Cheatsheet for finding derivatives

Guidelines for making derivatives

Consult Guidelines for Making Derivatives to help decide what derivative to make.

The Guidelines are available on the web and in your course reader. Both printed and electronic resources are available for synthesizing derivatives. See Swain’s Derivatives Bibliography page for a list of resources.

Below are search methods you can use to help find physical property information and synthesis information for your derivative in CCD and in Beilstein Crossfire. Note that the type of information compiled for compounds varies considerably, so you may need to use several resources and/or several different search strategies. See the Finding Derivatives Lecture for an overview of the process and a pictorial guide to using CCD and Beilstein Crossfire to find derivatives. Below is a brief summary of the common search techniques you may need to use in CCD or in Beilstein Crossfire:

Search The Combined Chemical Dictionary (CCD) first

Do CAS Registry Number or chemical name search.
View derivatives information in search results. Consult original sources for synthesis information.
If the derivative you want to make is not listed or if your parent compound is listed as a derivative in CCD, then search Beilstein.

Search Beilstein if you do not find information you need in CCD

Do CAS Registry Number search and view derivative field in record of parent compound.
If your derivative is not listed, then do a chemical reaction search specifying your parent compound as a reactant and your derivative as a product.
If you get zero results, omit reactant and rerun search.
If you still get zero results, perform a chemical substance search on the product or derivative you want to make. Consult with Library TAs or Librarians for assistance.

Detailed search strategy instructions for finding derivatives

Search The Combined Chemical Dictionary (CCD) first

Because the CCD includes derivatives containing common functional groups, consult CCD first.

Search CAS Registry Number or chemical name of your parent compound.

If your parent compound is listed as a main entry in CCD (first compound given in an record)

Determine if the derivative you want to make is listed in CCD. If it is listed, note physical properties. Read the bibliography at the end of the entry. References may be annotated with either “deriv” or “synth.” You may need to consult original sources to find out which derivatives are listed within a particular source.

If your parent compound is listed as a derivative in CCD

Search Beilstein if your parent compound is listed as a derivative in CCD or to find more information on your derivative.

Search Beilstein if you do not find information you need in CCD

Beilstein contains 8 million compounds and 5 million reactions and is the most comprehensive source for information on derivatives. However, because Beilstein defines chemical derivatives more narrowly than is done in Chem 130/132, the information you need may be in the substance record of the derivative you want to synthesize.

Search CAS Registry Number for your unknown parent compound

Do a CAS Registry Number search in Beilstein. Place the cursor in the lower left window and type RN= followed by the CAS Registry Number, retaining the hyphens (e.g. RN=50-00-0). Next, click the Start Search button.

Review results to see if/what information is compiled on derivatives: Go to View menu bar. If results include more than one item, choose Short Display to view results. Double click on box containing compound of interest. Go to View menu bar and select All Fields. Return to View menu bar and select FieldAvailability. A small window will open containing a list of all the types of data compiled in this record. Click once in Alphabetical by Name and then scroll through the list to see if Derivatives is listed. If Derivatives is listed, double click on the word Derivatives to see what derivative information is compiled.

Derivative Entries in the Derivative Field: Chemical name, melting point or boiling point, and a reference on how to synthesize a derivative is usually included in each Derivative Entry. The same derivative may be listed more than once if experimental conditions are different. Consult original reference for information on how to synthesize derivative. Consult a Library TA or Swain staff if you need help interpreting literature references.

A substance record in Beilstein may be very long (e.g. 1000 pages)! So you need to define your display format so that it contains only the fields you want to print. To create a user-defined display format, go to the Options menu bar and select Define User View. Click on New to define a new display. Next press the Remove All button if there is anything listed in the window on the right side. Highlight and copy the Substance and the Bibliographic Information into the window on the right side of the screen. They contain the substance identification information and literature references for data reported in other fields of the record. Use the Find button to locate folder(s) containing other data you want to display. Copy the highlighted field to the window on the right hand side of the screen. After defining all the fields you want to include in your display format, press OK and then save your display format. Close the User Views screen. Once your user view is defined, the next step is to select your user view. Go to the View menu bar, scroll down to User View and select your named user view. Once the user defined view has loaded, then hit the print button.

If your derivative is not included in record of parent compound, then do a chemical reaction search by drawing both the reactant (your parent compound) and the product (derivative you want to make)

From Beilstein Commander (opening view), double click on large window to go into Structure Editor. Go to Options menu bar, select Molecule View, and for Atom View choose C As Dot so that you will not inadvertently superimpose to atoms on one another. Now use ring, atom, and bond choices to draw structure. Hold down shift key when changing atom or bond value. Unless specified, all open positions are assumed to be saturated with Hydrogens. (If you want to allow further substitution at a particular position on the structure, click on atom at that positions and set the Free Sites value.)

To use predrawn templates, go to File command, select Templates, select Template file of interest (e.g. Residues for shortcuts), and then click on Template icon that is to the immediate left of the ring icons (looks like a small grid). Double click on item of choice to use in structure. If you need to reorient a structural fragment, use the Highlighter and Rotator (looks like a circle) tools. Note that functional groups are drawn in a neutral state (or without a charge) in Beilstein (e.g. NO₂ — both bonds to the Oxygens are double bonds).

After you have finished drawing your structure(s), go to the Editmode menu bar and choose Reaction. Use Highlighter tool (tool below pencil) to draw a box around the structure. Next, click on the Product button to designate the structure as a reactant or product of a reaction. Click ->BC and press the Start button.

View results in Short Display format. Double click on record of interest. Scroll through reactions listed. Double click on Reaction ID hypertext links to see reaction details, e.g. the reaction using different solvents.

If you get zero results from your reaction search, rerun it again but only specify the product.

Go into Structure Editor, highlight reactant and then choose Cut from Edit bar menu. Click ->BC and press Start button to rerun search. Other search options to locate derivatives include doing a structure search on the product you want to make. Under View menu bar, select Reaction View and then Substance as a Product.

If you are spending a long time looking for a derivative or if all of the above methods fail, please ask for help.