[ CAS No. 3964-56-5 ] {[proInfo.proName]}

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Quality Control of [ 3964-56-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3964-56-5 ]

SDS Specification

Alternatived Products of [ 3964-56-5 ]

Product Details of [ 3964-56-5 ]

CAS No. :	3964-56-5	MDL No. :	MFCD00002166
Formula :	C₆H₄BrClO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VIBJPUXLAKVICD-UHFFFAOYSA-N
M.W :	207.45	Pubchem ID :	19859
Synonyms :

Calculated chemistry of [ 3964-56-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.18
TPSA :	20.23 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.35 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.07
Log Po/w (XLOGP3) :	3.12
Log Po/w (WLOGP) :	2.81
Log Po/w (MLOGP) :	2.84
Log Po/w (SILICOS-IT) :	2.7
Consensus Log Po/w :	2.71

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.59
Solubility :	0.0539 mg/ml ; 0.00026 mol/l
Class :	Soluble
Log S (Ali) :	-3.21
Solubility :	0.127 mg/ml ; 0.000611 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.3
Solubility :	0.105 mg/ml ; 0.000506 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.48

Safety of [ 3964-56-5 ]

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 [ 3964-56-5 ]

* 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 [ 3964-56-5 ]
Downstream synthetic route of [ 3964-56-5 ]

[ 3964-56-5 ] Synthesis Path-Upstream 1~3

1
[ 95-57-8 ]
[ 3964-56-5 ]
[ 2040-88-2 ]
[ 4526-56-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-Bromosuccinimide; thiourea In acetonitrile at 20℃; for 2 h;	General procedure: Reaction conditions: Thiourea (5.1 molpercent, 2 mg, 0.026 mmol) was added to an acetonitrile solution (10 mL) containing NBS (1.15 equiv, 104.4 mg, 0.587 mmol). Anisole (56.3 mg, 0.51 mmol) was added immediately to the resulting stirred solution and allowed to stir at room temperature for 10 min. The reaction was quenched by the addition of 10percent aqueous solution of Na₂S₂O₃ (10 mL) and extracted with ethyl acetate (70 mL). The organic solution was then washed with additional 10percent Na₂S₂O₃ (2 * 10 mL), followed by deionized water (3 * 15 mL) and brine (2 * 10 mL). The organic solution was then dried over anhydrous Na₂SO₄ and the solvent was evaporated in vacuo. The major product of each reaction was isolated by centrifugal thin-layer chromatography using a 2 mm thick silica gel 60GF₂₅₄ coated plate (5percent CH₂Cl₂/hexanes). The products reported herein are known compounds and were characterised by GC-MS, IR, ¹H and ¹³C NMR. Their spectroscopic data are in agreement with those reported in the literature.

Reference： [1] Tetrahedron, 2017, vol. 73, # 46, p. 6564 - 6572
[2] Dalton Transactions, 2013, vol. 42, # 33, p. 11926 - 11940
[3] Journal of Organic Chemistry, 1997, vol. 62, p. 4504 - 4506
[4] Journal of Organic Chemistry, 1997, vol. 62, p. 4504 - 4506
[5] Tetrahedron, 2007, vol. 63, # 23, p. 4959 - 4967
[6] Tetrahedron, 2007, vol. 63, # 23, p. 4959 - 4967
[7] Tetrahedron, 2010, vol. 66, # 34, p. 6928 - 6935

2
[ 95-57-8 ]
[ 3964-56-5 ]
[ 2040-88-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 15, p. 1877 - 1878
[2] Journal of Chemical Research - Part S, 2003, # 9, p. 597 - 598
[3] Tetrahedron, 2007, vol. 63, # 23, p. 4959 - 4967
[4] Monatshefte fur Chemie, 2012, vol. 143, # 7, p. 1039 - 1044

3
[ 108-95-2 ]
[ 3964-56-5 ]
[ 2040-88-2 ]

Reference： [1] Monatshefte fur Chemie, 2012, vol. 143, # 7, p. 1039 - 1044

[ 3964-56-5 ] Synthesis Path-Downstream 1~10

1
[ 50638-47-6 ]
[ 3964-56-5 ]

Reference： [1]Monatshefte fur Chemie,1927,vol. 48,p. 209

2
[ 3964-56-5 ]
[ 77-78-1 ]
[ 50638-47-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6224 - 6229
[2]Journal of Medicinal Chemistry,1996,vol. 39,p. 1846 - 1856
[3]Journal of Heterocyclic Chemistry,1968,vol. 5,p. 165 - 177
[4]Journal of Organic Chemistry,1994,vol. 59,p. 6233 - 6244

3
[ 3964-56-5 ]
[ 67-68-5 ]
[ 50638-47-6 ]

Reference： [1]Chemosphere,2001,vol. 45,p. 1119 - 1127

4
[ 3964-56-5 ]
[ 182344-13-4 ]

Yield	Reaction Conditions	Operation in experiment
15%		3-chIoro-4-hydroxyphenylboronic acid 83. To a stirred solution of 4-bromo-2-chlorophenol (5 g5 24 mmol) in dry THF (75 mL)5 cooled to -780C5 was added slowly drop-wise n-BuLi (12 mL of a 2.44 M solution, 29 mmol) and the reaction was stirred at -78°C for 2 h. To this was then added trimethyl borate (3.3 mL, 29 mmol) and the reaction was allowed to warm slowly to r.t. with stirring for 19 h. The reaction was quenched with HCl (aq., 2 M) and the organics extracted into EtOAc (2 x 60 mL). These extracts were combined and concentrated under reduced pressure to give a white precipitate in an oily substance. To this was added hexane and the white powder was collected by filtration and washed with hexane. Yield 15percent: 1H NMR delta (270 MHz, DMSOd6) 6.49 (bs), 6.91 (IH5 d, J= 7.9 Hz)5 7.54 (IH, dd, J= 8.2, 1.5 Hz)5 7.72 (IH5 d, J= 1.5 Hz)5 8.02 (bs), 10.32 (IH, s); HPLC tr = 3.36 min (>91percent) 90percent MeCN in H2O; LC/MS (APCI) m/z 171.16 (M-H)-.
12 - 27%		3-ChIoro-4-hydroxyphenylboronic acid (TJA01187) C6H6BClO3 MW 172.37. A dry 250 ml r.b. flask was loaded with 4-bromo-2-chlorophenol (5.00 g, 24.1 mmol) and purged with N2(g). Anhydrous THF (100 mL) added with stirring and the vessel cooled to -78 0C (dry ice/acetone bath). After 30 mins n-BuLi, 2.3 M in hexanes, (12.9 mL, 28.9 mmol) was added dropwise over 20 min. The reaction was left to stir for 1 h. Triisopropyl borate (6.65 mL, 28.9 mmol) was added dropwise with the reaction still at -78 0C. After 15 min of stirring at this temperature the dry ice/acetone bath was removed. At about 0 0C 2 M HCl(aq) (5 mL) was added and the reaction left to stir for a further 15 min. THF removed under vacuum and residues taken up in ethyl acetate (50 mL). Distilled H2O (50 mL) was added and the organic layer separated. The aqueous layer was extracted with ethyl acetate (50 mL x 2). The organic portions were combined and washed with sat. Na2CO3 (aq). The aqueous layer was separated and treated with 2M HCl (aq) until the pH was about 4. This was then extracted with ethyl acetate (50 mL x 2). The organic portions were then dried over MgSO4 and solvent removed. The resultant off white residues were taken up in a minimum of ethyl acetate (2-3 mL) and added to dropwise to hexane (50 mL) with stirring. The white ppt was filtered to give the title compound as an off white solid (0.490 g, 12 percent).1H NMR (600 MHz, DMSO-^6) delta 6.89-6.92 (IH5 d, J= 8.2 Hz, ArH), 7.52-7.56 (IH5 dd, J= 1.8 7.9 Hz, ArH)5 7.72-7.73 (IH, d, J= 1.5 Hz5 ArH)5 7.98 (2H, s, ArB(OH)2) and 10.33 (IH5 s, ArOH); HPLC (70 percent CH3CN in H2O) ttau= 3.654 (97.92 percent); LCMS (APCI), m/z 173.11 (37ClM-- H5 15 percent)5 171.10 (35ClM"- H5 55), 129.05 ((37ClM" - H) - B(OH)2, 3O)5 127.04 ((35ClM- - H) - B(OH)2, 100).

Reference： [1]Patent: WO2007/96647,2007,A2 .Location in patent: Page/Page column 125-126
[2]Patent: WO2007/68905,2007,A1 .Location in patent: Page/Page column 120-121; 148-149; 152-153; 154-155
[3]Journal of the American Chemical Society,2007,vol. 129,p. 1894 - 1895

5
[ 3964-56-5 ]
[ 584-08-7 ]
[ 50638-47-6 ]

Yield	Reaction Conditions	Operation in experiment
10.2 g (96%)	In ethyl acetate; acetone;	Step 1 Preparation of 4-bromo-2-chloroanisole Under nitrogen, 7.3 mL (77 mmol) of dimethylsulfate was added to a stirred suspension of 10 g (48 mmol) of 4-bromo-2-chlorophenol and 5.4 g (38 mmol) of powered K2 CO3 in 75 mL of fresh acetone. After 2 hours at reflux, the reaction was cooled to ambient temperature, filtered, and concentrated in vacuo. The residue was dissolved in ethyl acetate; the resulting solution was washed with water and dried over MgSO4. Concentration in vacuo gave 10.2 g (96%) of 4-bromo-2-chloroanisole as a colorless solid: mp 68.5-70.5 C.; NHR (CDCl3) delta 3.88 (s, 3H), 6.80 (d, J=9 Hz, 1H), 7.33 (dd, J=2, 9 Hz, 1H), 7.50 (d, J=2 Hz, 1H).

Reference： [1]Patent: US5739166,1998,A

6
[ 3964-56-5 ]
[ 74-88-4 ]
[ 50638-47-6 ]

Yield	Reaction Conditions	Operation in experiment
100%		(RS)-4-(3-Bromo-4-fluoro-phenyl)-4-(3-chloro-4-methoxy-phenyl)-4,5-dihydro-oxazol-2-ylamine 4-Bromo-2-chloro-1-methoxy-benzene [50638-47-6] A mixture of 4-bromo-2-chlorophenol (7.0 g, 33.0 mmol, 1 eq), N,N-dimethylformamide (50 mL) and cesium carbonate (8.5 g, 42.0 mmol, 1.2 eq) was stirred at room temperature then iodomethane (2.5 mL, 1.2 eq) was added. The mixture was heated to 50 C. overnight, cooled to room temperature and treated with water (500 mL). The reaction was extracted with dichloromethane, dried (sodium sulfate) and concentrated in vacuo. The crude was purified by flash chromatography eluding with cyclohexane. 7.5 g of clean product in a quantitative yield. Mass (calculated) C7H6BrClO [221] MH+ not observed LC Rt=3.15 min (5 min method) 1H-NMR (CDCl3): 3.88 (s, 3H), 6.80 (d, 1H), 7.32 (m, 1H), 7.50 (m, 1H)
98%	In tetrahydrofuran;	A. A solution of 4-bromo-2-chlorophenol (5.18 g) in 20 ml tetrahydrofuran was added dropwise to a stirred mixture of sodium hydride (0.72 g) in tetrahydrofuran (50 ml). After 30 minutes, iodomethane (4.26 g) was added and the mixture was stirred overnight at room temperature. A further 7.1 g of iodomethane was added and the mixture was heated at reflux overnight. The reaction mixture was then partitioned between water and chloroform. The combined organic extracts were dried and evaporated to yield the product after washing with hexanes as a white solid (5.4 g, 98% yield) of m.p. 63 C. Anal.: Calcd. for C7H6BrC10: C, 38.00; H, 2.71%. Found: C, 38.07; H, 2.80%.
	With potassium carbonate; In acetone;	Ligand Precursor 2: Following Scheme 3, a mixture of 4-bromo-2-chlorophenol (4.66 g, 22.45 mmol), iodomethane (3.1 mL, 50 mmol), and powdered K2CO3 (13.8 g, 100 mmol) in acetone (20 mL) is stirred at 65 C. for 1 hour. After filtration and removal of the solvent, 4.3 g (19.4 mmol, 86%) of 4-bromo-2-chloroanisole are obtained as a white solid.

26.7 g

With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 2h;

1) Synthesis of 4-bromo-2-chloro-1-methoxybenzene (compound 211-1) [0352] 4-Bromo-2-chlorophenol (25.0 g) was dissolved in N,N-dimethylformamide (150 ml), potassium carbonate (33.2 g) and methyl iodide (25.6 g) were added, and the mixture was stirred at 60C for 2 hr. The reaction mixture was poured into water, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give compound 211-1 (26.7 g) as a pale-yellow solid. 1H-NMR(CDCl3)delta(ppm):3.88(3H,s), 6.79(1H,d,J=9.4Hz), 7.32(1H,dd,J=8.6,2.4Hz), 7.49(1H,d,J=2.4Hz).

Reference： [1]Patent: US2009/209529,2009,A1 .Location in patent: Page/Page column 24
[2]Patent: US4623650,1986,A
[3]Angewandte Chemie - International Edition,2014,vol. 53,p. 6443 - 6448
Angew. Chem.,2014,vol. 126,p. 6561 - 6566
[4]Angewandte Chemie - International Edition,2013,vol. 52,p. 9144 - 9148
Angew. Chem.,2013,vol. 52,p. 9144 - 9148,5
[5]Journal of the American Chemical Society,2019,vol. 141,p. 19257 - 19262
[6]Patent: US2003/232717,2003,A1
[7]Patent: EP2842937,2015,A1 .Location in patent: Paragraph 0352-0353

7
[ 924869-17-0 ]
[ 3964-56-5 ]
methyl 2-(3-chloro-4-hydroxyphenyl)benzo[d]oxazole-5-carboxylate [ No CAS ]

Reference： [1]Journal of Natural Products,2019,vol. 82,p. 1325 - 1330

8
[ 2895-21-8 ]
[ 3964-56-5 ]
C₁₁H₁₃BrClNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 80℃; for 4h;	General procedure: To a solution of 5- bromine -2- chlorophenol (2.9g, 14.3mmol) in 50mL acetonitrile was added K2CO3 (2.5g,17.1mmol), and stirred for 30min intermediate product 10 was added and the solution was heated to 80C for 4h. The reaction solution was concentrated, water (100mL) was added, and extracted with EtOAc. The organic layer was collected and washed with water and brine for three times, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography to afford intermediate product 11.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 178,p. 667 - 686

9
[ 3964-56-5 ]
[ 19047-31-5 ]
C₁₁H₁₁BrClNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 80℃; for 4h;	General procedure: To a solution of 5- bromine -2- chlorophenol (2.9g, 14.3mmol) in 50mL acetonitrile was added K2CO3 (2.5g,17.1mmol), and stirred for 30min intermediate product 10 was added and the solution was heated to 80C for 4h. The reaction solution was concentrated, water (100mL) was added, and extracted with EtOAc. The organic layer was collected and washed with water and brine for three times, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography to afford intermediate product 11.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 178,p. 667 - 686

10
[ 3964-56-5 ]
[ 102151-33-7 ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 19257 - 19262

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Isomers

Technical Information

? Acidity of Phenols ? Alkyl Halide Occurrence ? Chan-Lam Coupling Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? General Reactivity ? Grignard Reaction ? Halogenation of Phenols ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Oxidation of Phenols ? Pechmann Coumarin Synthesis ? Preparation of Aldehydes and Ketones ? 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

Historical Records

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[ 3964-56-5 ]

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P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
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. 3964-56-5 ] {[proInfo.proName]}

Quality Control of [ 3964-56-5 ]

Related Doc. of [ 3964-56-5 ]

Product Details of [ 3964-56-5 ]

Calculated chemistry of [ 3964-56-5 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 3964-56-5 ]

Application In Synthesis of [ 3964-56-5 ]

[ 3964-56-5 ] Synthesis Path-Upstream 1~3

[ 3964-56-5 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 3964-56-5 ]

Aryls

Bromides

Chlorides

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[ 3964-56-5 ]