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CS-W001157 4
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(3-Nitrophenyl)methanethiol

  • CAS No. 77472-39-0

  • Cat. No. CS-0168892
  • Purity≥98%
  • MDL No.MFCD00024542

*For research and further manufacturing use only, not for direct human use.

(3-Nitrophenyl)methanethiol|CS-0168892

Structure of 77472-39-0

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General Information

  • CAS No. 77472-39-0
  • Cat. No. CS-0168892
  • Purity ≥98%
  • MDL No. MFCD00024542
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₇NO₂S
  • Molecular Weight None
  • Synonym(s) (3-Nitrobenzyl)mercaptan
  • SMILES SCC1=CC=CC([N+]([O-])=O)=C1

Description

(3-Nitrophenyl)methanethiol features a nitro-substituted phenyl ring linked to a thiol group, delivering enhanced reactivity and electron-withdrawing character. This configuration supports efficient conjugation in synthetic transformations and enables selective functionalization in complex molecular architectures. The compound exhibits robust stability under standard conditions, facilitating reliable use in organic synthesis and materials development.

Application

(3-Nitrophenyl)methanethiol serves as a versatile building block for sulfide-based heterocycles and functionalized arylthio compounds. Its ortho-nitro group enhances electrophilicity at the aromatic ring, enabling efficient palladium-catalyzed coupling reactions. The thiol functionality offers reliable conjugation chemistry and facilitates purification via precipitation or ion-exchange chromatography. Bench-stable and compatible with common protecting groups, it functions effectively in multistep synthesis of pharmaceutical intermediates and agrochemical scaffolds.

Synthesis

  • Route1
    • O-ethyl S-(3-nitrobenzyl) carbonodithioate|CS-0507396
      1335107-28-2
    • ~88%
    • In-stock
      (3-Nitrophenyl)methanethiol|CS-0168892
      77472-39-0

    References

    • Morgan, M. Thomas; Bagchi, Pritha; Fahrni, Christoph J. Journal of the American Chemical Society, 2011 , vol. 133, # 40 p. 15906 - 15909
  • Route2
    • null|null
      619-23-8
    • ~%
    • In-stock
      (3-Nitrophenyl)methanethiol|CS-0168892
      77472-39-0

    References

    • Bellas,M. et al. Journal of Organic Chemistry, 1967 , vol. 32, p. 2591 - 2595
  • Route3
    • null|null
      66907-51-5
    • ~%
    • In-stock
      (3-Nitrophenyl)methanethiol|CS-0168892
      77472-39-0

    References

    • Brembilla, Alain; Roizard, Denis; Schoenleber, Jacqueline; Lochon, Pierre Canadian Journal of Chemistry, 1984 , vol. 62, p. 2330 - 2336

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H315-H318-H335
Precautionary Statements : P261-P264-P271-P272-P280-P302+P352-P304+P340-P405-P501

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Computational Chemistry Data

  • TPSA   43.14
  • LogP   2.0246
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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