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

Assignment 1 Answers: 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. Note: AZT is too recently synthesized a compound to appear in the print version of Beilstein, though it does appear in the electronic versions.

Compound 1: Trimethyltin chloride CAS Registry #: 1066-45-1
Source (full name) Vol. # Page(s) Types of information given
Aldrich Catalog 1996/97 N.A. page 1496, #14,649-8 CAS Registry Number, mol. wt., melting point, flash point. Gives references to Beilstein, Fieser and the Aldrich Handbooks of Safety Data, FT-NMR and FT-IR and brief safety warnings.
CRC Handbook of Chemistry and Physics, 78th ed. N.A. 3-315 Listed under “Stannane, chlorotrimethyl-”. Mol. formula, mol. wt., CAS Registry Number, mp, bp, solubility
Handbook of Data on Organic Compounds, 3rd ed. Vol. V p. 4973, Compound #26089 CAS Registry Number, mol. formula, mol. wt., mp, bp, solubility, structure, mass spectrum peaks (w/ref. to NIST database), IR peaks, NMR peaks (with references to Sadtler)
Dictionary of Organometallic Compounds, 2nd ed. Vol. 4 p.4130, compound # Sn-00037 Listed under “Chlorotrimethylstannane” Gives CAS RN, mol. form., mol. wt. mp, bp, color, basic toxicity, numerous references, including ref. to Saz’s Dangerous Properties.
Organic Syntheses Vol. 68 or
Collective Vol. VIII		 p. 121-122
p. 100		 Brief but detailed preparation as an intermediate in making another tin reagent.
Fieser & Fieser's Reagents for Organic Synthesis Vol. 10
Vol. 14
Vol. 17		 p.392, p.451
p.335
p.388		 The first three references mention the compound passingly in reactions with other reagents. The last reference covers usage of it in cyclization of dienes and trienes, with a reference to the original literature.
Encyclopedia of Reagents for Organic Synthesis Vol. 2 p. 1241-1242 Listed under “Chlorotrimethylstannane”; the listing gives the CAS Registry Number, mol, wt., mp, bp, solubility, handling information and descriptions of uses in organic synthesis with examples and extensive references.
Comprehensive Organometallic Chemistry Vol. 2 p.530
532-533
545-563		 119Sn coupling constants
Reactions to form tetraorganotin compounds.
General section on organotin halides. Includes physical properties and reaction information.
Comprehensive Organometallic Chemistry II Vol. 2 p. 220 Spin coupling in 119Sn NMR of the compound.
Comprehensive Organic Chemistry Vol. 1 p. 535 Use with borohydride for reductions.
Comprehensive Organic Synthesis Vol. 1 p. 305 Lewis acid complexes with carbonyl compounds.
Encyclopedia of Inorganic Chemistry Vol. 3
Vol. 8		 p. 1502
p. 4182-3		 Under “Hypervalent Compounds”: Stability of comples w/pyridine
Under “Tin: Organometallic Chemistry”: Solid state structure and reaction paths.
Gmelin Handbook Sn (Vol. 46)
Organische Verbindungen Teil 5
(Organic Compounds, Part 5)		 p. 63-89 An extensive review, beginning with p.63-68 (synthesis, thermodynamics); p. 68-76 (molecular structure, various spectra), p. 76-77 (other phys. properties, electrochemistry), p. 77-87 (inorganic and organic reactions of the compound) p. 88-89 (physiological effects, uses), all with extensive references.
Beilstein Handbook Vol. 4 E(II) p. 1011
E(III) p. 1923
E(IV) p. 4324
Note: E(V) for aliphatics is not yet in print		 Methyl group attached to Sn gives Vol 4. But from here on in, this one is very tricky to find. If you look in the cumulative molecular formula index, there is no reference for C3H9ClSn, but there is one for C3H9ClSn+: the chloride is treated as a derivative of the cation or of the hydroxide. Your best bet was to start from the reference in the Aldrich Catalog (see above.) E(II) has mp and references for other physical properties, reactions and preparations. E(III) has mp, preparation and reaction references, and E(IV) has mp and a preparation reference.
Encyclopedia of Analytical Science Vol. 9 p.5228-5235 Under “Tin”, much general information about analysis for organotin compounds with extensive references; specific reference to atomic absorption detection limits for the compound
Sadtler Standard Grating IR Spectra Vol. 16 N.A. Spectrum #15468K, under “chlorotrimethyltin”, mol. formula, mol. wt., mp, infrared spectrum, conditions of spectrum.
Sadtler Standard NMR Spectra Vol. 13 N.A. Spectrum #8061M, under “chlorotrimethyltin” mol. formula, mol. wt., mp, Proton NMR spectrum, peak assignment, conditions of spectrum.
Aldrich Library of NMR Spectra N.A. 10-166C Under “Trimethyltin chloride”, Aldrich Catalog number, mol. formula, mol. wt., mp, structure, proton NMR spectrum, cross-reference to Aldrich IR Library.
Aldrich Library of 13C and 1H FT NMR Spectra Vol. 3 p. 739 Under “Trimethyltin chloride”: Aldrich Catalog number, CAS Reg. Num., mol. formula, mol. wt., mp, flash point, C-13 and proton NMR spectra, list of C-13 peaks, cross references to 60 MHz NMR library, FT IR library.
Handbook of Proton NMR Spectra and Data Vol. 6 p. 37 Under “Chlorotrimethylstannane”, CAS Reg. Number, mol. formula, mol. wt, mp, NMR spectrum, peak assignment, with details of how spectrum was taken
Sax’s Dangerous Properties of Industrial Materials, 8th ed. Vol. II Compound CLT000 Under “chlorotrimethylstannane”, CAS Registry Number, mol. formula, mol. wt, mp, synonyms, toxicity data (several LD50's) with references, OSHA and NIOSH exposure limits.
Web Source URL Types of information given
NIST Chemistry Webbook http://webbook.nist.gov/ Mol. formula, mol. wt., CAS Registry Number, synonyms, structure, gas phase ionization energies, IR spectrum, mass spectrum, references.
ChemFinder http://chemfinder.camsoft.com/ Registry Number, synonyms, mol. wt., structure diagram, melting point, flash point, list of links to other web sites with information on the compound.
ECDIN — Environmental Chemicals Data Information Network http://ulisse.etoit.eudra.org/Ecdin/Ecdin.html Identification (names, CAS Reg. Num. mol. formula, ), uses, aquatic toxicity data, hazard and safety information.
Vermont SIRI MSDS http://hazard.com/msds/ Materials Safety Data Sheet from Acros, which includes CAS Reg. Number, mol. formula, mol. wt., mp, bp, flash point, toxicity, safety and hazard information.
Compound 2: AZT (an anti-HIV drug) CAS Registry #: 30516-87-1
Source (full name) Vol. # Page(s) Types of information given
Merck Index 12th ed. N.A. p. 1732 Compound #10252. Listed under “zidovudine”, but AZT is listed in the synonym index. Gives synonyms, mol. wt., mol. analysis, mp, solubility, opt. rotation, UV peak absorbance, toxicity, references to synthesis, biological studies, and more. CAS Registry Number available from Reg. # index in back.
Aldrich Catalog 1996/97 N.A p. 125 Compound #32,360-8 Listed under 3'-azido-3'-deoxythymidine. Gives CAS Registry Number; mol. wt., melting point, optical rotation, Aldrich FT-NMR, and Safety Data references
Handbook of Physical Properties of Organic Compounds N.A. p.1058 Listed under CAS Reg. Number. Structure, mol. formula, mol. wt., systematic name, mp, water solubility, partition coefficient, vapor pressure, Henry’s Law constant, hydroxyl reaction rate coefficient, with references.
Dictionary of Organic Compounds (6th ed) Vol 1. p. 527 Compound #A-0-04712. Listed under “3'-azido-3'-deoxythymidine”. Gives synonyms, CAS Registry Number, structure, mol. formula, mol. wt., melting point, assorted references, including Aldrich FT NMR Library.
Dictionary of Drugs Vol. 1 p. 1299 Compound #Z-00013. Gives synonyms, CAS Registry Number, structure, mol. formula, mol. wt., melting point, optical rotation, some references.
Encyclopedia of Chemical Technology (4th ed.) Vol. 3 p. 599 Part of chapter on “Antiviral Agents”, section on “Agents active against persistent viral infections”. Gives CAS Registry Number, mol. formula, structure; discusses physiological mode of action, lots of references.
Comprehensive Medicinal Chemistry Vol. 2 p. 319, 760-761 Structure, mode of action, structure-activity relationships, extensive references. Other scattered mentions in other volumes.
Web Source URL Types of information given
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 this compound.

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

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