90-41-5

Basic information

• Product Name: 2-Aminodiphenyl
• Synonyms: 2-amino-1,1’-biphenyl;2-Aminobifenyl;2-aminobiphenyl(forsugardetermination);2-Phenylbenzenamine;biphenyl,2-amino-;NCI-C50282;ortho-Amino-biphenyl;2-PHENYLANILIN
• CAS NO: 90-41-5
• Molecular Formula: C₁₂H₁₁N
• Molecular Weight: 169.22
• EINECS: 201-990-9
• Product Categories: Amines and Anilines;Biphenyl & Diphenyl ether;Amines;Aromatics;Mutagenesis Research Chemicals
• Mol File: 90-41-5.mol

Chemical Properties

• Melting Point: 47-50 °C(lit.)
• Boiling Point: 299 °C(lit.)
• Flash Point: >230 °F
• Appearance: Purple to brown/Crystals or Crystalline Powder
• Density: 1.44
• Vapor Density: 5.9 (vs air)
• Vapor Pressure: 2 mm Hg ( 140 °C)
• Refractive Index: 1.613-1.615
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 3.82(at 22℃)
• Water Solubility: <0.01 g/100 mL at 21℃
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 471874
• CAS DataBase Reference: 2-Aminodiphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminodiphenyl(90-41-5)
• EPA Substance Registry System: 2-Aminodiphenyl(90-41-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-40-52/53-21/22/36/37/38/40-20
• Safety Statements: 36/37-61
• WGK Germany: 3
• RTECS: DV5530000
• TSCA: Yes
• Hazardous Substances Data: 90-41-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Aminobiphenyl is utilized as a substrate for UDP-glucuronosyltransferases (UGTs), a group of enzymes that play a crucial role in the metabolism and detoxification of various compounds in the body. Specifically, it is used for UGT1A4, UGT2B13, and UGT2B16, which are involved in the glucuronidation process, thereby aiding in the elimination of drugs and other substances.
Used in Chemical Catalysts:
In the field of organic chemistry, 2-aminobiphenyl is employed in the synthesis of palladacycles, which are popular catalysts for cross-coupling reactions. These reactions are essential for the formation of carbon-carbon bonds, a fundamental aspect of constructing complex organic molecules, including pharmaceuticals and agrochemicals.
Used in Toxicology Research:
2-Aminobiphenyl has been identified as having mutagenic potency, making it a subject of interest in toxicology research. Studying its effects can provide insights into the mechanisms of mutagenicity and contribute to the development of safer chemicals and compounds.

Preparation

2-Aminodiphenyl is prepared by hydrogenation of 2-nitrobiphenyl.NEW SYNTHESIS OF 2-AMINOBIPHENYLSReflux 2-nitrobiphenyl, ethanol and stannous chloride in a water bath for 3h, recover the ethanol, cool the residue, add 40% liquid alkali to make it strongly alkaline, separate the oil layer, extract the aqueous layer with ether, dry the extract with anhydrous calcium chloride, filter and recover the ether, wash with ethanol to obtain the crude product, then distill the crude product under reduced pressure to obtain 2-aminobiphenyl.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 5, p. 829, 1973Tetrahedron Letters, 36, p. 125, 1995 DOI: 10.1016/0040-4039(94)02191-D

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Aminodiphenyl neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.

Hazard

Toxic by ingestion, inhalation, and skin absorption. A carcinogen.

Fire Hazard

2-Aminodiphenyl is probably combustible.

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by ingestion.Mutation data reported. When heated to decomposition, itemits toxic fumes of NOx.

Purification Methods

Crystallise it from aqueous EtOH (charcoal). [Beilstein 12 IV 3223.]

InChI:InChI=1/C12H11N/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9H,13H2

Upstream product

• 86-00-0 2-nitrobiphenyl 
• 13234-79-2 2-phenylbenzamide 
• 62-53-3 aniline 
• 622-37-7 Phenyl azide 
• 297766-64-4 1,3-Diphenyltriazen 
• 92-52-4 biphenyl 
• 1493-13-6 trifluorormethanesulfonic acid 
• 7599-23-7 2-azidobiphenyl 
• 201230-82-2 carbon monoxide 
• 56923-15-0 1-hydroxyimino-2-phenyl-2-cyclohexene 
• 21711-71-7 2-phenylnitrosobenzene 
• 100314-24-7 2-cyclohexylidene-cyclohexanol 
• 2350-10-9 N-chloro-N-methyl-4-toluene sulphonamide 
• 82084-29-5 C₁₃H₁₃N₃ 

Downstream Products

• 80584-50-5 N-biphenyl-succinimide 
• 288843-63-0 thiophene-2-carboxylic acid biphenyl-2-ylamide 
• 54893-50-4 2-phenanthridin-6-yl-benzoic acid 
• 14835-59-7 2-(biphenyl-2-yl)-1H-isoindole-1,3(2H)-dione 
• 500345-76-6 2-(4-chloro-phenyl)-8-phenyl-quinoline-4-carboxylic acid 
• 94998-30-8 2-chloro-benzoic acid biphenyl-2-ylamide 
• 854860-81-4 2,8-diphenyl-quinoline-4-carboxylic acid 
• 52648-48-3 N-(phenylmethyl)-(1,1'-biphenyl)-2-amine 
• 7404-97-9 2-(benzoylamino)biphenyl 
• 13114-83-5 N-biphenyl-2-yl-N'-phenyl-urea 
• 871877-03-1 N,N'-bis-biphenyl-2-yl-thiourea 
• 17337-13-2 [1,1'-biphenyl]-2-yl-isocyanate 
• 86-74-8 9H-carbazole 
• 5346-21-4 N-formyl-2-aminobiphenyl 

Relevant articles and documents

Novel iota carrageenan-based RhCl3 as an efficient and recyclable catalyst in Suzuki cross coupling

RhCl3 was heterogenized into renewable polysaccharide supports, and the effect of polysaccharide type on the new catalyst performances in a Suzuki cross-coupling reaction was studied. The conversion of the fresh iota carrageenan heterogeneous system (?-RhCl3), was found to be the highest, whereas it was lower than the conversion of its homogeneous analogue. In addition, the ?-RhCl3 (catalyst loading of 6.5 % wt) was proven to be efficient heterogeneous catalyst that was easily recycled, whereas the conversion was increased in the first and second cycles. Scanning electronic microscopy (SEM) combining Energy dispersive X-ray spectrometry and Surface analysis by X-ray photoelectron spectroscopy were performed, confirming that RhCl3 was embedded within the ?-carrageenan. The Fourier-transform infrared spectrometry of the heterogeneous ?-RhCl3 catalyst was compared to that of the native polysaccharide, and no new bands were detected. Nonetheless, a comparison of SEM image of ?-carrageenan with and without RhCl3, as well as rheological measurements of the aqueous solution of ? with and without RhCl3, indicated the incorporation of the polysaccharide with the RhCl3.

Biosynthesis of poly(ethylene glycol)-supported palladium nanoparticles using Colocasia esculenta leaf extract and their catalytic activity for Suzuki-Miyaura cross-coupling reactions

A simple and green protocol for the synthesis of poly(ethylene glycol) stabilized palladium nanoparticles under ambient conditions from the aqueous extracts of Colocasia esculenta leaves has been reported. The nanoparticles are characterized using UV-visible spectroscopy, FTIR spectroscopy, XRD and SEM analysis. The prepared Pd NPs showed excellent catalytic activity towards Suzuki-Miyaura cross coupling reactions for a wide variety of aryl halides and phenyl boronic acid substrates. The catalytic system was found to be recyclable and could be reused in subsequent catalytic runs without significant loss of activity.

Pd nanoparticles in hollow magnetic mesoporous spheres: High activity, and magnetic recyclability

The nanoreactor of hollow magnetic mesoporous silica spheres (Pd/HMMS), with Pd and Fe3O4 nanoparticles embedded in the mesoporous silica shell, were successfully prepared by using the colloidal carbon spheres of glucose, Pd and Fe3O4 heteroaggregates as the hard template together with a coating of tetraethoxysilane (TEOS) and cetyltrimethylammonium bromide (CTAB) mixture. The synthesized Pd/HMMS shows excellent catalytic activity in the Suzuki cross-coupling reaction of iodobenzene with phenylboronic acid with over 99% yield in 3 min and can be recycled multiple times without any significant loss in catalytic activity.

Pd-Cu alloy nanoparticle supported on amine-terminated ionic liquid functional 3D graphene and its application on Suzuki cross-coupling reaction

Well distributed Pd-Cu bimetallic alloy nanoparticles supported on amine-terminated ionic liquid functional three-dimensional graphene (3D IL-rGO/Pd-Cu) as an efficient catalyst for Suzuki cross-coupling reaction has been prepared via a facile synthetic method. The introduction of IL-NH2 cations on the surface of graphene sheets can effectively avoid the re-deposition of graphene sheets, allowing the catalyst to be reused up to 10?cycles. The addition of Cu not only saves cost but also ensures high catalytic efficiency. It is worthy to note that the catalyst 3D IL-rGO/Pd2.5Cu2.5 can efficiently catalyze the Suzuki cross-coupling reaction with the yield up to 100% in 0.25?h, almost one-fold higher than that by the pristine IL-rGO/Pd2.5 catalyst (52%). The Powder X-Ray Diffraction (XRD), combining energy dispersive X-ray spectroscopy (EDS) mapping results confirm the existence and distribution of Pd and Cu in the bimetallic nanoparticles. The transmission electron microscopy (TEM) reveals the nanoparticle size with an average diameter of 3.0?±?0.5?nm. X-ray photoelectron spectroscopy (XPS) analysis proved the presence of electron transfer from Cu to Pd upon alloying. Such alloying-induced electronic modification of Pd-Cu alloy and 3D ionic liquid functional graphene with large specific surface area both accounted for the catalytic enhancement.

A selective luminescent probe for the direct time-gated detection of adenosine triphosphate

A molecular probe for the luminescent detection of adenosine nucleotides is presented. The probe, Tb-DOTAm-Phen, readily distinguishes among the three adenosine nucleotides in buffered aqueous conditions at neutral pH, a requirement for the direct monitoring of enzymatic reactions converting adenosine triphosphate (ATP) to adenosine diphosphate or adenosine monophosphate. The probe is most efficient under millimolar concentrations of ATP which are relevant to intracellular conditions. Moreover, the long luminescence lifetime of the probe readily enables time-gating experiments.

A Convenient and Stable Heterogeneous Nickel Catalyst for Hydrodehalogenation of Aryl Halides Using Molecular Hydrogen

Hydrodehalogenation is an effective strategy for transforming persistent and potentially toxic organohalides into their more benign congeners. Common methods utilize Pd/C or Raney-nickel as catalysts, which are either expensive or have safety concerns. In this study, a nickel-based catalyst supported on titania (Ni-phen@TiO2-800) is used as a safe alternative to pyrophoric Raney-nickel. The catalyst is prepared in a straightforward fashion by deposition of nickel(II)/1,10-phenanthroline on titania, followed by pyrolysis. The catalytic material, which was characterized by SEM, TEM, XRD, and XPS, consists of nickel nanoparticles covered with N-doped carbon layers. By using design of experiments (DoE), this nanostructured catalyst is found to be proficient for the facile and selective hydrodehalogenation of a diverse range of substrates bearing C?I, C?Br, or C?Cl bonds (>30 examples). The practicality of this catalyst system is demonstrated by the dehalogenation of environmentally hazardous and polyhalogenated substrates atrazine, tetrabromobisphenol A, tetrachlorobenzene, and a polybrominated diphenyl ether (PBDE).

Synthesis of Stannylated Aryl Imines and Amines via Aryne Insertion Reactions into Sn?N Bonds

The reaction of in situ generated arynes with stannylated imines to provide ortho-stannyl-aniline derivatives is reported. The readily prepared trimethylstannyl benzophenone imine is introduced as an efficient reagent to realize the aryne σ-insertion reaction. The imine functionality is an established N-protecting group and insertions proceed with good yields and good to excellent regioselectivities. The product anilines are valuable starting materials for follow-up chemistry thanks to the rich chemistry offered by the trimethylstannyl moiety.

Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C-Ethylene System and Its Application to Indole Synthesis

The synthesis of anilines and indoles from cyclohexanones using a Pd/C-ethylene system is reported. A simple combination of NH4OAc and K2CO3 under nonaerobic conditions was found to be the most suitable to perform this reaction. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.

Selective primary aniline synthesis through supported Pd-catalyzed acceptorless dehydrogenative aromatization by utilizing hydrazine

By utilizing hydrazine (N2H4) as the nitrogen source in the presence of a hydroxyapatite-supported Pd nanoparticle catalyst (Pd/HAP), various primary anilines can be selectively synthesized from cyclohexanonesviaacceptorless dehydrogenative aromatization. The strong nucleophilicity of N2H4and the stability of the hydrazone intermediates can effectively suppress the formation of the undesired secondary aniline byproducts.

NaI/PPh3-Mediated Photochemical Reduction and Amination of Nitroarenes

A mild transition-metal- and photosensitizer-free photoredox system based on the combination of NaI and PPh3 was found to enable highly selective reduction of nitroarenes. This protocol tolerates a broad range of reducible functional groups such as halogen (Cl, Br, and even I), aldehyde, ketone, carboxyl, and cyano. Moreover, the photoredox catalysis with NaI and stoichiometric PPh3 provides also an alternative entry to Cadogan-type reductive amination when o-nitrobiarenes were used.