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64-04-0

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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.

Chemical Properties

Different sources of media describe the Chemical Properties of 64-04-0 differently. You can refer to the following data:
1. colourless or slightly yellow liquid with
2. Phenethylamine has a fish odor.

Occurrence

Reported found in the oil of bitter almonds. Also found in grapes, cabbage, kale, carrots, blue and provolone cheese, fatty fish, beer, sherry, grape wines, cocoa, cauliflower, beetroot, radish, rhubarb, sake and dried bonito.

Uses

Phenethylamine is used in manufacturing anti-depression agents and anti diabetic drugs. It is also used as the goodds for drug jiangtangling intermediate, also used for other organic synthesis.

Preparation

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

Definition

ChEBI: A phenylethylamine having the phenyl substituent at the 2-position.

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

General Description

Phenethylamine, a new stimulant designer drug, was analyzed by the liquid chromatography high-resolution mass spectrometry quadrupole-time-of-flight (LC-HRMS-QTOF) method.

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.

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

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

supporting information, 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.