1,5-Dimethyl-2,4-dinitrobenzene

Name: 1,5-Dimethyl-2,4-dinitrobenzene
Brand: ChemScene
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CAS No. 616-72-8
Cat. No. CS-0038125
Purity≥98%
MDL No.MFCD00065251

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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1,5-Dimethyl-2,4-dinitrobenzene|CS-0038125

Structure of 616-72-8

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General Information

CAS No. 616-72-8
Cat. No. CS-0038125
Purity ≥98%
MDL No. MFCD00065251
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₈N₂O₄
Molecular Weight 196.16
Synonym(s) 4,6-DINITRO-1,3-XYLENE
SMILES CC1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])C

Description

1,5-Dimethyl-2,4-dinitrobenzene features two nitro groups flanking a central ring, delivering high electron deficiency for nucleophilic aromatic substitution. The methyl substituents enhance solubility and stabilize the intermediate Meisenheimer complex. This compound serves as a robust electrophilic handle in synthetic transformations requiring controlled reactivity under standard conditions.

Application

1,5-Dimethyl-2,4-dinitrobenzene serves as a versatile building block in synthetic organic chemistry, enabling the construction of substituted aromatic systems through nucleophilic aromatic substitution. Its electron-deficient nature facilitates reactions with amines and thiols under mild conditions, while the methyl groups provide steric and electronic modulation. Bench-stable and readily purified by recrystallization, it functions effectively in the synthesis of heterocyclic scaffolds and functionalized intermediates for medicinal chemistry applications.

Synthesis

Route1
- 108-38-3
- ~%
- In-stock
  
  616-72-8
References
- Brand; Mahr Journal fuer Praktische Chemie (Leipzig), 1935 , vol. <2> 142, p. 153,166
Route2
- 89-87-2
- ~73%
- In-stock
  
  616-72-8
References
- Zhang, Aimin; Han, Yaohua; Yamato, Kazuhiro; Zeng, Xiao Cheng; Gong, Bing Organic Letters, 2006 , vol. 8, # 5 p. 803 - 806
Route3
- 108-38-3
- ~44%
- In-stock
  
  616-72-8
- 603-02-1
References
- Quast, Helmut; Schoen, Norbert Liebigs Annalen der Chemie, 1984 , # 1 p. 133 - 146

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07,GHS09
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H401-H411
Precautionary Statements : P264-P270-P273-P330-P391-P501

Quality Control

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Computational Chemistry Data

TPSA 86.28
LogP 2.11984
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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1,5-Dimethyl-2,4-dinitrobenzene

CAS No. 616-72-8

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