[ CAS No. 75927-49-0 ] {[proInfo.proName]}

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Quality Control of [ 75927-49-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 75927-49-0 ]

SDS Specification

Alternatived Products of [ 75927-49-0 ]

Product Details of [ 75927-49-0 ]

CAS No. :	75927-49-0	MDL No. :	MFCD00192492
Formula :	C₈H₁₅BO₂	Boiling Point :	-
Linear Structure Formula :	((CH₃)₄C₂O₂)BCHCH₂	InChI Key :	DPGSPRJLAZGUBQ-UHFFFAOYSA-N
M.W :	154.01	Pubchem ID :	5233012
Synonyms :

Calculated chemistry of [ 75927-49-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.04
TPSA :	18.46 ?2

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) :	0.0
Log Po/w (XLOGP3) :	2.06
Log Po/w (WLOGP) :	1.8
Log Po/w (MLOGP) :	0.76
Log Po/w (SILICOS-IT) :	0.92
Consensus Log Po/w :	1.11

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.03
Solubility :	1.45 mg/ml ; 0.0094 mol/l
Class :	Soluble
Log S (Ali) :	-2.08
Solubility :	1.29 mg/ml ; 0.00838 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.91
Solubility :	1.9 mg/ml ; 0.0123 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.05

Safety of [ 75927-49-0 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P240-P241-P242-P243-P261-P264-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P363-P370+P378-P403+P233-P501	UN#:	3272
Hazard Statements:	H225-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 75927-49-0 ]

* 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 [ 75927-49-0 ]
Downstream synthetic route of [ 75927-49-0 ]

[ 75927-49-0 ] Synthesis Path-Upstream 1~3

1
[ 623-73-4 ]
[ 75927-49-0 ]
[ 1215107-29-1 ]

Reference： [1] Patent: WO2010/30538, 2010, A2, . Location in patent: Page/Page column 212-213
[2] Patent: WO2011/112186, 2011, A1, . Location in patent: Page/Page column 211-212
[3] Patent: WO2015/52226, 2015, A1, . Location in patent: Paragraph 0187

2
[ 402-43-7 ]
[ 75927-49-0 ]
[ 1242770-50-8 ]

Reference： [1] New Journal of Chemistry, 2017, vol. 41, # 8, p. 3172 - 3176

3
[ 1813-97-4 ]
[ 75927-49-0 ]
[ 1242770-50-8 ]

Reference： [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3328 - 3333

[ 75927-49-0 ] Synthesis Path-Downstream 1~13

1
[ 10386-27-3 ]
[ 75927-49-0 ]
[ 98436-74-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;palladium diacetate; triphenylphosphine; In 1,4-dioxane; at 85℃; for 4h;Inert atmosphere;	Example A3. General experimental for the Suzuki coupling of aryl bromides or chlorides with boronic acidsGeneral Scheme:K2C03, Pd(OAc)2 Ph3P, dioxaneRepresentative SchePh3P, dioxaneA solution of the aryl bromide or aryl chloride (e.g., 6-bromonicotinonitrile, 1 equiv), 4,4,5,5-tetramethyl -2-vinyl-l,3,2- dioxaborolane (2 equiv), K2C03 (2 equiv), Pd(AcO)2 (0.4 equiv) and PI13P (0.8 equiv) in 1,4-dioxane was stirred under N2 at 85 °C until the reaction was complete (approximately 4 h). After cooling to room temperature, the mixture was quenched with water (50 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over Na2S04 and concentrated under reduced pressure. The crude vinyl-containing product (e.g., 2-vinylisonicotinonitrile) was purified by silica gel chromatography.

Reference： [1]Patent: WO2012/170845,2012,A2 .Location in patent: Page/Page column 80

2
[ 452-92-6 ]
[ 75927-49-0 ]
5-ethenyl-2,4-difluoroaniline [ No CAS ]

Reference： [1]Patent: WO2016/31255,2016,A1 .Location in patent: Page/Page column 172

3
[ 75927-49-0 ]
[ 131818-17-2 ]
[ 633327-37-4 ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 3172 - 3176

4
[ 26163-07-5 ]
[ 75927-49-0 ]
(E)-N,N-dimethyl-5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)pyridin-2-amine [ No CAS ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 3172 - 3176

5
[ 84539-22-0 ]
[ 75927-49-0 ]
(E)-4-(5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)pyrimidin-2-yl)morpholine [ No CAS ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 3172 - 3176

6
[ 13534-90-2 ]
[ 75927-49-0 ]
[ 1255957-49-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In water; N,N-dimethyl-formamide; at 60℃;Inert atmosphere;	A mixture of compound 1 (237 mg, 1 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (154 mg, 1 mmol), aq. K3PO4 (3 mL, 1 M, 3 mmol) and Pd(dppf)Cl2 (73 mg, 0.1 mmol) in DMF (10 mL) was stirred at 60 C under N2 for 3 h. The reaction mixture was diluted with H2O and extracted with EA. The organic layer was washed with H2O, brine, dried over Na2SO4. After concentrated, the residue was purified by silica gel column chromatography (PE : EA = 30:1) to give the product of compound 2 (170 mg, yield: 92 %). 1H-NMR (CDCl3, 400 MHz) d 8.70 (s, 1H), 8.45 (d, J = 7.2Hz, 1H), 7.41 (d, J = 7.2Hz, 1H), 6.98 (q, J = 6.8Hz, 1H), 5.94 (d, J = 17.6Hz, 1H), 5.60 (d, J = 11.2Hz, 1H).

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 1373 - 1375

7
[ 65202-50-8 ]
[ 75927-49-0 ]
[ 1408335-07-8 ]

Yield	Reaction Conditions	Operation in experiment
84.02%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In N,N-dimethyl-formamide;Inert atmosphere;	A solution of Example 65D (600mg, 3.48mmol), vinyl pinacol borate (803.2mg, 5.22mmol), potassium carbonate(961.07mg, 6.95mmol) and Pd(PPh3)4 (602.66mg, 521.53mmol) in DMF (8mL) was stirred at 100°C for 5 hours undernitrogen atmosphere. The solution was cooled, filtered and concentrated in vacuo. The residue was purified by columnchromatography to give the title compound (500mg, yield 84.02percent). 1H NMR (400MHz, CHLOROFORM-d) ppm 8.18 (d,J=8.8 Hz, 1H), 7.72 (d, J=8.8 Hz, 1H), 7.16 (dd, J=11.0, 17.8 Hz, 1H), 6.44 (d, J=17.8 Hz, 1H), 5.85 (d, J=10.8 Hz, 1H),4.10 (s, 3H).

Reference： [1]Patent: EP3333157,2018,A1 .Location in patent: Paragraph 0398; 0399

8
[ 75927-49-0 ]
[ 820236-81-5 ]
methyl 2-fluoro-6-vinylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 2.01 g (8.63 mmol) of methyl2-bromo-6-fluorobenzoate in 20 ml of 1,4-dioxane and 4.0 ml of water, 2.80 g (26.4 mmol) of sodium carbonate and 2.90 ml (16.9 mmol) of 4,4,5,5-tetramethyl-2-vinyl-1,3,2- dioxaborolane were added in a nitrogen atmosphere and then stirred at room temperature for 10 minutes while argon gas was bubbled into the reaction solution. Subsequently, 1.02 g (0.883 mmol) of tetrakis(triphenylphosphine)palladium(0) was added thereto at room temperature and reacted at 90 C. for 4 hours with stirring. After completion of the reaction, the reaction solution was diluted with water, followed by extraction twice with ethyl acetate. The whole organic layer thus obtained was dried over anhydrous magnesium sulfate, then filtered, and concentrated under reduced pressure. The obtained concentration residue was subjected to preparative colunm chromatography (apparatus 1, silica gel, n-hexane:ethyl acetate=99: 1-8:2-97:3), and a fraction containing methyl 2-fluoro-6-vinylbenzoate was concentrated under reduced pressure and dried under reduced pressure. To a solution of the obtained concentration residue in 16 ml of 1,4-dioxane and 4.0 ml of water, 1.34 g (12.6 mmol) of sodium carbonate and 1.40 ml (8.16 mmol) of 4,4,5,5-tetramethyl-2-vinyl- 1 ,3,2-dioxaborolane were added in a nitrogen atmosphere and then stirred at room temperature for 10 minutes while argon gas was bubbled into the reaction solution. Subsequently, 446 mg (0.386 mmol) of tetrakis(triphenylphosphine)palladium(0) was added thereto at room temperature and reacted at 90 C. for 3 hours with stirring. Subsequently, 1.10 ml (6.41 mmol) of 4,4,5,5- tetramethyl-2-vinyl- 1 ,3,2-dioxaborolane and 133 mg (0.115 mmol) of tetrakis(triphenylphosphine)palladium(0) were added to the reaction solution and reacted at 90 C. for 3 hours with stirring. After completion of the reaction, the reaction solution was diluted with water, followed by extraction twice with ethyl acetate. The whole organic layer thus obtained was dried over anhydrous magnesium sulfate, then filtered, and concentrated under reduced pressure. The obtained concentration residue was subjected to preparative column chromatography (apparatus 1, silica gel, n-hexane:ethyl acetate=99: 1 -98:2-97:3), and a fraction containing methyl 2-fluoro-6-vinylbenzoate was concentrated under reduced pressure and dried under reduced pressure.

Reference： [1]Patent: US2018/186818,2018,A1 .Location in patent: Paragraph 1145; 1146; 1147; 1148; 1149

9
[ 1298031-94-3 ]
[ 75927-49-0 ]
6-chloro-2-methyl-8-(prop-1-en-2-yl)imidazo[1,2-b]pyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 2h;Inert atmosphere;	8-Bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (500 mg, 2.05 mmol, prepared according to example 43) was combined with vinylboronic acid pinacol ester (0.43 mL, 2.3 mmol), Pd(dppf)Cl2 (150 mg, 0.21 mmol) and K2C03 (850 mg, 6.15 mmol) in 1,4-dioxane (10 mL) and H20 (2 mL). The mixture was stirred at 90 C for 2 h under N2. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 10-20% EtOAc in petroleum ether to yield 6-chloro-2-methyl-8-(prop- l-en-2-yl)imidazo[l,2- b]pyridazine (300 mg, 77%). MS m/z 208.0, 210.0 [M+H]+.

Reference： [1]Patent: WO2018/226622,2018,A1 .Location in patent: Page/Page column 89; 194

10
[ 935-99-9 ]
[ 75927-49-0 ]
1-(5-chloro-2-vinylphenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In tetrahydrofuran; water; at 100℃; for 1h;Inert atmosphere; Microwave irradiation;	A mixture of 1 -(2-bromo-5-chlorophenyl)ethanone (10 g, 42.8 mmol), 4,4,5,5-tetramethyl-2- vinyl-1 ,3,2-dioxaborolane (9.89 g, 64.2 mmol), Pd(dppf)CI2 (3.13 g, 4.28 mmol) and potassium carbonate (1 1 .84 g, 86 mmol) in THF (40 mL) and H20 (20 mL) was stirred at 100 °C under N2 in a microwave apparatus for 1 h. Water was added and the mixture was extracted with ethyl acetate (3x50 mL). The combined organic layers were washed with saturated NaHCC , water and brine, then dried over MgS04 and filtered. The resulting residue was purified by silica gel flash chromatography (petroleum ether/EtOAc = 10/1 ) to give 1 -(5- chloro-2-vinylphenyl)ethanone (8 g, 39.9 mmol, 93 percent yield) as a yellow solid, m/z: [M + H]+ Calcd for CioHioCIO 181 .0; Found 181 .

Reference： [1]Patent: WO2019/63748,2019,A1 .Location in patent: Page/Page column 267

11
[ 145691-59-4 ]
[ 75927-49-0 ]
(3-bromo-5-ethenylphenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃;	Into a 100-mL round-bottom flask, was placed <strong>[145691-59-4](3,5-dibromophenyl)methanol</strong> (2 g, 7.52 mmol, 1.00 eq.), dioxane (40 mL), water(4 mL), 2-ethenyl-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1.2 g, 7.79 mmol, 1.00 eq.), Pd(PPh3)4 (900 mg, 0.78 mmol, 0.10 eq.), potassium carbonate (3.1 g, 22.43 mmol, 3.00 eq.). The resulting solution was stirred for 1 overnight at 100 C. The solids were filtered out. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 100 mL of H2O. The resulting solution was extracted with 3x100 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane. This resulted in 1.1 g (69%) of (3-bromo-5- ethenylphenyl)methanol as yellow oil.

Reference： [1]Patent: WO2019/99576,2019,A1 .Location in patent: Paragraph 0350

12
[ 18087-73-5 ]
[ 75927-49-0 ]
3-vinylimidazo[1,2-b]pyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70.5%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 100℃; for 1h;Inert atmosphere;	Add 3-bromoimidazo [1,2-b] pyridazine (9.9g, 0.05mol), Pd (pph3) 4 (2.89g, 2.5mmol), vinylboronic acid pinacol ester (8.47g, 0.055mol) And Na2CO3 solution (2M) (23mL, 0.05mol) were added to 1,4-dioxane (150mL). Under nitrogen protection, the temperature was raised to 100 C for 1h, and the reaction solution was poured into 200mL saturated NH4Cl aqueous solution, acetic acid. The organic phase was extracted with ethyl acetate (100 mL × 3), the organic phase was separated, dried over anhydrous sodium sulfate, filtered, and concentrated. The product was isolated by column chromatography on silica gel to obtain 5.1 g of the product, with a yield of 70.5%.
70.5%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 100℃; for 1h;	3-bromoimidazo [1,2-b] pyridazine (9.9 g, 0.05 mol), tetrakis (triphenylphosphonium) palladium (2.89 g, 2.5 mmol),Vinyl boronic acid pinacol ester (8.47g, 0.055mol) and Na2CO3 solution (2M) (23mL, 0.05mol) were added to 1,4-dioxane (150mL).The temperature was raised to 100 C for 1 hour. After the reaction was completed,Pour the reaction solution into 200 mL of saturated aqueous NH4Cl solution.Extracted with ethyl acetate (100mL × 3), separated the organic phase, dried over anhydrous sodium sulfate, and filtered.After concentration, 5.1 g of the product was isolated by column chromatography on silica gel with a yield of 70.5%.

Reference： [1]Patent: CN110372705,2019,A .Location in patent: Paragraph 0357-0358; 0360-0361
[2]Patent: CN110467620,2019,A .Location in patent: Paragraph 0357; 0359-0361; 0369; 0371-0373

13
[ 676448-17-2 ]
[ 75927-49-0 ]
t-butyl 4-vinyl-1H-indole-1-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 17117 - 17124

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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P233	Keep container tightly closed.
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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

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

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[ CAS No. 75927-49-0 ] {[proInfo.proName]}

Quality Control of [ 75927-49-0 ]

Related Doc. of [ 75927-49-0 ]

Product Details of [ 75927-49-0 ]

Calculated chemistry of [ 75927-49-0 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 75927-49-0 ]

Application In Synthesis of [ 75927-49-0 ]

[ 75927-49-0 ] Synthesis Path-Upstream 1~3

[ 75927-49-0 ] Synthesis Path-Downstream 1~13

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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