p-Toluenesulfonyl hydrazide

p-Toluenesulfonyl hydrazide is the organic compound with the formula CH3C6H4SO2NHNH2. It is a white solid that is soluble in many organic solvents but not water or alkanes. It is a reagent in organic synthesis.[1]

p-Toluenesulfonyl hydrazide
Names
IUPAC name
4-methylbenzenesulfonohydrazide
Other names
tosyl hydrazide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.014.917
EC Number
  • 216-407-3
UNII
  • InChI=1S/C7H10N2O2S/c1-6-2-4-7(5-3-6)12(10,11)9-8/h2-5,9H,8H2,1H3
    Key: ICGLPKIVTVWCFT-UHFFFAOYSA-N
  • CC1=CC=C(C=C1)S(=O)(=O)NN
Properties
Appearance white solid
Melting point 108–110 °C (226–230 °F; 381–383 K)
Hazards
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H242, H301, H302, H315, H317, H319, H341, H373, H410
P201, P202, P210, P220, P234, P260, P261, P264, P270, P272, P273, P280, P281, P301+P310, P301+P312, P302+P352, P305+P351+P338, P308+P313, P314, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P391, P403+P235, P405, P411, P420, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Reactions

With ketones and aldehydes, it condenses to give the hydrazones:

CH3C6H4SO2NHNH2 + R2C=O → CH3C6H4SO2NHN=CR2 + H2O

Upon heating in solution, it degrades, releasing diimide (N2H2), a useful reducing agent. Triisopropylbenzenesulfonylhydrazide is far more useful for this reaction.

Synthesis

Toluenesulfonyl hydrazide is prepared by the reaction of a toluenesulfonyl chloride with hydrazine:[2]

CH3C6H4SO2Cl + 2 NH2NH2 → CH3C6H4SO2NHNH2 + + [NH2NH3]Cl

Reactions
Preparation of 4-chloroquinazoline and its tosylhydrazide.

Tosylhydrazides can be installed by nucleophilic attack and later removed by base. It thus provides a way to covert C-Cl to C-H.[3]

References
  1. Chamberlin, A. Richard; Sheppeck, James E.; Goess, Brian; Lee, Chulbom (2007). "P-Toluenesulfonylhydrazide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt137.pub2. ISBN 978-0471936237.
  2. Friedman, Lester; Litle, Robert L.; Reichle, Walter R. (1960). "p-Toluenesulfonylhydrazide". Org. Synth. 40: 93. doi:10.15227/orgsyn.040.0093.
  3. W. L. F. Armarego (1967). "Halogenoquinazolines". In W. L. F. Armarego (ed.). Chemistry of Heterocyclic Compounds. pp. 11–38. doi:10.1002/9780470186916.ch7. ISBN 9780470186916.
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