1-Chloro-2-iodo-4-nitrobenzene

Name: 1-Chloro-2-iodo-4-nitrobenzene
Brand: ChemScene
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CAS No. 74534-15-9
Cat. No. CS-M1168
Purity≥98%
MDL No.MFCD11521301

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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+
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General Information

CAS No. 74534-15-9
Cat. No. CS-M1168
Purity ≥98%
MDL No. MFCD11521301
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₃ClINO₂
Molecular Weight 283.45
Synonym(s) 1-chloro-2-iodo-4-nitro-benzene
SMILES ClC(C=CC([N+]([O-])=O)=C1)=C1I

Description

1-Chloro-2-iodo-4-nitrobenzene features a trifunctional aromatic core with orthogonal reactivity, enabling sequential cross-coupling in late-stage functionalization. The electron-deficient ring facilitates palladium-catalyzed transformations, while the chloro and iodo groups offer complementary coupling handles. This compound delivers high regioselectivity in Buchwald-Hartwig and Stille reactions under standard conditions.

Application

1-Chloro-2-iodo-4-nitrobenzene serves as a versatile dihalogenated building block for palladium-catalyzed cross-coupling reactions, enabling sequential functionalization at distinct ring positions. The chloro group exhibits high reactivity in Suzuki, Stille, and Negishi couplings, while the iodo moiety allows for orthogonal transformation via Buchwald-Hartwig amination or further coupling. Its stability under standard bench conditions and compatibility with diverse functional groups make it suitable for constructing complex aryl scaffolds in medicinal chemistry and materials science.

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 43.14
LogP 2.8528
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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1-Chloro-2-iodo-4-nitrobenzene

CAS No. 74534-15-9

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