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Beilstein Handbook : a Quick Guide


Overview

Beilstein portrait Beilsteins Handbuch der organischen Chemie is a comprehensive compilation of checked data on carbon compounds, drawn from the worldwide literature of organic chemistry.

Users of the electronic forms of Beilstein, including the MDL Crossfire system, may not be aware that the older data come from a classic printed handbook series. Using Beilstein in conjunction with Chemical Abstracts enables you to conduct a comprehensive retrospective search for literature and data about organic substances.

The 4th Edition was published in 503 volumes (over 440,000 pages) from 1918 to 1998, and covered the literature fairly comprehensively between 1779 and 1959. The Handbook is divided into a Basic Work (Hauptwerk, abbreviated H) and four Supplementary series (Ergänzungswerke, abbreviated E), each of which covers a specific period of literature. The Fifth Supplement covered only heterocyclic compounds in the literature from 1960-1979.

Series Abbreviation Vols. Literature Covered
Basic Work H 1-27 to 1909
1st Supplement E-I 1-27 1910-1919
2nd Supplement E-II 1-27 1920-1929
3rd Supplement E-III 1-16 1930-1939
4th Supplement E-IV 1-16 1940-1959
3/4 Supplement* E-III/IV 17-27 1930-1959
5th Supplement** E-V 17-27 1960-1979

* Volumes on Heterocyclics were combined into one series for these years.
** There are no print volumes on acyclic or isocyclic compounds after 1959. This information and post-1980 coverage can only be found in the database versions of Beilstein. The UT Chemistry Library stopped buying volumes of E-V after 1990.

Arrangement

Compounds in Beilstein are arranged according to the "Beilstein System," a complex series of rules which permits every substance to be assigned one specific location in the Handbook, based on its constitution and structure. Thus, every compound has a Volume Number and a System Number, which do not change over time. Once you know these, you can search for information in the same place in all Beilstein supplements. Compounds are divided into three broad categories:

Compound Type Volumes System Numbers
Acyclic (no ring) 1-4 1-449
Isocyclic (all-carbon ring(s)) 5-16 450-2358
Heterocyclic (other ring(s)) 17-27 2359-4720

Beilstein covers compounds of carbon with the following elements: 

          
          H
          Li  Be              B  C   N   O   F
          Na  Mg                 Si  P   S   Cl
          K   Ca                     As  Se  Br
          Rb  Sr                         Te  I
          Cs  Ba

Compounds excluded:

The Beilstein System is not easily summarized beyond this point--refer to the user guides and charts on the Index Table for further details.

Information on substances contained in the Handbook includes:

The data provided are always accompanied by references to the source documents.

The language of Beilstein through the 4th Supplement was German, for both text and compound names. Pertinent data can still be located by non-German readers however, and a small German-English chemical dictionary, useful for translating common terms and abbreviations, is located with the collection. The 5th Supplement is in English.

Location

Beilstein is shelved in the reference stacks, in the same area with Gmelin, Landolt-Börnstein, and Houben-Weyl. Red dividers mark the Basic Work and the Supplements. The volumes look a lot alike, so check the spines carefully to make sure you have the correct series.

Using the Beilstein Indexes

Beilstein's original indexes are divided into Formula (Formelregister) and Substance Name (Sachregister) sections. Three sets of indexes are now available:

Series covered Volumes covered Literature years covered
Basic Work, Suppls. 1-2 1-27 to 1929
Basic Work, Suppls. 1-4 1-27 to 1959
Suppl. 5 only 17-19 (incomplete) 1960-79

As a rule of thumb, use the formula indexes first, because name indexes use the German-language chemical nomenclature. The oldest index set is the best first stop, because all 27 volumes of the Basic Work and first two Supplements (H-EI-EII) are covered in a single listing. The H-EI-EIV indexes are divided by volume number, so unless you know the volume number in advance or can derive it from the System, it's less efficient to check these first. Once you do know the volume number for your compound, you can use the later indexes to locate Beilstein citations in the 3rd and 4th Supplements as well as in the earlier series. The indexes to the 5th Supplement are in English, and compound names adhere more closely to IUPAC standards.

(HELPFUL HINT: The CRC Handbook of Chemistry and Physics (older editions), the Handbook of Data on Organic Compounds, and the Aldrich Catalog serve as useful alternative indexes to Beilstein. Organic compound entries in these works include a Beilstein citation, which can lead you straight into the Handbook and provide a volume number for using the H-EI-EIV indexes.)

Below is a sample Formula index listing for the compound C26H43FN2O4 , from the Formelregister of Vols. 9-11. The third entry gives the German compound name and the Handbook citation. Information on this compound will be found in volume 9 of the 3rd Supplement, page 4245. The a next to the page number refers to the first entry on that page.


C26H43ClO3
 Cholan-24-säure, 3-Chlor-12-hydroxy-,
     äthylester   10 IV 792
C26H43Cl2NO
 Cholan-24-säure, 23,23-Dichlor-,
     äthylamid 9 IV 1994
C26H43FN2O4
 Isophthalsäure, 4-Fluor-, bis-
   [3-dipropylamino-propylester]
   9 III 4245 a
C26H43NO
 Eicos-11-ensäure, 2-Phenyl-, amid
   9 III 2921 b

Handbook Entries

Printed compound entries in Beilstein are brief and cryptic, and until the 5th Supplement they are in German. They begin with the German compound name, and later series also give an English systematic name next to it. The molecular formula in Hill order comes next, followed by a code (Formel) number referring you to the appropriate structure diagram nearby . The variable groups in the diagram are defined in the compound entry as X. Handbook data and/or synthesis information follows in the next paragraph--refer to the German dictionary for definitions of the abbreviations. The sample entry below shows a preparation (B.) method and the corresponding literature citation. (Beilstein's abbreviations of journal titles can be equally cryptic--a list can usually be found in the front of the volume.) It also gives the melting point (F) in Celsius.

At the top of every right-hand page are the Supplement and Volume numbers (9), the System Number, reference to the corresponding pages in the same volume number of the Basic Work, and the page number. 


E III 9                     Syst. Nr. 977 / H 836-837                     4245

4-Fluor-isophthalsäure, bis-[3-dipropylamino-propylester], 4-fluoroisophthalic acid
 bis[3-dipropylamino)propyl] ester  C26H43FN2O4, Formel II
(X = O-[CH2]3-N(CH2-CH2CH3)2).
  Dihydrochlorid C26H43FN2O4.2HCl.  B.  Aus 4-Fluor-isophthalsäure-dichlorid und 
3-Dipropylamino-propanol-(1) in Benzol (Fosdick, Calandra,  Am. Soc. 65 [1943] 2308). --
Krystalle (aus A. + Ae.); F: 110.

From here, older and newer series can be checked without further consultation of the indexes. Just use the volume number, System number, and Basic Work page number (H) to move back and forth in the Handbook supplements.

User Guides and Aids

These supporting materials are located near Beilstein:

Links

For further information about the online version of Beilstein, see the Crossfire page.