6048-68-6

Basic information

• Product Name: NONAETHYLENE GLYCOL MONOMETHYL ETHER
• Synonyms: NONAETHYLENE GLYCOL MONOMETHYL ETHER;MPEG9-OH;MPEG-9;2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol;m-PEG9-alcohol;Methyl-PEG9-alcohol
• CAS NO: 6048-68-6
• Molecular Formula: C₁₉H₄₀O₁₀
• Molecular Weight: 428.51
• Product Categories: Ethylene Glycols & Monofunctional Ethylene Glycols;Monofunctional Ethylene Glycols
• Mol File: 6048-68-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 14 °C
• Boiling Point: 490.1 °C at 760 mmHg
• Flash Point: 250.2 °C
• Appearance: /
• Density: 1.10
• Vapor Pressure: 1.17E-11mmHg at 25°C
• Refractive Index: 1.4570 to 1.4620
• PKA: 14.36±0.10(Predicted)
• CAS DataBase Reference: NONAETHYLENE GLYCOL MONOMETHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: NONAETHYLENE GLYCOL MONOMETHYL ETHER(6048-68-6)
• EPA Substance Registry System: NONAETHYLENE GLYCOL MONOMETHYL ETHER(6048-68-6)

Safety Data

• Hazardous Substances Data: 6048-68-6(Hazardous Substances Data)

Usage

Description

m-PEG9-alcohol is a PEG linker containing a hydroxyl group. The hydroxyl group enables further derivatization or replacement with other reactive functional groups. The hydrophilic PEG spacer increases solubility in aqueous media.

InChI:InChI=1/C19H40O10/c1-21-4-5-23-8-9-25-12-13-27-16-17-29-19-18-28-15-14-26-11-10-24-7-6-22-3-2-20/h20H,2-19H2,1H3

Synthetic route

1-Phenyl-2,5,8,11,14,17,20,23,26,29-decaoxatriacontane (211859-58-4) → 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran for 1.08333h;	97%
With hydrogen; palladium 10% on activated carbon In methanol under 2.58551 Torr;	74%

pentaethylene glycol (2615-15-8) + 2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate (62921-74-8) → 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 18h; Inert atmosphere; Reflux;	65%

pentaethylene glycol (2615-15-8) + 3,6,9-trioxadecyl bromide (72593-77-2) → 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6)

Conditions	Yield
Stage #1: pentaethylene glycol With sodium hydride In toluene at 20℃; for 2h; Stage #2: 3,6,9-trioxadecyl bromide In toluene at 20℃; for 1h;	51%

3,6,9,12,15,18,21-heptaoxadocosan-1-ol (4437-01-8) → 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6)

Conditions	Yield
With benzenesulfonyl chloride; benzene Erwaermen des Reaktionsprodukts mit Natrium-diaethylenglykolat in Diaethylenglykol;

hexaethylene glycol monomethyl ether (23601-40-3) → 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6)

Conditions	Yield
With sodium hydroxide; benzenesulfonyl chloride; benzene Erwaermen des Reaktionsprodukts mit Natrium-triaethylenglykolat in Triaethylenglykol;

3,6,9,12,15-pentaoxahexadecanol (23778-52-1) → 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene; benzenesulfonyl chloride; sodium hydroxide / Erwaermen des Reaktionsprodukts mit Natrium-diaethylenglykolat in Diaethylenglykol 2: benzene; benzenesulfonyl chloride / Erwaermen des Reaktionsprodukts mit Natrium-diaethylenglykolat in Diaethylenglykol View Scheme

triethylene glucol monomethyl ether (112-35-6) → 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; benzenesulfonyl chloride; benzene / Erwaermen des Reaktionsprodukts mit Natrium-triaethylenglykolat in Triaethylenglykol 2: sodium hydroxide; benzenesulfonyl chloride; benzene / Erwaermen des Reaktionsprodukts mit Natrium-triaethylenglykolat in Triaethylenglykol View Scheme

2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) + propargyl bromide (106-96-7) → 2,5,8,11,14,17,20,23,26,29-decaoxadotriacont-31-yne (1233324-30-5)

Conditions	Yield
Stage #1: 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol With sodium hydride In tetrahydrofuran; mineral oil Stage #2: propargyl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; for 4h;	99%
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 168h; Inert atmosphere;	34%

2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) + (E)-p-formylcinnamic acid (66885-68-5) → 4-Formylcinnamic acid nonaethylene glycol methyl ether ester

Conditions	Yield
With toluene-4-sulfonic acid In xylene for 4h; Heating / reflux;	97%

2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → 2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-oic acid (102013-72-9)

Conditions	Yield
With Jones reagent In acetone at 20℃; for 2h;	90%

2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) + enoxolone (471-53-4) → C49H84O13

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 14h; Reagent/catalyst; Solvent; Temperature;	80%

2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) + p-toluenesulfonyl chloride (98-59-9) → nonaethylene glycol methyl tosyl ether (211859-75-5)

Conditions	Yield
With sodium hydroxide; PEG 550 In tetrahydrofuran; water	78%

(14)CC30H36N6O3 + 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → (14)CC46H72N4O13

Conditions	Yield
With potassium carbonate In acetonitrile Heating;	71%

C17H12O3 (696661-26-4) + 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → 2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 3-(4-methylphenyl)-1-oxo-1H-indene-2-carboxylate (1016567-41-1)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In dichloromethane at 20℃;	68%

(E)-1,3-Bis(cyclohexylmethyl)-8-(4-(2-(1H-imidazol-1-ylcarbonyl)vinyl)phenyl)-9H-purin-2,6(1H,3H)-dione (211859-64-2) + 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → (E)-4-(1,3-Bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2.6-dioxo-9H-purin-8-yl)cinnamic Acid Nonaethylene Glycol Monomethyl Ether Ester (211859-42-6)

Conditions	Yield
With potassium carbonate In acetonitrile for 18h; Heating / reflux;	65%

bromoacetic acid tert-butyl ester (5292-43-3) + 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → tert-butyl 2,5,8,11,14,17,20,23,26,29-decaoxahentriacontan-31-oate

Conditions	Yield
Stage #1: 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Stage #2: bromoacetic acid tert-butyl ester In tetrahydrofuran; mineral oil at 20℃; for 1h;	59%
Stage #1: 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: bromoacetic acid tert-butyl ester In tetrahydrofuran at 20℃; for 1h;	59%
Stage #1: 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: bromoacetic acid tert-butyl ester In tetrahydrofuran at 20℃; for 1h;	59%
Stage #1: 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: bromoacetic acid tert-butyl ester In tetrahydrofuran at 20℃; for 1h;	59%

2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) + 4-bromomethyl pyridine hydrobromide (73870-24-3) → C25H45NO10

Conditions	Yield
Stage #1: 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol With sodium hydride In tetrahydrofuran; mineral oil at 25℃; for 0.5h; Inert atmosphere; Stage #2: 4-bromomethyl pyridine hydrobromide With sodium hydride In tetrahydrofuran; mineral oil at 25℃; for 14.5h; Inert atmosphere;	53%

2-(1,3-Bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl)benzoic acid (211859-79-9) + 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → 2-[1,3-Bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl]benzoic acid Nonaethylene Glycol Methyl Ether Ester

Conditions	Yield
With potassium carbonate In acetonitrile Heating / reflux;	43%

2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → 28-bromo-2,5,8,11,14,17,20,23,26-nonaoxaoctacosane (125562-30-3)

Conditions	Yield
With phosphorus tribromide In diethyl ether at 0℃;	22%
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere 2: tetrabutylammomium bromide / acetonitrile / 16 h / 50 °C / Inert atmosphere View Scheme

(E)-4-(1,3-Bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-6-oxo-2-thioxo-9H-purin-8-yl)cinnamic Acid (177352-23-7) + 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → (E)-4-(1,3-Bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-6-oxo-2-thioxo-9H-purin-8-yl)cinnamic Acid Nonaethylene Glycol Methyl Ether Ester

Conditions	Yield
With potassium carbonate In acetonitrile Heating / reflux;	20%

3-butyl-1-chloro-isoquinoline (87-06-9) + 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → 3-butyl-1-(26-methoxy-3,6,9,12,15,18,21,24-octaoxa-hexacosyloxy)-isoquinoline (104509-87-7)

Conditions	Yield
With sodium at 100 - 110℃;

4-butyl-1-chloro-isoquinoline (55150-50-0) + 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → 4-butyl-1-(26-methoxy-3,6,9,12,15,18,21,24-octaoxa-hexacosyloxy)-isoquinoline (104508-91-0)

Conditions	Yield
With sodium at 100 - 110℃;

1-chloro-3-hexylisoquinoline (858194-04-4) + 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → 3-hexyl-1-(26-methoxy-3,6,9,12,15,18,21,24-octaoxa-hexacosyloxy)-isoquinoline (104399-40-8)

Conditions	Yield
With sodium at 110℃;

2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → 1-methoxy-26-methylamino-3,6,9,12,15,18,21,24-octaoxa-hexacosane

Conditions	Yield
With sodium hydroxide; benzenesulfonyl chloride; benzene Beim Erwaermen des Reaktionsprodukts mit Methylamin in Aethanol;
Multi-step reaction with 2 steps 1: 78 percent / NaOH; PEG 550 / H2O; tetrahydrofuran 2: 96 percent / ethanol View Scheme

(13)C6C22H34N4O4 (1037620-58-8) + 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → (13)C6C41H72N4O13

2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) + toluene-4-sulfonic acid (104-15-4) → nonaethylene glycol methyl tosyl ether (211859-75-5)

Conditions	Yield
In pyridine at 20℃;

(E)-1,3-bis(cyclohexylmethyl)-8-(3-(2-(1H-imidazol-1-ylcarbonyl)vinyl)phenyl)-9H-purin-2,6(1H,3H)-dione + 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → (E)-3-[1,3-Bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl]cinnamic Acid Nonaethylene Glycol Methyl Ether Ester

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In DMF (N,N-dimethyl-formamide) at 55℃; for 20h;

C31H34N6O3 + 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-ol (6048-68-6) → 3-{4-[1,3-Bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl]phenyl}propiolic Acid Nonaethylene Glycol Methyl Ether Ester

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In DMF (N,N-dimethyl-formamide) at 20 - 40℃; for 2h;

Upstream product

• 23601-40-3 hexaethylene glycol monomethyl ether 
• 211859-58-4 1-Phenyl-2,5,8,11,14,17,20,23,26,29-decaoxatriacontane 
• 2615-15-8 pentaethylene glycol 
• 72593-77-2 3,6,9-trioxadecyl bromide 
• 62921-74-8 2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate 
• 112-35-6 triethylene glucol monomethyl ether 
• 23778-52-1 3,6,9,12,15-pentaoxahexadecanol 
• 4437-01-8 3,6,9,12,15,18,21-heptaoxadocosan-1-ol 

Downstream Products

• 211859-42-6 (E)-4-(1,3-Bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2.6-dioxo-9H-purin-8-yl)cinnamic Acid Nonaethylene Glycol Monomethyl Ether Ester 
• 102013-72-9 2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-oic acid 
• 405518-55-0 2,5,8,11,14,17,20,23,26,29-decaoxahentriacontan-31-oic acid 
• 1233320-01-8 ethyl 1-hydroxy-1-methyl-6-(2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yloxy)-3-phenyl-1H-indene-2-carboxylate 
• 1233319-98-6 ethyl 6-(2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yloxy)-1-oxo-3-phenyl-1H-indene-2-carboxylate 
• 125562-30-3 28-bromo-2,5,8,11,14,17,20,23,26-nonaoxaoctacosane 

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