Tetrahydrophthalimide supplier

Name
Tetrahydrophthalimide
EINECS 201-602-8
CAS No. 85-40-5
Article Data15
CAS DataBase
Density 1.228
Solubility 12.2g/L at 20℃
Melting Point 132-140 ºC
Formula C8H9 N O2
Boiling Point 337 ºC
Molecular Weight 151.165
Flash Point 165 ºC
Transport Information
Appearance white crystalline powder
Safety Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NO_x.
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4-Cyclohexene-1,2-dicarboximide(6CI,7CI,8CI); 1,2,3,6-Tetrahydrophthalimide;3a,4,7,7a-Tetrahydro-1H-isoindole-1,3(2H)-dione;3a,4,7,7a-Tetrahydroisoindole-1,3-dione; NSC 59011; Tetrahydrophthalic acidimide; Tetrahydrophthalimide; D4-Tetrahydrophthalimide
PSA 46.17000
LogP 0.55400

Synthetic route

: 2028-12-8
4-cyclohexene 1-carboxylic acid 2-carboxamide

: 85-40-5
1,2,3,6-tertahydrophthalimide

Conditions

Conditions	Yield
In 1,3,5-trimethyl-benzene at 170℃; for 2.5h; Temperature; Solvent; Large scale;	95%

: 85-43-8
1,2,3,6-Tetrahydrophthalic anhydride

: 85-40-5
1,2,3,6-tertahydrophthalimide

Conditions

Conditions	Yield
With choline chloride; urea at 140℃; for 1h; Green chemistry;	81%
With complex<3THFMg2Cl2OTiNCO>6 In pyridine Heating; Yield given;

anhydride or dicarboxylic acid: anhydride or dicarboxylic acid

: 85-40-5
1,2,3,6-tertahydrophthalimide

Conditions

Conditions	Yield
With ammonia at 180℃;	74%

: 42027-93-0
N-Hydroxymethyl-cis-4-cyclohexene-1,2-dicarboximide

: 85-40-5
1,2,3,6-tertahydrophthalimide

Conditions

Conditions	Yield
at 100℃; Substitution; Thermolysis;

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 83809-94-3
1,10-bis(methoxymethyl)-1,10-diaza-18-crown-6

: 91043-68-4
C30H44N4O8

Conditions

Conditions	Yield
In benzene reflux; 20 deg C, 2 h;	99%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 75-87-6
chloral

: N-(1-Hydroxy-2,2,2-trichloroethyl)-cis-4-cyclohexene-1,2-dicarboximide

Conditions

Conditions	Yield
In ethanol for 2.5h; Addition; Heating;	99%

: 109-65-9
1-bromo-butane

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 2021-19-4
2-butyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetone for 24h; Ambient temperature;	97%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 2555-11-5
octahydro-1H-isoindol-1-one

Conditions

Conditions	Yield
With [Ru4H6(p-cumene)4]Cl2; hydrogen In water at 90℃; under 45003.6 Torr; for 22h;	97%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 54512-75-3
1-bromo-5-chloropentane

: 929224-25-9
2-(5-chloropentyl)-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 60h;	92%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 928-96-1
(Z)-3-Hexen-1-ol

: 82478-58-8
((Z)-2-Hex-3-enyl)-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

Conditions

Conditions	Yield
With dimethyl azodicarboxylate; triphenylphosphine In tetrahydrofuran Ambient temperature; overnight;	90%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 141-32-2
acrylic acid n-butyl ester

: 1252935-87-7
butyl 3-(3a,4,7,7a-tetrahydro-1,3-dioxo-1H-isoindol-2(3H)-yl)propanoate

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammomium bromide at 100℃; for 1.5h; aza-Michael addition; Neat (no solvent);	90%

: 6940-78-9
4-chlorobutyl bromide

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 2-(4-chlorobutyl)-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;	87%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 623-91-6
diethyl Fumarate

: 1252935-79-7
diethyl 2-(3a,4,7,7a-tetrahydro-1,3-dioxo-1H-isoindol-2(3H)-yl)succinate

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammomium bromide at 100℃; for 2.5h; aza-Michael addition; Neat (no solvent);	85%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 732276-63-0
11-bromomethyl-tricosane

: 1266676-35-0
C32H57NO2

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 50℃; Inert atmosphere;	85%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 21911-68-2
ethyl 2-(p-tolylamino)acetate

: C19H22N2O4

Conditions

Conditions	Yield
With oxygen; copper(l) chloride In acetonitrile at 50℃; for 24h; Green chemistry; regioselective reaction;	85%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 541-41-3
chloroformic acid ethyl ester

: N-ethoxycarbonyl-1,2,3,6-tetrahydrophthalimide

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 4h;	82%

: 763-32-6
2-methyl-1-buten-4-ol

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 82478-57-7
2-(3-Methyl-but-3-enyl)-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

Conditions

Conditions	Yield
With dimethyl azodicarboxylate; triphenylphosphine In tetrahydrofuran Ambient temperature; overnight;	81%

: 182208-57-7
3-(1,2,4,4a,5,6-hexahydro-pyrazino[1,2-a]quinolin-3-yl)-propylamine

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 2-[3-(1,2,4,4a,5,6-hexahydro-pyrazino[1,2-a]quinolin-3-yl)-propyl]-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

Conditions

Conditions	Yield
In toluene Heating / reflux;	80%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 927-74-2
1-butyn-4-ol

: 82478-59-9
2-But-3-ynyl-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

Conditions

Conditions	Yield
With dimethyl azodicarboxylate; triphenylphosphine In tetrahydrofuran Ambient temperature; overnight;	78%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 62360-00-3
(Z)-2-fluoro-3-phenylprop-2-enyl acetate

: 108-95-2
phenol

: (Z)-2-(2-phenoxy-3-phenylallyl)-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)); caesium carbonate In toluene at 80℃; for 16h; Inert atmosphere; regioselective reaction;	78%

...Expand

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 24424-99-5
di-tert-butyl dicarbonate

: 3a,4,7,7a-tetrahydro-1H-isoindol-2(3H)-carboxylic acid tert-butylester

Conditions

Conditions	Yield
Stage #1: 1,2,3,6-tertahydrophthalimide With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 60℃; for 18h; Stage #2: di-tert-butyl dicarbonate With triethylamine In dichloromethane at 0 - 20℃; for 21.5h;	77.3%

: 126689-79-0
methyl 2-(m-tolylamino)acetate

: 85-40-5
1,2,3,6-tertahydrophthalimide

: C18H20N2O4

Conditions

Conditions	Yield
With oxygen; copper(l) chloride In acetonitrile at 50℃; for 24h; Green chemistry; regioselective reaction;	77%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 14595-35-8
di-n-propyl fumarate

: 1252935-80-0
dipropyl 2-(3a,4,7,7a-tetrahydro-1,3-dioxo-1H-isoindol-2(3H)-yl)succinate

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammomium bromide at 100℃; for 3.5h; aza-Michael addition; Neat (no solvent);	76%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 24424-99-5
di-tert-butyl dicarbonate

: 474925-37-6
(3aH,7aS)-tert-butyl 3a,4,7,7a-tetrahydro-1H-isoindole-2(3H)-carboxylate

Conditions

Conditions	Yield
Stage #1: 1,2,3,6-tertahydrophthalimide With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Heating; Stage #2: di-tert-butyl dicarbonate In dichloromethane for 1h; Further stages.;	73%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 109-64-8
1,3-dibromo-propane

: 56401-24-2
2-(3-bromopropyl)-3a,4.7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone at 40℃; for 8h;	72%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 105-75-9
dibutyl fumarate

: 1252935-81-1
dibutyl 2-(3a,4,7,7a-tetrahydro-1,3-dioxo-1H-isoindol-2(3H)-yl)succinate

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammomium bromide at 100℃; for 3.5h; aza-Michael addition; Neat (no solvent);	72%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 20314-74-3
fumaric acid dipentyl ester

: 1252935-82-2
dipentyl 2-(3a,4,7,7a-tetrahydro-1,3-dioxo-1H-isoindol-2(3H)-yl)succinate

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammomium bromide at 100℃; for 4h; aza-Michael addition; Neat (no solvent);	70%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 7299-55-0
pent-3-yn-2-one

: 2-((E)-4-Oxo-pent-2-enyl)-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

Conditions

Conditions	Yield
With triphenylphosphine	69%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 19139-31-2
dihexyl fumarate

: 1252935-83-3
dihexyl 2-(3a,4,7,7a-tetrahydro-1,3-dioxo-1H-isoindol-2(3H)-yl)succinate

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammomium bromide at 100℃; for 4.5h; aza-Michael addition; Neat (no solvent);	68%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 598-31-2
1-bromoacetone

: 54399-02-9
1-(Δ4-tetrahydrophthalimido)propan-2-one

Conditions

Conditions	Yield
With sodium ethanolate In ethanol for 2h; Heating;	64%

: 85-40-5
1,2,3,6-tertahydrophthalimide

: 20314-73-2
diheptyl fumarate

: 1252935-84-4
diheptyl 2-(3a,4,7,7a-tetrahydro-1,3-dioxo-1H-isoindol-2(3H)-yl)succinate

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammomium bromide at 100℃; for 5h; aza-Michael addition; Neat (no solvent);	63%

Tetrahydrophthalimide Chemical Properties

IUPAC Name: 3A,4,7,7A-Tetrahydroisoindole-1,3-dione (85-40-5)
Synonyms: 3A,4,7,7A-Tetrahydro-1h-isoindole-3(2h)-dione ; 3A,4,7,7A-tetrahydro-isoindole-3-dione ; 3-Alpha,4,7,7-alpha-tetrahydro-1h-isoindole-3(2h)-dione ; Delta(4)-tetrahydrophthalimide ; Delta(sup4)-tetrahydrophthalimide ; Tetrahydrophthalimide ; 4-Cyclohexene-1,2-dicarboximide ; 1,2,3,6-Tetrahydrophthalimide
CAS: 85-40-5
MF: C₈H₉NO₂
MW: 151.16
MS:
EINECS: 201-602-8
Product Categories:
Mol File: 85-40-5.mol
Surface Tension: 42.1 dyne/cm
Density: 1.228 g/cm³
Flash Point: 165 °C
Melting point: 132-140°C
Enthalpy of Vaporization: 57.99 kJ/mol
Boiling Point: 336.8 °C at 760 mmHg
Vapour Pressure: 0.00011 mmHg at 25°C

Tetrahydrophthalimide Consensus Reports

Reported in EPA TSCA Inventory.

Product Name

Tetrahydrophthalimide

Synthetic route

Tetrahydrophthalimide Chemical Properties

Tetrahydrophthalimide Consensus Reports

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