[ CAS No. 70958-20-2 ] {[proInfo.proName]}

Name: 70958-20-2|2-(5-Chloro-2-phenoxyphenyl)acetic acid|97%
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SKU: A244634
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Quality Control of [ 70958-20-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 70958-20-2 ]

SDS Specification

Alternatived Products of [ 70958-20-2 ]

Product Details of [ 70958-20-2 ]

CAS No. :	70958-20-2	MDL No. :	MFCD07368830
Formula :	C₁₄H₁₁ClO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PKMKNEIUKHPJAX-UHFFFAOYSA-N
M.W :	262.69	Pubchem ID :	12765114
Synonyms :

Calculated chemistry of [ 70958-20-2 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.07
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	69.51
TPSA :	46.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.39 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.41
Log Po/w (XLOGP3) :	3.54
Log Po/w (WLOGP) :	3.76
Log Po/w (MLOGP) :	3.32
Log Po/w (SILICOS-IT) :	3.42
Consensus Log Po/w :	3.29

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.93
Solubility :	0.031 mg/ml ; 0.000118 mol/l
Class :	Soluble
Log S (Ali) :	-4.2
Solubility :	0.0165 mg/ml ; 0.0000628 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.05
Solubility :	0.00233 mg/ml ; 0.00000887 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.08

Safety of [ 70958-20-2 ]

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 [ 70958-20-2 ]

* 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 [ 70958-20-2 ]
Downstream synthetic route of [ 70958-20-2 ]

[ 70958-20-2 ] Synthesis Path-Upstream 1~6

1
[ 70958-20-2 ]
[ 85650-56-2 ]

Reference： [1] Patent: EP2468751, 2012, A2,

2
[ 70958-18-8 ]
[ 70958-20-2 ]

Yield	Reaction Conditions	Operation in experiment
67.1%	Stage #1: at 110℃; for 12 h; Stage #2: With hydrogenchloride; acetic acid In water for 8 h; Reflux	Example 14. Synthesis of 5-chloro-2-phenoxyphenylacetic acid (compound XIVa) [Show Image] A mixture of 200 g (0.81 mol) of 5-chloro-2-phenoxyacetophenone (compound XV), as obtained in Example 13, 112.3 g (1.29 mol) of morpholine and 40 g (1.25 mol) of sulfur was stirred at 110 C for 12 hours. After cooling to room temperature, 1 L of glacial acetic acid and 1 L of concentrated aqueous hydrochloric acid were added, and the resulting mixture was stirred at reflux temperature for 8 hours. The reaction mixture was concentrated to about 1/3 of its initial volume. Then, 800 mL of water and 800 mL of methyl tert-butyl ether were added. The aqueous layer was separated, washed with 400 mL of methyl tert-butyl ether, and discarded. The organic phases were combined and washed subsequently with 1 x 500 mL and 2 x 250 mL of an 8 percent aqueous solution of sodium carbonate. The aqueous phases were combined, washed with 2 x 200 mL of methyl tert-butyl ether, and acidified to pH 1 with concentrated hydrochloric acid. 400 mL of petroleum ether were added, and the resulting mixture was stirred at room temperature for 30 minutes. The suspension was filtered, and the solid was dried until constant weight to obtain 143 g of 5-chloro-2-phenoxyphenylacetic acid (compound XIVa). Yield: 67.1 percent.

Reference： [1] Patent: EP2468751, 2012, A2, . Location in patent: Page/Page column 21
[2] Journal of Medicinal Chemistry, 1982, vol. 25, # 7, p. 855 - 858
[3] Journal of Medicinal Chemistry, 1983, vol. 26, # 10, p. 1353 - 1360

3
[ 2476-37-1 ]
[ 70958-20-2 ]

Reference： [1] Journal of Medicinal Chemistry, 1982, vol. 25, # 7, p. 855 - 858
[2] Journal of Medicinal Chemistry, 1983, vol. 26, # 10, p. 1353 - 1360
[3] Patent: EP2468751, 2012, A2,

4
[ 70958-19-9 ]
[ 70958-20-2 ]

Reference： [1] Journal of Medicinal Chemistry, 1983, vol. 26, # 10, p. 1353 - 1360

5
[ 108-95-2 ]
[ 70958-20-2 ]

Reference： [1] Patent: EP2468751, 2012, A2,

6
[ 70958-20-2 ]
[ 1012884-46-6 ]

Reference： [1] Organic Process Research and Development, 2008, vol. 12, # 2, p. 196 - 201

[ 70958-20-2 ] Synthesis Path-Downstream 1~25

1
[ 70958-18-8 ]
[ 70958-20-2 ]

Yield	Reaction Conditions	Operation in experiment
67.1%		Example 14. Synthesis of 5-chloro-2-phenoxyphenylacetic acid (compound XIVa) [Show Image] A mixture of 200 g (0.81 mol) of 5-chloro-2-phenoxyacetophenone (compound XV), as obtained in Example 13, 112.3 g (1.29 mol) of morpholine and 40 g (1.25 mol) of sulfur was stirred at 110 ºC for 12 hours. After cooling to room temperature, 1 L of glacial acetic acid and 1 L of concentrated aqueous hydrochloric acid were added, and the resulting mixture was stirred at reflux temperature for 8 hours. The reaction mixture was concentrated to about 1/3 of its initial volume. Then, 800 mL of water and 800 mL of methyl tert-butyl ether were added. The aqueous layer was separated, washed with 400 mL of methyl tert-butyl ether, and discarded. The organic phases were combined and washed subsequently with 1 x 500 mL and 2 x 250 mL of an 8 % aqueous solution of sodium carbonate. The aqueous phases were combined, washed with 2 x 200 mL of methyl tert-butyl ether, and acidified to pH 1 with concentrated hydrochloric acid. 400 mL of petroleum ether were added, and the resulting mixture was stirred at room temperature for 30 minutes. The suspension was filtered, and the solid was dried until constant weight to obtain 143 g of 5-chloro-2-phenoxyphenylacetic acid (compound XIVa). Yield: 67.1 %.

Reference： [1]Patent: EP2468751,2012,A2 .Location in patent: Page/Page column 21
[2]Journal of Medicinal Chemistry,1982,vol. 25,p. 855 - 858
[3]Journal of Medicinal Chemistry,1983,vol. 26,p. 1353 - 1360

2
[ 70958-20-2 ]
[ 55595-54-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; PPA;	EXAMPLE 3 2-Chlorodibenzo[b,f]oxepin-10(11H)-one Polyphosphoric acid, 500 grams, is heated to 120 C. and 30.5 grams of <strong>[70958-20-2](5-chloro-2-phenoxyphenyl)acetic acid</strong>, prepared in accordance with the procedure of Example 2, is slowly added under an atmosphere of nitrogen with stirring. The reaction mixture is maintained at 120 C. for a period of about two hours, poured over a mixture of ice and water, and extracted into ethyl ether. The combined ether extracts are washed with water until the water washings appear neutral, extracted with a 2 N solution of sodium hydroxide, washed again with water until the water washings are neutral, dried over anhydrous sodium sulfate and filtered. The dried organic solvent is removed from the filtrate by distillation and the residue distilled in vacuo to yield 21 grams of 2-chlorodibenzo[b,f]oxepin-10(11H)-one having a b.p. of 127-134 C./0.005 mm Hg. Upon recrystallization from methanol, a compound is obtained having an m.p. of 75-76 C.

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 855 - 858
[2]Patent: US4180559,1979,A

3
[ 70958-19-9 ]
[ 70958-20-2 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1353 - 1360

4
[ 70958-20-2 ]
(5-Chloro-2-phenoxy-phenyl)-acetyl chloride [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1994,vol. 34,p. 845 - 869
[2]Organic Process Research and Development,2008,vol. 12,p. 196 - 201

5
[ 2476-37-1 ]
[ 70958-20-2 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 855 - 858
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 1353 - 1360
[3]Patent: EP2468751,2012,A2

6
[ 70958-20-2 ]
[ 57389-06-7 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 855 - 858

7
[ 108-95-2 ]
(+-)-1-<1-chloro-cyclohexyl>-cyclohexanone-(2) [ No CAS ]
[ 70958-20-2 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 855 - 858

8
[ 139-02-6 ]
2-methoxy-<i>m</i>-phenylene disodium [ No CAS ]
[ 70958-20-2 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1353 - 1360

Yield	Reaction Conditions	Operation in experiment
		To this morpholine residue is added 290 ml of glacial acetic acid, 61 ml of water and 87 ml of sulfuric acid (96%), and the mixture refluxed for a period of 21 hours. On cooling, the reaction mixture is dissolved in ethyl ether, washed with water until the water wash appears neutral and extracted with a 10% sodium carbonate solution. The aqueous alkaline layer is acidified with a 2 N solution of hydrochloric acid and re-extracted into diethyl ether. The ether solution is washed with water until the water washings are neutral, dried over anhydrous sodium sulfate and filtered. The solvent is removed by distillation from the filtrate and the remaining residue is crystallized from cyclohexane to yield 30.5 grams of (5-chloro-2-phenoxyphenyl)acetic acid having a m.p. of 119-123 C.

10
[ 108-95-2 ]
[ 70958-20-2 ]