5-Bromo-2-nitrophenol

Name: 5-Bromo-2-nitrophenol
Brand: ChemScene
Availability: InStock
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CAS No. 27684-84-0
Cat. No. CS-W003014
Purity≥98%
MDL No.MFCD03095027

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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 27684-84-0

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General Information

CAS No. 27684-84-0
Cat. No. CS-W003014
Purity ≥98%
MDL No. MFCD03095027
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄BrNO₃
Molecular Weight 218.01
Synonym(s) 5-bromo-2-ntrophenol
SMILES Brc1ccc(c(c1)O)[N+](=O)[O-]

Description

5-Bromo-2-nitrophenol features a bromine substituent at the 5-position and a nitro group at the 2-position on a phenolic scaffold. This electron-deficient aromatic system enables direct functionalization in cross-coupling reactions, while the phenolic hydroxyl offers a handle for derivatization. The compound exhibits enhanced stability under standard bench conditions and serves as a key intermediate in synthetic pathways requiring halogenated nitroaromatics.

Application

5-Bromo-2-nitrophenol serves as a versatile building block in medicinal chemistry and materials science, enabling direct functionalization via palladium-catalyzed cross-coupling reactions. Its ortho-nitro and bromo substituents offer complementary reactivity for sequential transformations, including nitro group reduction followed by coupling or cyclization. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for multi-step synthesis workflows.

Synthesis

Route1
- 591-20-8
- ~29%
- In-stock
  
  27684-84-0
References
- Perez-Bolivar, Cesar; Takizawa, Shin-Ya; Nishimura, Go; Montes, Victor A.; Anzenbacher, Pavel Chemistry - A European Journal, 2011 , vol. 17, # 33 p. 9076 - 9082
Route2
- 591-20-8
- ~21%
- In-stock
  
  27684-84-0
- In-stock
  
  5470-65-5
References
- Shen, Yuehai; Xie, Qian; Norberg, Monica; Sausville, Edward; Vande Woude, George; Wenkert, David Bioorganic and Medicinal Chemistry, 2005 , vol. 13, # 16 p. 4960 - 4971
Route3
- 586-78-7
- ~80%
- 100-02-7
- In-stock
  
  27684-84-0
References
- Makosza, Mieczyslaw; Sienkiewicz, Krzysztof Journal of Organic Chemistry, 1998 , vol. 63, # 13 p. 4199 - 4208

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

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5-Bromo-2-nitrophenol

CAS No. 27684-84-0

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