[ CAS No. 957061-13-1 ] {[proInfo.proName]}

Name: 957061-13-1|2-(4-(3-Bromopropoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|97%
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Quality Control of [ 957061-13-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 957061-13-1 ]

SDS Specification

Alternatived Products of [ 957061-13-1 ]

Product Details of [ 957061-13-1 ]

CAS No. :	957061-13-1	MDL No. :	MFCD09258657
Formula :	C₁₅H₂₂BBrO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YSXHRXGAAAOXSO-UHFFFAOYSA-N
M.W :	341.05	Pubchem ID :	44119764
Synonyms :

Calculated chemistry of [ 957061-13-1 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.6
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	86.89
TPSA :	27.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	4.0
Log Po/w (WLOGP) :	3.15
Log Po/w (MLOGP) :	2.3
Log Po/w (SILICOS-IT) :	3.16
Consensus Log Po/w :	2.52

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.37
Solubility :	0.0147 mg/ml ; 0.000043 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.28
Solubility :	0.0178 mg/ml ; 0.0000521 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.77
Solubility :	0.000579 mg/ml ; 0.0000017 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.37

Safety of [ 957061-13-1 ]

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 [ 957061-13-1 ]

* 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.

Downstream synthetic route of [ 957061-13-1 ]

[ 957061-13-1 ] Synthesis Path-Downstream 1~5

1
[ 109-64-8 ]
[ 269409-70-3 ]
[ 957061-13-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate In acetonitrile at 70℃; for 7h;	1 4-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenol (CAS No. 269409-70-3) (10.5 g, 47 mmol) was dissolved in dry CH3CN (200 niL) and dry, pulverized K2CO3 (10.4 g, 75 mmol) was introduced. 1,3-dibromopropane (38.ImL, 375 mmol) was added dropwise, and the reaction mixture was heated at 700C for 7 h under a nitrogen atmosphere. The cooled reaction mixture was filtered and the filtrate was evaporated to an oily residue, which was applied to a column of silica gel. Elution initially with hexanes, gradually increasing polarity to a mixture of hexanes/ ethyl acetate (25:1, 20:1 and 10:1) as eluent, provided the title compound (13.93 g, 86%) which crystallized on standing to a white solid, m.p. 62-650C.

Reference： [1]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - WO2009/97306, 2009, A1 Location in patent: Page/Page column 27

2
[ 957061-13-1 ]
[ 41720-98-3 ]
[ 1005403-35-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium carbonate; In acetonitrile; at 78℃; for 36h;	2-[4-(3-Bromopropoxy)phenyl]-4,4,5,5-tetramethyl-[l,3,2]-dioxaborolane (20.47 g, 60 mmol), (i?)-2-methylpyrrolidine hydrochloride (7.663 g, 63 mmol) and dry, pulverized K2CO3 (24.96 g, 180 mmol) were mixed in dry CH3CN (650 mL). After stirring for 12h at 78°C under a nitrogen atmosphere, the reaction mixture was cooled and further (R)-2- methylpyrrolidine hydrochloride (10.0 g, 82 m mol) was introduced and heating at 78°C was continued for 24 h. The reaction mixture was cooled, filtered and the filtrate was evaporated. Chromatography on silica gel, eluting initially with CH2Cl2, then with a mixture of CH2Cl2 /EtOH/ aq. NH3 (290:10:1) and later with a (90:10:1) and (40:10:1) mixture of these solvents <n="29"/>provided the title compound (17.44 g, 84percent). The material crystallized on seeding. A sample was converted into a hydrochloride salt, m.p. 212-214°C.

Reference： [1]Patent: WO2009/97306,2009,A1 .Location in patent: Page/Page column 27-28

3
[ 957061-13-1 ]
[ 75-04-7 ]
[ 1201789-52-7 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In tetrahydrofuran at 150℃; for 1h; Microwave irradiation;	102.1 682 mg of 4-(3-bromopropoxy)benzeneboronic acid pinacolate, 2.0 mL of a 2 M solution of ethylamine in tetrahydrofuran, 2.6 g of caesium carbonate and 6 mL of tetrahydrofuran are introduced into a microwave reactor of suitable size. The mixture is irradiated for 1 hour at 150° C. The medium is diluted with ethyl acetate and washed three times with water. The organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure to give 525 mg of N-ethyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propan-1-amine 91 in the form of a brown oil, which is used in crude form in the following step.UPLC-SQD: Rt (min)=0.68; [M+H]+: m/z 306.

Reference： [1]Current Patent Assignee: SANOFI - US2011/178053, 2011, A1 Location in patent: Page/Page column 74

4
[ 55276-43-2 ]
[ 957061-13-1 ]
[ 1201790-15-9 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In tetrahydrofuran; at 150℃; for 1h;Microwave irradiation;	A suspension of 2-[4-(3-bromo-propoxy)phenyl]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (350 mg, 1.03 mmol), 1-(methylsulfonyl)piperazine (185 mg, 1.13 mmol) and caesium carbonate (336 mg, 1.03 mmol) in tetrahydrofuran (3.0 ml) is heated at 150 C. by microwave for 1 hour. The reaction medium is then concentrated to dryness and the residue is washed with water and triturated with toluene and then with ether to give the expected product 137 (520 mg) in the form of a whitish gel.MS: m/z=424.2 (ES+).1H NMR (300 MHz, CDCl3) delta ppm 7.75 (d, 2H), 7.25 (s, 1H), 6.85 (d, 2H), 4.04 (t, 2H), 3.25 (t, 4H), 2.79 (s, 3H), 3.62-3.50 (m, 6H), 1.94 (p, 2H), 1.32 (s, 12H).

Reference： [1]Patent: US2011/178053,2011,A1 .Location in patent: Page/Page column 100

5
[ 1186220-73-4 ]
[ 957061-13-1 ]
tert-butyl (3-methoxy-4-((4-methyl-1-(3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)propyl)piperidin-4-yl)carbamoyl)phenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 12h;

Reference： [1]Willmann, Michael; Hegger, Julian; Neumaier, Bernd; Ermert, Johannes [ACS Medicinal Chemistry Letters, 2021, vol. 12, # 5, p. 738 - 744]

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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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.
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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.
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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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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H226	Flammable liquid and vapour
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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. 957061-13-1 ] {[proInfo.proName]}

Quality Control of [ 957061-13-1 ]

Related Doc. of [ 957061-13-1 ]

Product Details of [ 957061-13-1 ]

Calculated chemistry of [ 957061-13-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 957061-13-1 ]

Application In Synthesis of [ 957061-13-1 ]

[ 957061-13-1 ] Synthesis Path-Downstream 1~5

Related Functional Groups of [ 957061-13-1 ]

Organoboron

Aryls

Bromides

Ethers

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 957061-13-1 ]