2-phenylindoline
- CasNo:26216-91-1
Product Description
Excellent chemical plant bulk supply 2-phenylindoline 26216-91-1
- Molecular Formula: C14H13N
- Molecular Weight: 195.264
- Vapor Pressure: 0.000171mmHg at 25°C
- Melting Point: 46 °C
- Refractive Index: 1.605
- Boiling Point: 330 °C at 760 mmHg
- PKA: 4.41±0.40(Predicted)
- Flash Point: 163.1 °C
- PSA： 12.03000
- Density: 1.092 g/cm3
- LogP: 3.53390
2-phenylindoline(Cas 26216-91-1) Usage
|
General Description |
2-Phenylindoline is a chiral auxiliary used in the asymmetric synthesis of iridoid derivatives, such as cis,cis-nepetalactol. It can be resolved into enantiomers via diastereomeric separation with (R)-(+)-α-methylbenzyl isocyanate and is synthesized by reducing 2-phenylindole. Its enantiomeric purity has been confirmed by chiral gas chromatography, demonstrating its utility in stereoselective reactions. |
InChI:InChI=1/C14H13N/c1-2-6-11(7-3-1)14-10-12-8-4-5-9-13(12)15-14/h1-9,14-15H,10H2
26216-91-1 Relevant articles
-
Shaw,Tyson
, p. 2538 (1956)
-
Mononuclear complexes of a tridentate redox-active ligand with sulfonamido groups: Structure, properties, and reactivity
Cook, Sarah A.,Bogart, Justin A.,Levi, Noam,Weitz, Andrew C.,Moore, Curtis,Rheingold, Arnold L.,Ziller, Joseph W.,Hendrich, Michael P.,Borovik
, p. 6540 - 6547 (2018)
The design of molecular complexes of ear...
Chemoenzymatic preparation of optically active secondary amines: a new efficient route to enantiomerically pure indolines
Gotor-Fernandez, Vicente,Fernandez-Torres, Pedro,Gotor, Vicente
, p. 2558 - 2564 (2006)
An efficient chemoenzymatic route for th...
Palladium-Catalyzed Direct and Specific C-7 Acylation of Indolines with 1,2-Diketones
Xie, Guilin,Zhao, Yuhan,Cai, Changqun,Deng, Guo-Jun,Gong, Hang
supporting information, p. 410 - 415 (2021/01/26)
The indole scaffold is a ubiquitous and ...
Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations
Liu, Shuyang,Tian, Miao,Bu, Xiubin,Tian, Hua,Yang, Xiaobo
supporting information, p. 7738 - 7744 (2021/05/07)
Photoactive two-dimensional covalent org...
Chiral Br?nsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles
Yang, Kai,Lou, Yixian,Wang, Chenglan,Qi, Liang-Wen,Fang, Tongchang,Zhang, Feng,Xu, Hetao,Zhou, Lu,Li, Wangyang,Zhang, Guan,Yu, Peiyuan,Song, Qiuling
supporting information, p. 3294 - 3299 (2020/01/21)
A new chiral Br?nsted acid, generated in...
Asymmetric Transfer Hydrogenation of N-Unprotected Indoles with Ammonia Borane
Zhao, Weiwei,Zhang, Zijia,Feng, Xiangqing,Yang, Jing,Du, Haifeng
supporting information, p. 5850 - 5854 (2020/08/05)
A metal-free asymmetric transfer hydroge...
26216-91-1 Process route
-
-
948-65-2
2-phenyl-indole
-
-
26216-91-1,917377-78-7
2-phenyl-2,3-dihydro-1H-indole
| Conditions | Yield |
|---|---|
|
With
hydrogenchloride; tin;
In
ethanol; water;
at 20 - 90 ℃;
for 4h;
Inert atmosphere;
|
94%
|
|
With
hydrogenchloride; tin;
In
ethanol; water;
at 90 ℃;
for 4h;
Inert atmosphere;
|
94%
|
|
With
hydrogenchloride; tin;
In
ethanol; water;
for 8h;
Reflux;
|
88%
|
|
With
hydrogenchloride; tin;
In
ethanol;
for 6h;
Heating;
|
87.1%
|
|
With
diphenyl phosphoryl azide; water; benzo[1,3,2]dioxaborole;
In
toluene;
at 20 ℃;
for 24h;
Inert atmosphere;
Schlenk technique;
|
87%
|
|
With
sodium cyanoborohydride; acetic acid;
at 20 ℃;
|
85%
|
|
With
hydrogenchloride; tin;
In
ethanol; water;
for 6h;
Reflux;
|
85%
|
|
With
sodium cyanoborohydride;
In
acetic acid;
at 20 ℃;
for 20h;
|
72%
|
|
With
ammonia borane; tris(pentafluorophenyl)borate;
In
toluene;
at 80 ℃;
for 8h;
Schlenk technique;
Inert atmosphere;
|
72%
|
|
With
sodium cyanoborohydride; acetic acid;
at 20 ℃;
for 20h;
|
70%
|
|
2-phenyl-indole;
With
(S)-2-methylpropane-2-sulfinamide; bis(pentafluorophenyl)borohydride;
In
cyclohexane;
at 30 ℃;
for 12h;
Sealed tube;
Inert atmosphere;
Glovebox;
With
borane-ammonia complex;
In
cyclohexane;
at 30 ℃;
for 48h;
Inert atmosphere;
Sealed tube;
Glovebox;
|
50%
|
|
2-phenyl-indole;
With
sodium cyanoborohydride; acetic acid;
at 0 - 20 ℃;
for 3h;
Inert atmosphere;
With
sodium hydrogencarbonate;
In
water;
pH=8 - 9;
|
16%
|
|
With
hydrogenchloride; ethanol; zinc;
|
|
|
With
hydrogenchloride; tin;
|
|
|
With
1,4-dioxane; copper oxide-chromium oxide;
at 150 ℃;
under 220652 Torr;
Hydrogenation;
|
|
|
With
sodium cyanoborohydride; acetic acid;
at 20 ℃;
for 8h;
|
|
|
With
hydrogenchloride; tin;
In
ethanol; water;
at 90 ℃;
for 4h;
Inert atmosphere;
|
|
|
With
sodium cyanoborohydride; acetic acid;
at 10 - 20 ℃;
for 3.5h;
|
|
|
With
sodium cyanoborohydride; acetic acid;
at 20 ℃;
for 20h;
|
|
|
With
sodium cyanoborohydride; acetic acid;
at 0 ℃;
for 12h;
|
|
|
With
sodium cyanoborohydride; acetic acid;
at 0 - 20 ℃;
for 4h;
|
-
-
164398-51-0
2-(2-Phenylethyl)phenyl azide
-
-
26216-91-1,917377-78-7
2-phenyl-2,3-dihydro-1H-indole
| Conditions | Yield |
|---|---|
|
With
C52H62FeN5O4S2(1-)*C8H20N(1+);
In
N,N-dimethyl-formamide;
at 115 ℃;
for 24h;
Molecular sieve;
|
96%
|
|
With
5,10,15,20-tetrakis(pentafluorophenyl)-21H,23H-porphyrin iron(III) chloride;
In
1,2-dichloro-ethane;
for 14h;
Molecular sieve;
Reflux;
Inert atmosphere;
|
80%
|
|
With
(Et4N)2[(Co(II)(μ2-N(o-PhNC(O)(i-Pr)-κN)2))2];
In
N,N-dimethyl-formamide; toluene;
at 110 ℃;
for 48h;
Reagent/catalyst;
Temperature;
Time;
Molecular sieve;
|
80%
|
|
With
tetrabutylammonium tricarbonylnitrosylferrate;
In
1,2-dichloro-ethane; N,N-dimethyl-formamide;
at 120 ℃;
for 1h;
Microwave irradiation;
Inert atmosphere;
|
72%
|
26216-91-1 Upstream products
-
948-65-2
2-phenyl-indole
-
67-56-1
methanol
-
164398-51-0
2-(2-Phenylethyl)phenyl azide
-
64-17-5
ethanol
26216-91-1 Downstream products
-
5697-85-8
2-(2-phenylethyl)aniline
-
948-65-2
2-phenyl-indole
-
3780-04-9
2-phenyl-indole-4,5-dione
-
1114822-30-8
2-phenyl-N-[(R)-1-phenylethyl]indoline-1-carboxamide