[ CAS No. 923197-75-5 ] {[proInfo.proName]}

Name: 923197-75-5|(6-Bromo-1H-indol-2-yl)methanol|95%
Brand: Ambeed
SKU: A243006
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Quality Control of [ 923197-75-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 923197-75-5 ]

SDS Specification

Alternatived Products of [ 923197-75-5 ]

Product Details of [ 923197-75-5 ]

CAS No. :	923197-75-5	MDL No. :	MFCD08445239
Formula :	C₉H₈BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CNSVVCNALIWZAK-UHFFFAOYSA-N
M.W :	226.07	Pubchem ID :	13567957
Synonyms :

Calculated chemistry of [ 923197-75-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.11
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	52.13
TPSA :	36.02 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) :	-6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.94
Log Po/w (XLOGP3) :	1.89
Log Po/w (WLOGP) :	2.27
Log Po/w (MLOGP) :	1.68
Log Po/w (SILICOS-IT) :	3.02
Consensus Log Po/w :	2.16

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.92
Solubility :	0.271 mg/ml ; 0.0012 mol/l
Class :	Soluble
Log S (Ali) :	-2.27
Solubility :	1.22 mg/ml ; 0.00538 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.97
Solubility :	0.0241 mg/ml ; 0.000106 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.58

Safety of [ 923197-75-5 ]

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 [ 923197-75-5 ]

* 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 [ 923197-75-5 ]
Downstream synthetic route of [ 923197-75-5 ]

[ 923197-75-5 ] Synthesis Path-Upstream 1~2

1
[ 16732-65-3 ]
[ 923197-75-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4 h; Stage #2: With water; sodium hydroxide In tetrahydrofuran at 0℃;	To a solution of 6-bromo-1H-indole-2-carboxylic acid (1.00 g, 4.20 mmol) in THF (20.0 mL) was added LiAlH₄ (1.0 M in THF, 4.20 mL, 4.20 mmol) dropwise at 0° C. The reaction mixture was stirred for 4 h while warming to room temperature. The reaction was quenched with water and 15percent aqueous NaOH at 0° C. to form a precipitate which was filtered through Celite. The filtrate was extracted with EtOAc (3*). The extracts were dried over Na₂SO₄, filtered and concentrated under reduced pressure to give the title compound (696 mg, 73percent) as a yellow solid: ¹H NMR (500 MHz, CDCl₃) δ 7.51 (s, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.20 (dd, J=8.0, 1.6 Hz, 1H), 6.38 (s, 1H), 4.83 (d, J=5.6 Hz, 2H).

Reference： [1] Liebigs Annalen der Chemie, 1986, # 3, p. 438 - 455
[2] Patent: US2012/157469, 2012, A1, . Location in patent: Page/Page column 28-29
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 2, p. 364 - 377

2
[ 103858-53-3 ]
[ 923197-75-5 ]

Reference： [1] Synthesis (Germany), 2015, vol. 47, # 13, p. 1913 - 1921

[ 923197-75-5 ] Synthesis Path-Downstream 1~25

1
[ 16732-65-3 ]
[ 923197-75-5 ]

Yield	Reaction Conditions	Operation in experiment
73%		To a solution of 6-bromo-1H-indole-2-carboxylic acid (1.00 g, 4.20 mmol) in THF (20.0 mL) was added LiAlH4 (1.0 M in THF, 4.20 mL, 4.20 mmol) dropwise at 0 C. The reaction mixture was stirred for 4 h while warming to room temperature. The reaction was quenched with water and 15% aqueous NaOH at 0 C. to form a precipitate which was filtered through Celite. The filtrate was extracted with EtOAc (3*). The extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (696 mg, 73%) as a yellow solid: 1H NMR (500 MHz, CDCl3) delta 7.51 (s, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.20 (dd, J=8.0, 1.6 Hz, 1H), 6.38 (s, 1H), 4.83 (d, J=5.6 Hz, 2H).

Reference： [1]Liebigs Annalen der Chemie,1986,p. 438 - 455
[2]Patent: US2012/157469,2012,A1 .Location in patent: Page/Page column 28-29
[3]Journal of Medicinal Chemistry,2014,vol. 57,p. 364 - 377
[4]Patent: EP3421465,2019,A1
[5]Patent: WO2019/99402,2019,A1

2
[ 923197-75-5 ]
[ 105191-12-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With Dess-Martin periodane; In dichloromethane; at 20℃; for 0.5h;	(6-Bromo-1H-indol-2-yl)methanol (80 mg, 0.35 mmol) and dess-martin periodinane (178 mg, 0.42 mmol) were dissolved in dichloromethane (10 mL), and it was stirred for 30 minutes at room temperature. The reaction mixture was diluted with ethyl acetate, and it was washed with 10% sodium thiosulfate, saturated NaHC03and brine. The organic layer was dried over Na2S04, and it was concentrated under reduced pressure. The residue was purified on an ISCO chromatograph (0-10% ethyl acetate/hexane) to give product as a white solid (78 mg, 100%);1H NMR (300 MHz) (CDCb) d 9.86 (s, 1H), 9.23 (bs, 1H), 7.65 (s, 1H), 7.61 (d, J= 9 Hz, 1H), 7.29 (d, j= 9 Hz, 1H), 7.26-7.25 (m, 1H).
87.6%	With manganese(IV) oxide; In acetonitrile; at 20℃;	Compound TDI01155-2 (600 mg, 2.65 mmol) was dissolved in acetonitrile (20 mL), MnO2 (692 mg, 7.96 mmol)was added, and the reaction was stirred at room temperature overnight. Thin layer chromatography (petroleum ether :ethyl acetate=5:1) and LC-MS assay indicated the reaction was complete. The reaction solution was concentrated underreduced pressure, and the residue was purified by column chromatography (petroleum ether : ethyl acetate= 10:1 to1:1) to afford compound TDI01155-3 (520 mg, yellow solid, yield: 87.6%).1HNMR (400 MHz, CDCl3) delta 9.86 (s, 1H), 9.22 (s, 1H), 7.65 (s, 1H), 7.61 (d, J = 8.4 Hz, 1H), 7.30-7.28 (m, 1H), 7.25(br, 1H). MS m/z (ESI): 224.0/226.0 [M+H].
55%	With manganese(IV) oxide; In tetrahydrofuran; at 0 - 20℃; for 24.0h;	To a suspension of (6-bromo-1H-indol-2-yl)methanol (696 mg, 3.00 mmol) in THF (25.0 mL) was added MnO2 (3.20 g, 37.0 mmol) at 0 C. The reaction mixture was stirred for 24 h at room temperature. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to give the title compound (371 mg, 55%) as an orange solid: 1H NMR (500 MHz, CDCl3) delta 9.86 (s, 1H), 9.07 (br s, 1H), 7.64 (s, 1H), 7.61 (d, J=8.5 Hz, 1H), 7.29 (dd, J=8.5, 1.5 Hz, 1H), 7.24 (d, J=1.0 Hz, 1H).

Reference： [1]Patent: WO2019/99402,2019,A1 .Location in patent: Page/Page column 81; 82-83
[2]Patent: EP3421465,2019,A1 .Location in patent: Paragraph 0186; 0188
[3]Liebigs Annalen der Chemie,1986,p. 438 - 455
[4]Patent: US2012/157469,2012,A1 .Location in patent: Page/Page column 29
[5]Journal of Medicinal Chemistry,2014,vol. 57,p. 364 - 377
[6]Angewandte Chemie - International Edition,2020,vol. 59,p. 442 - 448
Angew. Chem.,2020,vol. 132,p. 450 - 456,7

3
[ 923197-75-5 ]
[ 105190-92-9 ]

Reference： [1]Liebigs Annalen der Chemie,1986,p. 438 - 455

4
[ 923197-75-5 ]
[ 105190-94-1 ]

Reference： [1]Liebigs Annalen der Chemie,1986,p. 438 - 455

5
[ 923197-75-5 ]
[ 105190-93-0 ]

Reference： [1]Liebigs Annalen der Chemie,1986,p. 438 - 455

6
[ 923197-75-5 ]
[ 1382774-60-8 ]