[ CAS No. 63285-84-7 ]

Name: 63285-84-7|3-Phenoxythiophene|98%
Brand: Ambeed
SKU: A561084
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Quality Control of [ 63285-84-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 63285-84-7 ]

Product Details of [ 63285-84-7 ]

CAS No. :	63285-84-7	MDL No. :	MFCD00178747
Formula :	C₁₀H₈OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DXSHUWUDKNEGFS-UHFFFAOYSA-N
M.W :	176.23	Pubchem ID :	7018947
Synonyms :

Calculated chemistry of [ 63285-84-7 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.84
TPSA :	37.47 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.15 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.51
Log Po/w (XLOGP3) :	3.13
Log Po/w (WLOGP) :	3.54
Log Po/w (MLOGP) :	2.42
Log Po/w (SILICOS-IT) :	3.76
Consensus Log Po/w :	3.07

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.45
Solubility :	0.0624 mg/ml ; 0.000354 mol/l
Class :	Soluble
Log S (Ali) :	-3.59
Solubility :	0.0457 mg/ml ; 0.000259 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.92
Solubility :	0.0211 mg/ml ; 0.00012 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.57

Safety of [ 63285-84-7 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P280-P301+P310-P305+P351+P338-P405-P501	UN#:	2810
Hazard Statements:	H301-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 63285-84-7 ]

* 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.

Downstream synthetic route of [ 63285-84-7 ]

[ 63285-84-7 ] Synthesis Path-Downstream 1~13

1
[ 872-31-1 ]
[ 108-95-2 ]
[ 63285-84-7 ]

Yield	Reaction Conditions	Operation in experiment
74%	copper(I) chloride; In pyridine; mineral oil;	A. 3-Phenoxythiophene Cuprous chloride (3.08 g, 31.1 mmol) and phenol (8.78 g, 93.3 mmol) were sequentially added to a solution of 3-bromothiophene (5.06 g, 31.1 mmol) in pyridine (150 ml). Sodium hydride (3.73 g, 93.3 mmol, 60% dispersion in mineral oil) was then slowly added. The reaction was heated at reflux for 20 hours under Argon. The pyridine was removed under reduced pressure. The residue was diluted with Et2O (200 ml) and washed with 1 N NaOH (3100 ml), 1 N HCl (2150 ml) and 1 N NaOH (150 ml). The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was chromatographed using hexanes to give 3-phenoxy-thiophene as a clear oil (4.0 g, 74% yield).
74%	copper(I) chloride; In pyridine; mineral oil;	A. 3-Phenoxythiophene Cuprous chloride (3.08 g, 31.1 mmol) and phenol (8.78 g, 93.3 mmol) were sequentially added to a solution of 3-bromothiophene (5.06 g, 31.1 mmol) in pyridine (150 ml). Sodium hydride (3.73 g, 93.3 mmol, 60% dispersion in mineral oil) was then slowly added. The reaction was heated at reflux for 20 hours under Argon. The pyridine was removed under reduced pressure. The residue was diluted with Et2 O (200 ml) and washed with 1N NaOH (3100 ml), 1N HCl (2150 ml) and 1N NaOH (150 ml). The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was chromatographed using hexanes to give 3-phenoxy-thiophene as a clear oil (4.0 g, 74% yield).
74%	In pyridine; mineral oil;	A. 3-Phenoxythiophene. Couprous chloride (3.08 g, 31.1 mmol) and phenol (8.78 g, 93.3 mmol) were sequentially added to a solution of 3-bromothiophene (5.06 g, 31.1 mmol) in pyridine (150 ml). Sodium hydride (3.73 g, 93.3 mmol, 60% dispersion in mineral oil) was then slowly added. The reaction was heated at reflux for 20 hours under Argon. The pyridine was removed under reduced pressure. The residue was diluted with EtO (200 ml) and washed with 1N NaOH (3100 ml), 1N HCl (2150 ml) and 1N NaOH (150 ml). The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was chromatographed using hexanes to give 3-phenoxy-thiophene as a clear oil (4.0 g, 74% yield).

31 g (29%)

With copper; potassium carbonate; In chloroform;

a) 3-phenoxythiophene. A mixture of 3-bromothiophene (100 g, 610 mMol), phenol (61.2 g, 650 mMol), copper bronze (5 g) and potassium carbonate (30 g, 220 mMol) was heated to 150 C. After heating for 7 days the mixture was cooled, diluted with 300 mL of chloroform and filtered. The solids were thoroughly washed with chloroform and the filtrates combined. The combined organics were washed with 10% NaOH (2*300 mL), water (300 mL), dried (MgSO4) and concentrated. The residue was factionally distilled to afford 31 g (29%) (80 C., 3 mm) of the desired ether as a clear liquid.

Reference： [1]Patent: US2002/95041,2002,A1
[2]Patent: US5962490,1999,A
[3]Patent: US6342610,2002,B2 .Location in patent: Page column 70
[4]Patent: US5571821,1996,A
[5]Journal of Organic Chemistry,1982,vol. 47,p. 1755 - 1759
[6]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656
[7]Patent: US5185363,1993,A

2
[ 63285-84-7 ]
[ 124-38-9 ]
[ 81028-68-4 ]
[ 81028-69-5 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 1755 - 1759

3
[ 63285-84-7 ]
[ 124-38-9 ]
[ 81028-68-4 ]
[ 81028-70-8 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 1755 - 1759

4
[ 63285-84-7 ]
[ 166964-13-2 ]

Yield	Reaction Conditions	Operation in experiment
17%	With N-chloro-succinimide; n-butyllithium; sulfur dioxide; In tetrahydrofuran;	B. 3-Phenoxythiophene-2-sulfonyl chloride BuLi (2.38 M, 11.5 ml, 27.28 mmol) was slowly added to a solution of <strong>[63285-84-7]3-phenoxythiophene</strong> (4.0 g, 22.73 mmol) in ether (50 ml) at 0 C. The reaction was stirred at 0 C. for 1 h. SO2 was bubbled through the mixture for 15 minutes at 0 C. followed by the addition of NCS (3.95 g, 29.55 mmol) as a suspension in THF (20 ml). The mixture was allowed to warm up to 25 C. and stirred for 2 more h. The precipitate was filtered, and the filtrate was concentrated and chromatographed (hexanes) to give <strong>[63285-84-7]3-phenoxythiophene</strong>-2- sulfonyl chloride as a yellowish solid (1.03 g, 17% yield).
17%	With N-chloro-succinimide; n-butyllithium; sulfur dioxide; In tetrahydrofuran;	B. 3-Phenoxythiophene-2-sulfonyl chloride BuLi (2.38 M, 11.5 ml, 27.28 mmol) was slowly added to a solution of <strong>[63285-84-7]3-phenoxythiophene</strong> (4.0 g, 22.73 mmol) in ether (50 ml) at 0 C. The reaction was stirred at 0 C. for 1 h. SO2 was bubbled through the mixture for 15 minutes at 0 C. followed by the addition of NCS (3.95 g, 29.55 mmol) as a suspension in THF (20 ml). The mixture was allowed to warm up to 25 C. and stirred for 2 more h. The precipitate was filtered, and the filtrate was concentrated and chromatographed (hexanes) to give <strong>[63285-84-7]3-phenoxythiophene</strong>-2-sulfonyl chloride as a yellowish solid (1.03 g, 17% yield).
17%	With N-chloro-succinimide; n-butyllithium; sulfur dioxide; In tetrahydrofuran;	B. 3-Phenoxythiophene-2-sulfonyl chloride BuLi (2.38M, 11.5 ml, 27.28 mmol) was slowly added to a solution of <strong>[63285-84-7]3-phenoxythiophene</strong> (4.0 g, 22.73 mmol) in ether (50 ml) at 0 C. The reaction was stirred at 0 C. for 1 h. SO2 was bubbled through the mixture for 15 minutes at 0 C. followed by the addition of NCS (3.95 g, 29.55 mmol) as a suspension in THF (20 ml). The mixture was allowed to warm up to 25 C. and stirred for 2 more h. The precipitate was filtered, and the filtrate was concentrated and chromatographed (hexanes) to give <strong>[63285-84-7]3-phenoxythiophene</strong>-2-sulfonyl chloride as a yellowish solid (1.03 g, 17% yield).

17%

With N-chloro-succinimide; sulfur dioxide; In tetrahydrofuran;

B. 3-Phenoxythiophene-2-sulfonyl chloride BuLl (2.38M, 11.5 ml, 27.28 mmol) was slowly added to a solution of <strong>[63285-84-7]3-phenoxythiophene</strong> (4.0 g, 22.73 mmol) in ether (50 ml) at 0 C. The reaction was stirred at 0 C. for 1 h. SO2 was bubbled through the mixture for 15 minutes at 0 C. followed by the addition of NCS (3.95 g, 29.55 mmol) as a suspension in THF (20 ml). The mixture was allowed to warm up to 250 C. and stirred at for 2 more hours. The precipitate was filtered, and the filtrate was concentrated and chromatographed (hexanes) to give <strong>[63285-84-7]3-phenoxythiophene</strong>-2-sulfonyl chloride as a yellowish solid (1.03 g, 17% yield).

Reference： [1]Patent: US2002/95041,2002,A1
[2]Patent: US5962490,1999,A
[3]Patent: US5594021,1997,A
[4]Patent: US6342610,2002,B2 .Location in patent: Page column 71
[5]Patent: US5571821,1996,A
[6]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656

6
[ 63285-84-7 ]
N-(4-bromo-3-methyl-5-isoxazolyl)-3-phenoxythiophene-2-sulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2651 - 2656
[2]Patent: US5571821,1996,A

7
[ 63285-84-7 ]
[ 54449-13-7 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 1755 - 1759
[2]Journal of Organic Chemistry,1982,vol. 47,p. 1755 - 1759

8
[ 63285-84-7 ]
[ 81028-71-9 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 1755 - 1759

9
[ 63285-84-7 ]
[ 132706-25-3 ]

Yield	Reaction Conditions	Operation in experiment
1.74 g (75%)	With n-butyllithium; In water; N,N-dimethyl-formamide;	b) <strong>[63285-84-7]3-phenoxythiophene</strong>-2-carboxaldehyde. To a 0 C. solution of <strong>[63285-84-7]3-phenoxythiophene</strong> (2 g, 11.4 mMol) in ether (50 mL) was added n-butyllithium (5 mL, 12.5 mMol, 2.5M in hexanes). The reaction was stirred for 15 min and N,N-dimethylformamide (3 mL) was added. The reaction was allowed to warm to room temperature. Water (5 mL) was added cautiously while stirring. The reaction mixture was diluted with ether and washed with water (100 mL). The aqueous layer was washed with ether and the organic layer combined, washed with brine, dried (MgSO4), and concentrated. The residue was purified by flash column chromotography (SiO2, eluted with 10% ethylacetate/hexanes) to afford 1.74 g (75%) of the desired aldehyde as a clear oil. The title compound was prepared according to the method of Example 127 using <strong>[63285-84-7]3-phenoxythiophene</strong>-2-carboxaldehyde (prepared above) instead of 3-bromothiophene-2-carboxaldehyde. mp: 132-133.5 C.; NMR (300 MHz, DMSO-d6) δ 4.55 (2H, s), 6.43 (2H, bs), 6.72 (1H, d, J=6 Hz), 6.95 (2H, m), 7.06 (1H, m), 7.33 (2H, m), 7.46 (1H, d, J=6 Hz), 9.44 (1H, s); MS m/e (DCI/NH3) 282 (M+NH4)+, 265 (M+H)+.

Reference： [1]Patent: US5185363,1993,A

10
[ 63285-84-7 ]
[ 132706-26-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With n-butyllithium; chloro-trimethyl-silane; In water; N,N-dimethyl-formamide;	a 4-phenoxy-5-trimethylsilylthiophene-2-carboxaldehyde To a 0 C. solution of <strong>[63285-84-7]3-phenoxythiophene</strong> (9.5 g, 53.9 mMol) in ether (200 mL) was added n-butyllithium (24 mL, 60 mMol, 2.5M in hexanes). The reaction was stirred for 15 min and trimethylsilyl chloride (6.45 g, 59.4 mMol) was added via syringe. The reaction was stirred 15 min and additional n-butyllithium (24 mL, 60 mMol, 2.5M in hexanes) was added and the reaction stirred 15 min. To the cold reaction mixture is added DMF (14 mL) and the reaction allowed to warm to room temperature over night. Water (5 mL) was added cautiously while stirring. The reaction mixture was diluted with ether and washed with water. The aqueous layer was washed with ether and the organic layer combined, washed with brine, dried (MgSO4), and concentrated. Purification by flash chromatography (SiO2, eluted with 5% ether/hexanes) afforded 4-phenoxy-5-trimethylsilylthiophene-2-carboxaldehyde (12.1 g, 83%) as a slightly yellow oil. The title compound was prepared as described in Example 137 except using 4-phenoxy-5-trimethylsilylthiophene-2-carboxaldehyde described above instead of 5-phenylthio-2-trimethylsilylthiophene-3-carboxaldehyde. mp: 120-122 C.; NMR (300 MHz, DMSO d6) δ 4.57 (2H, s), 6.46 (2H, bs), 6.78 (2H, s), 7.03 (2H, m), 7.12 (1H, m), 7.38 (2H, m), 9.49 (1H, s); MS m/e (DCI/NH3) 282 (M+NH4)+, 265 (M+H)+.

Reference： [1]Patent: US5185363,1993,A

11
[ 63285-84-7 ]
[ 591-50-4 ]
[ 1260170-07-7 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 8946 - 8949

12
[ 63285-84-7 ]
[ 41872-51-9 ]

Yield	Reaction Conditions	Operation in experiment
53%	With palladium(II) trifluoroacetate; silver(I) acetate; In propionic acid; at 110℃; for 20.0h;Schlenk technique; Inert atmosphere;Catalytic behavior;	General procedure: To a 10 mL Schlenk flask were placed 3-phenoxybenzo[b]thiophene (45.3 mg, 0.2 mmol), Pd(TFA)2 (6.6 mg, 0.02 mmol), AgOAc (66.8 mg, 0.4 mmol), and propionic acid (1.0 mL), the atmosphere was replaced by nitrogen, and the cock was closed. The mixture was magnetically stirred at 110 oC for 20 h. After cooling, the mixture was filtered through a celite pad and poured into aqueous NaHCO3, extracted with ethyl acetate, and dried over Na2SO4. Evaporation of the solvent and purification with column chromatography on silica gel using hexane/ethyl acetate (80:1, v/v) gave BTBF 2b (36.3 mg, 81%).

Reference： [1]Chemistry Letters,2015,vol. 44,p. 1125 - 1127

13
[ 63285-84-7 ]
C₁₀H₅⁽²⁾HOS [ No CAS ]
C₁₀H₇⁽²⁾HOS [ No CAS ]

Reference： [1]Chemistry Letters,2015,vol. 44,p. 1125 - 1127

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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. 63285-84-7 ]

Quality Control of [ 63285-84-7 ]

Related Doc. of [ 63285-84-7 ]

Product Details of [ 63285-84-7 ]

Calculated chemistry of [ 63285-84-7 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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[ 63285-84-7 ] Synthesis Path-Downstream 1~13

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