2-methyl-6-nitrobenzoxazole

Name: 2-methyl-6-nitrobenzoxazole
Brand: ChemScene
Availability: InStock
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CAS No. 5683-43-2
Cat. No. CS-0030386
Purity≥97%
MDL No.MFCD00022848

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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+
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Structure of 5683-43-2

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General Information

CAS No. 5683-43-2
Cat. No. CS-0030386
Purity ≥97%
MDL No. MFCD00022848
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₆N₂O₃
Molecular Weight None
Synonym(s) 3-{[(1E)-phenylmethylidene]amino}-3H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-one
SMILES O=[N+](C1=CC=C2N=C(C)OC2=C1)[O-]

Description

2-Methyl-6-nitrobenzoxazole features a fused heterocyclic core with complementary electron-withdrawing and steric influences. The para-nitro group enhances electrophilicity, while the methyl substituent provides modest steric shielding. This combination enables reliable participation in cross-coupling reactions and facilitates incorporation into advanced photonic materials and bioactive scaffolds under standard conditions.

Application

2-Methyl-6-nitrobenzoxazole serves as a versatile heterocyclic building block in medicinal chemistry, enabling efficient access to biologically active scaffolds. Its electron-deficient aromatic core facilitates nucleophilic substitution and transition-metal-catalyzed coupling reactions. The methyl and nitro groups provide orthogonal handles for selective functionalization, while the benzoxazole framework offers metabolic stability and favorable pharmacokinetic properties. This compound exhibits excellent bench stability and is compatible with standard purification methods, making it ideal for iterative synthesis workflows in drug discovery and process development.

Synthesis

Route1
- In-stock
  
  25351-89-7
- ~82%
- In-stock
  
  5683-43-2
References
- Rambabu; Murthi, P. Radha Krishna; Dulla, Balakrishna; Basaveswara Rao; Pal, Manojit Synthetic Communications, 2013 , vol. 43, # 22 p. 3083 - 3092
Route2
- 78-39-7
- 121-88-0
- ~83%
- In-stock
  
  5683-43-2
References
- Barbero, Margherita; Cadamuro, Silvano; Dughera, Stefano Arkivoc, 2012 , vol. 2012, # 9 p. 262 - 279
Route3
- In-stock
  
  95-21-6
- ~%
- In-stock
  
  5683-43-2
- In-stock
  
  32046-51-8
References
- Tetrahedron Letters, , vol. 48, # 49 p. 8659 - 8664

Safety Information

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GHS Pictogram :	GHS No : GHS05,GHS07
Signal Word : Danger	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H318
Precautionary Statements : P264-P270-P280-P305+P351+P338-P330-P501

Quality Control

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Computational Chemistry Data

TPSA 69.17
LogP 2.04442
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Benzooxazole compounds

Key Words

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2-methyl-6-nitrobenzoxazole

CAS No. 5683-43-2

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