4415-87-6

Basic information

• Product Name: Cyclobutane-1,2,3,4-tetracarboxylic dianhydride
• Synonyms: 3a,3b,6a,6b-Tetrahydrocyclobuta[1,2-c:3,4-c']difuran-1,3,4,6-tetrone;4,9-Dioxatricyclo[5.3.0.02,6]decane-3,5,8,10-tetrone;Cyclobutane 1,2,3,4-tetracarboxylic acid 1,2:3,4-dianhydride;Cyclobutane-1,2,3,4-tetracarboxylic dianhydride ,98%;Cyclobutane-1,2,3,4-tetracarboxylic acid dianhydride;Cyclobutane-1,2,3,4-tetracarboxylic acid dianhydride (CBDA);Cyclobutane-1,2,3,4-tetracarboxylic;Cyclobuta[1,2-c:3,4-c']difuran-1,3,4,6(3aH,3bH,6aH,6bH)-tetraone
• CAS NO: 4415-87-6
• Molecular Formula: C₈H₄O₆
• Molecular Weight: 196.11
• EINECS: 224-577-5
• Product Categories: fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, Organic Building Blocks;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, pharmaceutical intermediates;Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research;Carbonyl Compounds;Carboxylic Acid Anhydrides;Organic Building Blocks
• Mol File: 4415-87-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 545.3 °C at 760 mmHg
• Flash Point: 253.7 °C
• Appearance: /
• Density: 1.823 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in Toluene
• BRN: 1430553
• CAS DataBase Reference: Cyclobutane-1,2,3,4-tetracarboxylic dianhydride(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclobutane-1,2,3,4-tetracarboxylic dianhydride(4415-87-6)
• EPA Substance Registry System: Cyclobutane-1,2,3,4-tetracarboxylic dianhydride(4415-87-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 1759
• WGK Germany: 3
• F: 9-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 4415-87-6(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow solid

Uses

Different sources of media describe the Uses of 4415-87-6 differently. You can refer to the following data:
1. cyclobutane-1,2,3,4-tetracarboxylic dianhydride and diamine monomer are used for preparation a polyimide (PI), the type of polyimide has excellent electrical characteristics and optical type, with the material prepared the PI film, in addition to having a higher rate cast visible outside, and can withstand high temperatures thirty-four Baidu. Its performance is very good, is the preparation of a liquid crystal display with an ideal material for the film.
2. Reactant for:Preparation of biologically and pharmacologically active moleculesPreparation of photosensitive polyimide material for high performance organic thin-film transistorsSelective crosslinking of polyimide for photonic devices

Preparation

Preparation of 1,2,3,4- cyclobutanetetracarboxylic acid dianhydride (CBDA)To a 2L quartz glass photoreactor equipped with sixteen UV lamps (300nm) , a stirrer and a cooler were attached and 250ml of ethyl acetate and 100g of maleic anhydride were added thereto followed by stirring for complete mixing. To avoid an excessive temperature increase, an air-cooling type cooler was first run and then UV light was illuminated for a photoreaction for 24h?with stirring so as not to have the reactants adhered to the reactor walls. As a result, 71g of white solid was obtained. After the filtration, the white solid was dried for 24h?in a vacuum dryer at 60°C Thus-obtained solid was then added to acetic anhydride, dissolved therein and slowly heated to 150°C followed by the reaction for 24h . Hot reaction solution was filtered through a filter paper to remove impurities and kept in a freezer at the temperature of 0°C or less for recrystallization for 24h?to obtain a yellow solid. Thus-obtained solid was filtered and washed three times with 1,4-dioxane to remove acetic anhydride, and then dried in a vacuum oven at 60°C?for 48h?to obtain 64g of 1, 2, 3, 4 -cyclobutane tetracarboxylic acid dianhydride (CBDA) .

Synthetic route

1,2,3,4-cyclobutane tetracarboxylic acid (53159-92-5) → cyclobutanetetracarboxylic dianhydride (4415-87-6)

Conditions	Yield
With acetic anhydride at 150℃; for 24h;

maleic anhydride (108-31-6) → cyclobutanetetracarboxylic dianhydride (4415-87-6)

Conditions	Yield
Stage #1: maleic anhydride In ethyl acetate for 240h; UV-irradiation; Stage #2: With acetic anhydride at 150℃; for 24h;
In ethyl acetate for 2h; Inert atmosphere; Slug flow microreactor; Ultrasonication; Irradiation;	2.15 g

maleic anhydride (108-31-6) + ethene (74-85-1) → cyclobutanetetracarboxylic dianhydride (4415-87-6) + cis-1,2-cyclobutane dicarboxylic anhydride (4462-96-8)

Conditions	Yield
With benzophenone In ethyl acetate at 25℃; under 760.051 Torr; UV-irradiation; Flow reactor;

rhodamine B ethylenediamine (950846-89-6) + cyclobutanetetracarboxylic dianhydride (4415-87-6) → C68H76N8O10

Conditions	Yield
In acetonitrile at 50℃; for 24h; Solvent; Temperature;	87%

cyclobutanetetracarboxylic dianhydride (4415-87-6) + 2,5-Dimethyl-1,4-phenylenediamine (6393-01-7) → 2,5-bis(4-amino-2,5-dimethylphenyl)tetrahydrocyclobuta[1,2-c:3,4-c′]dipyrrole-1,3,4,6(2H,5H)tetraone

Conditions	Yield
Stage #1: cyclobutanetetracarboxylic dianhydride; 2,5-Dimethyl-1,4-phenylenediamine In 1-methyl-pyrrolidin-2-one at 20℃; for 12h; Inert atmosphere; Stage #2: In 1-methyl-pyrrolidin-2-one; toluene at 180℃; for 9h; Inert atmosphere;	80.8%

cyclobutanetetracarboxylic dianhydride (4415-87-6) + C27H32BNO → C62H64B2N2O6

Conditions	Yield
With propionic acid at 100 - 120℃; for 24h; Inert atmosphere;	77%

concentrated hydrofluoric acid + cyclobutanetetracarboxylic dianhydride (4415-87-6) + N-(2-tert-Butyldimethylsiloxy)ethyl-N-(4-phenoxy)benzylamine + diazomethyl-trimethyl-silane (18107-18-1) → (1α,2β,3β,4α)-1,3-Di[N-(2-hydroxyethyl)-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid (171349-30-7)

Conditions	Yield
With hydrogenchloride; dmap; LiOH; triethylamine In acetic acid 1-hydroxy-propyl ester; methanol; water; acetonitrile	40%

cyclobutanetetracarboxylic dianhydride (4415-87-6) + N-Benzyl-N-(4-phenoxybenzyl)amine (169943-97-9) → (1α,2β,3β,4α)-1,3-Di(N-benzyl-N-(4-phenoxybenzyl)aminocarbonyl)cyclobutane-2,4-dicarboxylic acid (171348-76-8)

Conditions	Yield
In tetrahydrofuran; ethyl acetate	32%

cyclobutanetetracarboxylic dianhydride (4415-87-6) + aqueous H2 SO4 + N-Propyl-N-(4-phenoxymethylbenzyl)amine hydrochloride (169943-70-8) + triethylamine (121-44-8) → (1α,2β,3β,4α)-1,3-Di[N-propyl-N-(4-phenoxymethylbenzyl)aminocarbonyl]-2,4-cyclobutanedicarboxylic acid (171349-23-8)

Conditions	Yield
In acetonitrile	28%

cyclobutanetetracarboxylic dianhydride (4415-87-6) + aqueous H2 SO4 + N-Propyl-N-(4-phenoxymethylbenzyl)amine hydrochloride (169943-70-8) + triethylamine (121-44-8) → 1,3-diacid + (1α,2β,3β,4α)-1,2-Di[N-propyl-N-[4-phenoxymethylbenzyl]aminocarbonyl]cyclobutane-3,4-dicarboxylic acid

Conditions	Yield
In acetonitrile	A 28% B n/a

cyclobutanetetracarboxylic dianhydride (4415-87-6) + dibenzylamine (103-49-1) → (1α,2β,3β,4α)-1,3-Di[N,N-dibenzylaminocarbonyl]cyclobutane-2,4-dicarboxylic acid (171348-93-9)

Conditions	Yield
In tetrahydrofuran; ethyl acetate	22%

cyclobutanetetracarboxylic dianhydride (4415-87-6) + dibenzylamine (103-49-1) → (1α,2β,3β,4α)-1,2-Di[N,N-dibenzylaminocarbonyl]cyclobutane-3,4-dicarboxylic acid

Conditions	Yield
In tetrahydrofuran; ethyl acetate	22%

cyclobutanetetracarboxylic dianhydride (4415-87-6) + N-Benzyl-N-(4-chlorobenzyl)amine Hydrochloride + triethylamine (121-44-8) → (1α,2β,3β,4α)-1,3-Di[N-benzyl-N-(4-chlorobenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid (171348-94-0)

Conditions	Yield
In ethyl acetate; N,N-dimethyl-formamide	21%

cyclobutanetetracarboxylic dianhydride (4415-87-6) + N-Benzyl-N-(4-chlorobenzyl)amine Hydrochloride + triethylamine (121-44-8) → (1α,2β,3β,4α)-1,2-Di(N-benzyl-N-(4-chlorobenzyl)aminocarbonyl)cyclobutane-3,4-dicarboxylic acid

Conditions	Yield
In ethyl acetate; N,N-dimethyl-formamide	21%

cyclobutanetetracarboxylic dianhydride (4415-87-6) + triethylamine (121-44-8) + 4-(4-phenoxyphenyl)-1,2,3,6-tetrahydropyridine (171350-05-3) → (1α,2β,3β,4α)-1,3-Di[4-(4-phenoxyphenyl)-1,2,3,6-tetrahydropyridin-1-ylcarbonyl]cyclobutane-2,4-dicarboxylic acid (171349-46-5)

Conditions	Yield
In ethyl acetate; acetonitrile	18%

N-(3,4-dichlorobenzyl)-N-(4-phenoxybenzyl)amine (171350-08-6) + cyclobutanetetracarboxylic dianhydride (4415-87-6) → (1α,2β,3β,4α)-1,3-Di[N-(3,4-Dichlorobenzyl)-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid (171349-58-9)

Conditions	Yield
In ethyl acetate; acetonitrile	12%

cyclobutanetetracarboxylic dianhydride (4415-87-6) + N-cinnamylbenzylamine (40032-55-1) → (1α,2β,3β,4α)-1-[N-Benzyl-N-(trans-3-phenyl-2-propenyl)aminocarbonyl]cyclobutane-2,3,4-tricarboxylic acid

Conditions	Yield
In methanol; ethyl acetate; acetonitrile	12%

cyclobutanetetracarboxylic dianhydride (4415-87-6) + N-Benzyl-N-(4-phenoxybenzyl)amine (169943-97-9) → (1α,2β,3β,4α)-1,2-Di[N-benzyl-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-3,4-dicarboxylic acid

Conditions	Yield
In tetrahydrofuran; ethyl acetate	6%

cyclobutanetetracarboxylic dianhydride (4415-87-6) + N-(S)-α-methylbenzyl-N-(4-phenoxybenzyl)amine (169944-01-8) + triethylamine (121-44-8) → (1α,2β,3β,4α)-1,3-Di[N-(S)-α-Methylbenzyl-N-(4-phenoxybenzyl)-aminocarbonyl]cyclobutane-2,4-dicarboxylic acid (171349-42-1)

Conditions	Yield
In ethyl acetate; acetonitrile	4%

cyclobutanetetracarboxylic dianhydride (4415-87-6) + 2,5-bis(N-trimethylsilylaminomethyl)bicyclo[2.2.1]heptane + 2,6-bis(N-trimethylsilylaminomethyl)bicyclo[2.2.1]heptane → poly[2,4-trimethylsilyl-N-(5(6)-methylenebicyclo[2.2.1]heptane-2-ylmethyl)cyclobutanetetracarboxylic acid 1,3-diamide]

Conditions	Yield
With N-methyl-2-pyrrolidie at 20℃; for 3h; Polymerization;

cyclobutanetetracarboxylic dianhydride (4415-87-6) + N-trimethylsilyl-(3,5,5-trimethyl-3-trimethylsilylaminomethylcyclohexylamine) (85213-49-6) → poly[2,4-trimethylsilyl-N-(5-amino-1,3,3-trimethylcyclohexanemethyl)cyclobutanetetracarboxylic acid 1,3-diamide]

Conditions	Yield
With N-methyl-2-pyrrolidie at 20℃; for 3h; Polymerization;

cyclobutanetetracarboxylic dianhydride (4415-87-6) + N-trimethylsilyl-(3,5,5-trimethyl-3-trimethylsilylaminomethylcyclohexylamine) (85213-49-6) → poly(amic acid trimethylsilyl ester); monomer(s): 1,2,3,4-cyclobutanetetracarboxylic dianhydride; N-trimethylsilyl-(3,5,5-trimethyl-3-trimethylsilylaminomethylcyclohexylamine)

Conditions	Yield
In N,N-dimethyl acetamide at 25℃; for 1h;

cyclobutanetetracarboxylic dianhydride (4415-87-6) + N-tert-butyldimethylsilyl-(3,5,5-trimethyl-3-tert-butyldimethylsilylaminomethylcyclohexylamine) (410090-46-9) → poly(amic acid tert-butyldimethylsilyl ester); monomer(s): 1,2,3,4-cyclobutanetetracarboxylic dianhydride; N-tert-butyldimethylsilyl-(3,5,5-trimethyl-3-tert-butyldimethylsilylaminomethylcyclohexylamine)

Conditions	Yield
In N,N-dimethyl acetamide at 25℃; for 1h;

cyclobutanetetracarboxylic dianhydride (4415-87-6) + 4,4'-methylenebis(N,N'-tert-butyldimethylsilylcyclohexylamine) (410090-47-0) → poly(amic acid tert-butyldimethylsilyl ester); monomer(s): 1,2,3,4-cyclobutanetetracarboxylic dianhydride; 4,4\-methylenebis(N,N\-tert-butyldimethylsilylcyclohexylamine)

Conditions	Yield
In N,N-dimethyl acetamide at 25℃; for 1h;

cyclobutanetetracarboxylic dianhydride (4415-87-6) → N,N'-dihydroxycyclobutanetetracarboxylic diimide (245049-70-1)

Conditions	Yield
With pyridine; hydroxylamine hydrochloride at 20 - 90℃; for 0.25h;

N-(4-Phenoxybenzyl)-N-(3-methoxyphenethyl)amine + cyclobutanetetracarboxylic dianhydride (4415-87-6) + acetonitrile (75-05-8) → [N-(4-phenoxybenzyl)-N-(3-methoxyphenethyl) aminocarbonyl]cyclobutane-2,4-dicarboxylic acid

Conditions	Yield
With triethylamine In ethyl acetate	0.59 g (35%)

N-(cyclopropylmethyl)-N-(4-phenoxybenzyl)amine (169943-53-7) + cyclobutanetetracarboxylic dianhydride (4415-87-6) → (1α,2β,3β,4α)-1,3-Di[N-cyclopropylmethyl-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid (171349-47-6)

Conditions	Yield
In acetonitrile	1.2 g (34%)

N-cyclobutyl-N-(4-phenoxybenzyl)amine + cyclobutanetetracarboxylic dianhydride (4415-87-6) → (1α,2β,3β,4α)-1,3-Di[N-cyclobutyl-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid (171349-53-4)

Conditions	Yield
In acetonitrile	2.3 g (33%)

N-cyclopentyl-N-(4-phenoxybenzyl)amine + cyclobutanetetracarboxylic dianhydride (4415-87-6) → (1α,2β,3β,4α)-1,3-Di[N-cyclopentyl-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid (171349-51-2)

Conditions	Yield
In acetonitrile	2.2 g (30%)

N-cyclohexyl-N-(4-phenoxybenzyl)amine + cyclobutanetetracarboxylic dianhydride (4415-87-6) → (1α,2β,3β,4α)-1,3-Di[N-cyclohexyl-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid (171349-52-3)

Conditions	Yield
In acetonitrile	2.9 g (38%)

N-(Cyclobutylmethyl)-N-(4-phenoxybenzyl)amine + cyclobutanetetracarboxylic dianhydride (4415-87-6) → (1α,2β,3β,4α)-1,3-Di[N-cyclobutylmethyl-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid (171349-54-5)

Conditions	Yield
In acetonitrile	100 mg (29%)

Upstream product

• 53159-92-5 1,2,3,4-cyclobutane tetracarboxylic acid 
• 108-31-6 maleic anhydride 
• 74-85-1 ethene 

Downstream Products

• 171349-23-8 (1α,2β,3β,4α)-1,3-Di[N-propyl-N-(4-phenoxymethylbenzyl)aminocarbonyl]-2,4-cyclobutanedicarboxylic acid 
• 171349-42-1 (1α,2β,3β,4α)-1,3-Di[N-(S)-α-Methylbenzyl-N-(4-phenoxybenzyl)-aminocarbonyl]cyclobutane-2,4-dicarboxylic acid 
• 171349-30-7 (1α,2β,3β,4α)-1,3-Di[N-(2-hydroxyethyl)-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid 
• 184488-02-6 (1S,2S,3S,4S)-3-Methoxycarbonyl-4-[N-{(2S,3R)-4-(3,4-dichlorophenyl)-3-(2-naphthoyloxy)-2-butyl}aminocarbonyl]-cyclobutane-1,2-dicarboxylic acid 
• 171349-27-2 (1α,2β,3β,4α)-1,3-Di[N-(2-benzylthioethyl)-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid 
• 171349-58-9 (1α,2β,3β,4α)-1,3-Di[N-(3,4-Dichlorobenzyl)-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid 
• 171349-26-1 (1α,2β,3β,4α)-1,3-Di[N-(2-ethylthioethyl)-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid 
• 171349-25-0 (1α,2β,3β,4α)-1,3-Di[N-(2-methylthioethyl)-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid 
• 171349-10-3 (1α,2β,3β,4α)-1,3-Di[N-propyl-N-(3-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid 
• 171348-99-5 (1α,2β,3β,4α)-1,3-Di[N-propyl-N-(4-phenoxybutyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid 
• 171349-48-7 (1α,2β,3β,4α)-1,3-Di[N-(4-fluorobenzyl)-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4dicarboxylic acid 
• 171349-54-5 (1α,2β,3β,4α)-1,3-Di[N-cyclobutylmethyl-N-(4-phenoxybenzyl)aminocarbonyl]cyclobutane-2,4-dicarboxylic acid 

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