[ CAS No. 24552-27-0 ] {[proInfo.proName]}

Name: 24552-27-0|Phenyl 3-chloropropanoate|95%
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3d Animation Molecule Structure of 24552-27-0

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COA NMR CNMR HPLC LC-MS

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Product Details of [ 24552-27-0 ]

CAS No. :	24552-27-0	MDL No. :	MFCD00045298
Formula :	C₉H₉ClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RAFRTSDUWORDLA-UHFFFAOYSA-N
M.W :	184.62	Pubchem ID :	141118
Synonyms :

Calculated chemistry of [ 24552-27-0 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.54
TPSA :	26.3 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) :	-5.69 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.07
Log Po/w (XLOGP3) :	2.44
Log Po/w (WLOGP) :	2.22
Log Po/w (MLOGP) :	2.55
Log Po/w (SILICOS-IT) :	2.54
Consensus Log Po/w :	2.36

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.63
Solubility :	0.435 mg/ml ; 0.00236 mol/l
Class :	Soluble
Log S (Ali) :	-2.64
Solubility :	0.427 mg/ml ; 0.00231 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.51
Solubility :	0.0568 mg/ml ; 0.000308 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.56

Safety of [ 24552-27-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 24552-27-0 ]

* 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 [ 24552-27-0 ]
Downstream synthetic route of [ 24552-27-0 ]

[ 24552-27-0 ] Synthesis Path-Upstream 1~1

1
[ 24552-27-0 ]
[ 6968-35-0 ]

Reference： [1] Canadian Journal of Chemistry, 2005, vol. 83, # 5, p. 413 - 419
[2] Tetrahedron Letters, 2011, vol. 52, # 47, p. 6234 - 6237
[3] Heterocycles, 1988, vol. 27, # 2, p. 407 - 422
[4] Chemische Berichte, 1924, vol. 57, p. 201,618
[5] Patent: WO2016/1875, 2016, A1, . Location in patent: Page/Page column 68

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Yield	Reaction Conditions	Operation in experiment
50%	With aluminum (III) chloride; at 90 - 180℃; for 3h;	67a (1.3 g, 7.1 mmol) and aluminum trichloride (2.8 g, 21.3 mmol, 3 equivalents) were placed in a dry round bottom flask, warmed to 90 C, and allowed to warm up to 165 C after 1 hour. , the reaction was 1 h, and the temperature was further raised to 180 C for 2 h. Cooled, poured into a mixed solution of hydrochloric acid and ice water, extracted three times with ethyl acetate, washed three times with saturated brine, combined organicIn addition to the solvent, column chromatography gave 67b (430 mg, white acicular solid).The yield is 50%.
	With aluminum (III) chloride; at 100 - 180℃; for 3h;	As described in Heterocycles, 27(2), 407-21 ; 1988, a mixture of phenyl 3- chloropropanoate (CAS 24552-27-0, 7 g, 37.9 mmol) and AICI3 (20.22 g, 152 mmol) was heated at 100 C for 1 h, then at 180 C for 2 h, and subsequently cooled to room temperature. The excess AICI3 was then quenched with 1 N HCI. The resulting mixture was extracted with DCM. The combined organic layers were washed with water, passed through an ISOLUTE phase separator. The filtrate was concentrated to give 7-hydroxy-2,3-dihydro-1 H-inden-1 -one. 1H NMR (400 MHz, Chloroform-d) delta 9.07 (s, 1 H), 7.47 (t, J = 7.8 Hz, 1 H), 6.97 - 6.92 (m, 1 H), 6.78 - 6.74 (m, 1 H), 3.16 - 3.06 (m, 2H), 2.78 - 2.68 (m, 2H).

Yield	Reaction Conditions	Operation in experiment
62%	With aluminium trichloride; nitrobenzene 1) 70 deg C, 3 h, 2) r.t., 24 h;
53%	With trifluorormethanesulfonic acid at 20℃; for 4h;	11.2 Step-2: Preparation of 3-chloro-l-(4-hydroxyphenyl)propan-l-one Step-2: Preparation of 3-chloro-l-(4-hydroxyphenyl)propan-l-one [0140] A mixture of phenyl 3-chloropropanoate (1.0 g, 5.41 mmol) and trifluoromethanesulfomc acid (2.4 g, 27.0 mmol) were taken in round bottomed flask and stirred for 4 h. After completion of reaction (monitored by TLC), the mixture was concentrated under vacuum. The residue was diluted with ethyl acetate (100 mL), washed with 20 % sodium bicarbonate solution (20 mL x 3), water (25 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford the crude compound, which was purified by silica gel column chromatography (30% ethyl acetate/hexane) to obtain the title compound 3-chloro-l-(4-hydroxyphenyl)propan-l-one (0.53 g, 53 % yield) as a white solid. Calculated (M-H): 183.03; Found (M-H): 183.1.
	With aluminium trichloride at 100℃;

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydroxide In water
66.4%	In toluene for 1h; Cooling; Reflux;	67 Method for preparing intermediate 67-8-methoxy-1,2,3,4-tetrahydroisoquinoline Phenol (1 g, 10.64 mmol) was dissolved in 25 mL of toluene, and 3-chloropropanoyl chloride (1.1 mL, 11.7 mmol, 1.1 eq.) was added dropwise in an ice bath, and the mixture was refluxed for 1 hour. Add water and extract with ethyl acetate three times.Wash three times with saturated brine, combine the organic phases, and dry.Evaporate the solvent under reduced pressure.Column chromatography gave 67a (1.3 g, white solid).The yield was 66.4%.
60%	With pyridine In dichloromethane for 12h; Ambient temperature;

25%	at 100℃; for 16h;	11.1 Step-1: Preparation of phenyl 3-chloropropanoate Step-1: Preparation of phenyl 3-chloropropanoate [0139] A mixture of phenol (5g, 53.1 mmol) and 3-chloropropanoyl chloride (8.09 g, 63.7 mmol) were taken in round bottomed flask. The resulting mixture was heated to 100 °C and stirred for 16 h. After completion of reaction (monitored by TLC), the reaction mixture was allowed to cool to room temperature, poured in to ice water (100 mL), extracted with ethyl acetate (100 mL x 3). The combined organic layer was washed with 1M sodium hydroxide solution (100 mL x 2), water (50 mL x 2), brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford crude compound which was purified by silica gel column chromatography (5% ethyl acetate/hexane) to obtain the title compound phenyl 3-chloropropanoate (2.5 g, 25% yield) as a colorless liquid. 1H NMR (400 MHz, CdC13) δ 7.38 (t, J = 7.6 Hz,2H), 7.24 (t, J = 7.6 Hz, 1 H), 7.11 (t, J 3.87 (t, J = 6.4 Hz, 2 H), 3.05 (t, J = 6.8 Hz, 2 H).
	at 140℃;
	With trichlorophosphate
	With carbon disulfide; aluminium trichloride
92.5 g	In toluene for 3h; Heating;
	With triethylamine In dichloromethane at 0 - 20℃; for 17h; Inert atmosphere;

[ CAS No. 24552-27-0 ] {[proInfo.proName]}

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