• Name

  1,4-Bis(2-hydroxyethoxy)-2-butyne

• EINECS 216-526-0
• CAS No. 1606-85-5
• Article Data6
• CAS DataBase
• Density 1.148 g/cm³
• Solubility
• Melting Point
• Formula C₈H₁₄O₄
• Boiling Point 322.1 °C at 760 mmHg
• Molecular Weight 174.197
• Flash Point 148.6 °C
• Transport Information
• Appearance clear yellow to brown viscous liquid
• Safety 26-37/39
• Risk Codes 36/37/38
• Molecular Structure
• Hazard Symbols Xi
• Synonyms Ethanol,2,2'-(2-butynylenedioxy)di- (6CI,7CI,8CI);1,4-Di(b-hydroxyethoxy)-2-butyne;2,2'-(2-Butyne-1,4-diyldioxy)diethanol;2-Butyne-1,4-diol, bis(b-hydroxyethyl) ether;Ferasine;NSC 73709;Butynediol ethoxylate;
• PSA 58.92000
• LogP -0.99240

Synthetic route

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol ditrityl ether

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

1426937-56-5

1,4-bis(2-bromoethoxy)-2-butyne

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

5292-43-3

bromoacetic acid tert-butyl ester

727729-25-1

3,6,11,14-tetraoxa-8-hexadecyne-1,16-dioic acid di-tert-butyl ester

Conditions

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%

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

1311149-75-3

(Z)-2,2'-(but-2-ene-1,4-diylbis(oxy))diethanol

Conditions

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%

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

1,3,6,11-tetraoxa-2-thiacyclotridec-8-yne 2-oxide

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

13992-25-1

1-azido-1-deoxy-β-D-glucopyranoside tetraacetate

1426937-70-3

C22H33N3O13

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

21159-68-2

2,2’-(butane-1,4-diylbis(oxy))bis(ethan-1-ol)

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

1172114-49-6

C18H22O8

1200091-24-2

C26H32O10

Conditions

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

23103-34-6

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

1426937-72-5

C40H60N6O23

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

2,2'-[2,3-diiodo-2-butene-1,4-diylbis(oxy)]-bis-ethanol

Conditions

Conditions	Yield
With I2; Ki In water	24%

64-18-6

formic acid

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

1,4-Bis(1-hydroxyethoxy)-2-butyne diformate

Conditions

Conditions	Yield
for 4h; Heating; Yield given;

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

3,6,11,14-tetraoxa-8-hexadecyne-1,16-dioic acid

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

727729-29-5

3,6,11,14-tetraoxa-8-hexadecyne-1,16-dioic acid bis(2,5-dioxopyrrolidin-1-yl) ester

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

1426937-78-1

C22H31Br2N3O11

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

1426937-71-4

C22H31N9O11

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

1426937-73-6

C40H56N18O19

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

1426937-59-8

C36H50O20S2

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

C40H56Br4N6O19

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

1426937-61-2

C50H69N3O29S2

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

1426937-62-3

C26H45N3O17S2

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

1873-88-7

1,1,1,3,5,5,5-heptamethyltrisiloxan

C15H36O6Si3

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

(Z)-1,3,6,11-tetraoxa-2-thiacyclotridec-8-ene 2-oxide

Conditions

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

1606-85-5

2,2'-(but-2-yne-1,4-diylbis(oxy))diethanol

1,3,6,11-tetraoxa-2-thiacyclotridecane 2-oxide

Conditions

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

1,4-Bis(2-hydroxyethoxy)-2-butyne Specification