127168-88-1

Basic information

• Product Name: 5-METHOXY-2,3-DIHYDRO-1H-ISOINDOLE
• Synonyms: 5-METHOXY-2,3-DIHYDRO-1H-ISOINDOLE;5-METHOXYISOINDOLINE;5-METHOXY-2,3-DIHYDRO-1H-ISOINDOL;m90100;5-METHOXYISOINDOLINE HCL;1H-Isoindole,2,3-dihydro-5-Methoxy-;5-methoxyisoindoline 5-methoxy-2,3-dihydro-1h-isoindole;2,3-Dihydro-5-methoxy-1H-isoindole
• CAS NO: 127168-88-1
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.19
• Product Categories: Heterocycles series
• Mol File: 127168-88-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 254℃
• Flash Point: 95℃
• Appearance: /
• Density: 1.076
• Vapor Pressure: 0.018mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: 2-8°C(protect from light)
• PKA: 9.56±0.20(Predicted)
• CAS DataBase Reference: 5-METHOXY-2,3-DIHYDRO-1H-ISOINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-2,3-DIHYDRO-1H-ISOINDOLE(127168-88-1)
• EPA Substance Registry System: 5-METHOXY-2,3-DIHYDRO-1H-ISOINDOLE(127168-88-1)

Safety Data

• Hazardous Substances Data: 127168-88-1(Hazardous Substances Data)

Usage

Uses

5-Methoxyisoindoline is a reagent used in the sysnthesis of PDK inhibitors for used in targetting glucose and fat levels in type 2 diabetes. Also used in the preparation of C20’ ureas based on 20’amino-vinblastine for use against vinblastine-resistant cancer cell lines.

InChI:InChI=1/C9H11NO/c1-11-9-3-2-7-5-10-6-8(7)4-9/h2-4,10H,5-6H2,1H3

Synthetic route

4-methoxyphthalimide (50727-04-3) → 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1)

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%

N-benzylisoindolin-5-yl methyl ether (127168-89-2) → 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1)

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

5-methoxy-2-[(4-methylphenyl)sulfonyl]isoindoline (1025424-06-9) → 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1)

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

3,4-dimethylanisole (4685-47-6) → 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1)

5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → 5-hydroxy-isoindoline hydrobromide

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%

5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → 5-hydroxyisoindoline (54544-67-1)

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

4-bromophenyl chloroformate (7693-44-9) + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → 4-bromophenyl 5-methoxyisoindoline-2-carboxylate (1620228-48-9)

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

2-(4-(4-oxo-3,4-dihydrophthalazin-1-yl)phenyl)acetic acid (1620226-65-4) + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → 4-(4-(2-(5-methoxyisoindolin-2-yl)-2-oxoethyl)phenyl)phthalazin-1(2H)-one (1620222-40-3)

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 + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → tert-butyl 4-((1H-indazol-5-yl)amino)-2-(5-methoxyisoindolin-2-yl)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate

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

2,6-Dichloropyrimidine (3934-20-1) + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → 2-(2-chloropyrimidin-4-yl)-5-methoxyisoindoline

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

(4-bromophenyl)(2-chloropyrimidin-4-yl)amine (260046-09-1) + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → N-(4-bromophenyl)-2-(5-methoxyisoindolin-2-yl)pyrimidin-4-amine

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%

2-chloropyrimidin-4-amine (7461-50-9) + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → 2-(5-methoxyisoindolin-2-yl)pyrimidin-4-amine

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 + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → N-(2-(5-methoxyisoindolin-2-yl)-5,6-dimethylpyrimidin-4-yl)-1H-indazol-5-amine

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 + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → tert-butyl 4-((1H-indazol-5-yl)amino)-2-(5-methoxyisoindolin-2-yl)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

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

N-(2,5-dichloropyrimidin-4-yl)-1H-indazol-5-amine (1257302-89-8) + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → N-(5-chloro-2-(5-methoxyisoindolin-2-yl)pyrimidin-4-yl)-1H-indazol-5-amine

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

N-(2-chloro-5-methylpyrimidin-4-yl)-1H-indazol-5-amine (1257302-90-1) + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → N-(2-(5-methoxyisoindolin-2-yl)-5-methylpyrimidin-4-yl)-1H-indazol-5-amine

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 + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → N-(2-(5-methoxyisoindolin-2-yl)-6-methylpyrimidin-4-yl)-1H-indazol-5-amine

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 + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → N-(1H-indazol-5-yl)-2-(5-methoxyisoindolin-2-yl)-5,7-dihydrofuro[3,4-d]pyrimidin-4-amine

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

2-chloro-5-fluoro-N-(indazoline-5-yl)-4-pyrimidineamine (575474-16-7) + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → N-(5-fluoro-2-(5-methoxyisoindolin-2-yl)pyrimidin-4-yl)-1H-indazol-5-amine

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 + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → N-(1H-indazol-5-yl)-2-(5-methoxyisoindolin-2-yl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-amine

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

trans-2-(1-(4-(N-tert-butoxycarbonyl)amino)cyclohexyl)acetaldehyde (215790-29-7) + 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → {4-[2-(5-methoxy-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester (437650-81-2)

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

5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → 5-cyano-2,3-dihydro-1H-isoindole (263888-58-0)

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

5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → 5-methanesulfonyloxy-2,3-dihydro-1H-isoindole (263888-60-4)

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

5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → tert-butyl 5-hydroxyisoindoline-2-carboxylate (226070-47-9)

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

5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → tert-butyl 5-cyanoisoindoline-2-carboxylate (263888-56-8)

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

5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → 5-methanesulfonyloxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (263888-59-1)

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

5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → 4-[2-(5-methoxy-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclohexylamine (437651-98-4)

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

5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → 5-trifluoromethanesulfonyloxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (263888-57-9)

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

5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → 2-[2-(4-amino-cyclohexyl)-ethyl]-2,3-dihydro-1H-isoindole-5-carbonitrile (437652-04-5)

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

5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → methanesulfonic acid 2-[2-(4-amino-cyclohexyl)-ethyl]-2,3-dihydro-1H-isoindol-5-yl ester (437652-01-2)

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

5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → {4-[2-(5-cyano-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester (437651-10-0)

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

5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → methanesulfonic acid 2-[2-(4-tert-butoxycarbonylamino-cyclohexyl)-ethyl]-2,3-dihydro-1H-isoindol-5-yl ester (437650-82-3)

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

Upstream product

• 127168-86-9 4-NITROISOINDOLINE 
• 127168-84-7 5-BROMOISOINDOLINE 
• 127168-83-6 4-Bromo-2-tosylisoindoline ,97% 
• 127168-82-5 1-broMo-2,3-bis(broMoMethyl)benzene 
• 127168-81-4 3-Bromo-1H-isoindoline 
• 127168-78-9 1H-Isoindole, 4-fluoro-2,3-dihydro- 
• 127168-76-7 5-CHLOROISOINDOLINE HYDROCHLORIDE 
• 127168-73-4 4-METHOXYISOINDOLINE 
• 127168-70-1 2-BENZYL-2,3-DIHYDRO-1H-ISOINDOL-5-YLAMINE 
• 127168-68-7 2-Benzyl-5-nitroisoindoline 
• 1271-66-5 Bis(cyclopentadienyl)dimethyltitanium 
• 127166-41-0 sodium (11E)-11-[2-(5,6-dimethyl-1H-benzimidazol-1-yl)ethylidene]-6,11-dihydrodibenzo[b,e]oxepine-2-carboxylate 
• 1271660-32-2 (7-FLUORO-1H-INDOL-2-YL)METHANAMINE 
• 127165-18-8 (R)-(+)-8-METHOXY-2-AMINOTETRALIN 

Downstream Products

• 127168-89-2 B90102 
• 127168-90-5 Methyl isoindoline-4-carboxylate hydrochloride 
• 127168-91-6 Methyl 2,3-bis(broMoMethyl)benzoate 
• 127168-92-7 METHYL 2-BENZYLISOINDOLINE-4-CARBOXYLATE 
• 127168-93-8 METHYL ISOINDOLINE-5-CARBOXYLATE HYDROCHLORIDE 
• 127168-94-9 Methyl 2-benzylisoindoline-5-carboxylate 
• 127168-95-0 isoindolin-4-ylMethanol 
• 127168-98-3 ISOINDOLIN-5-YLMETHANOL 
• 127169-00-0 (2-BENZYLISOINDOLIN-4-YL)METHANAMINE 
• 127169-16-8 B90103 
• 127169-17-9 2-BENZYLISOINDOLINE-4-CARBOXYLICACID 
• 127169-82-8 8-Fluoro-2-Tetralone 
• 127170-73-4 2-hydroxy-3-(1H-imidazol-5-ylmethyl)benzamide hydrochloride (1:1) 
• 127170-74-5 2-hydroxy-3-(3H-imidazol-4-ylmethyl)-N-methyl-benzamide hydrochloride 

Recommend Products

• 127168-89-2  N-benzylisoindolin-5-yl methyl ether 
• 888724-82-1  1-(5-methoxyisoindolin-2-yl)-6-[4-(3-trifluoromethylphenyl)piperazin-1-yl]hexan-1-one 
• 888855-12-7  6-[4-(3-trifluoromethylphenyl)piperazin-1-yl]hexanoic acid 
• 905269-98-9  C₂₀H₂₀F₃NO₅S 
• 845616-82-2  5-methane-sulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid 
• 1620228-49-0  4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 5-methoxyisoindoline-2-carboxylate 
• 1620228-48-9  4-bromophenyl 5-methoxyisoindoline-2-carboxylate 
• 7693-44-9  4-bromophenyl chloroformate 
• 1453186-96-3  4-chloro-2-(methylsulfanyl)-8-(propan-2-yl)pyrazolo[1,5-a][1,3,5]triazine 
• 260046-09-1  (4-bromophenyl)(2-chloropyrimidin-4-yl)amine 
• 4685-47-6  3,4-dimethylanisole 
• 508237-23-8  5-(3,4-Dimethoxybenzylamino)-2-(2-furyl)-8-(5-methoxyisoindolin-2-ylmethyl)[1,2,4]triazolo[1,5-c]pyrimidine 
• 213896-16-3  5-(3,4-Dimethoxybenzylamino)-8-formyl-2-(furan-2-yl)[1,2,4]triazolo[1,5-c]pyrimidine