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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.

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:

  • CO, CS, CO2, CS2, COS, C3O2, C3S2
  • Carbonic acid and its thio analogs along with their salts with inorganic cations
  • HCN, HOCN, HSCN and the corresponding iso-acids and all the metal salts and complexes of these acids
  • Dicyanogene, Phosgene
  • Metal salts of formic acid, acetic acid, and oxalic acid
  • Peptides with >13 amino acids
  • Polymers

The Beilstein System of classification is not easily summarized beyond this point - refer to the accompanying user guides and charts for further details.

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.

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:

  • constitution and structure
  • physical and chemical properties
  • occurence and isolation
  • characterization and analysis
  • preparation and purification
  • salts and addition compounds
  • structural and energy parameters

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

Location

The Beilstein Handbook is located in the Chemistry Reference Collection.

User Guides and Aids

These supporting materials are located near Beilstein:

  • Beilstein Dictionary (German -- English) - essential for deciphering German abbreviations and terms in the text
  • Beilstein's Index: Trivial Names in Systematic Nomenclature of Organic Chemistry.
  • Contents of Beilstein: Representative Examples.
  • How to Use Beilstein.
  • A Programmed Guide to Beilstein's Handbuch. (1966)
  • Stereochemical Descriptors in the Beilstein Handbook.
  • Patterson's German-English Chemical Dictionary.

Some frequently used textual abbreviations:

  • B. = Bildung = how to make
  • Band = volume
  • D = density
  • Dritter/s = third
  • Erster = first
  • F = melting point
  • Funfter = fifth
  • Kp = boiling point
  • S. = Seite = page
  • Teil = part
  • Vierter = fourth
  • Zweiter = second

Links

Friedrich BeilsteinBeilstein is a name known to millions of chemists, thanks to the ongoing popularity of his seminal Handbuch and later the database derived from it, but few people remember anything about the man himself. No English-language biography has ever been published.

Friedrich Konrad Beilstein was born to German parents in St. Petersburg, Russia, on February 5, 1838. He was educated in St. Petersburg, and went to Germany for further study at the age of 15. His education in chemistry was taken with illustrious mentors such as Robert Bunsen in Heidelberg, Justus von Liebig in Munich, and August Kekulé. He earned his doctorate with Friedrich Wöhler at Göttingen in 1858 at the age of 20. From there he worked with Adolphe Wurtz in Paris, and in 1860 he returned to Göttingen to work in Wöhler's laboratory. There he built a reputation as an excellent teacher.

In 1866 Beilstein took a position as Mendeleev's successor at the Technological Institute in St. Petersburg, and later became a Russian subject. There he primarily taught analytical chemistry and authored an important textbook, Anleitung zur qualitativen chemischen Analyse, which went through several editions and was translated into several other languages, including an English version by William Ramsay. Although personal conflicts with Mendeleev and other Russian chemists over the next 15 years damaged his career, Beilstein remained in St. Petersburg for the rest of his life.

In the late 1870s Beilstein set out to write a textbook for organic chemistry based on material he had been compiling for over a decade, but as he proceeded it began to evolve into a reference work on all known organic compounds. In an 1878 letter to Erlenmeyer, Beilstein laid out his vision for the book: "I want to put together in one volume the complete material of org. chemistry ordered completely and clearly with exact information about the literature. Pretty speeches, charming comparisons, lively pictures and the rest of it are as good as completely absent" (quoted in Gordin). His obsession with thoroughness and accuracy required him to read, annotate and recheck every article in the entire organic chemistry literature, a daunting task even in 1880. He nevertheless did this work without any significant assistance.

The Handbuch der organischen Chemie was published in German in two volumes in 1881-83. It contained 2200 pages and 15,000 organic compounds. It was well received among chemists, who called it indispensible. H.C. Bolton, in his Select Bibliography of Chemistry, (Washington DC: Smithsonian, 1893) annotated it simply as "a stupendous monument of industrious, intelligent compilation." Beilstein immediately began to work, alone, on a second edition: the first volume appeared in 1885 and the third volume in 1889. For the third edition Beilstein took on an assistant editor, and the four-volume set was published starting in 1899. Supplements and an index brought it to eight volumes by 1906.

Beilstein's death in 1906 was barely noted in Russian circles. The nationalist prejudices of that era (against which Beilstein himself, as a German living in Russia, fought unsuccessfully later in life) were splintering the scientific establishment, condemning the handbook pioneer to almost immediate obscurity even as his Handbuch continued to grow and flourish. Editorial operations moved to Germany where it was produced thereafter by the German Chemical Society. In 1909 the editors adopted a new system of categorizing all organic compounds, the Beilstein System. In 1918, as World War I was ending, Springer-Verlag began publication of the monumental Fourth Edition of the Handbuch, which would stretch over 80 years, five supplementary series, and 500 volumes.

Although the later incarnation of the Handbuch was far larger than Beilstein's own versions, it remained true to his vision of comprehensive, reliable coverage of the organic literature for decades to come. Eventually, however, the sheer enormity of the chemical literature rendered such perfection impossible, and the Handbuch began to lag behind the literature, especially during and after the disruptions caused by World War II. The 4th Supplement covering the literature through 1959 was not fully completed until 1987. The 5th Supplement, now in English, essentially abandoned the idea of comprehensiveness and settled for a voluminous but more selective coverage of heterocyclic literature between 1960 and 1979. It finally ceased publication in print in 1998, nearly twenty years after its literature closing date and long after most libraries had given up on it as a grossly expensive dinosaur. Beilstein's concept had served well for over a century, but clearly new ideas were needed.

Fortunately, Beilstein's work was resurrected by the digital medium, and eventually the Internet. The Beilstein Institute began migrating the Handbuch to a database format in the 1980s, and produced fee-based versions on STN and Dialog, then CD-ROM subsets, before partnering with MDL and Elsevier in the 1990s to produce an Internet-based client-server system called Beilstein Crossfire. Elsevier later purchased the system outright and launched its web-based successor Reaxys in 2010. This database, containing data on millions of compounds and reactions, is a monumental work in itself. Sadly, the Institute no longer has any connection to the work launched by its namesake over 130 years ago, and Beilstein's name has been erased from it entirely due to licensing disputes.


Bibliography

Gordin, Michael D. "Beilstein unbound: unraveling the Handbuch der organischen Chemie." Chemical Heritage, 21(4) 2003/4, 10-11, 32-36.

Gordin, Michael D. "Beilstein unbound: the pedagogical unraveling of a man and his Handbuch." in Kaiser, David, ed., Pedagogy and the practice of science: historical and contemporary perspectives. (MIT Press, 2005) 11-39.

Gordin, Michael D. Scientific Babel: how science was done before and after global English. (Univ. of Chicago Press, 2015), 283-291.

Hjelt. [Obituary] Chemische Berichte, 40 (1907) 5041-78.

Huntress, E.H. "1938: the one hundredth anniversary of the birth of Friedrich Konrad Beilstein." Journal of Chemical Education, 15 (1938) 303-9.

Luckenbach, R. "The Beilstein Handbook of Organic Chemistry: the first hundred years." Journal of Chemical Information and Computer Science, 21 (1981) 82-83.

[Obituary] Journal of the Chemical Society, 99 (1911) 1646-49.

Richter, F. "How Beilstein is made." Journal of Chemical Education, 15 (1938) 310-16.

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