4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine

Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 851883-08-4
Cat. No. CS-0096074
Purity≥97%
MDL No.None

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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine|CS-0096074

Structure of 851883-08-4

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General Information

CAS No. 851883-08-4
Cat. No. CS-0096074
Purity ≥97%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₉BN₂O₂
Molecular Weight 234.10
Synonym(s) 4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diaMine
SMILES NC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1N

Description

This boronate-functionalized diamine integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, offering enhanced stability and reactivity. The tetramethyl-1,3,2-dioxaborolane moiety enables efficient C–C bond formation under mild conditions, while the para-aminophenyl scaffold provides a robust platform for downstream derivatization in medicinal chemistry and materials synthesis.

Application

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient coupling with aryl halides under mild conditions, while the ortho-diamine functionality provides orthogonal reactivity for metal coordination and downstream heterocycle formation. Bench-stable and readily purified by chromatography, it facilitates rapid access to substituted biaryl scaffolds and functionalized aromatic systems relevant to medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  833486-94-5
- ~92%
- In-stock
  
  851883-08-4
References
- Hubbard, Robert D.; Bamaung, Nwe Y.; Fidanze, Steve D.; Erickson, Scott A.; Palazzo, Fabio; Wilsbacher, Julie L.; Zhang, Qian; Tucker, Lora A.; Hu, Xiaoming; Kovar, Peter; Osterling, Donald J.; Johnson, Eric F.; Bouska, Jennifer; Wang, Jieyi; Davidsen, Steven K.; Bell, Randy L.; Sheppard, George S. Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 6 p. 1718 - 1721
Route2
- In-stock
  
  1575-37-7
- In-stock
  
  73183-34-3
- ~85%
- In-stock
  
  851883-08-4
References
- Liu, Shih-Yuan; Nocera, Daniel G. Journal of the American Chemical Society, 2005 , vol. 127, # 15 p. 5278 - 5279
Route3
- 849236-22-2
- ~%
- In-stock
  
  851883-08-4
References
- MERCK and CO., INC. Patent: WO2009/14620 A1, 2009 ; Location in patent: Page/Page column 43; 23 ; WO 2009/014620 A1

Safety Information

Download SDS

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

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Computational Chemistry Data

TPSA 70.5
LogP 1.1502
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine

CAS No. 851883-08-4

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