[ CAS No. 99873-30-0 ] {[proInfo.proName]}

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Quality Control of [ 99873-30-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 99873-30-0 ]

SDS Specification

Alternatived Products of [ 99873-30-0 ]

Product Details of [ 99873-30-0 ]

CAS No. :	99873-30-0	MDL No. :	MFCD16997652
Formula :	C₈H₉BrO	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	CAMRWHABCOLYHJ-UHFFFAOYSA-N
M.W :	201.06	Pubchem ID :	15007732
Synonyms :

Calculated chemistry of [ 99873-30-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.94
TPSA :	20.23 ?2

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) :	-4.83 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.03
Log Po/w (XLOGP3) :	3.8
Log Po/w (WLOGP) :	2.72
Log Po/w (MLOGP) :	2.88
Log Po/w (SILICOS-IT) :	2.81
Consensus Log Po/w :	2.85

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.86
Solubility :	0.0278 mg/ml ; 0.000138 mol/l
Class :	Soluble
Log S (Ali) :	-3.92
Solubility :	0.0242 mg/ml ; 0.00012 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.47
Solubility :	0.068 mg/ml ; 0.000338 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.18

Safety of [ 99873-30-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 99873-30-0 ]

* 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 [ 99873-30-0 ]
Downstream synthetic route of [ 99873-30-0 ]

[ 99873-30-0 ] Synthesis Path-Upstream 1~1

1
[ 620-17-7 ]
[ 99873-30-0 ]

Yield	Reaction Conditions	Operation in experiment
7.25 g	With N-Bromosuccinimide In chloroform at 0 - 20℃; for 2 h;	At 0°C cooling in ice, a mixture of 7.33g of 3-ethylphenol and 600mL of chloroform was added 10.7g of N-bromosuccinimide. After the temperature was raised to room temperature and stirred for 2 hours, The reaction solution was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 7.25g of 4-bromo-3-ethylphenol (Referred to as 45A).
7.25 g	With N-Bromosuccinimide In chloroform at 0 - 20℃; for 2 h; Cooling with ice	Reference Production Example 45 (0707) While stirring a mixture of 7.33 g of 3-ethylphenol and 600 mL of chloroform under ice cooling at 0° C., 10.7 g of N-bromosuccinimide was added. After raising the temperature to room temperature and stirring for 2 hours, the reaction solution was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 7.25 g of 4-bromo-3-ethylphenol (referred to as 45A). (0708) ¹H-NMR (CDCl₃) δ: 7.37 (1H, d, J=8.2 Hz), 6.90 (1H, d, J=2.1 Hz), 6.69 (1H, dd, J=8.2, 2.1 Hz), 5.48 (1H, s), 2.61 (2H, q, J=7.6 Hz), 1.24 (3H, t, J=7.6 Hz).

Reference： [1] Patent: WO2011/34828, 2011, A1, . Location in patent: Page/Page column 84
[2] Patent: EP2177513, 2010, A1, . Location in patent: Page/Page column 28
[3] Patent: CN105392779, 2016, A, . Location in patent: Paragraph 1351; 1352; 1353; 1354
[4] Patent: US2016/159755, 2016, A1, . Location in patent: Paragraph 0707; 0708

[ 99873-30-0 ] Synthesis Path-Downstream 1~10

Yield	Reaction Conditions	Operation in experiment
80%		Example 24(e) 3-1H-Benzoimidazol-2-yl-6-(2-ethyl-4-hydroxyphenyl)-1H-indazole Example 24 (e) was prepared in a similar manner to that described for Example 24(a), except that 4-bromo-3-ethyl-phenol, prepared in 80% yield according to the procedure described by Carreno et. al., Syn. Lett., 11, 1241-42 (1997) for the synthesis of 4-bromo-3-methyl-phenol, was used instead of 4-bromo-2-methoxy-5-methyl-phenol in step (vi). 1H NMR (300 MHz, DMSO-d6) delta 13.66 (s, 1H), 13.02 (s, 1H), 9.43 (s, 1H), 8.49 (d, 1H, J=8.4 Hz), 7.72 (d, 1H, J=6.9 Hz), 7.53 (d, 1H, J=6.9 Hz), 7.44 (s, 1H), 7.18-7.25 (m, 3H), 7.06 (d, 1H, J=8.1 Hz), 6.75 (d, 1H, J=2.1 Hz), 6.66 (dd, 1H, J=8.1, 2.1 Hz), 2.50 (q, 2H, J=7.5 Hz), 1.04 (t, 3H, J=7.5 Hz). MS (ES) [m+H]/z calc'd 355, found 355; [m-H]/z calc'd 353, found 353.

3
[ 620-17-7 ]
[ 99873-30-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-Bromosuccinimide; trifluorormethanesulfonic acid; In acetonitrile; at -30 - 20℃; for 12.0h;Inert atmosphere;	To a solution of 3-ethylphenol (22, 1.22 g, 10 mmol) in acetonitrile (CH3CN, 15mL) at 30 C were added sequentially with trifluoromethanesulfonic acid (TfOH,N-bromosuccinimide (NBS, 1.79 g, 10 mmol). The resultingreaction mixture was allowed to warm up to room temperature, and then stirred atroom temperature for 12 hours. The mixture was added sequentially with water (10mL) and diethyl ether (10 mL). The aqueous phase was extracted with diethyl ether (3x 20 mL). The combined organic phases were washed sequentially with saturatedaqueous sodium sulfite solution (Na2SO3, 20 mL) and brine (20 mL), dried overanhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure.The residue was purified by column chromatography (20% ethyl acetate in petroleumether) silica gel to afford 4-bromo-3-ethylphenol (23) as a white solid (1.89 g).Yield: 94%; m.p. = 51 53 C; 1H NMR (400 MHz, CDCl3): = 7.36 (d, J = 8.6Hz, 1H), 6.74 (d, J = 2.9 Hz, 1H), 6.56 (dd, J = 8.6, 3.0 Hz, 1H), 5.28 (s, 1H), 2.69 (q,J = 7.6 Hz, 2H), 1.20 (t, J = 7.5 Hz, 3H); 13C NMR (100 MHz, CDCl3): =154.7, 144.6, 133.3, 116.4, 114.8, 114.5, 29.3, 13.9; max = 3342, 2969,2932, 2873, 1577, 1468, 1439, 1285, 1236, 1161, 1058, 1027, 863, 807 cm-1. HRMS(ESI): m/z calcd for C8H9BrNaO [M+Na]+: 222.9729; found: 222.9737.
36%	With bromine; acetic acid;	Step 1 : 4-Bromo-3-ethylphenolTo a solution of 3-ethylphenol (3.0 g, 24.6 mmol) in acetic acid (20 ml) was added bromine (4 g, 22 mmol) in acetic acid (10 ml) dropwise over 5 minutes. The mixture was stirred at room temperature for 18 hours. The mixture was poured into water (100 ml) and was extracted with ethyl acetate (100 ml). The organic layer was washed with aqueous sodium bicarbonate and then water, dried over magnesium sulfate and filtered. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel using 100% heptane and then 9: 1 heptane: ethyl acetate to give the title compound as an oil (1.6 g, 36%).
	With tetra-N-butylammonium tribromide; In methanol; dichloromethane; at 20℃; for 1.0h;Inert atmosphere;	Example 13 4-bromo-3-ethylphenol Under argon atmosphere, to the mixture of 3-ethylphenol(11.2g), methylene chloride(30mL), and methanol(20mL), tetra-n-butylammonium tribromide (24.9g) was added and stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate and the organic layer was washed with a 1N hydrochloric acid, water and saturated brine solution and was dried by anhydrous magnesium sulphate. The title compound (11.2 g) having the following physical data was obtained by removing the solvent. TLC:Rf 0.49(n-hexane:ethyl acetate:acetic acid=1:4); 1H-NMR: (CDCl3) delta 1.22, 2.69, 4.92, 6.57, 6.74, 7.37.

7.25 g	With N-Bromosuccinimide; In chloroform; at 0 - 20℃; for 2.0h;	At 0C cooling in ice, a mixture of 7.33g of 3-ethylphenol and 600mL of chloroform was added 10.7g of N-bromosuccinimide. After the temperature was raised to room temperature and stirred for 2 hours, The reaction solution was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 7.25g of 4-bromo-3-ethylphenol (Referred to as 45A).
7.25 g	With N-Bromosuccinimide; In chloroform; at 0 - 20℃; for 2.0h;Cooling with ice;	Reference Production Example 45 (0707) While stirring a mixture of 7.33 g of 3-ethylphenol and 600 mL of chloroform under ice cooling at 0 C., 10.7 g of N-bromosuccinimide was added. After raising the temperature to room temperature and stirring for 2 hours, the reaction solution was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 7.25 g of 4-bromo-3-ethylphenol (referred to as 45A). (0708) 1H-NMR (CDCl3) delta: 7.37 (1H, d, J=8.2 Hz), 6.90 (1H, d, J=2.1 Hz), 6.69 (1H, dd, J=8.2, 2.1 Hz), 5.48 (1H, s), 2.61 (2H, q, J=7.6 Hz), 1.24 (3H, t, J=7.6 Hz).

Reference： [1]Natural Product Research,2019,vol. 33,p. 2911 - 2916
[2]Patent: WO2011/34828,2011,A1 .Location in patent: Page/Page column 84
[3]Patent: EP2177513,2010,A1 .Location in patent: Page/Page column 28
[4]Patent: CN105392779,2016,A .Location in patent: Paragraph 1351; 1352; 1353; 1354
[5]Patent: US2016/159755,2016,A1 .Location in patent: Paragraph 0707; 0708

4
[ 502434-59-5 ]
[ 99873-30-0 ]
[ 1116624-31-7 ]

Yield	Reaction Conditions	Operation in experiment
	With cesium chloride; In N,N-dimethyl-formamide; at 70℃;Inert atmosphere;	Example 14 (2S)-2-(4-bromo-3-ethylphenoxy)methyl-4-methyl-3,4-dihydro-2H-1,4-benzoxazine Under an argon atmosphere, to the mixture of the compound synthesised in Example 13 (11.2 g), the compound synthesised in Example 7 (16.9 g), and N,N-dimethylformamide(50mL), cesium chloride(18.2 g) was added and stirred overnight at 70C. The reaction mixture was diluted with ethyl acetate and the organic layer was washed with a 1N hydrochloric acid, water and saturated brine solution, and was dried with anhydrous magnesium sulphate. The title compound (17.0 g) having the following physical data was obtained by purifying the residue obtained by removing the solvent with silica gel column chromatography (n-hexane:ethyl acetate=6:1). TLC:Rf 0.49(n-hexane:ethyl acetate:acetic acid=1:6); 1H-NMR: (CDCl3) delta 1.22, 2.69, 2.91, 3.23, 3.38, 4.09, 4.18, 4.61, 6.63, 6.82, 7.39.

Reference： [1]Patent: EP2177513,2010,A1 .Location in patent: Page/Page column 28-29

5
[ 99873-30-0 ]
[ 183158-34-1 ]
[ 1279015-58-5 ]

Yield	Reaction Conditions	Operation in experiment
39%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 6.0h;Reflux;	Step 2: 2-Ethyl-2',3'-dimethyl-biphenyl-4-olA mixture of <strong>[99873-30-0]4-bromo-3-ethylphenol</strong> (1.6 g, 7.96 mmol), 2,3-dimethylphenylboronic acid (1.2 g, 7.96 mmol), tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.86 mmol) and a 2M sodium carbonate solution (6 ml) in 1 ,2-dimethoxyethane(70 ml) was heated at reflux for 6 hours. The mixture was cooled and was poured into an aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate (150 ml). The organic layer was washed with water, dried over magnesium sulfate and filtered. The concentrated filtrate was purified by flash chromatography on silica gel using 100% heptane, then 9: 1 heptane:ethyl acetate to provide the title compound (0.7 g, 39%).

Reference： [1]Patent: WO2011/34828,2011,A1 .Location in patent: Page/Page column 85

6
[ 99873-30-0 ]
[ 1279014-72-0 ]

Reference： [1]Patent: WO2011/34828,2011,A1

7
[ 99873-30-0 ]
[ 1279015-59-6 ]

Reference： [1]Patent: WO2011/34828,2011,A1

8
[ 99873-30-0 ]
[ 76513-69-4 ]
{2-[(4-bromo-3-ethylphenoxy)methoxy]ethyl}(trimethyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 18.0h;	Preparation 344(2-((4-l3romo-3-ethylphenoxy)methoxy)ethyl)trim- ethylsilane10778] To a solution of <strong>[99873-30-0]4-bromo-3-ethylphenol</strong> (9 g, 44.8 mmol) in DCM (100 mE) was added DIPEA (8.6 mE, 49.3 mmol) followed by SEMCI (8.73 mE, 49.3 mmol) and the reaction was stirred at room temperature for 18 hours. The reaction was washed with water, 1 N aqueous HC1 solution and saturated aqueous sodium hydrogen carbonate solution, brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 3% EtOAc in hexanes to afford the title compound. ?H NMR (400 MHz, CDC13): oe ppm 0.00 (s, 9H), 0.90 (m, 2H), 1.25 (m, 3H), 2.75 (m, 2H), 3.75 (m, 2H), 5.20 (s, 2H), 6.80 (m, 1H), 7.00 (d, 1H), 7.40 (d, 1H).

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 767 - 786
[2]Patent: US2015/329542,2015,A1 .Location in patent: Paragraph 0778

9
[ 99873-30-0 ]
6-(2-ethyl-4-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-c]pyridin-4-yl trifluoromethanesulfonate [ No CAS ]

Reference： [1]Patent: US2015/329542,2015,A1

10
[ 99873-30-0 ]
6-(2-ethyl-4-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-c]pyridin-4-ol [ No CAS ]

Reference： [1]Patent: US2015/329542,2015,A1

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Isomers

Technical Information

? Acidity of Phenols ? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Chan-Lam Coupling Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Halogenation of Phenols ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Oxidation of Phenols ? Pechmann Coumarin Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reimer-Tiemann Reaction ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

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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. 99873-30-0 ] {[proInfo.proName]}

Quality Control of [ 99873-30-0 ]

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Medicinal Chemistry

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[ 99873-30-0 ] Synthesis Path-Upstream 1~1

[ 99873-30-0 ] Synthesis Path-Downstream 1~10

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Aryls

Bromides

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[ 99873-30-0 ]