CHEM 324 - Using the Chemical Literature in an Organic Synthesis

There are common problems you may encounter when navigating the chemical literature:

• Not all of the information available on the over 30 million unique substances now registered with Chemical Abstracts Service (CAS) is found in one resource.
• A chemical can have many common names and tradenames. CAS has introduced Registry Numbers (unique identifiers) for substances, but not all publishers or commercial suppliers use these.
• Search engines are a great resource but it is difficult to navigate through the amount of information even an advanced search reveals. When you do find something it is not easy to judge whether a website is accurate and authoritative. You may find that you often have to pay for good chemical information on the Internet.

SciFinder-n is the most comprehensive resource for finding articles in chemistry with information on over 50 million substances and more than 18 million single- and multi-step reactions.

For finding synthesis information in SciFinder:

• Search for your compound by selecting the Advanced Search option and ensuring that the Substances tab is selected. Once you've found your compound, click on the "Get References" link (the icon that resembles a tiny book). Use the "Substance Role" limiter on the left-hand side of the screen to specify that you want references dealing with preparation of your compound;
  OR
• Search for your compound by selecting the Advanced Search option and ensuring that the Substances tab is selected. Once you've found your compound, click on the "Get Reactions" link (the icon that resembles an Erlenmeyer flask). Use the "Substance Role" limiter on the left-hand side of the screen to specify that you want references where your compound is a product of a reaction;

        OR

• Search for your compound by clicking on the Advanced Search option and ensuring that the References tab is selected. In the search box, type the following search string:

        (synthesis OR preparation) AND (name of your compound) 

        OR

• Search for your compound by using the search box on the main page of SciFinder to type "synthesis of" your compound name. Note that this search may use AI in an attempt to improve your search.

• ChemSpider: Locates chemical information from open access and commercial databases. It gives CAS Registry Numbers, synonyms, structures, and some properties (density, boiling point, melting point) for thousands of compounds.
• NIST Chemistry WebBook: Provides free access to chemical and physical property data of over 70,000 compounds. This database gives CAS Registry Numbers, synonyms, and structures and is an excellent source for finding spectral information.
• Organic Syntheses: This free resource provides detailed directions for the synthesis of organic compounds. Search all volumes of Organic Syntheses (from 1921 - today) simultaneously by keywords or structure.
• Methods in Organic Synthesis: Provides citations to reaction methods with a focus on current developments.

There is also a list of other databases you can try for literature searches.

Print sources give good summaries and provide physical property data, but can be hard to use. It is best to go to a database, such as SciFinder, to get the CAS-RN then go to a print source for more information.

The following reference books compiled the best data for the most often used chemicals:

• Dictionary of Organic Compounds : The entries will often include references to synthesis citations, alongside structure and physical property information.
• CRC Handbook of Chemistry and Physics: Contains a lot of information, including Physical Constants of Organic Compounds, and conversion tables. It also has definitions and nomenclature information.
• Merck Index: An Encyclopedia of Chemicals, Drugs and Biologicals: Provides data and related references for compounds having pharmacological properties. The Merck Index gives a good overview for each compound, some property data, and medical as well as non-medical uses of the compound.