[ CAS No. 59908-47-3 ] {[proInfo.proName]}

Name: 59908-47-3|5-Chloro-1-methyl-1H-indole-2-carboxylic acid|98%
Brand: Ambeed
SKU: A121228
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Quality Control of [ 59908-47-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 59908-47-3 ]

Product Details of [ 59908-47-3 ]

CAS No. :	59908-47-3	MDL No. :	MFCD03848205
Formula :	C₁₀H₈ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UTJVSPKRDDKHND-UHFFFAOYSA-N
M.W :	209.63	Pubchem ID :	931711
Synonyms :

Calculated chemistry of [ 59908-47-3 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.1
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	55.17
TPSA :	42.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.71 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.92
Log Po/w (XLOGP3) :	2.63
Log Po/w (WLOGP) :	2.53
Log Po/w (MLOGP) :	1.94
Log Po/w (SILICOS-IT) :	1.93
Consensus Log Po/w :	2.19

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.21
Solubility :	0.13 mg/ml ; 0.000622 mol/l
Class :	Soluble
Log S (Ali) :	-3.17
Solubility :	0.143 mg/ml ; 0.00068 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.84
Solubility :	0.302 mg/ml ; 0.00144 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.44

Safety of [ 59908-47-3 ]

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 [ 59908-47-3 ]

* 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 [ 59908-47-3 ]
Downstream synthetic route of [ 59908-47-3 ]

[ 59908-47-3 ] Synthesis Path-Upstream 1~5

1
[ 148356-79-0 ]
[ 59908-47-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydroxide In ethanol at 50℃; for 0.5 h;	77 mg (0.34 mmol) of the compound prepared in the above step 1 was dissolved in ethanol, 2M sodium hydroxide was added, and the mixture was stirred at 50 ° C for 30 minutes. After completion of the reaction, the reaction mixture was extracted with 50 ml of ethyl acetate, washed with 4N hydrochloric acid and water, and dried over anhydrous sodium sulfate.And concentrated under reduced pressure to obtain 67 mg (0.32 mmol) of the title compound as white solid in 94percent yield.
77.6%	With water; lithium hydroxide In tetrahydrofuran at 20℃; for 2 h;	Step 2: Synthesis of 5-chloro-l-methyl-lH-indole-2-carboxylic acid 43.2 [00509] To a solution of methyl 5 -chloro-1 -methyl- lH-indole-2-carboxylate (43.1, 224 mg, 1.0 mmol) in THF (10ml) was added LiOH (36 mg, 1.5 mmol) in water (2ml) and the resulting mixture was stirred under air at rt. After 2h the solvent was removed under reduced pressure and the residue was taken up in IN aqueous hydrochloric acid (10ml). The resulting suspension was allowed to stand for ten minutes, then was filtered through filter paper and the solid was collected and dried under vacuum to afford 163 mg (77.6percent) of 43.2 5 -chloro-1 -methyl- 1H- indole-2-carboxylic acid as a beige powder.
58.8 mg	With water; lithium hydroxide In tetrahydrofuran for 2 h; Reflux	General procedure: To a solution of 1a (100 mg, 510 μmol) in DMF (1.89 mL) were added K₂CO₃ (2.11 g, 15.3 mmol) and MeI (160 μL, 2.55 mmol) at room temperature. The reaction mixture was stirred for 20 h. After stirring, the reaction mixture was dissolved in EtOAc, washed with H₂O, and dried over MgSO₄ followed by concentration under reduced pressure. The residue was dissolved in THF/H₂O (5/1, 2.50 mL), and 1 M LiOH aq. (750 μL, 750 μmol) was added at room temperature. The reaction mixture was refluxed and stirred for 2 h. After being cooled to room temperature, the reaction mixture was quenched by saturated aqueous NH₄Cl solution and extracted with EtOAc. The extract was washed with brine and dried over MgSO₄. Concentration under reduced pressure provided the title compound 1b (58.8 mg, 55percent yield) as white powder.;

Reference： [1] Patent: KR101725451, 2017, B1, . Location in patent: Paragraph 0294; 0301-0303
[2] Patent: WO2016/40449, 2016, A1, . Location in patent: Paragraph 00508-00509
[3] Patent: WO2006/66879, 2006, A2, . Location in patent: Page/Page column 53; 48
[4] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 21, p. 5664 - 5671

2
[ 4792-67-0 ]
[ 74-88-4 ]
[ 59908-47-3 ]
[ 59908-53-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere	): To a stirred solution of ethyl 18 (1 g, 4.48 mmol) in DMF (10 ml) was added NaH (0.215 g, 5.4 mmol, 60percent dispersion in mineral oil) at 0 °C, and stirred for 30 min followed by the addition of MeI (0.764 g, 5.4 mmol). After stirred at room temperature for about 20 min, the reaction mixture was quenched with 4 N HCl at 0 °C and extracted with Et₂O for four times. The organic layers were combined, washed with brine, and dried over Na₂SO₄. The solvent were evaporated under reduced pressure and the crude was purified using silica gel chromatography (10percent EtOAc / hexane) to afford ethyl 5-chloro-1H-indole-2-carboxylate (1 g, 94percent). HRMS (ESI) m/z calcd for [C₁₂H₁₃ClNO₂]⁺: 238.0629 found 238.0678. ¹H NMR (400 MHz, CDCl₃): δ 7.64 (s, 1H), 7.30 (d, J = 1.9 Hz, 2H), 7.22 (s, 1H), 4.38 (q, J = 7.1 Hz, 2H), 4.06 (s, 3H), 1.41 (t, J = 7.1 Hz, 3H). ¹³C NMR (100 MHz): δ 161.95, 137.92, 129.20, 126.66, 126.19, 125.35, 121.62, 111.39, 109.30, 60.75, 31.84, 14.35

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 20, p. 4770 - 4776

3
[ 10517-21-2 ]
[ 74-88-4 ]
[ 59908-47-3 ]

Reference： [1] Patent: WO2006/66879, 2006, A2, . Location in patent: Page/Page column 48-49; 53

4
[ 10517-21-2 ]
[ 59908-47-3 ]

Reference： [1] Patent: WO2016/40449, 2016, A1,
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 21, p. 5664 - 5671

5
[ 87802-11-7 ]
[ 59908-47-3 ]

Reference： [1] Patent: KR101725451, 2017, B1,

[ 59908-47-3 ] Synthesis Path-Downstream 1~17

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 0 - 20℃; for 2h;	General procedure: To lnt-029 (12.0 g, 47.7 mmol) in THF (70 ml_)/water (25 mL) lithium hydroxide monohydrate (8.01 g, 191 mmol) is added at 0 C and stirred at ambient temperature for 2 h. 4 N HCI (10 mL) is added, and the mixture is extracted exhaustively with EtOAc. The combined organic layer is washed with water and brine, dried (MgS04), filtered and concentrated in vacuo. The residue is triturated with ether and pentane.

3
[ 59908-47-3 ]
3-{4-[3-(aminomethyl)phenoxy]-2-methylphenyl}propanoic acid ester [ No CAS ]
3-[4-(3-[(5-chloro-1-methyl-1H-indole-2-carbonyl)-amino]-methyl}-phenoxy)-2-methyl-phenyl]-propionic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6744 - 6749

4
[ 10517-21-2 ]
[ 74-88-4 ]
[ 59908-47-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 65℃; for 8h;	5-Chloroindole-2-carboxylic acid (2.5 mmol) was dissolved in CH3CN (20 ml). DBU (6.5 mmol) and MeI (5.6 mmol) were added. The mixture was stirred at 65C for 8 hours. The solvent was removed under reduced pressure. The residue (2.5 mmol) was dissolved in dry 1 , 4-dioxane (20 ml) and the solution was cooled to O0C. NaH (8.1 mmol) was added and the mixture was stirred at O0C for 15 minutes. MeI (10 mmol) was added and the mixture was stirred at 00C for 1 hour and at room temperature for 2 days. The reaction mixture was poured into water (150 ml). The water layer was extracted with Et2O (3 x 100 ml). The combined organic layers were EPO <DP n="50"/>washed with 1N HCI (3 x 200 ml), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash chromatography.

Reference： [1]Patent: WO2006/66879,2006,A2 .Location in patent: Page/Page column 48-49; 53

5
[ 148356-79-0 ]
[ 59908-47-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydroxide; In ethanol; at 50℃; for 0.5h;	77 mg (0.34 mmol) of the compound prepared in the above step 1 was dissolved in ethanol, 2M sodium hydroxide was added, and the mixture was stirred at 50 C for 30 minutes. After completion of the reaction, the reaction mixture was extracted with 50 ml of ethyl acetate, washed with 4N hydrochloric acid and water, and dried over anhydrous sodium sulfate.And concentrated under reduced pressure to obtain 67 mg (0.32 mmol) of the title compound as white solid in 94% yield.
77.6%	With water; lithium hydroxide; In tetrahydrofuran; at 20℃; for 2h;	Step 2: Synthesis of 5-chloro-l-methyl-lH-indole-2-carboxylic acid 43.2 [00509] To a solution of methyl 5 -chloro-1 -methyl- lH-indole-2-carboxylate (43.1, 224 mg, 1.0 mmol) in THF (10ml) was added LiOH (36 mg, 1.5 mmol) in water (2ml) and the resulting mixture was stirred under air at rt. After 2h the solvent was removed under reduced pressure and the residue was taken up in IN aqueous hydrochloric acid (10ml). The resulting suspension was allowed to stand for ten minutes, then was filtered through filter paper and the solid was collected and dried under vacuum to afford 163 mg (77.6%) of 43.2 5 -chloro-1 -methyl- 1H- indole-2-carboxylic acid as a beige powder.
		The ester (1.7 mmol) was dissolved in ethanol (5 ml) and 2N NaOH (10 ml) was added. The reaction mixture was stirred at 45C for 30 minutes. The reaction mixture was cooled to room temperature and ethanol was removed under reduced pressure. The residue was diluted with water (10 ml), cooled to 00C and acidified to pH=1 using 6N HCI. The precipitate was filtered, washed with water (3x10 ml) and dried under reduced pressure.

58.8 mg

With water; lithium hydroxide; In tetrahydrofuran; for 2h;Reflux;

General procedure: To a solution of 1a (100 mg, 510 mumol) in DMF (1.89 mL) were added K2CO3 (2.11 g, 15.3 mmol) and MeI (160 muL, 2.55 mmol) at room temperature. The reaction mixture was stirred for 20 h. After stirring, the reaction mixture was dissolved in EtOAc, washed with H2O, and dried over MgSO4 followed by concentration under reduced pressure. The residue was dissolved in THF/H2O (5/1, 2.50 mL), and 1 M LiOH aq. (750 muL, 750 mumol) was added at room temperature. The reaction mixture was refluxed and stirred for 2 h. After being cooled to room temperature, the reaction mixture was quenched by saturated aqueous NH4Cl solution and extracted with EtOAc. The extract was washed with brine and dried over MgSO4. Concentration under reduced pressure provided the title compound 1b (58.8 mg, 55% yield) as white powder.;

Reference： [1]Patent: KR101725451,2017,B1 .Location in patent: Paragraph 0294; 0301-0303
[2]Patent: WO2016/40449,2016,A1 .Location in patent: Paragraph 00508-00509
[3]Patent: WO2006/66879,2006,A2 .Location in patent: Page/Page column 53; 48
[4]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5664 - 5671

6
tert-butyl 6-azidooctahydroisoquinoline-2(1H)-carboxylate [ No CAS ]
[ 59908-47-3 ]
tert-butyl 6-[5-chloro-1-methyl-1H-indol-2-yl]carbonyl}aminooctahydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Production Example 5-4tert-butyl 6-[5-chloro-1-methyl-1H-indol-2-yl]carbonyl}amino)octahydroisoquinoline-2(1H)-carboxylate To a methanol solution (100 mL) of the compound obtained in Production example 5-3 (3.3 g), 10% palladium carbon (500 mg) was added, and the resulting solution was stirred overnight at room temperature under 1 atm hydrogen atmosphere. The reaction solution was filtered and the filtrate was concentrated under reduced pressure. To a DMF (70 mL) solution of the residue, commercially available <strong>[59908-47-3]5-chloro-1-methyl-1H-indole-2-carboxylic acid</strong> (2.4 g), HATU (4.4 g) and subsequently diisopropylethylamine (4.1 mL) were added, and the resulting solution was stirred overnight at room temperature. Water was added to the reaction solution, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:2), whereby the title compound (3.2 g) was obtained as a single optically active isomer (the arrangement in the structural formula is a relative configuration).

Reference： [1]Patent: US2012/28990,2012,A1 .Location in patent: Page/Page column 15-16

7
[ 1601751-76-1 ]
[ 59908-47-3 ]
[ 1624309-58-5 ]

Reference： [1]ChemMedChem,2014,vol. 9,p. 1850 - 1859

8
[ 10517-21-2 ]
[ 59908-47-3 ]

Reference： [1]Patent: WO2016/40449,2016,A1
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5664 - 5671

9
4-amino-N-(pyrimidin-2-yl)-N-[2-(trimethylsilyl)ethoxy]methyl}benzene-1-sulfonamide [ No CAS ]
[ 59908-47-3 ]
5-chloro-1-methyl-N-{4-[(pyrimidin-2-yl)([2-(trimethylsilyl)ethoxy]methyl})sulfamoyl]phenyl}-1H-indole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With 3-Methylpyridine; methanesulfonyl chloride; In acetonitrile; at 20℃; for 60h;Inert atmosphere;	Step 3: Synthesis of 5-chloro-l-methyl-N-{4-[(pyrimidin-2-yl)([2- (trimethylsilyl)ethoxy] methyl})sulfamoyl]phenyl}-lH-indole-2-carboxamide 43.3 [00511] To a solution of 5-chloro-l-methyl-lH-indole-2-carboxylic acid (43.2, 81 mg, 0.39 mmol) in MeCN (dry, 5ml) was added 4-amino-N-phenyl-N-[2- (trimethylsilyl)ethoxy]methyl}benzene-l-sulfonamide (150 mg, 0.4 mmol) and 3-picoline (57 mu, 0.58 mmol). To this solution was added methanesulfonyl chloride (36 mu, 0.46 mmol) and the mixture was stirred under nitrogen at rt. After 60h the solvent was removed in vacuo and the crude material purified by flash column chromatography (heptane/EtOAc 80/20 to 60/40) to obtain 97 mg (43%) of 5-chloro-l-methyl-N-{4-[(pyrimidin-2-yl)([2- (trimethylsilyl)ethoxy]methyl})sulfamoyl]phenyl}-lH-indole-2-carboxamide 43.3 as a white powder.

Reference： [1]Patent: WO2016/40449,2016,A1 .Location in patent: Paragraph 00510-00511

10
[ 1442116-78-0 ]
[ 59908-47-3 ]
[ 1442120-44-6 ]

Yield	Reaction Conditions	Operation in experiment
43 mg	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 1h;	General procedure: Version B: 780 mg of 1 d and 1747 mg of HATU were first dissolved in 10 ml DMSO. Next, 314 mg of 2-methoxyethylamine and 1080 mg of N,N-diisopropylethylamine were added. The mixture was stirred for 1 hr at RT. The reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue was purified chromatographically on the Biotage SP4. Gradient: ethyl acetate/methanol 0-10%. Yield: 740 mg of the title compound. Analogously to Example 1b, Version B, 43 mg of the title compound was obtained from 100 mg of 71a and 89 mg of <strong>[59908-47-3]5-chloro-1-methyl-1H-indol-2-carboxylic acid</strong> in DMF. 1H-NMR (400 MHz, DMSO-d6): delta [ppm], 1.29 (2H), 1.38-1.72 (2H), 2.26-2.43 (1H), 2.54 (3H), 2.71-3.21 (2H), 3.73 (3H), 3.84-4.18 (3H), 4.38 (3H), 6.59 (1H), 7.15-7.28 (2H), 7.47 (1H), 7.55 (1H), 7.65 (1H), 8.57 (1H), 8.83 (1H).

Reference： [1]Patent: US2016/89364,2016,A1 .Location in patent: Page/Page column 24; 147

11
[ 6832-87-7 ]
[ 59908-47-3 ]
5'-chloro-1,1'-dimethyl-2,3'-spirobi[indolin]-2-one [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 2711 - 2715

12
[ 6832-87-7 ]
[ 59908-47-3 ]
N-(2-bromophenyl)-5-chloro-N,1-dimethyl-1H-indole-2-carboxamide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 2711 - 2715

13
[ 87802-11-7 ]
[ 59908-47-3 ]

Reference： [1]Patent: KR101725451,2017,B1

14
[ 4792-67-0 ]
[ 74-88-4 ]
[ 59908-47-3 ]
[ 59908-53-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20℃;Inert atmosphere;	): To a stirred solution of ethyl 18 (1 g, 4.48 mmol) in DMF (10 ml) was added NaH (0.215 g, 5.4 mmol, 60% dispersion in mineral oil) at 0 C, and stirred for 30 min followed by the addition of MeI (0.764 g, 5.4 mmol). After stirred at room temperature for about 20 min, the reaction mixture was quenched with 4 N HCl at 0 C and extracted with Et2O for four times. The organic layers were combined, washed with brine, and dried over Na2SO4. The solvent were evaporated under reduced pressure and the crude was purified using silica gel chromatography (10% EtOAc / hexane) to afford ethyl 5-chloro-1H-indole-2-carboxylate (1 g, 94%). HRMS (ESI) m/z calcd for [C12H13ClNO2]+: 238.0629 found 238.0678. 1H NMR (400 MHz, CDCl3): delta 7.64 (s, 1H), 7.30 (d, J = 1.9 Hz, 2H), 7.22 (s, 1H), 4.38 (q, J = 7.1 Hz, 2H), 4.06 (s, 3H), 1.41 (t, J = 7.1 Hz, 3H). 13C NMR (100 MHz): delta 161.95, 137.92, 129.20, 126.66, 126.19, 125.35, 121.62, 111.39, 109.30, 60.75, 31.84, 14.35

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4770 - 4776

15
[ 36768-62-4 ]
[ 59908-47-3 ]
5-chloro-1-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1H-indole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 20h;	General procedure: To a solution of 1a (196 mg, 1.00 mmol) in DMF (3.30 mL) were added HOBt·H2O (149 mg, 1.10 mmol), EDCI·HCl (211 mg, 1.10 mmol), 2,2,6,6-tetramethylpiperidin-4-amine (156 muL, 900 mumol) and Et3N (152 muL, 1.10 mmol) at 0 C. The reaction mixture was heated to room temperature and stirred for 20 h. The reaction was quenched with saturated aqueous NaHCO3 solution and extracted with CHCl3. The extract was washed with brine and dried over MgSO4. Concentration under reduced pressure provided the title compound 9a (210 mg, 74% yield) as a white powder.

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5664 - 5671

16
[ 1522-13-0 ]
[ 59908-47-3 ]
7-chloro-10-methyl-3,3,5-triphenyl-3,10-dihydro-1H-oxepino[3,4-b]indol-1-one [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 5447 - 5451

17
[ 174636-76-1 ]
[ 59908-47-3 ]
5-chloro-1-methyl-1H-indole-2-carboxylic acid (2-methoxy-1-phenylethyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: 5-chloro-1-methyl-1H-indole-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dimethyl sulfoxide at 20℃; for 0.0833333h; Stage #2: (R,S)-2-methoxy-1-phenylethylamine In dimethyl sulfoxide at 20℃; for 1.5h;

Reference： [1]Arnhof, Heribert; Bader, Gerd; Bruchhaus, Jens; Burkard, Michelle; Ciftci, Tuncay; Dahmann, Georg; Du, Alicia; Ettmayer, Peter; Fett, Thomas N.; Garavel, Géraldine; Gerstberger, Thomas; Haering, Daniela; Harrer, Christoph; Hofbauer, Karin S.; Kessler, Dirk; Kousek, Roland; Li, Dongyang; Li, Yali; Lv, Xiaobing; Martinelli, Paola; Mayer, Moriz; McConnell, Darryl B.; Mischerikow, Nikolai; Mitzner, Sophie; Pearson, Mark; Peric-Simov, Biljana; Quant, Jens; Rinnenthal, Joerg; Rumpel, Klaus; Savarese, Fabio; Scherbantin, Yvonne; Schnitzer, Renate; Scholz, Guido; Schrenk, Andreas; Sharps, Bernadette; Sommergruber, Wolfgang; Treu, Matthias; Weinstabl, Harald; Wolkerstorfer, Bernhard; Zahn, Stephan K.; Zhang, Xuechun; Zoephel, Andreas [Journal of Medicinal Chemistry, 2019]

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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 59908-47-3 ] {[proInfo.proName]}

Quality Control of [ 59908-47-3 ]

Related Doc. of [ 59908-47-3 ]

Product Details of [ 59908-47-3 ]

Calculated chemistry of [ 59908-47-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 59908-47-3 ]

Application In Synthesis of [ 59908-47-3 ]

[ 59908-47-3 ] Synthesis Path-Upstream 1~5

[ 59908-47-3 ] Synthesis Path-Downstream 1~17

Related Functional Groups of [ 59908-47-3 ]

Chlorides

Carboxylic Acids

Related Parent Nucleus of [ 59908-47-3 ]

Indoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 59908-47-3 ]

Related Parent Nucleus of
[ 59908-47-3 ]