[ CAS No. 89640-03-9 ] {[proInfo.proName]}

Name: 89640-03-9|Ethyl 5-chloro-4-nitrothiophene-2-carboxylate|95%
Brand: Ambeed
SKU: A104345
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Quality Control of [ 89640-03-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 89640-03-9 ]

SDS Specification

Alternatived Products of [ 89640-03-9 ]

Product Details of [ 89640-03-9 ]

CAS No. :	89640-03-9	MDL No. :	MFCD12974868
Formula :	C₇H₆ClNO₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VJKXMTCBMRGJIE-UHFFFAOYSA-N
M.W :	235.64	Pubchem ID :	56763846
Synonyms :

Calculated chemistry of [ 89640-03-9 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.29
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.24
TPSA :	100.36 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.64 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.8
Log Po/w (XLOGP3) :	2.95
Log Po/w (WLOGP) :	2.49
Log Po/w (MLOGP) :	0.76
Log Po/w (SILICOS-IT) :	1.27
Consensus Log Po/w :	1.85

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.16
Solubility :	0.163 mg/ml ; 0.000692 mol/l
Class :	Soluble
Log S (Ali) :	-4.72
Solubility :	0.00449 mg/ml ; 0.0000191 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.15
Solubility :	1.66 mg/ml ; 0.00705 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.92

Safety of [ 89640-03-9 ]

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 [ 89640-03-9 ]

* 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 [ 89640-03-9 ]
Downstream synthetic route of [ 89640-03-9 ]

[ 89640-03-9 ] Synthesis Path-Upstream 1~1

1
[ 5751-82-6 ]
[ 89640-03-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	at 0 - 20℃;	Ethyl 5-chlorothiophene-2- carboxylate (2.7 g, 14.1 mmol) was added in portions to concentrated sulfuric acid (5 mL) and the stirred solution was cooled to below 0 ⁰C with a methanol/ice bath. Fuming nitric acid (1.78 g, 1.2 mL, 28.3 mmol) was added slowly, keeping the temperature below 0 ⁰C throughout the addition. On completion of addition the stirred mixture was removed from the cold bath and warmed to ambient temperature for 2 hours. The reaction was quenched by addition to ice/water (100 mL) resulting in formation of a sticky solid. The product was extracted into dichloromethane (2 x 100 mL). The combined organic extracts were dried (MgSO₄), filtered and the solvent was removed to afford an orange oil. The crude material was purified by silica gel chromatography using a 95:5 mixture of hexane and ethyl acetate as eluent to afford the title product as a solid (2.23 g, 67percent yield). ¹H NMR (CDCl₃) δ: 8.14 (IH, s), 4.37 (2H, q, J=7.11 Hz), 1.37 (3H, t, J=7.11 Hz).
62%	With nitric acid In water at 5 - 10℃; for 0.5 h;	To fuming nitric acid (50 mL) cooled in an ice bath to 5° was added neat ethyl 5- chloro-2-thiophene-2-carboxylate (10 g, 0.0524 mol) dropwise at such a rate that the reaction temperature remained below 10°. The reaction was stirred for 30 minutes at 5-10°, then added ice (200 g) and extracted with ethyl acetate (2x100 mL). The combined organic extracts were washed with water (2x100 mL) and brine (50 mL), then dried over magnesium sulfate and filtered. The filtrate was concentrated by rotary evaporation and the residue purified by silica gel flash chromatography eluting with 10:90 ethyl acetate/hexanes to afford the title compound as a crystalline light yellow solid (7.6 g, 0.0322 mol, 62percent). ¹H NMR (300 MHz, DMSO-D6) δ ppml.31 (t, J=7.17 Hz, 3 H) 4.35 (q, J=7.23 Hz, 2 H) 8.17 (s, 1 H).

Reference： [1] Patent: WO2010/114881, 2010, A1, . Location in patent: Page/Page column 43-44
[2] Patent: WO2008/133753, 2008, A2, . Location in patent: Page/Page column 126

[ 89640-03-9 ] Synthesis Path-Downstream 1~17

2
[ 89640-03-9 ]
[ 1193-02-8 ]
[ 943780-17-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium acetate; In ethanol; for 0.5h;Heating / reflux;	The product of Example 9OA (1.0 g, 4.244 mmol), 4-aminothiophenol (0.797 g, 6.366 mmol), and anhydrous sodium acetate (1.74 g, 21.22 mmol) were heated in anhydrous ethanol (40 mL) under a nitrogen atmosphere at reflux for 30 minutes. The reaction was cooled to room temperature, partitioned with ethyl acetate (100 mL) and water (50 mL), separated layers, and washed <n="128"/>organic phase with water (2x50 mL) and brine (50 mL). The organic extract was dried over sodium sulfate, filtered, and concentrated by rotary evaporation. Trituration of the resulting solid with ethyl ether (2x30 mL) afforded the title compound as a bright yellow solid (1.167 g, 3.598 mmol, 85%). 1H NMR (300 MHz, DMSO-D6) delta ppml.24 (t, J=7.17 Hz, 3 H) 4.24 (q, J=7.23 Hz, 2 H) 5.94 (s, 2 H) 6.71 (d, J=8.82 Hz, 2 H) 7.35 (d, J=8.46 Hz, 2 H) 8.08 (s, 1 H); MS (ESI+) m/z 325 (M+H)+, MS (ESI-) m/z 323 (M-H)".

Reference： [1]Patent: WO2008/133753,2008,A2 .Location in patent: Page/Page column 126-127

3
[ 5751-82-6 ]
[ 89640-03-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sulfuric acid; nitric acid; at 0 - 20℃;	Ethyl 5-chlorothiophene-2- carboxylate (2.7 g, 14.1 mmol) was added in portions to concentrated sulfuric acid (5 mL) and the stirred solution was cooled to below 0 0C with a methanol/ice bath. Fuming nitric acid (1.78 g, 1.2 mL, 28.3 mmol) was added slowly, keeping the temperature below 0 0C throughout the addition. On completion of addition the stirred mixture was removed from the cold bath and warmed to ambient temperature for 2 hours. The reaction was quenched by addition to ice/water (100 mL) resulting in formation of a sticky solid. The product was extracted into dichloromethane (2 x 100 mL). The combined organic extracts were dried (MgSO4), filtered and the solvent was removed to afford an orange oil. The crude material was purified by silica gel chromatography using a 95:5 mixture of hexane and ethyl acetate as eluent to afford the title product as a solid (2.23 g, 67% yield). 1H NMR (CDCl3) delta: 8.14 (IH, s), 4.37 (2H, q, J=7.11 Hz), 1.37 (3H, t, J=7.11 Hz).
62%	With nitric acid; In water; at 5 - 10℃; for 0.5h;	To fuming nitric acid (50 mL) cooled in an ice bath to 5 was added neat ethyl 5- chloro-2-thiophene-2-carboxylate (10 g, 0.0524 mol) dropwise at such a rate that the reaction temperature remained below 10. The reaction was stirred for 30 minutes at 5-10, then added ice (200 g) and extracted with ethyl acetate (2x100 mL). The combined organic extracts were washed with water (2x100 mL) and brine (50 mL), then dried over magnesium sulfate and filtered. The filtrate was concentrated by rotary evaporation and the residue purified by silica gel flash chromatography eluting with 10:90 ethyl acetate/hexanes to afford the title compound as a crystalline light yellow solid (7.6 g, 0.0322 mol, 62%). 1H NMR (300 MHz, DMSO-D6) delta ppml.31 (t, J=7.17 Hz, 3 H) 4.35 (q, J=7.23 Hz, 2 H) 8.17 (s, 1 H).

Reference： [1]Patent: WO2010/114881,2010,A1 .Location in patent: Page/Page column 43-44
[2]Patent: WO2008/133753,2008,A2 .Location in patent: Page/Page column 126
[3]Archiv der Pharmazie,2019,vol. 352

4
[ 89640-03-9 ]
[ 17231-95-7 ]
[ 1247820-21-8 ]

Yield	Reaction Conditions	Operation in experiment
35%		Sodium metal (0.126 g, 5.5 mmol) was dissolved in absolute ethanol (10 mL) and to the resulting solution was added 2,3-dichlorobenzenethiol (0.895 g, 5 mmol). Ethyl 5- chloro-4-nitrothiophene-2-carboxylate (1.18 g, 5 mmol) was added and the reaction mixture was stirred for 1 hour at ambient temperature and was allowed to stand overnight. After this time, the mixture was diluted with water (30 mL) and the resulting precipitate was collected by filtration and dried in vacuo at 40 0C for 1 hour. Initial analysis showed some minor impurities so the crude material was stirred in absolute ethanol (10 mL) for 30 min, collected by filtration and dried in vacuo at 40 0C for 1 hour to afford the title product as a white solid (0.67 g, 35% yield). 1H NMR (CDCl3) delta: 8.18 (IH, s), 7.71 (2H, m), 7.31 (IH, m), 4.31 (2H, q, J=7.11 Hz), 1.33 (3H, t, J=7.11 Hz).

Reference： [1]Patent: WO2010/114881,2010,A1 .Location in patent: Page/Page column 44

5
[ 89640-03-9 ]
[ 943780-21-0 ]

Reference： [1]Patent: WO2008/133753,2008,A2

6
[ 89640-03-9 ]
[ 943780-18-5 ]

Reference： [1]Patent: WO2008/133753,2008,A2

7
[ 89640-03-9 ]
[ 943780-19-6 ]

Reference： [1]Patent: WO2008/133753,2008,A2

8
[ 89640-03-9 ]
[ 943780-16-3 ]

Reference： [1]Patent: WO2008/133753,2008,A2

9
[ 89640-03-9 ]
[ 943780-20-9 ]

Reference： [1]Patent: WO2008/133753,2008,A2

10
[ 89640-03-9 ]
5‐((5‐(2‐isopropylphenyl)pyridin‐3‐yl)thio)‐4‐nitrothiophene‐2‐carboxylic acid [ No CAS ]