5-Bromo-2,4-dimethylaniline

Name: 5-Bromo-2,4-dimethylaniline
Brand: ChemScene
Availability: InStock
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CAS No. 69383-60-4
Cat. No. CS-0153309
Purity≥95%
MDL No.MFCD09038481

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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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General Information

CAS No. 69383-60-4
Cat. No. CS-0153309
Purity ≥95%
MDL No. MFCD09038481
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₁₀BrN
Molecular Weight 200.08
Synonym(s) NSC 159240
SMILES CC1=CC(=C(C=C1Br)N)C

Description

5-Bromo-2,4-dimethylaniline features a bromine substituent at the 5-position and methyl groups at the 2- and 4-positions relative to the amino group. This electron-rich aromatic scaffold offers enhanced stability and selective reactivity in cross-coupling processes. The steric shielding from adjacent methyl groups improves regiocontrol during functionalization.

Application

5-Bromo-2,4-dimethylaniline serves as a valuable building block in medicinal chemistry and agrochemical synthesis, offering a well-defined substitution pattern for Suzuki-Miyaura and Ullmann coupling reactions. The ortho-methyl groups provide steric protection and enhance bench stability, while the bromine atom enables reliable cross-coupling transformations. Its functional group tolerance facilitates downstream derivatization, making it a practical choice for constructing complex aromatic scaffolds.

Synthesis

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References
- WO2009/44311 A1, ; Page/Page column 42-43 ; WO 2009/044311 A1
Route2
- 2050-43-3
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References
- Journal fuer Praktische Chemie (Leipzig), , vol. <2>53, p. 552 Chemische Berichte, , vol. 2, p. 686 Chemische Berichte, , vol. 3, p. 225
Route3
- 70853-94-0
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References
- Justus Liebigs Annalen der Chemie, , vol. 424, p. 300 Justus Liebigs Annalen der Chemie, , vol. 441, p. 303

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

TPSA 26.02
LogP 2.64814
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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5-Bromo-2,4-dimethylaniline

CAS No. 69383-60-4

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