5197-66-0

Basic information

• Product Name: 2-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]ethanol
• Synonyms: 2-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]ethanol;2-(2-Chloroethoxy)ethyl[2-(2-hydroxyethoxy)ethyl] ether;Tetraethylene glycol chlorohydrin;Ethanol, 2-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]-;TETRAETHYLENE GLYCOL MONOCHLOROHYDRINE
• CAS NO: 5197-66-0
• Molecular Formula: C₈H₁₇ClO₄
• Molecular Weight: 212.67
• Product Categories: Miscellaneous Reagents, Polyethyleneglycol Derivatives
• Mol File: 5197-66-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 305.34°C (rough estimate)
• Flash Point: 138.5°C
• Appearance: /
• Density: 1.2059 (rough estimate)
• Vapor Pressure: 7.73E-05mmHg at 25°C
• Refractive Index: 1.4571 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.36±0.10(Predicted)
• CAS DataBase Reference: 2-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]ethanol(5197-66-0)
• EPA Substance Registry System: 2-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]ethanol(5197-66-0)

Safety Data

• Hazardous Substances Data: 5197-66-0(Hazardous Substances Data)

Usage

Uses

2-[2-[2-(2-Chloroethoxy)ethoxy]ethoxy]ethanol is a polyethylene glycol used in the synthesis of novel glycolipids that bind HIV-1 cell surface glycoprotein Gp120 with potential application to pharmaceutical HIV-1 drugs. Also used in the synthesis of PET imaging agents targeting brain β-amyloid.

InChI:InChI=1/C8H17ClO4/c9-1-3-11-5-7-13-8-6-12-4-2-10/h10H,1-8H2

Upstream product

• 112-60-7 Tetraethylene glycol 
• 123-91-1 1,4-dioxane 
• 107-21-1 ethylene glycol 
• 107-07-3 2-chloro-ethanol 
• 111-44-4 3-oxa-1,5-dichloropentane 

Downstream Products

• 396106-50-6 2-(2-(2-(2-chloroethoxy)ethoxy)ethoxy)acetic acid 
• 1219042-09-7 2-[2-(2-(2-(4-iodophenoxy)ethoxy)ethoxy)ethoxy]ethanol 
• 197513-82-9 4-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]-benzaldehyde 
• 106263-73-4 N-phenyl-3-oxo-1-aza-15-crown-5 
• 66943-05-3 1,4,7,10-tetraoxa-15-azacyclopentadecane 
• 96574-05-9 14-(4-Methoxyphenoxy)-3,6,9,12-tetraoxa-1-tetradecanol 
• 118098-96-7 ditosylate of 13-(benzyloxymethyl)-3,6,9,12,15,18,24-octaoxa-1,26-hexacosanediol 
• 118069-28-6 bis-tetrahydropyranyl ether of 13-(benzyloxymethyl)-3,6,9,12,15,18,21,24-octaoxa-1,26-hexacosanediol 
• 118069-29-7 13-(benzyloxymethyl)-3,6,9,12,15,18,21,24-octaoxa-1,26-hexacosanediol 
• 91472-19-4 (benzyloxymethyl)-27-crown-9 
• 144334-78-1 1,11-bis<4-<2-(2-(2-(2-(toluene-p-sulfonyl)ethoxy)ethoxy)ethoxy)ethoxy>phenoxy>-3,6,9-trioxaundecane 
• 844638-10-4 2-{2-{2-{2-{{7-{2-{2-{2-{2-{[(4-methylphenyl)sulfonyl]oxy}ethoxy}ethoxy}ethoxy}ethoxy}-9-oxo-9H-fluoren-2-yl}oxy}ethoxy}ethoxy}ethoxy}ethyl 4-methylbenzenesulfonate 
• 374808-09-0 11-(4-Methoxybenzylthio)-3,6,9-trioxaundecanyl tosylate 
• 86770-67-4 2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethanol 

Relevant articles and documents

Difunctional derivatives of bis(m-phenylene)- 32-crown-10

Optimization studies of the condensation of methyl 3,5-dihydroxybenzoate (1) with tetra(ethylene glycol) dichloride (3) resulted in improvement of the yield of the 1 + 1 cyclization product, 5-carbomethoxy-m-phenylene-16-crown-5 (5), to 67% (HPLC), but no improvement in the yield (28%, HPLC) of the desired 2+2 product, bis(5-carbomethoxy-m-phenylene)-32-crown-10 (4). However, after optimization, a two-step procedure provided improved yields of 4 and this procedure was generalized to afford other difunctional monomers. Condensation of substituted resorcinols with 3 and subsequent transformations yielded substituted (R) 3,5-bis(11-chloro-3,6,9-trioxaundecyl-oxy)benzenes (7, 9-14). Reaction of dihalides 7 (R = COOCH3), 13 (R = CHO), and 12 (R = CH2OSi(Me)2-t-Bu) with methyl 3,5-dihydroxybenzoate (1) produced bis(5-carbomethoxy-m-phenylene)-32-crown-10 (4) (43%), 5-carbomethoxy-m-phenylene-5′-formyl-m′-phenylene-32-crown-10 (15) (32%), and the lactone (16a) (18%, derived from the initially formed 5-hydroxymethyl-m-phenylene-5′-carbomethoxy-m′-phenylene-32-crown-10 (16)), respectively. Subsequent reactions gave the corresponding diacid (17), bis(hydroxymethyl) (19), bis(bromomethyl) (20), diacetyl (18), diformyl (21), bis(p-nitrophenoxymethyl) (22), and di(acetoxymethyl) (23) derivatives.