6706-92-9

Usage

Chemical class

2,2'-Dimethoxybenzil belongs to the class of benzils, which contain two benzoyl groups joined by a central carbon atom.

Light sensitivity

2,2'-Dimethoxybenzil is a light-sensitive and photoreactive compound.

Uses

The compound is often used in the synthesis of organic and pharmaceutical compounds, and has potential applications in photoresists and photosensitive materials.

Photoreactions

2,2'-Dimethoxybenzil is known for its ability to undergo photoreactions, forming a range of products including ketones, aldehydes, and dimers.

Research interest

The compound has attracted interest in the field of chemical research due to its unique properties and potential applications in photochemistry and material science.

InChI:InChI=1/C16H14O4/c1-19-13-9-5-3-7-11(13)15(17)16(18)12-8-4-6-10-14(12)20-2/h3-10H,1-2H3

Upstream product

• 6706-96-3 2,2'-dimethoxybenzoin 
• 106675-70-1 N¹,N²-dimethoxy-N¹,N²-dimethyloxalamide 
• 31600-86-9 2-methoxyphenyllithium 
• 72371-46-1 (2-methoxy-phenyl)-glyoxylonitrile 
• 93-59-4 Perbenzoic acid 
• 67-66-3 chloroform 
• 28358-60-3 1-methoxy-2-[1-(2-methoxyphenyl)ethenyl]benzene 
• 306990-93-2 (1H-benzo[d][1,2,3]triazol-1-yl)(2-methoxyphenyl)methanone 
• 135-02-4 ortho-anisaldehyde 
• 5293-78-7 2,2'-dimethoxytolane 
• 142472-15-9 1,3-bis(o-methoxyphenyl)-propane-1,3-dione 
• 64158-26-5 1,2-di-(2-methoxyphenyl)-ethylene glycol 
• 77-78-1 dimethyl sulfate 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 130728-42-6 5,6-bis-(2-methoxy-phenyl)-2H-[1,2,4]triazine-3-thione 
• 14310-34-0 1,2-bis(2-methoxyphenyl)ethane 
• 85-26-7 2,2'-dihydroxybenzil 
• 107943-61-3 1-(2-hydroxyphenyl)-2-(2-methoxyphenyl)ethane-1,2-dione 
• 4936-01-0 2,2'-dimethoxy-benzilic acid 
• 132569-50-7 5,5'-dibromo-2,2'-dimethoxy-benzil 
• 90585-33-4 2,2'-dimethoxybenzil dihydrazone 
• 855948-16-2 2,2'-dimethoxy-5,5'-dinitro-benzil 
• 412034-32-3 2,2'-dimethoxy-3,5'-dinitro-benzil 
• 90833-62-8 7-hydroxy-2,3-bis(2-methoxyphenyl)-6-quinoxalinecarboxylic acid 
• 90833-61-7 2,3-bis(2-methoxyphenyl)-6-quinoxalinecarboxylic acid 
• 90833-28-6 2,3-bis-(2-methoxyphenyl)-5-quinoxalinecarboxylic acid 
• 4464-76-0 (1R,2S)-1,2-bis(4-methoxyphenyl)-1,2-ethanediol 
• 66768-20-5 (R,R)-(+)-1,2-bis(4-methoxyphenyl)ethane-1,2-diol 

Relevant academic research and scientific papers

Method for preparing intermediate of chiral vicinal diamine

The invention discloses a method for preparing an intermediate of chiral vicinal diamine. The method comprises the following steps: adding a compound IV into a solvent, stirring the compound IV and the solvent in an ice water bath, adding an initiator into the obtained reaction system, adding a reducing agent into the reaction system in batches, heating the reaction system to 20-80 DEG C, and stirring the reaction system; and extracting the reaction system after the reaction is completed, drying the obtained organic phase, filtering the dried organic phase, and performing rotary drying to obtain a compound V that is the intermediate. The preparation method of the invention has the advantages of simplicity and mild reaction conditions, and can be widely applied to industrial production.

Practical and theoretical aspects of Wacker oxidation of tolanophanes: Synthesis and characterization of novel diketonic cyclophanes

Novel cyclophanes having 1,2-diketones 2a–c were synthesized by Wacker oxidation of the corresponding tolanophanes 1a–c having various alkyl chain lengths (n?=?2–4). Among them, tolanophane 1a with the shortest alkyl chain length (n?=?2) having more strained alkyne shows the lowest product selectivity even lower than that of acyclic analogues at various reaction temperatures. In contrast, the oxidation of tolanophane 1b (n?=?3) is clean with the highest activity and selectivity of 2b. Theoretical calculations confirm the experimental data. Based on ab initio calculations, the critical step of the reaction pathway is the interaction of oxygen atoms of 1 (in the absence of H2O) with Pd ion of intermediate [PdCl3(1)]? to give [PdCl2(1)] which keeps Pd ion close to the alkyne bond. This step is not observed computationally for 1a because the positions of the oxygen atoms are outside of its central part. This is in good agreement with almost no activity of 1a at room temperature to prove its rigid structure preventing the O…Pd interaction. Nevertheless, the alkyne…Pd interaction of 1b is not detected by NMR measurements which may be due to its too slow interaction at room temperature (35% after 24?h); however, this confirms ab initio calculation data that the preferred coordinating site is oxygen in the reaction pathway. In contrast, cyclic voltammetry measurements distinguish a different behaviour for the palladium complexation of 1. In general, it is found that the stereochemistry of tolanophanes rather than distortion of alkyne bond plays the critical role in the oxidation. The products are new and their structures were characterized.

Copper-catalyzed TEMPO oxidative cleavage of 1,3-diketones and β-keto esters for the synthesis of 1,2-diketones and α-keto esters

A copper-catalyzed efficient and practical method has been developed for the synthesis of 1,2-diketones and α-keto esters. TEMPO was used as a radical initiator and scavenger, oxidizing the cleavage of α-methylene of 1,3-diketones and β-keto esters to form 1,2-diketones and α-keto esters. This method provided a general way for the formation of 1,2-dicarbonyl compounds.

NaBrO3/bmim[HSO4]: a versatile system for the selective oxidation of 1,2-diols, α-hydroxyketones, and alcohols

Abstract: Sodium bromate with bmim[HSO4] has been found to be an excellent oxidizing agent in aqueous medium. NaBrO3:bmim[HSO4] oxidized 1,2-diols, α-hydroxyketones, and alcohols to the corresponding carbonyl compounds in excellent yields. This method offers advantages such as low cost reagents, aqueous reaction conditions, moderate temperatures and short reaction times and hence environmentally benign reaction. Moreover, the ionic liquid bmim[HSO4] could be recycled for at least three times without loss of significant activity. Graphical abstract: [Figure not available: see fulltext.]

Highly efficient asymmetric hydrogenation of cyano-substituted acrylate esters for synthesis of chiral γ-lactams and amino acids

A highly efficient and enantioselective synthesis of γ-lactams and γ-amino acids by Rh-catalyzed asymmetric hydrogenation has been developed. Using the Rh-(S,S)-f-spiroPhos complex, under mild conditions a wide range of 3-cyano acrylate esters including both E and Z-isomers and β-cyano-α-aryl-α,β-unsaturated ketones were first hydrogenated with excellent enantioselectivities (up to 98% ee) and high turnover numbers (TON up to 10 000).

A NOVEL QUINOXALINE COMPOUND FOR ULTRAVIOLET ABSORBERS

PURPOSE: A novel quinoxaline compound, isomer thereof, precursor drug thereof, or pharmaceutically acceptable salt thereof is provided to absorb UVA and UVB. CONSTITUTION: A quinoxaline compound is denoted by chemical formula 1. An UV absorber or pharmaceutical or cosmetic composition for antiaging contains the quinoxaline compound, isomer thereof, precursor drug thereof, or pharmaceutically acceptable salt, hydrate, or solvate thereof as an active ingredient.

Dendrimer-like core cross-linked micelle stabilized ultra-small gold nanoclusters as a robust catalyst for aerobic oxidation of α-hydroxy ketones in water

As one of the most general and promising stabilizers, dendrimers have been widely used to prepare ultra-small gold nanoclusters. However, the complex synthesis of dendrimers hinders the further application of protected nanoclusters. Here we report a facile strategy to prepare an alternative material via core cross-linking of self-assembled micelles. The resulting dendrimer-like core cross-linked micelles (DCCMs) retain the main characteristics of dendrimers and avoid complex chemical synthesis. As expected, the DCCMs could easily encapsulate gold nanoparticles within their cores. The ultra-small clusters of Au5 were prepared without the participation of external reductants. Importantly, the DCCM stabilized noble gold clusters furnish excellent catalytic activity and perfect reusability for aerobic oxidation of α-hydroxy ketones in water. Only in open air the oxidation could be repeated up to 48 times with negligible turn-over frequency change. The total turnover number (TON) of the reaction reached unexpectedly >48 000, the highest TON for metal catalysed oxidation of hydroxy ketones so far. The further mechanism study hints that the carboxylic group of substrates might be involved in the catalytic process. The simple catalyst preparation, the environmentally benign reaction conditions, and the excellent catalytic performance and durability make the novel DCCM protected gold nanocluster a green catalyst.

Preparation method of 1,2-diketone derivative

The invention discloses a preparation method of a 1,2-diketone derivative. The method comprises the step of enabling a raw material 1,3-diketone derivative to react with a cheap and easily obtained industrial product 2,2,6,6-tetramethyl-1-piperidinyloxy under the catalysis of copper so as to obtain the product 1,2-diketone derivative. According to the preparation method, the 1,3-diketone derivative is used as an initiator, and the raw material is easy to obtain and wide in variety; by utilizing the preparation method, the obtained product types are varied, can be directly used, and can be used for other further reactions; in addition, the reagent dosage in the reaction is less, the pollution is reduced, and the production cost is lowered; moreover the reaction conditions are mild, the reaction operation and the after-treatment process are simple, the reaction time is short, the yield is high, and the preparation method is suitable for industrial production.

Metal-Free [4+2] Annulation of Arylalkynes with tert-Butyl Nitrite through C(sp2)-H Oxidation to Assemble Benzo[e][1,2]oxazin-4-ones

A metal-free radical-mediated [4+2] annulation of internal arylalkynes with tert-butyl nitrite (t-BuONO) is presented for the synthesis of benzo[e][1,2]oxazin-4-ones through the addition of t-BuONO across the C-C triple bond, hydration, isomerization and aromatic C(sp2)-H oxidation cascades. The 18O-labeling experiment shows that two oxygen atoms in the product system are from water.

Synthesis of new chiral keto alcohols by baker's yeast

Fourteen chiral α- and β-keto alcohols 2a-2r were synthesized by the asymmetric reduction of their corresponding diketones 1a-1r via baker's yeast. In addition, ten corresponding racemic α-keto alcohols were synthesized by the benzoin condensation of their corresponding aldehydes, which were used for the determination of the ee values through their chiral resolution on chiral HPLC. Amongst the 15 diketones, 1j and chiral α-keto alcohols 2i, 2j and chiral β-keto alcohol 2r are novel compounds. Six keto alcohols 2b, 2c, 2d, 2f, 2h and 2p were synthesized by baker's yeast for the first time. There are some studies in the literature where baker's yeast was applied to the diketones 1a, 1g, 1e, 1k and 1n under various conditions different to those reported herein. The yields and the ee values of these studies were not as high as ours. All of the keto alcohols synthesized were characterized by IR, NMR (1H and 13C), and MS. The relationship between the structure of the diketone and the yield, diastereoselectivity and enantiomeric excess is also discussed.