Shaanxi BLOOM Tech Co., Ltd. is one of the most experienced manufacturers and suppliers of 2-acetonaphthone cas 93-08-3 in China. Welcome to wholesale bulk high quality 2-acetonaphthone cas 93-08-3 for sale here from our factory. Good service and reasonable price are available.
2-Acetonaphthone, also known as 2-acetylnaphthalene in Chinese, is a white to pale yellow powder. The molecular weight is 170.207, CAS 93-08-3, and the molecular formula is C12H10O. It is an endogenous metabolite that exists in smoke and has two positional isomers. As an intermediate, it is used to prepare piperidine pyrazole. Piperidine pyrazole is an effective DNA rotatase inhibitor with extensive applications in the pharmaceutical field. By using 2-acetylnaphthalene as an intermediate, we can more conveniently synthesize piperidine pyrazole and develop drugs for treating various diseases. It is also of great significance in scientific research and academic fields. It can serve as a starting material or intermediate for the synthesis of other organic compounds, providing chemists with an effective synthesis pathway. Meanwhile, for students and researchers, studying the properties and synthesis methods of 2-acetylnaphthalene can deepen their understanding and technical mastery of the field of organic chemistry.
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C.F |
C8H20O4Si |
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E.M |
208 |
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M.W |
208 |
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m/z |
208 (100.0%), 209 (8.7%), 209 (5.1%), 210 (3.3%) |
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E.A |
C, 46.12; H, 9.68; O, 30.72; Si, 13.48 |
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Melting point 52-56 ° C (lit.), Boiling point 300-301 ° C (lit.), Density 1.12 g / ml at 25 ° C (lit.), FEMA 2723 | METHYL BETA-NAPHTHYL KETONE, Refractive index N20 / D 1.628 (lit.), Flash point > 230 ° f, Sealed in dry, room temperature, Solubility 0.272g/l, Form fine crystal powder and chunks, Color white, Odor orange blossom odoror, Water soluble insoluble, JECFA Number811, Hazard Signs ( GHS ) , GHS07, GHS09 , Warning , Hazard description H401-H302-H315-H319-H335-H411 , P280a-P304 + P340-P405-P501a-P261-P273-P305 + P351 + P338-P264-P270-P280-P301 + P312 + P330-P302 + P352 + P332 + P313 + P362 + P364-P305 + P351 + P338 + P337 + P313-P501 , Dangerous goods sign Xn, Xi, N , Hazard category code 36 / 37 / 38-51 / 53-22-20 / 21 / 22 , Safety instructions 26-36-61-24 / 25-22-36 / 37 , Transport of dangerous goods number UN3077 , WGK Germany 3 , RTECS DB7084000 , Hazard Note Irritant , TSCA Yes , HazardClass 9 , Packing Group III , Customs Code 29143900 , Toxic skn-hmn 100 % FCTXAV 13,867,75
2-Acetonaphthone, with the chemical formula C12H10O, is an organic compound with a unique naphthalene ring structure. At room temperature and pressure, it is a white to light yellow powder with a strong orange blossom aroma. It is insoluble in water but soluble in common organic solvents. These physical and chemical properties make it widely applicable in the industrial field, especially as a key intermediate, playing an important role in promoting industrial upgrading.
Application in the dye industry
It plays a crucial role in dye synthesis, as its naphthalene ring structure provides a stable conjugated system for dye molecules, while the carbonyl unit enhances the reactivity of the molecule, allowing it to participate in various types of dye synthesis reactions.
Synthesis of azo dyes
Azo dyes are the largest and most widely used type of dyes in the dye industry, containing azo groups (- N=N -) in their molecules. 2-Naphthalenedione can undergo coupling reaction with diazonium salts to generate azo dyes with bright colors and good light resistance. For example, in the synthesis of certain red dyes, the naphthalene ring structure of 2-naphthylethyl ketone can stabilize the azo group, preventing it from decomposing under light, thereby improving the color fastness of the dye. In addition, the introduction of 2-naphthophenone can also adjust the solubility and dispersibility of dyes, making them more suitable for dyeing different fibers.
Synthesis of anthraquinone dyes
Anthraquinone dyes are a type of dye with excellent light and heat resistance, widely used in outdoor textiles, plastics, inks, and other fields. 2-Naphthalenedione can undergo condensation reaction with anthraquinone derivatives to generate anthraquinone dyes with complex structures. The naphthalene ring and anthraquinone units in these dye molecules together form a stable conjugated system, giving the dyes bright colors and long-lasting durability. For example, in the synthesis of certain blue dyes, the introduction of 2-naphthylethanone can significantly improve the dye's light resistance, making it less prone to fading during outdoor use.
Synthesis of other types of dyes
In addition to azo dyes and anthraquinone dyes, 2-naphthophenone can also be used to synthesize other types of dyes, such as phthalocyanine dyes, sulfide dyes, etc. In the synthesis of phthalocyanine dyes, 2-naphthylethanone can act as a ligand to form stable complexes with metal ions, thereby generating phthalocyanine dyes with special colors. These dyes have potential application value in fields such as optical recording materials and optical fibers.
Expansion of application areas: meeting diverse market demands
With the continuous development of the dye industry, the market's requirements for dye performance are becoming increasingly diverse. With its excellent chemical properties and reactivity, it provides more possibilities for the dye industry and meets the special needs of different fields for dyes.
High end textile dyeing
In the field of high-end textile dyeing, there are extremely high requirements for the color fastness, vividness, and environmental friendliness of dyes. The dye synthesized from this substance has excellent color fastness and vividness, and can reduce the content of harmful substances in the dye through chemical modification, meeting the needs of high-end textile dyeing. For example, when synthesizing certain environmentally friendly reactive dyes, its introduction can significantly reduce the content of heavy metal ions in the dyes, making them more in line with environmental standards.
Plastic coloring
Plastic coloring is one of the important application areas in the dye industry. The dye synthesized from this substance has excellent heat and light resistance, and its solubility can be adjusted through chemical modification, making it more suitable for plastic coloring. For example, in the synthesis of certain high-temperature plastic colorants, its introduction can enhance the heat resistance of the dye, making it less prone to decomposition during high-temperature processing.
Ink manufacturing
Ink manufacturing requires extremely high dispersion and stability of dyes. The dye synthesized from this substance has excellent dispersibility and stability, and its viscosity can be adjusted through chemical modification, making it more suitable for ink manufacturing. For example, in the synthesis of certain water-based inks, the introduction of 2-naphthophenone can enhance the affinity between the dye and water, allowing the dye to be evenly dispersed in water, thereby improving the printing effect of the ink.
Application in the spice industry
It is the core raw material of daily chemical essence, and is widely used to add fragrance to soap, detergent, shampoo, shower gel and other products. Typical application cases include:
Neroli scented essence: as the main fragrance agent, 2-Acetonaphthone can simulate the natural fragrance of neroli, and cooperate with citral, linalool, etc. to build a fresh and sweet aroma profile.
Citrus flavor essence: by cooperating with limonene, nerol, etc., 2-naphthyl ethyl ketone can enhance the fruit flavor characteristics of essence and enhance the attractiveness of the product.
Flower flavor essence: in rose, jasmine and other flower flavor essence, 2-naphthyl ethyl ketone can be used as a fixative to extend the fragrance retention time and stabilize the aroma structure.
Edible essence formula
According to the GB 2760-2014 standard, 2-Naphthalenedione is listed as a permitted food flavoring agent, which can be used for flavoring products such as candies, baked goods, cold drinks, and beverages. Typical application cases include:
Grape flavor essence: 2-naphthylethyl ketone, methyl ionone, ethyl acetate, etc. can simulate the mature aroma of grapes, and is widely used to enhance the flavor of wine, grape juice and other products.
Strawberry flavor essence: by cooperating with γ - caprolactone, vanillin, etc., 2-ethylnaphthone can build a sweet aroma of strawberries and improve the sensory quality of candy, ice cream and other products.
Citrus flavor essence: in orange juice, lemon tea and other drinks, 2-naphthanone can enhance the authenticity of the fruit flavor and cover up the bad flavor.
The unique aroma and excellent stability of 2-naphthanone make it a key raw material for high-end fragrance products (such as perfume and cologne). Typical application cases include:
Neroli perfume: in classic perfume such as Dior J'adore and Chanel No.
Citrus cologne: In products such as 4711 cologne and Acqua di Parma, 2-naphthophenone is combined with lemon, bitter orange leaves, etc. to create a fresh and vibrant aroma tone.
Oriental fragrance perfume: by cooperating with vanilla, patchouli, etc., 2-naphthylethyl ketone can add a warm and sweet tail to perfume and improve the durability of the product.
Innovative applications in the spice industry
Development of Natural Equivalent Flavors
With the increasing demand for natural ingredients among consumers, researchers have used biocatalytic technology to convert 2-naphthophenone into a natural equivalent fragrance. For example, using yeast or bacterial cell factories, 2-naphthophenone is synthesized from glucose as a raw material, and then converted into natural flavor molecules such as orange blossom alcohol or citral through enzymatic reactions. This technology not only conforms to the concept of green chemistry, but also reduces production costs.
Microencapsulation technology for spices
The aroma of 2-naphthophenone is easily influenced by environmental factors, and its stability can be significantly improved through microencapsulation technology. For example, with β - cyclodextrin as the wall material, 2-naphthanone can be embedded by spray drying method to form microcapsules with a particle size of 1-10 μ m. This microcapsule is stable within the pH range of 3-9 and can release fragrance under heating or friction conditions, making it suitable for the development of products such as laundry beads and fragrance wipes.
Fragrance photosensitive material composite system
The fluorescence properties of 2-Acetonaphthone it to be combined with photosensitive materials such as titanium dioxide and zinc oxide to construct a self-cleaning fragrance coating. For example, by loading 2-naphthylethyl ketone onto the surface of titanium dioxide nanoparticles, coatings with antibacterial, anti fouling, and long-lasting fragrance functions can be prepared, which are widely used in fields such as automotive interiors and home building materials.
Frequently Asked Questions
Can its "position selectivity" be regulated in the Freidel Crafts reaction?
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Yes, solvent polarity is the key switch.
During preparation, acetylation of naphthalene can occur at the 1-position (α) and 2-position (β). Uncommon process details: In non-polar solvents such as carbon disulfide, the proportion of alpha isomers is relatively high; In polar solvents such as nitrobenzene, the proportion of β - isomer (i.e. target product 2-acetylnaphthalene) significantly increases due to the increased steric hindrance of complex formation. Choosing a solvent means choosing an isomer.
Why is its triplet state "inert"? What are the inspirations for photochemical research?
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Because its triplet state is of π - π type, not n - π.
Early photochemical research confusion: 2-acetylnaphthalene does not undergo photoreduction reactions with alcohols like ketones such as acetophenone. Research has confirmed that the lowest triplet energy level is π - π, rather than the n - π triplet state necessary for hydrogen abstraction reactions. Therefore, although it can sensitize other reactions, it is "photochemically inert" and is an ideal tool for studying energy transfer rather than hydrogen atom transfer.
What is its' hidden identity 'in the field of polymers?
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Can be used as a UV curing photoinitiator.
In addition to its conventional use as a fragrance and intermediate, 2-acetylnaphthalene can be used as a photoinitiator or photosensitizer in the development of UV curable coatings and inks due to its absorption characteristics of ultraviolet light and its ability to transfer triplet energy. This utilizes its ability to induce monomer polymerization after absorbing light energy, rather than just existing as a fragrance.
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