[ CAS No. 20532-33-6 ] {[proInfo.proName]}

Name: 20532-33-6|5-Chlorobenzothiophene|97%
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SKU: A155777
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Quality Control of [ 20532-33-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 20532-33-6 ]

SDS Specification

Alternatived Products of [ 20532-33-6 ]

Product Details of [ 20532-33-6 ]

CAS No. :	20532-33-6	MDL No. :	MFCD00055623
Formula :	C₈H₅ClS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SNYURIHMNFPQFL-UHFFFAOYSA-N
M.W :	168.64	Pubchem ID :	11309754
Synonyms :

Calculated chemistry of [ 20532-33-6 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.84
TPSA :	28.24 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) :	-4.69 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.31
Log Po/w (XLOGP3) :	3.72
Log Po/w (WLOGP) :	3.55
Log Po/w (MLOGP) :	3.23
Log Po/w (SILICOS-IT) :	4.33
Consensus Log Po/w :	3.43

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.9
Solubility :	0.0215 mg/ml ; 0.000127 mol/l
Class :	Soluble
Log S (Ali) :	-4.0
Solubility :	0.0167 mg/ml ; 0.000099 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.95
Solubility :	0.0189 mg/ml ; 0.000112 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.78

Safety of [ 20532-33-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 20532-33-6 ]

* 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 [ 20532-33-6 ]
Downstream synthetic route of [ 20532-33-6 ]

[ 20532-33-6 ] Synthesis Path-Upstream 1~9

1
[ 20532-33-6 ]
[ 20532-28-9 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737
[2] Angewandte Chemie - International Edition, 2015, vol. 54, # 12, p. 3773 - 3777[3] Angew. Chem., 2015, vol. 127, # 12, p. 3844 - 3848,5
[4] Organic Letters, 2014, vol. 16, # 17, p. 4388 - 4391
[5] Organometallics, 2016, vol. 35, # 18, p. 3248 - 3254

2
[ 20532-33-6 ]
[ 19301-35-0 ]

Reference： [1] Journal of Organic Chemistry, 2014, vol. 79, # 11, p. 5351 - 5358

3
[ 50548-46-4 ]
[ 20532-33-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With PPA In chlorobenzene for 0.0833333 h; Heating / reflux	A 25 mL round bottom flask was charged with (4-chlorophenyl)(2,2-diethoxyethyl)sulfane (500 mg, 1.92 mmol) and chlorobenzene (2 mL). The resulting mixture was added dropwise into boiling polyphosphoric acid (1 g) in chlorobenzene (5 mL) over 5 min. Work-up: the mixture was poured over ice water (25 mL), extracted three times with EtOAc (25 mL), washed with brine (50 mL), and dried over Na₂SO₄. The mixture was concentrated, and purified by SiO₂flash chromatography eluting with PE to afford the title compound in 290 mg (90percent yield), as an off white solid
90%	With polyacrylic acid In chlorobenzene	(4-chlorophenyl) (2,2-diethoxyethyl) sulfane (5 g, 19 mmol) and chlorobenzene (4 ml) were poured into a 250 ml two-necked round bottom flask, The reaction mixture was then added to a polyacrylic acid (PAA) reaction solution (5 g) obtained after boiling in chlorobenzene (5 ml). After the reaction, ice water (25 ml) was added to the mixture, and the mixture was washed with brine (50 ml) and dried over Na2S04. The mixture was chromatographed using petroleum ether to give 2.9 g of a white solid (90percent yield).

Reference： [1] Patent: US2008/21026, 2008, A1, . Location in patent: Page/Page column 17; 27
[2] Patent: CN103896967, 2016, B, . Location in patent: Paragraph 0048; 0052-0054
[3] Journal of Organic Chemistry, 1995, vol. 60, # 7, p. 1936 - 1938
[4] Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 96, # 1-4, p. 441 - 444
[5] Bioorganic and medicinal chemistry, 2004, vol. 12, # 9, p. 2251 - 2273
[6] Patent: US2005/176769, 2005, A1, . Location in patent: Page/Page column 54

4
[ 118743-10-5 ]
[ 20532-33-6 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1271 - 1272
[2] MedChemComm, 2016, vol. 7, # 6, p. 1093 - 1101
[3] Proceedings - Indian Academy of Sciences, Section A, 1950, # 32, p. 396,401
[4] Patent: WO2013/119895, 2013, A1, . Location in patent: Paragraph 00291

5
[ 13771-75-0 ]
[ 20532-33-6 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 5, p. 1025 - 1030

6
[ 106-54-7 ]
[ 20532-33-6 ]

Reference： [1] Patent: WO2013/119895, 2013, A1,
[2] MedChemComm, 2016, vol. 7, # 6, p. 1093 - 1101
[3] Patent: CN103896967, 2016, B,

7
[ 110-81-6 ]
[ 106-46-7 ]
[ 188290-36-0 ]
[ 20532-33-6 ]
[ 5181-10-2 ]
[ 108-90-7 ]
[ 106-54-7 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 1516 - 1522[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 8, p. 1736 - 1743

8
[ 20532-33-6 ]
[ 68-12-2 ]
[ 28540-51-4 ]

Reference： [1] Bioorganic and medicinal chemistry, 2004, vol. 12, # 9, p. 2251 - 2273
[2] Patent: WO2015/65937, 2015, A1, . Location in patent: Paragraph 000541

9
[ 20532-33-6 ]
[ 28540-51-4 ]

Reference： [1] Patent: US6420375, 2002, B1,

[ 20532-33-6 ] Synthesis Path-Downstream 1~88

1
[ 118743-10-5 ]
[ 20532-33-6 ]

Yield	Reaction Conditions	Operation in experiment
		(4-chlorophenyl)(2,2-dimethoxyethyl)sulfane (95 mmol) was dissolved in chlorobenzene (50 mL). The resulting mixture was added dropwise to boiling polyphosphoric acid (200 g) in chlorobenzene (100 mL) over 10 minutes. The mixture was then poured into ice water (500 mL) and Na2C03 was added until the pH 8. The mixture was then extracted with EtOAc (3 x 100 mL), and the combined organic layers were washed with brine (3 x 50 mL) and dried over anhydrous Na2S04. After filtration and concentration, the crude product was purified by column chromatography to give the title compound.

Reference： [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1271 - 1272
[2]MedChemComm,2016,vol. 7,p. 1093 - 1101
[3]Proceedings - Indian Academy of Sciences, Section A,1950,p. 396,401
[4]Patent: WO2013/119895,2013,A1 .Location in patent: Paragraph 00291

2
[ 110-81-6 ]
[ 106-46-7 ]
[ 188290-36-0 ]
[ 20532-33-6 ]
[ 5181-10-2 ]
[ 108-90-7 ]
[ 106-54-7 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 1516 - 1522
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 1736 - 1743

3
[ 20532-33-6 ]
[ 79-35-6 ]
5-chloro-2-(2,2-dichloro-1-fluoroethenyl)benzothiophene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 3311 - 3317

4
[ 50548-46-4 ]
[ 20532-33-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With PPA; In chlorobenzene; for 0.0833333h;Heating / reflux;	A 25 mL round bottom flask was charged with (4-chlorophenyl)(2,2-diethoxyethyl)sulfane (500 mg, 1.92 mmol) and chlorobenzene (2 mL). The resulting mixture was added dropwise into boiling polyphosphoric acid (1 g) in chlorobenzene (5 mL) over 5 min. Work-up: the mixture was poured over ice water (25 mL), extracted three times with EtOAc (25 mL), washed with brine (50 mL), and dried over Na2SO4. The mixture was concentrated, and purified by SiO2 flash chromatography eluting with PE to afford the title compound in 290 mg (90% yield), as an off white solid
90%	With polyacrylic acid; In chlorobenzene;	(4-chlorophenyl) (2,2-diethoxyethyl) sulfane (5 g, 19 mmol) and chlorobenzene (4 ml) were poured into a 250 ml two-necked round bottom flask, The reaction mixture was then added to a polyacrylic acid (PAA) reaction solution (5 g) obtained after boiling in chlorobenzene (5 ml). After the reaction, ice water (25 ml) was added to the mixture, and the mixture was washed with brine (50 ml) and dried over Na2S04. The mixture was chromatographed using petroleum ether to give 2.9 g of a white solid (90% yield).
	With PPA; Polyphosphoric acid (PPA);	Compound 14d was prepared from Compound 14a by the methods described in J. Med. Chem. 1989, 32(12), 2548-2554 and J. Het. Chem. 1998, 25, 1271: HPLC: 3.95 min.

Reference： [1]Patent: US2008/21026,2008,A1 .Location in patent: Page/Page column 17; 27
[2]Patent: CN103896967,2016,B .Location in patent: Paragraph 0048; 0052-0054
[3]Journal of Organic Chemistry,1995,vol. 60,p. 1936 - 1938
[4]Phosphorus, Sulfur and Silicon and the Related Elements,1994,vol. 96,p. 441 - 444
[5]Bioorganic and medicinal chemistry,2004,vol. 12,p. 2251 - 2273
[6]Patent: US2005/176769,2005,A1 .Location in patent: Page/Page column 54
[7]Chemical Communications,2019,vol. 55,p. 11187 - 11190

5
[ 20532-33-6 ]
[ 128851-98-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954

6
[ 20532-33-6 ]
[ 216959-78-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954

7
[ 20532-33-6 ]
1-[(5-chlorobenzo[b]thien-2-yl)sulfonyl]-4-[4-(4-pyridyl)benzoyl]piperazine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3927 - 3954

8
[ 20532-33-6 ]
[ 212078-51-8 ]