2-Amino-2'-chloro-5-nitrobenzophenone

Name: 2-Amino-2'-chloro-5-nitrobenzophenone
Brand: ChemScene
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CAS No. 2011-66-7
Cat. No. CS-W012312
Purity≥98%
MDL No.MFCD00792453

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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2-Amino-2'-chloro-5-nitrobenzophenone|CS-W012312

Structure of 2011-66-7

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General Information

CAS No. 2011-66-7
Cat. No. CS-W012312
Purity ≥98%
MDL No. MFCD00792453
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₉ClN₂O₃
Molecular Weight 276.68
Synonym(s) None
SMILES ClC1=CC=CC=C1C(C2=C(N)C=CC(N(=O)=O)=C2)=O

Description

An adenosine analog that acts as a selective, high affinity agonist for Adenosine A1 receptor (A1R) (Ki = 800 pM; 2.3 M, 18.8 M, and 42 nM for human A1, A2A, A2B, A3 respectively). Shown to be centrally active following systemic administration and exhibits anti-convulsive effects. Also reported to inhibit adenylate cyclase activity in rat fat cell membrane (IC50 = 33 nM). Diminishes respiratory rhythm, reduces heart rate, and enhances the activity of KATP channels. Reduces norepinephrine release by about 50% in untreated and pertussis toxin treated hearts.

Application

2-Amino-2'-chloro-5-nitrobenzophenone serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted quinoline and benzimidazole scaffolds. Its ortho-chloro and nitro groups facilitate sequential functionalization via palladium-catalyzed coupling and reduction protocols. The compound exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for iterative synthetic campaigns in medicinal chemistry and process development.

Synthesis

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References
- Journal of Medicinal Chemistry, , vol. 6, p. 261 - 265
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References
- Journal of Medicinal Chemistry, , vol. 34, # 5 p. 1545 - 1552
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References
- Archiv der Pharmazie, , vol. 324, # 7 p. 417 - 421

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS08
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H341
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 86.23
LogP 3.0614
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Ketone

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-Amino-2'-chloro-5-nitrobenzophenone

CAS No. 2011-66-7

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