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Beilstein portrait The Beilstein Handbook



Beilsteins Handbuch der organischen Chemie is a compilation of checked information on carbon compounds drawn from the journal and patent literature. The 4th Edition was published in 503 volumes (over 440,000 pages) from 1918 to 1998, and covered the literature on organic chemistry fairly comprehensively up to 1959, and then more selectively for heterocyclic compounds up to 1979. Most factual data from the Beilstein Handbook through 1959 is included in the Reaxys database.


Arrangement

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 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 through 1959. The Fifth Supplement (E-V) covered only selected 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.
** The 5th Supplement was published in English. (The Chemistry Library stopped buying new volumes after 1990.) This Supplement has only partially been converted to the database version. No literature from 1980 onward was ever covered in the printed Beilstein.

Compounds are arranged according to the "Beilstein System," a complex series of rules which permit 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 of the handbook's parts. 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 of classification is not easily summarized beyond this point - refer to the accompanying user guides and charts for further details.


Interpreting a Beilstein Reference

Modern chemists will often not encounter Beilstein until they run across a reference to the Handbuch in some other publication, such as an older CRC Handbook or the Aldrich Catalog. These cryptic references usually look like this:
  Beil. 13,III,2311
  Beil. 133, 2311
which is just shorthand for an entry found in volume 13 of the 3rd Supplement, on page 2311.


Using the Beilstein Indexes

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

Use the formula indexes first, because name indexes use German-language 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. (* See TIP below.) 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.

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


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


Handbook Entries

Entries in Beilstein are highly abbreviated, and until the 5th Supplement they were in German. They begin with the German compound name, and later series also give an English systematic name. The molecular formula in Hill order comes next, followed by a code (Formel) referring to the appropriate structure diagram. 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.

Information on substances contained in the Handbook includes:

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


User Guides and Aids

These supporting materials are located near Beilstein:

Some frequently used textual abbreviations:

Links