| Identification | More | [Name]
Indoline | [CAS]
496-15-1 | [Synonyms]
2,3-DIHYDRO-1H-INDOLE
2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE
2,3-DIHYDROINDOLE
IDN
INDOLINE
LABOTEST-BB LT01605668
TIMTEC-BB SBB004291
1-Azaindan
2,3-dihydro-1h-indol
Dihydroindole
Indoline.2.3-Dihydroindole
2,3-Dichloro-1H-Indole
Indoline,98%
1H-Indole, 2,3-dihydro-
Indoline ,97% | [EINECS(EC#)]
207-816-8 | [Molecular Formula]
C8H9N | [MDL Number]
MFCD00005705 | [Molecular Weight]
119.16 | [MOL File]
496-15-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless to slightly brown liquid | [Melting point ]
-21 °C
| [Boiling point ]
220-221 °C (lit.) | [density ]
1.063 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.592(lit.)
| [Fp ]
199 °F
| [storage temp. ]
2-8°C | [solubility ]
5g/l | [form ]
liquid (clear)
| [pka]
5.20±0.20(Predicted) | [color ]
clear dark brown
| [Odor]
a mild, delicate, but extremely tenacious floral odor | [Water Solubility ]
5 g/L (20 ºC) | [Sensitive ]
Light Sensitive | [Detection Methods]
GC | [BRN ]
111915 | [CAS DataBase Reference]
496-15-1(CAS DataBase Reference) | [NIST Chemistry Reference]
1H-Indole, 2,3-dihydro-(496-15-1) | [EPA Substance Registry System]
496-15-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3 | [RTECS ]
NL6906300 | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29339990 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless to slightly brown liquid | [Uses]
As an indole derivative, Indoline can be used in the preparation of various medicinal compounds such as potential α1-adrenoceptor (α1-AR) antagonists.
| [Application]
In organic chemistry, indoline derivatives are widely used as chiral auxiliary groups or chiral ligands, playing a crucial role in asymmetric synthesis. For example, (S)-Indoline-2-methanol is an important starting material for the synthesis of many chiral compounds. Through asymmetric catalytic reactions, such as the asymmetric rearrangement reaction of iridium porphyrin-catalyzed indoles with aryl diazonium esters, chiral 2-indoline tertiary alcohols can be synthesized efficiently. | [Definition]
ChEBI: Indoline is a member of indoles. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 96, p. 7812, 1974 DOI: 10.1021/ja00832a035
Synthetic Communications, 13, p. 489, 1983 DOI: 10.1080/00397918308081827 | [Synthesis]
Indolene is manufactured from (theoretically) 2 Mol. Indole plus 1 Mol. Hydroxycitronellal by condensation under heating. The proportions may vary slightly, and it is common practice to add Diethyl phthalate to the mixture prior to heating, so that the condensation product is somewhat protected against local overheating, and the finished product becomes light of color and fairly pourable at room temperature. |
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