Product Name

  • Name

    (S)-(-)-Indoline-2-carboxylic acid

  • EINECS 410-860-2
  • CAS No. 79815-20-6
  • Article Data19
  • CAS DataBase
  • Density 1.286 g/cm3
  • Solubility Slightly soluble in water
  • Melting Point 177 °C (dec.)(lit.)
  • Formula C9H9NO2
  • Boiling Point 380 °C at 760 mmHg
  • Molecular Weight 163.176
  • Flash Point 183.6 °C
  • Transport Information
  • Appearance white to light yellow crystal powder
  • Safety 22-25-26-36/37
  • Risk Codes 43-48/22-62
  • Molecular Structure Molecular Structure of 79815-20-6 ((S)-(-)-Indoline-2-carboxylic acid)
  • Hazard Symbols HarmfulXn
  • Synonyms (S)-(-)-Indoline-2-carboxylic acid 79815-20-6;S-(-)-Indoline-2-carboxylic acid;(S)-(-) Indole-2-Carboxylic Acid;s-(-)- indoline- 2- carboxylic acid;S-Indoline-2-carboxylic acid;(S)-(-)-Indolene-2-Carboxylic Acid;S-(-)Indoline-2-carboxylic acid;(S)-Indoline-2-Carboxylic Acid;(S)-Indoline-2-formic acid;(-)-(S)-2-Indolinecarboxylic acid;(S)-(-)Indoline-2-CarboxylicAcid;(2S)-indoline-2-carboxylic acid;
  • PSA 49.33000
  • LogP 1.24580

Synthetic route

l-(S)-2,3-dihydro-1-[(S)-3-mercapto-2-methyl-1-oxopropyl]-1H-indole-2-carboxylic acid
78779-29-0

l-(S)-2,3-dihydro-1-[(S)-3-mercapto-2-methyl-1-oxopropyl]-1H-indole-2-carboxylic acid

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride for 3h; Heating;100%
(S)-2-amino-3-(2-bromophenyl)propanoic acid
42538-40-9

(S)-2-amino-3-(2-bromophenyl)propanoic acid

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate; copper(l) chloride In 1-methyl-pyrrolidin-2-one at 80 - 100℃; for 3.5 - 4h; Product distribution / selectivity;95.9%
With potassium carbonate In water at 95℃; for 22h; Product distribution / selectivity;95.6%
With potassium carbonate; copper(l) chloride In water at 95℃; for 1h; Inert atmosphere; enantioselective reaction;83%
(S)-indoline-2-carboxylic acid methyl ester
141410-06-2

(S)-indoline-2-carboxylic acid methyl ester

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (S)-indoline-2-carboxylic acid methyl ester With sodium hydroxide; water at 20℃;
Stage #2: With hydrogenchloride; water at 20℃; pH=5;		94.5%
Indole-2-carboxylic acid
1477-50-5

Indole-2-carboxylic acid

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
With carbon disulfide; carbon dioxide; hydrogen iodide; hydrogen; potassium iodide In ethanol at 90℃; for 5h; Temperature; Solvent; Autoclave; Large scale;87.5%
(S)-2,3-Dihydro-1H-indole-2-carboxylic acid tert-butyl ester; compound with formic acid

(S)-2,3-Dihydro-1H-indole-2-carboxylic acid tert-butyl ester; compound with formic acid

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran for 3h; Heating;87%
(S)-N-acetyl-2,3-dihydroindoline-2-carboxylic acid methyl ester
110592-39-7

(S)-N-acetyl-2,3-dihydroindoline-2-carboxylic acid methyl ester

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
With sulfuric acid; water Reflux;86.8%
(S)-o-bromophenylalanine hydrochloride

(S)-o-bromophenylalanine hydrochloride

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate; copper(I) bromide In water at 100 - 105℃; Inert atmosphere;86.2%
(2S)-2-amino-3-(2-chlorophenyl)propanoic acid
103616-89-3

(2S)-2-amino-3-(2-chlorophenyl)propanoic acid

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate; copper(l) chloride In water at 95℃; for 40h; Product distribution / selectivity;76.6%
Stage #1: (2S)-2-amino-3-(2-chlorophenyl)propanoic acid With potassium carbonate; copper(l) chloride In water at 95℃; for 40h;
Stage #2: With water at 25℃; pH=3.5; Product distribution / selectivity; Acidic conditions;		76.6%
(2S)-indoline-2-carboxylic acid (R)-α-methylbenzylamine salt
79854-38-9

(2S)-indoline-2-carboxylic acid (R)-α-methylbenzylamine salt

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In water for 2h; Product distribution / selectivity;52.8%
1-acetyl-2,3-indoline-2-carboxylic acid
82950-72-9

1-acetyl-2,3-indoline-2-carboxylic acid

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride
1-benzhydryl-2,3-dihydro-1H-indole-2-carboxylic acid tert-butyl ester
496790-47-7

1-benzhydryl-2,3-dihydro-1H-indole-2-carboxylic acid tert-butyl ester

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 77 percent / H2 / Pd/C / methanol / 48 h / 5171.62 Torr
2: 87 percent / aq. HCl / tetrahydrofuran / 3 h / Heating
View Scheme
2-(benzhydrylidene-amino)-3-(2-bromo-phenyl)-propionic acid tert-butyl ester
496790-43-3

2-(benzhydrylidene-amino)-3-(2-bromo-phenyl)-propionic acid tert-butyl ester

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 69 percent / nBu3SnH; AIBN / benzene / 5 h / 85 °C
2: 77 percent / H2 / Pd/C / methanol / 48 h / 5171.62 Torr
3: 87 percent / aq. HCl / tetrahydrofuran / 3 h / Heating
View Scheme
1-Bromo-2-bromomethyl-benzene
3433-80-5

1-Bromo-2-bromomethyl-benzene

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: CsOH*H2O / cinchonine bromide derived chiral / 20 h
2: 69 percent / nBu3SnH; AIBN / benzene / 5 h / 85 °C
3: 77 percent / H2 / Pd/C / methanol / 48 h / 5171.62 Torr
4: 87 percent / aq. HCl / tetrahydrofuran / 3 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 89 percent / CsOH*H2O / cinchonidinium bromide derived chiral / 20 h
2: 69 percent / nBu3SnH; AIBN / benzene / 5 h / 85 °C
3: 77 percent / H2 / Pd/C / methanol / 48 h / 5171.62 Torr
4: 87 percent / aq. HCl / tetrahydrofuran / 3 h / Heating
View Scheme
N-acetyl-indoline-2-carboxylic acid methyl ester
110659-07-9

N-acetyl-indoline-2-carboxylic acid methyl ester

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 43 percent
2: aq. 2N HCl
View Scheme
indolin-2-yl carboxylic acid
16851-56-2

indolin-2-yl carboxylic acid

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 52 percent / Et3N / CH2Cl2 / 2.75 h / 0 - 20 °C
3: 1.) 4-(dimethylamino)pyridine
5: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C
6: 100 percent / 6 N HCl / 3 h / Heating
View Scheme
(S)-2,3-dihydro-1H-indole-2-carboxylic acid,ethyl ester
50501-07-0

(S)-2,3-dihydro-1H-indole-2-carboxylic acid,ethyl ester

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 100 percent / KOH / dimethylsulfoxide; H2O / Ambient temperature
2: 52 percent / Et3N / CH2Cl2 / 2.75 h / 0 - 20 °C
4: 1.) 4-(dimethylamino)pyridine
6: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C
7: 100 percent / 6 N HCl / 3 h / Heating
View Scheme
Multi-step reaction with 7 steps
1: 100 percent / Et3N / diethyl ether / 4 h / Ambient temperature
2: 95 percent / NaOH / methanol; H2O / 1 h / Ambient temperature
4: 1.) 4-(dimethylamino)pyridine
6: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C
7: 100 percent / 6 N HCl / 3 h / Heating
View Scheme
2,3-dihydro-1-(2-methyl-1-oxo-2-propenyl)-1H-indole-2-carboxylic acid ethyl ester
78701-23-2

2,3-dihydro-1-(2-methyl-1-oxo-2-propenyl)-1H-indole-2-carboxylic acid ethyl ester

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 95 percent / NaOH / methanol; H2O / 1 h / Ambient temperature
3: 1.) 4-(dimethylamino)pyridine
5: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C
6: 100 percent / 6 N HCl / 3 h / Heating
View Scheme
2,3-Dihydro-1-(2-methyl-1-oxo-2-propenyl)-1H-indole-2-carboxylic acid
78701-24-3

2,3-Dihydro-1-(2-methyl-1-oxo-2-propenyl)-1H-indole-2-carboxylic acid

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
2: 1.) 4-(dimethylamino)pyridine
4: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C
5: 100 percent / 6 N HCl / 3 h / Heating
View Scheme
(-)-1-(2-methyl-1-oxo-2-propenyl)indoline-2-carboxylic acid
78701-38-9

(-)-1-(2-methyl-1-oxo-2-propenyl)indoline-2-carboxylic acid

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) 4-(dimethylamino)pyridine
3: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C
4: 100 percent / 6 N HCl / 3 h / Heating
View Scheme
(S)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>indoline-2-carboxylic acid
78701-25-4, 78701-28-7, 78779-25-6, 78779-26-7, 78779-27-8, 78779-28-9, 106517-52-6

(S)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>indoline-2-carboxylic acid

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C
3: 100 percent / 6 N HCl / 3 h / Heating
View Scheme
Wy-44,088
78779-25-6

Wy-44,088

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C
2: 100 percent / 6 N HCl / 3 h / Heating
View Scheme
indoline-2-carboxylic acid (R)-α-methylbenzylamine salt

indoline-2-carboxylic acid (R)-α-methylbenzylamine salt

A

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

B

(R)-(-)-2,3-Dihydro-1H-Indole-2-Carboxylic Acid
98167-06-7

(R)-(-)-2,3-Dihydro-1H-Indole-2-Carboxylic Acid

Conditions
ConditionsYield
With hydrogenchloride In water for 2h;
(S)-indoline-2-carboxylic acid (1S)-10-camphorsulfonic acid salt
887769-80-4

(S)-indoline-2-carboxylic acid (1S)-10-camphorsulfonic acid salt

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 0 - 5℃; pH=2.9;
(+)-α-Chloro-2-aminobenzenepropanoic acid, 2,6-dimethylpiperidine salt
104145-74-6, 106025-43-8, 106025-50-7

(+)-α-Chloro-2-aminobenzenepropanoic acid, 2,6-dimethylpiperidine salt

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
With phosphorus pentaoxide; sodium hydroxide
C9H9NO2*C17H17Cl2N
880872-40-2

C9H9NO2*C17H17Cl2N

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: C9H9NO2*C17H17Cl2N With sodium hydroxide In water; ethyl acetate pH=> 10;
Stage #2: With hydrogenchloride In water pH=4 - 5;
6-amino-(S)-indoline-2-carboxylic acid
1344514-62-0

6-amino-(S)-indoline-2-carboxylic acid

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 6-amino-(S)-indoline-2-carboxylic acid With hydrogenchloride In water at 0℃; for 0.5h;
Stage #2: With sodium nitrite In water for 1h;
Stage #3: With ethanol In water at 55℃; for 3h;		7 g
4-nitro-3-phenyl-L-alanine
949-99-5

4-nitro-3-phenyl-L-alanine

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sulfuric acid; uronium nitrate / 5 h / 0 - 60 °C
2.1: oxygen; potassium carbonate / water / 5 h / 120 °C / 3000.3 Torr / Autoclave
3.1: 5%-palladium/activated carbon; hydrogen / water / 4 h / 60 °C / 3750.38 Torr / Autoclave
4.1: hydrogenchloride / water / 0.5 h / 0 °C
4.2: 1 h
4.3: 3 h / 55 °C
View Scheme
ethanol
64-17-5

ethanol

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

Ethyl (S)-indoline-2-carboxylate hydrochloride
79854-42-5

Ethyl (S)-indoline-2-carboxylate hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; for 16h;100%
With thionyl chloride In ethanol at 0 - 20℃; for 16h;100%
With thionyl chloride at 0 - 20℃; for 16h;100%
With thionyl chloride
methanol
67-56-1

methanol

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

(S)-indoline-2-carboxylic acid methyl ester hydrochloride

(S)-indoline-2-carboxylic acid methyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃;100%
With thionyl chloride at -10 - 20℃;99%
With thionyl chloride at 20℃; for 53h; Esterification;99%
methanol
67-56-1

methanol

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

(S)-indoline-2-carboxylic acid methyl ester
141410-06-2

(S)-indoline-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With thionyl chloride at 40℃; for 3h;99%
With sulfuric acid at 80℃; for 16h;89.01%
With thionyl chloride at 0 - 70℃; for 16h; Cooling with ice;82%
(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

benzyl chloroformate
501-53-1

benzyl chloroformate

(S)-1-(benzyloxycarbonyl)indoline-2-carboxylic acid
104261-79-2

(S)-1-(benzyloxycarbonyl)indoline-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide at 0℃; for 1h;99%
With sodium hydrogencarbonate In water; toluene Ambient temperature;96%
With sodium hydroxide at 5 - 20℃; for 5h;93%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

(S)-N-tert-butoxycarbonylindoline-2-carboxylic acid
144069-67-0

(S)-N-tert-butoxycarbonylindoline-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 20℃; for 12h;98%
With sodium carbonate In tert-butyl alcohol at 20℃; for 12h;96%
With sodium hydroxide In 1,4-dioxane at 0 - 20℃;90%
(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

(2S)-2,3-dihydro-1H-indole-2-ylmethanol
27640-33-1

(2S)-2,3-dihydro-1H-indole-2-ylmethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether Inert atmosphere;96%
Stage #1: (S)-indoline-2-carboxylic acid With dimethylsulfide borane complex; boron trifluoride diethyl etherate In tetrahydrofuran Reflux;
Stage #2: With hydrogenchloride; methanol; water In tetrahydrofuran Reflux;
Stage #3: With sodium hydroxide In water		87%
Stage #1: (S)-indoline-2-carboxylic acid With dimethylsulfide borane complex In tetrahydrofuran for 12h; Reflux;
Stage #2: With hydrogenchloride In tetrahydrofuran; methanol for 2h; Reflux;
Stage #3: With sodium hydroxide In tetrahydrofuran; methanol; water		87%
ethanol
64-17-5

ethanol

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

(S)-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester
82923-81-7

(S)-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With thionyl chloride95%
With thionyl chloride at 0 - 20℃; for 16h;
(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

methyl iodide
74-88-4

methyl iodide

(2S)-1-methylindoline-2-carboxylic methyl ester
502435-12-3

(2S)-1-methylindoline-2-carboxylic methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone at 50℃; for 24h; Inert atmosphere;95%
With potassium carbonate In DMF (N,N-dimethyl-formamide); acetone at 20℃;
(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

(6a,7,13a,14)-tetrahydropyrazino[1,2-a:4,5-a']diindol-6,13-dione
50501-06-9

(6a,7,13a,14)-tetrahydropyrazino[1,2-a:4,5-a']diindol-6,13-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 220℃; under 12901.3 Torr; for 0.416667h; Microwave irradiation;94%
(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

(6aS-cis)-6a,7,13a,14-tetrahydropyrazino<1,2-a:4,5-a'>diindole-6,13-dione
104321-36-0

(6aS-cis)-6a,7,13a,14-tetrahydropyrazino<1,2-a:4,5-a'>diindole-6,13-dione

Conditions
ConditionsYield
With methyl dichlorophosphite; triethylamine; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In toluene at 145℃; for 1h; Microwave irradiation; stereoselective reaction;93%
With methyl dichlorophosphite; triethylamine; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In toluene at 145℃; for 1h; Microwave irradiation;93%
With triethylamine In toluene for 5h; Heating;83%
With dicyclohexyl-carbodiimide In tetrahydrofuran for 1h; Ambient temperature;76%
With dicyclohexyl-carbodiimide In tetrahydrofuran for 1h; Ambient temperature;76%
(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

C33H27NO2P2

C33H27NO2P2

Conditions
ConditionsYield
With triethylamine In diethyl ether for 24h;93%
sarcosine
107-97-1

sarcosine

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

(S)-2-methyl-2,3,10,10a-tetrahydropyrazino[1,2-a]indole-1,4-dione
1110659-50-1

(S)-2-methyl-2,3,10,10a-tetrahydropyrazino[1,2-a]indole-1,4-dione

Conditions
ConditionsYield
With methyl dichlorophosphite; triethylamine; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In toluene at 145℃; for 1h; Microwave irradiation; stereoselective reaction;93%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

methyl (S)-N-(tert-butoxycarbonyl)indoline-2-carboxylate
197460-36-9

methyl (S)-N-(tert-butoxycarbonyl)indoline-2-carboxylate

Conditions
ConditionsYield
Stage #1: (S)-indoline-2-carboxylic acid With thionyl chloride In methanol Inert atmosphere;
Stage #2: di-tert-butyl dicarbonate With triethylamine Inert atmosphere;		91%
With thionyl chloride; triethylamine 1.) MeOH, -10 deg C, 0.5 h; reflux, 3 h, 2.) CH2Cl2, room temperature, 24 h; Yield given. Multistep reaction;
trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

3-phenyl-propenal
104-55-2

3-phenyl-propenal

CF3O3S(1-)*C18H16NO2(1+)

CF3O3S(1-)*C18H16NO2(1+)

Conditions
ConditionsYield
Stage #1: (S)-indoline-2-carboxylic acid; 3-phenyl-propenal In methanol at 20℃; for 0.0333333h;
Stage #2: trifluorormethanesulfonic acid In methanol		91%
...Expand
(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

(R)-(-)-2,3-Dihydro-1H-Indole-2-Carboxylic Acid
98167-06-7

(R)-(-)-2,3-Dihydro-1H-Indole-2-Carboxylic Acid

indolin-2-yl carboxylic acid
16851-56-2

indolin-2-yl carboxylic acid

Conditions
ConditionsYield
Stage #1: (S)-indoline-2-carboxylic acid; (R)-(-)-2,3-Dihydro-1H-Indole-2-Carboxylic Acid With sodium hydroxide In water at 170℃; under 5250.53 Torr; for 3h; Racemisation;
Stage #2: With hydrogenchloride In water at 20 - 25℃; pH=3.4;		90%
(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

(2S,3aS,7aS)-perhydroindole-2-carboxylic acid
80875-98-5

(2S,3aS,7aS)-perhydroindole-2-carboxylic acid

Conditions
ConditionsYield
rhodium In 1,4-dioxane; methanol; water86.1%
With 8 % Pd/C; hydrogen In methanol at 55 - 65℃; under 37503.8 Torr; Autoclave;73.5%
With hydrogen; palladium on activated charcoal In acetic acid at 50℃; under 36775.4 Torr; for 18h;66%
(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

A

(2S,3aS,7aS)-perhydroindole-2-carboxylic acid
80875-98-5

(2S,3aS,7aS)-perhydroindole-2-carboxylic acid

B

(2S,3aR,7aR)-octahydroindole-2-carboxylic acid
145513-90-2

(2S,3aR,7aR)-octahydroindole-2-carboxylic acid

Conditions
ConditionsYield
With hydrogen; acetic acid; platinum(IV) oxide at 60℃; for 24h; atmospheric pressure;A 85%
B n/a
With platinum(IV) oxide; hydrogen at 60℃; optical yield given as %de;A 85%
B n/a
acetic anhydride
108-24-7

acetic anhydride

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

1-acetyl-2,3-indoline-2-carboxylic acid
82950-72-9

1-acetyl-2,3-indoline-2-carboxylic acid

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 16h;85%
(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

L-proline
147-85-3

L-proline

(5aS,12aS)-1,2,3,5a,6,12a-hexahydro-5H,12H-pyrrolo[1',2':4,5]pyrazino[1,2-a]indole-5,12-dione
104261-77-0

(5aS,12aS)-1,2,3,5a,6,12a-hexahydro-5H,12H-pyrrolo[1',2':4,5]pyrazino[1,2-a]indole-5,12-dione

Conditions
ConditionsYield
With methyl dichlorophosphite; triethylamine; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In toluene at 145℃; for 1h; Microwave irradiation; stereoselective reaction;83%
(2S,3aS,7aS)-perhydroindole-2-carboxylic acid
80875-98-5

(2S,3aS,7aS)-perhydroindole-2-carboxylic acid

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

(4aS,6aS,13aS,14aS)-1,2,3,4,4a,6a,7,13a,14,14a-decahydro-6H,13H-pyrazino[1,2-a:4,5-a']diindole-6,13-dione
1110659-49-8

(4aS,6aS,13aS,14aS)-1,2,3,4,4a,6a,7,13a,14,14a-decahydro-6H,13H-pyrazino[1,2-a:4,5-a']diindole-6,13-dione

Conditions
ConditionsYield
With methyl dichlorophosphite; triethylamine; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In toluene at 145℃; for 1h; Microwave irradiation; stereoselective reaction;81%
L-N-Boc-Ala
15761-38-3

L-N-Boc-Ala

(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

methyl (2S)-1-{(2S)-2-[(tert-butyloxycarbonyl)-amino]-propionyl}-2,3-dihydro-1H-indole-2-carboxylate

methyl (2S)-1-{(2S)-2-[(tert-butyloxycarbonyl)-amino]-propionyl}-2,3-dihydro-1H-indole-2-carboxylate

Conditions
ConditionsYield
Stage #1: (S)-indoline-2-carboxylic acid With triethylamine In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: L-N-Boc-Ala With dicyclohexyl-carbodiimide at 20℃; for 6h;		81%
(S)-indoline-2-carboxylic acid
79815-20-6

(S)-indoline-2-carboxylic acid

A

Cbz-D-HPro-Ohi-OH

Cbz-D-HPro-Ohi-OH

B

Ethyl (S)-indoline-2-carboxylate hydrochloride
79854-42-5

Ethyl (S)-indoline-2-carboxylate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanolA n/a
B 78%
With hydrogenchloride In ethanolA n/a
B 78%
With hydrogenchloride In ethanolA n/a
B 78%
With hydrogenchloride In ethanolA n/a
B 78%
With hydrogenchloride In ethanolA n/a
B 78%

(S)-(-)-Indoline-2-carboxylic acid Chemical Properties

The Molecular Structure of (S)-(-)-Indoline-2-carboxylic acid (CAS NO.79815-20-6):

Empirical Formula: C9H9NO2
Molecular Weight: 163.1733
Appearance: white to light yellow crystal powder
 Nominal Mass: 163 Da
Average Mass: 163.1733 Da
Monoisotopic Mass: 163.063329 Da 
Index of Refraction: 1.598
Molar Refractivity: 43.27 cm3
Molar Volume: 126.8 cm3
Surface Tension: 52.2 dyne/cm
Density: 1.286 g/cm3
Flash Point: 183.6 °C
Enthalpy of Vaporization: 66.26 kJ/mol
Boiling Point: 380 °C at 760 mmHg
Vapour Pressure: 1.88E-06 mmHg at 25°C 
Refractive index: -116 ° (C=1, 2mol/L HCl)
Storage temp: Store at 0°C
Product Categories: PYRROLE;Indoles and derivatives;pharmacetical;chiral;PERINDOPRIL;(intermediate of perindopril);Indoles;Chiral Compound;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;Proline-Based Organocatalysts

(S)-(-)-Indoline-2-carboxylic acid Uses

 (S)-(-)-Indoline-2-carboxylic acid (CAS NO.79815-20-6) is mainly used in the treatment of cardiovascular and cerebrovascular diseases.

(S)-(-)-Indoline-2-carboxylic acid Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 43-48/22-62 
R43: May cause sensitization by skin contact
R48/22: Harmful: danger of serious damage to health by prolonged exposure if swallowed
R62: Risk of impaired fertility
Safety Statements: 22-25-26-36/37 
S22: Do not breathe dust
S25: Avoid contact with eyes
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37: Wear suitable protective clothing and gloves
WGK Germany: 2

(S)-(-)-Indoline-2-carboxylic acid Specification

 (S)-(-)-Indoline-2-carboxylic acid (CAS NO.79815-20-6) is also called as (R)-1h-indole-2-carboxylic acid ; (R)-2,3-dihydro-1h-indole-2-carboxylic acid ; (R)-(+)-2,3-dihydroindole-2-carboxylic acid ; Perindopril intermediate ; (2S)-indoline-2-carboxylic acid ; (2S)-2,3-dihydro-1h-indole-2-carboxylic acid ; (S)-(-)-indoline-2-carboxylicacid98% .

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