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[ CAS No. 72316-17-7 ]

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2D 3D

Chemical Structure| 72316-17-7

Chemical Structure| 72316-17-7

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Quality Control of [ 72316-17-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 72316-17-7 ]

SDS

Alternatived Products of [ 72316-17-7 ]

Product Details of [ 72316-17-7 ]

CAS No. :	72316-17-7	MDL No. :	MFCD03427284
Formula :	C₉H₁₁BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	161.99 g/mol	Pubchem ID :	6019835
Synonyms :

Calculated chemistry of of [ 72316-17-7 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.11
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	50.63
TPSA :	40.46 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) :	-5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.83
Log Po/w (WLOGP) :	0.91
Log Po/w (MLOGP) :	1.17
Log Po/w (SILICOS-IT) :	0.18
Consensus Log Po/w :	0.82

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.24
Solubility :	0.942 mg/ml ; 0.00582 mol/l
Class :	Soluble
Log S (Ali) :	-2.3
Solubility :	0.812 mg/ml ; 0.00501 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.75
Solubility :	2.85 mg/ml ; 0.0176 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.96

Safety of [ 72316-17-7 ]

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 [ 72316-17-7 ]

* 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 [ 72316-17-7 ]
Downstream synthetic route of [ 72316-17-7 ]

[ 72316-17-7 ] Synthesis Path-Upstream 1~5

1
[ 766-97-2 ]
[ 274-07-7 ]
[ 72316-17-7 ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: for 18 h; Reflux Stage #2: at 20℃; for 4 h;	[00140] 1-Ethynyl-4-methylbenzene (0.50 mL, 3.94 mmol, 1.00 eq) and catecholborane (0.50 mL, 4.73 mmol, 1 .20 eq) were dissolved in THF (1 .5 mL) and the mixture was refluxed for 18h. The solvent was evaporated and then H20 (1 mL) was added. The suspension was vigorously stirred for 4 h at room temperature. The solid was filtered and recrystallized with water. (E)-5-phenylpent-1-en-1-ylboronic acid (309.4 mg, 1.90 mmol, 48percent) was then filtered and dried under vacuum.1H NMR (400 MHz, DMSO-d6) OH /ppm 7.73 (5, 2H), 7.36 (d, J= 7.9 Hz, 2H), 7.18 (d, J= 7.9 Hz, 2H), 6.05 (d, J= 18.3 Hz, 1H), 2.31 (5, 3H).13C NMR (101 MHz, DMSO) Oc /ppm: 146.2, 138.4, 135.4, 129.8 (20), 127.0 (20), 21 .3.

Reference： [1] Patent: WO2016/198836, 2016, A1, . Location in patent: Paragraph 00140
[2] Organic Letters, 2014, vol. 16, # 13, p. 3444 - 3447

2
[ 766-97-2 ]
[ 72316-17-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 11, p. 2803 - 2807
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 13, p. 2133 - 2138
[3] Angewandte Chemie - International Edition, 2011, vol. 50, # 2, p. 519 - 522
[4] Australian Journal of Chemistry, 2011, vol. 64, # 1, p. 62 - 67
[5] Organic and Biomolecular Chemistry, 2015, vol. 13, # 26, p. 7136 - 7139
[6] Advanced Synthesis and Catalysis, 2018, vol. 360, # 19, p. 3667 - 3671

3
[ 766-97-2 ]
[ 72316-17-7 ]

Reference： [1] Patent: EP1018514, 2000, A1,

4
[ 149777-84-4 ]
[ 72316-17-7 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 26, p. 7136 - 7139
[2] Advanced Synthesis and Catalysis, 2018, vol. 360, # 19, p. 3667 - 3671

5
[ 174153-82-3 ]
[ 72316-17-7 ]

Reference： [1] Australian Journal of Chemistry, 2011, vol. 64, # 1, p. 62 - 67

[ 72316-17-7 ] Synthesis Path-Downstream 1~7

1
[ 76-09-5 ]
[ 72316-17-7 ]
[ 149777-84-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With diethyl ether at 20℃;

Reference： [1]Koolmeister, Tobias; Södergren, Mikael; Scobie, Martin [Tetrahedron Letters, 2002, vol. 43, # 34, p. 5965 - 5968]

2
[ 766-97-2 ]
[ 274-07-7 ]
[ 72316-17-7 ]

Yield	Reaction Conditions	Operation in experiment
48%		[00140] 1-Ethynyl-4-methylbenzene (0.50 mL, 3.94 mmol, 1.00 eq) and catecholborane (0.50 mL, 4.73 mmol, 1 .20 eq) were dissolved in THF (1 .5 mL) and the mixture was refluxed for 18h. The solvent was evaporated and then H20 (1 mL) was added. The suspension was vigorously stirred for 4 h at room temperature. The solid was filtered and recrystallized with water. (E)-5-phenylpent-1-en-1-ylboronic acid (309.4 mg, 1.90 mmol, 48%) was then filtered and dried under vacuum.1H NMR (400 MHz, DMSO-d6) OH /ppm 7.73 (5, 2H), 7.36 (d, J= 7.9 Hz, 2H), 7.18 (d, J= 7.9 Hz, 2H), 6.05 (d, J= 18.3 Hz, 1H), 2.31 (5, 3H).13C NMR (101 MHz, DMSO) Oc /ppm: 146.2, 138.4, 135.4, 129.8 (20), 127.0 (20), 21 .3.

Reference： [1]Patent: WO2016/198836,2016,A1 .Location in patent: Paragraph 00140
[2]Organic Letters,2014,vol. 16,p. 3444 - 3447

3
[ 72316-17-7 ]
[ 41658-03-1 ]
[ 1620636-42-1 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 7391 - 7398

4
[ 13484-50-9 ]
[ 72316-17-7 ]
2,3,5,6-tetrakis((E)-4-methylstyryl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium phosphate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; catacxium A In 1,4-dioxane at 100℃; for 20h; Inert atmosphere;	6.1.17. Synthesis of tetraalkenylpyrazines. General procedure: An argon-flushed glass pressure tube was charged with Pd(dba)2 (0.005 mmol, 2 mol %), CataCXium A (0.01 mmol, 4 mol %), 2 (54.4 mg, 0.25 mmol), the appropriate alkenylboronic acid or pinacol ester (2 mmol, 8.0 equiv), K3PO4 (2 mmol, 8.0 equiv) and anhydrous 1,4-dioxane (4 mL). The tube was sealed with a Teflon cap and the reaction mixture was stirred at 100°C for 20 h. Resulting mixture was cooled down to room temperature, diluted with water and extracted with dichloromethane. The combined organic layers were dried over Na2SO4, filtered and the solvent was evaporated. After, the crude residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent. Gained solids in the end, were washed with cold hexane to give pure orange coloured products.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

5
[ 149777-84-4 ]
[ 72316-17-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium periodate; ammonium acetate In water; acetone Inert atmosphere;
	Stage #1: 4,4,5,5-tetramethyl-2-[(E)-2-p-tolylethenyl]-1,3,2-dioxaborolane With sodium periodate In tetrahydrofuran; water for 0.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃;

Reference： [1]Feng, Chao; Wang, Hong; Xu, Liang; Li, Pengfei [Organic and Biomolecular Chemistry, 2015, vol. 13, # 26, p. 7136 - 7139]
[2]Liu, Shiwen; Zeng, Xiaojun; Hammond, Gerald B.; Xu, Bo [Advanced Synthesis and Catalysis, 2018, vol. 360, # 19, p. 3667 - 3671]

6
[ 18791-78-1 ]
[ 72316-17-7 ]
4-[2-(4-methylphenyl)ethenyl]thiophene-3-carbaldehyde [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 3682 - 3688

7
[ 72316-17-7 ]
[ 183267-04-1 ]
[ 1552284-52-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With [2,2]bipyridinyl; copper (I) iodide; anhydrous sodium carbonate In acetonitrile at 60℃; for 12h; Inert atmosphere; stereospecific reaction;	(II) General procedure for copper(I)-Promoted Triuoromethylthiolation of Styreneboronic acid with N-trifluoromethylthiosuccinimide General procedure: To a 25 mL flask charged with aryl vinyl boric acid (1.0 equiv, 0.3 mmol), N-trifluoromethylthiosuccinimide (1.5 equiv), CuI (10 mmol%), Na2CO3 (4.0 equiv) and bpy (20 mmol%) was slowly added CH3CN (5 mL) by syringe at room temperature under N2 atmosphere. The reaction mixture was stirred at 60 °C for 12 hours (monitored by TLC). After cooling to room temperature, the suspension was filtered through a short pad of celite and the adsorbent was washed with DCM (2×5 mL). Then the filtrate was further washed with water (10 mL) and saturated NaCl solution (10 mL), dried over Na2SO4 and concentrated under vacuum. The residue was purified by silica gel flash column chromatography using EtOAc/PE (V/V = 1/15) as eluent to afford the products.

Reference： [1]Zheng, Changge; Ma, Mingyu; Huang, Shuai; Jiang, Chao; Liu, Yang; Fu, Yingying; Zhao, Kui; Feng, Ruilong; Hong, Jianquan [Tetrahedron Letters, 2022, vol. 103]

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P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
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P202	Do not handle until all safety precautions have been read and understood.
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P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
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.
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Code	Phrase
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P320
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P321
P322
P330	Rinse mouth.
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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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.
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P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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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.
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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.
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P370 + P378	In case of fire:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere