[ CAS No. 183483-29-6 ] {[proInfo.proName]}

Name: 183483-29-6|2-(2-Bromopyridin-4-yl)acetic acid|95%
Brand: Ambeed
SKU: A318178
Price: 14.0 USD
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Quality Control of [ 183483-29-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 183483-29-6 ]

SDS Specification

Alternatived Products of [ 183483-29-6 ]

Product Details of [ 183483-29-6 ]

CAS No. :	183483-29-6	MDL No. :	MFCD07367935
Formula :	C₇H₆BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SJFRXYCVLZOAEU-UHFFFAOYSA-N
M.W :	216.03	Pubchem ID :	29921601
Synonyms :

Calculated chemistry of [ 183483-29-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.48
TPSA :	50.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.32
Log Po/w (XLOGP3) :	1.34
Log Po/w (WLOGP) :	1.47
Log Po/w (MLOGP) :	0.82
Log Po/w (SILICOS-IT) :	1.72
Consensus Log Po/w :	1.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.3
Solubility :	1.09 mg/ml ; 0.00507 mol/l
Class :	Soluble
Log S (Ali) :	-2.0
Solubility :	2.18 mg/ml ; 0.0101 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.66
Solubility :	0.469 mg/ml ; 0.00217 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.82

Safety of [ 183483-29-6 ]

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

Application In Synthesis of [ 183483-29-6 ]

* 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 [ 183483-29-6 ]
Downstream synthetic route of [ 183483-29-6 ]

[ 183483-29-6 ] Synthesis Path-Upstream 1~3

1
[ 1256337-24-2 ]
[ 183483-29-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 0.166667 h;	To a solution of ethyl 2-(2-bromo-4-pyridyl)acetate (1.00 g, 4.10 mmol) in a mixture of THF (5 mL), MeOH (10 mL) and water (5 mL) was added lithium hydroxide (294 mg, 12.3 mmol) and the reaction mixture was stirred at 20 °C for 10 mins. On completion, the reaction mixture was concentrated in vacuo to remove THF and MeOH and diluted with 10 mL water. The aqueous phase was acidified with 2N HCl solution until pH = 2. The mixture was filtered and the filter cake was dried in vacuo to give the title compound (850 mg, 90percent yield) as a white solid. LCMS: (ES⁺) m/z (M+H)⁺= 217.9, tR = 0.539.

Reference： [1] Patent: WO2018/106636, 2018, A1, . Location in patent: Paragraph 00242

2
[ 1387560-71-5 ]
[ 183483-29-6 ]

Reference： [1] Patent: US2012/184539, 2012, A1, . Location in patent: Page/Page column 32-33

3
[ 4926-28-7 ]
[ 183483-29-6 ]

Reference： [1] Patent: US2012/184539, 2012, A1,
[2] Patent: WO2018/106636, 2018, A1,

[ 183483-29-6 ] Synthesis Path-Downstream 1~27

1
[ 4926-28-7 ]
[ 183483-29-6 ]

Reference： [1]Patent: US2012/184539,2012,A1
[2]Patent: WO2018/106636,2018,A1

2
[ 1387560-71-5 ]
[ 183483-29-6 ]

Yield	Reaction Conditions	Operation in experiment
	With water; potassium carbonate; at 100℃; for 8.0h;	b) (2-Bromo-pyridin-4-yl)-acetic acidA suspension of 2-(2-bromo-pyridin-4-yl)-malonic acid diethyl ester (115 g, 316 mmol) and K2CO3 (125.23 g, 907.5 mmol) in water (500 ml) was heated at 100 C. for 8 h under constant stirring. Reaction mixture was cooled to rt and concentrated under reduced pressure to remove solvent completely. The solid residue was dissolved in minimum quantity of water (25 ml) and washed with 20% ethyl acetate in hexane to remove non polar impurities. The aqueous layer was seperated and cooled to 0 C. followed by adjusting pH 6 to 7 using aq. 6 N HCl. The precipitated solid was filtered using Buchner funnel, washed with ice cold water and dried under vacuum to furnish title compound as an off white solid. with sufficient purity. Yield: 60.0 g (76.3%). TLC (70% ethyl acetate in hexane) Rf=0.05; LCMS: RtH8=0.193; [M+1]+=215.9 and 217.9; HPLC RtH9=3.025 min (98%); 1H NMR (400 MHz, CDCl3): delta 12.71 (s, 1H), 8.33 (d, 1H), 7.61 (s, 1H), 7.37 (d, 1H), 3.71 (s, 3H).

Reference： [1]Patent: US2012/184539,2012,A1 .Location in patent: Page/Page column 32-33

3
[ 64-17-5 ]
[ 183483-29-6 ]
[ 1256337-24-2 ]

Yield	Reaction Conditions	Operation in experiment
88.5%		c) (2-Bromo-pyridin-4-yl)-acetic acid ethyl esterTo a solution of <strong>[183483-29-6](2-bromo-pyridin-4-yl)-acetic acid</strong> (60.0 g, 277.7 mmol) in ethanol (600 ml), conc: sulfuric acid (5.0 ml) was added at rt and the reaction mixture was heated at 90 C. for 9 h. Reaction mixture was cooled to rt and concentrated under reduced pressure to remove solvent completely. The residue obtained was cooled to 0 C. and pH was adjusted to 8 using 10% aqueous NaHCO3 solution. The resultant contents were worked up with ethyl acetate by washing with water, brine and dried over anhy. Na2SO4. Organic layer was concentrated under reduced pressure to obtain crude compound. Column chromtography purification of the crude compound using 15% ethyl acetate in hexane as eluent furnished title compound as a brown oil. Yield: 65.0 g (88.5%). TLC (30% ethyl acetate in hexane) Rf=0.39; LCMS: RtH7=0.824 [M+1]+=243.8 and 245.8; HPLC RtH9=3.759 min (69%); 1H NMR (300 MHz, CDCl3): delta 8.32 (t, 1H), 7.43 (s, 1H), 7.21-7.15 (M, 1H), 4.18 (q, 2H), 1.27 (t, 3H).

Reference： [1]Patent: US2012/184539,2012,A1 .Location in patent: Page/Page column 33

4
[ 183483-29-6 ]
[ 1387560-73-7 ]