Name: 2-(Benzyloxy)ethanol
Brand: BOC Sciences
Rating: 5 (1 reviews)

Size

Price

Stock

Quantity

$--

In stock

Purity

≥95%

Solubility

Soluble in Chloroform (Slightly), Methanol (Slightly)

Appearance

Colorless to Light Yellow Liquid

Storage

Store at 2-8°C under inert atmosphere

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

2-phenylmethoxyethanol

Synonyms

2-Benzyloxyethyl alcohol; Benzyl 2-hydroxyethyl ether; Benzyl-PEG2-alcohol; Benzyloxyethanol; BzG; Ethylene glycol benzyl ether; Ethylene glycol monobenzyl ether; Glycol monobenzyl ether; NSC 8886; Ethanol, 2-(phenylmethoxy)-; 2-Benzyloxy-1-ethanol; 2-(benzyloxy)ethan-1-ol; Benzyl cellosolve

Boiling Point

254.4±15.0°C at 760 mmHg

Melting Point

<-75°C

Density

1.071 g/mL at 25°C

InChI Key

CUZKCNWZBXLAJX-UHFFFAOYSA-N

InChI

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

SMILES

C1=CC=C(C=C1)COCCO

1. An Intramolecular Hydroaminomethylation-Based Approach to Pyrrolizidine Alkaloids under Microwave-Assisted Heating

Elena Petricci, Simone Zurzolo, Camilla Matassini, Samuele Maramai, Francesca Cardona, Andrea Goti, Maurizio Taddei Molecules. 2022 Jul 25;27(15):4762. doi: 10.3390/molecules27154762.

A general method for the synthesis of pyrrolizidine derivatives using an intramolecular hydroaminomethylation protocol (HAM) under microwave (MW) dielectric heating is reported. Starting from a 3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-vinylpyrrolidine, MW-assisted intramolecular HAM in the presence of gaseous H2 and CO gave the natural alkaloid hyacinthacine A2 protected as benzyl ether. The same approach gave a lentiginosine analogue starting from the corresponding vinyl N-hydroxypyrrolidine. The nature of the reaction products and the yields were strongly influenced by the relative stereochemistry of the starting pyrrolidines, as well as by the catalyst/ligand employed. The use of ethanol as a solvent provides environmentally friendly conditions, while the ligand/catalyst system can be recovered by separating the alkaloid product with an SCX column and recycling the ethanolic solution. HAM worked up to three times with the recycled catalyst solution without any significant impact on yield.

2-(Benzyloxy)ethanol, provides a flexible ether-containing handle that can be used to connect and spatially tune small-molecule ligands in targeted protein degradation constructs. Its ether linkage and terminal alcohol functionality support robust synthetic modification strategies commonly employed in PROTAC assembly. The resulting linker architecture can help optimize linker length and conformational freedom to improve productive ternary complex formation, and the detailed structure and reactivity considerations are provided below.

Structure: The molecule contains a benzyloxy ether and a terminal primary alcohol, connected through an ethylene spacer. It features an aromatic benzyl group, ether oxygen atoms, and an alcohol capable of hydrogen bonding. Overall, it is a small, polar, oxygen-rich linker with ether and hydroxyl functional groups suitable for derivatization.

Reactivity: The terminal alcohol enables standard PROTAC linker functionalization via esterification or ether formation, typically using activated carboxylic acids or electrophiles under mild base conditions. For benzyl-protected alcohol strategies, hydrogenolysis or other deprotection methods can regenerate the free hydroxyl when needed. Common coupling approaches rely on nucleophilic substitution or acylation principles, with appropriate catalysts and dry, inert solvents to minimize side reactions.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂