[ CAS No. 1813-93-0 ] {[proInfo.proName]}

Name: 1813-93-0|Ethyl 2-(2-fluorophenyl)-2-oxoacetate|95%
Brand: Ambeed
SKU: A166570
Price: 83.0 USD
Availability: InStock
Rating: 93 (35 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 1813-93-0

Structure of 1813-93-0 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 1813-93-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1813-93-0 ]

SDS Specification

Alternatived Products of [ 1813-93-0 ]

Product Details of [ 1813-93-0 ]

CAS No. :	1813-93-0	MDL No. :	MFCD09801420
Formula :	C₁₀H₉FO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YMBISXZGELJNMH-UHFFFAOYSA-N
M.W :	196.18	Pubchem ID :	21644544
Synonyms :

Calculated chemistry of [ 1813-93-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.49
TPSA :	43.37 Å²

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) :	-5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.65
Log Po/w (XLOGP3) :	2.12
Log Po/w (WLOGP) :	1.99
Log Po/w (MLOGP) :	1.73
Log Po/w (SILICOS-IT) :	2.37
Consensus Log Po/w :	1.97

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.45
Solubility :	0.704 mg/ml ; 0.00359 mol/l
Class :	Soluble
Log S (Ali) :	-2.66
Solubility :	0.427 mg/ml ; 0.00218 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.11
Solubility :	0.152 mg/ml ; 0.000776 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.86

Safety of [ 1813-93-0 ]

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 [ 1813-93-0 ]

* 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 [ 1813-93-0 ]
Downstream synthetic route of [ 1813-93-0 ]

[ 1813-93-0 ] Synthesis Path-Upstream 1~5

1
[ 1072-85-1 ]
[ 95-92-1 ]
[ 1813-93-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -70℃; Inert atmosphere Stage #2: at -70 - 20℃;	To a stirring solution of 1- bromo-2-fluorobenzene (lOg, 57 mmol) in tetrahydrofuran (100 mL) at -70 °C under nitrogen was added a solution of n-butyllithium (25 mL, 62.9 mmol, 2.5 M in hexane). After 20 minutes, this solution was added to a solution of diethyl oxalate (39 mL, 285 mmol) in tetrahydrofuran (100 mL) at -70 °C. Upon complete addition, the reaction mixture was allowed to warm to ambient temperature. After one hour at ambient temperature, the reaction mixture was poured into water (150 mL) and the mixture was extracted with ethyl acetate (2 x 100 mL). The organic layers were combined and concentrated at reduced pressure. The resulting crude product was purified by column chromatography through silica gel cartridge (240 g) eluting with ethyl acetate/hexane(1 :49) to give the product as a colorless oil (5.6 g, 50percent). 1H NMR (CDC1₃) δ 7.95 (m, 1H,), 7.62 (m, 1H), 7.35-7.13 (m, 2H), 4.44 (q, J = 7.1 Hz, 2H), 1.40 (t, J = 7.1 Hz, 3H). MS(ES⁺) = 197(M+H)⁺.

Reference： [1] Patent: WO2012/74784, 2012, A2, . Location in patent: Page/Page column 23-24
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3726 - 3732
[3] Angewandte Chemie - International Edition, 2014, vol. 53, # 10, p. 2658 - 2661[4] Angew. Chem., 2014, vol. 126, # 10, p. 2696 - 2699,4

2
[ 1072-85-1 ]
[ 109-72-8 ]
[ 75716-82-4 ]
[ 1813-93-0 ]

Reference： [1] Patent: EP386940, 1990, A1,

3
[ 348-52-7 ]
[ 4755-77-5 ]
[ 1813-93-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 24, p. 7176 - 7180[2] Angew. Chem., 2018, vol. 130, # 24, p. 7294 - 7298,5

4
[ 446-52-6 ]
[ 1813-93-0 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1964, vol. 29, p. 97 - 120

5
[ 64-17-5 ]
[ 389-31-1 ]
[ 1813-93-0 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1964, vol. 29, p. 97 - 120

[ 1813-93-0 ] Synthesis Path-Downstream 1~43

1
[ 64-17-5 ]
[ 389-31-1 ]
[ 1813-93-0 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1964,vol. 29,p. 97 - 120

2
[ 1813-93-0 ]
[ 931-50-0 ]
[ 1962-25-0 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1964,vol. 29,p. 97 - 120

4
[ 1813-93-0 ]
[ 2262-17-1 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1964,vol. 29,p. 97 - 120

5
[ 446-52-6 ]
[ 1813-93-0 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1964,vol. 29,p. 97 - 120

6
[ 1813-93-0 ]
[ 847866-70-0 ]

Yield	Reaction Conditions	Operation in experiment
		16.8 mL of a hexane-cyclohexane solution of 1.0 mol/L sec-butyllithium was added dropwise under -78C cooling to a 15 mL tetrahydrofuran solution of 2 g of tert-butyl [4-(trifluoromethyl)phenyl]carbamate, and the reaction mixture was stirred for 1 hour. The temperature was then raised to -40C, and the reaction mixture was stirred for 2.5 hours at that temperature. The reaction mixture was cooled back down to -78C, a 7.5 mL tetrahydrofuran solution of 2.23 g of <strong>[1813-93-0]ethyl (2-fluorophenyl)(oxo)acetate</strong> was added dropwise, and the reaction mixture was stirred for 2 hours at the same temperature. The temperature was then raised to room temperature, and the reaction mixture was stirred for 12 hours. A saturated ammonium chloride aqueous solution was added to the reaction solution, extraction was performed with ethyl acetate, the organic layer was washed with saturated brine and dried with magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/hexane = 1/1; v/v) to obtain 389 mg of the titled compound (colorless powder). MS (ESI pos.) m/z : 334([M+Na]+), (ESI neg.) m/z : 332([M-H]-) 1 H-NMR (300 MHz, DMSO-d6) delta (ppm) ; 7.01-7.13 (m, 2 H), 7.18 (d, J=1.9 Hz, 1 H), 7.29-7.45 (m, 2 H), 7.59-7.68 (m, 1 H), 7.88-8.02 (m, 1 H), 10.95 (s, 1 H)

Reference： [1]Patent: EP1659121,2006,A1 .Location in patent: Page/Page column 31

7
[ 1072-85-1 ]
[ 109-72-8 ]
ethyl acetate n-hexane [ No CAS ]
[ 75716-82-4 ]
[ 1813-93-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	In diethyl ether; hexane; water; sodium;	(a) Ethyl 2-Fluoro-alpha-oxo-benzeneacetate 1.6M n-Butyllithium solution in hexane (8.59ml) was added over 10 min. to a solution of 2-fluorobromobenzene (1.43ml) in sodium dried diethyl ether (20ml) cooled to -69C under an argon atmosphere. During the addition the temperature was kept below -60C. This mixture was added to a solution of ethyl alpha-oxo-1H-imidazole-1-acetate (11.52g) in sodium dried diethyl ether (110ml) cooled to -47C under an argon atmosphere over 3 min via a double tipped needle. The mixture was stirred at -40C for 15 min, then allowed to warm up. The mixture was mixed with water (150ml) and the phases separated. The aqueous phase was extracted with diethyl ether (100ml). The combined organic phases were washed with water (2x50ml) and with saturated sodium chloride solution (50ml), dried over magnesium sulphate and concentrated in vacuo . The crude product was chromatographed [Kieselgel 60, hexane-ethyl acetate (19:1)-(9:1)] to give the title compound (1.41g, 55%) as an oil. (Found: M + 196.0537. C10H9O3F requires M 196.0536). numax(film) 1745, 1695, 1615, 1585, 1485, 1460, 1200, 1020cmmin1; deltaH(CDCl3) 1.38 (3H, t, J 7Hz) 4.40 (2H, q, J 7Hz), 7.0-7.45 (2H, m), 7.45-7.8 (1H, m), 7.8-8.1 (1H, m); m / z CI (NH3 gas) MNH 4+, 214.

Reference： [1]Patent: EP386940,1990,A1

8
ethyl acetate n-hexane [ No CAS ]
[ 1813-93-0 ]
[ 132115-94-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; In ethanol; water;	(b) Ethyl 2-Fluoro-alpha-(Z-hydroxyimino)benzeneacetate Hydroxylamine hydrochloride (0.89g) was added to ethyl 2-fluoro-alpha-oxo-benzeneacetate (2.46g) in ethanol (10ml), followed by water (1ml). The reaction mixture was stirred for 18hrs, then partitioned between ethyl acetate (25ml) and water (15ml). The aqueous phase was extracted with ethyl acetate (15ml) and the combined organic extracts washed with water and saturated sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo . The crude product (3.0g) was chromatographed [Kieselgel 60, ethyl acetate-hexane (1:9)-(1:4)] to give the E isomer (0.98g) and the title compound (1.51g, 57%) (Found: M + 211.0651. C10H10NO3F requires M 211.0645); numax(film) 3375(br), 1730, 1615, 1595, 1490, 1265 and 955cmmin1; deltaH(CDCl3) 1.33 (3H, t, J 7Hz), 4.38 (2H, q, J 7Hz), 6.8-7.75 (4H, m), 10.09 (1H, s); m / z (EI) M +, 211.

Reference： [1]Patent: EP386940,1990,A1

9
[ 1813-93-0 ]
[ 141940-37-6 ]
[ 847866-70-0 ]

Yield	Reaction Conditions	Operation in experiment
		Step 27-1: Synthesis of 3-(2-fluorophenyl)-3-hydroxy-5-(trifluoromethyl)-1,3-dihydro-2H-indol-2-one To a solution of 2 g of tert-butyl[4-(trifluoromethyl)phenyl]carbamate in THF (15 ml) under cooling at -78 C. was added dropwise a solution of 1.0 mol/L sec-butyl lithium in cyclohexane (16.8 ml) and the reaction mixture was stirred for 1 hour. Thereafter, the solution was warmed to -40 C. and stirred under the same temperature condition for two hours. The solution was cooled again to -78 C., a solution of 2.23 g of <strong>[1813-93-0]ethyl (2-fluorophenyl)(oxo) acetate</strong> in THF (7.5 ml) was added dropwise, and the reaction mixture was stirred under the same temperature condition for two hours. Thereafter, the solution was warmed to room temperature and stirred for 12 hours. To the reaction solution was added a saturated aqueous solution of NH4Cl and the resulting mixture was extracted with EtOAc. The organic layer was washed with saturated brine, dried over MgSO4, then and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/1; v/v) to obtain 389 mg of the title compound (colorless powder). MS (ESI pos.) m/z: 334 ([M+Na]+), (ESI neg.) m/z: 332 ([M-H]-) 1H-NMR (300 MHz, DMSO-d6) delta (ppm); 7.01-7.13 (m, 2H), 7.18 (d, J=1.9 Hz, 1H), 7.29-7.45 (m, 2H), 7.59-7.68 (m, 1H), 7.88-8.02 (m, 1H), 10.95 (s, 1H)

Reference： [1]Patent: US2008/318923,2008,A1 .Location in patent: Page/Page column 67

10
[ 1813-93-0 ]
[ 172851-95-5 ]
[ 1352130-06-3 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 489 - 502

11
[ 1072-85-1 ]
[ 95-92-1 ]
[ 1813-93-0 ]

Yield	Reaction Conditions	Operation in experiment
50%		To a stirring solution of 1- bromo-2-fluorobenzene (lOg, 57 mmol) in tetrahydrofuran (100 mL) at -70 C under nitrogen was added a solution of n-butyllithium (25 mL, 62.9 mmol, 2.5 M in hexane). After 20 minutes, this solution was added to a solution of diethyl oxalate (39 mL, 285 mmol) in tetrahydrofuran (100 mL) at -70 C. Upon complete addition, the reaction mixture was allowed to warm to ambient temperature. After one hour at ambient temperature, the reaction mixture was poured into water (150 mL) and the mixture was extracted with ethyl acetate (2 x 100 mL). The organic layers were combined and concentrated at reduced pressure. The resulting crude product was purified by column chromatography through silica gel cartridge (240 g) eluting with ethyl acetate/hexane(1 :49) to give the product as a colorless oil (5.6 g, 50%). 1H NMR (CDC13) delta 7.95 (m, 1H,), 7.62 (m, 1H), 7.35-7.13 (m, 2H), 4.44 (q, J = 7.1 Hz, 2H), 1.40 (t, J = 7.1 Hz, 3H). MS(ES+) = 197(M+H)+.

Reference： [1]Patent: WO2012/74784,2012,A2 .Location in patent: Page/Page column 23-24
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 3726 - 3732
[3]Angewandte Chemie - International Edition,2014,vol. 53,p. 2658 - 2661
Angew. Chem.,2014,vol. 126,p. 2696 - 2699,4

12
[ 1813-93-0 ]
ethyl α,α-difluoro-α-(o-fluorophenyl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In toluene; at 70℃; for 16h;	To a stirring solution of <strong>[1813-93-0](2-fluorophenyl)-oxo-acetic acid ethyl ester</strong> (l.Og, 5.0 mmol) in toluene (15 mL) was added [bis(2-methoxyethyl)amino]sulfur trifluoride (2.07 mL, 2.48 mmol) and the resulting solution was heated at 70 C for 16 hours. The reaction mixture was cooled to ambient temperature, diluted with ethyl acetate (75 mL) and washed with saturated aqueous sodium hydrogen carbonate (75 mL). The organic layer was separated and concentrated at reduced pressure. The resulting crude product was purified by column chromatography through silica gel cartridge (24 g) eluting with ethyl acetate/hexane(1 :49) to give the product as a colorless oil (670 mg, 61%). 1H NMR (CDC13) delta 7.62 (m, 1H,), 7.50 (m, 1H), 7.30-7.12 (m, 2H), 4.35 (q, J = 7.2 Hz, 2H), 1.35 (t, J = 7.2 Hz, 3H). MS(ES+) = 219(M+H)+.

Reference： [1]Patent: WO2012/74784,2012,A2 .Location in patent: Page/Page column 24

13
[ 1813-93-0 ]
[ 1380202-32-3 ]

Reference： [1]Patent: WO2012/74784,2012,A2

14
[ 1813-93-0 ]
[ 1380202-34-5 ]

Reference： [1]Patent: WO2012/74784,2012,A2

15
[ 1813-93-0 ]
[ 1380202-36-7 ]

Reference： [1]Patent: WO2012/74784,2012,A2

16
[ 1813-93-0 ]
[ 1380201-88-6 ]

Reference： [1]Patent: WO2012/74784,2012,A2

17
[ 1813-93-0 ]
C₁₁H₁₁FO₄ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 12912 - 12915

18
[ 1813-93-0 ]
[ 1392008-24-0 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 12912 - 12915

19
[ 1813-93-0 ]
[ 108199-32-2 ]
[ 1392008-14-8 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 12912 - 12915

20
[ 1813-93-0 ]
tert-butyl 2-(2-fluorophenyl)-2-oxoacetate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1937 - 1942

21
[ 1813-93-0 ]
C₈H₄ClFO₂ [ No CAS ]

22
[ 1813-93-0 ]
tert-butyl (2E)-2-(2-fluorophenyl)-2-((4-methoxyphenyl)imino)acetate [ No CAS ]
tert-butyl (2Z)-2-(2-fluorophenyl)-2-((4-methoxyphenyl)imino)acetate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1937 - 1942

23
[ 1813-93-0 ]
[ 79477-86-4 ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1937 - 1942
[2]Angewandte Chemie - International Edition,2014,vol. 53,p. 2658 - 2661
Angew. Chem.,2014,vol. 126,p. 2696 - 2699,4
[3]Chemical Communications,2014,vol. 50,p. 4489 - 4491
[4]Angewandte Chemie - International Edition,2018,vol. 57,p. 7176 - 7180
Angew. Chem.,2018,vol. 130,p. 7294 - 7298,5

24
[ 1813-93-0 ]
[ 1613439-85-2 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 2658 - 2661
Angew. Chem.,2014,vol. 126,p. 2696 - 2699,4

25
[ 1813-93-0 ]
3-(2-fluorophenyl)-3-hydroxy-4-(N,N-dimethylaminocarbonyl)indolin-2-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 2658 - 2661
Angew. Chem.,2014,vol. 126,p. 2696 - 2699,4

26
[ 1813-93-0 ]
isopropyl 2-(2-fluorophenyl)-2-hydroxyacetate [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 4489 - 4491

27
[ 1813-93-0 ]
[ 1596279-14-9 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 4489 - 4491

28
[ 1813-93-0 ]
[ 1596278-73-7 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 4489 - 4491

29
[ 614-20-0 ]
[ 1813-93-0 ]
[ 1642594-38-4 ]
C₁₈H₁₇FO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With scandium tris(trifluoromethanesulfonate); (S,S)-2,6-bis(4-phenyl-2-oxazolinyl)pyridine; In chloroform; at 0℃; for 48h;Inert atmosphere; Schlenk technique; Sealed tube;	General procedure: A dry Schlenk tube under N2 atmosphere was charged with Sc(OTf)3 (0.01 mmol, 0.1 equiv.) and pyBOX 6a (0.012 mmol, 0.12 equiv.). Dry CHCl3 (0.5 mL) was added and the solution was stirred at 0C for 30 min. Subsequently, alpha-keto ester (0.1 mmol), beta-keto acid (0.2 mmol, 2.0 equiv.) were added and the Schlenk tube was sealed. After complete consumption of starting material (0C, 48 hours, TLC control), the solvent was evaporated under reduced pressure, the residue was purified by a flash column chromatography on silica gel to afford the desired adducts and the ee values were determined by HPLC analysis with chiral column.

Reference： [1]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 969 - 974

30
[ 1813-93-0 ]
[ 107-15-3 ]
C₁₀H₉FN₂O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 3726 - 3732

31
[ 348-52-7 ]
[ 4755-77-5 ]
[ 1813-93-0 ]