(S)-(-)-Indoline-2-carboxylic acid
- Product Name
- (S)-(-)-Indoline-2-carboxylic acid
- CAS No.
- 79815-20-6
- Chemical Name
- (S)-(-)-Indoline-2-carboxylic acid
- Synonyms
- Indoline-2-carboxylic acid;(R)-2,3-DIHYDRO-1H-INDOLE-2-CARBOXYLIC ACID;H-Idc-OH;H-L-Idc-OH;S)-(-)-Indoline-2-ca;Perindopril Impurity 48;Perindopril Impurity 46;Perindopril Impurity 40;Perindopril Intermediate;S-Indoline-2-Formic acid
- CBNumber
- CB2235455
- Molecular Formula
- C9H9NO2
- Formula Weight
- 163.17
- MOL File
- 79815-20-6.mol
(S)-(-)-Indoline-2-carboxylic acid Property
- Melting point:
- 177 °C (dec.)(lit.)
- alpha
- -112.5 º (c=1, 1N HCl)
- Boiling point:
- 290.25°C (rough estimate)
- Density
- 1.2021 (rough estimate)
- refractive index
- -116 ° (C=1, 2mol/L HCl)
- storage temp.
- Keep in dark place,Inert atmosphere,2-8°C
- Water Solubility
- Slightly soluble in water
- pka
- 2.04±0.20(Predicted)
- form
- Powder
- color
- Beige to brown
- optical activity
- [α]20/D 114°, c = 1 in 1 M HCl
- InChI
- InChI=1S/C9H9NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-4,8,10H,5H2,(H,11,12)/t8-/m0/s1
- InChIKey
- QNRXNRGSOJZINA-QMMMGPOBSA-N
- SMILES
- N1C2=C(C=CC=C2)C[C@H]1C(O)=O
- CAS DataBase Reference
- 79815-20-6(CAS DataBase Reference)
Safety
- Hazard Codes
- Xn
- Risk Statements
- 43-48/22-62
- Safety Statements
- 22-25-26-36/37
- WGK Germany
- 2
- HS Code
- 29339900
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H317May cause an allergic skin reaction
H373May cause damage to organs through prolonged or repeated exposure
- Precautionary statements
-
P202Do not handle until all safety precautions have been read and understood.
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P272Contaminated work clothing should not be allowed out of the workplace.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P308+P313IF exposed or concerned: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- 346802
- Product name
- (S)-(?)-Indoline-2-carboxylic acid
- Purity
- 99%
- Packaging
- 1g
- Price
- $68.8
- Updated
- 2025/07/31
- Product number
- 346802
- Product name
- (S)-(?)-Indoline-2-carboxylic acid
- Purity
- 99%
- Packaging
- 5g
- Price
- $219
- Updated
- 2025/07/31
- Product number
- I0395
- Product name
- (S)-(-)-Indoline-2-carboxylic Acid
- Purity
- >95.0%(T)
- Packaging
- 1g
- Price
- $27
- Updated
- 2025/07/31
- Product number
- I0395
- Product name
- (S)-(-)-Indoline-2-carboxylic Acid
- Purity
- >95.0%(T)
- Packaging
- 5g
- Price
- $80
- Updated
- 2025/07/31
- Product number
- I627213
- Product name
- (S)-(?)-Indoline-2-carboxylic acid
- Packaging
- 100mg
- Price
- $45
- Updated
- 2021/12/16
(S)-(-)-Indoline-2-carboxylic acid Chemical Properties,Usage,Production
Chemical Properties
white to light yellow crystal powde
Uses
Catalyst for enantioselective cyclopropanations.
Synthesis
42538-40-9
79815-20-6
Example 1 Synthesis of (S)-2,3-dihydro-1H-indole-2-carboxylic acid: In a 100 mL flask, 366 mg (1.5 mmol) of (S)-2-bromophenylalanine, 217 mg (1.6 mmol) of K2CO3, 3.2 mg (0.03 mmol) of CuCl, and 3.2 g of N-methyl pyrrolidone (NMP) were added in order. ). The reactor was flushed with argon and kept under a slow flow of argon. The reaction mixture was stirred and heated to 100 °C, which was maintained. Samples were taken periodically and analyzed by high performance liquid chromatography (HPLC). after 4 h, (S)-2-bromophenylalanine was completely converted to the target product. （The yield (in solution) of (S)-2,3-dihydro-1H-indole-2-carboxylic acid was 95.9% with an enantiomeric excess (ee) > 98.6%. Example 2 Synthesis of (S)-2,3-dihydro-1H-indole-2-carboxylic acid: 9.76 g (40.0 mmol) of (S)-2-bromophenylalanine, 5.80 g (42.0 mmol) of K2CO3, 40 mg (0.4 mmol) of CuCl, and 40 g of NMP were sequentially added to a flask at 80 °C. The reactor was flushed with argon and then kept under a slow flow of argon. The reaction mixture was stirred and heated to 80 °C, which was maintained. Samples were taken periodically and analyzed by HPLC. after 3.5 h, (S)-2-bromophenylalanine was completely converted. The reaction mixture was cooled to 25 °C, followed by the addition of 40 mL of water and 50 mL of ethyl acetate (EtOAc). The pH of the mixture was adjusted to 3.3 with 3.5 g of a 37% aqueous hydrochloric acid solution. after separation of the phases, the aqueous phase was extracted with 2 x 50 mL of EtOAc. The combined organic layers were washed with 25 mL of saturated aqueous sodium chloride and the organic phase was subsequently concentrated. The residue was dissolved in 16 mL of aqueous 5N hydrochloric acid, and the pH was adjusted to 2.1 with 9.4 g of 32% aqueous sodium hydroxide. the precipitated (S)-2,3-dihydro-1H-indole-2-carboxylic acid was separated by filtration and washed with 2 x 10 mL of water. After drying, 3.24 g (19.8 mmol) of (S)-2,3-dihydro-1H-indole-2-carboxylic acid was obtained in 49.5% yield, ee > 99%.
References
[1] Patent: EP1676838, 2006, A1. Location in patent: Page/Page column 16
[2] Patent: EP1676838, 2006, A1. Location in patent: Page/Page column 17
[3] Journal of Organic Chemistry, 2014, vol. 79, # 17, p. 7872 - 7879
[4] Patent: EP1676838, 2006, A1. Location in patent: Page/Page column 16-17
[5] Patent: WO2006/69799, 2006, A1. Location in patent: Page/Page column 28-29
(S)-(-)-Indoline-2-carboxylic acid Preparation Products And Raw materials
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View Lastest Price from (S)-(-)-Indoline-2-carboxylic acid manufacturers
- Product
- Perindopril Impurity 40 79815-20-6
- Price
- US $0.00-0.00/mg
- Min. Order
- 10mg
- Purity
- 98%
- Supply Ability
- 500mg
- Release date
- 2024-08-07
- Product
- Perindopril Impurity 46
- Price
- US $0.00-0.00/mg
- Min. Order
- 10mg
- Purity
- 98%
- Supply Ability
- 500mg
- Release date
- 2024-08-08
- Product
- (S) - (-) -Indoline-2-Carboxylic Acid 79815-20-6
- Price
- US $5.00-2.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10000kg
- Release date
- 2024-08-23