Isoindoline supplier | CasNO.496-12-8

Name
Isoindoline
EINECS
CAS No. 496-12-8
Article Data65
CAS DataBase
Density 1.04 g/cm³
Solubility
Melting Point 17 °C(lit.)
Formula C₈H₉N
Boiling Point 199.6 °C at 760 mmHg
Molecular Weight 119.166
Flash Point 75.8 °C
Transport Information
Appearance COLORLESS TO ORANGE TO BROWN LIQUID
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Isoindoline(6CI,7CI,8CI);1,3-Dihydro-2H-isoindole;1,3-Dihydroisoindole;2,3-Dihydro-1H-isoindole;
PSA 12.03000
LogP 1.61860

Synthetic route

: 32372-83-1
2(toluene-p-sulphonyl)isoindoline

: 496-12-8
isoindoline

Conditions

Conditions	Yield
With hydrogen bromide; propionic acid; phenol for 2h; Inert atmosphere; Reflux;	93%
With hydrogen bromide; phenol In propionic acid for 2h; Heating;	61%
With hydrogen bromide; propionic acid; phenol

: 53175-33-0
N-(2-furylmethyl)-N-(prop-2-en-1-yl)amine

: 496-12-8
isoindoline

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydrogencarbonate 1.) ether, 90 deg C, 32 h, 2.) H2O;	85%

: 35180-14-4
2-benzylisoindoline

: 496-12-8
isoindoline

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol	84%
With iodine; hypophosphorous acid; acetic acid for 12h; Heating;	75%
With ethanol; palladium
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 8h;
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 8h;

: 270-69-9
isoindoline

: 496-12-8
isoindoline

Conditions

Conditions	Yield
With sodium cyanoborohydride In methanol at 25℃; for 3h;	80%

: 136918-14-4
phthalimide

: 496-12-8
isoindoline

Conditions

Conditions	Yield
With borane-THF In tetrahydrofuran for 14h; Inert atmosphere; Reflux;	78%
With borane-THF In tetrahydrofuran for 14h; Heating;	50%
With sulfuric acid at 60℃; bei der elektrolytischen Reduktion;

: 91-15-6
phthalonitrile

: 496-12-8
isoindoline

Conditions

Conditions	Yield
platinum In tetrahydrofuran	75%
With cobalt catalyst; ammonia at 100℃; under 73550.8 Torr; Hydrogenation.Reagens 4: Dioxan;
With ammonia; nickel at 100℃; under 73550.8 Torr; Hydrogenation.Reagens 4: Dioxan;

: 612-12-4
o-Xylylene dichloride

: 496-12-8
isoindoline

Conditions

Conditions	Yield
With ammonia; potassium carbonate In water at 120℃; for 0.333333h; microwave irradiation;	62%
With hydrogenchloride; hexamethylenetetramine; triethylamine 1.) CHCl3, reflux, 4 h; 2.) EtOH, 12 h; 3.) reflux, 8 h;	44%

: 480-91-1
oxisoindole

: 496-12-8
isoindoline

Conditions

Conditions	Yield
With sulfuric acid at 50℃; Electrolysis.Verwendung einer Cadmium-Kathode;
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 45℃; for 3h; Inert atmosphere;

: 136918-14-4
phthalimide

A: 496-12-8
isoindoline

B: 480-91-1
oxisoindole

Conditions

Conditions	Yield
With sulfuric acid at 40℃; Bei der elektrochemischen Reduktion an einer Zink-Amalgam-Kathode unter Normaldruck,bei 5.3 at und bei 8.5 at;

: 136918-14-4
phthalimide

A: 496-12-8
isoindoline

B: 1,2,1',3'-tetrahydro-[1,2']biisoindolyl-3-one

Conditions

Conditions	Yield
bei der elektrochemischen Reduktion an einer Blei-Kathode in wss. H2SO4;

: 611-31-4
1H-2,3-benzoxazin-1-one

: 496-12-8
isoindoline

Conditions

Conditions	Yield
With acetic acid; zinc

: 5784-45-2
1-chlorophthalazine

: 496-12-8
isoindoline

Conditions

Conditions	Yield
With hydrogenchloride; zinc
With hydrogenchloride; tin

: 17300-02-6
1,2-benzenedimethanamine

: 496-12-8
isoindoline

Conditions

Conditions	Yield
With diethyl ether; N-phenylsulfinylamine

: 38379-25-8
o-chloromethylbenzylamine

: furan-2,3,5(4H)-trione pyridine (1:1)

A: 496-12-8
isoindoline

B: 118621-12-8
2-isoindolin-2-ylmethyl-benzylamine

...Expand

: 38379-25-8
o-chloromethylbenzylamine

: 496-12-8
isoindoline

Conditions

Conditions	Yield
With sodium hydroxide

: 7647-01-0
hydrogenchloride

: 3364-57-6
1,3-dihydro-isoindole-2-carboxylic acid amide

: 496-12-8
isoindoline

Conditions

Conditions	Yield
at 160 - 170℃;

: 136918-14-4
phthalimide

: 7664-93-9
sulfuric acid

: 496-12-8
isoindoline

Conditions

Conditions	Yield
at 18 - 20℃; bei elektrolytischen Reduktion an Bleikathoden,zuletz 60grad;

: 3364-57-6
1,3-dihydro-isoindole-2-carboxylic acid amide

: 7664-93-9
sulfuric acid

: 496-12-8
isoindoline

: 7732-18-5
water

: 118621-12-8
2-isoindolin-2-ylmethyl-benzylamine

: 496-12-8
isoindoline

Conditions

Conditions	Yield
at 200℃; im Rohr;

isoindoline-N-carboxylic acid amide: isoindoline-N-carboxylic acid amide

: 496-12-8
isoindoline

Conditions

Conditions	Yield
With sulfuric acid
With hydrogenchloride at 160 - 170℃;

: 136918-14-4
phthalimide

: 60-29-7
diethyl ether

lithium alanate: lithium alanate

: 496-12-8
isoindoline

...Expand

N.N.-o-xylylene-piperidinium bromide: N.N.-o-xylylene-piperidinium bromide

: 496-12-8
isoindoline

Conditions

Conditions	Yield
With ammonia at 200℃;

N.N-o-xylylene-isoindolinium bromide: N.N-o-xylylene-isoindolinium bromide

: 496-12-8
isoindoline

Conditions

Conditions	Yield
With ammonia at 250℃; im Rohr;

o-xylylenediamine hydrochloride: o-xylylenediamine hydrochloride

: 496-12-8
isoindoline

: 7647-01-0
hydrogenchloride

: 5784-45-2
1-chlorophthalazine

tin: tin

: 496-12-8
isoindoline

...Expand

: 7647-01-0
hydrogenchloride

: 5784-45-2
1-chlorophthalazine

zinc: zinc

: 496-12-8
isoindoline

...Expand

: 32743-18-3
(2-(piperidin-1-ylmethyl)phenyl)methanamine

: 7732-18-5
water

A: 110-89-4
piperidine

B: 496-12-8
isoindoline

Conditions

Conditions	Yield
at 200℃; im Rohr;

...Expand

: 136918-14-4
phthalimide

: 64-17-5
ethanol

: 7664-93-9
sulfuric acid

: 7732-18-5
water

A: 496-12-8
isoindoline

B: 480-91-1
oxisoindole

Conditions

Conditions	Yield
under 6251.8 Torr; Elektrochemische Reduktion an einer Zink-Amalgam-Kathode;
under 735.5 Torr; Elektrochemische Reduktion an einer Zink-Amalgam-Kathode;
under 3898.2 Torr; Elektrochemische Reduktion an einer Zink-Amalgam-Kathode;

...Expand

: 611-31-4
1H-2,3-benzoxazin-1-one

: 64-19-7
acetic acid

zinc dust: zinc dust

A: 496-12-8
isoindoline

B: 480-91-1
oxisoindole

C: 136918-14-4
phthalimide

...Expand

: 496-12-8
isoindoline

: 6283-74-5
(3R-trans)-dihydro-2,5-dioxofuran-3,4-diyl diacetate

: 871713-99-4
C16H17NO7

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 2h;	100%

: 496-12-8
isoindoline

: 367-86-2
1-fluoro-2-nitro-4-trifluoromethyl-benzene

: 858126-28-0
2-[2-nitro-4-(trifluoromethyl)phenyl]isoindoline

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	100%

: 496-12-8
isoindoline

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

: 260412-75-7
tert-butyl isoindoline-2-carboxylate

Conditions

Conditions	Yield
With triethylamine In dichloromethane	100%
With triethylamine In dichloromethane

: 496-12-8
isoindoline

: 98-09-9
benzenesulfonyl chloride

: 2-benzenesulfonyl-isoindoline

Conditions

Conditions	Yield
With pyridine at 20℃;	100%
In pyridine at 20℃; for 20h;

: 496-12-8
isoindoline

: 2-[4-(4-tert-butylphenyl)sulfonylpiperazin-1-yl]propanoic acid hydrochloride

: 2-[4-(4-tert-butylphenyl)sulfonylpiperazin-1-yl]-1-isoindolin-2-yl-propan-1-one

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h;	100%

: 496-12-8
isoindoline

: 693-13-0
diisopropyl-carbodiimide

: (E)-N,N'-diisopropylisoindoline-2-carboxamidine

Conditions

Conditions	Yield
[Y((CH3)4C5Si(CH3)2N(phenyl))(trimethylsilylmethyl)(tetrahydrofuran)2] In benzene at 80℃; for 0.5h;	99%
[{Me2Si(C5Me4)(NPh)}Y(CH2SiMe3)(thf)2] In benzene at 80℃; for 0.5h;

: 496-12-8
isoindoline

: 407-25-0
trifluoroacetic anhydride

: 832-51-9
1-(1,3-dihydro-2H-isoindol-2-yl)-2,2,2-trifluoroethanone

Conditions

Conditions	Yield
With pyridine; dmap In chloroform at 0 - 20℃; for 4h;	99%
With pyridine; dmap In chloroform at 20℃; for 4h; Cooling with ice;	8.66 g

: 496-12-8
isoindoline

: N-methyl-4,6-bis(perfluorophenoxy)-1,3,5-triazin-2-amine

: 4-(isoindolin-2-yl)-N-methyl-6-(perfluorophenoxy)-1,3,5-triazin-2-amine

Conditions

Conditions	Yield
Stage #1: N-methyl-4,6-bis(perfluorophenoxy)-1,3,5-triazin-2-amine With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.0833333h; Cooling with ice; Stage #2: isoindoline In dichloromethane at 0 - 20℃; for 72.0833h;	99%

: 496-12-8
isoindoline

: 143815-60-5
2-chloro-5-cyano-6-ethoxy-4-phenylpyridine-3-carboxaldehyde

: 147034-20-6
6-(1,3-Dihydro-isoindol-2-yl)-2-ethoxy-5-formyl-4-phenyl-nicotinonitrile

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 0.166667h; Heating;	97%

: 496-12-8
isoindoline

: 2131-55-7
4-Chlorophenyl isothiocyanate

: 915104-40-4
N-(4-Chlorophenyl)-1 ,3-dihydro-2H-isoindole-2-carbothioamide

Conditions

Conditions	Yield
In ethanol	97%

: 496-12-8
isoindoline

: 85822-16-8
4-formylbenzene-1-sulfonyl chloride

: 780777-94-8
4-(1,3-dihydro-isoindole-2-sulfonyl)-benzaldehyde

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h;	96%

: 496-12-8
isoindoline

: 912545-10-9
2,4-bis(benzyloxy)-5-bromobenzoic acid

: 913000-15-4
(2,4-bis-benzyloxy-5-bromophenyl)-(1,3-dihydroisoindol-2-yl)methanone

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3h;	96%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	70%

: 496-12-8
isoindoline

: 383-63-1
ethyl trifluoroacetate,

: 832-51-9
1-(1,3-dihydro-2H-isoindol-2-yl)-2,2,2-trifluoroethanone

Conditions

Conditions	Yield
In methanol at 45℃;	96%

: 496-12-8
isoindoline

: 127208-63-3
N,N-dimethyl-N'-(1-methoxy-2-methyl-2-propyl) formamidine

: [1-(1,3-Dihydro-isoindol-2-yl)-meth-(E)-ylidene]-(2-methoxy-1,1-dimethyl-ethyl)-amine

Conditions

Conditions	Yield
Heating;	95%

: 496-12-8
isoindoline

: 65051-83-4
3-methyl-3-phenylcyclopropene

: 2-((1R,2S)-2-methyl-2-phenylcyclopropyl)isoindoline

Conditions

Conditions	Yield
With C39H27(1-)2C9H12N(1-)Sm(3+) In toluene at 25℃; for 12h; Inert atmosphere; enantioselective reaction;	95%

: 496-12-8
isoindoline

: 1138-52-9
3,5-Di-tert-butylphenol

: C22H27NO

Conditions

Conditions	Yield
Stage #1: 3,5-Di-tert-butylphenol With tetrakis(actonitrile)copper(I) hexafluorophosphate; N,N'-di-tert-butylethylenediamine; oxygen at 23℃; under 760.051 Torr; for 4h; Stage #2: isoindoline With oxygen at 50℃; under 760.051 Torr; for 4h; Stage #3: With sodium tetrahydroborate at 0 - 23℃; for 2h;	95%

: 496-12-8
isoindoline

: C18H8Cl2N4

: C34H24N6

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran for 12h; Inert atmosphere; Reflux;	95%

: 496-12-8
isoindoline

: 37408-18-7
4-chloro-2-methylphenyl isocyanate

: N-(4-chloro-2-methylphenyl)isoindoline-2-carboxamide

Conditions

Conditions	Yield
In 1,4-dioxane at 20℃;	94%

: 496-12-8
isoindoline

: 27436-93-7
pentacarbonyl(1-methoxybenzylidene)chromium(0)

: 117041-18-6
(CO)5CrC(C6H5)NC8H8

Conditions

Conditions	Yield
In tetrahydrofuran Isoindoline was added to a THF soln. of (CO)5CrC(OCH3)C6H5. The solvent was removed under vac..; elem.anal.;	94%

: 496-12-8
isoindoline

: 23314-06-9
N,N-dimethyl-N'-tert-butylformamidine

: 127797-30-2
N-(tert-butyliminomethyl)isoindoline

Conditions

Conditions	Yield
With ammonium sulfate In toluene for 4.5h; Heating;	93%
With ammonium sulfate In toluene for 20h; Reflux; Inert atmosphere;	71%

: 496-12-8
isoindoline

: 291775-53-6
(1S,3R,4R)-N-tert-butoxycarbonyl-2-azabicyclo[2.2.1]heptane-3-carboxylic acid

: 291775-63-8
(1S,3R,4R)-N-tert-butoxycarbonyl-3-(N-isoindolinyl)carbonyl-2-azabicyclo[2.2.1]heptane

Conditions

Conditions	Yield
Stage #1: (1S,3R,4R)-N-tert-butoxycarbonyl-2-azabicyclo[2.2.1]heptane-3-carboxylic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane at 0℃; for 0.25h; Condensation; Stage #2: isoindoline In dichloromethane at 20℃; Acylation; Further stages.;	93%

: 496-12-8
isoindoline

: 56-05-3
2-Amino-4,6-dichloropyrimidine

: 1013110-41-2
4-chloro-6-(1,3-dihydro-2H-isoindol-2-yl)pyrimidin-2-amine

Conditions

Conditions	Yield
With triethylamine In ethanol at 85℃; for 6h;	93%

: 496-12-8
isoindoline

: 105-07-7
4-cyanobenzaldehyde

: 4-(isoindoline-2-carbonyl)benzonitrile

Conditions

Conditions	Yield
With 2,8-dibromo-5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-dipyrrolo[1,2-c:2′,1′-f ][1,3,2]diazaborinin-4-ium-5-uide; 2,6-di-tert-butyl-4-methyl-phenol; oxygen In 1,4-dioxane at 25℃; for 12h; Sealed tube; Irradiation; Green chemistry;	93%

: 496-12-8
isoindoline

: 2-(4-(4-[(tert-butoxycarbonyl)(methyl)amino]thieno[3,2-d]pyrimidin-2-yl)piperazino)acetic acid

: tert-butyl 2-(4-(2-(isoindolin-2-yl)-2-oxoethyl)piperazin-1-yl)thieno[3,2-d]pyrimidin-4-yl(methyl)carbamate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 18h;	93%

: 496-12-8
isoindoline

: 35202-16-5
5-chloro-2,4-dimethoxy-6-methylbenzoic acid

: 914298-87-6
(3-chloro-4,6-dimethoxy-2-methylphenyl)(isoindolin-2-yl)methanone

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 12h;	92%

: 496-12-8
isoindoline

: 102195-80-2
(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

: (2S,4R)-4-(1,3-dihydroisoindol-2-yl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Conditions

Conditions	Yield
Stage #1: isoindoline; (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate With acetic acid In dichloromethane for 1h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;	92%

: 496-12-8
isoindoline

: C18H14Cl2N2O2

: C34H30N4O2

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran for 12h; Inert atmosphere; Reflux;	92%

: 496-12-8
isoindoline

: 7338-94-5
1,3-diphenyl-2-propynone

: 741685-24-5
(E)-3-(2,3-dihydro-1H-2-isoindolyl)-1,3-diphenyl-2-propen-1-one

Conditions

Conditions	Yield
In diethyl ether for 12h;	91%

: 496-12-8
isoindoline

: 76-02-8
Trichloroacetyl chloride

: 914922-24-0
2,2,2-trichloro-1-(1,3-dihydro-2H-isoindol-2-yl)ethanone

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	91%
With triethylamine In chloroform at 20℃; for 1h; Cooling with ice;	6.59 g

Isoindoline Chemical Properties

IUPAC Name: 2,3-dihydro-1H-isoindole
Synonyms of 1H-Isoindole,2,3-dihydro- (CAS NO.496-12-8): dihydroisoindole ; isoindoline ; 2,3-dihydro-1h-isoindole ; 1,3-Dihydroisoindole ; 1,3-Dihydro-2H-isoindole ; o-Xyleneimine
CAS NO: 496-12-8
Molecular Formula of 1H-Isoindole,2,3-dihydro- (CAS NO.496-12-8): C₈H₉N
Molecular Weight: 119.1638
Molecular Structure:

H bond acceptors: 1
H bond donors: 1
Polar Surface Area: 3.24 Å²
Index of Refraction: 1.562
Molar Refractivity: 37.16 cm³
Molar Volume: 114.5 cm³
Surface Tension: 38.9 dyne/cm
Density of 1H-Isoindole,2,3-dihydro- (CAS NO.496-12-8): 1.04 g/cm³
Flash Point: 75.8 °C
Enthalpy of Vaporization: 43.58 kJ/mol
Boiling Point: 199.6 °C at 760 mmHg
Vapour Pressure: 0.338 mmHg at 25°C

Isoindoline Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
WGK Germany: 3

Product Name

Isoindoline

Synthetic route

Isoindoline Chemical Properties

Isoindoline Safety Profile

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