577-59-3 Usage
Description
2-Nitroacetophenone, also known as 2'-Nitroacetophenone, is an organic compound that serves as a crucial intermediate in various chemical syntheses. It is characterized by its yellow-green appearance, either in liquid or crystalline form, and is soluble in alcohol, ether, and chloroform, with slight solubility in water. Its chemical structure and properties make it a versatile compound for use in different industries.
Uses
Used in Organic Synthesis:
2-Nitroacetophenone is used as an important raw material and intermediate in organic synthesis, playing a vital role in the creation of various complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Nitroacetophenone is utilized as a synthetic reagent and a pharmaceutical intermediate. Its unique chemical properties allow it to be a key component in the development of new drugs and medications.
Used in Agrochemicals:
2-Nitroacetophenone is also employed in the agrochemical industry, where it serves as an intermediate for the synthesis of various agrochemical products, contributing to the development of effective solutions for agricultural needs.
Used in Dye Industry:
In the dye industry, 2-Nitroacetophenone is used as an intermediate for the production of different types of dyes. Its chemical properties make it suitable for creating a wide range of colors and pigments.
Used in Photosensitive Materials:
2-Nitroacetophenone is a compound that finds application in the synthesis of photosensitive materials, where it acts as a sensitizer, enhancing the light-sensitive properties of these materials.
Preparation
o-Nitroacetophenone is synthesized from o-nitroethylbenzene by oxidation. Add o-nitroethylbenzene, decanoic acid and initiator azobisisobutyronitrile into the reaction tower, and at the same time slowly pass air into the tower, keep the pressure at 0.3-0.8MPa, and control the oxidation at 120-130°C to generate 2-Nitroacetophenone.
Synthesis Reference(s)
The Journal of Organic Chemistry, 43, p. 3631, 1978 DOI: 10.1021/jo00412a058Journal of the American Chemical Society, 105, p. 943, 1983 DOI: 10.1021/ja00342a050Synthesis, p. 228, 1988 DOI: 10.1055/s-1988-27522
Air & Water Reactions
Insoluble in water.
Fire Hazard
2-Nitroacetophenone is combustible.
Check Digit Verification of cas no
The CAS Registry Mumber 577-59-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,7 and 7 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 577-59:
(5*5)+(4*7)+(3*7)+(2*5)+(1*9)=93
93 % 10 = 3
So 577-59-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H7NO3/c10-8(6-9(11)12)7-4-2-1-3-5-7/h1-5H,6H2
577-59-3Relevant articles and documents
Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds
Li, Zhibin,Zhang, Yan,Li, Kuiliang,Zhou, Zhenghong,Zha, Zhenggen,Wang, Zhiyong
, p. 2134 - 2141 (2021/09/29)
A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]
Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation
Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei
supporting information, p. 5905 - 5908 (2021/06/18)
A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.
Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer
Wu, Cunluo,Bian, Qilong,Ding, Tao,Tang, Mingming,Zhang, Wenkai,Xu, Yuanqing,Liu, Baoying,Xu, Hao,Li, Hai-Bei,Fu, Hua
, p. 9561 - 9568 (2021/08/06)
A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.