2-[(Acetyloxy)methoxy]ethyl acetate supplier

Name
2-[(Acetyloxy)methoxy]ethyl acetate
EINECS 261-686-7
CAS No. 59278-00-1
Article Data14
CAS DataBase
Density 1.119 g/cm³
Solubility
Melting Point
Formula C₇H₁₂O₅
Boiling Point 225.2 °C at 760 mmHg
Molecular Weight 176.169
Flash Point 90.9 °C
Transport Information
Appearance clear, colourless or yellowish liquid
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms Ethanol,2-(hydroxymethoxy)-, diacetate (6CI);Ethanol, 2-[(acetyloxy)methoxy]-, acetate(9CI);(2-Acetoxyethoxy)methyl acetate;1,4-Diacetoxy-2-oxabutane;2-Acetoxyethyl acetoxymethyl ether;2-Oxa-1,4-butanediol diacetate;
PSA 61.83000
LogP 0.08670

Synthetic route

: 1,3-epoxycyclopentane

: 108-24-7
acetic anhydride

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 35 - 40℃; for 0.833333h; Reagent/catalyst; Temperature;	91%

: 646-06-0
1,3-DIOXOLANE

: 506-96-7
Acetyl bromide

: 127-09-3
sodium acetate

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

Conditions

Conditions	Yield
Stage #1: 1,3-DIOXOLANE; Acetyl bromide Stage #2: sodium acetate With acetic acid at 110℃; for 1h;	77%

...Expand

: 646-06-0
1,3-DIOXOLANE

: 108-24-7
acetic anhydride

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

Conditions

Conditions	Yield
With sulfuric acid Ambient temperature;	74%
With sulfuric acid at -5 - 20℃;	52%
With iron(III) chloride

: 646-06-0
1,3-DIOXOLANE

: 506-96-7
Acetyl bromide

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

Conditions

Conditions	Yield
With sodium acetate In acetic acid at 110℃; for 1h;	60%

: 646-06-0
1,3-DIOXOLANE

: 7664-93-9
sulfuric acid

: 127-09-3
sodium acetate

: 108-24-7
acetic anhydride

A: 111-55-7
ethylene glycol diacetate

B: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

C: 90114-17-3
1,2-bis(acetoxy-methyloxy)ethane

...Expand

: 646-06-0
1,3-DIOXOLANE

: 108-24-7
acetic anhydride

A: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

B ethylene glycol diacetat; ethylene glycol-bis-acetoxymethyl ether: ethylene glycol diacetat; ethylene glycol-bis-acetoxymethyl ether

Conditions

Conditions	Yield
With sulfuric acid at 20℃; Versetzen des abgekuehlten Reaktionsgemisches mit Natriumacetat;

...Expand

: 17495-10-2
N2-acetyl-7-benzylguanine

A: 9-(2-acetoxyethoxy)methyl-7-benzyl-N2-acetylguaninium acetate

B: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

Conditions

Conditions	Yield
In N,N-dimethyl-formamide

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 3056-33-5
2,9-diacetylguanine

: 75128-73-3
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

Conditions

Conditions	Yield
at 105℃; for 80h;	95.1%
With toluene-4-sulfonic acid In toluene at 110℃; Temperature; Large scale;	94.3%

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 1214-39-7
6-benzyladenine

: 173205-63-5
9-<(2-acetoxyethoxy)methyl>-6-benzylaminopurine

Conditions

Conditions	Yield
With aluminum oxide; silica gel for 0.0666667h; microwave irradiation;	95%

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 126094-26-6
5-Methylimidazo<4,5-d><1,3>thiazine-7(3H)-thione

: 136369-77-2
3-(2-Acetoxyethoxymethyl)-5-methylimidazo<4,5-d><1,3>thiazine-7(3H)-thione

Conditions

Conditions	Yield
at 150℃; for 0.333333h;	94%

: diacetyl guanine

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 75128-73-3
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

Conditions

Conditions	Yield
In methanol; dichloromethane	94%

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 87-42-3
6-chloropurine

: 81777-47-1
9-<(2-acetoxyethoxy)methyl>-6-chloropurine

Conditions

Conditions	Yield
With aluminum oxide; silica gel for 0.0666667h; microwave irradiation;	93%

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: trimethylsilylated 2-thioadenine

: 116457-82-0
9-(2-acetoxyethoxy methyl)-2-thioadenine

Conditions

Conditions	Yield
cesium iodide In acetonitrile for 2h; Heating;	92%

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 171048-65-0
6-(3,5-dimethylbenzyl)-5-ethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

: 444788-50-5
1-(2-acetoxyethoxymethyl)-6-(3,5-dimethylbenzyl)-5-ethyluracil

Conditions

Conditions	Yield
Stage #1: 2-acetoxyethyl acetoxymethyl ether; 6-(3,5-dimethylbenzyl)-5-ethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione With chloro-trimethyl-silane; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 14.3333h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water	92%

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 31111-39-4
2,4,6-tris(trimethylsilyloxy)pyrimidine

: 154021-74-6
1-<(2-acetoxyethoxy)methyl>barbituric acid

Conditions

Conditions	Yield
With tin(IV) chloride In dichloromethane at 18 - 25℃;	91%

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 5451-40-1
2,6 dichloropurine

: 59277-99-5
9-<(2-acetoxyethoxy)methyl>-2,6-dichloropurine

Conditions

Conditions	Yield
With aluminum oxide; silica gel for 0.1h; microwave irradiation;	91%

: diacetylguanine

: diacetyl guanine

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 75128-73-3
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

Conditions

Conditions	Yield
In methanol; toluene	91%

...Expand

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 69304-43-4
1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N4-benzoylcytosine

: 933063-81-1
1-{2-O-[(2-acetoxyethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}-N4-benzoylcytosine

Conditions

Conditions	Yield
With tin(IV) chloride In 1,2-dichloro-ethane at -12℃; for 0.333333h;	87%
With tin(IV) chloride In 1,2-dichloro-ethane at -12℃; for 0.333333h;

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 108-24-7
acetic anhydride

: 118-00-3
G

A: 75128-73-3
2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

B: 91702-60-2
7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 100℃; for 20h;	A 86% B 0.5%
With sulfuric acid at 100℃; for 24h; Product distribution; other acid caclysts, temperature time, solvents; transpurination reaction of guanosine under various conditions;	A 43% B 35%
With phosphoric acid at 100℃; for 24h; Title compound not separated from byproducts;	A 47 % Chromat. B 38 % Chromat.

...Expand

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 69304-38-7
3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

: 933063-80-0
1-{2-O-[(2-acetoxyethoxy)methyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl}uracil

Conditions

Conditions	Yield
With tin(IV) chloride In 1,2-dichloro-ethane at -12℃; for 0.333333h;	86%
With tin(IV) chloride In 1,2-dichloro-ethane at -12℃; for 0.333333h;
With tin(IV) chloride In dichloromethane at -12℃; for 0.333333h;

: 51-20-7
5-bromouracil

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 78692-73-6
1-<(2-acetoxyethoxy)methyl>-5-bromouracil

Conditions

Conditions	Yield
Stage #1: 5-bromouracil With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 15h; Stage #2: 2-acetoxyethyl acetoxymethyl ether With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 24h;	85%
With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; zinc(II) iodide 1.) DMF, 100 deg C, 7 h; Yield given. Multistep reaction;

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 1210-66-8
N-phenyl-9H-purin-6-amine

: 9-[(2-acetoxyethoxy)methyl]-6-phenylaminopurine

Conditions

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	85%

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 7288-28-0
2,4-bis(trimethylsiloxy)-5-methylpyrimidine

: 81777-42-6
1-<(2-acetoxyethoxy)methyl>thymine

Conditions

Conditions	Yield
With ammonium sulfate; isocyanate de chlorosulfonyle In acetonitrile for 2h; Heating;	83%
With 1,1,1,3,3,3-hexamethyl-disilazane; potassium iodide-doped natural phosphate	45%
natural phosphate In acetonitrile for 3h; Heating;
iodine-doped natural phosphate In acetonitrile Heating;

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 185408-97-3
2-chloro-N-phenyl-9H-purin-6-amine

: 9-[(2-acetoxyethoxy)methyl]-2-chloro-6-phenylaminopurine

Conditions

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	83%

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 7674-45-5
N6-Cyclohexyladenine

: 9-[(2-acetoxyethoxy)methyl]-6-cyclohexylaminopurine

Conditions

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	82%

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 1225549-78-9
6-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-7-one

A: 1542213-33-1
3-[(2-acetoxyethoxy)methyl]-6-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-7-one

B: 1542213-35-3
4-[(2-acetoxyethoxy)methyl]-6-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-7-one

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 3h; Reagent/catalyst; Solvent; Temperature; Time; Vorbrueggen Nucleoside Synthesis;	A 2% B 82%
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 0.2h; Vorbrueggen Nucleoside Synthesis; Overall yield = 48 %;	A 36% B 12%

...Expand

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 52562-51-3, 63202-26-6, 73370-77-1, 73370-78-2, 73370-81-7, 73370-82-8, 73370-85-1, 73370-86-2
1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)indazole

: 162894-30-6
1-<(2-acetoxyethyl)methyl>indazole

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In chlorobenzene at 130℃; for 0.25h;	81%

: 39639-45-7
(2-chloro-9H-purin-6-yl)-cyclohexyl-amine

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 9-[(2-acetoxyethoxy)methyl]-2-chloro-6-cyclohexylaminopurine

Conditions

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	81%

: 55321-99-8
3-oxo-3,4-dihydropyrazine-2-carboxamide

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 2-((3-carbamoyl-2-oxopyrazin-1(2H)-yl) methoxy) ethyl acetate

Conditions

Conditions	Yield
Stage #1: 3-oxo-3,4-dihydropyrazine-2-carboxamide With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 1h; Inert atmosphere; Reflux; Stage #2: 2-acetoxyethyl acetoxymethyl ether With tin(IV) chloride In acetonitrile at 20℃; Inert atmosphere; Cooling with ice;	81%

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 486999-72-8
6-benzyl-5-but-2-enyl-1H-pyrimidine-2,4-dione

: 486999-81-9
1-((2-acetoxyethoxy)methyl)-6-benzyl-5-(2-butenyl)-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
Stage #1: 2-acetoxyethyl acetoxymethyl ether; 6-benzyl-5-but-2-enyl-1H-pyrimidine-2,4-dione With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane Stage #2: With tin(IV) chloride In dichloromethane at 0 - 20℃;	80%

: 5446-36-6
(7(9)H-purin-6-yl)-p-tolyl-amine

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 9-[(2-acetoxyethoxy)methyl]-6-(p-tolylamino)purine

Conditions

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	80%

: N-(4-methoxyphenyl)-9H-purine-6-amine

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 9-[(2-acetoxyethoxy)methyl]-6-(p-methoxyphenylamino)purine

Conditions

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	80%

: (4-ethoxy-phenyl)-(9H-purin-6-yl)-amine

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 9-[(2-acetoxyethoxy)methyl]-6-(p-ethoxyphenylamino)purine

Conditions

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	79%

: 39639-49-1
2-chloro-6-(4-methylphenyl)amino-9H-purin

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 9-[(2-acetoxyethoxy)methyl]-2-chloro-6-(p-tolylamino)purine

Conditions

Conditions	Yield
With aluminum oxide; silica gel for 0.133333h; microwave irradiation;	78%

: 59278-00-1
2-acetoxyethyl acetoxymethyl ether

: 263239-79-8
5-(3-isopropyl-adamantan-1-yl)-2,4-bis-trimethylsilanyloxy-pyrimidine

: 263239-81-2
acetic acid 2-[5-(3-isopropyl-adamantan-1-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy]-ethyl ester

Conditions

Conditions	Yield
With tin(IV) chloride In dichloromethane for 3h; Alkylation; Heating;	77%

2-[(Acetyloxy)methoxy]ethyl acetate Specification

The Ethanol,2-[(acetyloxy)methoxy]-, 1-acetate, with CAS registry number 59278-00-1, belongs to the following product categories: (1)Intermediates & Fine Chemicals; (2)Pharmaceuticals. It has the systematic name of [2-(acetyloxy)ethoxy]methyl acetate. This chemical is a kind of bright yellow liquid. The main use of this chemical is the intermediate for the preparation of Acyclovir-d4.

Physical properties of Ethanol,2-[(acetyloxy)methoxy]-, 1-acetate: (1)ACD/LogP: 0.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.32; (4)ACD/LogD (pH 7.4): 0.32; (5)ACD/BCF (pH 5.5): 1.03; (6)ACD/BCF (pH 7.4): 1.03; (7)ACD/KOC (pH 5.5): 35.59; (8)ACD/KOC (pH 7.4): 35.59; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 61.83 Å²; (13)Index of Refraction: 1.419; (14)Molar Refractivity: 39.77 cm³; (15)Molar Volume: 157.4 cm³; (16)Polarizability: 15.76×10^-24cm³; (17)Surface Tension: 33.8 dyne/cm; (18)Enthalpy of Vaporization: 46.18 kJ/mol; (19)Vapour Pressure: 0.0874 mmHg at 25°C.

Preparation: this chemical can be prepared by acetyl bromide and [1,3]dioxolane. This reaction will need reagent sodium acetate and solvent acetic acid. The reaction time is 1 hour(s) with reaction temperature of 110 ℃. The yield is about 60%.

Uses of Ethanol,2-[(acetyloxy)methoxy]-, 1-acetate: it can be used to produce 9-(2-acetoxyethoxymethyl)-2-thioadenine. This reaction will need solvent acetonitrile. The reaction time is 2 hour(s). The yield is about 92%.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCOCCOC(=O)C)C
(2)InChI: InChI=1/C7H12O5/c1-6(8)11-4-3-10-5-12-7(2)9/h3-5H2,1-2H3
(3)InChIKey: XFEQOLXBMLXKDE-UHFFFAOYAT
(4)Std. InChI: InChI=1S/C7H12O5/c1-6(8)11-4-3-10-5-12-7(2)9/h3-5H2,1-2H3
(5)Std. InChIKey: XFEQOLXBMLXKDE-UHFFFAOYSA-N

Product Name

2-[(Acetyloxy)methoxy]ethyl acetate

Synthetic route

2-[(Acetyloxy)methoxy]ethyl acetate Specification

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