6704-31-0

Basic information

• Product Name: 3-Oxetanone
• Synonyms: Oxetan-3-one;1,3-Epoxy-2-propanone;3-Oxetanone;oxentan-3-on;3-oxetanon;3-Oxooxetane, 1,3-Epoxypropan-2-one;Oxetan-3-one 95%;3-Oxetanone, 98%+
• CAS NO: 6704-31-0
• Molecular Formula: C₃H₄O₂
• Molecular Weight: 72.06
• Mol File: 6704-31-0.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 140 °C
• Flash Point: 53 °C
• Appearance: /
• Density: 1.231
• Refractive Index: 1.426
• Storage Temp.: ?20°C
• Solubility: Miscible with tetrahydrofuran.
• CAS DataBase Reference: 3-Oxetanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Oxetanone(6704-31-0)
• EPA Substance Registry System: 3-Oxetanone(6704-31-0)

Safety Data

• Hazard Codes: Xn
• Statements: 10-22-37/38-41-43
• Safety Statements: 16-26-36/37/39
• RIDADR: 1993
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 6704-31-0(Hazardous Substances Data)

Usage

Description

3-Oxetanone is a colorless liquid that may polymerize over time during storage. It is a chemical compound with the potential for various applications in the field of pharmaceuticals and theoretical studies.

Uses

Used in Pharmaceutical Industry:
3-Oxetanone is used as a starting material for the preparation of other oxetanes compounds, which are of pharmacological interest. It serves as a key component in the synthesis of various oxetane-containing lead compounds with improved solubility, reduced lipophilicity, and amphiphilicity.
Used in Chemical Research:
3-Oxetanone is considered an object for theoretical studies, contributing to the understanding of its chemical properties and potential applications in various fields.
Used in Organic Synthesis:
3-Oxetanone can be used to synthesize (hydroxymethyl)oxazoles and (hydroxymethyl)thiazoles via a single-step microwave-mediated reaction with primary amides and thioamides, respectively. This makes it a valuable compound for the development of new chemical entities with potential applications in various industries.
Used in the Synthesis of Spirocycles:
3-Oxetanone is also utilized in the creation of oxetane-containing spirocycles through thermal 1,3-dipolar cycloaddition reactions with α-amino acids or secondary α-amino acid esters, further expanding its utility in the synthesis of complex molecular structures.

Synthetic route

C5H8O3 → oxetan-3-one (6704-31-0)

Conditions	Yield
With phosphoric acid In water Reagent/catalyst;	92%

3-chloro-2-oxopropyl-2-bromobenzoate → oxetan-3-one (6704-31-0)

Conditions	Yield
With potassium hydroxide In methanol at 80℃; for 8h; Solvent; Temperature; Reagent/catalyst;	72%

oxetan-3-ol (7748-36-9) → oxetan-3-one (6704-31-0)

Conditions	Yield
With phosphorus pentoxide; triethylamine In dichloromethane; dimethyl sulfoxide at 10 - 40℃; for 2h; Solvent; Reagent/catalyst;	65.3%
With phosphorus pentoxide; dimethyl sulfoxide; triethylamine In dichloromethane at -5 - 5℃;	48%
With pyridine; chromium(VI) oxide In dichloromethane at 5 - 20℃;

3,3-dimethoxyoxetane (922500-97-8) → oxetan-3-one (6704-31-0)

Conditions	Yield
With Montmorillonite K10 clay In dichloromethane for 70h; Heating;	62%

diazomethane (186581-53-3, 908094-01-9) + chloroacetyl chloride (79-04-9) → oxetan-3-one (6704-31-0)

Conditions	Yield
With methanol; diethyl ether; potassium carbonate Erhitzen des isolierten Reaktionsprodukts mit Essigsaeure.;

propargyl alcohol (107-19-7) → oxetan-3-one (6704-31-0)

Conditions	Yield
With (1,1’-biphenyl-2-yl)dicyclohexylphosphine gold bis(trifluoromethanesulfonyl)imidate; bis(trifluoromethanesulfonyl)amide; 5-bromo-1-oxy-nicotinic acid methyl ester In 1,2-dichloro-ethane at 20℃; for 0.5h;

[Rh(OH)(cod)]2 + C13H20O2 → oxetan-3-one (6704-31-0) + (cycloocta-1,5-diene)[η5-pentamethylcyclopentadienyl]rhodium(I)

Conditions	Yield
With caesium carbonate In toluene at 70℃; for 3h; Inert atmosphere;	A n/a B 20 %Spectr.

oxetan-3-one (6704-31-0) + (S)-1-amino-2-(methoxymethyl)pyrrolidine (59983-39-0) → (2S)-2-(methoxymethyl)-N-oxetan-3-ylidine-1-pyrrolidinamine

Conditions	Yield
at 55℃; for 16h; stereoselective reaction;	100%

oxetan-3-one (6704-31-0) + (R)-1-Amino-2-(methoxymethyl)pyrrolidine (72748-99-3) → (2R)-2-(methoxymethyl)-N-oxetan-3-ylidine-1-pyrrolidinamine

Conditions	Yield
at 55℃; for 16h; stereoselective reaction;	100%
at 55℃; for 16h; Inert atmosphere;	83%

oxetan-3-one (6704-31-0) + benzyl 1,4-diazepane-1-carboxylate (117009-97-9) → C16H22N2O3

Conditions	Yield
Stage #1: oxetan-3-one; benzyl 1,4-diazepane-1-carboxylate With acetic acid In 1,2-dichloro-ethane at 20℃; for 2h; Stage #2: With sodium tris(acetoxy)borohydride for 48h;	100%

oxetan-3-one (6704-31-0) + diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → ethyl 2-(oxetan-3-ylidene)acetate (922500-91-2)

Conditions	Yield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: oxetan-3-one In tetrahydrofuran; mineral oil at 20℃; Schlenk technique; Inert atmosphere;	100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0 - 20℃; for 17h; Reagent/catalyst; Cooling with ice;	86%
With sodium hydride In tetrahydrofuran at 20℃;

oxetan-3-one (6704-31-0) + (trimethylsilyl)methylmagnesium chloride (13170-43-9) → 3-((trimethylsilyl)methyl)oxetan-3-ol

Conditions	Yield
In diethyl ether at 0 - 20℃; for 5h; Inert atmosphere;	100%

oxetan-3-one (6704-31-0) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(oxetan-3-yl)piperazine-1-carboxylate

Conditions	Yield
Stage #1: oxetan-3-one; 1-t-Butoxycarbonylpiperazine In 1,2-dichloro-ethane at 20℃; for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 18h; Stage #3: With water In 1,2-dichloro-ethane	99.9%
With Sodium triacetoxy borohydride In 1,2-dichloro-ethane at 20℃;	84%
Stage #1: oxetan-3-one; 1-t-Butoxycarbonylpiperazine In dichloromethane at 20℃; for 4h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;

oxetan-3-one (6704-31-0) + methyl 4-((N-(4-chlorophenyl)piperazine-1-carboxamido)methyl)-3-fluorobenzoate hydrochloride → methyl 4-((N-(4-chlorophenyl)-4-(oxetan-3-yl)piperazine-1-carboxamido)methyl)-3-fluorobenzoate

Conditions	Yield
Stage #1: oxetan-3-one; methyl 4-((N-(4-chlorophenyl)piperazine-1-carboxamido)methyl)-3-fluorobenzoate hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; Stage #2: With water; sodium chloride In dichloromethane	99.9%

oxetan-3-one (6704-31-0) + methyl 3-fluoro-4-((N-(3-methoxyphenyl)piperazine-1-carboxamido)methyl)benzoate hydrochloride → methyl 3-fluoro-4-((N-(3-methoxyphenyl)-4-(oxetan-3-yl)piperazine-1-carboxamido)methyl)benzoate

Conditions	Yield
Stage #1: oxetan-3-one; methyl 3-fluoro-4-((N-(3-methoxyphenyl)piperazine-1-carboxamido)methyl)benzoate hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; Stage #2: With water; sodium chloride In dichloromethane	99.9%

oxetan-3-one (6704-31-0) + methyl 3-fluoro-4-((N-(3-fluorophenyl)piperazine-1-carboxamido)methyl)benzoate hydrochloride → methyl 3-fluoro-4-((N-(3-fluorophenyl)-4-(oxetan-3-yl)piperazine-1-carboxamido)methyl)benzoate

Conditions	Yield
Stage #1: oxetan-3-one; methyl 3-fluoro-4-((N-(3-fluorophenyl)piperazine-1-carboxamido)methyl)benzoate hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; Stage #2: With water; sodium chloride In dichloromethane	99.8%

oxetan-3-one (6704-31-0) + methyl 6-((N-(3-fluorophenyl)piperazine-1-carboxamido)methyl)nicotinate hydrochloride → methyl 6-((N-(3-fluorophenyl)-4-(oxetan-3-yl)piperazine-1-carboxamido)methyl)nicotinate

Conditions	Yield
Stage #1: oxetan-3-one; methyl 6-((N-(3-fluorophenyl)piperazine-1-carboxamido)methyl)nicotinate hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; Stage #2: With water; sodium chloride In dichloromethane	99.8%

oxetan-3-one (6704-31-0) + methyl 3-fluoro-4-((N-(4-fluorophenyl)piperazine-1-carboxamido)methyl)benzoate hydrochloride → methyl 3-fluoro-4-((N-(4-fluorophenyl)-4-(oxetan-3-yl)piperazine-1-carboxamido)methyl)benzoate

Conditions	Yield
Stage #1: oxetan-3-one; methyl 3-fluoro-4-((N-(4-fluorophenyl)piperazine-1-carboxamido)methyl)benzoate hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; Stage #2: With water; sodium chloride In dichloromethane	99.8%

oxetan-3-one (6704-31-0) + methyl 6-((N-(4-chlorophenyl)piperazine-1-carboxamido)methyl)nicotinate hydrochloride → methyl 6-((N-(4-chlorophenyl)-4-(oxetan-3-yl)piperazine-1-carboxamido)methyl)nicotinate

Conditions	Yield
Stage #1: oxetan-3-one; methyl 6-((N-(4-chlorophenyl)piperazine-1-carboxamido)methyl)nicotinate hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; Stage #2: With water; sodium chloride In dichloromethane	99.8%

oxetan-3-one (6704-31-0) + methyl 6-((N-(3-methoxyphenyl)piperazine-1-carboxamido)methyl)nicotinate hydrochloride → methyl 6-((N-(3-methoxyphenyl)-4-(oxetan-3-yl)piperazine-1-carboxamido)methyl)nicotinate

Conditions	Yield
Stage #1: oxetan-3-one; methyl 6-((N-(3-methoxyphenyl)piperazine-1-carboxamido)methyl)nicotinate hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; Stage #2: With water; sodium chloride In dichloromethane	99.7%

oxetan-3-one (6704-31-0) + methyl 3-fluoro-4-((N-(4-methoxyphenyl)piperazine-1-carboxamido)methyl)benzoate hydrochloride → methyl 3-fluoro-4-((N-(4-methoxyphenyl)-4-(oxetan-3-yl)piperazine-1-carboxamido)methyl)benzoate

Conditions	Yield
Stage #1: oxetan-3-one; methyl 3-fluoro-4-((N-(4-methoxyphenyl)piperazine-1-carboxamido)methyl)benzoate hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; Stage #2: With water; sodium chloride In dichloromethane	99.7%

oxetan-3-one (6704-31-0) + methyl 6-((N-(4-methoxyphenyl)piperazine-1-carboxamido)methyl)nicotinate hydrochloride → methyl 6-((N-(4-methoxyphenyl)-4-(oxetan-3-yl)piperazine-1-carboxamido)methyl)nicotinate

Conditions	Yield
Stage #1: oxetan-3-one; methyl 6-((N-(4-methoxyphenyl)piperazine-1-carboxamido)methyl)nicotinate hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; Stage #2: With water; sodium chloride In dichloromethane	99.7%

oxetan-3-one (6704-31-0) + methyl 6-((N-(3-chlorophenyl)piperazine-1-carboxamido)methyl)nicotinate hydrochloride → methyl 6-((N-(3-chlorophenyl)-4-(oxetan-3-yl)piperazine-1-carboxamido)methyl)nicotinate

Conditions	Yield
Stage #1: oxetan-3-one; methyl 6-((N-(3-chlorophenyl)piperazine-1-carboxamido)methyl)nicotinate hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; Stage #2: With water; sodium chloride In dichloromethane	99.6%

oxetan-3-one (6704-31-0) + methyl 4-((N-(3-chlorophenyl)piperazine-1-carboxamido)methyl)benzoate hydrochloride → methyl 4-((N-(3-chlorophenyl)-4-(oxetan-3-yl)piperazine-1-carboxamido)methyl)benzoate

Conditions	Yield
Stage #1: oxetan-3-one; methyl 4-((N-(3-chlorophenyl)piperazine-1-carboxamido)methyl)benzoate hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; Stage #2: With water; sodium chloride In dichloromethane	99.4%

oxetan-3-one (6704-31-0) + 2-(Ethylamino)ethanol (110-73-6) → 8-ethyl-2,5-dioxa-8-azaspiro[3.4]octane

Conditions	Yield
With acetic acid In dichloromethane at 20℃; Molecular sieve; Inert atmosphere;	99%

oxetan-3-one (6704-31-0) + 2-((4-bromobenzyl)amino)ethanol → 8-(4-bromobenzyl)-2,5-dioxa-8-azaspiro[3.4]octane

Conditions	Yield
With indium(III) triflate In dichloromethane at 20℃; Molecular sieve; Inert atmosphere;	99%

oxetan-3-one (6704-31-0) + tert-butyl 4-(2,6-dichloropyridin-4-yl)piperidine-1-carboxylate → 2,6-dichloro-4-[1-(oxetan-3-yl)piperidin-4-yl]pyridine

Conditions	Yield
Stage #1: tert-butyl 4-(2,6-dichloropyridin-4-yl)piperidine-1-carboxylate With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 1h; Stage #2: oxetan-3-one With triethylamine In tetrahydrofuran for 0.5h; Stage #3: With sodium tris(acetoxy)borohydride In tetrahydrofuran for 2h;	99%

oxetan-3-one (6704-31-0) + C26H37FN4O4 → C29H41FN4O5

Conditions	Yield
Stage #1: oxetan-3-one; C26H37FN4O4 With acetic acid In dichloromethane at 15 - 25℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 15 - 25℃;	99%

oxetan-3-one (6704-31-0) + 1-triphenylphosphoranylidene-2-propanone (1439-36-7) → 2-methyl-4-hydroxymethylfuran (20416-19-7)

Conditions	Yield
Stage #1: oxetan-3-one; 1-triphenylphosphoranylidene-2-propanone In dichloromethane at 20℃; for 16h; Inert atmosphere; Stage #2: With hydrogenchloride In water for 0.166667h; Inert atmosphere;	99%

oxetan-3-one (6704-31-0) + (Benzoylmethylene)triphenylphosphorane (20913-05-7) → 2-(oxetan-3-ylidene)-1-phenylethan-1-one

Conditions	Yield
In dichloromethane at 20℃; for 16h; Inert atmosphere;	99%
In dichloromethane Inert atmosphere;

oxetan-3-one (6704-31-0) + 1-Phenyl-2-(trimethylsilyl)acetylene (2170-06-1) → 5-phenyl-4-(trimethylsilyl)-2H-pyran-3(6H)-one (1379664-49-9)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); triphenylphosphine In 1,4-dioxane at 90℃; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere; Sealed tube; regioselective reaction;	99%

oxetan-3-one (6704-31-0) + 3-[(tert-butyldimethylsilyl)oxy]aniline (121942-75-4) → N-(3-((tert-butyldimethylsilyl)oxy)phenyl)oxetan-3-amine

Conditions	Yield
Stage #1: oxetan-3-one; 3-[(tert-butyldimethylsilyl)oxy]aniline With acetic acid In methanol at 20℃; for 1h; Stage #2: With sodium cyanoborohydride In methanol at 0℃; for 3h;	99%

oxetan-3-one (6704-31-0) + 1-Bromonaphthalene (90-11-9) → 3-(naphthalen-1-yl)oxetan-3-ol

Conditions	Yield
Stage #1: 1-Bromonaphthalene With n-butyllithium In diethyl ether at 0℃; for 0.166667h; Stage #2: oxetan-3-one In diethyl ether at 0 - 20℃; for 1h;	99%

oxetan-3-one (6704-31-0) + methyl 6-((N-(3-chloro-4-fluorophenyl)piperazine-1-sulfonamido)methyl)nicotinate hydrochloride → methyl 6-(((N-(3-chloro-4-fluorophenyl)-4-(oxetan-3-yl)piperazine)-1-sulfonamido)methyl)nicotinate

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h;	98.6%
With sodium tris(acetoxy)borohydride In dichloromethane for 18h;	98.6%

Upstream product

• 107-19-7 propargyl alcohol 
• 7748-36-9 oxetan-3-ol 
• 922500-97-8 3,3-dimethoxyoxetane 
• 186581-53-3 diazomethane 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 1123787-70-1 3-(2-(benzyloxy)phenyl)oxetan-3-ol 
• 1123787-67-6 2-(oxetane-3-ylidene)acetonitrile 
• 693247-54-0 C₂₁H₂₆F₆N₂O₂ 
• 1221819-48-2 1-[1-(4-chlorophenyl)cyclobutyl]-2-(oxetan-3-ylidene)ethanone 
• 922500-95-6 3-(nitromethylene)oxetane 
• 1221819-46-0 3-((phenylsulfonyl)methylene)oxetane 
• 1021393-00-9 3-(dibenzylamino)oxetane-3-carbonitrile 
• 1395416-51-9 oxetan-3-yl-(4-o-tolyl-pyridin-3-yl)-amine 
• 1430471-82-1 4-(4-bromo-2-methoxyphenoxy)-1-(oxetan-3-yl)piperidine 
• 1430471-95-6 4-(4-iodophenoxy)-1-(oxetan-3-yl)piperidine 
• 1439367-59-5 3-(4-phenylbutyl)-oxetan-3-ol 
• 1579298-13-7 3-(1-phenylvinyl)oxetan-3-ol 
• 1579298-14-8 3-(1-(m-tolyl)vinyl)oxetan-3-ol 
• 1579298-15-9 3-(1-(p-tolyl)vinyl)oxetan-3-ol 

Relevant articles and documents

Synthesis method of 3-oxetanone

The invention discloses a synthesis method of 3-oxetanone. Specifically, 1, 3-dichloroacetone and ethylene glycol are taken as raw materials, 3-oxetanone is synthesized at high yield through three steps of carbonyl protection reaction, ring closing reaction and deprotection reaction. The preparation method of 3-oxetanone is a synthesis method which is high in yield, low in cost, environment-friendly, easy to operate and suitable for industrialization.

3-oxetanone synthesis method

The invention provides a 3-oxetanone synthesis method, which comprises: removing the protection group from an intermediate in an organic solvent I by using an organic strong acid, neutralizing with aweak alkali to achieve an alkaline pH value, carrying out concentration distillation on the solvent to obtain a oxetan-3-ol crude product, oxidizing the oxetan-3-ol with an oxidizing agent in the presence of a catalyst I, a halide and an alkali, and carrying out separating purification to obtain the 3-oxetanone product, wherein the intermediate preparation method comprises: carrying out a ring opening reaction by using epichlorohydrin and glacial acetic acid as raw materials under the catalysis of a catalyst II, adding ethyl vinyl ether under an organic strong acid condition, carrying out a protection group forming reaction, and carrying out a ring formation reaction under a strong alkali condition so as to obtain the key intermediate solution. According to the present invention, the oxetan-3-ol preparation process is combined without the purifying of oxetan-3-ol so as to eliminate the oxetan-3-ol purifying step; and the method has characteristics of inexpensive raw materials, short route, no use of dangerous reagents and the like.

A β-Carbon elimination strategy for convenient: In situ access to cyclopentadienyl metal complexes

The electronic and steric properties of tailored cyclopentadienyl (Cp) ligands are powerful handles to modulate the catalytic properties of their metal complexes. This requires the individual preparation, purification and storage of each ligand/metal combination. Alternative, ideally in situ, complexation protocols would be of high utility. We disclose a new approach to access Cp metal complexes. Common metal precursors rapidly react with cyclopentadienyl carbinols via β-carbon eliminations to directly give the Cp-metal complexes. An advantage of this is the direct and flexible use of storable pre-ligands. No auxiliary base is required and the Cp complexes can be prepared in situ in the reaction vessel for subsequent catalytic transformations.