Teaching Chemical Information:
Tips and Techniques

— August 1998 —

Chemical Literature (Chem 184/284)
University of California at Santa Barbara

Assignment 1 Answers(Sample): Data Collections

The examples below do not include print sources not listed in the lecture notes, since there are a vast number of possibilities for each, but do cover all the relevant sources from the notes.

Compound 1: Sodium tetracarbonylferrate(-2)		CAS Registry #: 14878-31-0
Source (full name)	Vol. #	Page(s)	Types of information given
Aldrich Catalog 1996/97	N.A.	page 633, #22,549-5, listed under “Disodium tetracarbonylferrate, compound with 1,4-dioxane (1.1.5)”	Note that the Registry Number given here is for the dioxane adduct (59733-73-2). Gives the additional name, “Collman's Reagent”. Gives references to Fieser and the Aldrich Handbook of Safety Data as well as to literature references on the organic synthetic uses of the compound.
Dictionary of Inorganic Compounds	Vol. 1	p. 632, compound # IC-003893, listed under “Ferrate, tetracarbonyl”	Gives numerous references, including refs. to Fieser, Organic Syntheses, and Inorganic Syntheses.
Organic Syntheses	Vol. 59 or Collective Vol. VI	p. 102 p. 807	Gives uses in nucleophilic acylation, with detailed preparative methods and safety precautions.
Fieser & Fieser's Reagents for Organic Synthesis	Vol. 3 Vol. 4 Vol. 5 Vol. 6 Vol. 7 Vol. 8 Vol. 9 Vol. 10 Vol. 15	p. 267-284 p. 61-65 p. 624-625 p. 550-552 p. 341 p. 216-217 p. 205-207 p. 174 p. 152	Each reference gives a brief description of a preparative use of the compound, with references to the original papers in which they were described.
Encyclopedia of Reagents for Organic Synthesis	Vol. 4	p. 2299-2301	Listed under “Disodium Tetracarbonylferrate(-II)”; the listing gives CAS Registry Numbers for the parent compound, its dioxane complex and related compounds, molecular weights, melting point, solubility, handling information and descriptions of uses in organic synthesis with examples and extensive references.
Inorganic Syntheses	Vol. 7	p. 197	Detailed preparation of a THF solution of the compound.
Comprehensive Organometallic Chemistry	Vol. 4	p. 252	Synthesis, structure, IR, reactions
Comprehensive Organometallic Chemistry II	Vol. 12	p. 351-353	This volume, as a whole, covers “Transition Metal Organometallics in Organic Synthesis”. The compound appears in the chapter on “Transition Metal Carbonyl Complexes”. Gives a variety of syntheses in which the compound may be used, with sample reactions and extensive references
Dictionary of Organometallic Compounds	Vol. 1	p. 637	Compound # Fe-00040. Same references as in Dictionary of Inorganic Compounds above.
Comprehensive Organic Chemistry	Vol. 2	p. 908	Uses in alkoxycarbonylation.
Comprehensive Organic Synthesis	Vol. 8	p. 289, 371	Synthetic applications.
Comprehensive Organic Functional Group Transformations	Vol. 2 Vol. 3	p. 575 p. 20 p. 84 p. 128 p. 137	Synthesis and reaction with alkyl halides. Use in synthesis of aldehydes. Use in reduction of aldehydes. Conjugate reduction of enones. Use in synthesis of ketones.
Encyclopedia of Inorganic Chemistry	Vol. 4	p. 1735 p. 2131	Passing reference to the compound as a nucleophile. Reactions with dimanganese decacarbonyl.
Gmelin Handbook	Fe Vol. B2	Various	An extensive review, beginning with p. 20 (synthesis, density, Mossbauer, IR); p. 26-29, inorganic reactions of the compound; p. 31-46, organic reactions of the compound, all with extensive references.
Web Source	URL		Types of information given

Compound 1: Adrenaline		CAS Registry #: 51-43-4
Source (full name)	Vol. #	Page(s)	Types of information given
Merck Index	N.A.	p. 567	Compound #3569. Listed under “epinephrine”, but adrenaline is listed in the synonym index. Gives synonyms, mol. wt., mol. analysis, references to synthesis, biological studies, solubility. CAS Registry Number available from Reg. # index in back.
CRC Handbook of Chemistry and Physics (78th ed.)	N.A.	p. 3-43	Compound #1521. Listed under the systematic name, with cross-reference from “epinephrine” in the Synonym Index. Gives CAS Registry Number, Beilstein and Merck references, mol. wt., melting point, relative solubilities.
Aldrich Catalog 1996/97	N.A	p.653	Compound #21,930-4. Listed under (R)-Epinephrine. Note that the 99% pure optically active material has a different Registry Number from the 95% pure racemic material. Gives CAS Registry Number; mol. wt., melting point, optical rotation, Beilstein, Merck, Aldrich FT-NMR, FT-IR and Safety Data references
Encyclopedia of Analytical Science	Vol. 4 Vol. 5	p. 2447 p. 2945-2960	Environmental catalytic kinetic analysis Appears in chapter on “Mass spectrometry -- Applications” in the section on “Determination of biogenic amines”. Gives a wealth of data on using various mass spectrometric methods to analyze for adrenaline and its derivatives.
CRC Handbook of Data on Organic Compounds (3rd ed.)	Vol. 1	p. 907	Compound #4195. Gives CAS Registry #, mol. wt., melting point, density, solubilities, Beilstein, Merck and spectra references.
Handbook of Physical Properties of Organic Chemicals	N.A.	p. 9	Listed under the CAS Registry Number. Structure, mol. formula, mol. wt., mp, water solubility, partition coefficient, pKa, vapor pressure, Henry's Law constant, references
Dictionary of Organic Compounds (6th ed)	Vol. 1	p. 76	Compound #A-0-00689. Gives melting point, optical rotation, assorted references.
Dictionary of Natural Products	Vol. 1	p. 88	Compound #A-00480. Gives plant sources, similar data to above.
Dictionary of Drugs	Vol. 1	p. 16	Compound #A-00075. Same info as above.
Encyclopedia of Chemical Technology (4th ed.)	Vol. 9	p. 715	Gives names, mol. wt., melting point, absorption spectrum peaks, optical rotation, metabolism, isolation and synthesis, toxicity. lots of references. Similar article in 3rd ed., vol. 9 p.241.
Comprehensive Medicinal Chemistry	Vol. 3	p. 175-177	Describes neurotransmitter activity. Other smaller references scattered through other volumes.
Comprehensive Organic Chemistry	Vol. 5	p. 437	Passing reference.
Comprehensive Organic Synthesis	Vol. 2	p. 323	Passing reference.
Comprehensive Supramolecular Chemistry	Vol. 3	p. 575	This volume is on Cyclodextrins, and the chapter is devoted to preparative uses. This page makes reference to the use of cyclodextrins and capillary zone electrophoresis to resolve the optical isomers of epinephrine and related compounds.
Sadtler Spectra Collections	N.A.	N.A.	Listed under epinephrine. IR Grating #33391, Proton NMR #27566.
Rodd’s Chemistry of Carbon Compounds	Vol. IIIE	p. 85	Grouped with “polyhydric aralkanols”. Gives melting point, optical rotation, references to isolation, syntheses, physiological and pharmacological properties.
Sax’s Dangerous Properties of Industrial Materials	N.A.	N.A.	Lots of toxicity information on various salts of epinephrine, but curiously none on the parent compound.
Beilstein Handbook	Vol. 13	H, p. 830 E(I) p. 340 E(II) p. 523 E(III) p. 2834 E(IV) p. 2927 Note: E(V) is not yet in print	Could have found these using the references in several of the sources above, or by noting that epinephrine is an isocyclic compound with both hydroxy and amino substituents, which would put it in volume 13. Then use the appropriate molecular formula index to locate where in Vol. 13 it is. Physical data and references to every appearance of the compound in the organic chemical literature through 1959 or so.
Web Source	URL		Types of information given
Britannica Online	http://www.eb.com/		“epinephrine and norepinephrine” — Brief article describing the physiological action and medical applications of this hormone.
ChemFinder	http://chemfinder.camsoft.com/		Registry Number, synonyms, mol. wt., structure diagram, melting point, solubility in water, long list of links to other web sites with information on adrenaline.
Hazardous Chemicals Database	http://ull.chemistry.uakron.edu/erd/		Formula, molecular weight, melting point, solubility, chemical incompatibilities.
ECDIN — Environmental Chemicals Data Information Network	http://ulisse.etoit.eudra.org/Ecdin/Ecdin.html		Identification (names, m.p.), uses, European Community and US legislation, experimental toxicity data, concentration in human media, analytical methods.
Vermont SIRI MSDS	http://hazard.com/msds/		Materials Safety Data Sheets from three manufacturers.

This page created by Chuck Huber (huber@library.ucsb.edu).

Grace Baysinger, Head Librarian and Bibliographer
Swain Chemistry and Chemical Engineering Library, Stanford University Libraries
graceb@stanford.edu