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90-41-5

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90-41-5 Usage

Description

2-Aminobiphenyl (2-APB) is an organic compound with the formula C6H5C6H4NH2. It is an amine derivative of biphenyl. It is a colorless solid, although aged samples can appear colored even black. Palladacycles obtained from 2-aminobiphenyl are popular catalysts for cross-coupling.

Chemical Properties

colourless to purple crystalline solid. Soluble in alcohol, ether and benzene, insoluble in water. Can be volatilized with water vapor. Flash point >110℃.

Uses

2-Aminobiphenyl has a mutagenic potency. It is a substrate for UGTs (UDP-glucuronosyltransferases), including UGT1A4, UGT2B13 and UGT2B16.

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.

Application

2-Aminobiphenyl is used as raw materials for organic synthesis. manufacture of carbazole resin, synthetic rubber.

Synthesis Reference(s)

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

General Description

2-aminobiphenyl appears as colorless or purplish crystals. (NTP, 1992)

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 90-41-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 0 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 90-41:
(4*9)+(3*0)+(2*4)+(1*1)=45
45 % 10 = 5
So 90-41-5 is a valid CAS Registry Number.
InChI:InChI=1/C12H11N/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9H,13H2

90-41-5 Well-known Company Product Price

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  • Alfa Aesar

  • (L05728)  2-Aminobiphenyl, 97%   

  • 90-41-5

  • 1g

  • 244.0CNY

  • Detail
  • Alfa Aesar

  • (L05728)  2-Aminobiphenyl, 97%   

  • 90-41-5

  • 5g

  • 608.0CNY

  • Detail

90-41-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Aminodiphenyl

1.2 Other means of identification

Product number -
Other names 2-phenylaniline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:90-41-5 SDS

90-41-5Relevant articles and documents

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

Leviev, Sivan,Levy-Ontman, Oshrat,Wolfson, Adi

, (2020)

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.

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

Sun, Jian,Dong, Zhengping,Sun, Xun,Li, Ping,Zhang, Fengwei,Hu, Wuquan,Yang, Haidong,Wang, Haibo,Li, Rong

, p. 46 - 51 (2013)

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.

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

Weitz, Evan A.,Chang, Jennifer Y.,Rosenfield, Adam H.,Pierre, Valerie C.

, p. 16099 - 16102,4 (2012)

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.

Pd-Catalysed Suzuki-Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides

Goetz, Roland,Hashmi, A. Stephen K.,Orecchia, Patrizio,Petkova, Desislava Slavcheva,Rominger, Frank,Schaub, Thomas

, p. 8169 - 8180 (2021/11/01)

The Suzuki-Miyaura coupling reaction of electron-poor aryl chlorides in the synthesis of crop protection-relevant active ingredients in water is disclosed. Optimisation of the reaction conditions allowed running the reaction with 50 ppm of Pd-catalyst loading without an additional organic solvent in the cross-coupling reaction step in short reaction times. The system was optimised for the initial cross-coupling step of the large scale produced fungicides Boscalid, Fluxapyroxad and Bixafen up to 97% yield. It is also shown that the Suzuki-Miyaura reaction can be easily scaled up to 50 g using a simple product separation and purification using environmentally benign solvents in the work-up. To show the usability of this method, it was additionally applied in the three-step synthesis of the desired active ingredients.

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

Lin, Wei-Chen,Yatabe, Takafumi,Yamaguchi, Kazuya

supporting information, p. 6530 - 6533 (2021/07/07)

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.

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