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Phenethylamine, also known as phenylethylamine, is an organic compound with the chemical formula C6H5-CH2CH2-NH2. It is an aromatic amine and a naturally occurring trace amine found in the human body. Phenethylamine plays a significant role in various physiological processes and has potential applications in the pharmaceutical industry.

64-04-0 Suppliers

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  • 64-04-0 Structure
  • Basic information

    1. Product Name: Phenethylamine
    2. Synonyms: 2-PHENYLETHYLAMINE;2-AMINOETHYLBENZENE;2-PHENETHYLAMINE;1-AMINO-2-PHENYLETHANE;AKOS BBS-00003597;3-AMINOETHYLBENZENE;LABOTEST-BB LTBB000487;FEMA 3220
    3. CAS NO:64-04-0
    4. Molecular Formula: C8H11N
    5. Molecular Weight: 121.18
    6. EINECS: 200-574-4
    7. Product Categories: Amines;Bioactive Small Molecules;Building Blocks;C8;Cell Biology;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;P;Alkaloid;Nutrition Research;Phytochemicals by Chemical Classification;Pharma material;Inhibitors;Phenethylamine
    8. Mol File: 64-04-0.mol
  • Chemical Properties

    1. Melting Point: -60 °C
    2. Boiling Point: 197-200 °C(lit.)
    3. Flash Point: 195 °F
    4. Appearance: clear, colorless/liquid
    5. Density: 0.962 g/mL at 20 °C(lit.)
    6. Vapor Density: 4.18 (vs air)
    7. Vapor Pressure: 0.398mmHg at 25°C
    8. Refractive Index: n20/D 1.533(lit.)
    9. Storage Temp.: 2-8°C
    10. Solubility: alcohol: freely soluble(lit.)
    11. PKA: 9.84(at 25℃)
    12. Explosive Limit: 1.0-5.5%(V)
    13. Water Solubility: SOLUBLE
    14. Sensitive: Air Sensitive
    15. Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong acids.
    16. Merck: 14,6026
    17. BRN: 507488
    18. CAS DataBase Reference: Phenethylamine(CAS DataBase Reference)
    19. NIST Chemistry Reference: Phenethylamine(64-04-0)
    20. EPA Substance Registry System: Phenethylamine(64-04-0)
  • Safety Data

    1. Hazard Codes: C
    2. Statements: 22-34
    3. Safety Statements: 26-36/37/39-45
    4. RIDADR: UN 2922 8/PG 2
    5. WGK Germany: 1
    6. RTECS: SG8750000
    7. F: 9-23
    8. TSCA: Yes
    9. HazardClass: 8
    10. PackingGroup: III
    11. Hazardous Substances Data: 64-04-0(Hazardous Substances Data)

64-04-0 Usage

Chemical Description

Phenethylamine is a monoamine alkaloid that is commonly used as a dietary supplement and has been investigated for its potential therapeutic uses.

Uses

Phenethylamine is used in the manufacturing of anti-depression agents and anti-diabetic drugs. It serves as an essential precursor in the synthesis of these medications, contributing to their therapeutic effects.
Used in Pharmaceutical Industry:
Phenethylamine is used as a key intermediate in the production of various pharmaceuticals. Its presence in the human body and its ability to influence physiological processes make it a valuable component in drug development.
Used in Drug Synthesis:
Phenethylamine is used as a starting material for the synthesis of other organic compounds. Its versatile chemical properties allow it to be transformed into a wide range of molecules with various applications.
Used in Drug Jiangtangling Intermediate:
Phenethylamine is utilized in the production of drug jiangtangling intermediates, which are essential components in the synthesis of certain pharmaceuticals. These intermediates play a crucial role in the development of new drugs and the improvement of existing ones.

Preparation

By reduction of benzyl cyanide with sodium metal in alcohol or with Raney-Ni.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 34, p. 3905, 1986 DOI: 10.1248/cpb.34.3905Journal of the American Chemical Society, 94, p. 6561, 1972 DOI: 10.1021/ja00773a060Tetrahedron Letters, 21, p. 1719, 1980 DOI: 10.1016/S0040-4039(00)77819-1

Safety Profile

Poison by intraperitoneal, subcutaneous, intracervical, and intravenous routes. Moderately toxic by ingestion. A strong base. A skin irritant and possible sensitizer. When heated to decomposition it emits toxic fumes of NOx. See also AMINES

Purification Methods

Distil the amine from CaH2, under reduced pressure, just before use. [Beilstein 12 H 1096, 12 IV 2453.]

Check Digit Verification of cas no

The CAS Registry Mumber 64-04-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 4 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 64-04:
(4*6)+(3*4)+(2*0)+(1*4)=40
40 % 10 = 0
So 64-04-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2

64-04-0SDS

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 2-phenylethylamine

1.2 Other means of identification

Product number -
Other names 2-Phenethylamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:64-04-0 SDS

64-04-0Relevant articles and documents

Mesoporous Metal–Metalloid Amorphous Alloys: The First Synthesis of Open 3D Mesoporous Ni-B Amorphous Alloy Spheres via a Dual Chemical Reduction Method

Kang, Yunqing,Henzie, Joel,Gu, Huajun,Na, Jongbeom,Fatehmulla, Amanullah,Shamsan, Belqes Saeed A.,Aldhafiri, Abdullah M.,Farooq, W. Aslam,Bando, Yoshio,Asahi, Toru,Jiang, Bo,Li, Hexing,Yamauchi, Yusuke

, (2020)

Selective hydrogenation of nitriles is an industrially relevant synthetic route for the preparation of primary amines. Amorphous metal–boron alloys have a tunable, glass-like structure that generates a high concentration of unsaturated metal surface atoms that serve as active sites in hydrogenation reactions. Here, a method to create nanoparticles composed of mesoporous 3D networks of amorphous nickel–boron (Ni-B) alloy is reported. The hydrogenation of benzyl cyanide to β-phenylethylamine is used as a model reaction to assess catalytic performance. The mesoporous Ni-B alloy spheres have a turnover frequency value of 11.6 h?1, which outperforms non-porous Ni-B spheres with the same composition. The bottom-up synthesis of mesoporous transition metal–metalloid alloys expands the possible reactions that these metal architectures can perform while simultaneously incorporating more Earth-abundant catalysts.

Self-Immolative Hydroxybenzylamine Linkers for Traceless Protein Modification

Rose, Douglas A.,Treacy, Joseph W.,Yang, Zhongyue J.,Ko, Jeong Hoon,Houk,Maynard, Heather D.

supporting information, p. 6050 - 6058 (2022/04/12)

Traceless self-immolative linkers are widely used for the reversible modification of proteins and peptides. This article describes a new class of traceless linkers based on ortho- or para-hydroxybenzylamines. The introduction of electron-donating substituents on the aromatic core stabilizes the quinone methide intermediate, thus providing a platform for payload release that can be modulated. To determine the extent to which the electronics affect the rate of release, we prepared a small library of hydroxybenzylamine linkers with varied electronics in the aromatic core, resulting in half-lives ranging from 20 to 144 h. Optimization of the linker design was carried out with mechanistic insights from density functional theory (DFT) and the in silico design of an intramolecular trapping agent through the use of DFT and intramolecular distortion energy calculations. This resulted in the development of a faster self-immolative linker with a half-life of 4.6 h. To demonstrate their effectiveness as traceless linkers for bioconjugation, reversible protein-polyethylene glycol conjugates with a model protein lysozyme were prepared, which had reduced protein activity but recovered ≥94% activity upon traceless release of the polymer. This new class of linkers with tunable release rates expands the traceless linkers toolbox for a variety of bioconjugation applications.

Aluminum Metal-Organic Framework-Ligated Single-Site Nickel(II)-Hydride for Heterogeneous Chemoselective Catalysis

Antil, Neha,Kumar, Ajay,Akhtar, Naved,Newar, Rajashree,Begum, Wahida,Dwivedi, Ashutosh,Manna, Kuntal

, p. 3943 - 3957 (2021/04/12)

The development of chemoselective and heterogeneous earth-abundant metal catalysts is essential for environmentally friendly chemical synthesis. We report a highly efficient, chemoselective, and reusable single-site nickel(II) hydride catalyst based on robust and porous aluminum metal-organic frameworks (MOFs) (DUT-5) for hydrogenation of nitro and nitrile compounds to the corresponding amines and hydrogenolysis of aryl ethers under mild conditions. The nickel-hydride catalyst was prepared by the metalation of aluminum hydroxide secondary building units (SBUs) of DUT-5 having the formula of Al(μ2-OH)(bpdc) (bpdc = 4,4′-biphenyldicarboxylate) with NiBr2 followed by a reaction with NaEt3BH. DUT-5-NiH has a broad substrate scope with excellent functional group tolerance in the hydrogenation of aromatic and aliphatic nitro and nitrile compounds under 1 bar H2 and could be recycled and reused at least 10 times. By changing the reaction conditions of the hydrogenation of nitriles, symmetric or unsymmetric secondary amines were also afforded selectively. The experimental and computational studies suggested reversible nitrile coordination to nickel followed by 1,2-insertion of coordinated nitrile into the nickel-hydride bond occurring in the turnover-limiting step. In addition, DUT-5-NiH is also an active catalyst for chemoselective hydrogenolysis of carbon-oxygen bonds in aryl ethers to afford hydrocarbons under atmospheric hydrogen in the absence of any base, which is important for the generation of fuels from biomass. This work highlights the potential of MOF-based single-site earth-abundant metal catalysts for practical and eco-friendly production of chemical feedstocks and biofuels.

Iridium-Triggered Allylcarbamate Uncaging in Living Cells

Gupta, Ajay,Gupta, Shalini,Mahawar, Pritam,Prasad, Puja,Sasmal, Pijus K.,Singh, Neelu

supporting information, p. 12644 - 12650 (2021/09/06)

Designing a metal catalyst that addresses the major issues of solubility, stability, toxicity, cell uptake, and reactivity within complex biological milieu for bioorthogonal controlled transformation reactions is a highly formidable challenge. Herein, we report an organoiridium complex that is nontoxic and capable of the uncaging of allyloxycarbonyl-protected amines under biologically relevant conditions and within living cells. The potential applications of this uncaging chemistry have been demonstrated by the generation of diagnostic and therapeutic agents upon the activation of profluorophore and prodrug in a controlled fashion within HeLa cells, providing a valuable tool for numerous potential biological and therapeutic applications.

Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles

Pirola, Margherita,Faverio, Chiara,Orlandi, Manuel,Benaglia, Maurizio

, p. 10247 - 10250 (2021/06/18)

A metal-free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β-substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α-functionalized nitriles were obtained with no loss of enantiomeric excess. The methodology was successfully applied to the synthesis of chiral β-cyano esters, α-aryl alkylnitriles, and TBS-protected cyanohydrins, including direct precursors of four active pharmaceutical ingredients (ibuprofen, tembamide, aegeline and denopamine).

Direct Conversion of Hydrazones to Amines using Transaminases

Carter, Eve M.,Hailes, Helen C.,Sheppard, Tom D.,Subrizi, Fabiana,Ward, John M.

, p. 4520 - 4523 (2021/09/20)

Transaminase enzymes (TAms) have been widely used for the amination of aldehydes and ketones, often resulting in optically pure products. In this work, transaminases were directly reacted with hydrazones in a novel approach to form amine products. Several substrates were investigated, including those with furan and phenyl moieties. It was determined that the amine yields increased when an additional electrophile was added to the reaction mixture, suggesting that they can sequester the hydrazine released in the reaction. Pyridoxal 5’-phosphate (PLP), a cofactor for transaminases, and polyethylene glycol (PEG)-aldehydes were both found to increase the yield of amine formed. Notably, the amination of (S)-(?)-1-amino-2-(methoxymethyl)pyrrolidine (SAMP) hydrazones gave promising results as a method to form chiral β-substituted amines in good yield.

Selective Synthesis of Symmetrical Secondary Amines from Nitriles with a Pt?CuFe/Fe3O4 Catalyst and Ammonia Borane as Hydrogen Donor

Ai, Yongjian,Guo, Rongxiu,He, GuangQi,Hu, Ze-nan,Liang, Qionglin,Liu, Lei,Niu, Dun,Sun, Hong-bin,Tian, Haimeng,Zhang, Xinyue

, p. 1783 - 1788 (2020/09/02)

Hydrogenation of nitriles is an efficient and environmentally friendly route to synthesize symmetrical secondary amines, but it usually produces a mixture of amines, imines, and hydrogenolysis by-products. Herein we report a magnetic quaternary-component Pt?CuFe/Fe3O4 nanocatalyst system for the selective synthesis of symmetrical secondary amines with ammonia borane as hydrogen donor. The catalyst with a low Pt loading (0.456 wt%) is the source of the activity, and the d-band electron transfer from Cu to Fe enhances the selectivity. This synergistic effect results in the transformation of benzonitrile to dibenzylamine with excellent conversion (up to 99 %) and nearly quantitative selectivity (up to 96 %) under mild reaction conditions, nevertheless, the reaction TOF is as high as up to 1409.9 h?1. A variety of nitriles are suitable for the synthesis of symmetrical secondary amines. More importantly, unwanted hydrogenolysis byproducts, especially toluene, is not detected at all. In addition, the catalyst is magnetically recoverable, and it can be reused up to five times.

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.

A cobalt phosphide catalyst for the hydrogenation of nitriles

Jitsukawa, Koichiro,Mitsudome, Takato,Mizugaki, Tomoo,Nakata, Ayako,Sheng, Min,Yamasaki, Jun

, p. 6682 - 6689 (2020/08/24)

The study of metal phosphide catalysts for organic synthesis is rare. We present, for the first time, a well-defined nano-cobalt phosphide (nano-Co2P) that can serve as a new class of catalysts for the hydrogenation of nitriles to primary amines. While earth-abundant metal catalysts for nitrile hydrogenation generally suffer from air-instability (pyrophoricity), low activity and the need for harsh reaction conditions, nano-Co2P shows both air-stability and remarkably high activity for the hydrogenation of valeronitrile with an excellent turnover number exceeding 58000, which is over 20- to 500-fold greater than that of those previously reported. Moreover, nano-Co2P efficiently promotes the hydrogenation of a wide range of nitriles, which include di- and tetra-nitriles, to the corresponding primary amines even under just 1 bar of H2 pressure, far milder than the conventional reaction conditions. Detailed spectroscopic studies reveal that the high performance of nano-Co2P is attributed to its air-stable metallic nature and the increase of the d-electron density of Co near the Fermi level by the phosphidation of Co, which thus leads to the accelerated activation of both nitrile and H2. Such a phosphidation provides a promising method for the design of an advanced catalyst with high activity and stability in highly efficient and environmentally benign hydrogenations. This journal is

Benzimidazole fragment containing Mn-complex catalyzed hydrosilylation of ketones and nitriles

Ganguli, Kasturi,Mandal, Adarsha,Sarkar, Bidisha,Kundu, Sabuj

, (2020/08/13)

The synthesis of a new bidentate (NN)–Mn(I) complex is reported and its catalytic activity towards the reduction of ketones and nitriles is studied. On comparing the reactivity of various other Mn(I) complexes supported by benzimidazole ligand, it was observed that the Mn(I) complexes bearing 6-methylpyridine and benzimidazole fragments exhibited the highest catalytic activity towards monohydrosilylation of ketones and dihydrosilylation of nitriles. Using this protocol, a wide range of ketones were selectively reduced to the corresponding silyl ethers. In case of unsaturated ketones, the chemoselective reduction of carbonyl group over olefinic bonds was observed. Additionally, selective dihydrosilylation of several nitriles were also achieved using this complex. Mechanistic investigations with radical scavengers suggested the involvement of radical species during the catalytic reaction. Stoichiometric reaction of the Mn(I) complex with phenylsilane revealed the formation of a new Mn(I) complex.