2050-89-7

Basic information

• Product Name: 1,1'-biphenyl-3,3'-diamine
• Synonyms: 1,1'-biphenyl-3,3'-diamine;1,1'-biphenyl-3,3'-diamine dihydrochloride
• CAS NO: 2050-89-7
• Molecular Formula: C₁₂H₁₂N₂
• Molecular Weight: 184.24
• Mol File: 2050-89-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 93.5°C
• Boiling Point: 308.2°C (rough estimate)
• Flash Point: 254.6°C
• Appearance: /
• Density: 1.1160 (rough estimate)
• Refractive Index: 1.6266 (estimate)
• PKA: 4.72±0.10(Predicted)
• Water Solubility: 11g/L(100 oC)
• CAS DataBase Reference: 1,1'-biphenyl-3,3'-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-biphenyl-3,3'-diamine(2050-89-7)
• EPA Substance Registry System: 1,1'-biphenyl-3,3'-diamine(2050-89-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 2050-89-7(Hazardous Substances Data)

Usage

General Description

1,1'-biphenyl-3,3'-diamine, also known as 3,3'-diaminobiphenyl, is an organic compound that consists of a biphenyl ring system with amino groups attached at the 3rd and 3rd' positions. It is a white to light brown powder that is insoluble in water and soluble in organic solvents. This chemical is commonly used as an intermediate in the production of dyes, polymers, and rubber antioxidants. It is also utilized in the synthesis of pharmaceuticals and agrochemicals. However, 1,1'-biphenyl-3,3'-diamine is known to be toxic and can cause skin and eye irritation, as well as respiratory and digestive tract irritation if inhaled or ingested. Therefore, proper safety precautions should be taken when handling this chemical.

Upstream product

• 30418-59-8 3-Aminophenylboronic acid 
• 108-42-9 3-chloro-aniline 
• 106-49-0 p-toluidine 
• 108-85-0 1-bromocyclohexane 

Downstream Products

• 100-26-5 Pyridine-2,5-dicarboxylic acid 
• 1354789-58-4 C₄₈H₃₈N₄ 
• 136905-61-8 N³,N³,N^3',N^3'-Tetrakis-(4-methoxy-phenyl)-biphenyl-3,3'-diamine 
• 16400-51-4 3,3'-dibromobiphenyl 
• 31037-00-0 3,3'-diiodobiphenyl 

Relevant articles and documents

Electrospray ionization mass spectrometry detection of intermediates in the palladium-catalyzed oxidative self-coupling of areneboronic acids

Several intermediates of the oxidative coupling of areneboronic acids to afford biaryls have been identified by electrospray ionization mass spectrometry. Knowledge has been gained about the steps occurring after the biaryl formation and leading to the recovery of the catalytic species.

Preparation, structure, and reactivity of nonstabilized organoiron compounds. Implications for iron-catalyzed cross coupling reactions

A series of unprecedented organoiron complexes of the formal oxidation states -2, 0, +1, +2, and +3 is presented, which are largely devoid of stabilizing ligands and, in part, also electronically unsaturated (14-, 16-, 17- and 18-electron counts). Specifically, it is shown that nucleophiles unable to undergo β-hydride elimination, such as MeLi, PhLi, or PhMgBr, rapidly reduce Fe(3+) to Fe(2+) and then exhaustively alkylate the metal center. The resulting homoleptic organoferrate complexes [(Me4Fe)(MeLi)] [Li(OEt2)]2 (3) and [Ph4Fe][Li(Et 2O)2][Li(1,4-dioxane)] (5) could be characterized by X-ray crystal structure analysis. However, these exceptionally sensitive compounds turned out to be only moderately nucleophilic, transferring their organic ligands to activated electrophiles only, while being unable to alkylate (hetero)aryl halides unless they are very electron deficient. In striking contrast, Grignard reagents bearing alkyl residues amenable to β-hydride elimination reduce FeXn (n = 2, 3) to clusters of the formal composition [Fe(MgX)2]n. The behavior of these intermetallic species can be emulated by structurally well-defined lithium ferrate complexes of the type [Fe(C2H4) 4][Li(tmeda)]2 (8), [Fe(cod)2][Li(dme)] 2 (9), [CpFe(C2H4)2][Li(tmeda)] (7), [CpFe(cod)][Li(dme)] (11), or [Cp*Fe(C2H4) 2][Li(tmeda)] (14). Such electron-rich complexes, which are distinguished by short intermetallic Fe-Li bonds, were shown to react with aryl chlorides and allyl halides; the structures and reactivity patterns of the resulting organoiron compounds provide first insights into the elementary steps of low valent iron-catalyzed cross coupling reactions of aryl, alkyl, allyl, benzyl, and propargyl halides with organomagnesium reagents. However, the acquired data suggest that such C-C bond formations can occur, a priori, along different catalytic cycles shuttling between metal centers of the formal oxidation states Fe(+1)/Fe(+3), Fe(0)/Fe(+2), and Fe(-2)/Fe(0). Since these different manifolds are likely interconnected, an unambiguous decision as to which redox cycle dominates in solution remains difficult, even though iron complexes of the lowest accessible formal oxidation states promote the reactions most effectively.