Product Name

  • Name

    3-Prop-2-ynoxypropane-1,2-diol

  • EINECS 237-012-2
  • CAS No. 13580-38-6
  • Article Data10
  • CAS DataBase
  • Density 1.151 g/cm3
  • Solubility
  • Melting Point
  • Formula C6H10O3
  • Boiling Point 268.666 °C at 760 mmHg
  • Molecular Weight 130.144
  • Flash Point 116.285 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 13580-38-6 (3-Prop-2-ynoxypropane-1,2-diol)
  • Hazard Symbols
  • Synonyms 1,2-Propanediol,3-(2-propynyloxy)- (8CI,9CI);3-(2-Propynyloxy)-1,2-propanediol;Monopropargylylglycerol ether;NSC 215123;Propargyl-oxo-propane-2,3-dihydroxy;
  • PSA 49.69000
  • LogP -1.01060

Synthetic route

prop-2-ynyloxymethyl-oxirane
18180-30-8

prop-2-ynyloxymethyl-oxirane

3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

Conditions
ConditionsYield
With water at 100℃;96%
propargyl bromide
106-96-7

propargyl bromide

(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol
100-79-8

(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol

3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

Conditions
ConditionsYield
Stage #1: propargyl bromide; (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol With sodium hydride In tetrahydrofuran Reflux;
Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water at 20℃; for 8h;		90%
4-(prop-2-yn-1-yloxymethyl)-2,2-dimethyl-1,3-dioxolane

4-(prop-2-yn-1-yloxymethyl)-2,2-dimethyl-1,3-dioxolane

3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran at 20℃;75%
With hydrogenchloride; water In tert-butyl methyl ether at 20 - 25℃; for 6h; Inert atmosphere; Industry scale;85 %Chromat.
With methanol
oxiranyl-methanol
556-52-5

oxiranyl-methanol

propargyl alcohol
107-19-7

propargyl alcohol

3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

Conditions
ConditionsYield
In N,N-dimethyl-formamide51%
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1,2-di-O-tert-butyldimethylsilyl-3-(prop-2-yn-1-yloxy)propan-1,2-diol

1,2-di-O-tert-butyldimethylsilyl-3-(prop-2-yn-1-yloxy)propan-1,2-diol

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide80%
sodium hypochlorite
7681-52-9

sodium hypochlorite

3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

3-(2,3,3-triiodo-2-propenyloxy)-propane-1,2-diol

3-(2,3,3-triiodo-2-propenyloxy)-propane-1,2-diol

Conditions
ConditionsYield
With sodium hydroxide; Ki; aqueous H2SO4 In water76%
With sodium hydroxide; Ki; aqueous H2SO4 In water76%
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

4‐((prop‐2‐yn‐1‐yloxy)methyl)‐1,3‐dioxolan‐2‐one
949015-02-5

4‐((prop‐2‐yn‐1‐yloxy)methyl)‐1,3‐dioxolan‐2‐one

Conditions
ConditionsYield
With tetrabutylammomium bromide at 180℃; under 8250.83 Torr; for 0.05h; Flow reactor;69%
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

trityl chloride
76-83-5

trityl chloride

1-(prop-2-yn-1-yloxy)-3-(trityloxy)propan-2-ol

1-(prop-2-yn-1-yloxy)-3-(trityloxy)propan-2-ol

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;66%
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

(2,3-dihexadecanoyl)-(1-propargyloxy)propionate

(2,3-dihexadecanoyl)-(1-propargyloxy)propionate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Steglich Esterification;51%
lauric acid
143-07-7

lauric acid

3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

(2,3-didodecanoyl)-(1-propargyloxy)propionate

(2,3-didodecanoyl)-(1-propargyloxy)propionate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Steglich Esterification;48%
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

3-(2,3-diiodo-2-propenyloxy)-propane-1,2-diol

3-(2,3-diiodo-2-propenyloxy)-propane-1,2-diol

Conditions
ConditionsYield
With I2; Ki In water
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

2-(prop-2-yn-1-yloxy)acetaldehyde
801294-16-6

2-(prop-2-yn-1-yloxy)acetaldehyde

Conditions
ConditionsYield
With sodium periodate; water at 10 - 25℃; pH=~ 7; Inert atmosphere; Industry scale;
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1-(prop-2-yn-1-yloxy)-3-(trityloxy)propan-2-one

1-(prop-2-yn-1-yloxy)-3-(trityloxy)propan-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: dipyridinium dichromate / dichloromethane / 20 °C / Molecular sieve
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1-hydroxy-3-(prop-2-yn-1-yloxy)propan-2-one

1-hydroxy-3-(prop-2-yn-1-yloxy)propan-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: dipyridinium dichromate / dichloromethane / 20 °C / Molecular sieve
3: trifluoroacetic acid / 20 °C
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1-{2-[2-(2-hydroxyethoxy)ethoxy]ethyl}-4-{[(1,2-didodecanoyloxy-carbonyl)propyloxy]methoxy}-1,2,3-triazole

1-{2-[2-(2-hydroxyethoxy)ethoxy]ethyl}-4-{[(1,2-didodecanoyloxy-carbonyl)propyloxy]methoxy}-1,2,3-triazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
2: copper(I) bromide; N,N,N',N'',N'''-pentamethyldiethylenetriamine / N,N-dimethyl-formamide; dichloromethane / 16 h / 20 °C
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1-{2-[2-(2-(β-D-glucopyranosyloxy)ethoxy)ethoxy]ethyl}-4-{[(1,2-di-dodecanoyloxycarbonyl)propyloxy]methoxy}-1,2,3-triazole

1-{2-[2-(2-(β-D-glucopyranosyloxy)ethoxy)ethoxy]ethyl}-4-{[(1,2-di-dodecanoyloxycarbonyl)propyloxy]methoxy}-1,2,3-triazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
2: copper(I) bromide; N,N,N',N'',N'''-pentamethyldiethylenetriamine / N,N-dimethyl-formamide; dichloromethane / 16 h / 20 °C
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1-{2-[2-(2-(β-D-galactopyranosyl-(1→4)β-D-glucopyranosyloxy)ethoxy)ethoxy]ethyl}-4-{[(1,2-didodecanoyloxycarbonyl)propyloxy]methoxy}-1,2,3-triazole

1-{2-[2-(2-(β-D-galactopyranosyl-(1→4)β-D-glucopyranosyloxy)ethoxy)ethoxy]ethyl}-4-{[(1,2-didodecanoyloxycarbonyl)propyloxy]methoxy}-1,2,3-triazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
2: copper(I) bromide; N,N,N',N'',N'''-pentamethyldiethylenetriamine / N,N-dimethyl-formamide; dichloromethane / 16 h / 20 °C
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1-{2-[2-(2-hydroxyethoxy)ethoxy]ethyl}-4-{[(1,2-dihexadecanoyloxy-carbonyl)propyloxy]methoxy}-1,2,3-triazole

1-{2-[2-(2-hydroxyethoxy)ethoxy]ethyl}-4-{[(1,2-dihexadecanoyloxy-carbonyl)propyloxy]methoxy}-1,2,3-triazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
2: copper(I) bromide; N,N,N',N'',N'''-pentamethyldiethylenetriamine / N,N-dimethyl-formamide; dichloromethane / 16 h / 20 °C
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1-{2-[2-(2-(β-D-glucopyranosyloxy)ethoxy)ethoxy]ethyl}-4-{[(1,2-di-hexadecanoyloxycarbonyl)propyloxy]methoxy}-1,2,3-triazole

1-{2-[2-(2-(β-D-glucopyranosyloxy)ethoxy)ethoxy]ethyl}-4-{[(1,2-di-hexadecanoyloxycarbonyl)propyloxy]methoxy}-1,2,3-triazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
2: copper(I) bromide; N,N,N',N'',N'''-pentamethyldiethylenetriamine / N,N-dimethyl-formamide; dichloromethane / 16 h / 20 °C
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1-{2-[2-(2-(β-D-galactopyranosyl-(1→4)β-D-glucopyranosyloxy)ethoxy)ethoxy]ethyl}-4-{[(1,2-dihexadecanoyloxycarbonyl)propyl-oxy]methoxy}-1,2,3-triazole

1-{2-[2-(2-(β-D-galactopyranosyl-(1→4)β-D-glucopyranosyloxy)ethoxy)ethoxy]ethyl}-4-{[(1,2-dihexadecanoyloxycarbonyl)propyl-oxy]methoxy}-1,2,3-triazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
2: copper(I) bromide; N,N,N',N'',N'''-pentamethyldiethylenetriamine / N,N-dimethyl-formamide; dichloromethane / 16 h / 20 °C
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1,3-di-[1-(4-deoxypodophyllotoxin-4β-yl)-1,2,3-triazol-4-yl-methoxy]-propan-2-ol

1,3-di-[1-(4-deoxypodophyllotoxin-4β-yl)-1,2,3-triazol-4-yl-methoxy]-propan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide
2.1: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 20 °C
3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
3.2: Inert atmosphere; Reflux
4.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
5.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 4 h / 20 °C
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1,3-di-[1-(4-deoxy-4′-demethylpodophyllotoxin-4β-yl)-1,2,3-triazol-4-yl-methoxy]-propan-2-ol

1,3-di-[1-(4-deoxy-4′-demethylpodophyllotoxin-4β-yl)-1,2,3-triazol-4-yl-methoxy]-propan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide
2.1: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 20 °C
3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
3.2: Inert atmosphere; Reflux
4.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
5.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 4 h / 20 °C
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

2-O-tert-butyldimethylsilyl-3-(prop-2-yn-1-yloxy)propan-1,2-diol

2-O-tert-butyldimethylsilyl-3-(prop-2-yn-1-yloxy)propan-1,2-diol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1H-imidazole / N,N-dimethyl-formamide
2: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 20 °C
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

2-O-tert-butyldimethylsilyl-1,3-di-(prop-2-yn-1-yloxy)propan-1,2-diol

2-O-tert-butyldimethylsilyl-1,3-di-(prop-2-yn-1-yloxy)propan-1,2-diol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide
2.1: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 20 °C
3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
3.2: Inert atmosphere; Reflux
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1,3-bis(prop-2-yn-1-yloxy)propane-2-ol
16169-22-5

1,3-bis(prop-2-yn-1-yloxy)propane-2-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide
2.1: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 20 °C
3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
3.2: Inert atmosphere; Reflux
4.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1,3-di-(prop-2-yn-1-yloxy)prop-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

1,3-di-(prop-2-yn-1-yloxy)prop-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide
2.1: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 20 °C
3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
3.2: Inert atmosphere; Reflux
4.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
5.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1,3-di-(prop-2-yn-1-yloxy)prop-2-yl β-D-glucopyranoside

1,3-di-(prop-2-yn-1-yloxy)prop-2-yl β-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide
2.1: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 20 °C
3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
3.2: Inert atmosphere; Reflux
4.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
5.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere
6.1: sodium methylate / methanol
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

1,3-di-(prop-2-yn-1-yloxy)prop-2-yl 2,3,4,6-tetra-O-butyryl-β-D-glucopyranoside

1,3-di-(prop-2-yn-1-yloxy)prop-2-yl 2,3,4,6-tetra-O-butyryl-β-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide
2.1: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 20 °C
3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
3.2: Inert atmosphere; Reflux
4.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C
5.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere
6.1: sodium methylate / methanol
7.1: pyridine / 12 h / 0 - 20 °C
View Scheme
3-(prop-2-yn-1-yloxy)propan-1,2-diol
13580-38-6

3-(prop-2-yn-1-yloxy)propan-1,2-diol

stearic acid
57-11-4

stearic acid

C24H44O4

C24H44O4

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride

3-Prop-2-ynoxypropane-1,2-diol Specification

The 3-Prop-2-ynoxypropane-1,2-diol, with the CAS registry number 13580-38-6, is also known as 1,2-Propanediol, 3-(2-propyn-1-yloxy)-. Its EINECS registry number is 237-012-2. This chemical's molecular formula is C6H10O3 and molecular weight is 130.14. What's more, its systematic name is called 3-(2-Propyn-1-yloxy)-1,2-propanediol.

Physical properties about 3-Prop-2-ynoxypropane-1,2-diol are: (1)ACD/LogP: -0.5; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.50; (4)ACD/LogD (pH 7.4): -0.50; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 12.74; (8)ACD/KOC (pH 7.4): 12.74; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 49.69 Å2; (13)Index of Refraction: 1.486; (14)Molar Refractivity: 32.448 cm3; (15)Molar Volume: 113.091 cm3; (16)Polarizability: 12.863×10-24cm3; (17)Surface Tension: 49.76 dyne/cm; (18)Density: 1.151 g/cm3; (19)Flash Point: 116.285 °C; (20)Enthalpy of Vaporization: 58.842 kJ/mol; (21)Boiling Point: 268.666 °C at 760 mmHg; (22)Vapour Pressure: 0.00100 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: OCC(O)COCC#C
(2) InChI: InChI=1S/C6H10O3/c1-2-3-9-5-6(8)4-7/h1,6-8H,3-5H2
(3) InChIKey: WZGADLPIFFITSG-UHFFFAOYSA-N 

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