[1,1'-Biphenyl]-2,2'-diamine

Name: [1,1'-Biphenyl]-2,2'-diamine
Brand: ChemScene
Availability: InStock
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CAS No. 1454-80-4
Cat. No. CS-0196799
Purity≥98%
MDL No.None

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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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General Information

CAS No. 1454-80-4
Cat. No. CS-0196799
Purity ≥98%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₂N₂
Molecular Weight 184.24
Synonym(s) 2,2-Biphenyldiamine
SMILES C1=CC=C(C(=C1)C2=CC=CC=C2N)N

Description

1,1'-Biphenyl]-2,2'-diamine features two amino groups positioned ortho to the biphenyl linkage, creating a rigid, electron-rich scaffold ideal for coordination in transition metal catalysis. The diamine integrates readily into chiral ligands, offering enhanced stability and defined stereocontrol in asymmetric synthesis.

Application

[1,1'-Biphenyl]-2,2'-diamine serves as a versatile bifunctional scaffold in transition metal catalysis and ligand design. Its ortho-diamine architecture enables stable chelation with palladium, copper, and nickel complexes, facilitating cross-coupling reactions under mild conditions. The molecule exhibits good bench stability, tolerates diverse functional groups, and simplifies purification due to its crystalline nature, making it a practical building block for catalyst development and synthetic methodology.

Synthesis

Route1
- 2436-96-6
- ~97%
- In-stock
  
  1454-80-4
References
- Stahl, Shannon S.; Scarborough, Christopher C. Patent: US2006/229448 A1, 2006 ; Location in patent: Page/Page column 4; 7 ;
Route2
- 609-73-4
- In-stock
  
  5570-18-3
- ~24%
- In-stock
  
  1454-80-4
- 35883-86-4
References
- Journal of Organic Chemistry, , vol. 70, # 23 p. 9591 - 9594
Route3
- In-stock
  
  615-43-0
- In-stock
  
  5570-19-4
- ~35%
- 2436-96-6
- In-stock
  
  1454-80-4
- 35883-86-4
References
- Journal of Organic Chemistry, , vol. 70, # 23 p. 9591 - 9594

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05,GHS09
Signal Word : Danger	UN#: 3077
Class : 9	Packing Group : Ⅲ
Hazard Statements : H302-H318-H400
Precautionary Statements : P264-P270-P273-P280-P305+P351+P338-P330-P391-P501

Quality Control

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Computational Chemistry Data

TPSA 52.04
LogP 2.518
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Material Science Material Building Blocks Small Molecule Semiconductor Building Blocks Biphenyls

Key Words

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[1,1'-Biphenyl]-2,2'-diamine

CAS No. 1454-80-4

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