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
• Article Data: 39

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

Description

DL-2-Phenylglycinol is a chiral arylalkylamine, which is a white to light yellow powder. It is known for its organocatalytic properties and is utilized in various chemical reactions and processes.

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

• 96-09-3 styrene oxide 
• 25070-24-0 α-hydroxyacetophenone oxime 
• 64-17-5 ethanol 
• 7664-41-7 ammonia 
• 875-74-1 (R)-phenylglycine 
• 131934-09-3 ethyl 2-(hydroxyimino)-2-phenylacetate 
• 135277-63-3 1-acetoxy-2-azido-2-phenyl ethane 
• 100-42-5 styrene 
• 7732-18-5 water 
• 6097-58-1 ethyl 2-phenyl-2-aminoacetate 
• 24461-61-8 (R)-Phenylglycine methyl ester 
• 122889-15-0 Phenyl-[(Z)-trimethylsilanyl-imino]-acetic acid methyl ester 
• 124718-93-0 2-azido-2-phenylethanol 
• 22426-86-4 N-(benzyloxy)-2-phenylacetamide 

Downstream Products

• 91904-51-7 2-(4-methylpiperazine-1-yl)-2-phenylethanol 
• 97678-52-9 (2-hydroxy-1-phenylethyl)urea 
• 56613-80-0 D-2-phenylglycinol 
• 93732-64-0 phenyl-(4-phenyl-4,5-dihydro-oxazol-2-yl)-amine 
• 1437-78-1 2-ammonio-2-phenylethyl sulfate 
• 199868-83-2 3-Phenyl-2,3-dihydro-9bH-oxazolo[2,3-a]isoindol-5-one 
• 214267-24-0 1-((S)-3-Phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-yl)-1H-benzotriazole 

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.

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.

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.