyphenethylamine is through benzylcyanide reaction and subsequent acylation reaction. The specific steps are as follows:
Step 1: Benzyl cyanide reaction:
2,5-Dineneneba methoxy Benzaldehyde is reacted with Sodium cyanide in a suitable solvent. The reaction is usually carried out in an inert atmosphere to prevent the influence of oxygen. The reaction conditions can be selected according to the specific situation at appropriate temperature and reaction time.
C9H10O3+CNNa → 2,5-di Methoxy group benzyl cyanide
Step 2: Acylation reaction:
React 2,5-di Methoxy group benzyl cyanide generated in step 1 with appropriate acylating reagent to generate 2,5-Dimethoxyphenylacetonitrile. The acylation reagent can be anhydride or acyl chloride, and the reaction is usually carried out under alkaline conditions.
2,5-Dineneneba methoxy benzyl cyanide+acylation reagent → C10H11NO2
Adverse reactions
2,5-Dimethoxyphenylacetonitrile is an organic compound with certain uses in the field of chemical synthesis, such as as as a raw material for the synthesis of certain drugs, fragrances, or other organic intermediates. However, like many chemicals, it may cause a series of adverse reactions when in contact with the human body or the environment. A thorough understanding of these adverse reactions is crucial for safeguarding human health, environmental protection, and the rational use of this compound.
Acute toxic reaction
Oral toxicity
When the human body or experimental animals ingest a large amount of 2,5-dimethoxyphenylacetonitrile at once, it may cause acute poisoning symptoms. Early symptoms of gastrointestinal irritation such as nausea, vomiting, abdominal pain, and diarrhea may occur due to the direct stimulation of compounds on the gastrointestinal mucosa, which disrupts the normal structure and function of the mucosa, leading to disrupted secretion of digestive fluids and abnormal gastrointestinal motility. As the degree of poisoning worsens, neurological symptoms such as dizziness, headache, fatigue, drowsiness, and in severe cases, coma, convulsions, etc. may occur. This is because compounds may enter the central nervous system through blood circulation, interfere with the normal metabolism and signal transmission of nerve cells, affect the synthesis, release, and receptor function of neurotransmitters, and thus cause neurological dysfunction.
Skin contact toxicity
When exposed to large amounts of 2,5-dimethoxyphenylacetonitrile liquid or high concentration vapor in a short period of time, the skin may exhibit acute dermatitis symptoms such as erythema, edema, and blisters. This is because compounds can directly stimulate skin cells, trigger inflammatory reactions, cause skin blood vessel dilation and increased permeability, causing fluid to seep into tissue gaps, forming edema and blisters. At the same time, it may also be accompanied by discomfort such as itching and pain, which seriously affects the normal function of the skin.
Inhalation toxicity
Inhalation of vapor or dust of 2,5-dimethoxyphenylacetonitrile may cause strong irritation to the respiratory tract. Causing symptoms such as coughing, sputum production, wheezing, and difficulty breathing, and in severe cases, may lead to chemical pneumonia or pulmonary edema. This is because the compound stimulates the respiratory mucosa, causing congestion, edema, increased secretion, obstruction of the respiratory tract, and affecting gas exchange. At the same time, compounds may also enter the alveoli, damaging alveolar epithelial cells and capillary endothelial cells, causing fluid to seep into the alveolar cavity, forming pulmonary edema, further exacerbating breathing difficulties, and even endangering life.
Toxicity to specific organ systems
Neurological system
Long term or extensive exposure to 2,5-dimethoxyphenylacetonitrile may cause cumulative damage to the nervous system. In addition to the neurological symptoms that occur during acute poisoning, chronic exposure may lead to changes in neurobehavior, such as memory loss, lack of concentration, and delayed response. It may also cause peripheral neuropathy, manifested as limb numbness, pain, sensory abnormalities, etc. This is due to the damage of compounds to peripheral nerve fibers, which affects the transmission of nerve impulses.
Reproductive system
2,5-dimethoxyphenylacetonitrile may have certain toxic effects on the reproductive system. In animal experiments, it has been found that long-term exposure to this compound may cause damage to reproductive cells, affect the quality of sperm and eggs, and reduce fertility. For pregnant women, there may be an increased risk of fetal abnormalities, which may be related to compounds interfering with the normal development of germ cells and early development after embryo implantation.
Endocrine system
This compound may also interfere with the endocrine system. It can simulate or interfere with the action of hormones in the body, affecting hormone synthesis, secretion, and metabolism, leading to endocrine disorders. For example, it may affect the secretion of thyroid hormones, causing thyroid dysfunction, manifested as symptoms such as thyroid enlargement, hyperthyroidism, or hypothyroidism; It may also affect hormone levels, leading to menstrual disorders, sexual dysfunction, and other issues.
Skin and eye irritation
Skin irritation
Even if not exposed in large quantities for a short period of time, long-term repeated exposure to low concentrations of 2,5-dimethoxyphenylacetonitrile may cause chronic skin irritation symptoms. Manifested as dry, rough, and cracked skin, with chronic eczema like changes, impaired skin barrier function, and susceptibility to secondary infections. This is because the compound continuously stimulates the skin, disrupting its normal structure and physiological functions, resulting in a decrease in the skin's moisturizing and defense abilities.
Eye irritation
When 2,5-dimethoxyphenylacetonitrile splashes into the eyes, it immediately causes severe eye pain, tearing, photophobia, eyelid spasms, and other symptoms. This is because the compound has a strong irritant effect on the conjunctiva and cornea, which can cause conjunctival congestion, edema, corneal epithelial damage, and in severe cases, may lead to corneal ulcers, perforation, affect vision, and even permanent blindness.
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