1H-Isoindole,2,3-dihydro-5-methoxy- supplier

Name
5-METHOXY-2,3-DIHYDRO-1H-ISOINDOLE
EINECS
CAS No. 127168-88-1
Article Data12
CAS DataBase
Density 1.076g/cm³
Solubility
Melting Point
Formula C₉H₁₁NO
Boiling Point 254.14 °C at 760 mmHg
Molecular Weight 149.192
Flash Point 95.269 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5-Methoxy-2,3-dihydro-1H-isoindole;5-Methoxyisoindoline;
PSA 21.26000
LogP 1.62720

Synthetic route

: 50727-04-3
4-methoxyphthalimide

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

Conditions

Conditions	Yield
Stage #1: 4-methoxyphthalimide With borane-THF In tetrahydrofuran at 0℃; for 16h; Heating / reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water for 3h; Heating / reflux;	47%
Stage #1: 4-methoxyphthalimide With borane-THF In tetrahydrofuran at 0℃; for 16h; Heating / reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol at 0℃; for 3h; Heating / reflux;	47%
With borane In tetrahydrofuran at 0℃; for 16h; Heating / reflux;	47%

: 127168-89-2
N-benzylisoindolin-5-yl methyl ether

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

Conditions

Conditions	Yield
With Pd(OH)2/C; ammonium formate In methanol Reflux;
Stage #1: N-benzylisoindolin-5-yl methyl ether With hydrogen; acetic acid; palladium on carbon In methanol under 2327.23 Torr; for 23h; Stage #2: With sodium hydroxide; water In methanol

: 1025424-06-9
5-methoxy-2-[(4-methylphenyl)sulfonyl]isoindoline

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

Conditions

Conditions	Yield
With hydrogen bromide; phenol In propan-1-ol; water at 100℃; for 2h;

: 4685-47-6
3,4-dimethylanisole

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 5-hydroxy-isoindoline hydrobromide

Conditions

Conditions	Yield
With hydrogen bromide In water at 100℃;	95%
With hydrogen bromide In water for 16h; Heating / reflux;	93%
With hydrogen bromide In water for 16h; Heating / reflux;	93%

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 54544-67-1
5-hydroxyisoindoline

Conditions

Conditions	Yield
With hydrogen bromide at 100℃; for 2h;	80%

: 7693-44-9
4-bromophenyl chloroformate

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 1620228-48-9
4-bromophenyl 5-methoxyisoindoline-2-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1h;	63%

: 1620226-65-4
2-(4-(4-oxo-3,4-dihydrophthalazin-1-yl)phenyl)acetic acid

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 1620222-40-3
4-(4-(2-(5-methoxyisoindolin-2-yl)-2-oxoethyl)phenyl)phthalazin-1(2H)-one

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h;	59%

: tert-butyl 4-((1H-indazol-5-yl)amino)-2-chloro-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: tert-butyl 4-((1H-indazol-5-yl)amino)-2-(5-methoxyisoindolin-2-yl)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

Conditions

Conditions	Yield
With triethylamine In 1-methyl-pyrrolidin-2-one at 150℃; for 1h;	48.9%

: 3934-20-1
2,6-Dichloropyrimidine

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 2-(2-chloropyrimidin-4-yl)-5-methoxyisoindoline

Conditions

Conditions	Yield
With sodium carbonate In ethanol at 90℃; for 12h;	47.8%

: 260046-09-1
(4-bromophenyl)(2-chloropyrimidin-4-yl)amine

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: N-(4-bromophenyl)-2-(5-methoxyisoindolin-2-yl)pyrimidin-4-amine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 90℃; for 17h;	42.9%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 90℃; for 17h;	42.9%

: 7461-50-9
2-chloropyrimidin-4-amine

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 2-(5-methoxyisoindolin-2-yl)pyrimidin-4-amine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 90℃; for 16h;	35.4%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 90℃; for 16h;	35.4%

: N-(2-chloro-5,6-dimethylpyrimidin-4-yl)-1H-indazol-5-amine

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: N-(2-(5-methoxyisoindolin-2-yl)-5,6-dimethylpyrimidin-4-yl)-1H-indazol-5-amine

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 90℃; for 72h;	30%
With potassium carbonate In acetonitrile at 90℃; for 72h;	30%

: tert-butyl 4-((1H-indazol-5-yl)amino)-2-chloro-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: tert-butyl 4-((1H-indazol-5-yl)amino)-2-(5-methoxyisoindolin-2-yl)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

Conditions

Conditions	Yield
With triethylamine In 1-methyl-pyrrolidin-2-one at 150℃; for 1h;	29.6%

: 1257302-89-8
N-(2,5-dichloropyrimidin-4-yl)-1H-indazol-5-amine

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: N-(5-chloro-2-(5-methoxyisoindolin-2-yl)pyrimidin-4-yl)-1H-indazol-5-amine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 90℃; for 12h;	29.1%

: 1257302-90-1
N-(2-chloro-5-methylpyrimidin-4-yl)-1H-indazol-5-amine

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: N-(2-(5-methoxyisoindolin-2-yl)-5-methylpyrimidin-4-yl)-1H-indazol-5-amine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 110℃; for 12h;	27%

: N-(2-chloro-6-methylpyrimidin-4-yl)-1H-indazol-5-amine

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: N-(2-(5-methoxyisoindolin-2-yl)-6-methylpyrimidin-4-yl)-1H-indazol-5-amine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 110℃; for 12h;	21.4%

: 2-chloro-N-(1H-indazol-5-yl)-5,7-dihydrofuro[3,4-d]pyrimidin-4-amine

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: N-(1H-indazol-5-yl)-2-(5-methoxyisoindolin-2-yl)-5,7-dihydrofuro[3,4-d]pyrimidin-4-amine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 90℃; for 20h;	17.2%

: 575474-16-7
2-chloro-5-fluoro-N-(indazoline-5-yl)-4-pyrimidineamine

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: N-(5-fluoro-2-(5-methoxyisoindolin-2-yl)pyrimidin-4-yl)-1H-indazol-5-amine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 90℃; for 12h;	12.1%

: N-(1H-indazol-5-yl)-2-(methylsulfonyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-amine

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: N-(1H-indazol-5-yl)-2-(5-methoxyisoindolin-2-yl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-amine

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane at 150℃; for 2h; Microwave irradiation; Sealed tube;	7.23%

: 215790-29-7
trans-2-(1-(4-(N-tert-butoxycarbonyl)amino)cyclohexyl)acetaldehyde

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 437650-81-2
{4-[2-(5-methoxy-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With NaBH(OAc)2 In 1,2-dichloro-ethane at 20℃; for 16h;

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 263888-58-0
5-cyano-2,3-dihydro-1H-isoindole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 80 percent / aq. HBr / 2 h / 100 °C 2: 40 percent / Et3N / CH2Cl2 / 16 h / 20 °C 3: 70 percent / Et3N / CH2Cl2 / 6 h / -20 - 20 °C 4: 90 percent / Pd(PPh3)4 / dimethylformamide / 4 h / 100 °C 5: 90 percent / TFA / CH2Cl2 / 0.5 h / 40 °C View Scheme

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 263888-60-4
5-methanesulfonyloxy-2,3-dihydro-1H-isoindole

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / aq. HBr / 2 h / 100 °C 2: 40 percent / Et3N / CH2Cl2 / 16 h / 20 °C 3: 70 percent / Et3N / CH2Cl2 / 16 h / 20 °C 4: 90 percent / TFA / CH2Cl2 / 0.5 h / 40 °C View Scheme

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 226070-47-9
tert-butyl 5-hydroxyisoindoline-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / aq. HBr / 2 h / 100 °C 2: 40 percent / Et3N / CH2Cl2 / 16 h / 20 °C View Scheme

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 263888-56-8
tert-butyl 5-cyanoisoindoline-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / aq. HBr / 2 h / 100 °C 2: 40 percent / Et3N / CH2Cl2 / 16 h / 20 °C 3: 70 percent / Et3N / CH2Cl2 / 6 h / -20 - 20 °C 4: 90 percent / Pd(PPh3)4 / dimethylformamide / 4 h / 100 °C View Scheme

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 263888-59-1
5-methanesulfonyloxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / aq. HBr / 2 h / 100 °C 2: 40 percent / Et3N / CH2Cl2 / 16 h / 20 °C 3: 70 percent / Et3N / CH2Cl2 / 16 h / 20 °C View Scheme

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 437651-98-4
4-[2-(5-methoxy-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclohexylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH(OAc)2 / 1,2-dichloro-ethane / 16 h / 20 °C 2: 90 percent / TFA / CH2Cl2 / 0.5 h / 40 °C View Scheme

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 263888-57-9
5-trifluoromethanesulfonyloxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / aq. HBr / 2 h / 100 °C 2: 40 percent / Et3N / CH2Cl2 / 16 h / 20 °C 3: 70 percent / Et3N / CH2Cl2 / 6 h / -20 - 20 °C View Scheme

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 437652-04-5
2-[2-(4-amino-cyclohexyl)-ethyl]-2,3-dihydro-1H-isoindole-5-carbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 80 percent / aq. HBr / 2 h / 100 °C 2: 40 percent / Et3N / CH2Cl2 / 16 h / 20 °C 3: 70 percent / Et3N / CH2Cl2 / 6 h / -20 - 20 °C 4: 90 percent / Pd(PPh3)4 / dimethylformamide / 4 h / 100 °C 5: 90 percent / TFA / CH2Cl2 / 0.5 h / 40 °C 6: NaBH(OAc)2 / 1,2-dichloro-ethane / 16 h / 20 °C 7: 90 percent / TFA / CH2Cl2 / 0.5 h / 40 °C View Scheme

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 437652-01-2
methanesulfonic acid 2-[2-(4-amino-cyclohexyl)-ethyl]-2,3-dihydro-1H-isoindol-5-yl ester

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 80 percent / aq. HBr / 2 h / 100 °C 2: 40 percent / Et3N / CH2Cl2 / 16 h / 20 °C 3: 70 percent / Et3N / CH2Cl2 / 16 h / 20 °C 4: 90 percent / TFA / CH2Cl2 / 0.5 h / 40 °C 5: NaBH(OAc)2 / 1,2-dichloro-ethane / 16 h / 20 °C 6: 90 percent / TFA / CH2Cl2 / 0.5 h / 40 °C View Scheme

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 437651-10-0
{4-[2-(5-cyano-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 80 percent / aq. HBr / 2 h / 100 °C 2: 40 percent / Et3N / CH2Cl2 / 16 h / 20 °C 3: 70 percent / Et3N / CH2Cl2 / 6 h / -20 - 20 °C 4: 90 percent / Pd(PPh3)4 / dimethylformamide / 4 h / 100 °C 5: 90 percent / TFA / CH2Cl2 / 0.5 h / 40 °C 6: NaBH(OAc)2 / 1,2-dichloro-ethane / 16 h / 20 °C View Scheme

: 127168-88-1
5-methoxy-2,3-dihydro-1H-isoindole

: 437650-82-3
methanesulfonic acid 2-[2-(4-tert-butoxycarbonylamino-cyclohexyl)-ethyl]-2,3-dihydro-1H-isoindol-5-yl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 80 percent / aq. HBr / 2 h / 100 °C 2: 40 percent / Et3N / CH2Cl2 / 16 h / 20 °C 3: 70 percent / Et3N / CH2Cl2 / 16 h / 20 °C 4: 90 percent / TFA / CH2Cl2 / 0.5 h / 40 °C 5: NaBH(OAc)2 / 1,2-dichloro-ethane / 16 h / 20 °C View Scheme

1H-Isoindole,2,3-dihydro-5-methoxy- Specification

The 1H-Isoindole,2,3-dihydro-5-methoxy-, with CAS registry number 127168-88-1, belongs to the following product category: Heterocycles series. It has the systematic name of 5-methoxy-2,3-dihydro-1H-isoindole. And the chemical formula of this chemical is C₉H₁₁NO.

Physical properties of 1H-Isoindole,2,3-dihydro-5-methoxy-: (1)ACD/LogP: 1.30; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 2; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 21.26 Å²; (11)Index of Refraction: 1.546; (12)Molar Refractivity: 43.842 cm³; (13)Molar Volume: 138.56 cm³; (14)Polarizability: 17.38×10^-24cm³; (15)Surface Tension: 37.525 dyne/cm; (16)Density: 1.077 g/cm³; (17)Flash Point: 95.269 °C; (18)Enthalpy of Vaporization: 49.156 kJ/mol; (19)Boiling Point: 254.14 °C at 760 mmHg; (20)Vapour Pressure: 0.018 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: COc1ccc2c(c1)CNC2
(2)InChI: InChI=1/C9H11NO/c1-11-9-3-2-7-5-10-6-8(7)4-9/h2-4,10H,5-6H2,1H3
(3)InChIKey: BNBIUUBEQGUPJK-UHFFFAOYAF
(4)Std. InChI: InChI=1S/C9H11NO/c1-11-9-3-2-7-5-10-6-8(7)4-9/h2-4,10H,5-6H2,1H3
(5)Std. InChIKey: BNBIUUBEQGUPJK-UHFFFAOYSA-N

Product Name

5-METHOXY-2,3-DIHYDRO-1H-ISOINDOLE

Synthetic route

1H-Isoindole,2,3-dihydro-5-methoxy- Specification

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