1606-85-5

Basic information

• Product Name: 1,4-Bis(2-hydroxyethoxy)-2-butyne
• Synonyms: Ethanol, 2,2-2-butyne-1,4-diylbis(oxy)bis-;2-BUTYNE-1,4-DIOLBIS(2-HYDROXYETHYL)ETHER(CA.50%ISOMER);1,4-BIS(2-HYDROXYETHOXY)-2-BUTYNE 98%;2-[4-(2-Hydroxyethoxy)but-2-ynoxy]ethanol;1,4-Di(2-hydroxyethoxy)butyne-2;2-Butyne-1,4-diol Bis(2-hydroxyethyl) Ether 1,4-Di(2-hydroxyethoxy)-2-butyne;2,2'-(But-2-yne-1,4-diylbis(oxy))diethanol;Butynediol ethoxylat
• CAS NO: 1606-85-5
• Molecular Formula: C₈H₁₄O₄
• Molecular Weight: 174.19
• EINECS: 216-526-0
• Product Categories: Acetylenes;Acetylenic Alcohols & Their Derivatives
• Mol File: 1606-85-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 225.17°C (rough estimate)
• Flash Point: >230 °F
• Appearance: clear yellow to brown viscous liquid
• Density: 1.144 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.28E-05mmHg at 25°C
• Refractive Index: n20/D 1.485(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.95±0.10(Predicted)
• CAS DataBase Reference: 1,4-Bis(2-hydroxyethoxy)-2-butyne(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Bis(2-hydroxyethoxy)-2-butyne(1606-85-5)
• EPA Substance Registry System: 1,4-Bis(2-hydroxyethoxy)-2-butyne(1606-85-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 1606-85-5(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow to brown viscous liquid

Uses

1,4-Bis(2-hydroxyethoxy)-2-butyne is used as a brightener for nickel electroplating as well as in the dyeing of acryilic fibers.

InChI:InChI=1/C8H14O4/c9-3-7-11-5-1-2-6-12-8-4-10/h9-10H,3-8H2

Synthetic route

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol ditrityl ether → 2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5)

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran; methanol at 30℃; Inert atmosphere;	73%

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol ditrityl ether → 2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5)

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran; methanol at 30℃; Inert atmosphere;	73%

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → 1,4-bis(2-bromoethoxy)-2-butyne (1426937-56-5)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0℃; Inert atmosphere;	76%

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) + bromoacetic acid tert-butyl ester (5292-43-3) → 3,6,11,14-tetraoxa-8-hexadecyne-1,16-dioic acid di-tert-butyl ester (727729-25-1)

Conditions	Yield
Stage #1: 2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 2h; Stage #2: bromoacetic acid tert-butyl ester In N,N-dimethyl-formamide at 0 - 20℃;	68%

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → (Z)-2,2'-(but-2-ene-1,4-diylbis(oxy))diethanol (1311149-75-3)

Conditions	Yield
Stage #1: 2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol With pyridine In ethyl acetate at 20℃; for 1h; Inert atmosphere; Stage #2: With hydrogen In ethyl acetate at 20℃; for 24h; Inert atmosphere;	60%

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → 1,3,6,11-tetraoxa-2-thiacyclotridec-8-yne 2-oxide

Conditions	Yield
With dmap; thionyl chloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; Inert atmosphere;	50%

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) + 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate (13992-25-1) → C22H33N3O13 (1426937-70-3)

Conditions	Yield
With chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) In 1,4-dioxane at 20℃; Inert atmosphere;	45%

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → 2,2’-(butane-1,4-diylbis(oxy))bis(ethan-1-ol) (21159-68-2)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 48h;	42%

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) + C18H22O8 (1172114-49-6) → C26H32O10 (1200091-24-2)

Conditions	Yield
With Chirazyme-L9; sodium sulfate In tert-butyl methyl ether at 45℃; for 120h;	40%

2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranosyl-(1→1)-2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranoside (23103-34-6) + 2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → C40H60N6O23 (1426937-72-5)

Conditions	Yield
With chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) In 1,4-dioxane at 20℃; Inert atmosphere;	35%

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → 2,2'-[2,3-diiodo-2-butene-1,4-diylbis(oxy)]-bis-ethanol

Conditions	Yield
With I2; Ki In water	24%

formic acid (64-18-6) + 2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → 1,4-Bis(1-hydroxyethoxy)-2-butyne diformate

Conditions	Yield
for 4h; Heating; Yield given;

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → 3,6,11,14-tetraoxa-8-hexadecyne-1,16-dioic acid

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide / 2 h / 0 °C 1.2: 68 percent / dimethylformamide / 0 - 20 °C 2.1: 98 percent / aq. HCl / diethyl ether / 2 h / 20 °C View Scheme

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → 3,6,11,14-tetraoxa-8-hexadecyne-1,16-dioic acid bis(2,5-dioxopyrrolidin-1-yl) ester (727729-29-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: NaH / dimethylformamide / 2 h / 0 °C 1.2: 68 percent / dimethylformamide / 0 - 20 °C 2.1: 98 percent / aq. HCl / diethyl ether / 2 h / 20 °C 3.1: 85 percent / pyridine / acetonitrile / 3 h / 20 °C View Scheme

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → C22H31Br2N3O11 (1426937-78-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) / 1,4-dioxane / 20 °C / Inert atmosphere 2: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 °C / Inert atmosphere View Scheme

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → C22H31N9O11 (1426937-71-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) / 1,4-dioxane / 20 °C / Inert atmosphere 2: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 °C / Inert atmosphere 3: sodium azide / N,N-dimethyl-formamide / 2 h / 70 °C View Scheme

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → C40H56N18O19 (1426937-73-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) / 1,4-dioxane / 20 °C / Inert atmosphere 2: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 °C / Inert atmosphere 3: sodium azide / N,N-dimethyl-formamide / 5 h / 70 °C View Scheme

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → C36H50O20S2 (1426937-59-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 °C / Inert atmosphere 2: triethylamine / acetonitrile / 8 h / 20 °C View Scheme

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → C40H56Br4N6O19

Conditions	Yield
Multi-step reaction with 2 steps 1: chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) / 1,4-dioxane / 20 °C / Inert atmosphere 2: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 °C / Inert atmosphere View Scheme

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → C50H69N3O29S2 (1426937-61-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 °C / Inert atmosphere 2: triethylamine / acetonitrile / 8 h / 20 °C 3: chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) / 1,4-dioxane / 20 °C / Inert atmosphere View Scheme

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → C26H45N3O17S2 (1426937-62-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 °C / Inert atmosphere 2: triethylamine / acetonitrile / 8 h / 20 °C 3: chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) / 1,4-dioxane / 20 °C / Inert atmosphere 4: triethylamine / water; methanol / 20 °C View Scheme

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) + 1,1,1,3,5,5,5-heptamethyltrisiloxan (1873-88-7) → C15H36O6Si3

Conditions	Yield
With dihydrogen hexachloroplatinate In isopropyl alcohol at 110℃; for 3h; Inert atmosphere;

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → (Z)-1,3,6,11-tetraoxa-2-thiacyclotridec-8-ene 2-oxide

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine / ethyl acetate / 1 h / 20 °C / Inert atmosphere 1.2: 24 h / 20 °C / Inert atmosphere 2.1: thionyl chloride; N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0 °C / Inert atmosphere View Scheme

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol (1606-85-5) → 1,3,6,11-tetraoxa-2-thiacyclotridecane 2-oxide

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen; palladium 10% on activated carbon / methanol / 48 h / 20 °C 2: thionyl chloride; N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0 °C / Inert atmosphere View Scheme

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