[ CAS No. 115661-82-0 ] {[proInfo.proName]}

Name: 115661-82-0|Indoline-7-carbonitrile|98%
Brand: Ambeed
SKU: A113412
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Quality Control of [ 115661-82-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 115661-82-0 ]

SDS Specification

Alternatived Products of [ 115661-82-0 ]

Product Details of [ 115661-82-0 ]

CAS No. :	115661-82-0	MDL No. :	MFCD01830669
Formula :	C₉H₈N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YABRSQUYXZGQBW-UHFFFAOYSA-N
M.W :	144.17	Pubchem ID :	4188047
Synonyms :

Calculated chemistry of [ 115661-82-0 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.25
TPSA :	35.82 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.0 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.64
Log Po/w (XLOGP3) :	1.66
Log Po/w (WLOGP) :	0.95
Log Po/w (MLOGP) :	1.05
Log Po/w (SILICOS-IT) :	2.15
Consensus Log Po/w :	1.49

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.18
Solubility :	0.945 mg/ml ; 0.00656 mol/l
Class :	Soluble
Log S (Ali) :	-2.03
Solubility :	1.36 mg/ml ; 0.00942 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.06
Solubility :	0.125 mg/ml ; 0.000867 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.49

Safety of [ 115661-82-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 115661-82-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 115661-82-0 ]
Downstream synthetic route of [ 115661-82-0 ]

[ 115661-82-0 ] Synthesis Path-Upstream 1~2

1
[ 496-15-1 ]
[ 545-06-2 ]
[ 115661-82-0 ]

Yield	Reaction Conditions	Operation in experiment
60.5%	With BCl₃ In methanol; hexane; pentan-1-ol; water; toluene	(a) Production of 7-cyanoindoline 22 g of BCl₃ (187.8 mmol) in 120 ml of toluene (dried) was dissolved in a 750 ml round flask at -20°. 15.9 g of indoline (133.4 mmol) in 100 ml of toluene was added within 25 minutes and the temperature rose to 10°. This suspension was refluxed for 1 hour, then 110 ml of toluene was distilled off and the reaction mixture was cooled to 55° C. Then 38.4 g of trichloroacetonitrile (266 mmol) was added within 20 minutes and the resulting red solution was stirred for 20 hours at 60° C. After addition of methanol (110 ml) the reaction mixture was mixed within 1.5 hours with 60 g of a 30 percent methanolic sodium methanolate solution. After 1 hour of stirring the methanol was distilled off in a vacuum and then toluene (300 ml) and water (300 ml) were added. The aqueous phase was extracted several times with 200 ml of toluene. The combined toluene extracts were then washed with a 0.12N HCl (91 ml) and with water to remove the not reacted indoline. After concentration by evaporation of toluene 20.12 g of a brownish oil was obtained. The latter was then recrystallized in a hexane/pentanol mixture (80 ml; mixture ratio of hexane: pentanol=9:7) to obtain 11.47 g of a light brownish product with a purity of 99.4 percent corresponding to a yield of 60.5 percent relative to feedstock used. Other data concerning the product was: ¹ H-NMR (CDCl₃) δ in ppm: 3.08, t; 3.70, t; 4.53 bs, 6.61, t; 7.13, d; 7.18, d.

Reference： [1] Patent: US5380857, 1995, A,

2
[ 496-15-1 ]
[ 545-06-2 ]
[ 115661-82-0 ]

Yield	Reaction Conditions	Operation in experiment
58%	With boron trichloride; potassium carbonate In methanol; dichloromethane; toluene	EXAMPLE 73 To a solution of 1.19 g of indoline in 10 ml of toluene was added 5.5 ml of a solution of 2.02M of boron trichloride in toluene under ice-cooling, and the mixture was refluxed on an oil bath for 1 hr. and evaporated under atmospheric pressure to remove the solvent. The residue was mixed with 2 ml of trichloroacetonitrile and heated at 60°-62° C. on an oil bath for 20 hr. The product was dissolved in 20 ml of methylene chloride and poured into a mixture of 9.1 g of potassium carbonate and 40 ml of methanol under ice-cooling. The mixture was refluxed on an oil bath for 1 hr. and filtered to remove the insoluble material. The filtrate was evaporated and partitioned between water and methylene chloride. The methylene chloride layer was washed with dilute HCl, dried over anhydrous magnesium sulfate and evaporated to dry- ness. The residue (1.10 g) was purified on a Lobar column and the product (0.913 g) from the methylene chloride elude was recrystallized from ether-hexane to give 0.836 g of 7-cyanoindoline as crystals melting at 66°-67° C. Yield: 58percent Anal Calcd (percent) for C₉ H₈ N₂: C, 74.97; H, 5.59; N, 19.43; Found (percent): C, 74.98; H, 5.60; N, 19.51. IR (CHCl₃): 3432, 2217 cm^-1.

Reference： [1] Patent: US4774331, 1988, A,

[ 115661-82-0 ] Synthesis Path-Downstream 1~16

1
[ 496-15-1 ]
methanolic sodium methanolate [ No CAS ]
[ 545-06-2 ]
[ 115661-82-0 ]

Yield	Reaction Conditions	Operation in experiment
60.5%	With BCl3; In methanol; hexane; pentan-1-ol; water; toluene;	(a) Production of 7-cyanoindoline 22 g of BCl3 (187.8 mmol) in 120 ml of toluene (dried) was dissolved in a 750 ml round flask at -20. 15.9 g of indoline (133.4 mmol) in 100 ml of toluene was added within 25 minutes and the temperature rose to 10. This suspension was refluxed for 1 hour, then 110 ml of toluene was distilled off and the reaction mixture was cooled to 55 C. Then 38.4 g of trichloroacetonitrile (266 mmol) was added within 20 minutes and the resulting red solution was stirred for 20 hours at 60 C. After addition of methanol (110 ml) the reaction mixture was mixed within 1.5 hours with 60 g of a 30 percent methanolic sodium methanolate solution. After 1 hour of stirring the methanol was distilled off in a vacuum and then toluene (300 ml) and water (300 ml) were added. The aqueous phase was extracted several times with 200 ml of toluene. The combined toluene extracts were then washed with a 0.12N HCl (91 ml) and with water to remove the not reacted indoline. After concentration by evaporation of toluene 20.12 g of a brownish oil was obtained. The latter was then recrystallized in a hexane/pentanol mixture (80 ml; mixture ratio of hexane: pentanol=9:7) to obtain 11.47 g of a light brownish product with a purity of 99.4 percent corresponding to a yield of 60.5 percent relative to feedstock used. Other data concerning the product was: 1 H-NMR (CDCl3) delta in ppm: 3.08, t; 3.70, t; 4.53 bs, 6.61, t; 7.13, d; 7.18, d.

Reference： [1]Patent: US5380857,1995,A

2
[ 115661-82-0 ]
[ 15861-40-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid;	PREPARATION 12 A mixture of <strong>[115661-82-0]7-cyanoindoline</strong> (4.32 g) and 50% aqueous sulfuric acid (40 ml) was stirred at 110-120 C. for 5.5 hours, cooled to 5 C. and adjusted to pH 7-8 with 24% aqueous sodium hydroxide. The mixture was washed with ethyl acetate and the aqueous layer was adjusted to pH 2.5-3.0 with 6N hydrochloric acid. The precipitates were collected by filtration to give indoline-7-carboxylic acid (3.25 g). IR (Nujol): 3420, 2600, 1650, 1605, 1590 cm-1. NMR (CDCl3, delta): 3.07 (2H, tri, J=18 Hz), 3.74 (2H, tri, J=18 Hz), 6.53-6.60 (1H, m), 7.17-7.25 (1H, m), 7.59-7.63(1H,m).

Reference： [1]Patent: US4981847,1991,A

3
[ 496-15-1 ]
[ 545-06-2 ]
[ 115661-82-0 ]

Yield	Reaction Conditions	Operation in experiment
58%	With boron trichloride; potassium carbonate; In methanol; dichloromethane; toluene;	EXAMPLE 73 To a solution of 1.19 g of indoline in 10 ml of toluene was added 5.5 ml of a solution of 2.02M of boron trichloride in toluene under ice-cooling, and the mixture was refluxed on an oil bath for 1 hr. and evaporated under atmospheric pressure to remove the solvent. The residue was mixed with 2 ml of trichloroacetonitrile and heated at 60-62 C. on an oil bath for 20 hr. The product was dissolved in 20 ml of methylene chloride and poured into a mixture of 9.1 g of potassium carbonate and 40 ml of methanol under ice-cooling. The mixture was refluxed on an oil bath for 1 hr. and filtered to remove the insoluble material. The filtrate was evaporated and partitioned between water and methylene chloride. The methylene chloride layer was washed with dilute HCl, dried over anhydrous magnesium sulfate and evaporated to dry- ness. The residue (1.10 g) was purified on a Lobar column and the product (0.913 g) from the methylene chloride elude was recrystallized from ether-hexane to give 0.836 g of 7-cyanoindoline as crystals melting at 66-67 C. Yield: 58% Anal Calcd (%) for C9 H8 N2: C, 74.97; H, 5.59; N, 19.43; Found (%): C, 74.98; H, 5.60; N, 19.51. IR (CHCl3): 3432, 2217 cm-1.

Reference： [1]Patent: US4774331,1988,A

4
[ 115661-82-0 ]
[ 1269801-81-1 ]

Reference： [1]Patent: WO2011/30356,2011,A2
[2]Patent: US2012/165548,2012,A1

5
[ 115661-82-0 ]
[ 1269801-83-3 ]

Reference： [1]Patent: WO2011/30356,2011,A2
[2]Patent: US2012/165548,2012,A1

6
[ 115661-82-0 ]
[ 1269801-84-4 ]

Reference： [1]Patent: WO2011/30356,2011,A2
[2]Patent: US2012/165548,2012,A1

7
[ 115661-82-0 ]
[ 1269801-85-5 ]

Reference： [1]Patent: WO2011/30356,2011,A2
[2]Patent: US2012/165548,2012,A1

8
[ 115661-82-0 ]
[ 115306-83-7 ]
[ 1269801-75-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 70.0℃;	Reference Example 1 Preparation of 1-[3-(t-Butyl-dimethyl-silanyIoxy)-propyl]-2,3-dihydro-1H-indole-7-carbonitrile (II) A mixture of 7-Cyano indoline (5 g, 0.035 mole), dimethyl formamide (50 ml) and powdered K2C03 (9.6 g, 0.07 mole) was heated to 70 C and Toluene-4-sulfonic acid-3-(t- butyl dimethyl)-silanyloxypropyl ester (12.7 g 0.037 mole) was added to reaction mixture. Reaction mixture was quenched in distilled water and product extracted in ethyl acetate and extract washed with saturated brine solution, dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to give 10g of (II) as oil.
	With potassium carbonate; In N,N-dimethyl-formamide; at 70.0℃;	A mixture of 7-Cyano indoline (5 g, 0.035 mole), dimethyl formamide (50 ml) and powdered K2CO3 (9.6 g, 0.07 mole) was heated to 70 C. and Toluene-4-sulfonic acid-3-(t-butyl dimethyl)-silanyloxypropyl ester (12.7 g 0.037 mole) was added to reaction mixture. Reaction mixture was quenched in distilled water and product extracted in ethyl acetate and extract washed with saturated brine solution, dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to give 10 g of (II) as oil.

Reference： [1]Patent: WO2011/30356,2011,A2 .Location in patent: Page/Page column 20; 21
[2]Patent: US2012/165548,2012,A1 .Location in patent: Page/Page column 10

9
[ 115661-82-0 ]
[ 160970-54-7 ]