7568-92-5

Basic information

• Product Name: DL-2-Phenylglycinol
• Synonyms: beta-amino-phenethylalcoho;BETA-AMINOPHENETHYL ALCOHOL;D/L-PHENYLGLYCINOL;DL-2-PHENYLGLYCINOL;2-AMINO-2-PHENYLETHANOL;DL-Alpha-Phenylglycinol;(s)-α-(Hydroxymethyl)benzenemethanamine;2-Phenyl-2-aminoethanol
• CAS NO: 7568-92-5
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• EINECS: 260-287-5
• Product Categories: Pharmaceutical Intermediates;Alcohols and Derivatives;Amines;Aromatics;Catalyst;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 7568-92-5.mol

Chemical Properties

• Melting Point: 53-58 °C
• Boiling Point: 261 °C
• Flash Point: 125.3 °C
• Appearance: White to light yellow/Solid
• Density: 1.0630 (rough estimate)
• Refractive Index: 1.5484
• Storage Temp.: Refrigerator
• Solubility: Soluble in chloroform, methanol.
• PKA: 12.51±0.10(Predicted)
• CAS DataBase Reference: DL-2-Phenylglycinol(CAS DataBase Reference)
• NIST Chemistry Reference: DL-2-Phenylglycinol(7568-92-5)
• EPA Substance Registry System: DL-2-Phenylglycinol(7568-92-5)

Safety Data

• Hazard Codes: C,Xi,Xn
• Statements: 34-41-37/38-22
• Safety Statements: 45-36/37/39-26-39
• RIDADR: 3263
• RTECS: SG7600000
• Hazardous Substances Data: 7568-92-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
DL-2-Phenylglycinol is used as an organocatalyst for the synthesis of chiral diamines. It plays a crucial role in the development of novel fluorescent chemosensors for amino acids, enhancing their chiral recognition properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, DL-2-Phenylglycinol is used as a chiral auxiliary in the efficient and practical synthesis of L-α-amino acids. This application contributes to the development of new drugs and therapeutic agents.
Used in Analytical Chemistry:
DL-2-Phenylglycinol is employed in the field of analytical chemistry for the determination of chiral recognition properties of novel fluorescent chemosensors for amino acids. This helps in the identification and quantification of specific amino acids, which are essential for various biological processes.
Overall, DL-2-Phenylglycinol is a versatile compound with applications in chemical synthesis, pharmaceuticals, and analytical chemistry, making it a valuable asset in the development of new technologies and products.

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 2529, 1996 DOI: 10.1016/0040-4039(96)00334-6

Upstream product

• 24461-61-8 (R)-Phenylglycine methyl ester 
• 22426-86-4 N-(benzyloxy)-2-phenylacetamide 
• 86217-38-1 4-phenyl-2-oxazolidinone 
• 100-42-5 styrene 
• 2835-06-5 phenylglycin 
• 6097-58-1 ethyl 2-phenyl-2-aminoacetate 
• 26385-08-0 N-(2-chloro-1-phenylethyl)acetamide 
• 25070-24-0 α-hydroxyacetophenone oxime 
• 96-09-3 styrene oxide 
• 875-74-1 (R)-phenylglycine 
• 124718-93-0 2-azido-2-phenylethanol 
• 64-17-5 ethanol 
• 7664-41-7 ammonia 
• 122889-15-0 Phenyl-[(Z)-trimethylsilanyl-imino]-acetic acid methyl ester 

Downstream Products

• 91904-51-7 2-(4-methylpiperazine-1-yl)-2-phenylethanol 
• 370571-64-5 N-phenylacetyl-(R)-phenylglycinol 
• 86217-38-1 4-phenyl-2-oxazolidinone 
• 56613-80-0 D-2-phenylglycinol 
• 20989-17-7 (2S)-2-phenylglycinol 
• 627860-42-8 C₁₁H₁₄Cl₂N₂O 
• 1266389-55-2 5-(3-benzyl-4-phenyloxazolidin-2-yl)-2-methoxyphenol 
• 1266389-51-8 3-benzyl-2-(2-bromoethyl)-4-phenyloxazolidine 
• 1266389-60-9 3-benzyl-2-(4-chlorophenyl)-4-phenyloxazolidine 
• 1266389-52-9 3-benzyl-2-(3,4,5-trimethoxyphenyl)-4-phenyloxazolidine 
• 1266389-59-6 3-benzyl-2-(4-methoxyphenyl)-4-phenyloxazolidine 
• 1266389-61-0 3-benzyl-2-(3,4-dimethoxyphenyl)-4-phenyloxazolidine 
• 1266389-62-1 3-benzyl-4-phenyl-2-propyloxazolidine 
• 1266389-77-8 (Z)-3-benzyl-2-ethylidene-4-phenyloxazolidine 

Relevant articles and documents

Construction and activity evaluation of novel dual-target (SE/CYP51) anti-fungal agents containing amide naphthyl structure

With the increase of fungal infection and drug resistance, it is becoming an urgent task to discover the highly effective antifungal drugs. In the study, we selected the key ergosterol bio-synthetic enzymes (Squalene epoxidase, SE; 14 α-demethylase, CYP51) as dual-target receptors to guide the construction of novel antifungal compounds, which could achieve the purpose of improving drug efficacy and reducing drug-resistance. Three different series of amide naphthyl compounds were generated through the method of skeleton growth, and their corresponding target products were synthesized. Most of compounds displayed the obvious biological activity against different Candida spp. and Aspergillus fumigatus. Among of them, target compounds 14a-2 and 20b-2 not only possessed the excellent broad-spectrum anti-fungal activity (MIC50, 0.125–2 μg/mL), but also maintained the anti-drug-resistant fungal activity (MIC50, 1–4 μg/mL). Preliminary mechanism study revealed the compounds (14a-2, 20b-2) could block the bio-synthetic pathway of ergosterol by inhibiting the dual-target (SE/CYP51) activity, and this finally caused the cleavage and death of fungal cells. In addition, we also discovered that compounds 14a-2 and 20b-2 with low toxic and side effects could exert the excellent therapeutic effect in mice model of fungal infection, which was worthy for further in-depth study.

Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3)-H Amidation

Reported herein is the design of a photosensitization strategy to generate triplet nitrenes and its applicability for the intramolecular C-H amidation reactions. Substrate optimization by tuning physical organic parameters according to the proposed energy transfer pathway led us to identify hydroxamates as a convenient nitrene precursor. While more classical nitrene sources, representatively organic azides, were ineffective under the current photosensitization conditions, hydroxamates, which are readily available from alcohols or carboxylic acids, are highly efficient in accessing synthetically valuable 2-oxazolidinones and γ-lactams by visible light. Mechanism studies supported our working hypothesis that the energy transfer path is mainly operative.

Aryl olefin azole derivative as well as preparation method and application thereof

The invention belongs to the technical field of medicines, and relates to an aryl olefin azole derivative shown in a general formula I, stereoisomers thereof and pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, and substituent groups Ar, R and X have definitions given in the specification. The invention also relates to a method for preparing the compound as shown in the general formula I, a medicinal composition containing the compound and application of the compound and the medicinal composition in preparation of medicines for treating and preventing superficial fungal and deep fungal diseases.

Site-Specific C(sp3)–H Aminations of Imidates and Amidines Enabled by Covalently Tethered Distonic Radical Anions

The utilization of N-centered radicals to synthesize nitrogen-containing compounds has attracted considerable attention recently, due to their powerful reactivities and the concomitant construction of C?N bonds. However, the generation and control of N-centered radicals remain particularly challenging. We report a tethering strategy using SOMO-HOMO-converted distonic radical anions for the site-specific aminations of imidates and amidines with aid of the non-covalent interaction. This reaction features a remarkably broad substrate scope and also enables the late-stage functionalization of bioactive molecules. Furthermore, the reaction mechanism is thoroughly investigated through kinetic studies, Raman spectroscopy, electron paramagnetic resonance spectroscopy, and density functional theory calculations, revealing that the aminations likely involve direct homolytic cleavage of N?H bonds and subsequently controllable 1,5 or 1,6 hydrogen atom transfer.

Method for preparing amino alcohol compound by using halogenated intermediate

The invention discloses a method for preparing an amino alcohol compound by utilizing a halogenated intermediate. According to the method, an oxygen-halogen bond can be prepared by utilizing cyclic diacyl peroxide and halogenated salt under an illumination condition, and the oxygen-halogen bond is prone to homolysis under an illumination condition to form an active free radical, so the amino alcohol is finally prepared. The novel method for synthesizing the amino alcohol is high in atom utilization rate, simple in synthesis method and high in yield, so the consumption of halide for reactions with synthesis values is reduced, and the purposes of environmental protection and green chemistry are better achieved.

Electrochemical Difunctionalization of Alkenes by a Four-Component Reaction Cascade Mumm Rearrangement: Rapid Access to Functionalized Imides

An electrochemical four-component reaction cascade Mumm rearrangement was developed. It is a rare example of in situ generation of O-acyl isoamides for 1,3-(O→N) acyl transfer. Inexpensive, commercially available arylethylenes, aryl or heterocyclic acids, acetonitrile, and alcohols were used as substrates. A wide range of aryl acids and alcohols were tolerated and provided imides in satisfactory yields. Subsequent hydrolysis of imides could be utilized to synthesize valuable amides and β-amino alcohol derivatives.

Borohydride reduction stabilizing system and method for reducing ester into alcohol

The invention provides a borohydride reduction stabilizing system and a method for reducing ester into alcohol. The borohydride reduction stabilizing system comprises a borohydride reducing agent anda stabilizer for stabilizing the borohydride reducing agent, wherein the borohydride reducing agent is sodium borohydride or potassium borohydride, and the stabilizer is an alkali metal salt of alcohol. On the basis of an existing sodium borohydride/potassium reducing agent, an alcohol alkali metal salt (such as sodium alcoholate or potassium alcoholate) is added, and then the sodium borohydride/potassium reducing agent can keep stable and is not decomposed under a heating condition, so that on one hand, reduction activity is maintained in a relatively high state and the situation of excessiveuse is reduced, and on the other hand, generation of hydrogen is reduced and the process risk is reduced.

Rapid and Quantitative Profiling of Substrate Specificity of ω-Transaminases for Ketones

ω-Transaminases (ω-TAs) have gained growing attention owing to their capability for asymmetric synthesis of chiral amines from ketones. Reliable high-throughput activity assay of ω-TAs is essential in carrying out extensive substrate profiling and establishing a robust screening platform. Here we report spectrophotometric and colorimetric methods enabling rapid quantitation of ω-TA activities toward ketones in a 96-well microplate format. The assay methods employ benzylamine, a reactive amino donor for ω-TAs, as a cosubstrate and exploit aldehyde dehydrogenase (ALDH) as a reporter enzyme, leading to formation of benzaldehyde detectable by ALDH owing to concomitant NADH generation. Spectrophotometric substrate profiling of two wild-type ω-TAs of opposite stereoselectivity was carried out at 340 nm with 22 ketones, revealing subtle differences in substrate specificities that were consistent with docking simulation results obtained with cognate amines. Colorimetric readout for naked eye detection of the ω-TA activity was also demonstrated by supplementing the assay mixture with color-developing reagents whose color reaction could be quantified at 580 nm. The colorimetric assay was applied to substrate profiling of an engineered ω-TA for 24 ketones, leading to rapid identification of reactive ketones. The ALDH-based assay is expected to be promising for high-throughput screening of enzyme collections and mutant libraries to fish out the best ω-TA candidate as well as to tailor enzyme properties for efficient amination of a target ketone.

Montmorillonite K10 catalyzed highly regioselective azidolysis of epoxides: A short and efficient synthesis of phenylglycine

A series of β‐hydroxyazides were effectively synthesized from the regioselective ring opening of epoxides by sodium azide using montmorillonite K10 as a novel heterogeneous catalyst in aqueous acetonitrile in good to excellent yields. The utility of this method has been demonstrated by achieving a short synthesis of phenylglycine in 33.5% overall yield.

Directed β C-H Amination of Alcohols via Radical Relay Chaperones

A radical-mediated strategy for β C-H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom abstraction. A streamlined protocol enables rapid conversion of alcohols to their β-amino analogs (via in situ conversion of alcohols to imidates, directed C-H amination, and hydrolysis to NH2). Mechanistic experiments indicate HAT is rate-limiting, whereas intramolecular amination is product- and stereo-determining.