[ CAS No. 85633-41-6 ]

Name: 85633-41-6|2-Hydroxy-5-(pyridin-3-yl)benzaldehyde|95%
Brand: Ambeed
SKU: A565805
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Quality Control of [ 85633-41-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 85633-41-6 ]

Product Details of [ 85633-41-6 ]

CAS No. :	85633-41-6	MDL No. :	MFCD11877750
Formula :	C₁₂H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KVOMYFGYEIPWGE-UHFFFAOYSA-N
M.W :	199.21	Pubchem ID :	13365800
Synonyms :

Calculated chemistry of [ 85633-41-6 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	57.08
TPSA :	50.19 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) :	-6.0 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.36
Log Po/w (XLOGP3) :	2.14
Log Po/w (WLOGP) :	2.27
Log Po/w (MLOGP) :	0.79
Log Po/w (SILICOS-IT) :	2.66
Consensus Log Po/w :	1.84

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.88
Solubility :	0.261 mg/ml ; 0.00131 mol/l
Class :	Soluble
Log S (Ali) :	-2.83
Solubility :	0.297 mg/ml ; 0.00149 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.92
Solubility :	0.0239 mg/ml ; 0.00012 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.89

Safety of [ 85633-41-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:
Hazard Statements:	H302-H312-H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 85633-41-6 ]

* 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.

Downstream synthetic route of [ 85633-41-6 ]

[ 85633-41-6 ] Synthesis Path-Downstream 1~21

1
[ 68223-13-2 ]
[ 100-97-0 ]
[ 85633-41-6 ]

Yield	Reaction Conditions	Operation in experiment
	With water; trifluoroacetic acid 1.) 80 deg C, 4 h, 2.) RT, 20 min; Yield given. Multistep reaction;

Reference： [1]Johnson; Nidy; Aiken; Crittenden; Gorman [Journal of medicinal chemistry, 1986, vol. 29, # 8, p. 1461 - 1468]

2
[ 685-87-0 ]
[ 85633-41-6 ]
[ 85633-42-7 ]

Yield	Reaction Conditions	Operation in experiment
61%	With perhydrodibenzo-18-crown-6; sodium hydride In toluene for 48h; Ambient temperature;

Reference： [1]Johnson; Nidy; Aiken; Crittenden; Gorman [Journal of medicinal chemistry, 1986, vol. 29, # 8, p. 1461 - 1468]

3
[ 82261-42-5 ]
[ 85633-41-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaNO₂, conc H₂SO₄, 2.) H₂O / 1.) water, 1 h, 2.) 160 deg C, 10 min 2: 1.) trifluoroacetic acid, 2.) water / 1.) 80 deg C, 4 h, 2.) RT, 20 min

Reference： [1]Johnson; Nidy; Aiken; Crittenden; Gorman [Journal of medicinal chemistry, 1986, vol. 29, # 8, p. 1461 - 1468]

4
[ 85633-41-6 ]
[ 85633-43-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 61 percent / NaH, dicyclohexyl-18-crown-6 / toluene / 48 h / Ambient temperature 2: 0.1N aq. NaOH / methanol / 1.5 h

Reference： [1]Johnson; Nidy; Aiken; Crittenden; Gorman [Journal of medicinal chemistry, 1986, vol. 29, # 8, p. 1461 - 1468]

5
[ 85633-41-6 ]
3-bromo-2-hydroxy-5-pyridine-3-yl-benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With mono(N,N,N-trimethylbenzenaminium) tribromide In methanol; dichloromethane at 20℃; for 2h;	3; 20.20-a Scheme 3; Preparation of 5-(pyridin-3-yl)benzofuran derivatives; Preparation of 4-[amino-(5-pyridin-3-yl-benzofuran-2-yl)-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile compounds; Example 20; Preparation of 4-[amino-[7-(3-fluoro-phenyl)-5-pyridin-3-yl-benzofuran-2-yl]-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile; 20-a) Preparation of 3-bromo-2-hydroxy-5-pyridine-3-yl- benzaldehyde To a solution of 2-hydroxy-5-pyridine-3-yl-benzaldehyde (20.0 g, 100 mmol) in DCM/MeOH (500/200 ml) was added benzyltrimethylammonium tribrommide (39.1 g, 100 mmol) at room temperature. After stirring at room temperature for 2h, the mixture was quenched with water. The mixture was extracted with DCM (* 2). The organic layers were combined, dried over MgS04, filtered and evaporated in vacuo to give 25.0 g of 3-bromo-2-hydroxy-5-pyridine-3-yl-benzaldehyde as a light yellow solid (crude). LCMS (condition B) m/z 278 [M+H] +, retention time 2.54 minutes ; 1H-NMR (CDCl3) δ 11.65 (s, 1H), 9.96 (s, 1H), 8.83 (d, J= 1.7 Hz, 1H), 8.64 (dd, J= 1.7, 4.8 Hz, 1H), 8.03 (d, J= 2.3 Hz, 1H), 7.86 (ddd, J= 1.7, 2.3, 7.9 Hz, 1H), 7.76 (d, J= 2.3 Hz, 1H), 7.41 (dd, J= 4.8, 7.9 Hz, 1H).

Reference： [1]Current Patent Assignee: Chugai Pharmaceutical (in: Roche); ROCHE HOLDING AG - WO2004/37816, 2004, A1 Location in patent: Page 27; 46-47

6
thiosemi-carbazide [ No CAS ]
[ 1692-25-7 ]
[ 85633-41-6 ]
[ 1761-61-1 ]
5-(3-Pyridyl)salicylaldehyde thiosemicarbazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%		31 5-(3-Pyridyl)salicylaldehyde thiosemicarbazone Example 31 5-(3-Pyridyl)salicylaldehyde thiosemicarbazone The 5-(3-pyridyl)salicylaldehyde_was obtained in a yield of 40% according to General Procedure B using 3-pyridyl boronic acid and 5-bromo salicylaldehyde as starting matrial. The title compound is made from 5-(3-pyridyl)salicylaldehyde and thiosemi-carbazide, using General Procedure A. 1H NMR (d6-DMSO) δ7.01 (d, 1H), 7.45 (t, 1H), 7.53 (d, 1H), 8.08 (d, 1H), 8.18 (d, 1H), 8.22 (s, 1H), 8.32 (s, 1H), 8.42 (s, 1H), 8.53 (s, 1H), 8.95 (s, 1H), 10.25 (s, 1H), 11.42 (s, 1H). MS 273 (M+H), C13H12N4OS.

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - US2003/187007, 2003, A1

Yield	Reaction Conditions	Operation in experiment
33%
		23 2-Formyl-4-(3-pyridyl)phenol An additional recrystallization from acetone-hexane gives an analytical sample of the titled product as very pale yellow crystals with a melting point of 123°-124° C. The IR (Nujol) spectrum reveals peaks at 2567, 1674, 1608, 1308, 1290, 1259, 1241, 1196, 1166, 1117, 1034, and 810 cm-1. The NMR (CDCl3, δ) spectrum reveals peaks at 10.03, 8.86, 8.64, and 7.95-7.05.

8
[ 141-97-9 ]
[ 85633-41-6 ]
[ 1208985-30-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With piperidine In acetonitrile at 20℃; for 4h;

Reference： [1]Location in patent: experimental part Raju, B. China; Tiwari, Ashok K.; Kumar, J. Ashok; Ali, A. Zehra; Agawane, Sachin B.; Saidachary; Madhusudana [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 1, p. 358 - 365]

9
[ 1692-25-7 ]
[ 1761-61-1 ]
[ 85633-41-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; toluene at 20 - 80℃; for 2.3h; Inert atmosphere;

10
[ 10025-99-7 ]
[ 85633-41-6 ]
[ 95-55-6 ]
[ 1228301-89-0 ]