[ CAS No. 3543-01-9 ] {[proInfo.proName]}

Name: 3543-01-9|5-Aminopyridin-3-ol|97%
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SKU: A197132
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Quality Control of [ 3543-01-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 3543-01-9 ]

Product Details of [ 3543-01-9 ]

CAS No. :	3543-01-9	MDL No. :	MFCD04114213
Formula :	C₅H₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YZSGZMGPVYECOU-UHFFFAOYSA-N
M.W :	110.11	Pubchem ID :	2762895
Synonyms :

Calculated chemistry of [ 3543-01-9 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	30.66
TPSA :	59.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.44
Log Po/w (XLOGP3) :	-0.18
Log Po/w (WLOGP) :	0.38
Log Po/w (MLOGP) :	-0.86
Log Po/w (SILICOS-IT) :	0.25
Consensus Log Po/w :	0.01

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.96
Solubility :	12.0 mg/ml ; 0.109 mol/l
Class :	Very soluble
Log S (Ali) :	-0.61
Solubility :	27.3 mg/ml ; 0.248 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.03
Solubility :	10.3 mg/ml ; 0.0938 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.4

Safety of [ 3543-01-9 ]

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 [ 3543-01-9 ]

* 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 [ 3543-01-9 ]
Downstream synthetic route of [ 3543-01-9 ]

[ 3543-01-9 ] Synthesis Path-Upstream 1~4

1
[ 74115-13-2 ]
[ 3543-01-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 928 - 931
[2] Roczniki Chemii, 1936, vol. 16, p. 136,137[3] Chem. Zentralbl., 1936, vol. 107, # II, p. 1167

2
[ 186593-25-9 ]
[ 3543-01-9 ]

Reference： [1] Patent: US6133253, 2000, A,

3
[ 13535-01-8 ]
[ 7732-18-5 ]
[ 3543-01-9 ]

Reference： [1] Chemische Berichte, 1936, vol. 69, p. 32,37

4
[ 3543-01-9 ]
[ 186593-26-0 ]

Yield	Reaction Conditions	Operation in experiment
47%	With dipotassium peroxodisulfate In concd sulfuric acid	132d. 3-hydroxy-5-nitropyridine Potassium persulfate (56.8 g 210 mmol) was ground into 31.5 mL of concd sulfuric acid, and the solution was added to a solution of the product of Example 132c (2.75 g 25 mmol) in concd sulfuric acid (27 mL). The mixture was allowed to stand for 72 hours, then was poured over ice and adjusted to pH 6 with concd NH₄ OH. The solution was extracted with EtOAc (4*100 mL), then the EtOAc extracts were dried (MgSO₄) and concentrated. The crude product was chromatographed (silica gel; CHCl₃ /MeOH, 99:1 to 9:1) to afford 1.65 g (47percent) of the title compound. ¹ H NMR (CDCl₃, 300 MHz) δ 8.81(d, J=3 Hz, 1H), 8.51 (d, H=3 Hz, 1H), 7.82 (dd, J=2.5 Hz, 1H). MS (DCI/NH₃) m/z 141 (M+H)⁺, 158 (M+NH₄)⁺.

Reference： [1] Patent: US6133253, 2000, A,

[ 3543-01-9 ] Synthesis Path-Downstream 1~29

1
[ 74115-13-2 ]
[ 3543-01-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 928 - 931
[2]Roczniki Chemii,1936,vol. 16,p. 136,137
Chemisches Zentralblatt,1936,vol. 107,p. 1167

3
[ 13535-01-8 ]
[ 7732-18-5 ]
[ 3543-01-9 ]

Reference： [1]Chemische Berichte,1936,vol. 69,p. 32,37

4
[ 3543-01-9 ]
[ 124-38-9 ]
5-amino-3-hydroxy-pyridine-2-carboxylic acid [ No CAS ]

Reference： [1]Acta Poloniae Pharmaceutica,1954,vol. 11,p. 71,72
Chem.Abstr.,1955,p. 8273

5
[ 3543-01-9 ]
BocNHCH₂CH₂OH or BocNHCH₂CH₂OTs [ No CAS ]
tert-butyl N-[2-[(5-amino-3-pyridyl)oxy]ethyl]carbamate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3321 - 3324

6
[ 3543-01-9 ]
5-(2-methylamino-ethoxy)-pyridin-3-ylamine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3321 - 3324

7
[ 186593-25-9 ]
[ 3543-01-9 ]

Yield	Reaction Conditions	Operation in experiment
4.5 g (53%)	In methanol; palladium-carbon;	132c. 3-amino-5-hydroxypyridine The product of Example 132b (15.47 g, 77.25 mmol) in MeOH (25 mL) was stirred under an atmosphere of H2 in the presence of 5% Pd/C (100 mg) for 48 hours. The mixture was filtered and concentrated, then the crude product was chromatographed (silica gel; CHCl3 /MeOH, 9:1) to afford 4.5 g (53%) of the title compound MS (DCI/NH3) m/z 111 (M+H)+, 128 (M+NH4)+. 1 H NMR (CDCl3, 300 MHz) delta 7.4 (d, J=3 Hz, 1H), 7.3 (d, J=2.5 Hz, 1H), 6.33 (dd, J=2.6 Hz, 1H).

Reference： [1]Patent: US6133253,2000,A

8
[ 3543-01-9 ]
[ 186593-26-0 ]

Yield	Reaction Conditions	Operation in experiment
1.65 g (47%)	With dipotassium peroxodisulfate; In concd sulfuric acid;	132d. 3-hydroxy-5-nitropyridine Potassium persulfate (56.8 g 210 mmol) was ground into 31.5 mL of concd sulfuric acid, and the solution was added to a solution of the product of Example 132c (2.75 g 25 mmol) in concd sulfuric acid (27 mL). The mixture was allowed to stand for 72 hours, then was poured over ice and adjusted to pH 6 with concd NH4 OH. The solution was extracted with EtOAc (4*100 mL), then the EtOAc extracts were dried (MgSO4) and concentrated. The crude product was chromatographed (silica gel; CHCl3 /MeOH, 99:1 to 9:1) to afford 1.65 g (47%) of the title compound. 1 H NMR (CDCl3, 300 MHz) delta 8.81(d, J=3 Hz, 1H), 8.51 (d, H=3 Hz, 1H), 7.82 (dd, J=2.5 Hz, 1H). MS (DCI/NH3) m/z 141 (M+H)+, 158 (M+NH4)+.

Reference： [1]Patent: US6133253,2000,A

9
[ 3543-01-9 ]
[ 1314895-84-5 ]