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CS-W001157 4
Total: USD 88.00

2,2'-(1,4-Phenylene)diacetonitrile

  • CAS No. 622-75-3

  • Cat. No. CS-W021467
  • Purity≥97%
  • MDL No.MFCD00001923

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

2,2'-(1,4-Phenylene)diacetonitrile|CS-W021467

Structure of 622-75-3

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General Information

  • CAS No. 622-75-3
  • Cat. No. CS-W021467
  • Purity ≥97%
  • MDL No. MFCD00001923
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈N₂
  • Molecular Weight 156.18
  • Synonym(s) α,α'-Dicyano-p-xylene
  • SMILES N#CCC1=CC=C(CC#N)C=C1

Description

2,2'-(1,4-Phenylene)diacetonitrile features a rigid para-substituted aromatic core flanked by nitrile groups, enabling its use as a bifunctional synthon in organic synthesis. The electron-deficient phenylene scaffold enhances reactivity in conjugate additions and cycloadditions. This bench-stable compound integrates readily into molecular architectures requiring polar, linear linkages.

Application

2,2'-(1,4-Phenylene)diacetonitrile serves as a versatile bifunctional building block in synthetic organic chemistry, enabling the construction of conjugated systems and heterocyclic scaffolds. Its dual nitrile groups facilitate efficient Michael additions, cyclizations, and metal-catalyzed couplings. The compound exhibits excellent bench stability and compatibility with diverse reaction conditions, simplifying purification and scalability in multi-step syntheses.

Synthesis

  • Route1
    • null|null
      38622-91-2
    • In-stock
      Terephthalaldehyde|CS-W020006
      623-27-8
    • ~32%
    • In-stock
      2,2'-(1,4-Phenylene)diacetonitrile|CS-W021467
      622-75-3

    References

    • Thompson, Barry C.; Kim, Young-Gi; McCarley, Tracy D.; Reynolds, John R. Journal of the American Chemical Society, 2006 , vol. 128, # 39 p. 12714 - 12725
  • Route2
    • null|null
      143-33-9
    • null|null
      623-25-6
    • ~86%
    • In-stock
      2,2'-(1,4-Phenylene)diacetonitrile|CS-W021467
      622-75-3

    References

    • Radau, Gregor Monatshefte fur Chemie, 2003 , vol. 134, # 8 p. 1159 - 1166
  • Route3
    • null|null
      623-24-5
    • null|null
      151-50-8
    • ~%
    • In-stock
      2,2'-(1,4-Phenylene)diacetonitrile|CS-W021467
      622-75-3

    References

    • Journal of the Chemical Society, , p. 519

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302+H312+H332-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   47.58
  • LogP   1.81876
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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