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4-Benzyloxybenzylamine, also known as N-(4-benzyloxyphenyl)methanamine, is an aromatic amine belonging to the class of organic compounds known as anilines. It features a benzyl group attached to the amino group, making it a versatile and valuable compound in various fields of chemistry and industry due to its chemical structure and properties.

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  • 22171-15-9 Structure
  • Basic information

    1. Product Name: 4-Benzyloxybenzylamine
    2. Synonyms: (4-(Benzyloxy)phenyl)methanamine;[4-(Benzyloxy)phenyl]methylamine;(4-phenylmethoxyphenyl)methanamine
    3. CAS NO:22171-15-9
    4. Molecular Formula: C14H15NO
    5. Molecular Weight: 213.28
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 22171-15-9.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 4-Benzyloxybenzylamine(CAS DataBase Reference)
    10. NIST Chemistry Reference: 4-Benzyloxybenzylamine(22171-15-9)
    11. EPA Substance Registry System: 4-Benzyloxybenzylamine(22171-15-9)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 22171-15-9(Hazardous Substances Data)

22171-15-9 Usage

Uses

Used in Pharmaceutical Industry:
4-Benzyloxybenzylamine is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs and medicinal compounds.
Used in Organic Compounds Synthesis:
It serves as a building block in the preparation of various advanced materials and chemical products, highlighting its utility in creating complex organic molecules.
Used in Production of Dyes and Industrial Chemicals:
4-Benzyloxybenzylamine is utilized in the production of dyes and other important industrial chemicals, showcasing its wide range of applications across different sectors.

Check Digit Verification of cas no

The CAS Registry Mumber 22171-15-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,1,7 and 1 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 22171-15:
(7*2)+(6*2)+(5*1)+(4*7)+(3*1)+(2*1)+(1*5)=69
69 % 10 = 9
So 22171-15-9 is a valid CAS Registry Number.

22171-15-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (4-phenylmethoxyphenyl)methanamine

1.2 Other means of identification

Product number -
Other names 4-Benzyloxybenzylamine

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:22171-15-9 SDS

22171-15-9Relevant articles and documents

Reusable Co-nanoparticles for general and selectiveN-alkylation of amines and ammonia with alcohols

Beller, Matthias,Gawande, Manoj B.,Jagadeesh, Rajenahally V.,Kadam, Ravishankar G.,Li, Xinmin,Ma, Zhuang,Petr, Martin,Zbo?il, Radek,Zhou, Bei

, p. 111 - 117 (2022/01/06)

A general cobalt-catalyzedN-alkylation of amines with alcohols by borrowing hydrogen methodology to prepare different kinds of amines is reported. The optimal catalyst for this transformation is prepared by pyrolysis of a specific templated material, which is generatedin situby mixing cobalt salts, nitrogen ligands and colloidal silica, and subsequent removal of silica. Applying this novel Co-nanoparticle-based material, >100 primary, secondary, and tertiary amines includingN-methylamines and selected drug molecules were conveniently prepared starting from inexpensive and easily accessible alcohols and amines or ammonia.

A State-of-the-Art Heterogeneous Catalyst for Efficient and General Nitrile Hydrogenation

Formenti, Dario,Mocci, Rita,Atia, Hanan,Dastgir, Sarim,Anwar, Muhammad,Bachmann, Stephan,Scalone, Michelangelo,Junge, Kathrin,Beller, Matthias

supporting information, p. 15589 - 15595 (2020/10/02)

Cobalt-doped hybrid materials consisting of metal oxides and carbon derived from chitin were prepared, characterized and tested for industrially relevant nitrile hydrogenations. The optimal catalyst supported onto MgO showed, after pyrolysis at 700 °C, magnesium oxide nanocubes decorated with carbon-enveloped Co nanoparticles. This special structure allows for the selective hydrogenation of diverse and demanding nitriles to the corresponding primary amines under mild conditions (e.g. 70 °C, 20 bar H2). The advantage of this novel catalytic material is showcased for industrially important substrates, including adipodinitrile, picolinonitrile, and fatty acid nitriles. Notably, the developed system outperformed all other tested commercial catalysts, for example, Raney Nickel and even noble-metal-based systems in these transformations.

General and selective synthesis of primary amines using Ni-based homogeneous catalysts

Beller, Matthias,Chandrashekhar, Vishwas G.,Jagadeesh, Rajenahally V.,Jiao, Haijun,Murugesan, Kathiravan,Wei, Zhihong

, p. 4332 - 4339 (2020/05/18)

The development of base metal catalysts for industrially relevant amination and hydrogenation reactions by applying abundant and atom economical reagents continues to be important for the cost-effective and sustainable synthesis of amines which represent highly essential chemicals. In particular, the synthesis of primary amines is of central importance because these compounds serve as key precursors and central intermediates to produce value-added fine and bulk chemicals as well as pharmaceuticals, agrochemicals and materials. Here we report a Ni-triphos complex as the first Ni-based homogeneous catalyst for both reductive amination of carbonyl compounds with ammonia and hydrogenation of nitroarenes to prepare all kinds of primary amines. Remarkably, this Ni-complex enabled the synthesis of functionalized and structurally diverse benzylic, heterocyclic and aliphatic linear and branched primary amines as well as aromatic primary amines starting from inexpensive and easily accessible carbonyl compounds (aldehydes and ketones) and nitroarenes using ammonia and molecular hydrogen. This Ni-catalyzed reductive amination methodology has been applied for the amination of more complex pharmaceuticals and steroid derivatives. Detailed DFT computations have been performed for the Ni-triphos based reductive amination reaction, and they revealed that the overall reaction has an inner-sphere mechanism with H2metathesis as the rate-determining step.

Ultra-small cobalt nanoparticles from molecularly-defined Co-salen complexes for catalytic synthesis of amines

Beller, Matthias,Chandrashekhar, Vishwas G.,Gawande, Manoj B.,Jagadeesh, Rajenahally V.,Kalevaru, Narayana V.,Kamer, Paul C. J.,Senthamarai, Thirusangumurugan,Zbo?il, Radek

, p. 2973 - 2981 (2020/03/27)

We report the synthesis of in situ generated cobalt nanoparticles from molecularly defined complexes as efficient and selective catalysts for reductive amination reactions. In the presence of ammonia and hydrogen, cobalt-salen complexes such as cobalt(ii)-N,N′-bis(salicylidene)-1,2-phenylenediamine produce ultra-small (2-4 nm) cobalt-nanoparticles embedded in a carbon-nitrogen framework. The resulting materials constitute stable, reusable and magnetically separable catalysts, which enable the synthesis of linear and branched benzylic, heterocyclic and aliphatic primary amines from carbonyl compounds and ammonia. The isolated nanoparticles also represent excellent catalysts for the synthesis of primary, secondary as well as tertiary amines including biologically relevant N-methyl amines.

Hitting on the move: Targeting intrinsically disordered protein states of the MDM2-p53 interaction

Neochoritis, Constantinos G.,Atmaj, Jack,Twarda-Clapa, Aleksandra,Surmiak, Ewa,Skalniak, Lukasz,K?hler, Lisa-Maria,Muszak, Damian,Kurpiewska, Katarzyna,Kalinowska-T?u?cik, Justyna,Beck, Barbara,Holak,D?mling, Alexander

supporting information, (2019/08/20)

Intrinsically disordered proteins are an emerging class of proteins without a folded structure and currently disorder-based drug targeting remains a challenge. p53 is the principal regulator of cell division and growth whereas MDM2 consists its main negative regulator. The MDM2-p53 recognition is a dynamic and multistage process that amongst other, employs the dissociation of a transient α-helical N-terminal ‘‘lid’’ segment of MDM2 from the proximity of the p53-complementary interface. Several small molecule inhibitors have been reported to inhibit the formation of the p53-MDM2 complex with the vast majority mimicking the p53 residues Phe19, Trp23 and Leu26. Recently, we have described the transit from the 3-point to 4-point pharmacophore model stabilizing this intrinsically disordered N-terminus by increasing the binding affinity by a factor of 3. Therefore, we performed a thorough SAR analysis, including chiral separation of key compound which was evaluated by FP and 2D NMR. Finally, p53-specific anti-cancer activity towards p53-wild-type cancer cells was observed for several representative compounds.

An Inhospitable Cryptand: The Importance of Conformational Freedom in Host-Guest Complexation

Gibson, Harry W.,Huang, Feihe,Zhao, Run,Shao, Li,Zakharov, Lev N.,Slebodnick, Carla,Rheingold, Arnold L.

, p. 3472 - 3479 (2019/03/27)

Two new cryptands were synthesized from bis(5-bromomethyl-1,3-phenylene)-32-crown-10 (4). The third arms, containing 19 or 21 atoms, were installed via Williamson ether syntheses with bisphenols containing 2,6-disubstituted pyridines. 2,6-Diaminopyridine

Cobalt-based nanoparticles prepared from MOF-carbon templates as efficient hydrogenation catalysts

Murugesan, Kathiravan,Senthamarai, Thirusangumurugan,Sohail, Manzar,Alshammari, Ahmad S.,Pohl, Marga-Martina,Beller, Matthias,Jagadeesh, Rajenahally V.

, p. 8553 - 8560 (2018/11/30)

The development of efficient and selective nanostructured catalysts for industrially relevant hydrogenation reactions continues to be an actual goal of chemical research. In particular, the hydrogenation of nitriles and nitroarenes is of importance for the production of primary amines, which constitute essential feedstocks and key intermediates for advanced chemicals, life science molecules and materials. Herein, we report the preparation of graphene shell encapsulated Co3O4- and Co-nanoparticles supported on carbon by the template synthesis of cobalt-terephthalic acid MOF on carbon and subsequent pyrolysis. The resulting nanoparticles create stable and reusable catalysts for selective hydrogenation of functionalized and structurally diverse aromatic, heterocyclic and aliphatic nitriles, and as well as nitro compounds to primary amines (>65 examples). The synthetic and practical utility of this novel non-noble metal-based hydrogenation protocol is demonstrated by upscaling several reactions to multigram-scale and recycling of the catalyst.

Switching the Selectivity of Cobalt-Catalyzed Hydrogenation of Nitriles

Dai, Huiguang,Guan, Hairong

, p. 9125 - 9130 (2018/09/21)

Previous studies of base metals for catalytic hydrogenation of nitriles to primary amines or secondary aldimines focus on designing complexes with elaborate structures. Herein, we report "twin" catalytic systems where the selectivity of nitrile hydrogenation can be tuned by including or omitting the ligand HN(CH2CH2PiPr2)2 (iPrPNHP). Simply treating CoBr2 with NaHBEt3 generates cobalt particles, which can catalyze the hydrogenation of nitriles to primary amines with high selectivity and broad functional group tolerance. Ligating CoBr2 with iPrPNHP followed by the addition of NaHBEt3, however, forms a homogeneous catalyst favoring secondary aldimines for both hydrogenation and hydrogenative coupling of benzonitrile.

Design and synthesis of neolamellarin a derivatives targeting heat shock protein 90

Jiang, Long,Yin, Ruijuan,Wang, Xueting,Dai, Jiajia,Li, Jing,Jiang, Tao,Yu, Rilei

supporting information, p. 24 - 33 (2017/04/21)

In this study, we designed and synthesized a novel family of neolamellarin A derivatives that showed high inhibitory activity toward heat shock protein 90 (Hsp90), a kinase associated with cell proliferation. The 3,4-bis(catechol)pyrrole scaffold and the benzyl group with methoxy modification at N position of pyrrole are essential to the Hsp90 inhibitory activity and cytotoxicity of these compounds. Western blot analysis demonstrated that these compounds induced dramatic depletion of the examined client proteins of Hsp90, and accelerated cancer cell apoptosis. Docking simulations suggested that the binding mode of 9p was similar to that of the VER49009, a potent inhibitor of Hsp90. Further molecular dynamics simulation indicated that the hydrophobic interactions as well as the hydrogen bonds contributed to the high affinity of 9p to Hsp90.

MOF-derived cobalt nanoparticles catalyze a general synthesis of amines

Jagadeesh, Rajenahally V.,Murugesan, Kathiravan,Alshammari, Ahmad S.,Neumann, Helfried,Pohl, Marga-Martina,Radnik, J?rg,Beller, Matthias

, p. 326 - 332 (2017/09/28)

The development of base metal catalysts for the synthesis of pharmaceutically relevant compounds remains an important goal of chemical research. Here, we report that cobalt nanoparticles encapsulated by a graphitic shell are broadly effective reductive amination catalysts. Their convenient and practical preparation entailed template assembly of cobaltdiamine- dicarboxylic acid metal organic frameworks on carbon and subsequent pyrolysis under inert atmosphere.The resulting stable and reusable catalysts were active for synthesis of primary, secondary, tertiary, and N-methylamines (more than 140 examples).The reaction couples easily accessible carbonyl compounds (aldehydes and ketones) with ammonia, amines, or nitro compounds, and molecular hydrogen under industrially viable and scalable conditions, offering cost-effective access to numerous amines, amino acid derivatives, and more complex drug targets.

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