[ CAS No. 103766-25-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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2D 3D

Structure of 103766-25-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 103766-25-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 103766-25-2 ]

SDS Specification

Alternatived Products of [ 103766-25-2 ]

Product Details of [ 103766-25-2 ]

CAS No. :	103766-25-2	MDL No. :	MFCD08458352
Formula :	C₅H₄ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZPLQIPFOCGIIHV-UHFFFAOYSA-N
M.W :	145.54	Pubchem ID :	54679224
Synonyms :	Gimestat;CDHP;chlorodihydroxypyridine. Abbreviation: CDHP.;5-Chlorodihydropyrimidine	Chemical Name :	5-Chloro-4-hydroxypyridin-2(1H)-one

Calculated chemistry of [ 103766-25-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
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 :	34.1
TPSA :	53.09 ?2

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) :	-7.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.02
Log Po/w (XLOGP3) :	-0.08
Log Po/w (WLOGP) :	0.73
Log Po/w (MLOGP) :	0.24
Log Po/w (SILICOS-IT) :	1.73
Consensus Log Po/w :	0.73

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.19
Solubility :	9.5 mg/ml ; 0.0653 mol/l
Class :	Very soluble
Log S (Ali) :	-0.58
Solubility :	38.0 mg/ml ; 0.261 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.95
Solubility :	1.63 mg/ml ; 0.0112 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.61

Safety of [ 103766-25-2 ]

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

Application In Synthesis of [ 103766-25-2 ]

* 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 [ 103766-25-2 ]
Downstream synthetic route of [ 103766-25-2 ]

[ 103766-25-2 ] Synthesis Path-Upstream 1~1

1
[ 103766-25-2 ]
[ 405230-82-2 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1953, vol. 72, p. 285,291

[ 103766-25-2 ] Synthesis Path-Downstream 1~13

1
[ 103792-80-9 ]
[ 103766-25-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With acetic acid; sodium iodide; In acetonitrile; at 60℃; for 8h;	A mixture of compound 6 (8.0 g, 44 mmol), acetonitrile (100 mL), acetic acid (3 mL)and sodium iodide (13.2 g, 88 mmol) was heated for 8 h at 60 °C. Then the mixture was cooled to room temperature and poured into 10percent sodium thiosulfate solution (200 mL) to precipitate a colourless solid, which was recrystallised from water to give pure compound 2: Yield 5.6 g (86percent); m.p.272?273 °C (lit.7 273?274 °C); 1H NMR (400 MHz, DMSO-d6): delta 5.70(s, 1H), 7.51 (s, 1H), 11.29 (br, 2H) ; 13C NMR (100 MHz, DMSO-d6): delta163.5, 163.2, 134.6, 105.6, 98.7; LRMS (ESI) m/z (percent): 146 (100) [M (35Cl+ 1]+, 148 (30) [M (37Cl) + 1]+; HRMS (ESI) m/z calcd for C5H535ClNO2:[M + H]+: 146.0003; found: 146.0012; calcd for C5H537ClNO2: [M + H]+:147.9975; found: 147.9975.

Reference： [1]Journal of Chemical Research,2018,vol. 42,p. 33 - 34
[2]Recueil des Travaux Chimiques des Pays-Bas, 73<1954<704,708,

2
[ 856850-46-9 ]
[ 103766-25-2 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1953,vol. 72,p. 285,291

3
[ 103766-25-2 ]
[ 98-88-4 ]
[ 155131-51-4 ]
[ 103766-97-8 ]
[ 103815-09-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1498 - 1506

4
[ 103766-25-2 ]
[ 98-88-4 ]
[ 103815-09-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1498 - 1506

5
[ 103766-25-2 ]
[ 874-60-2 ]
4-Methyl-benzoic acid 5-chloro-2-oxo-1,2-dihydro-pyridin-4-yl ester [ No CAS ]
C₂₁H₁₆ClNO₄ [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1498 - 1506

6
[ 103766-25-2 ]
[ 874-60-2 ]
C₂₁H₁₆ClNO₄ [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1498 - 1506

7
[ 103766-25-2 ]
[ 75-36-5 ]
[ 103766-99-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1498 - 1506

8
[ 103766-25-2 ]
[ 999-97-3 ]
[ 103766-30-9 ]

Yield	Reaction Conditions	Operation in experiment
	for 6h;Reflux;	Reference Example 7 Synthesis of 3-{3-[4-hydroxy-5-chloro-2-pyridyloxycarbonyl]benzoyl}-1-ethoxymethyl-5-fluorouracil (Compound 8a) and 3-{3-[2-hydroxy-5-chloro-4-pyridyloxycarbonyl]benzoyl}-1-ethoxymethyl-5-fluorouracil (Compound 8b) 1-Ethoxymethyl-3-m-hydroxycarbonylbenzoyl-5-fluorouracil (3.46 g) was dissolved in methylene chloride (50 mL). Thionyl chloride (0.9 mL) and dimethylformamide (0.04 mL) were then added thereto. The resulting reaction product was refluxed for 2 hours, and the solvents were then evaporated. The residue was dissolved in methylene chloride (12 mL) to obtain a methylene chloride solution of acid chloride. After 2,4-dihydroxy-5-chloropyridine (1.5 g) was fluxed in hexamethyldisilazane (15 mL) for 6 hours, the solvent was evaporated, and the resulting residue was dissolved in methylene chloride (30 mL). The above methylene chloride solution of acid chloride was added dropwise thereto under ice cooling, and anhydrous stannic chloride (0.15 mL) was subsequently added thereto. The mixture was stirred at room temperature for 15 hours. After being neutralized with triethylamine, the residue obtained by evaporating the solvents was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane (1:2)) to obtain Compound 8a (2.15 g; yield: 45percent) and Compound 8b (496 mg; yield: 10percent). Compound 8a1H-NMR (DMSOd6, deltaPPM): 8.63 (1H, t, J = 1.6 Hz), 8.49 (2H, d, J = 8.2 Hz), 8.45 (1H, d, J = 6.7 Hz), 8.28 (1H, s), 7.86 (1H, t, J = 7.8 Hz), 6.91 (1H, s), 5.11 (2H, s), 3.58 (2H, q, J = 6.9 Hz), 1.11 (3H, t, J = 7.0 Hz)8.63 (1H, t, J = 1.6 Hz), 8.49 (2H, d, J = 8.2 Hz), 8.45 (1H, d, J = 6.7 Hz), 8.28 (1H, s), 7.86 (1H, t, J = 7.8 Hz), 6.91 (1H, s), 5.11 (2H, s), 3.58 (2H, q, J = 6.9 Hz), 1.11 (3H, t, J = 7.0 Hz)Compound 8b1H-NMR (DMSOd6, deltaPPM): 8.65 (1H, t, J = 3.3 Hz), 8.51 (2H, dt, J = 1.7, 7.7 Hz), 8.46 (1H, d, J = 6.6 Hz), 7.93 (1H, s), 7.89 (1H, t, J = 7.8 Hz), 6.63 (1H, s), 5.11 (2H, s), 3.58 (2H, q, J = 7.0 Hz), 1.12 (3H, t, J = 7.1 Hz)8.65 (1H, t, J = 3.3 Hz), 8.51 (2H, dt, J = 1.7, 7.7 Hz), 8.46 (1H, d, J = 6.6 Hz), 7.93 (1H, s), 7.89 (1H, t, J = 7.8 Hz), 6.63 (1H, s), 5.11 (2H, s), 3.58 (2H, q, J = 7.0 Hz), 1.12 (3H, t, J = 7.1 Hz)

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1498 - 1506
[2]Patent: EP2495243,2012,A1 .Location in patent: Page/Page column 15

9
[ 147619-40-7 ]
[ 103766-25-2 ]

Yield	Reaction Conditions	Operation in experiment
83.2%	With hydrogen bromide;Reflux;	Add in 250ml three-necked flask5-chloro-4-methoxy-3-cyano-2- (1H) pyridone,48percent hydrobromic acid 150 ml,Heating reflux reaction for about 20-24 hours,Stop the reaction, this time the system is dark red solution.The reaction solution was concentrated at 90-95 ° C under reduced pressure to dryness,Add 200ml purified water beating,After stirring for 1 hour, the filtrate was filtered.Filter cake in 55-60 blast drying,Brown solid,That gimeracil,Weight 6.57 g, yield 83.2percentPurity of 99.91percent (see Figure 1),

Reference： [1]Heterocycles,1993,vol. 36,p. 145 - 148
[2]Patent: CN104592102,2017,B .Location in patent: Paragraph 0025; 0041; 0042; 0043; 0044; 0045

10
[ 103766-25-2 ]
Acetic acid 5-chloro-4-oxo-1,4-dihydro-pyridin-2-yl ester [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1498 - 1506

11
[ 103766-25-2 ]
5-chloro-4-hydroxyl-1-methoxymethyl-2-pyridone [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1498 - 1506

12
[ 103766-25-2 ]
[ 103815-27-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1498 - 1506

13
[ 21642-98-8 ]
[ 103766-25-2 ]

Yield	Reaction Conditions	Operation in experiment
93.2%	With hydrogen bromide; for 18.0h;Reflux;	A solution of 6.0 g (0.033 mol) of 3-cyano-4-methoxy-5-chloro 2- (1H)And 163percent of the mass percentage of 48percentHydrobromic acid solution into 500 ml three-necked flask,Heated to reflux for 18 h,Cooling to 50 ± 2 ,Concentrated under reduced pressure mass percent concentration of 48percent hydrobromic acid solution,Add 60ml of deionized water to stir until the residual solid was dissolved,Plus 0.6g activated carbon,Stirring at 80 ° C for 15 min,Worry,Filtrate insulation 50 ± 3 ,Start dropping 40percent sodium hydroxide solution to adjust the pH to pH = 4 ± 0.5,After adjusting the temperature to 10-15 ,Stir for 3 hours,Filtration of 12 ml of water.Wet goods at 80 under normal pressure drying 14h,To give 4.41g gimeracil white powder,Yield 93.2percentTheoretical yield 4.73g,Purity greater than 99.5percentIndividual impurities are less than 0.1percent.

Reference： [1]Patent: CN106316934,2017,A .Location in patent: Paragraph 0023; 0024; 0026; 0027; 0028

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Appel Reaction ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chugaev Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Fischer Indole Synthesis ? General Reactivity ? Grignard Reaction ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Jones Oxidation ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Martin's Sulfurane Dehydrating Reagent ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Alcohols ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Alcohols ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Ritter Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Swern Oxidation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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H401	Toxic to aquatic life
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 103766-25-2 ] {[proInfo.proName]}

Quality Control of [ 103766-25-2 ]

Related Doc. of [ 103766-25-2 ]

Product Details of [ 103766-25-2 ]

Calculated chemistry of [ 103766-25-2 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 103766-25-2 ]

Application In Synthesis of [ 103766-25-2 ]

[ 103766-25-2 ] Synthesis Path-Upstream 1~1

[ 103766-25-2 ] Synthesis Path-Downstream 1~13

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