[ CAS No. 172078-33-0 ] {[proInfo.proName]}

Name: 172078-33-0|Indolin-5-ol|98%
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Quality Control of [ 172078-33-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 172078-33-0 ]

SDS Specification

Alternatived Products of [ 172078-33-0 ]

Product Details of [ 172078-33-0 ]

CAS No. :	172078-33-0	MDL No. :	MFCD02181134
Formula :	C₈H₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MPCXQPXCYDDJSR-UHFFFAOYSA-N
M.W :	135.16	Pubchem ID :	10034684
Synonyms :

Calculated chemistry of [ 172078-33-0 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	43.56
TPSA :	32.26 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) :	-5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.21
Log Po/w (XLOGP3) :	1.89
Log Po/w (WLOGP) :	0.79
Log Po/w (MLOGP) :	1.09
Log Po/w (SILICOS-IT) :	1.74
Consensus Log Po/w :	1.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.31
Solubility :	0.658 mg/ml ; 0.00487 mol/l
Class :	Soluble
Log S (Ali) :	-2.19
Solubility :	0.873 mg/ml ; 0.00646 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.39
Solubility :	0.547 mg/ml ; 0.00405 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.23

Safety of [ 172078-33-0 ]

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

Application In Synthesis of [ 172078-33-0 ]

* 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 [ 172078-33-0 ]
Downstream synthetic route of [ 172078-33-0 ]

[ 172078-33-0 ] Synthesis Path-Upstream 1~2

1
[ 1953-54-4 ]
[ 172078-33-0 ]

Yield	Reaction Conditions	Operation in experiment
35%	Stage #1: at 20℃; for 1 h; Inert atmosphere Stage #2: With sodium hydroxide In water	2,3-dihydro-1H-indol-5-ol Under a nitrogen atmosphere 0.34 g sodium cyanoborohydride were added batchwise to 0.60 g (4.5 mmol) 5-hydroxyindole in 5.0 mL glacial acetic acid and the mixture was stirred for 60 min at RT. Then the reaction mixture was poured onto a 4N aqueous sodium hydroxide solution and extracted with EtOAc. The combined organic phases were washed several times with saturated sodium hydrogen carbonate solution, dried on sodium sulphate and evaporated down. Yield: 265 mg (35percent of theoretical) ESI-MS: m/z=136 (M+H)⁺ R_t(HPLC-MS): 0.38 min (method C)
32%	at 25℃; for 12 h;	Sodium cyanoborohydride (4.72 g, 75.1 mmol) was added portionwise to a solution of 5-hydroxy-1H-indole (4g, 30 mmol) in acetic acid (120 ml). The reaction solution was stirred at 25 °C for 12 hours, and then rotary evaporatedto remove the solvent, the residue was dissolved in ethyl acetate (200 ml), and washed with saturated sodium bicarbonate.The aqueous layer was extracted with ethyl acetate (3 x 150 ml). The organic layers were combined and washed withsaturated NaCl solution, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The residue waspurified by column chromatography (petroleum ether/ethyl acetate = 3: 1, Rf = 0.3) to give compound 24A (creamy whitesolid, 1.3 g, 32percent).1H NMR (400MHz, CHLOROFORM-d) = 6.69 (s, 1H), 6.59 - 6.49 (m, 2H), 3.55 (t, J=8.3 Hz, 2H), 3.01 (t, J=8.3 Hz, 2H),2.20 (s, 1H)

Reference： [1] Patent: US2011/21500, 2011, A1, . Location in patent: Page/Page column 46
[2] Patent: EP3293177, 2018, A1, . Location in patent: Paragraph 0217; 0218
[3] Patent: EP1154774, 2005, B1, . Location in patent: Page/Page column 118

2
[ 21857-45-4 ]
[ 172078-33-0 ]

Reference： [1] Patent: US2009/233910, 2009, A1, . Location in patent: Page/Page column 88-89

[ 172078-33-0 ] Synthesis Path-Downstream 1~66

1
[ 172078-33-0 ]
[ 100-47-0 ]
(5-hydroxy-2,3-dihydro-1H-indol-7-yl)-phenyl-methanone [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 35 - 38

2
[ 172078-33-0 ]
9-hydroxy-1-phenyl-6,7-dihydro-3H-[1,4]diazepino[6,7,1-hi]indol-4-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 35 - 38

3
[ 172078-33-0 ]
3-amino-9-hydroxy-1-phenyl-6,7-dihydro-3H-[1,4]diazepino[6,7,1-hi]indol-4-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 35 - 38

4
[ 172078-33-0 ]
9-hydroxy-1-phenyl-6,7-dihydro-[1,4]diazepino[6,7,1-hi]indole-3,4-dione 3-oxime [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 35 - 38

5
[ 172078-33-0 ]
(3R)-Isoquinoline-3-carboxylic acid (9-hydroxy-4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino [6,7,1-hi]indol-3-yl) amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 35 - 38

6
[ 1538-75-6 ]
[ 172078-33-0 ]
5-hydroxy-(1-tertbutoxycarbonyl)-2,3-dihydroindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; acetone;	5-Hydroxy-2,3-dihydro-1H-indole (1.5 g, 11.1 mmol) was suspended in a mixture of acetone (7 ml) trichloromethane (7 ml) and THF (6 ml). tert-Butoxycarbonylanhydride (2.42 g, 11 mmol) in solution in THF (7 ml) was added dropwise. The reaction mixture was stirred overnight at ambient temperature, the solvent was evaporated, the residue was partitioned between ethyl acetate and water, the organic phase was washed with water, brine, dried (MgSO4), filtered and the solvent evaporated. The solid was purified by flash chromatography using dichloromethane/methanol (95/5) as solvent. Evaporation of the olvent gave 5-hydroxy-(1-tertbutoxycarbonyl)-2,3-dihydroindole (2.28 g, 87%) as an off white solid. 1H NMR Spectrum: (CDCl3) 3.05 (t, 2H); 3.95 (br s, 2H); 4.70 (br s, 1H); 6.60 (d, 1H); 6.65 (s, 1H); 7.70 (br s, 1H)

Reference： [1]Patent: EP1154774,2005,B1 .Location in patent: Page/Page column 118

7
[ 1953-54-4 ]
[ 172078-33-0 ]

Yield	Reaction Conditions	Operation in experiment
35%		2,3-dihydro-1H-indol-5-ol Under a nitrogen atmosphere 0.34 g sodium cyanoborohydride were added batchwise to 0.60 g (4.5 mmol) 5-hydroxyindole in 5.0 mL glacial acetic acid and the mixture was stirred for 60 min at RT. Then the reaction mixture was poured onto a 4N aqueous sodium hydroxide solution and extracted with EtOAc. The combined organic phases were washed several times with saturated sodium hydrogen carbonate solution, dried on sodium sulphate and evaporated down. Yield: 265 mg (35% of theoretical) ESI-MS: m/z=136 (M+H)+ Rt (HPLC-MS): 0.38 min (method C)
32%	With sodium cyanoborohydride; acetic acid; at 25℃; for 12h;	Sodium cyanoborohydride (4.72 g, 75.1 mmol) was added portionwise to a solution of 5-hydroxy-1H-indole (4g, 30 mmol) in acetic acid (120 ml). The reaction solution was stirred at 25 C for 12 hours, and then rotary evaporatedto remove the solvent, the residue was dissolved in ethyl acetate (200 ml), and washed with saturated sodium bicarbonate.The aqueous layer was extracted with ethyl acetate (3 x 150 ml). The organic layers were combined and washed withsaturated NaCl solution, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The residue waspurified by column chromatography (petroleum ether/ethyl acetate = 3: 1, Rf = 0.3) to give compound 24A (creamy whitesolid, 1.3 g, 32%).1H NMR (400MHz, CHLOROFORM-d) = 6.69 (s, 1H), 6.59 - 6.49 (m, 2H), 3.55 (t, J=8.3 Hz, 2H), 3.01 (t, J=8.3 Hz, 2H),2.20 (s, 1H)
	With ammonia; sodium cyanoborohydride; In methanol; for 3h;Heating / reflux;	The starting material was prepared as follows: 5-Hydroxyindole (2 g, 15 mmol) was dissolved in methanol (60 ml) under argon. Sodium cyanoborohydride (1.89 g, 30 mmol) and trifluoroboron etherate (4.2 ml, 33 mmol) were added and the mixture was heated at reflux for 3 hours then left to cool to ambient temperature. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. Ammonia was added to adjust the pH to 10 and the aqueous phase was extracted with more ethyl acetate. The combined organic phases were washed with water, brine, dried (MgSO4), filtered and the solvent evaporated. The residue was purified by flash chromatography using dichloromethane/methanol (95/5) as solvent. Evaporation of the solvent gave 5-hydroxy-2,3-dihydro-1H-indole (1.45 g, 73%) as an off white solid. 1H NMR Spectrum: (DMSOd6+ TFA) 3.15 (t, 2H); 3.70 (t, 2H); 6.75 (dd, 1H); 6.85 (d, 1H); 7.30 (d, 1H)

Reference： [1]Patent: US2011/21500,2011,A1 .Location in patent: Page/Page column 46
[2]Patent: EP3293177,2018,A1 .Location in patent: Paragraph 0217; 0218
[3]Patent: EP1154774,2005,B1 .Location in patent: Page/Page column 118

8
[ 172078-33-0 ]
[ 13790-39-1 ]
[ 172078-92-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	In isopropyl alcohol;	Example 48 1-(6,7-Dimethoxy-quinazolin-4-yl)-2,3-dihydro-1H-indol-5-ol methanesulfonate salt Utilizing a procedure analogous to that described in Example 1 (with conversion to the methanesulfonate salt analogous to that described in Example 44), this product was prepared in 90% yield from 5-hydroxy-indoline (1.1 eq.), and 4-chloro-6,7-dimethoxy-quinazoline (1.0 eq) in i-PrOH. (M.P. 245-250 C. (dec); LC-MS: 324 (MH+); anal. RP18-HPLC RT: 2.76 min.).

Reference： [1]Patent: US5736534,1998,A

9
[ 21857-45-4 ]
[ 172078-33-0 ]

Yield	Reaction Conditions	Operation in experiment
	With water; hydrogen bromide; at 140℃; for 3h;	12 g of compound obtained in the preceding step are heated at 140 C. for 3 h in HBr (48%, 200 ml). After cooling to AT, filtering, the filtrate is concentrated dry. The residue is washed with acetone and dried. 14.8 g of desired product are obtained and used as such.

Reference： [1]Patent: US2009/233910,2009,A1 .Location in patent: Page/Page column 88-89

10
[ 1158918-65-0 ]
[ 172078-33-0 ]
[ 1158918-24-1 ]

Yield	Reaction Conditions	Operation in experiment
23%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	Example 40 5-(6-(<strong>[172078-33-0]5-hydroxyindoline</strong>-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one 0.15 g (0.37 mmol) 6-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride, 50 mg (0.37 mmol) 2,3-dihydro-1H-indol-5-ol, 150 muL (0.87 mmol) DI PEA and 0.13 g (0.41 mmol) TBTU in 1.8 mL DMF were stirred overnight at RT. The purification was carried out by preparative HPLC-MS. The product-containing fractions were combined and lyophilised. Yield: 44 mg (23% of theory) ESI-MS: m/z=491 (M+H)+ Rt (HPLC-MS): 1.33 min (method C)

Reference： [1]Patent: US2011/21500,2011,A1 .Location in patent: Page/Page column 64

11
[ 24424-99-5 ]
[ 172078-33-0 ]
[ 170147-76-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium hydrogencarbonate; In chloroform; at 20℃;Product distribution / selectivity;	Example 49: 5-Hydroxy-2,3-dihydro-indole-l-carboxylic acid tert-butyl esterA mixture of 2,3-dihydro-lH-indol-5-ol (1.0 g, 7.8 mmol), di-te/t-butyldicarbonate (4.0 g, 18 mmol), chloroform (20 mL) and saturated sodium bicarbonate aq. (8 mL) was stirred at room temperature over night. The organic phase was separated and washed twice with water, dried over MgSO4, filtered and concentrated to give crude product. The crude material was treated with ether and filtered to give product (1.1 g, yield: 60%). ESI-MS: 258.10 (M+23)+, 1H NMR (400 MHz, DMSO) delta 9.00 (s, IH), 7.48 (ws, IH), 6.61 (d, IH), 6.51 (dd, IH), 3.84 (t, 2H), 2.96 (t, 2H), 1.48 (s, 9H).

Reference： [1]Patent: WO2011/17561,2011,A1 .Location in patent: Page/Page column 47

12
[ 172078-33-0 ]
[ 1266116-33-9 ]

Reference： [1]Patent: WO2011/17561,2011,A1

13
[ 172078-33-0 ]
[ 1266116-34-0 ]

Reference： [1]Patent: WO2011/17561,2011,A1

14
[ 172078-33-0 ]
[ 1266116-37-3 ]

Reference： [1]Patent: WO2011/17561,2011,A1

15
[ 172078-33-0 ]
[ 1266116-41-9 ]

Reference： [1]Patent: WO2011/17561,2011,A1

16
[ 172078-33-0 ]
[ 1266116-46-4 ]

Reference： [1]Patent: WO2011/17561,2011,A1

17
[ 172078-33-0 ]
[ 1266116-47-5 ]

Reference： [1]Patent: WO2011/17561,2011,A1

18
[ 172078-33-0 ]
[ 1266116-48-6 ]

Reference： [1]Patent: WO2011/17561,2011,A1

19
[ 172078-33-0 ]
[ 1266120-63-1 ]

Reference： [1]Patent: WO2011/17561,2011,A1

20
[ 96557-30-1 ]
[ 172078-33-0 ]
C₁₆H₁₆BrNO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472
[2]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

21
[ 4251-63-2 ]
[ 172078-33-0 ]
C₁₆H₁₆ClNO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

22
[ 4251-63-2 ]
[ 172078-33-0 ]
C₁₆H₁₅NO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

23
[ 109347-41-3 ]
[ 172078-33-0 ]
C₁₆H₁₅NO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

24
[ 109347-41-3 ]
[ 172078-33-0 ]
C₁₆H₁₆INO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

25
C₈H₆BrClO [ No CAS ]
[ 172078-33-0 ]
C₁₆H₁₄ClNO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

26
C₈H₆BrClO [ No CAS ]
[ 172078-33-0 ]
C₁₆H₁₅BrClNO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

27
[ 905710-81-8 ]
[ 172078-33-0 ]
C₁₆H₁₄FNO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

28
[ 905710-81-8 ]
[ 172078-33-0 ]
C₁₆H₁₅BrFNO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472
[2]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

29
2-(2-bromo-5-(trifluoromethyl)phenyl)acetaldehyde [ No CAS ]
[ 172078-33-0 ]
C₁₇H₁₄F₃NO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

30
2-(2-bromo-5-(trifluoromethyl)phenyl)acetaldehyde [ No CAS ]
[ 172078-33-0 ]
C₁₇H₁₅BrF₃NO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472
[2]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

31
[ 1241405-24-2 ]
[ 172078-33-0 ]
C₁₇H₁₇NO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

32
[ 1241405-24-2 ]
[ 172078-33-0 ]
C₁₇H₁₈BrNO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472
[2]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

33
2-(2-bromo-5-methoxyphenyl)acetaldehyde [ No CAS ]
[ 172078-33-0 ]
C₁₇H₁₇NO₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

34
2-(2-bromo-5-methoxyphenyl)acetaldehyde [ No CAS ]
[ 172078-33-0 ]
C₁₇H₁₈BrNO₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472
[2]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

35
[ 90841-59-1 ]
[ 172078-33-0 ]
C₁₈H₂₀BrNO₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472
[2]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

36
[ 889115-21-3 ]
[ 172078-33-0 ]
C₁₇H₁₆BrNO₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472
[2]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

37
[ 889115-21-3 ]
[ 172078-33-0 ]
C₁₇H₁₅NO₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

38
[ 172078-33-0 ]
[ 107408-16-2 ]
C₁₇H₁₈BrNO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472
[2]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

39
[ 172078-33-0 ]
[ 107408-16-2 ]
C₁₇H₁₇NO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

40
C₆H₅BrOS [ No CAS ]
[ 172078-33-0 ]
C₁₄H₁₄BrNOS [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

41
C₆H₅BrOS [ No CAS ]
[ 172078-33-0 ]
C₁₄H₁₃NOS [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

42
C₁₁H₁₀BrNO [ No CAS ]
[ 172078-33-0 ]
C₁₉H₁₉BrN₂O [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

43
C₁₁H₁₀BrNO [ No CAS ]
[ 172078-33-0 ]
C₁₉H₁₈N₂O [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

44
[ 172078-33-0 ]
[ 6630-33-7 ]
C₁₅H₁₄BrNO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

45
[ 172078-33-0 ]
C₁₆H₁₅NO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

46
[ 172078-33-0 ]
C₁₆H₁₅NO [ No CAS ]
C₁₆H₁₅NO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15469 - 15472

47
[ 172078-33-0 ]
C₁₃H₁₅NO₄ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 12687 - 12691
Angew. Chem.,2015,vol. 127,p. 12878 - 12882,5

48
[ 172078-33-0 ]
C₂₀H₁₅NO₅ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 12687 - 12691
Angew. Chem.,2015,vol. 127,p. 12878 - 12882,5

49
[ 172078-33-0 ]
[ 2937-50-0 ]
5-hydroxy-2,3-dihydroindole-1-carboxylic acid allyl ester [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 12687 - 12691
Angew. Chem.,2015,vol. 127,p. 12878 - 12882,5

50
6-(3,5-dimethylisoxazol-4-yl)-7-methoxy-2-oxo-1-(pyridin-2-yl methyl)-1,2-dihydroquinoline-3-carbaldehyde [ No CAS ]
[ 172078-33-0 ]
6-(3,5-dimethylisoxazol-4-yl)-3-((5-hydroxyindolin-1-yl)methyl)-7-methoxy-1-(pyridin-2-ylmethyl)quinolin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6%		To a stirred solution of 6-(3,5-dimethylisoxazol-4-yl)-7-methoxy-2-oxo-l-(pyri- din-2-ylmethyl)-l,2-dihydroquinoline-3-carbaldehyde (intermediate- le) (0.2 g, 0.51 mmol) in titanium isopropoxide (5 mL) was added <strong>[172078-33-0]indolin-5-ol</strong> (0.1 g, 0.77 mmol) followed by stirring at RT for 16 h. After stirring, methanol (20 mL) was added to the mixture at 0 C followed by NaCNBH4 (0.16 g, 2.56 mmol). The mixture was stirred at RT for 2 h. The mixture was then quenched with ammonium hydroxide and the solids were filtered off. The filtrate was extracted with EtOAc (100 mL x 2), washed with water (100 mL) and brine (100 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was purified to get the title compound as pale brown solid (0.016 g, 6 %). 1H NMR (400 MHz, CDC13) delta 8.60 (d, J=4.8 Hz, 1H), 7.86 (s, 1H), 7.67 (t, J=7.8 Hz, 1H), 7.34 (d, J=7.8 Hz, 1H), 7.27 (s, 1H), 7.23-7.20 (m, 2H), 6.69 (s, 1H), 6.60-6.48 (m, 2H), 5.74 (s, 2H), 4.29 (s, 2H), 3.79 (s, 3H), 3.61-3.59 (m, 2H), 3.10-3.00 (m, 2H), 2.25 (s, 3H), 2.11 (s, 3H); LC-MS: m/z 509.3 (M+H)+.

Reference： [1]Patent: WO2017/1733,2017,A1 .Location in patent: Page/Page column 85

51
[ 417721-36-9 ]
[ 172078-33-0 ]
C₂₃H₂₂N₄O₃S [ No CAS ]

Reference： [1]Patent: EP3293177,2018,A1

52
[ 417721-36-9 ]
[ 172078-33-0 ]
C₁₉H₁₇N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 120℃; for 2h;	Compound 1E (100 mg, 423 mmol), compound 24A (63 mg, 465 mmol) and cesium carbonate (303 mg, 930mmol) were added to NMP (1 mL). The reaction solution was heated to 120 °C and stirred for 2 hours, and then thereaction was quenched with water, and extracted with ethyl acetate (3 x 10 ml). The organic layer was washed withsaturated NaCl solution, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The residue waschromatographed on a silica gel plate (dichloromethane/methanol = 10: 1, Rf = 0.2) and purified to give compound 24B(yellow solid, 80 mg, 57percent).LCMS (ESI) m/z: 336.1(M+1)+

Reference： [1]Patent: EP3293177,2018,A1 .Location in patent: Paragraph 0217; 0219

53
[ 172078-33-0 ]
[ 98-95-3 ]
[ 1953-54-4 ]
[ 62-53-3 ]

Reference： [1]Green Chemistry,2020,vol. 22,p. 1996 - 2010

54
[ 81-20-9 ]
[ 172078-33-0 ]
[ 1953-54-4 ]
[ 87-62-7 ]

Reference： [1]Green Chemistry,2020,vol. 22,p. 1996 - 2010

55
[ 141519-77-9 ]
[ 172078-33-0 ]
1-[(1-chloro-5-isoquinolyl)sulfonyl]indolin-5-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63.6%	With triethylamine; In dichloromethane; for 12.0h;Inert atmosphere;	Compound 2-2: To a solution of <strong>[141519-77-9]1-chloroisoquinoline-5-sulfonylchloride</strong> (0.4 g, 1.53 mmol) in DCM (10 mL) was added TEA (318 muL, 2.29 mmol) and indolin-5-ol (226.9 mg, 1.68 mmol). The mixture was stirred at 25 C. for 12 h under an N2 atmosphere. The reaction mixture was filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether:ethyl acetate=10:1 to 1:1). Compound 2-2, 1-[(1-chloro-5-isoquinolyl) sulfonyl]indolin-5-ol (350 mg, 970.0 mumol, 63.6% yield), was obtained as a yellow solid.

Reference： [1]Patent: US2020/140412,2020,A1 .Location in patent: Paragraph 0098-0100

56
[ 172078-33-0 ]
(R)-5,6,8,9-tetrahydro-3H-indolo[7a,1-a]isoquinolin-3-one [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

57
[ 172078-33-0 ]
(R)-5,6,8,9-tetrahydro-3H-indolo[7a,1-a]isoquinolin-3-one [ No CAS ]
5,6,8,9-tetrahydro-3H-indolo[7a,1-a]isoquinolin-3-one [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

58
[ 905710-81-8 ]
[ 172078-33-0 ]
(R)-11-fluoro-5,6,8,9-tetrahydro-3H-indolo[7a,1-a]isoquinolin-3-one [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

59
2-(2-bromo-5-(trifluoromethyl)phenyl)acetaldehyde [ No CAS ]
[ 172078-33-0 ]
(R)-11-(trifluoromethyl)-5,6,8,9-tetrahydro-3H-indolo[7a,1-a]isoquinolin-3-one [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

60
[ 1241405-24-2 ]
[ 172078-33-0 ]
(R)-12-methyl-5,6,8,9-tetrahydro-3H-indolo[7a,1-a]isoquinolin-3-one [ No CAS ]
12-methyl-5,6,8,9-tetrahydro-3H-indolo[7a,1-a]isoquinolin-3-one [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

61
2-(2-bromo-5-methoxyphenyl)acetaldehyde [ No CAS ]
[ 172078-33-0 ]
(R)-11-methoxy-5,6,8,9-tetrahydro-3H-indolo[7a,1-a]isoquinolin-3-one [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

62
[ 90841-59-1 ]
[ 172078-33-0 ]
11,12-dimethoxy-5,6,8,9-tetrahydro-3H-indolo[7a,1-a]isoquinolin-3-one [ No CAS ]
(R)-11,12-dimethoxy-5,6,8,9-tetrahydro-3H-indolo[7a,1-a]isoquinolin-3-one [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

63
[ 889115-21-3 ]
[ 172078-33-0 ]
(R)-5,6,8,9-tetrahydro-3H-[1,3]dioxolo[4,5-g]indolo[7a,1-a]isoquinolin-3-one [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

64
[ 172078-33-0 ]
[ 107408-16-2 ]
(R)-2,3,5,6-tetrahydro-1H,8H-benzo[3,4]azepino[2,1-i]indol-8-one [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2020,vol. 38,p. 683 - 689

65
[ 51359-78-5 ]
[ 172078-33-0 ]
4-((indoline-5-oxy)methyl)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.29%		Take one 100mL eggplant-shaped bottle, add 0.54g (4.00mmol) <strong>[172078-33-0]5-hydroxyindoline</strong>, 1.36g (4.16mmol) Cs2CO3 and 30mL absolute ethanol, stir at room temperature for 1h, and 0.79g (3.97mmol) 3a- 1 or 3a-2 and 0.10g (0.60mmol) KI were put into the reaction solution, and the reaction was refluxed at 80 for more than 4h. The progress of the reaction was monitored by thin layer chromatography until the <strong>[172078-33-0]5-hydroxyindoline</strong> point completely disappeared, and vacuum distillation The solvent was removed, and the residue was a pale yellow solid. The residue was dissolved with 30 mL each of water and ethyl acetate. The liquid was separated. The aqueous phase was extracted twice with ethyl acetate, 15 mL each time. The organic phases were combined, washed with water, and washed with saturated brine. Dry over anhydrous sodium sulfate, filter to remove sodium sulfate, the filtrate was distilled under reduced pressure to remove the solvent, the residue was sampled with 100-200 mesh silica gel, and separated by column chromatography (PE:EA=12:1 elution) to give a light yellow oil 4-((Indoline-5-)oxymethyl) benzaldehyde (4d-3, 0.72g, yield 71.29%) or 3-((Indoline-5-)oxymethyl) benzaldehyde (4d-4, 0.77g, yield 76.24%).

Reference： [1]Patent: CN111217776,2020,A .Location in patent: Paragraph 0289-0293

66
[ 82072-23-9 ]
[ 172078-33-0 ]
3-((indoline-5-oxy)methyl)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76.24%		Take one 100mL eggplant-shaped bottle, add 0.54g (4.00mmol) <strong>[172078-33-0]5-hydroxyindoline</strong>, 1.36g (4.16mmol) Cs2CO3 and 30mL absolute ethanol, stir at room temperature for 1h, and 0.79g (3.97mmol) 3a- 1 or 3a-2 and 0.10g (0.60mmol) KI were put into the reaction solution, and the reaction was refluxed at 80 for more than 4h. The progress of the reaction was monitored by thin layer chromatography until the <strong>[172078-33-0]5-hydroxyindoline</strong> point completely disappeared, and vacuum distillation The solvent was removed, and the residue was a pale yellow solid. The residue was dissolved with 30 mL each of water and ethyl acetate. The liquid was separated. The aqueous phase was extracted twice with ethyl acetate, 15 mL each time. The organic phases were combined, washed with water, and washed with saturated brine. Dry over anhydrous sodium sulfate, filter to remove sodium sulfate, the filtrate was distilled under reduced pressure to remove the solvent, the residue was sampled with 100-200 mesh silica gel, and separated by column chromatography (PE:EA=12:1 elution) to give a light yellow oil 4-((Indoline-5-)oxymethyl) benzaldehyde (4d-3, 0.72g, yield 71.29%) or 3-((Indoline-5-)oxymethyl) benzaldehyde (4d-4, 0.77g, yield 76.24%).

Reference： [1]Patent: CN111217776,2020,A .Location in patent: Paragraph 0289-0293

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
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P230	Keep wetted
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P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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. 172078-33-0 ] {[proInfo.proName]}

Quality Control of [ 172078-33-0 ]

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[ 172078-33-0 ] Synthesis Path-Upstream 1~2

[ 172078-33-0 ] Synthesis Path-Downstream 1~66

Related Functional Groups of [ 172078-33-0 ]

Alcohols

Related Parent Nucleus of [ 172078-33-0 ]

Indolines

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[ 172078-33-0 ]

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[ 172078-33-0 ]