[ CAS No. 75567-84-9 ] {[proInfo.proName]}

Name: 75567-84-9|Methyl 3-(4-bromophenyl)propanoate|98%
Brand: Ambeed
SKU: A156137
Price: 5.0 USD
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Quality Control of [ 75567-84-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 75567-84-9 ]

Product Details of [ 75567-84-9 ]

CAS No. :	75567-84-9	MDL No. :	MFCD09953150
Formula :	C₁₀H₁₁BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FKPYNBFWCSTPOT-UHFFFAOYSA-N
M.W :	243.10	Pubchem ID :	11447883
Synonyms :

Calculated chemistry of [ 75567-84-9 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.81
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) :	-5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.72
Log Po/w (XLOGP3) :	3.01
Log Po/w (WLOGP) :	2.55
Log Po/w (MLOGP) :	2.99
Log Po/w (SILICOS-IT) :	3.06
Consensus Log Po/w :	2.87

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.32
Solubility :	0.116 mg/ml ; 0.000477 mol/l
Class :	Soluble
Log S (Ali) :	-3.23
Solubility :	0.144 mg/ml ; 0.000593 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.14
Solubility :	0.0175 mg/ml ; 0.0000721 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.35

Safety of [ 75567-84-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 75567-84-9 ]

* 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 [ 75567-84-9 ]
Downstream synthetic route of [ 75567-84-9 ]

[ 75567-84-9 ] Synthesis Path-Upstream 1~17

1
[ 75567-84-9 ]
[ 35888-99-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 4013 - 4025

2
[ 1643-30-7 ]
[ 75567-84-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With thionyl chloride In methanol at 70℃; for 2 h;	To a 250 mL round bottom flask was added 3-(4-bromophenyl)propanoic acid 147a (5g, 21.83 mmol, 1.00 equiv.) and methanol (50 mL). Thionyl chloride (7.76 g, 65.23 mmol,5 3.00 equiv.) vva;;; added dropwise with stirring. The resulting mixture was stirred at 70 °C for2h. The reaction was quenched by the addition of water/ice. The aqueous mixture wasextracted with ethyl acetate (200 mL x 3), and the combined organic extracts were washedwith brine (100 mL x 2), dried over anhydrous sodium sulfate and concentrated. The residuewas purified by silica gel column chromatography eluting with PE:EA (5.2percent) to give methyl10 3-(4-bromophenyl)propanoate l47b (4.84 g, 91 ~"0) as a colorless oil

Reference： [1] Patent: WO2018/39386, 2018, A1, . Location in patent: Page/Page column 291; 292

3
[ 1643-30-7 ]
[ 616-38-6 ]
[ 75567-84-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With Novozym 435; acylase I from Aspergillus melleus; amano lipase AK from pseudomonas fluorescens; lipase from wheat germ; papaine In toluene at 40℃; for 48 h; Enzymatic reaction	General procedure: To the solution of acid (1 mmol) in toluene (1 ml), the corresponding dialkyl carbonate (2 mmol) and enzymes (per 4 mg of each enzyme) were added in 5 ml vial. The reaction mixture was stirring for 24 or 48 h at 40 °C in vortex mixture (Heidolph Promax 1020) equipped with incubator (Heidolph Inkubator 1000). After cooling, the mixture was washed with NaHCO₃ (3×) and brine (1×). Organic solvent was removed under vacuum to obtain the product 2a–2r.

Reference： [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 102, p. 225 - 229

4
[ 67-56-1 ]
[ 1643-30-7 ]
[ 75567-84-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	for 16 h; Reflux	General procedure: In distinct reactors, solutions of the appropriate 3-(3-bromophenyl)-propionic acid or 3-(4-Bromophenyl)-propionic acid in MeOH were prepared and concentrated H₂SO₄ was added to each reactor. The resulting mixtures were stirred under reflux for 16h. Each crude mixture was reduced under vacuo and the residues were partitioned with dichloromethane(20 mL) and saturated NaHCO₃solution(20 mL). The organic layers of each reaction was dried with Na₂SO₄, filtered and evaporated. The resulting compounds were used in a further reaction without any further purification.

Reference： [1] Journal of Organic Chemistry, 2010, vol. 75, # 4, p. 1301 - 1304
[2] European Journal of Medicinal Chemistry, 2012, vol. 48, p. 206 - 213
[3] Journal of Organometallic Chemistry, 2002, vol. 657, # 1-2, p. 129 - 135
[4] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 23, p. 9365 - 9372
[5] Journal of Chemical Ecology, 2008, vol. 34, # 3, p. 339 - 352
[6] Patent: WO2011/126567, 2011, A1, . Location in patent: Page/Page column 236
[7] Patent: CN108409585, 2018, A, . Location in patent: Paragraph 0050-0051
[8] Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 44, p. 11797 - 11805

5
[ 67-56-1 ]
[ 23600-77-3 ]
[ 75567-84-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sulfuric acid In water for 18 h; Reflux; Inert atmosphere	General procedure: A stirred solution of the appropriate bromophenyl alkanoic acid(1 eq) in MeOH (25 mL)was treated with H2SO4 (0.1 eq of a conc. aq.solution) and heated at reflux for 18 h. The resultant solution wascooled to room temperature and concentrated under reducedpressure. The resultant oil was diluted with NaHCO3 (50 mL of a sat.aq. solution) and subsequently extracted with diethyl ether(3 25 mL). The combined organics were washed with brine(1 100 mL), dried (MgSO4), filtered and concentrated underreduced pressure to give the desired methyl ester:

Reference： [1] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 1644 - 1656

6
[ 3650-78-0 ]
[ 75567-84-9 ]

Reference： [1] Inorganic Chemistry, 2016, vol. 55, # 5, p. 2345 - 2354

7
[ 3650-78-0 ]
[ 75567-84-9 ]

Reference： [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 33, p. 7347 - 7352
[2] Chemical Communications, 2013, vol. 49, # 33, p. 3470 - 3472

8
[ 5467-74-3 ]
[ 292638-85-8 ]
[ 75567-84-9 ]

Reference： [1] Chemistry - A European Journal, 2012, vol. 18, # 47, p. 14918 - 14922

9
[ 5927-18-4 ]
[ 1122-91-4 ]
[ 75567-84-9 ]

Reference： [1] Chemistry Letters, 1998, # 3, p. 203 - 204

10
[ 589-87-7 ]
[ 292638-85-8 ]
[ 75567-84-9 ]

Reference： [1] Journal of Organic Chemistry, 2014, vol. 79, # 4, p. 1529 - 1541

11
[ 1122-91-4 ]
[ 75567-84-9 ]

Reference： [1] Journal of Organometallic Chemistry, 2002, vol. 657, # 1-2, p. 129 - 135
[2] European Journal of Organic Chemistry, 2014, vol. 2014, # 33, p. 7347 - 7352

12
[ 292638-85-8 ]
[ 589-21-9 ]
[ 75567-84-9 ]
[ 126558-70-1 ]

Reference： [1] Tetrahedron Letters, 1989, vol. 30, # 35, p. 4709 - 4712

13
[ 4489-22-9 ]
[ 75567-84-9 ]

Reference： [1] Journal of Organometallic Chemistry, 2002, vol. 657, # 1-2, p. 129 - 135

14
[ 4489-23-0 ]
[ 75567-84-9 ]

Reference： [1] Journal of Organometallic Chemistry, 2002, vol. 657, # 1-2, p. 129 - 135

15
[ 25574-11-2 ]
[ 75567-84-9 ]

Reference： [1] Journal of Organometallic Chemistry, 2002, vol. 657, # 1-2, p. 129 - 135

16
[ 589-87-7 ]
[ 75567-84-9 ]

Reference： [1] Inorganic Chemistry, 2016, vol. 55, # 5, p. 2345 - 2354

17
[ 186581-53-3 ]
[ 1643-30-7 ]
[ 75567-84-9 ]

Reference： [1] Journal of the Chemical Society, 1936, p. 402,404
[2] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1980, vol. 35, # 7, p. 934 - 936

[ 75567-84-9 ] Synthesis Path-Downstream 1~88

1
[ 292638-85-8 ]
[ 589-21-9 ]
[ 75567-84-9 ]
[ 126558-70-1 ]

Reference： [1]Tetrahedron Letters,1989,vol. 30,p. 4709 - 4712

2
[ 4489-22-9 ]
[ 75567-84-9 ]

Reference： [1]Journal of Organometallic Chemistry,2002,vol. 657,p. 129 - 135

3
[ 4489-23-0 ]
[ 75567-84-9 ]

Reference： [1]Journal of Organometallic Chemistry,2002,vol. 657,p. 129 - 135

4
[ 25574-11-2 ]
[ 75567-84-9 ]

Reference： [1]Journal of Organometallic Chemistry,2002,vol. 657,p. 129 - 135

5
[ 1122-91-4 ]
[ 75567-84-9 ]

Reference： [1]Journal of Organometallic Chemistry,2002,vol. 657,p. 129 - 135
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 7347 - 7352

6
[ 75567-84-9 ]
[ 153993-80-7 ]