[ CAS No. 476004-81-6 ] {[proInfo.proName]}

Name: 476004-81-6|2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole|97%
Brand: Ambeed
SKU: A129724
Price: 16.0 USD
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Quality Control of [ 476004-81-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 476004-81-6 ]

SDS Specification

Alternatived Products of [ 476004-81-6 ]

Product Details of [ 476004-81-6 ]

CAS No. :	476004-81-6	MDL No. :	MFCD09751284
Formula :	C₁₄H₁₈BNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IAQBURSQTCOSBP-UHFFFAOYSA-N
M.W :	243.11	Pubchem ID :	11356935
Synonyms :

Calculated chemistry of [ 476004-81-6 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.43
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	74.77
TPSA :	34.25 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.6 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.07
Log Po/w (WLOGP) :	2.47
Log Po/w (MLOGP) :	1.49
Log Po/w (SILICOS-IT) :	2.42
Consensus Log Po/w :	1.89

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.59
Solubility :	0.0632 mg/ml ; 0.00026 mol/l
Class :	Soluble
Log S (Ali) :	-3.46
Solubility :	0.085 mg/ml ; 0.00035 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.89
Solubility :	0.00314 mg/ml ; 0.0000129 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.02

Safety of [ 476004-81-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P273-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335-H413	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 476004-81-6 ]

* 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 [ 476004-81-6 ]
Downstream synthetic route of [ 476004-81-6 ]

[ 476004-81-6 ] Synthesis Path-Upstream 1~9

1
[ 476004-81-6 ]
[ 26340-49-8 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 1, p. 140 - 143

2
[ 120-72-9 ]
[ 73183-34-3 ]
[ 476004-81-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; for 8 h; Inert atmosphere	[0117] An argon-purged, round-bottom flask was charged with diμ-metho obis(1 ,5- cyclooctadiene)diiridium(l) (64 mg, 0.096 mmol) and 4,4'-di-ferf-butyl-2,2'-bipyridine (52 mg, 0.19 mmol). The flask was evacuated and backfilled with argon. Indole (1.50 g, 12.8 mmol) and bis(pinacolato)diboron (1.62 g, 6.40 mmol) were added and the flask was again purged with argon. Dry hexane (38.5 mL) was then introduced and the mixture was stirred at room temperature under argon for 8 h. The reaction mixuture was concentrated under reduced pressure and the resulting residue was purified by column chromatography (Si0₂, 0-10percent EtOAc/hexanes) to give the title compound (2.66 g, 85percent yield). *H NMR (300 MHz, d₆-DMSO) δ 11.27 (s, 1H), 7.55 (d, J = 7.9 Hz, 1H), 7.38 (dd, J = 8.2, 0.8 Hz, 1 H), 7.15 - 7.06 (m, 1 H), 7.00 - 6.92 (m, 1 H), 6.90 - 6.87 (m, 1 H) and 1.32 (s, 12H).

Reference： [1] Journal of the American Chemical Society, 2015, vol. 137, # 7, p. 2665 - 2673
[2] Patent: WO2014/22744, 2014, A1, . Location in patent: Paragraph 0117
[3] Journal of the American Chemical Society, 2014, vol. 136, # 18, p. 6566 - 6569
[4] Dalton Transactions, 2015, vol. 44, # 29, p. 13007 - 13016
[5] Organic Letters, 2012, vol. 14, # 16, p. 4266 - 4269
[6] Angewandte Chemie - International Edition, 2018, [7] Angew. Chem., 2018, vol. 130, # 45, p. 15107 - 15111,5
[8] Tetrahedron Letters, 2002, vol. 43, # 32, p. 5649 - 5651
[9] Angewandte Chemie - International Edition, 2002, vol. 41, # 16, p. 3056 - 3058
[10] Tetrahedron, 2008, vol. 64, # 22, p. 4967 - 4971
[11] Angewandte Chemie - International Edition, 2002, vol. 41, # 16, p. 3056 - 3058
[12] Patent: US2011/275628, 2011, A1, . Location in patent: Page/Page column 18
[13] Organic Letters, 2013, vol. 15, # 1, p. 140 - 143
[14] ACS Catalysis, 2014, vol. 4, # 5, p. 1365 - 1375
[15] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 3241 - 3249
[16] Journal of the American Chemical Society, 2017, vol. 139, # 23, p. 7745 - 7748
[17] Organic Syntheses, 2005, vol. 82, p. 126 - 133

3
[ 120-72-9 ]
[ 25015-63-8 ]
[ 476004-81-6 ]

Reference： [1] Chemical Communications, 2003, # 23, p. 2924 - 2925
[2] Dalton Transactions, 2015, vol. 44, # 29, p. 13007 - 13016
[3] Journal of Molecular Catalysis A: Chemical, 2004, vol. 207, # 1, p. 21 - 25
[4] Organic Letters, 2012, vol. 14, # 16, p. 4266 - 4269
[5] Organic Syntheses, 2005, vol. 82, p. 126 - 133
[6] Advanced Synthesis and Catalysis, 2004, vol. 346, # 13-15, p. 1655 - 1660
[7] Tetrahedron, 2008, vol. 64, # 22, p. 4967 - 4971

4
[ 271-26-1 ]
[ 25015-63-8 ]
[ 476004-81-6 ]

Reference： [1] Chemical Communications, 2003, # 23, p. 2924 - 2925

5
[ 76-09-5 ]
[ 116491-57-7 ]
[ 476004-81-6 ]

Reference： [1] Organic Letters, 2005, vol. 7, # 13, p. 2523 - 2526

6
[ 120-72-9 ]
[ 476004-81-6 ]

Reference： [1] ACS Catalysis, 2018, vol. 8, # 7, p. 6216 - 6223

7
[ 73183-34-3 ]
[ 476004-81-6 ]

Reference： [1] ACS Catalysis, 2018, vol. 8, # 7, p. 6216 - 6223

8
[ 120-72-9 ]
[ 73183-34-3 ]
[ 476004-81-6 ]

Reference： [1] Journal of the American Chemical Society, 2010, vol. 132, # 12, p. 4068 - 4069

9
[ 120-72-9 ]
[ 73183-34-3 ]
[ 25015-63-8 ]
[ 71-43-2 ]
[ 24388-23-6 ]
[ 476004-81-6 ]

Reference： [1] Journal of the American Chemical Society, 2010, vol. 132, # 12, p. 4068 - 4069

[ 476004-81-6 ] Synthesis Path-Downstream 1~88

1
[ 76-09-5 ]
[ 116491-57-7 ]
[ 476004-81-6 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2523 - 2526

3
[ 1003-09-4 ]
[ 476004-81-6 ]
[ 55968-16-6 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 4967 - 4971

4
[ 271-26-1 ]
[ 25015-63-8 ]
[ 476004-81-6 ]

Reference： [1]Chemical Communications,2003,p. 2924 - 2925

5
[ 120-72-9 ]
[ 73183-34-3 ]
[ 25015-63-8 ]
[ 71-43-2 ]
2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole [ No CAS ]
[ 24388-23-6 ]
[ 476004-81-6 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 4068 - 4069

6
[ 120-72-9 ]
[ 73183-34-3 ]
2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole [ No CAS ]
[ 476004-81-6 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 4068 - 4069

7
cis-3-(8-amino-1-iodo-imidazo[1,5-a]pyrazin-3-yl)-cyclobutanol [ No CAS ]
[ 476004-81-6 ]
C₁₈H₁₇N₅O [ No CAS ]