15506-53-3

Usage

Uses

Used in Chemical Synthesis:
Cyclobutane-1,3-dione is used as a synthetic intermediate for the preparation of various organic compounds. Its diketone structure allows it to participate in a range of chemical reactions, making it a valuable building block in the synthesis of complex molecules.
Used in Pharmaceutical Industry:
Cyclobutane-1,3-dione is used as a key component in the development of pharmaceutical compounds. Its unique structure and reactivity can be exploited to create new drugs with potential therapeutic applications.
Used in Material Science:
Cyclobutane-1,3-dione is used as a precursor in the synthesis of advanced materials, such as polymers and composites, with specific properties tailored for various applications in material science.
Used in Research and Development:
Cyclobutane-1,3-dione is used as a research compound for studying the properties and reactivity of diketones. Its limited availability and unique structure make it an interesting subject for academic and industrial research, potentially leading to new discoveries and applications.

InChI:InChI=1/C4H4O2/c5-3-1-4(6)2-3/h1-2H2

Synthetic route

3-t-Butoxycyclobutenone (101901-49-9) → cyclobutane-1,3-dione (15506-53-3)

Conditions	Yield
With trifluoroacetic acid at -10 - 15℃; for 3h;	88%

Ketene (463-51-4) + diethyl ether (60-29-7) → cyclobutane-1,3-dione (15506-53-3)

Conditions	Yield
beim Stehen;

triethylamine (121-44-8) + bromoacetaldehyde (17157-48-1) → cyclobutane-1,3-dione (15506-53-3)

Conditions	Yield
at 130 - 135℃;

3-ethoxy-2-cyclobuten-1-one (4683-54-9) → cyclobutane-1,3-dione (15506-53-3)

Conditions	Yield
With hydrogenchloride

1-ethoxy-cyclobuten-(1)-one-(3) → cyclobutane-1,3-dione (15506-53-3)

Conditions	Yield
With sulfuric acid

1,1,3,3-tetramethoxycyclobutane (152897-19-3) → cyclobutane-1,3-dione (15506-53-3)

Conditions	Yield
In water formic acid; ethyl acetate

2-[4-(4-trifluoromethylphenoxy)phenoxy]propionic acid fluoride + thallium salt of cyclobutane-1,3-dione → 2-[[2-[4-(4-trifluoromethylphenoxy)phenoxy]propionyl]]cyclobutane-1,3-dione + cyclobutane-1,3-dione (15506-53-3)

cyclobutane-1,3-dione (15506-53-3) + N-cyclohexyl-cyclohexanamine (101-83-7) → cyclobutane-1,2-dione (33689-28-0)

Conditions	Yield
In ethyl acetate	96.7%

cyclobutane-1,3-dione (15506-53-3) → 2-cyclobuten-1-one (32264-87-2)

Conditions	Yield
With chlorine In tetrachloromethane	90%

2-hydroxy-3-butene (598-32-3) + cyclobutane-1,3-dione (15506-53-3) → 1-methylprop-2-enyl 3-oxobutanoate (25456-01-3)

Conditions	Yield
With dmap In diethyl ether for 15h; Ambient temperature;	87%

N,N-dimethyl-cyclohexanamine (98-94-2) + cyclobutane-1,3-dione (15506-53-3) → cyclobutane-1,2-dione (33689-28-0)

Conditions	Yield
In ethyl acetate	83.3%

diazomethane (186581-53-3, 908094-01-9) + cyclobutane-1,3-dione (15506-53-3) → 3-methoxy-2-cyclobuten-1-one (127230-97-1)

Conditions	Yield
In diethyl ether; dichloromethane at 0℃; for 2h;	82%

(1-hydroxy-allyl)-phosphonic acid dimethyl ester (6329-53-9) + cyclobutane-1,3-dione (15506-53-3) → dimethyl [1-(2-ketobutanoyloxy)-2-propenyl]phosphonate

Conditions	Yield
With dmap In tetrahydrofuran; dichloromethane at -20 - 20℃;	82%

cyclobutane-1,3-dione (15506-53-3) + dicyclohexylmethylamine (19293-63-1) → cyclobutane-1,2-dione (33689-28-0)

Conditions	Yield
In ethyl acetate	81.4%

cyclobutane-1,3-dione (15506-53-3) + diethylamine (109-89-7) → cyclobutane-1,2-dione (33689-28-0)

Conditions	Yield
In ethyl acetate	79.2%

cyclobutane-1,3-dione (15506-53-3) + dimethyl amine (124-40-3) → 3-Dimethylamino-cyclobut-2-enone (171085-81-7)

Conditions	Yield
In tetrahydrofuran; dichloromethane at 0℃; for 2h;	74%

cyclobutane-1,3-dione (15506-53-3) + (E)-5-iodo-4-methyl-1-(t-butyldimethylsiloxy)-4-penten-2-ol (125214-80-4) → (E)-1-iodo-2-methyl-5-(t-butyldimethylsiloxy)-1-penten-4-yl 3-oxo-1-butanoate (125215-04-5)

Conditions	Yield
With dmap In diethyl ether at -23℃; for 16h;	71%

cyclobutane-1,3-dione (15506-53-3) + sodium ethanolate (141-52-6) → cyclobutane-1,2-dione (33689-28-0)

Conditions	Yield
With sodium In ethanol; acetonitrile	69%

isoleucine (319-78-8, 443-79-8, 1509-34-8, 1509-35-9, 3107-04-8, 7004-09-3, 73-32-5) + cyclobutane-1,3-dione (15506-53-3) → 5-(1-methylpropyl)-2,4-pyrrolidinedione

Conditions	Yield
Stage #1: isoleucine With hydrogenchloride; ethanol Heating / reflux; Stage #2: With sodium ethanolate In ethanol for 0.5h; Stage #3: cyclobutane-1,3-dione With sulfuric acid; sodium ethanolate more than 3 stages;	55.6%
Stage #1: isoleucine With hydrogenchloride In ethanol Heating / reflux; Stage #2: With sodium ethanolate In ethanol for 0.5h; Stage #3: cyclobutane-1,3-dione With sulfuric acid; water; sodium ethanolate more than 3 stages;	55.6%

cyclobutane-1,3-dione (15506-53-3) + DL-isovaline (595-39-1) → C9H13NO3

Conditions	Yield
Stage #1: DL-isovaline With hydrogenchloride; ethanol Heating / reflux; Stage #2: With sodium ethanolate In ethanol for 0.5h; Stage #3: cyclobutane-1,3-dione With sulfuric acid; sodium ethanolate more than 3 stages;	53%

cyclobutane-1,3-dione (15506-53-3) → cyclobutane-1,2-dione (33689-28-0)

Conditions	Yield
With ammonia In acetonitrile	47%

2-amino-3-cyanohexanoic acid + cyclobutane-1,3-dione (15506-53-3) → C11H14N2O3

Conditions	Yield
Stage #1: 2-amino-3-cyanohexanoic acid With hydrogenchloride; ethanol Heating / reflux; Stage #2: With sodium ethanolate In ethanol for 0.5h; Stage #3: cyclobutane-1,3-dione With sulfuric acid; sodium ethanolate more than 3 stages;	45%

acetoacetamido (5977-14-0) + cyclobutane-1,3-dione (15506-53-3) → 4-amino-2,4-dimethyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid amide (15846-31-8)

Conditions	Yield
With diethyl ether; ammonia at -15 - -10℃; Man erhitzt das entstandene gelbe Oel im Wasserstoffstrom auf 110grad;

ethanol (64-17-5) + cyclobutane-1,3-dione (15506-53-3) → ethyl acetoacetate (141-97-9)

Conditions	Yield
With sodium ethanolate
With sulfuric acid

cyclobutane-1,3-dione (15506-53-3) + semicarbazide hydrochloride (563-41-7) → 1-(3-semicarbazono-butyryl)-semicarbazide (30540-13-7)

Conditions	Yield
With sodium acetate

cyclobutane-1,3-dione (15506-53-3) → 4-bromo-3-oxobutyric acid bromide (52148-44-4)

Conditions	Yield
With tetrachloromethane; bromine

cyclobutane-1,3-dione (15506-53-3) → acetoacetamido (5977-14-0)

Conditions	Yield
With ammonia at -15 - -10℃;

cyclobutane-1,3-dione (15506-53-3) → 2-acetoacetic acid (541-50-4)

Conditions	Yield
With water

cyclobutane-1,3-dione (15506-53-3) → butyraldehyde (123-72-8)

Conditions	Yield
With hydrogen; platinum

cyclobutane-1,3-dione (15506-53-3) → acetoacetic acid methyl ester (105-45-3)

Conditions	Yield
With methanol; sodium methylate

cyclobutane-1,3-dione (15506-53-3) → Dehydracetic acid (520-45-6)

cyclobutane-1,3-dione (15506-53-3) + aniline (62-53-3) → N-phenylacetoacetamide (102-01-2)

cyclobutane-1,3-dione (15506-53-3) + phenylhydrazine (100-63-0) → 3-phenylhydrazono-butyric acid-(N'-phenyl-hydrazide) (67790-05-0)

Conditions	Yield
With benzene

Upstream product

• 463-51-4 Ketene 
• 60-29-7 diethyl ether 
• 121-44-8 triethylamine 
• 17157-48-1 bromoacetaldehyde 
• 4683-54-9 3-ethoxy-2-cyclobuten-1-one 
• 101901-49-9 3-t-Butoxycyclobutenone 
• 152897-19-3 1,1,3,3-tetramethoxycyclobutane 

Downstream Products

• 15846-31-8 4-amino-2,4-dimethyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid amide 
• 141-97-9 ethyl acetoacetate 
• 67790-05-0 3-phenylhydrazono-butyric acid-(N'-phenyl-hydrazide) 
• 38425-52-4 3-Acetoxycyclobutenon 
• 136003-07-1 3-Oxo-butyric acid (1S,2R,3S,5R)-6,6-dimethyl-2-phenyl-bicyclo[3.1.1]hept-3-yl ester 
• 136003-12-8 3-Oxo-butyric acid (1S,2R,3S,5R)-6,6-dimethyl-2-[1,1';3',1'']terphenyl-5'-yl-bicyclo[3.1.1]hept-3-yl ester 
• 41659-16-9 2-(2,3-Diphenyl-cycloprop-2-enylidene)-cyclobutane-1,3-dione 
• 152897-19-3 1,1,3,3-tetramethoxycyclobutane 
• 33689-28-0 cyclobutane-1,2-dione 
• 32264-87-2 2-cyclobuten-1-one 
• 38425-50-2 3-(Methylphenylamino)-2-cyclobuten-1-on 
• 38425-49-9 3-Phenylaminocyclobutenon 
• 38425-53-5 Benzoic acid 3-oxo-cyclobut-1-enyl ester 
• 102-01-2 N-phenylacetoacetamide 

Relevant academic research and scientific papers

Expedient Synthesis of 1,3-Cyclobutanedione via Thermal Dimerization of t-Butoxyethyne

A new, short, and efficient synthesis of 1,3-cyclobutandione consists of the thermal conversion of 1-butoxyethyne into 3-t-butoxycyclobutenone (the first example of cyclobutenone formation from an unsubstituted acetylenic monoether) followed by cleavage of the t-butyl group with trifluoroacetic acid.The 62percent overall yield is much higher than that of the previously described procedure.

1,3-cyclobutanedione-bisketals, process for their production and their use

Bisketals of 1,3-cyclobutanedione with monovalent and divalent alcohols as well as processes for their production from 1,3-cyclobutanedione or from 3-acetoxy-2-cyclobuten-1-one contained in the distillation residues of the diketene production. The bisketals are suitable intermediate products for the production of squaric acid, for the production and/or purification of 1,3-cyclobutanedione, or as a stable form for storage or substitute for this unstable dione.

Process for the production of squaric acid

A process for the production of squaric acid by halogenation either of pure 3-acetoxy-2-cyclobuten-1-one or of a distillation residue of diketene production containing 3-acetoxy-2-cyclobuten-1-one to a cyclobutenone of formula: STR1 and then hydrolysis of these cyclobutenones to squaric acid. The halogenated cyclobutenones are intermediate products in the process.

3-hydroxy-2-cyclobuten-1-one salts, their production and use

3-Hydroxy-2-cyclobuten-1-one salts of the general formula: STR1 wherein R is an ammonium group of the general formula: STR2 wherein R1, R2 and R3 are the same or different in meaning and each is a hydrogen atom, a lower alkyl group or a cycloalkyl group or R is an alkali metal atom. The salts according for formula I are obtained by the reaction of pure 3-acetoxy-2-cyclobuten-1-one, or 1,3-cyclobutanedione or a distillation residue of the diketene production containing 3-acetoxy-2-cyclobuten-1-one, with a base. The base can be an amine of the general formula: STR3 wherein R1, R2, and R3 have the above-mentioned meaning, or an alkali metal alcoholate or an alkali metal hydroxide. The salts according to formula I are suitable for the production of squaric acid, by their being halogenated in a first step and then being hydrolyzed to squaric acid in a second step.

Substituted cycloalkanediones

Novel substituted cycloalkanediones and their use for the control of weeds.