21587-74-6

Usage

Uses

Used in Polymer Industry:
3,9-BIS(3-AMINOPROPYL)-2,4,8,10-TETRAOXASPIRO[5.5]UNDECANE is used as a crosslinking agent for enhancing the properties of polymers. Its spiro-orthoester structure and amino groups facilitate the formation of strong crosslinks, improving the mechanical strength, thermal stability, and chemical resistance of polymer materials.
Used in Material Synthesis:
3,9-BIS(3-AMINOPROPYL)-2,4,8,10-TETRAOXASPIRO[5.5]UNDECANE serves as a building block for the synthesis of new materials. The presence of reactive amino groups allows for the creation of functional materials such as gels, coatings, and adhesives with tailored properties for specific applications.
Used in Drug Delivery Systems:
3,9-BIS(3-AMINOPROPYL)-2,4,8,10-TETRAOXASPIRO[5.5]UNDECANE is under investigation for its potential use in drug delivery systems. The amino groups can be utilized for the conjugation of drug molecules, enabling controlled release and targeted delivery, thus improving the therapeutic efficacy and reducing side effects.
Used in Biomedical Applications:
3,9-BIS(3-AMINOPROPYL)-2,4,8,10-TETRAOXASPIRO[5.5]UNDECANE has shown promise in biomedical applications due to its biocompatibility and ability to form hydrogels. These hydrogels can be used for tissue engineering, wound healing, and as scaffolds for cell growth.
Used in Corrosion Inhibition:
3,9-BIS(3-AMINOPROPYL)-2,4,8,10-TETRAOXASPIRO[5.5]UNDECANE exhibits potential as a corrosion inhibitor. Its spiro-orthoester structure and amino groups can form protective layers on metal surfaces, reducing the rate of corrosion and extending the service life of materials in harsh environments.
Used in Polymer Property Enhancement:
3,9-BIS(3-AMINOPROPYL)-2,4,8,10-TETRAOXASPIRO[5.5]UNDECANE is used as a modifier to enhance the properties of polymers. By incorporating this spiropolymer into polymer matrices, the overall performance of the material can be improved, including its mechanical strength, thermal stability, and resistance to environmental factors.

InChI:InChI=1/C13H26N2O4/c14-5-1-3-11-16-7-13(8-17-11)9-18-12(19-10-13)4-2-6-15/h11-12H,1-10,14-15H2

Synthetic route

furfural (98-01-1) + 3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) → (1-furan-2-yl-methylene)-[3-(9-[3-(1-furan-2-yl-methylene)aminopropyl])-2,4,8,10-tetra-oxa-spiro[5.5]undec-3-yl-propyl]amine (130260-41-2)

Conditions	Yield
for 0.0333333h; Microwave irradiation;	92%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + iminodiacetic acid (142-73-4) → 1-(3-(9-(3-(2,6-dioxopiperazin-1-yl)propyl)-(2,4,8,10-tetraoxaspiro[5,5]-undecane-3-yl))propyl)piperazine-2,6-dione

Conditions	Yield
at 120℃; for 0.05h; Microwave irradiation;	91%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + 1,2,3,6-Tetrahydrophthalic anhydride (85-43-8) → 2-(3-(9-(3-(1,3-dioxo-3a,4,7,7a-tetrahydro-1H-isoindol-2(3H)-yl)propyl)-(2,4,8,10-tetraoxaspiro[5,5]-undecane-3-yl))propyl)-3a,4,7,7a-tetrahydro-2H-isoindole-1,3-dione

Conditions	Yield
at 150℃; for 0.0833333h; Microwave irradiation;	89%

di(succinimido) carbonate (74124-79-1) + 3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) → C23H32N4O12 (914931-72-9)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 3h; Product distribution / selectivity;	84%
In acetone at 20℃; for 3h; Product distribution / selectivity;	68%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + cobalt(II) chloride hexahydrate + C10H12N2O2 (1415246-56-8) → C53H70Cl2Co2N10O12

Conditions	Yield
Stage #1: cobalt(II) chloride hexahydrate; C10H12N2O2 In ethanol; water Inert atmosphere; Reflux; Stage #2: 3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) With air at 20℃; for 5h;	80%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + 1,2-Cyclohexanedicarboxylic acid-anhydride (85-42-7) → 2-(3-(9-(3-(1,3-dioxohexahydro-1H-isoindol-2(3H)-yl)propyl)-(2,4,8,10-tetraoxaspiro[5,5]-undecane-3-yl))propyl)hexahydro-2H-isoindole-1,3-dione

Conditions	Yield
at 150℃; for 0.0833333h; Microwave irradiation;	78%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + Homophthalic acid (89-51-0) → 2-(3-(9-(3-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)propyl)-(2,4,8,10-tetraoxaspiro[5,5]undecane-3-yl))propyl)isoquinolin-1,3(2H,4H)-dione

Conditions	Yield
at 150℃; for 0.0666667h; Microwave irradiation;	78%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + cobalt(II) chloride hexahydrate + methyl-p-tolyl-glyoxime (151194-62-6) → C53H70Cl2Co2N10O12

Conditions	Yield
Stage #1: cobalt(II) chloride hexahydrate; methyl-p-tolyl-glyoxime In ethanol; water Inert atmosphere; Reflux; Stage #2: 3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) With air at 20℃; for 5h;	78%

2,3-dicarboxypyrazine (89-01-0) + 3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) → 6-(3-(9-(3-(5,7-dioxo-5H-pyrrolo[3,4-b]pyrazin-6(7H)-yl)propyl)-(2,4,8,10-tetraoxaspiro[5,5]-undecane-3-yl))propyl)-6H-pyrrolo[3,4-b]pyrazine-5,7-dione

Conditions	Yield
at 120℃; for 0.0666667h; Microwave irradiation;	75%

4,5-imidazoledicarboxylic acid (570-22-9) + 3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) → 5-(3-(9-(3-(4,6-dioxopyrrolo[3,4-d]imidazol-5(1H,4H,6H)-yl)propyl)-(2,4,8,10-tetraoxaspiro[5,5]-undecane-3-yl))propyl)pyrrolo[3,4-d]imidazole-4,6(1H,5H)-dione

Conditions	Yield
at 120℃; for 0.0666667h; Microwave irradiation;	73%

methyl (4-pyridyl) ketone (1122-54-9) + 3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) → (1-pyridin-4-yl-ethylidene)-[3-(9-[3-(1-pyridin-4-yl-ethylideneamino)propyl]-2,4,8,10-tetraoxa-spiro[5.5]undec-3-yl)propyl]amine (1206770-27-5)

Conditions	Yield
In methanol; ethyl acetate for 0.0666667h; Microwave irradiation;	70%

Indole-3-carboxaldehyde (487-89-8) + 3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) → (1H-indol-3-yl-methylene)-[3-(9-{3-(1H-indol-3-yl-methylene)aminopropyl}-2,4,8,10-tetraoxa-spiro[5.5]undec-3-yl)]propylamine (1206770-25-3)

Conditions	Yield
In methanol; ethyl acetate for 0.0666667h; Microwave irradiation;	68%

9-Chloroacridine (1207-69-8) + 3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) → acridin-9-yl-[3-(9-{3-(acridin-9-ylamino)-propyl}-2,4,8,10-tetraoxa-spiro[5,5]undec-3-yl)-propyl]-amine

Conditions	Yield
In methanol for 18h; Reflux;	42%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + 9-isothiocyanato-2-methylacridine (24644-79-9) → 1-(3-(9-(3-(2-methyl-9-acridinylamine)methanethioamidopropyl)2,4,8,10-tetraoxa-spiro[5.5]undecane-3-yl)propyl)-3-(2-methylacridin-9-yl)thiourea

Conditions	Yield
In tetrahydrofuran at 20℃; for 6h;	39%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + 9-Isothiocyanato-4-methoxy-acridine (154389-38-5) → 1-(3-(9-(3-(4-methoxy-9-acridinylamine)methanethioamidopropyl)2,4,8,10-tetraoxa-spiro[5.5]undecane-3-yl)propyl)-3-(4-methoxyacridin-9-yl)thiourea

Conditions	Yield
In tetrahydrofuran at 20℃; for 6h;	39%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + 9-chloro-2-methoxyacridine (16492-13-0) → (2-methoxyacridin-9-yl)-[3-(9-{3-(2-methoxyacridin-9-ylamino)-propyl}-2,4,8,10-tetraoxa-spiro[5,5]undec-3-yl)-propyl]-amine

Conditions	Yield
In methanol for 17h; Reflux;	39%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + 9-chloro-4-methoxyacridine (16492-15-2) → (4-methoxyacridin-9-yl)-[3-(9-{3-(4-methoxyacridin-9-ylamino)-propyl}-2,4,8,10-tetraoxa-spiro[5,5]undec-3-yl)-propyl]-amine

Conditions	Yield
In methanol for 17h; Reflux;	38.2%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + 2-methoxy-9-acridine isothiocyanate (24628-52-2) → 1-(3-(9-(3-(2-methoxy-9-acridinylamine)methanethioamidopropyl)2,4,8,10-tetraoxa-spiro[5.5]undecane-3-yl)propyl)-3-(2-methoxyacridin-9-yl)thiourea

Conditions	Yield
In tetrahydrofuran at 20℃; for 6h;	38%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + 9-isothiocyanatoacridine (7620-46-4) → 1-(3-(9-(3-(9-acridinylamine)methanethioamidopropyl)2,4,8,10-tetraoxa-spiro[5.5]undecane-3-yl)propyl)-3-(acridin-9-yl)thiourea

Conditions	Yield
In tetrahydrofuran at 20℃; for 6h;	37%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + 4-methyl-9-isothiocyanatoacridine (24628-53-3) → 1-(3-(9-(3-(4-methyl-9-acridinylamine)methanethioamidopropyl)2,4,8,10-tetraoxa-spiro[5.5]undecane-3-yl)propyl)-3-(4-methylacridin-9-yl)thiourea

Conditions	Yield
In tetrahydrofuran at 20℃; for 6h;	37%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + (R,S)-3-isothiocyanatobutanal (111221-40-0, 27406-56-0) → C23H40N4O6S2

Conditions	Yield
In methanol at 20℃; for 240h;	36%

4-methyl-9-chloroacridine (16492-11-8) + 3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) → (4-methylacridin-9-yl)-[3-(9-{3-(4-methylacridin-9-ylamino)-propyl}-2,4,8,10-tetraoxa-spiro[5,5]undec-3-yl)-propyl]-amine

Conditions	Yield
In methanol for 17h; Reflux;	36%

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + acrylonitrile (107-13-1) → N,N,N',N'-tetrakis(2-cyanoethyl)-3,9-bis(aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecane (901792-15-2)

Conditions	Yield
In ethanol; water at 20 - 80℃; for 4h;

3,3'-(2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-diyl)bis(propan-1-amine) (21587-74-6) + Pyromellitic dianhydride (89-32-7) → poly(1,2,4,5-benzenetetracarboxylic dianhydride-co-3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxaspiroundecane)

Conditions	Yield
In ISOPROPYLAMIDE at 20℃; for 72h;