[ CAS No. 1065181-58-9 ] {[proInfo.proName]}

Name: 1065181-58-9|Ethyl 5-bromo-1H-indole-7-carboxylate|98%
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Quality Control of [ 1065181-58-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1065181-58-9 ]

CAS No. :	1065181-58-9	MDL No. :	MFCD21608002
Formula :	C₁₁H₁₀BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YVPFHVKOHMYAHB-UHFFFAOYSA-N
M.W :	268.11	Pubchem ID :	59332585
Synonyms :

Calculated chemistry of [ 1065181-58-9 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.18
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	62.09
TPSA :	42.09 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.68
Log Po/w (XLOGP3) :	2.96
Log Po/w (WLOGP) :	3.11
Log Po/w (MLOGP) :	2.36
Log Po/w (SILICOS-IT) :	3.37
Consensus Log Po/w :	2.9

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.61
Solubility :	0.0654 mg/ml ; 0.000244 mol/l
Class :	Soluble
Log S (Ali) :	-3.51
Solubility :	0.0835 mg/ml ; 0.000311 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.62
Solubility :	0.00646 mg/ml ; 0.0000241 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.8

Safety of [ 1065181-58-9 ]

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 [ 1065181-58-9 ]

* 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 [ 1065181-58-9 ]
Downstream synthetic route of [ 1065181-58-9 ]

[ 1065181-58-9 ] Synthesis Path-Upstream 1~7

1
[ 1065181-58-9 ]
[ 860624-91-5 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 12, p. 1164 - 1169

2
[ 1065181-58-9 ]
[ 860624-89-1 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2018,

3
[ 1065181-58-9 ]
[ 860624-90-4 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2018,

4
[ 1065181-56-7 ]
[ 1065181-58-9 ]

Yield	Reaction Conditions	Operation in experiment
69%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform for 2 h; Inert atmosphere	Intermediate 4: Ethyl δ-bromo-IH-indole^-carboxylate. <n="69"/>DDQ (1 19.3 g. 525.7mmol) was added in several portions to a solution of ethyl 5-bromo- 2,3-dihydro-1 /-/-indole-7-carboxylate (129.1 g, 0.48 mmol) in CHCI₃ (1500 ml.) and the mixture was stirred for 2 h. The reaction was filtered and the solid was washed with CHCI₃ (3 x 500 ml_). The filtrate was washed with 5percent NaOH (3 x 500 ml_), H₂O (500 ml.) and brine (500 ml.) then dried over Na₂SO₄. The solution was evaporated and the residue was recrystallized with EtOH, giving 88 g (69percent) of the title compound. LC/MS: m/z 267.6 (M+H), Rt 1.14 min.

Reference： [1] Patent: WO2008/118724, 2008, A1, . Location in patent: Page/Page column 66-67
[2] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 12, p. 1164 - 1169

5
[ 143262-10-6 ]
[ 1065181-58-9 ]

Reference： [1] Patent: WO2008/118724, 2008, A1,
[2] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 12, p. 1164 - 1169

6
[ 1065181-52-3 ]
[ 1065181-58-9 ]

Reference： [1] Patent: WO2008/118724, 2008, A1,
[2] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 12, p. 1164 - 1169

7
[ 496-15-1 ]
[ 1065181-58-9 ]

Reference： [1] Patent: WO2008/118724, 2008, A1,

[ 1065181-58-9 ] Synthesis Path-Downstream 1~88

1
[ 496-15-1 ]
[ 1065181-58-9 ]

Reference： [1]Patent: WO2008/118724,2008,A1

2
tetrahydrothiophene-3-carbaldehyde [ No CAS ]
[ 1065181-58-9 ]
[ 1065183-53-0 ]

Yield	Reaction Conditions	Operation in experiment
56.4%		Intermediate 104:Ethyl 5-bromo-3-(tetrahydro-3-thienylmethyl)-1 H-indole-7-carboxylate.To a solution of tetrahydro-3-thiophenecarbaldehyde (5.0 g, 43.10 mmol) in dichloromethane (200 mL) was added TMS-OTf (15.4 mL, 86.26 mmol) and ethyl 5- bromo-1 H-indole-7-carboxylate (11.5 g, 43.10 mmol) dropwise at 0 0C. The mixture was stirred at 0 0C for 2h, and then triethylsilane was added at the same temperature, which was maintained for 2h. The reaction was warmed to 20 0C and stirred for 16h. Water was added, the layers were separated, and the organic layer was (Na2SO4),concentrated, and purified on silica gel (PE:EA = 50:1 ), giving 9g (56.4) of the title compound. 1H NMR (CDCI3): delta 1.43 (t, 3H), 2.08 (m, 1 H), 2.58 (m, 2H), 2.88 (m, 6H), 4.44 (q, 2H), 7.09 (s, 1 H), 7.89 (s, 1 H), 7.95 (s, 1 H), 9.65 (s, 1 H).

Reference： [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 123

3
[ 2323-13-9 ]
[ 1065181-58-9 ]
[ 1065182-83-3 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 72:(racem/cJ-Ethyl 5-bromo-3-(2,2-dimethyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7- carboxylate.2,2-Dimethyltetrahydro-4H-thiopyran-4-one (0.675 g, 4.68 mmol) was placed in a dried flask fitted up with an addition funnel, a septum and an argon inlet, and dissolved in dry DCM (15 mL), cooled to 0 0C, stirred, and then trimethylsilyl trifluoromethanesulfonate (1.692 mL, 9.36 mmol) was added dropwise through the addition funnel over 10 minutes. DCM (5 mL) was used to wash the addition funnel walls. To this mixture was added dropwise ethyl 5-bromo-1 H-indole-7- carboxylate (1.341 g, 5 mmol) in DCM (15 mL) over 2 hours. Then triethylsilane (2.98 mL, 18.73 mmol) was added in one portion. The mixture was stirred 2 h at 0 0C, and left stirring at 23 0C overnight. The reaction was <n="108"/>quenched with a saturated aqueous solution of sodium bicarbonate, and the resulting biphasic mixture extracted with DCM to give 2.1 15 g of the title compound. LC/MS: m/z 398.0 (M+H), Rt 1.49 min.

Reference： [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 105-106

4
[ 19090-03-0 ]
[ 1065181-58-9 ]
[ 1065182-38-8 ]

Yield	Reaction Conditions	Operation in experiment
40%		Intermediate 53:Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate.Dihydro-2H-thiopyran-3(4/-/)-one (0.217g, 1.86mmol) was dissolved in dichloromethane (23ml_) in an oven dried flask containing 3 A molecular sieves and stirred under argon at 00C. TMS-OTf (0.414g, 1.86mmol, 0.33 ml.) was added slowly to the mixture over 10 min.Ethyl 5-bromo-1 /-/-indole-7-carboxylate (0.5g, 1.86mmol) was dissolved in DCM (7ml_) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 3 hours between 0 and 10 0C. The reaction was cooled to 0 0C and triethylsilane (0.325g, 0.44ml_, 2.8mmol) was added all at once and the reaction was stirred at room temperature for 18 hours. The reaction was then quenched with a saturated sodium bicarbonate solution and extracted with DCM. The combined organics were washed with water. The combined aqueous layers were back-extracted with DCM. The combined organics were washed with brine, dried with MgSO4, and concentrated. The crude compound was purified on a Combiflash silica column with 5-25% EA/Hexane to give 0.279g (40%) of the title compound.LC/MS: m/z 369 (M+H), Rt 2.74 min.

Reference： [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 96
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

5
[ 143262-10-6 ]
[ 1065181-58-9 ]

Reference： [1]Patent: WO2008/118724,2008,A1
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

6
[ 1072-72-6 ]
[ 1065181-58-9 ]
[ 1065181-66-9 ]

Yield	Reaction Conditions	Operation in experiment
76%		The title compound can also be prepared according to the following procedure: TMSOTf (1.4 ml_, 7.7 mmol) was added dropwise to a solution of tetrahydro-4H-thiopyran- 4-one (0.88 g, 7.6 mmol) in DCM (80 ml.) in the presence of molecular sieves at 0 0C (bath temp). A solution of ethyl 5-bromo-1 /-/-indole-7-carboxylate (2 g, 7.4 mmol). in DCM (20 ml.) was added and the reaction was stirred for 15 min. Triethylsilane (2 ml_, 12.5 mmol) was added and the reaction was allowed to warm to room temperature overnight. Saturated aqueous Na2CO3 was added, the layers separated and the aqueous layer extracted with DCM. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The residue was washed with MeOH and dried in a vacuum oven, giving 2.07 g (76%) of the title compound.

Reference： [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 71
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

7
[ 1003-04-9 ]
[ 1065181-58-9 ]
[ 1065181-97-6 ]

Yield	Reaction Conditions	Operation in experiment
47%		Intermediate 25:Ethyl 5-bromo-3-(tetrahydro-3-thienyl)-1H-indole-7-carboxylate.Dihydro-3(2H)-thiophenone (0.381 g, 3.73mmol) was dissolved in dichloromethane (50ml) in an oven dried flask containing 3A molecular sieves and stirred under Argon at O0C. TMS-OTf (0.826g, 3.73mmol, 0.67 ml.) was added slowly to the mixture over 10 min. Ethyl 5-bromo-1 /-/-indole-7-carboxylate (1 g, 3.73mmol) was dissolved in DCM (6 ml.) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 30 min at 0 0C. Triethylsilane (0.651 g, 0.89ml, 5.59mmol) was then added all at once and the reaction was stirred at room temperature for 18 hours. The reaction was then quenched with a saturated sodium bicarbonate solution (35 ml.) and extracted with DCM (2 x 50 ml_). The combined organics were washed with water (2 x 100 ml_), brine, dried with MgSO4, and concentrated. The crude compound was purified on Combiflash silica column with 10% EA/Hexane to give 0.62Og (47%) of the title compound. LCMS m/z =355 (M+H), RT = 1.34 min.

Reference： [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 81

8
[ 2323-17-3 ]
[ 1065181-58-9 ]
[ 1065182-49-1 ]

Yield	Reaction Conditions	Operation in experiment
26%		Intermediate 59:Ethyl S-bromo-S^jtheta-dimethyltetrahydro^H-thiopyran^-ylJ-IH-indole-y-carboxylate.2,6-Dimethyltetrahydro-4H-thiopyran-4-one (0.293g, 2.03mmol) was dissolved in dichloromethane (35ml_) in an oven dried flask containing 3 A molecular sieves and stirred under argon at 0 0C. TMS-OTf (0.451 g, 2.03mmol, 0.36 ml.) was added slowly to the mixture over 10 min. Ethyl 5-bromo-1 /-/-indole-7-carboxylate (0.293g, 2.031 mmol) was dissolved in DCM (1OmL) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 3 hours between 0 and 10 0C. The reaction was cooled to 0 0C and triethylsilane (0.353 g, 0.485 ml_, 3.04 mmol) was then added all at once and the reaction was stirred at room temperature overnight. The reaction was then quenched with a saturated sodium bicarbonate solution, filtered, then extracted with DCM. The combined organics were washed with water. The combined aqueous layers were back-extracted with DCM. The combined organics were washed with brine, dried with MgSO4, and concentrated. The crude compound was purified on Combiflash silica column with 0-30% EA/DCM to give 0.212g (26%) of the the title compound. LC/MS: m/z 397 (M+H), Rt 1.51 min.

Reference： [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 99

9
[ 22072-22-6 ]
[ 1065181-58-9 ]
[ 1065182-26-4 ]

Yield	Reaction Conditions	Operation in experiment
24%		Intermediate 46: Ethyl 5-bromo-3-(4-thiepanyl)-1H-indole-7-carboxylate.To a solution of 4-thiepanone (900 mg, 6.9 mmol, 1.1 eq) in dry dichloromethane (30 ml.) was added activated molecular sieves (4 A, beads, spatula tip full) and the solution was cooled to O 0C using an ice water bath. Trimethylsilyl trifluromethanesulfonate (1.25 ml_, 6.9 mmol, 1.1 eq) was added dropwise to the ketone solution, followed by the dropwise addition of ethyl 5-bromo-1 /-/-indole-7-carboxylate (1.69g, 6.3 mmol, 1 eq) as a solution in dichloromethane (10 ml_). The reaction mixture was stirred at rt for 2h, then warmed to 35 0C for 45 minutes. The deep red reaction mixture was cooled to 0 0C and triethylsilane (2 ml_, 12.6 mmol, 2 eq) was added. The mixture was warmed to rt for 30 minutes, then was quenched by the addition of saturated aq. sodium bicarbonate. The aqueous layer was extracted with dichloromethane (2x50 ml_), and the combined organic extracts were dried over sodium sulfate, filtered through a thin pad of silica gel (to remove baseline impurities), eluting with 50% ethyl acetate in hexanes, and concentrated to afford the crude product as a yellow residue. The crude material was purified by lsco Combiflash, eluting with 0-30% ethyl acetate in hexanes (120 gram column). The title compound was obtained as a yellow residue (540 mg, 24%).

Reference： [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 92

10
[ 1065181-56-7 ]
[ 1065181-58-9 ]

Yield	Reaction Conditions	Operation in experiment
69%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In chloroform; for 2h;Inert atmosphere;	Intermediate 4: Ethyl delta-bromo-IH-indole^-carboxylate. <n="69"/>DDQ (1 19.3 g. 525.7mmol) was added in several portions to a solution of ethyl 5-bromo- 2,3-dihydro-1 /-/-indole-7-carboxylate (129.1 g, 0.48 mmol) in CHCI3 (1500 ml.) and the mixture was stirred for 2 h. The reaction was filtered and the solid was washed with CHCI3 (3 x 500 ml_). The filtrate was washed with 5% NaOH (3 x 500 ml_), H2O (500 ml.) and brine (500 ml.) then dried over Na2SO4. The solution was evaporated and the residue was recrystallized with EtOH, giving 88 g (69%) of the title compound. LC/MS: m/z 267.6 (M+H), Rt 1.14 min.

Reference： [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 66-67
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

11
[ 1065181-58-9 ]
[ 1065182-40-2 ]

Reference： [1]Patent: WO2008/118724,2008,A1
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

12
[ 1065181-58-9 ]
[ 1065182-43-5 ]

Reference： [1]Patent: WO2008/118724,2008,A1
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

13
[ 1065181-58-9 ]
[ 1065182-45-7 ]

Reference： [1]Patent: WO2008/118724,2008,A1
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

14
[ 1065181-58-9 ]
[ 1065182-51-5 ]

Reference： [1]Patent: WO2008/118724,2008,A1

15
[ 1065181-58-9 ]
[ 1065182-53-7 ]

Reference： [1]Patent: WO2008/118724,2008,A1

16
[ 1065181-58-9 ]
[ 1065182-56-0 ]

Reference： [1]Patent: WO2008/118724,2008,A1

17
[ 1065181-58-9 ]
[ 1065182-70-8 ]

Reference： [1]Patent: WO2008/118724,2008,A1
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

18
[ 1065181-58-9 ]
[ 1065182-92-4 ]

Reference： [1]Patent: WO2008/118724,2008,A1
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

19
[ 1065181-58-9 ]
[ 1065182-79-7 ]
[ 1065182-75-3 ]

Reference： [1]Patent: WO2008/118724,2008,A1

20
[ 1065181-58-9 ]
[ 1065182-85-5 ]

Reference： [1]Patent: WO2008/118724,2008,A1

21
[ 1065181-58-9 ]
[ 1065182-87-7 ]

Reference： [1]Patent: WO2008/118724,2008,A1

22
[ 1065181-58-9 ]
[ 1065183-09-6 ]

Reference： [1]Patent: WO2008/118724,2008,A1

23
[ 1065181-58-9 ]
[ 1065183-11-0 ]

Reference： [1]Patent: WO2008/118724,2008,A1

24
[ 1065181-58-9 ]
[ 1065183-14-3 ]

Reference： [1]Patent: WO2008/118724,2008,A1

25
[ 1065181-58-9 ]
5-bromo-3-[cis-2-(1-methylethyl)-1,1-dioxidotetrahydro-2H-thiopyran-4-yl]-1H-indole-7-carboxamide [ No CAS ]
5-bromo-3-[trans-2-(1-methylethyl)-1,1-dioxidotetrahydro-2H-thiopyran-4-yl]-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2008/118724,2008,A1

26
[ 1065181-58-9 ]
[ 1065183-43-8 ]

Reference： [1]Patent: WO2008/118724,2008,A1

27
[ 1065181-58-9 ]
[ 1065183-45-0 ]

Reference： [1]Patent: WO2008/118724,2008,A1

28
[ 1065181-58-9 ]
[ 1065183-54-1 ]

Reference： [1]Patent: WO2008/118724,2008,A1

29
[ 1065181-58-9 ]
[ 1065183-56-3 ]

Reference： [1]Patent: WO2008/118724,2008,A1

30
[ 1065181-58-9 ]
[ 1065183-59-6 ]

Reference： [1]Patent: WO2008/118724,2008,A1

31
[ 1065181-58-9 ]
[ 1065175-72-5 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

32
[ 1065181-58-9 ]
[ 1065181-68-1 ]

Reference： [1]Patent: WO2008/118724,2008,A1
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

33
[ 1065181-58-9 ]
[ 1065181-70-5 ]

Reference： [1]Patent: WO2008/118724,2008,A1
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

34
[ 1065181-58-9 ]
[ 1065181-79-4 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

35
[ 1065181-58-9 ]
[ 1065181-82-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

36
[ 1065181-58-9 ]
[ 1065181-91-0 ]

Reference： [1]Patent: WO2008/118724,2008,A1
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

37
[ 1065181-58-9 ]
[ 1065181-94-3 ]

Reference： [1]Patent: WO2008/118724,2008,A1
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

38
[ 1065181-58-9 ]
[ 1065181-98-7 ]

Reference： [1]Patent: WO2008/118724,2008,A1

39
[ 1065181-58-9 ]
[ 1065179-21-6 ]

Reference： [1]Patent: WO2008/118724,2008,A1

40
[ 1065181-58-9 ]
[ 1065182-29-7 ]

Reference： [1]Patent: WO2008/118724,2008,A1

41
[ 1065181-58-9 ]
[ 1065182-32-2 ]

Reference： [1]Patent: WO2008/118724,2008,A1

42
[ 1065181-58-9 ]
[ 1065182-33-3 ]

Reference： [1]Patent: WO2008/118724,2008,A1

43
[ 1065181-58-9 ]
[ 1065185-56-9 ]

Reference： [1]Patent: WO2008/118724,2008,A1

44
[ 1065181-58-9 ]
[ 71747-22-3 ]
[ 1065183-06-3 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 80:Ethyl 5-Bromo-3-[2-(1 -methylethyl)tetrahydro-2H-thiopyran-4-yl]-1 H-indole-7- carboxylate.2-(1-methylethyl)tetrahydro-2H-thiopyran-4-one (1.185 g, 7.49 mmol) was dissolved in dry dichloromethane (DCM) (20 ml_), cooled in an ice bath to ca 0 0C, and stirred under argon. Trimethylsilyl trifluoromethanesulfonate (2.71 ml_, 14.98 mmol) was added dropwise over 10 minutes, and dry DCM (5 ml.) was used to wash in the last of the trimethylsilyltrifuoromethanesulfonate. To this mixture was added dropwise, a solution of ethyl 5-bromo-1 H-indole-7-carboxylate (2.145 g, 8 mmol) in dry DCM (20 ml_), and then an additional portion of dry DCM (5 ml.) was used to wash the last of ethyl 5-bromo-1 H- indole-7-carboxylate into the reaction. Triethylsilane (4.77 ml_, 30.0 mmol) was added to the reaction in one portion. The resulting mixture was stirred 2h at 0 0C, and left stirring at 23 0C overnight. The reaction was diluted with saturated aqueous sodium bicarbonate, and the resulting biphasic mixture was extracted with DCM, dried (MgSO4) and the DCM was removed in vacuo to give the title compound as a dark yellow oil. LC/MS: m/z 414.3 (M+H), Rt 1.58 min.

Reference： [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 110

45
[ 1065181-58-9 ]
[ 76625-84-8 ]
ethyl 5-bromo-3-(2-phenyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylate [ No CAS ]
ethyl 5-bromo-3-(2-phenyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 87:Ethyl 5-bromo-3-(2-phenyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylate.To a solution of 2-phenylthian-4-one (SJTU) (0.900 g, 4.68 mmol) in dichloromethane (DCM) (15 ml_), cooled on an ice bath to 0 0C, under argon, was added dropwise trimethylsilyl trifluoromethanesulfonate (1.807 ml_, 10 mmol) over 10 minutes, an additional portion of dry DCM (5 ml.) was used to wash the addition funnel walls. To this mixture ethyl 5-bromo-1 H-indole-7- carboxylate (1.340 g, 5.00 mmol) was added dropwise, in solution with of dry DCM, over 2 hours. Finally, triethylsilane (3.19 ml_, 20 mmol) was added in one portion and the mixture was stirred 2 h at ca 0 0C, and left stirring at 23 0C 16 h. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate, and the resulting biphasic mixture partitioned with DCM to afford 2.21 g of brow gummy oil. LCMS of product may indicate an overlapping mixture of ca 5:2 major to minor isomers (cis/trans). LC/MS: m/z 448.1 (M+H), Rt 3.23 min.

Reference： [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 114

46
[ 16892-50-5 ]
[ 1065181-58-9 ]
ethyl 5-bromo-3-(8-thiabicyclo[3.2.1]oct-3-yl)-1H-indole-7-carboxylate [ No CAS ]
ethyl 5-bromo-3-(8-thiabicyclo[3.2.1]oct-3-yl)-1H-indole-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 31 :Ethyl 5-bromo-3-(8-thiabicyclo[3.2.1]oct-3-yl)-1H-indole-7-carboxylate.To a solution of 8-thiabicyclo[3.2.1]octan-3-one (1.33 g, 9.32 mmol, 1 eq) in dry dichloromethane (50 mL) was added a spatula tip full of activated 4A molecular sieves (beads). The ketone solution was cooled to 0 0C, and trimethylsilyl triflate (1.7 mL, 9.41 mmol, 1 eq) was added dropwise followed by a solution of ethyl 5-bromo-1 H-indole-7- carboxylate (2.5 g, 9.32 mmol, 1 eq) in dichloromethane (25 mL). The mixture was stirred at 23 0C overnight, then was cooled to 23 0C and triethylsilane (2.3 mL, 14.4 mmol, 1.5 eq) was added in a single portion. The reaction was stirred at 23 0C for 1.5h, then quenched by the addition of saturated aqueous sodium bicarbonate. The mixture was extracted with dichloromethane, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The crude product was purified by lsco Combiflash, 120 gram column, eluting with 0-30% ethyl acetate in hexanes. The ethyl 5-bromo-3-(8- thiabicyclo[3.2.1]oct-3-yl)-1 /-/-indole-7-carboxylate was obtained as a mixture of isomers (2.38 g, 65%).

Reference： [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 84

47
[ 61571-06-0 ]
[ 1065181-58-9 ]
[ 1065183-42-7 ]

Yield	Reaction Conditions	Operation in experiment
66%		Intermediate 98:Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-3-ylmethyl)-1H-indole-7-carboxylate.To a 100 ml. three-necked flask equipped with an addition funnel was added tetrahydro- 2H-thiopyran-3-carbaldehyde (2.50 g, 0.019 mol) and dry DCM (30 ml_). Trimethylsilyl trifluoromethanesulfonate was put in the addition funnel. The mixture was cooled down to0 0C with an ice bath and put under nitrogen atmosphere. Trimethylsilyl trifluoromethanesulfonate was added over 15 min, and 10 ml. of dry DCM were used to wash the addition funnel walls. A solution of ethyl 5-bromo-1 H-indole-7-carboxylate in 30 ml. dry DCM was added to the mixture for 2 h at 0 0C, and the mixture was then stirred at room tmperature overnight. An aqueous solution of sodium bicarbonate was added, the layers were separated, and the mixture was extracted with DCM (3 x 100 ml_). The combined organic layers were dried (Na2SO4), filtered, and purified by chromatography, eluting with a mixture of PE:EA (50:1-30:1 ) to afford 4.82 g (66.0%) of the title compound. 1H NMR NMR (CDCI3) delta 1.1 1-1.15 (m,1 H),1.43 (t,3H),1.65-1.71 (m,2H),1.83-1.87 (m,1 H),1.96-2.03 (m,2H), 2.32-2.38 (m,1 H), 2.51-2.59 (m, 2H),2.66-2.68 (m, 2H), 4.40-4.45 (q,2H), 7.07 (d, 1 H),7.77 (d, 1 H), 7.95 (d, 1 H), 9.64 (s, 1 H).

Reference： [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 120

48
[ 1065181-52-3 ]
[ 1065181-58-9 ]

Reference： [1]Patent: WO2008/118724,2008,A1
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

49
[ 63853-74-7 ]
[ 1065181-58-9 ]
ethyl 5-bromo-3-(5-oxopyrrolidin-2-yl)-1H-indole-7-carboxylate [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

50
[ 1065181-58-9 ]
[ 70687-35-3 ]
ethyl 5-bromo-3-(1-methyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxylate [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

51
[ 67-56-1 ]
[ 3437-29-4 ]
[ 1065181-58-9 ]
[ 98-80-6 ]
3-(3,3-dimethyl-5-oxopyrrolidin-2-yl)-5-phenyl-1H-indole-7-carboxamide [ No CAS ]
3-(4,4-dimethyl-5-oxopyrrolidin-2-yl)-5-phenyl-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

52
[ 67-56-1 ]
[ 3437-29-4 ]
[ 1065181-58-9 ]
ethyl 5-bromo-3-(4,4-dimethyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxylate [ No CAS ]
ethyl 5-bromo-3-(3,3-dimethyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxylate [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

53
[ 67-56-1 ]
[ 3437-29-4 ]
[ 1065181-58-9 ]
5-bromo-3-(4,4-dimethyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxylic acid [ No CAS ]
5-bromo-3-(3,3-dimethyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxylic acid [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

54
[ 67-56-1 ]
[ 3437-29-4 ]
[ 1065181-58-9 ]
5-bromo-3-(4,4-dimethyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxamide [ No CAS ]
5-bromo-3-(3,3-dimethyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

55
[ 1065181-58-9 ]
[ 16892-50-5 ]
ethyl 5-bromo-3-(8-thiabicyclo[3.2.1]oct-3-yl)-1H-indole-7-carboxylate [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

56
[ 1065181-58-9 ]
3-(3-oxocyclopentyl)-5-phenyl-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

57
[ 1065181-58-9 ]
5-bromo-3-(5-oxopyrrolidin-2-yl)-1H-indole-7-carboxylic acid [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

58
[ 1065181-58-9 ]
5-bromo-3-(5-oxopyrrolidin-2-yl)-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

59
[ 1065181-58-9 ]
[ 860624-89-1 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

60
[ 1065181-58-9 ]
3-(5-oxopyrrolidin-2-yl)-5-phenyl-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

61
[ 1065181-58-9 ]
5-bromo-3-(1-methyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxylic acid [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

62
[ 1065181-58-9 ]
5-bromo-3-(1-methyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

63
[ 1065181-58-9 ]
C₂₀H₁₉N₃O₂ [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

64
[ 1065181-58-9 ]
5-phenyl-3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

65
[ 1065181-58-9 ]
5-phenyl-3-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

66
[ 1065181-58-9 ]
3-(4-oxocyclohexyl)-5-phenyl-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

67
[ 1065181-58-9 ]
3-(3-oxocyclohexyl)-5-phenyl-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

68
[ 1065181-58-9 ]
[ 1065181-86-3 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

69
[ 1065181-58-9 ]
[ 1065181-89-6 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

70
[ 1065181-58-9 ]
[ 1065181-90-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

71
[ 1065181-58-9 ]
[ 1065179-27-2 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

72
[ 1065181-58-9 ]
1-(1,1-dimethylethyl) 7-ethyl 5-bromo-3-(8-thiabicyclo[3.2.1]oct-3-yl)-1H-indole-1,7-dicarboxylate [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

73
[ 1065181-58-9 ]
[ 1065520-79-7 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

74
[ 1065181-58-9 ]
[ 1065182-04-8 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

75
[ 1065181-58-9 ]
[ 1065520-80-0 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

76
[ 1065181-58-9 ]
[ 1065182-07-1 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

77
[ 1065181-58-9 ]
[ 1065520-81-1 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

78
[ 1065181-58-9 ]
[ 1065182-12-8 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

79
[ 1065181-58-9 ]
3-[(3-endo)-8,8-dioxido-8-thiabicyclo[3.2.1]oct-3-yl]-5-phenyl-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

80
[ 1065181-58-9 ]
3-[(3-exo)-8,8-dioxido-8-thiabicyclo[3.2.1]oct-3-yl]-5-phenyl-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

81
[ 1065181-58-9 ]
3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-5-phenyl-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

82
[ 1065181-58-9 ]
[ 1065175-86-1 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

83
[ 1065181-58-9 ]
[ 860624-90-4 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

84
[ 1065181-58-9 ]
[ 1065182-65-1 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

85
[ 1065181-58-9 ]
[ 1065182-67-3 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

86
[ 1065181-58-9 ]
3-(2,2-dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-phenyl-1H-indole-7-carboxamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

87
[ 1065181-58-9 ]
[ 1065182-75-3 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

88
[ 1065181-58-9 ]
[ 1065182-79-7 ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169

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Ghs Precautionary Statements

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Response
Code	Phrase
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P321
P322
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P378
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P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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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.
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P370 + P376	In case of fire: Stop leak if safe to Do so.
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Storage
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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. 1065181-58-9 ] {[proInfo.proName]}

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[ 1065181-58-9 ] Synthesis Path-Upstream 1~7

[ 1065181-58-9 ] Synthesis Path-Downstream 1~88

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Bromides

Esters

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[ 1065181-58-9 ]

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[ 1065181-58-9 ]