[Skip to Content](https://www.sigmaaldrich.com#main-content) [](https://www.sigmaaldrich.com/US/en) Products Cart0 USEN Products [Login / Register](https://www.sigmaaldrich.com/oidc-sign-in) [Order Lookup](https://www.sigmaaldrich.com/US/en/order-lookup) [Quick Order](https://www.sigmaaldrich.com/US/en/quick-order) Cart0 [Home](https://www.sigmaaldrich.com/US/en)[Applications](https://www.sigmaaldrich.com/US/en/applications)[Chemistry & Synthesis](https://www.sigmaaldrich.com/US/en/applications/chemistry-and-synthesis)[Synthetic Methods](https://www.sigmaaldrich.com/US/en/applications/chemistry-and-synthesis/synthetic-methods)Organic Reaction Toolbox # Organic Reaction Toolbox  An organic reaction toolbox is a way to organize useful chemical reactions needed for solving synthetic problems and developing new small molecules. When creating a synthetic pathway, a chemist utilizes numerous reactions to transfer one small molecule into a new one. By using protecting groups and creating molecular complexity more directly, detours to pathways can be avoided. Typically, these reactions are characterized into three broad buckets which determine how the reactants combine to form other products. The first bucket focuses on the predictable reaction characteristics of the 19 main functional groups (alkane, alkene, alkyne, alkyl halide, alcohol, ether, thiol, sulfide, ketone, aldehyde, carboxylic acid, ester, acyl halide, acid anhydride, amide, amine, nitrile, epoxide, and aryl). These characteristics determine the reactivity properties when present on a molecule. By focusing on the reactions that can be used for a specific functional group, a scientist limits the reaction options to those plausible for the desired transformation. * * * ## Related Products Slide 1 of 20 1 of 5 [ \ Sigma-Aldrich \ 901907 \ RuPhos](https://www.sigmaaldrich.com/US/en/product/aldrich/901907) Quick View [ \ Sigma-Aldrich \ 718742 \ BrettPhos](https://www.sigmaaldrich.com/US/en/product/aldrich/718742) Quick View [ \ Sigma-Aldrich \ 719439 \ XtalFluor-E®](https://www.sigmaaldrich.com/US/en/product/aldrich/719439) Quick View [ \ Sigma-Aldrich \ 719447 \ XtalFluor-M®](https://www.sigmaaldrich.com/US/en/product/aldrich/719447) Quick View [ \ Sigma-Aldrich \ 795291 \ Phenofluor™ solution](https://www.sigmaaldrich.com/US/en/product/aldrich/795291) Quick View [ \ Sigma-Aldrich \ 797537 \ PhenoFluor™ Mix](https://www.sigmaaldrich.com/US/en/product/aldrich/797537) Quick View [ \ Sigma-Aldrich \ 900456 \ AlkylFluor](https://www.sigmaaldrich.com/US/en/product/aldrich/900456) Quick View [ \ Sigma-Aldrich \ 777692 \ (1,10-Phenanthroline)(trifluoromethyl)copper(I)](https://www.sigmaaldrich.com/US/en/product/aldrich/777692) Quick View [![Ir\[p-F(t-Bu)-ppy\]3](https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/structures/189/186/7badaac3-82af-4109-aab5-dea3a3aa916d/640/7badaac3-82af-4109-aab5-dea3a3aa916d.png) \ Sigma-Aldrich \ 900539 \ Ir\[*p*-F(t-Bu)-ppy\]3](https://www.sigmaaldrich.com/US/en/product/aldrich/900539) Quick View [ \ Sigma-Aldrich \ 904694 \ Ir(p-CF3-ppy)3](https://www.sigmaaldrich.com/US/en/product/aldrich/904694) Quick View [![\[Ir(dFCF3ppy)2-(5,5’-dCF3bpy)\]PF6 ≥95%](https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/structures/422/901/e00f3148-fb86-4f94-9e79-21d064c3f327/640/e00f3148-fb86-4f94-9e79-21d064c3f327.png) \ Sigma-Aldrich \ 908568 \ \[Ir(dFCF3ppy)2-(5,5′-dCF3bpy)\]PF6](https://www.sigmaaldrich.com/US/en/product/aldrich/908568) Quick View [![\[Ir(dFOMeppy)2-(5,5′-dCF3bpy)\]PF6 ≥95%](https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/structures/401/909/9c746f9e-e2f3-41bc-94d2-6ef5c913fcc5/640/9c746f9e-e2f3-41bc-94d2-6ef5c913fcc5.png) \ Sigma-Aldrich \ 911607 \ \[Ir(dFOMeppy)2-(5,5′-dCF3bpy)\]PF6](https://www.sigmaaldrich.com/US/en/product/aldrich/911607) Quick View [![Ir\[FCF3(CF3)ppy\]2(dtbbpy)PF6](https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/structures/378/510/56b6b674-c8d0-4647-8683-91484e1b7543/640/56b6b674-c8d0-4647-8683-91484e1b7543.png) \ Sigma-Aldrich \ 912948 \ Ir\[FCF3(CF3)ppy\]2(dtbbpy)PF6](https://www.sigmaaldrich.com/US/en/product/aldrich/912948) Quick View [![\[Ru(phen)3\]Cl2 ≥95%](https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/structures/955/596/46f63eaa-39f8-4058-847d-cef0862ada92/640/46f63eaa-39f8-4058-847d-cef0862ada92.png) \ Sigma-Aldrich \ 904767 \ \[Ru(phen)3\]Cl2](https://www.sigmaaldrich.com/US/en/product/aldrich/904767) Quick View [2 ≥95%](https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/structures/238/198/d2398f4d-117e-4482-8d8b-80ae657f6ea1/640/d2398f4d-117e-4482-8d8b-80ae657f6ea1.png) \ Sigma-Aldrich \ 904953 \ \[Ru(dtbbpy)3\](PF6)2](https://www.sigmaaldrich.com/US/en/product/aldrich/904953) Quick View [ \ Sigma-Aldrich \ 903426 \ Ru(*p*-CF3-bpy)3 (BF4)2](https://www.sigmaaldrich.com/US/en/product/aldrich/903426) Quick View [ \ Sigma-Aldrich \ 912255 \ sBOX(*t*Bu)](https://www.sigmaaldrich.com/US/en/product/aldrich/912255) Quick View [ \ Sigma-Aldrich \ 912883 \ tBuBrettPhos Pd G6 TES](https://www.sigmaaldrich.com/US/en/product/aldrich/912883) Quick View [ \ Sigma-Aldrich \ 905313 \ Rh2(*S*-TCPTAD)4](https://www.sigmaaldrich.com/US/en/product/aldrich/905313) Quick View [![Ir\[p-F(t-Bu)-ppy\]3](https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/structures/189/186/7badaac3-82af-4109-aab5-dea3a3aa916d/640/7badaac3-82af-4109-aab5-dea3a3aa916d.png) \ Sigma-Aldrich \ 900539 \ Ir\[*p*-F(t-Bu)-ppy\]3](https://www.sigmaaldrich.com/US/en/product/aldrich/900539) Quick View * * * ## Featured Categories [](https://www.sigmaaldrich.com/US/en/products/analytical-chemistry/reference-materials/certified-reference-materials) [Buchwald Catalysts & Ligands](https://www.sigmaaldrich.com/US/en/products/analytical-chemistry/reference-materials/certified-reference-materials) Buchwald Catalysts and Ligands are highly active and versatile palladium precatalysts and biarylphosphine ligands used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. 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For example, if an alcohol is the desired end functional group, one could look at using a Grignard reaction with an aldehyde or a ketone, a reduction reaction of either a carboxylic acid, an aldehyde, a ketone, or an ester, or a hydration reaction of an alkene. The third type of reaction group focuses on reactions that alter the carbon-carbon skeleton through bond creation or breaking. Tremendous advances in synthetic methods for C-C bond formation now make it possible to choose from over 100 different reactions. These advances are due to various factors, including the development of robust and reliable protocols for cross-coupling, increased accessibility to various organometallic reagents, and the creation and improvement of stoichiometric reagents which serve to place a specific carbon-containing moiety. [](https://www.sigmaaldrich.com/documents-search) [Looking for More Specific Information?](https://www.sigmaaldrich.com/documents-search) Visit our document search for data sheets, certificates and technical documentation. [Find Documents](https://www.sigmaaldrich.com/documents-search) ## Related Articles - [Acid and Base Chart — Table of Acids & Bases](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/acid-base-chart) Acid and base chart lists the strength of acids and bases (strongest to weakest) in order. Simple to use laboratory reference chart for scientists, researchers and lab technicians. - [Aldol Condensation Reaction](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/organic-reaction-toolbox/aldol-condensation-reaction) The aldol condensation reaction is an organic reaction introduced by Charles Wurtz, who first prepared the β-hydroxy aldehyde from acetaldehdye in 1872. - [Baeyer-Villiger Oxidation Reaction](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/organic-reaction-toolbox/baeyer-villiger-oxidation-reaction) The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts the ketones to esters and the cyclic ketones to lactones. - [1-hydrosilatrane](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/organic-reaction-toolbox/1-hydrosilatrane) As a versatile hydride reagent, 1-hydrosilatrane can be used in reduction reactions to synthesize alcohols, amines, their chiral counterparts, and esters from aldehydes/ketones. - [Role of High Purity Metal Salts in Chemical Synthesis](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/ch-functionalization/role-of-high-purity-metal-salts-in-chemical-synthesis) Discover the ways in which high-purity metal salts improve the selectivity, yields, and catalytic efficacy of organic synthesis reactions. - [See All (32)](https://www.sigmaaldrich.com/US/en/search/facet-search?focus=sitecontent&term=facet-search) ## Related Protocols - [Ampule Opener from Bel-Art](https://www.sigmaaldrich.com/US/en/technical-documents/protocol/chemistry-and-synthesis/organic-reaction-toolbox/bel-art-ampule-opener) Scienceware® Break-Safe™ ampule opener ### Find More Articles and Protocols Enter Keywords Search ## How Can We Help In case of any questions, please submit a [customer support request](https://www.sigmaaldrich.com/US/en/support/customer-support) or talk to our customer service team: Email [[email protected]](mailto:[email protected]) or call +1 (800) 244-1173 ## Additional Support - [Chromatogram Search](https://www.sigmaaldrich.com/chromatogram-search) Use the Chromatogram Search to identify unknown compounds in your sample. - [Calculators & Apps](https://www.sigmaaldrich.com/US/en/support/calculators-and-apps) Web Toolbox - science research tools and resources for analytical chemistry, life science, chemical synthesis and materials science. - [Customer Support Request](https://www.sigmaaldrich.com/US/en/support/customer-support) Customer support including help with orders, products, accounts, and website technical issues. - [FAQ](https://maestro.my.site.com/knowledgeportal/s/) Explore our Frequently Asked Questions for answers to commonly asked questions about our products and services. * * * __Featured Articles__ [Acid and Base Chart — Table of Acids & Bases](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/acid-base-chart) Acid and base chart lists the strength of acids and bases (strongest to weakest) in order. Simple to use laboratory reference chart for scientists, researchers and lab technicians. [Aldol Condensation Reaction](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/organic-reaction-toolbox/aldol-condensation-reaction) The aldol condensation reaction is an organic reaction introduced by Charles Wurtz, who first prepared the β-hydroxy aldehyde from acetaldehdye in 1872. [Baeyer-Villiger Oxidation Reaction](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/organic-reaction-toolbox/baeyer-villiger-oxidation-reaction) The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts the ketones to esters and the cyclic ketones to lactones. [1-hydrosilatrane](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/organic-reaction-toolbox/1-hydrosilatrane) As a versatile hydride reagent, 1-hydrosilatrane can be used in reduction reactions to synthesize alcohols, amines, their chiral counterparts, and esters from aldehydes/ketones. Top __Sign In To Continue__ To continue reading please sign in or create an account. Sign In__Don't Have An Account?__Register An unknown error has occured. - English - EN - Español - ES [Learn More](https://www.sigmaaldrich.com)