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Dibenzoyloxyiodobenzene, also known as DBOB, is a chemical compound with the formula C20H15IO4. It is a hypervalent iodine reagent used in organic synthesis, particularly for the oxidation of alcohols to aldehydes or ketones. DBOB is a colorless solid that is soluble in organic solvents. It is synthesized by the reaction of benzene with dibenzoyl peroxide and iodine. The compound is known for its ability to selectively oxidize primary and secondary alcohols without over-oxidation to carboxylic acids, making it a valuable tool in the synthesis of complex organic molecules. DBOB is also recognized for its mild reaction conditions and high yields, which contribute to its utility in various chemical transformations.

6597-18-8

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6597-18-8 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 6597-18-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,5,9 and 7 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 6597-18:
(6*6)+(5*5)+(4*9)+(3*7)+(2*1)+(1*8)=128
128 % 10 = 8
So 6597-18-8 is a valid CAS Registry Number.

6597-18-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name PhI(O2CPh)2

1.2 Other means of identification

Product number -
Other names PhI(OCOPh)2

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6597-18-8 SDS

6597-18-8Relevant academic research and scientific papers

Remote Substituents as Potential Control Elements for the Solid-State Structures of Hypervalent Iodine(III) Compounds

Li, Guobi,Rheingold, Arnold L.,Protasiewicz, John D.

supporting information, p. 7865 - 7875 (2021/05/26)

Hypervalent iodine (HVI) compounds are very important selective oxidants often employed in organic syntheses. Most HVI compounds are strongly associated in the solid state involving interactions between the electropositive iodine centers and nearby electr

An Efficient Approach to Functionalized Indoles from λ3-Iodanes via Acyloxylation and Acyl Transfer

Jeyakannu, Palaniraja,Chandru Senadi, Gopal,Chiang, Chun-Hsien,Kumar Dhandabani, Ganesh,Chang, Yu-Ching,Wang, Jeh-Jeng

supporting information, p. 2911 - 2920 (2020/06/02)

Versatile role of λ3-iodanes has been identified between the reaction of hydroquinone and β-enaminones for the synthesis of 5-acyloxy-4-hydroxy indoles. The reaction is proposed to proceed through an intermolecular C?C bond formation, intramole

Method for producing hypervalent iodine compound

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Paragraph 0063-0064, (2020/12/31)

The invention provides a method for producing a hypervalent iodine compound; the method is more effective than the prior art, improves yield while reducing reaction time, and is more suitable for industrial application.

λ3-Iodanes as Visible Light Photocatalyst in Thioacetalization of Aldehydes

Choudhuri, Khokan,Pramanik, Milan,Mal, Prasenjit

supporting information, p. 4822 - 4826 (2019/07/31)

Introduction of an iodine(III) reagent as visible-light photocatalyst for chemoselective dithioacetalization has been the limelight of the current methodology. The mechanistic investigations reveal that the reactions proceeded via radical pathway upon lig

A trivalent hypervalent iodine compound using hypochlorite (by machine translation)

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Paragraph 0060, (2020/02/14)

[A] used in the prior art organic salt, toxic chlorine gas, organic peroxides can be used without the novel trivalent hypervalent iodine compound production. Furthermore, the acyloxy groups other than the trivalent hypervalent iodine compounds having a ligand manufacturing method. (1) Formula [solution](In the formula, R1 Substituted/unsubstituted aromatic group, aliphatic group or the like. N is an integer of 1 or more. ) Represented by the iodine compound, carboxylic acid, carboxylic acid anhydride, a sulfonic acid or sulfonic acid anhydride with at least one organic acid selected from the group consisting of, a hypochlorite mixing, trivalent hypervalent iodine compound. [Drawing] no (by machine translation)

Iodosylbenzene Coordination Chemistry Relevant to Metal-Organic Framework Catalysis

Cardenal, Ashley D.,Maity, Asim,Gao, Wen-Yang,Ashirov, Rahym,Hyun, Sung-Min,Powers, David C.

supporting information, p. 10543 - 10553 (2019/09/13)

Hypervalent iodine compounds formally feature expanded valence shells at iodine. These reagents are broadly used in synthetic chemistry due to the ability to participate in well-defined oxidation-reduction processes and because the ligand-exchange chemist

Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature

Fan, Huaqiang,Pan, Peng,Zhang, Yongqiang,Wang, Wei

supporting information, p. 7929 - 7932 (2019/01/04)

A hypervalent iodine(III)-mediated intramolecular decarboxylative Heck-type reaction of 2-vinyl-phenyl oxamic acids has been developed. The unique ring-strain-enabled radical decarboxylation mechanism is preliminarily revealed. This protocol features metal-free reaction conditions and operational simplicity, allowing the lactamization of 2-vinylanilines using a readily accessible carbonyl source and the synthesis of various 2-quinolinones with excellent chemoselectivity at room temperature.

Oxidase catalysis via aerobically generated hypervalent iodine intermediates

Maity, Asim,Hyun, Sung-Min,Powers, David C.

, p. 200 - 204 (2018/02/06)

The development of sustainable oxidation chemistry demands strategies to harness O'2 as a terminal oxidant. Oxidase catalysis, in which O'2 serves as a chemical oxidant without necessitating incorporation of oxygen into reaction products, would allow diverse substrate functionalization chemistry to be coupled to O'2 reduction. Direct O'2 utilization suffers from intrinsic challenges imposed by the triplet ground state of O'2 and the disparate electron inventories of four-electron O'2 reduction and two-electron substrate oxidation. Here, we generate hypervalent iodine reagents - a broadly useful class of selective two-electron oxidants - from O'2. This is achieved by intercepting reactive intermediates of aldehyde autoxidation to aerobically generate hypervalent iodine reagents for a broad array of substrate oxidation reactions. The use of aryl iodides as mediators of aerobic oxidation underpins an oxidase catalysis platform that couples substrate oxidation directly to O'2 reduction. We anticipate that aerobically generated hypervalent iodine reagents will expand the scope of aerobic oxidation chemistry in chemical synthesis.

Preparation method and device for iodobenzene dibenzoate derivative

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Paragraph 0020; 0021; 0022; 0023, (2017/02/09)

The invention relates to a preparation method and device for an iodobenzene dibenzoate derivative. The method includes the steps that 6 mmol of iodobenzene diacetate and 12 mmol of benzoic acid or a benzoic acid derivative or pivalic acid are added into a

Synthesis of secondary amides from N-Substituted amidines by tandem oxidative rearrangement and isocyanate elimination

Debnath, Pradip,Baeten, Mattijs,Lefvre, Nicolas,Van Daele, Stijn,Maes, Bert U. W.

, p. 197 - 209 (2015/03/03)

In this work an efficient tandem process transforming N-substituted amidines into secondary amides has been described. The process involves N-acylurea formation by reaction of the substrate with bis(acyloxy)(phenyl)-λ3-iodane followed by isocyanate elimination. The periodinane reagents are obtained from the commercially available phenyl-iodine(III) diacetate [PhI(OAc)2, (PIDA)] by ligand exchange with carboxylic acids. The N-substituted amidine substrates are easily synthesized from readily available nitriles. The method is applicable for secondary amide synthesis, based on both aliphatic and (hetero)aromatic amines, including challenging amides consisting of sterically hindered acids and amines. Moreover, the protocol allows one to combine steric bulk with electron deficiency in the target amides (aniline based). Such compounds are difficult to synthesize efficiently based on classical condensation reactions involving carboxylic acids and amines. Overall, the synthetic protocol transforms a nitrile into a secondary amide in both aliphatic and (hetero)aromatic systems.

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