Product Name

  • Name

    3,3-Tetramethyleneglutarimide

  • EINECS 427-770-4
  • CAS No. 1075-89-4
  • Article Data5
  • CAS DataBase
  • Density 1.17 g/cm3
  • Solubility
  • Melting Point 153-155 °C
  • Formula C9H13NO2
  • Boiling Point 350.7 °C at 760 mmHg
  • Molecular Weight 167.208
  • Flash Point 162.6 °C
  • Transport Information
  • Appearance white to off-white crystalline powder
  • Safety 36/37/39-45
  • Risk Codes 28
  • Molecular Structure Molecular Structure of 1075-89-4 (3,3-Tetramethyleneglutarimide)
  • Hazard Symbols VeryT+
  • Synonyms 1,1-Cyclopentanediacetimide(6CI,7CI,8CI);8-Azaspiro[4.5]decane-7,9-dione;3-Spirocyclopentaneglutarimide;4,4-Tetramethyleneglutarimide;NSC 400092;b-Spirocyclopentaneglutarimide;
  • PSA 46.17000
  • LogP 1.31220

Synthetic route

3,3-tetramethylene glutaric anhydride
5662-95-3

3,3-tetramethylene glutaric anhydride

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

Conditions
ConditionsYield
With ammonium hydroxide In tetrahydrofuran at 190℃;92%
ammonium salt of/the/ cyclopentane-diacetic acid-(1.1)

ammonium salt of/the/ cyclopentane-diacetic acid-(1.1)

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

cyclopentane-dimalonic acid-(1.1)-monoamide

cyclopentane-dimalonic acid-(1.1)-monoamide

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

Conditions
ConditionsYield
ueber den Schmelzpunkt;
tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

propargyl bromide
106-96-7

propargyl bromide

8-Propargyl-8-azaspiro<4.5>decane-7,9-dione
25032-23-9

8-Propargyl-8-azaspiro<4.5>decane-7,9-dione

Conditions
ConditionsYield
With potassium carbonate In acetone for 10h; Heating;100%
With potassium carbonate In acetone Heating;100%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

N-(2-pyridinyl)piperazine
20980-22-7

N-(2-pyridinyl)piperazine

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

BUSPIRONE
36505-84-7

BUSPIRONE

Conditions
ConditionsYield
With potassium carbonate; benzyltriethylammonium bromide Product distribution; 1.) xylene, reflux, 3 h, 2.) reflux, 5 h; other imides and catalysts, variation of reaction time, also in toluene; also 1-(2-quinolinyl)piperazine;97%
With potassium carbonate; benzyltriethylammonium bromide 1.) xylene, reflux, 3 h, 2.) reflux, 5 h; Yield given. Multistep reaction;
...Expand
4-chlorobutanal dimethyl acetal
29882-07-3

4-chlorobutanal dimethyl acetal

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-(4,4-dimethoxybutyl)-8-azaspiro[4.5]decane-7,9-dione
1359159-58-2

8-(4,4-dimethoxybutyl)-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In dimethyl sulfoxide at 80℃; for 4h;96%
tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

benzyl bromide
100-39-0

benzyl bromide

8-benzyl-8-azaspiro[4.5]decane-7,9-dione
77261-38-2

8-benzyl-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
Stage #1: tetramethylene glutarimide With potassium carbonate for 1h;
Stage #2: benzyl bromide In acetone for 2h; Reflux; Inert atmosphere;		96%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-(tert-butoxycarbonyl)-7,9-dioxo-8-azaspiro[4.5]decane
854280-06-1

8-(tert-butoxycarbonyl)-7,9-dioxo-8-azaspiro[4.5]decane

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 15h;95%
tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

3-azaspiro[5.5]undecane
180-44-9

3-azaspiro[5.5]undecane

Conditions
ConditionsYield
In tetrahydrofuran94%
tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

benzoyl chloride
98-88-4

benzoyl chloride

8-benzoyl-8-azaspiro[4.5]decane-7,9-dione

8-benzoyl-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 15h; Schlenk technique; Inert atmosphere;94%
4-chlorobutyl bromide
6940-78-9

4-chlorobutyl bromide

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-(4-chlorobutyl)-8-azaspiro<4.5>decane-7,9-dione
21098-11-3

8-(4-chlorobutyl)-8-azaspiro<4.5>decane-7,9-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;93%
In N-methyl-acetamide
tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

4-bromobutanenitrile
5332-06-9

4-bromobutanenitrile

4-(7,9-dioxo-8-aza-spiro[4.5]dec-8-yl)butyronitrile
1236066-79-7

4-(7,9-dioxo-8-aza-spiro[4.5]dec-8-yl)butyronitrile

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile at 60℃; for 20h; Inert atmosphere;93%
tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-(2-quinolinyl)-8-aza-5-azoniaspiro<4.5>decane bromide
142415-01-8

8-(2-quinolinyl)-8-aza-5-azoniaspiro<4.5>decane bromide

Kaspar
142336-21-8

Kaspar

Conditions
ConditionsYield
With potassium carbonate; 18-crown-6 ether In xylene for 6h; Heating;89%
tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-(1,2-benzisothiazol-3-yl)-8-aza-5-azoniaspiro[4.5]decane bromide
87691-94-9

8-(1,2-benzisothiazol-3-yl)-8-aza-5-azoniaspiro[4.5]decane bromide

tiospirone
87691-91-6

tiospirone

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In toluene for 22h; Heating;88%
bromopropionitrile
2417-90-5

bromopropionitrile

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

3-(7,9-dioxo-8-aza-spiro[4.5]dec-8-yl)propionitrile
1236066-78-6

3-(7,9-dioxo-8-aza-spiro[4.5]dec-8-yl)propionitrile

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile at 60℃; for 20h; Inert atmosphere;87%
(E)-1,1-Difluorodec-3-en-2-yl Diethyl Phosphate

(E)-1,1-Difluorodec-3-en-2-yl Diethyl Phosphate

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

(E)-8-(1,1-difluorodec-2-en-4-yl)-8-azaspiro[4.5]decane-7,9-dione

(E)-8-(1,1-difluorodec-2-en-4-yl)-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); caesium carbonate In dimethyl sulfoxide at 30℃; for 1h; Inert atmosphere;87%
tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

6-methyl-4-bromomethylcoumarin
79344-41-5

6-methyl-4-bromomethylcoumarin

8-[(6-methyl-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

8-[(6-methyl-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
Stage #1: tetramethylene glutarimide With potassium carbonate In acetone at 20℃; for 0.666667h;
Stage #2: 6-methyl-4-bromomethylcoumarin In acetone at 55 - 60℃; for 10h;		85%
tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

6-chloro-4-bromomethylcoumarin
79344-40-4

6-chloro-4-bromomethylcoumarin

8-[(6-chloro-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

8-[(6-chloro-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
Stage #1: tetramethylene glutarimide With potassium carbonate In acetone at 20℃; for 0.666667h;
Stage #2: 6-chloro-4-bromomethylcoumarin In acetone at 55 - 60℃; for 10h;		85%
tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

4-(bromomethyl)-7-chloro-2H-chromen-2-one
79344-39-1

4-(bromomethyl)-7-chloro-2H-chromen-2-one

8-[(7-chloro-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

8-[(7-chloro-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
Stage #1: tetramethylene glutarimide With potassium carbonate In acetone at 20℃; for 0.666667h;
Stage #2: 4-(bromomethyl)-7-chloro-2H-chromen-2-one In acetone at 55 - 60℃; for 10h;		85%
4-(bromomethyl)-7,8-dimethyl-2H-chromen-2-one
1252026-46-2

4-(bromomethyl)-7,8-dimethyl-2H-chromen-2-one

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-[(7,8-dimethyl-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

8-[(7,8-dimethyl-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
Stage #1: tetramethylene glutarimide With potassium carbonate In acetone at 20℃; for 0.666667h;
Stage #2: 4-(bromomethyl)-7,8-dimethyl-2H-chromen-2-one In acetone at 55 - 60℃; for 10h;		85%
tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

4-bromomethyl-6-methoxycoumarin
82156-57-8

4-bromomethyl-6-methoxycoumarin

8-[(6-methoxy-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

8-[(6-methoxy-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
Stage #1: tetramethylene glutarimide With potassium carbonate In acetone at 20℃; for 0.666667h;
Stage #2: 4-bromomethyl-6-methoxycoumarin In acetone at 55 - 60℃; for 10h;		85%
4-(bromomethyl)-7-methoxycoumarin
35231-44-8

4-(bromomethyl)-7-methoxycoumarin

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-[(7-methoxy-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

8-[(7-methoxy-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
Stage #1: tetramethylene glutarimide With potassium carbonate In acetone at 20℃; for 0.666667h;
Stage #2: 4-(bromomethyl)-7-methoxycoumarin In acetone at 55 - 60℃; for 10h;		85%
6-bromo-4-(bromomethyl)–2H-chromen-2-one

6-bromo-4-(bromomethyl)–2H-chromen-2-one

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-[(6-bromo-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decan-7,9-dione

8-[(6-bromo-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decan-7,9-dione

Conditions
ConditionsYield
Stage #1: tetramethylene glutarimide With potassium carbonate In acetone at 20℃; for 0.666667h;
Stage #2: 6-bromo-4-(bromomethyl)–2H-chromen-2-one In acetone at 55 - 60℃; for 10h;		85%
4-(bromomethyl)-2H-naphthol[1,2-b]pyran-2-one
87317-83-7

4-(bromomethyl)-2H-naphthol[1,2-b]pyran-2-one

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-[(2-oxo-2H-benzo[h]chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

8-[(2-oxo-2H-benzo[h]chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
Stage #1: tetramethylene glutarimide With potassium carbonate In acetone at 20℃; for 0.666667h;
Stage #2: 4-(bromomethyl)-2H-naphthol[1,2-b]pyran-2-one In acetone at 55 - 60℃; for 10h;		85%
(4aS,8aR)-2-(1-(2-chloroacetyl)azetidin-3-yl)-4-(3,4-dimethoxyphenyl)-4a,5,8,8a-tetrahydrophthalazin-1(2H)-one

(4aS,8aR)-2-(1-(2-chloroacetyl)azetidin-3-yl)-4-(3,4-dimethoxyphenyl)-4a,5,8,8a-tetrahydrophthalazin-1(2H)-one

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-(2-(3-((4aS,8aR)-4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,8,8a-tetrahydrophthalazin-2(1H)-yl)azetidin-1-yl)-2-oxoethyl)-8-azaspiro[4.5]decane-7,9-dione

8-(2-(3-((4aS,8aR)-4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,8,8a-tetrahydrophthalazin-2(1H)-yl)azetidin-1-yl)-2-oxoethyl)-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h;80%
4-bromomethyl-7-methyl-coumarin
41321-75-9

4-bromomethyl-7-methyl-coumarin

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-[(7-methyl-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

8-[(7-methyl-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
Stage #1: tetramethylene glutarimide With potassium carbonate In acetone at 20℃; for 0.666667h;
Stage #2: 4-bromomethyl-7-methyl-coumarin In acetone at 55 - 60℃; for 10h;		80%
4-(bromomethyl)-5,7-dimethyl-2H-chromen-2-one
41295-53-8

4-(bromomethyl)-5,7-dimethyl-2H-chromen-2-one

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-[(5,7-dimethyl-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

8-[(5,7-dimethyl-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
Stage #1: tetramethylene glutarimide With potassium carbonate In acetone at 20℃; for 0.666667h;
Stage #2: 4-(bromomethyl)-5,7-dimethyl-2H-chromen-2-one In acetone at 55 - 60℃; for 10h;		80%
6-tert-butyl-4-(bromomethyl)-2H-chromen-2-one

6-tert-butyl-4-(bromomethyl)-2H-chromen-2-one

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-[(6-tert-butyl-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

8-[(6-tert-butyl-2-oxo-2H-chromen-4-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
Stage #1: tetramethylene glutarimide With potassium carbonate In acetone at 20℃; for 0.666667h;
Stage #2: 6-tert-butyl-4-(bromomethyl)-2H-chromen-2-one In acetone at 55 - 60℃; for 10h;		80%
5,6-benzo-4-bromomethylcoumarin
101553-94-0

5,6-benzo-4-bromomethylcoumarin

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-[(3-oxo-3H-benzo[f]chromen-1-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

8-[(3-oxo-3H-benzo[f]chromen-1-yl)methyl]-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
Stage #1: tetramethylene glutarimide With potassium carbonate In acetone at 20℃; for 0.666667h;
Stage #2: 5,6-benzo-4-bromomethylcoumarin In acetone at 55 - 60℃; for 10h;		80%
1,4-dibromo-2,2,3,3-tetradeuteriobutane
52089-63-1

1,4-dibromo-2,2,3,3-tetradeuteriobutane

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-(4-bromobutyl-2,2,3,3-d4)-8-azaspiro[4,5]decane-7,9-dione

8-(4-bromobutyl-2,2,3,3-d4)-8-azaspiro[4,5]decane-7,9-dione

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 14h; Alkylation; Heating;77.92%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-(4-bromobutyl)-8-azaspiro[4.5]decane-7,9-dione
80827-62-9

8-(4-bromobutyl)-8-azaspiro[4.5]decane-7,9-dione

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In toluene at 111℃; for 24h; Inert atmosphere;75%
With potassium carbonate; potassium iodide In acetonitrile at 60℃; for 6h;69%
1-bromo-4-butene
5162-44-7

1-bromo-4-butene

tetramethylene glutarimide
1075-89-4

tetramethylene glutarimide

8-(3-butenyl)-8-azaspiro<4.5>decane-7,9-dione
131779-51-6

8-(3-butenyl)-8-azaspiro<4.5>decane-7,9-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide Heating;74%

3,3-Tetramethyleneglutarimide Specification

The 3,3-Tetramethyleneglutarimide, with the CAS registry number 1075-89-4, is also known as 8-Azaspiro[4,5]decane-7,9-dione. It belongs to the product categories of Building Blocks. Its EINECS registry number is 427-770-4. This chemical's molecular formula is C9H13NO2 and molecular weight is 167.21. Its IUPAC name is called 8-azaspiro[4.5]decane-7,9-dione. The product should be sealed and stored in cool and dry place.

Physical properties of 3,3-Tetramethyleneglutarimide: (1)ACD/LogP: 1.47; (2)ACD/LogD (pH 5.5): 1.47; (3)ACD/LogD (pH 7.4): 1.47; (4)ACD/BCF (pH 5.5): 7.76; (5)ACD/BCF (pH 7.4): 7.76; (6)ACD/KOC (pH 5.5): 150.92; (7)ACD/KOC (pH 7.4): 150.91; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)Index of Refraction: 1.523; (11)Molar Refractivity: 43.52 cm3; (12)Molar Volume: 142.4 cm3; (13)Surface Tension: 43.7 dyne/cm; (14)Density: 1.17 g/cm3; (15)Flash Point: 162.6 °C; (16)Enthalpy of Vaporization: 59.53 kJ/mol; (17)Boiling Point: 350.7 °C at 760 mmHg; (18)Vapour Pressure: 4.31E-05 mmHg at 25°C.

Uses of 3,3-Tetramethyleneglutarimide: it can be used to produce 8-(4-bromobutyl)-8-azaspiro[4.5]decane-7,9-dione at temperature of 60 °C. This reaction will need reagent KI, K2CO3 and solvent acetonitrile with reaction time of 6 hours. The yield is about 69%.

When you are using this chemical, please be cautious about it as the following:
This chemical that at very low levels can cause damage to health. It is very toxic if swallowed. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1CCC2(C1)CC(=O)NC(=O)C2
(2)InChI: InChI=1S/C9H13NO2/c11-7-5-9(3-1-2-4-9)6-8(12)10-7/h1-6H2,(H,10,11,12)
(3)InChIKey: YRTHJMQKDCXPAY-UHFFFAOYSA-N

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