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CS-W001157 4
Total: USD 88.00

1-(Bromomethyl)naphthalene

  • CAS No. 3163-27-7

  • Cat. No. CS-W021252
  • Purity≥97%
  • MDL No.MFCD00010804

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

1-(Bromomethyl)naphthalene|CS-W021252

Structure of 3163-27-7

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General Information

  • CAS No. 3163-27-7
  • Cat. No. CS-W021252
  • Purity ≥97%
  • MDL No. MFCD00010804
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₉Br
  • Molecular Weight 221.09
  • Synonym(s) None
  • SMILES BrCC1=C2C=CC=CC2=CC=C1

Description

1-(Bromomethyl)naphthalene features a reactive bromomethyl group appended to the naphthalene scaffold, enabling direct functionalization in cross-coupling and nucleophilic substitution reactions. This bench-stable, moisture-tolerant reagent integrates seamlessly into synthetic sequences requiring aromatic alkyl halide intermediates, offering high regiocontrol and compatibility with palladium-catalyzed transformations.

Application

1-(Bromomethyl)naphthalene serves as a versatile benzylating agent in synthetic organic chemistry, enabling efficient introduction of naphthylmethyl groups into diverse substrates. Its bromomethyl functionality reacts reliably with nucleophiles such as amines, thiols, and carbanions under mild conditions, facilitating the construction of biologically relevant scaffolds. The compound exhibits good bench stability and is compatible with standard purification techniques, making it well-suited for iterative synthesis and process-scale applications.

Synthesis

  • Route1

    References

    • Tarrade-Matha, Aurelie; Pillon, Florence; Doris, Eric Synthetic Communications, 2010 , vol. 40, # 11 p. 1646 - 1649
  • Route2
    • null|null
      90-12-0
    • ~93%
    • In-stock
      1-(Bromomethyl)naphthalene|CS-W021252
      3163-27-7

    References

    • Karatsu, Takashi; Hiresaki, Tatsuro; Arai, Tatsuo; Sakuragi, Hirochika; Tokumaru, Katsumi; Wirz, Jakob Bulletin of the Chemical Society of Japan, 1991 , vol. 64, # 11 p. 3355 - 3362
  • Route3

    References

    • Kabalka, George W.; Wu, Zhongzhi; Ju, Yuhong Tetrahedron Letters, 2000 , vol. 41, # 27 p. 5161 - 5164

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3261
Class : 8
Packing Group : Ⅱ
Hazard Statements : H314-H318
Precautionary Statements : P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P363-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   0
  • LogP   3.7347
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   1

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