[ CAS No. 109205-68-7 ] {[proInfo.proName]}

Name: 109205-68-7|5-(Hydroxymethyl)pyridin-2(1H)-one|98%
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Quality Control of [ 109205-68-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 109205-68-7 ]

Product Details of [ 109205-68-7 ]

CAS No. :	109205-68-7	MDL No. :	MFCD09839753
Formula :	C₆H₇NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JLPOBAADYFDVAV-UHFFFAOYSA-N
M.W :	125.13	Pubchem ID :	12018576
Synonyms :

Calculated chemistry of [ 109205-68-7 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	33.19
TPSA :	53.09 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) :	-7.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.09
Log Po/w (XLOGP3) :	-1.13
Log Po/w (WLOGP) :	-0.28
Log Po/w (MLOGP) :	-0.29
Log Po/w (SILICOS-IT) :	1.36
Consensus Log Po/w :	0.15

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.33
Solubility :	58.4 mg/ml ; 0.466 mol/l
Class :	Very soluble
Log S (Ali) :	0.51
Solubility :	402.0 mg/ml ; 3.21 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-1.72
Solubility :	2.39 mg/ml ; 0.0191 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.32

Safety of [ 109205-68-7 ]

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

Application In Synthesis of [ 109205-68-7 ]

* 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 [ 109205-68-7 ]
Downstream synthetic route of [ 109205-68-7 ]

[ 109205-68-7 ] Synthesis Path-Upstream 1~5

1
[ 109205-68-7 ]
[ 70258-18-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With phosphorus pentachloride In chloroform; water; trichlorophosphate	EXAMPLE 4 Production of 2-chloro-5-chloromethyl-pyridine A solution of 2.5 g (20 mmol) of 2-hydroxy-5-hydroxymethylpyridine and 4.16 g of phosphorus pentachloride in 10 ml of phosphoryl chloride was stirred for 6 hours at 105° C. After cooling, 50 ml of chloroform was added, the excess chlorination reagent being hydrolyzed by careful addition of water. The organic phase was washed with NaHCO₃ solution, dried on NaSO₄ and concentrated by evaporation. The distillation of the oily residue at 16 mm and 120° C. yielded 3.08 g of 2-chloro-5-chloromethyl-pyridine as a colorless oil that solidified during the cooling. The latter corresponds to a yield of 95 percent relative to the 2-hydroxy-5-hydroxymethyl-pyridine. Further data concerning the product was: ¹ H-NMR: (CDCl₃, 300 MHz) δ in ppm: 8.28 (d, J=2.3 Hz, 1H, H-6); 7.72 (dd, J=8.2 Hz, J=2.3 Hz, H-4); 7.34 (d, J=8.2 Hz, 1H, H-3); 4.58 (s, CH₂ Cl, 2H).

Reference： [1] Patent: US6022974, 2000, A,

2
[ 109205-68-7 ]
[ 70258-18-3 ]

Reference： [1] Patent: US4958025, 1990, A,

3
[ 106984-91-2 ]
[ 109205-68-7 ]

Reference： [1] Patent: US4958025, 1990, A,

4
[ 66171-50-4 ]
[ 109205-68-7 ]

Reference： [1] Patent: WO2011/12622, 2011, A1, . Location in patent: Page/Page column 110

5
[ 66171-50-4 ]
[ 109205-68-7 ]

Reference： [1] Patent: US2002/49330, 2002, A1,

[ 109205-68-7 ] Synthesis Path-Downstream 1~13

1
[ 66171-50-4 ]
[ 109205-68-7 ]

Yield	Reaction Conditions	Operation in experiment
	With LiAlH4; In tetrahydrofuran; ethanol; water; ethyl acetate;	To a suspension of LiAlH4 (0.32 gm, 8.4 mmol) in 80 ml THF was added, slowly and dropwise, a solution of methyl 6-hydroxynicotinate (1.15 gm, 7.5 mmol) in 400 ml THF. The mixture was stirred at room temperature for 1.5 hours and then refluxed for 10 minutes. The mixture was then cooled and the reaction quenched with 3.0 ml of ethyl acetate and 1.5 ml of water. The solvents were removed and the residue was taken up in 40 ml of refluxing ethanol. The solution was filtered through celite and ethanol was evaporated in vacuo. The product was purified by silica gel chromatography using ethyl acetate/methanol (2:1) as the eluent. The product 5-hydroxymethyl-2-pyridone was crystallized from ethanol/ethyl acetate and the yield of the reaction was 0.65 gm (80%). HRMS: m/e, M+ found 125.0468, 100%. Calc. for C6H7NO2: 125.0477, -6 ppm. 1H NMR (d6-DMSO): 11.47 (broad, 1H, NH), 7.39 (dd, J3-4=9.5 Hz, J4-6=2.5 Hz, 1H, C(4) H), 7.23 (d, J4-6=2.5 Hz, 1H, C(6)H), 6.27 (d, J3-4=9.5 Hz, 1H, C(3)H), 5.10 (t, J=5.5 Hz, 1H, CH2OH), 4.17 (d, J=5.5 Hz, 2H, CH2OH). IR (cm-1): 3271 (m, broad), upsilon(O-H); 3124 (m, broad), upsilon(N-H); 3011(m), upsilon(C-H); 1661(vs), upsilon(C=O).

Reference： [1]Patent: US2002/49330,2002,A1

2
[ 109205-68-7 ]
5-bromomethyl-2-pyridone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide;	To <strong>[109205-68-7]5-hydroxymethyl-2-pyridone</strong> (114.9 mg, 0.9 mmol) was added 3.0 ml of 48% hydrobromic acid. The mixture was heated at 100 C. for 20 minutes. The excess hydrobromic acid was then evaporated in vacuo to give the corresponding 5-bromomethyl-2-pyridone. This compound was used without purification. HRMS: m/e, M+ found; 186.9626, 7.4% Calc. for C6H6BrNO: 186.9633, -3.9 ppm. The 5-bromomethyl-2-pyridone was taken up in diethyl amine and the solution refluxed for 1 hour.

Reference： [1]Patent: US2002/49330,2002,A1

3
[ 109205-68-7 ]
[ 70258-18-3 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride; sodium carbonate; trichlorophosphate; In ethyl acetate;	STR18 2.0 g (0.016 mol) of 5-hydroxymethyl-2-pyridinone are added to a mixture of 6.7 g (0.032 mol) of phosphorus pentachloride and 2.5 g (0.016 mol) of phosphorus oxychloride, the mixture is stirred at reflux temperature for 7 hours, cooled and taken up in ethyl acetate, ice water is then added, the mixture is rendered neutral using sodium carbonate, the organic phase is separated off and dried over magnesium sulphate, and the solvent is removed under reduced pressure. The residue may be purified by distillation. 2.5 g (96% of theory) of 2-chloro-5-chloromethylpyridine of boiling point 70 C.-80 C. at 1 mbar are obtained.

Reference： [1]Patent: US4958025,1990,A

4
[ 106984-91-2 ]
[ 109205-68-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;aluminum nickel; In ethanol; ethyl acetate;	STR17 2 g of Raney nickel are added to 10.0 g (0.081 mol) of 2-pyridinone-5-aldehyde in 200 ml of ethanol, and the mixture is subsequently hydrogenated for 4 hours at 80 C. and 30 bar hydrogen pressure. For working up, the catalyst is filtered off, the filtrate is concentrated, and the solid which remains is purified by stirring with ethyl acetate, filtering off with suction and dried. 7 g (78% of theory) of 5-hydroxymethyl-2-pyridinone of melting point 130 C. are obtained.

Reference： [1]Patent: US4958025,1990,A

5
[ 66171-50-4 ]
[ 109205-68-7 ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of methyl 6-oxo-1 ,6-dihydro-3-pyridinecarboxylate (400 mg; Fluorochem) in THF (7 mL) was added dropwise 2M lithium borohydride in THF (6.53 mL) and the reaction mixture was heated at 55 0C under an atmosphere of argon for 5 hr. The reaction mixture was allowed to cool to RT and MeOH (4 mL) and water (1 mL) were added carefully. The mixture was stirred at room temperature for 20 min and then concentrated under reduced pressure. The crude product was purified by column chromatography, Biotage SP4, 25+M column, 0 - 30% MeOH / DCM. The fractions containing product were combined and concentrated under reduced pressure to give the title compound (68 mg) as a white solid, m/z [M+H]+: 125.9. Retention time 0.24 min (LC/MS method 3).

Reference： [1]Patent: WO2011/12622,2011,A1 .Location in patent: Page/Page column 110

6
[ 109205-68-7 ]
C₁₃H₁₂BrNO₅S [ No CAS ]
C₁₇H₁₃BrN₂O₅S [ No CAS ]

Reference： [1]Patent: WO2017/176812,2017,A1

7
[ 109205-68-7 ]
C₁₃H₁₂BrNO₅S [ No CAS ]
C₁₉H₁₇BrN₂O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 30℃;	To a solution of E2 (50 rng, 0.14 mrnol), 5(Iiydroxymethyi)pyridim2(1H}-one(20 mg, 0.16 mmol), and PPh3 (42 mg, 0.16 mmol) in TI-IF (2 mL) is added DIAD (54 mg,0.27 mmol) at room temperature. After stirring at 30 C overnight, the mixture isconcentrated. triturated with F:tOH (3 rnL), and collected by filtration to give 260 as a whitesolid (23 rng, 36% yield). (MS: [M±HI 481.1)

Reference： [1]Patent: WO2017/176812,2017,A1 .Location in patent: Paragraph 0562

8
[ 18617-50-0 ]
[ 109205-68-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With lithium aluminium tetrahydride; at 20℃; for 3.5h;Reflux;	To a stirred solution of 6-hydroxynicotinic acid (10 g, 72 mmol) in absolute ethanol (500 mL) was added sulfuric acid (4 mL) at room temperature. The mixture was heated to reflux for 48 h. After cooling down to room temperature, water (50 mL) was added and the reaction mixture was neutralised to pH= 6-7 by portionwise addition of sodiumhydrogen carbonate (caution: gas evolution). The mixture was evaporated under reduced pressure (most of ethanol was removed), and the residue was extracted with ethyl acetate (3 × 50 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated under reduced pressure leading to the pure <strong>[18617-50-0]ethyl 6-hydroxynicotinate</strong>[30] (10 g, 86percent). 1H NMR (400 MHz, CDCl3): delta 13.07 (s,1H), 8.14 (s, 1H), 7.94 (d, 1H, J = 9.9 Hz), 6.51 (d, 1H, J = 9.4 Hz),4.25 (q, 2H, J =7.1 Hz), 1.29 ppm.To a stirred solution of lithium aluminium hydride (1.4 g, 37 mmol,1.2 equiv.) in anhydrous THF (20 mL) at room temperature was added dropwise over 1 h a solution of <strong>[18617-50-0]ethyl 6-hydroxynicotinate</strong> (5.1 g,31 mmol) in anhydrous THF (150 mL) at the same temperature. The mixture was stirred at room temperature for 2 h and then heated toreflux for 30 min. The reaction mixture was cooled down to 0 °C andquenched with ethyl acetate (12 mL) and water (6 mL). The solventswere removed and the residue was taken up in refluxing ethanol(200 mL). The solution was filtered through Celite® and ethanol was evaporated under reduced pressure. The crude material was purified bycolumn chromatography on silica gel with ethyl acetate/methanol(75:25) as eluent to afford the pure title compound 12 (2.3 g, 60percent). 1HNMR (400 MHz, DMSO-d6): delta 11.56 (s, 1H), 7.43 (dd, 1H, J = 9.1 Hz,J = 2.5 Hz), 7.25 (d, 1H, J =2.5 Hz), 6.30 (d, 1H, J= 9.1 Hz), 5.22 (t,1H, J= 5.6 Hz), 4.20 (d, 2H, J = 5.6 Hz) ppm. 13C NMR (101 MHz,DMSO-d6): delta 162.6, 142.0, 133.0, 120.1, 119.6, 60.1 ppm. HRMS (ESI)calcd for C6H8NO2 [M + H]+: 126.056. Found: 126.055.

Reference： [1]Journal of Fluorine Chemistry,2017,vol. 203,p. 155 - 165

9
[ 109205-68-7 ]
[ 1211584-92-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 2: potassium hydroxide / water; acetonitrile / 0.5 h / 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 4: thionyl chloride / toluene / 1 h / 20 °C

Reference： [1]Landelle, Gregory; Schmitt, Etienne; Panossian, Armen; Vors, Jean-Pierre; Pazenok, Sergiy; Jeschke, Peter; Gutbrod, Oliver; Leroux, Frédéric R. [Journal of Fluorine Chemistry, 2017, vol. 203, p. 155 - 165]

10
[ 109205-68-7 ]
2-chloro-6-(dimethylamino)-4-ethylpyridine-3,5-dicarbonitrile [ No CAS ]
2-(dimethylamino)-4-ethyl-6-(((6-oxo-1,6-dihydropyridin-3-yl)methyl)thio)pyridine-3,5-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%		48% Hydrobromic acid (3 mL, 26.5 ymethyl)pyridin-2(1H)- one (400 mg, 3.20 mmol) at 0 C and then heated at 110 C for 16 hours. The mixture was concentrated to afford a crude black liquid (400 mg). To a solution of 2-chloro-6- (dimethylamino)-4-ethylpyridine-3,5-dicarbonitrile (synthesis described in example 3, step 3, 200 mg, 0.823 mmol) in N,N-dimethylformamide (10 mL) was added potassium thioacetate (188 mg, 1.646 mmol) and the reaction mixture was stirred at room temperature for 2 hours. After 2 hours the reaction mixture was cooled to 0 C, then potassium carbonate (228 mg, 1.646 mmol) and the crude black liquid (400 mg) were added and the mixture was stirred at room temperature for 1 hour. The reaction mass was diluted with ethyl acetate (100 mL) and washed with aqueous HCl solution (1 N, 2 x 100 mL). The organic layer was dried over anhydrous Na2SO4, filtered and the filtrate evaporated under vacuum to give crude compound. The crude compound was purified by silica gel column chromatography (100-200 mesh, eluted with 3-4% methanol in DCM) to afford 2-(dimethylamino)-4-ethyl-6- (((6-oxo-1,6-dihydropyridin-3-yl)methyl)thio)pyridine-3,5-dicarbonitrile (115 mg, 41%) as a brown solid. LCMS m/z = 340.1 [M+H]+.1H NMR (400 MHz, DMSO-d6) delta ppm 11.5 (s, 1H), 7.4 (dd, J = 2.4 Hz, J = 2.8 Hz, 1H), 7.4 (s, 1H), 6.2 (d, J = 9.2 Hz, 1H), 4.2 (s, 2H), 3.2- 3.4 (2s, 6H), 2.7 (q, J = 7.6 Hz, 2H), 1.2 (t, J = 7.6 Hz, 3H).

Reference： [1]Patent: WO2017/216726,2017,A1 .Location in patent: Page/Page column 627

11
[ 109205-68-7 ]
[ 1263413-99-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With hydrogen bromide; In water; at 110℃; for 3h;	5-(Hydroxymethyl)-1,2-dihydropyridin-2-one (1.0 g, 7.991 mmol, 1.0 eq) in aqueous HBr (48%), was stirred at 110 C. for 3 h. After completion of the reaction (monitored by TLC, TLC system 5% MeOH in DCM, Rf-0.1), the solvent was removed under reduced pressure to get the crude product. The crude product was azeotroped with toluene to get 5-(bromomethyl)pyridin-2(1H)-one hydrobromide (2.0 g, 93%).

Reference： [1]Patent: US2019/185455,2019,A1 .Location in patent: Paragraph 0360-0361

12
[ 109205-68-7 ]
5-((5-iodo-1H-indazol-1-yl)methyl)pyridin-2(1H)-one [ No CAS ]

Reference： [1]Patent: US2019/185455,2019,A1

13
[ 109205-68-7 ]
5-((5-iodo-1H-indazol-1-yl)methyl)-1-methylpyridin-2(1H)-one [ No CAS ]

Reference： [1]Patent: US2019/185455,2019,A1

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P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 109205-68-7 ] {[proInfo.proName]}

Quality Control of [ 109205-68-7 ]

Related Doc. of [ 109205-68-7 ]

Product Details of [ 109205-68-7 ]

Calculated chemistry of [ 109205-68-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 109205-68-7 ]

Application In Synthesis of [ 109205-68-7 ]

[ 109205-68-7 ] Synthesis Path-Upstream 1~5

[ 109205-68-7 ] Synthesis Path-Downstream 1~13

Related Functional Groups of [ 109205-68-7 ]

Alcohols

Amides

Related Parent Nucleus of [ 109205-68-7 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 109205-68-7 ]

Related Parent Nucleus of
[ 109205-68-7 ]