622-08-2

Basic information

• Product Name: 2-Benzyloxyethanol
• Synonyms: RARECHEM AL BD 0628;2-(benzyloxy)-ethano;2-(phenylmethoxy)-ethano;Benzylcelosolv;Ethanol, 2-(benzyloxy)-;Glycol benzyl ether;Glycol monobenzyl ether;glycolmonobenzylether
• CAS NO: 622-08-2
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• EINECS: 210-719-3
• Product Categories: Ethylene Glycols & Monofunctional Ethylene Glycols;Monofunctional Ethylene Glycols;Alcohols;Building Blocks;C9 to C10;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 622-08-2.mol
• Article Data: 110

Chemical Properties

• Melting Point: <-75 °C
• Boiling Point: 265 °C(lit.)
• Flash Point: 110 °C
• Appearance: Clear colorless/Liquid
• Density: 1.071 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00895mmHg at 25°C
• Refractive Index: n20/D 1.521(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.40±0.10(Predicted)
• Water Solubility: 4.282g/L(23 oC)
• BRN: 2043566
• CAS DataBase Reference: 2-Benzyloxyethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzyloxyethanol(622-08-2)
• EPA Substance Registry System: 2-Benzyloxyethanol(622-08-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: KJ7550000
• Hazardous Substances Data: 622-08-2(Hazardous Substances Data)

Usage

Description

Benzyl-PEG2-alcohol is a PEG linker with an acid labile, benzyl protecting group and a reactive primary alcohol. The primary alcohol can react and further derivatize the compound. The hydrophilic PEG linker increases the water solubility of the compound in aqueous media.

Chemical Properties

Ethylene glycol monobenzyl ether is a Colorless to light yellow liquid which will dissolve a large number of organic substances among which are oils, fats, greases, some vinyl resins, dewaxed damar, rosin, ester gum, etc. It is used principally as a high boiling solvent in lacquers, inks, and textile dyeing.

Uses

Different sources of media describe the Uses of 622-08-2 differently. You can refer to the following data:
1. 2-Benzyloxyethanol is used in a base-free iridium-catalyzed direct alkylation of active methylene compounds with alcohols.
2. 2-(Benzyloxy)ethanol has been used in:9-(2-hydroxyethyl)-linked synthesis of 2,6-diaminopurinessynthesis of benzyloxy ethyl methacrylate monomer by esterification with methacryloyl chloridea base-free iridium-catalyzed direct alkylation of active methylene compounds with alcohols

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 389, 1990 DOI: 10.1016/S0040-4039(00)94562-3

Hazard

Toxic by ingestion.

InChI:InChI=1/C9H12O2/c10-6-7-11-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2

Upstream product

• 75-21-8 oxirane 
• 100-51-6 benzyl alcohol 
• 936-51-6 2-phenyl-1,3-dioxolane 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 100-44-7 benzyl chloride 
• 107-21-1 ethylene glycol 
• 97-93-8 triethylaluminum 
• 30379-55-6 benzyloxyacetic acid 
• 7446-70-0 aluminium trichloride 
• 60-29-7 diethyl ether 
• 766-77-8 Dimethylphenylsilane 
• 60656-87-3 benzyloxyacetoaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 100791-51-3 (2R,3R,4R)-1-Benzyloxy-4-methyl-5-hexene-2,3-diol 

Downstream Products

• 13808-07-6 lactic acid-(2-benzyloxy-ethyl ester) 
• 17229-17-3 benzyl 2-chloroethyl ether 
• 121974-92-3 phosphorous acid tris-(2-benzyloxy-ethyl ester) 
• 88964-98-1 2-(cyclohexylmethoxy)ethanol 
• 58841-52-4 2-(benzyloxy)ethyl methanesulfonate 
• 5312-10-7 2-(benzyloxy)ethyl acetate 
• 93086-11-4 3-(2-benzyloxy-ethoxy)-propionitrile 
• 93900-46-0 1-Pentyloxymethoxy-2-benzyloxy-aethan 
• 53256-85-2 1-(1,1,1-Trichlor-2-hydroxyethoxy)-2-benzyloxy-ethan 
• 123455-81-2 Pyridine-2-sulfonic acid 2-benzyloxy-ethyl ester 
• 98627-26-0 2-(2-Benzyloxy-ethoxy)-tetradecanoic acid ethyl ester 
• 124251-97-4 (S)-2-(2-Benzyloxy-ethoxy)-propionic acid 
• 97431-31-7 2-(benzyloxy)ethyl 2-bromohexadecanoate 
• 22128-37-6 butyric acid-(2-benzyloxy-ethyl ester) 

Relevant articles and documents

3-(5-METHOXY-1-OXOISOINDOLIN-2-YL)PIPERIDINE-2,6-DIONE DERIVATIVES AND USES THEREOF

The present disclosure relates to compounds of formula (I') and pharmaceutical compositions and their use in reducing Widely Interspaced Zinc Finger Motifs (WIZ) expression levels, or inducing fetal hemoglobin (HbF) expression, and in the treatment of inherited blood disorders (e.g., hemoglobinopathies, e.g., beta-hemoglobinopathies), such as sickle cell disease and beta-thalassemia.

Nematicidal activity of benzyloxyalkanols against pine wood nematode

Pine wilt disease (PWD) is caused by the pine wood nematode (PWN; Bursaphelenchus xylophilus) and causes severe environmental damage to global pine forest ecosystems. The current strategies used to control PWN are mainly chemical treatments. However, the continuous use of these reagents could result in the development of pesticide-resistant nematodes. Therefore, the present study was undertaken to find potential alternatives to the currently used PWN control agents abamectin and emamectin. Benzyloxyalkanols (BzOROH; R = C2–C9 ) were synthesized and the nematicidal activity of the synthetic compounds was investigated. Enzymatic inhibitory assays (acetylcholinesterase (AChE) and glutathione S-transferase (GST)) were performed with BzOC8OH and BzOC9OH to understand their mode of action. The benzyloxyalkanols showed higher nematicidal activity than did benzyl alcohol. Among the tested BzOROHs, BzC8OH and BzC9OH showed the strongest nematicidal activity. The LD50 values of BzC8OH and BzC9OH were 246.1 and 158.0 ppm, respectively. No enzyme inhibitory activity was observed for BzC8OH and BzC9OH. The results suggested that benzyloxyalcohols could be an alternative nematicidal agent.

Design, Synthesis, and Evaluation of VHL-Based EZH2 Degraders to Enhance Therapeutic Activity against Lymphoma

Traditional EZH2 inhibitors are developed to suppress the enzymatic methylation activity, and they may have therapeutic limitations due to the nonenzymatic functions of EZH2 in cancer development. Here, we report proteolysis-target chimera (PROTAC)-based EZH2 degraders to target the whole EZH2 in lymphoma. Two series of EZH2 degraders were designed and synthesized to hijack E3 ligase systems containing either von Hippel-Lindau (VHL) or cereblon (CRBN), and some VHL-based compounds were able to mediate EZH2 degradation. Two best degraders, YM181 and YM281, induced robust cell viability inhibition in diffuse large B-cell lymphoma (DLBCL) and other subtypes of lymphomas, outperforming a clinically used EZH2 inhibitor EPZ6438 (tazemetostat) that was only effective against DLBCL. The EZH2 degraders displayed promising antitumor activities in lymphoma xenografts and patient-derived primary lymphoma cells. Our study demonstrates that EZH2 degraders have better therapeutic activity than EZH2 inhibitors, which may provide a potential anticancer strategy to treat lymphoma.