4-Bromo-2,6-diisopropylaniline

Name: 4-Bromo-2,6-diisopropylaniline
Brand: ChemScene
Availability: InStock
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CAS No. 80058-84-0
Cat. No. CS-W019405
Purity≥96%
MDL No.MFCD09743895

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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+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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4-Bromo-2,6-diisopropylaniline|CS-W019405

Structure of 80058-84-0

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General Information

CAS No. 80058-84-0
Cat. No. CS-W019405
Purity ≥96%
MDL No. MFCD09743895
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₈BrN
Molecular Weight 256.18
Synonym(s) Benzenamine, 4-bromo-2,6-bis(1-methylethyl)-
SMILES NC1=C(C(C)C)C=C(Br)C=C1C(C)C

Description

4-Bromo-2,6-diisopropylaniline features a sterically hindered aromatic core with bromine and two isopropyl groups positioned ortho to the amine. This configuration imparts enhanced stability and directs electrophilic substitution regioselectively, making it valuable for constructing complex intermediates in pharmaceutical and agrochemical synthesis under standard conditions.

Application

4-Bromo-2,6-diisopropylaniline serves as a sterically hindered arylamine building block for the synthesis of pharmaceutical intermediates and functional materials. Its electron-rich aromatic core facilitates palladium-catalyzed cross-coupling reactions, while the diisopropyl substituents provide enhanced bench stability and reduce undesired side reactions. The bromine moiety enables further functionalization via Suzuki-Miyaura or Negishi couplings, making it a practical scaffold for complex molecule assembly in medicinal chemistry workflows.

Synthesis

Route1
- In-stock
  
  24544-04-5
- ~99%
- In-stock
  
  80058-84-0
References
- UNIVERSAL DISPLAY CORPORATION; XIA, Chuanjin; YEAGER, Walter; LI, David Zenan; FIORDELISIO, James; MA, Bin; ELSHENAWY, Zeinab; LAYEK, Suman; BARRON, Edward; KOTTAS, Gregg; BROOKS, Jason Patent: WO2012/116231 A2, 2012 ; Location in patent: Page/Page column 120 ;
Route2
- 50522-40-2
- ~76%
- In-stock
  
  80058-84-0
References
- Liu, Hua-Rong; Gomes, Pedro T.; Costa, Sandra I.; Duarte, M. Teresa; Branquinho; Fernandes, Anabela C.; Chien, James C.W.; Singh; Marques, Maria M. Journal of Organometallic Chemistry, 2005 , vol. 690, # 5 p. 1314 - 1323

Safety Information

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GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2810
Class : 6.1	Packing Group : Ⅲ
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 26.02
LogP 4.2781
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4-Bromo-2,6-diisopropylaniline

CAS No. 80058-84-0

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