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The Molecular formula of 3,4,5-Trimethoxyphenylacetonitrile (TMPAN for short) is C11H15NO3, CAS 13338-63-1, and its relative molecular weight is about 209.24. It usually exists in solid form and appears as a white to light yellow crystalline or powdery substance. It is soluble in common organic solvents, such as ethanol, Dimethyl sulfoxide and chloroform. It has a low solubility in water. It is an important intermediate and widely used in the field of drug synthesis. It can be used as a key raw material for the synthesis of various drugs, such as anticancer drugs, anti-inflammatory drugs and antipsychotic drugs. By chemically modifying and functionalizing TMPAN, compounds with specific biological activities can be synthesized. It is also widely used in the research of organic synthesis and Natural product synthesis. Due to the existence of several Methoxy group substituents, TMPAN has good chemical reactivity and selectivity. Researchers can use these characteristics to guide specific reaction pathways or synthesize complex organic molecules.
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Chemical Formula |
C11H13NO3 |
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Exact Mass |
207 |
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Molecular Weight |
207 |
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m/z |
207 (100.0%), 208 (11.9%) |
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Elemental Analysis |
C, 63.76; H, 6.32; N, 6.76; O, 23.16 |
3,4,5-Trimethoxyphenylacetonitrile (TMPAN) has multiple uses in the field of cosmetics.
1. perfume:As a compound with unique aromatic properties, TMPAN is widely used in the manufacture of perfume. It can endow perfume with special fragrance such as warmth, floral and fruity notes, and can increase the durability of perfume.
2. Facial skincare products:
TMPAN can be used in the formulation of facial skincare products, such as face cream, lotion, essence, etc. It has antioxidant and anti-inflammatory effects, can help reduce skin inflammation, promote cell regeneration, and provide moisturizing effect. In addition, due to its aromatic properties, it can also give the product a pleasant aroma.
3. lipstick and lipstick:
TMPAN is used as an additive in lipstick and lipstick to increase the stability and moisture retention of the product. It can provide a smooth texture, making the lip skin soft and preventing dryness and cracking. In addition, TMPAN can provide products with a sweet floral and fruity aroma.
4. facial mask and eye mask:
TMPAN is also commonly used in facial mask and eye masks. It can increase the moisturizing and nutritional properties of the product, help improve skin moisture balance, and reduce the appearance of fine lines and wrinkles. At the same time, TMPAN can also provide soothing and sedative effects, making skin healthier and younger.
5. Soap and shower gel:
TMPAN can be used as an additive in soap and shower gel, playing a cleaning and fragrance role in products. It can impart a charming floral and fruity aroma to the product and ensure that the skin is properly cleaned and moisturized.
6. Shampoo products:Some shampoo products, such as shampoo and conditioner, may also contain TMPAN. It can increase the stability and long-lasting fragrance of the product, and provide moisturizing and nourishing effects for hair. In addition, TMPAN can also improve the scalp condition and reduce Dandruff and inflammation.
7. Chemical research: TMPAN is also widely used in the research of organic synthesis and Natural product synthesis. Due to the existence of several Methoxy group substituents, TMPAN has good chemical reactivity and selectivity. Researchers can use these characteristics to guide specific reaction pathways or synthesize complex organic molecules.
8. Pesticides and insecticides: TMPAN also has certain applications in the agricultural field. Some studies have shown that by modifying the structure of TMPAN, efficient insecticides and pesticides can be synthesized to protect crops from pests.
9. Spices and essence: Because TMPAN has unique aromatic properties, this compound is often used to synthesize perfume, essence, condiments and other products. It can add special odors and fragrances to the product.
3,4,5-Trimethoxyphenylacetonitrile, also known as TMPAN, is an organic compound with the chemical formula C11H13NO3. Introduce several laboratory synthesis methods for TMPAN:
Method 1: use Phenethyl alcohol and Hydrogen cyanide to synthesize TMPAN
Synthesis steps:
1. Add Phenethyl alcohol into the reaction flask.
2. Add a dilute hydrochloric acid solution and stir it evenly.
3. Gradually drip Hydrogen cyanide solution into the reaction bottle.
4. The reaction should be carried out for several hours at room temperature.
5. Filter the reaction solution to obtain solid products.
6. Conduct crystallization, washing, and drying processes to obtain pure TMPAN.
Chemical equation:
C6H5CH2OH+HCN → C6H5CH2CN+H2O
C8H7N+3CH3OH → C11H13NO3+H2O
Method 2: TMPAN is synthesized with p-toluene and Cyanogen chloride
Synthesis steps:
1. Add p-toluene to the reaction flask.
2. Add Cyanogen chloride solution and stir it evenly.
3. The reaction should be carried out for several hours at room temperature.
4. Filter the reaction solution to obtain solid products.
5. Conduct crystallization, washing, and drying processes to obtain pure TMPAN.
Chemical equation:
C6H4 (CH3) 2+ClCN → C6H4 (CH3) 2CN+HCl
C9H9N+3CH3OH → C11H13NO3+HCl
Method 3: use 3,4,5-Trimethoxybenzoic acid and Thionyl chloride to synthesize TMPAN
Synthesis steps:
1. Dissolve 3,4,5-Trimethoxybenzoic acid in Thionyl chloride.
2. Conduct a reaction at an appropriate temperature for a period of time.
3. Cool to room temperature to allow the reactants to crystallize.
4. Conduct crystallization, washing, and drying processes to obtain pure TMPAN.
Chemical equation:
C6H3 (OMe) 3COOH+SOCl2 → C6H3 (OMe) 3COC1+SO2+HCl
C6H3 (OMe) 3COC1+HCN → C6H3 (OMe) 3CONC+HCl
These methods are several commonly used laboratory synthesis methods for synthesizing 3,4,5-Trimethoxyphenylacetonitrile, providing synthesis pathways starting from different starting materials.
What are the sales channels for this compound?
Manufacturer direct sales
Manufacturers usually establish their own sales teams or departments responsible for directly selling products to downstream users or traders. This sales model has a price advantage because it reduces intermediate links and can lower sales costs. At the same time, direct sales by manufacturers can ensure the quality of products and the stability of supply. Some well-known manufacturers, such as Hubei Julongtang Pharmaceutical Chemical Co., Ltd. and Zhende Chemical Technology (Shanghai) Co., Ltd., provide direct sales services for this compound.
Chemical trader distribution
Chemical traders play an important role as a bridge connecting producers and end-users. They usually purchase products from manufacturers and distribute them to downstream users through their own sales channels. Traders have flexible sales strategies, extensive customer resources, and rich market experience, and can adjust sales strategies and prices according to market demand. Therefore, distribution through chemical traders is one of the important channels for the sale of this substance.
Online platform sales
With the development of the Internet, network platform sales has gradually become one of the important channels for chemical product sales. Some chemical e-commerce platforms or B2B platforms provide their online sales services, where users can browse product information, compare prices, place orders, and make purchases. This sales model has the advantages of convenience, efficiency, transparency, etc., which can reduce transaction costs and improve transaction efficiency.
Direct procurement for scientific research or industrial users
Some large scientific research institutions or industrial enterprises have long-term or large-scale demand for this substance, and they usually establish long-term cooperative relationships with producers or traders to directly purchase products. This sales model can ensure product quality and supply stability, while reducing procurement costs and improving procurement efficiency.
Frequently Asked Questions
What is the relationship between its "trimethoxybenzene" structure and the classic hallucinogen "Moscalin"?
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It is the nitrile precursor or isomer of Mexicalin (trimethoxyphenethylamine). The parent nucleus structure is often used by medicinal chemists as a starting point for exploring central nervous system activity, but it is not necessarily related to hallucinogenic activity itself, but rather a synthetic block.
Why is its "cyanide group" an ideal "conversion handle" for constructing numerous heterocycles (such as tetrazoles and triazoles)?
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Cyan groups have extremely high reaction flexibility: they can be hydrolyzed to carboxylic acids, reduced to amines, cyclized with azides to synthesize tetrazole rings, or added with nucleophiles. This provides a core operating site for the rapid construction of structurally diverse heterocyclic compound libraries.
How is the methylene group (CH2CN) on the phenylacetonitrile backbone used to introduce the chiral center in the synthesis of chiral molecules?
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The hydrogen of the methylene group has a certain acidity and can form a carbon anion under the action of strong bases (such as LDA), which can then react with chiral adjuvants or chiral electrophilic reagents, or be separated by enzymatic kinetics to introduce chiral centers at the α - position and obtain optically active phenylacetonitrile derivatives.
How does it serve as a structural unit for constructing "conjugated systems" or "liquid crystal molecules" in materials chemistry?
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Trimethylbenzene is a good electron donor, and the phenylacetonitrile moiety can serve as an electron acceptor or connecting arm. By appropriate derivatization, it can serve as a core aromatic unit for constructing D-A type organic semiconductors, fluorescent dyes, or liquid crystal materials.
What are the toxicity and safety hazards that are often overlooked in its synthesis and use?
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Cyanide compounds are usually toxic, and their dust or vapor may irritate the respiratory tract and release cyanide ions through metabolism in the body. Meanwhile, as a potential precursor subject to regulation, it is required to comply with relevant laws and regulations, and may be unstable to light and heat, so caution should be exercised during operation.
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