3-Bromo-4-nitrophenol

Name: 3-Bromo-4-nitrophenol
Brand: ChemScene
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CAS No. 5470-65-5
Cat. No. CS-W003684
Purity≥97%
MDL No.MFCD09907826

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 5470-65-5

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General Information

CAS No. 5470-65-5
Cat. No. CS-W003684
Purity ≥97%
MDL No. MFCD09907826
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄BrNO₃
Molecular Weight 218.01
Synonym(s) 3-Brom-4-nitro-1-hydroxy-benzol
SMILES Oc1ccc(c(c1)Br)[N+](=O)[O-]

Description

3-Bromo-4-nitrophenol features a bromine substituent flanked by a nitro group and hydroxyl moiety, creating a uniquely reactive trifunctional scaffold. This electron-deficient phenol integrates readily into cross-coupling reactions and serves as a key intermediate in the synthesis of functionalized aryl compounds. The molecule exhibits enhanced stability under standard bench conditions and displays favorable solubility in common organic solvents.

Application

3-Bromo-4-nitrophenol serves as a versatile building block in medicinal chemistry and materials science, enabling direct functionalization via palladium-catalyzed cross-coupling reactions. Its bromo group facilitates Suzuki, Stille, and Negishi couplings, while the nitro group allows for selective reduction or participation in electrophilic substitution. The compound exhibits bench stability and compatibility with common protecting group strategies, supporting efficient synthesis of complex heterocyclic scaffolds and functionalized aryl derivatives.

Synthesis

Route1
- 591-20-8
- ~38%
- In-stock
  
  5470-65-5
References
- Jung, Kwan-Young; Vanommeslaeghe, Kenno; Lanning, Maryanna E.; Yap, Jeremy L.; Gordon, Caryn; Wilder, Paul T.; Mackerell, Alexander D.; Fletcher, Steven Organic Letters, 2013 , vol. 15, # 13 p. 3234 - 3237
Route2
- 591-20-8
- ~45%
- In-stock
  
  27684-84-0
- In-stock
  
  5470-65-5
References
- Tetrahedron Letters, , vol. 28, # 50 p. 6389-6390
Route3
- 577-19-5
- ~%
- In-stock
  
  13073-25-1
- In-stock
  
  5847-59-6
- In-stock
  
  5470-65-5
- In-stock
  
  76361-99-4
References
- Journal of Organic Chemistry USSR (English Translation), , vol. 27, # 6.2 p. 1149 - 1152 Zhurnal Organicheskoi Khimii, , vol. 27, # 6 p. 1317 - 1320

Safety Information

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GHS Pictogram :	GHS No : GHS05,GHS07,GHS09
Signal Word : Danger	UN#: 3077
Class : 9	Packing Group : Ⅲ
Hazard Statements : H302-H315-H317-H318-H410
Precautionary Statements : P261-P264-P270-P272-P273-P280-P302+P352-P330-P362+P364-P391-P501

Quality Control

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Computational Chemistry Data

TPSA 63.37
LogP 2.0629
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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3-Bromo-4-nitrophenol

CAS No. 5470-65-5

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