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2-(Dimethylaminomethyl)-3-hydroxypyridine

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Products Intro: Product Name:2-((Dimethylamino)methyl)pyridin-3-ol
CAS:2168-13-0
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CAS:2168-13-0
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CAS:2168-13-0
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CAS:2168-13-0
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Products Intro: Product Name:2-[(dimethylamino)methyl]pyridin-3-ol
CAS:2168-13-0

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2-(Dimethylaminomethyl)-3-hydroxypyridine Basic information
Product Name:2-(Dimethylaminomethyl)-3-hydroxypyridine
Synonyms:2-(DIMETHYLAMINOMETHYL)-3-HYDROXYPYRIDINE;2-DIMETHYLAMINOMETHYL-3-PYRIDINOL;2(-DIMETHYLAMINOMETHYL)-3-PYRIDOL;3-Pyridinol, 2-[(dimethylamino)methyl]-;2-[(dimethylamino)methyl]pyridin-3-ol;3-Hydroxy-2-(dimethylaminomethyl)-pyridine;2-(DIMETHYLAMINOMETHYL)-3-HYDROXYPYRIDINE 97%;2-(Dimethylaminomethyl)pyridine-3-ol
CAS:2168-13-0
MF:C8H12N2O
MW:152.19
EINECS:218-510-9
Product Categories:
Mol File:2168-13-0.mol
2-(Dimethylaminomethyl)-3-hydroxypyridine Structure
2-(Dimethylaminomethyl)-3-hydroxypyridine Chemical Properties
Melting point 56-59 °C(lit.)
Boiling point 98 °C4 mm Hg(lit.)
density 1.0996 (rough estimate)
refractive index 1.4940 (estimate)
storage temp. Storage temp. 2-8°C
form solid
pka8.79±0.10(Predicted)
AppearanceOff-white to light yellow Solid
InChI1S/C8H12N2O/c1-10(2)6-7-8(11)4-3-5-9-7/h3-5,11H,6H2,1-2H3
InChIKeyNUMYETXZBQVFDX-UHFFFAOYSA-N
SMILESCN(C)Cc1ncccc1O
CAS DataBase Reference2168-13-0
NIST Chemistry Reference2-(Dimethylaminomethyl)-3-hydroxypyridine(2168-13-0)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37/39
WGK Germany 3
HS Code 2933399990
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
2-(Dimethylaminomethyl)-3-hydroxypyridine Usage And Synthesis
Chemical Propertieswhite to beige crystalline powder
Synthesis Reference(s)Journal of the American Chemical Society, 71, p. 2969, 1949 DOI: 10.1021/ja01177a007
Synthesis
3-Hydroxypyridine

109-00-2

Formaldehyde

50-00-0

Dimethylamine

124-40-3

2-(Dimethylaminomethyl)-3-hydroxypyridine

2168-13-0

To a solution of 3-hydroxypyridine (200 g, 2.10 mol) in water (500 mL) was sequentially added 50% aqueous dimethylamine (228 g) and 36% aqueous formaldehyde (210 g), and the reaction mixture was stirred at room temperature, then heated up to 50 °C and kept for 4 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the precipitated crystals were collected by filtration to afford the target product 2-(dimethylaminomethyl)-3-hydroxypyridine (207 g, 65% yield). The structure of the product was confirmed by 1H-NMR (CDCl3): δ 2.38 (6H, s), 3.86 (2H, s), 7.01-7.18 (2H, m), 8.00 (1H, t, J = 3.2 Hz), and a hidden proton signal.

References[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 16, p. 7034 - 7042
[2] Patent: EP2100895, 2009, A1. Location in patent: Page/Page column 74-75
[3] Journal of the American Chemical Society, 1949, vol. 71, p. 2968,2971
2-(Dimethylaminomethyl)-3-hydroxypyridine Preparation Products And Raw materials
Raw materials3-Hydroxypyridine-->Formaldehyde-->Dimethylamine
Tag:2-(Dimethylaminomethyl)-3-hydroxypyridine(2168-13-0) Related Product Information
Dimethyl sulfoxide 2-Chloro-3-hydroxypyridine Poly(dimethylsiloxane) 2,6-Lutidine 3-Hydroxypyridine N,N-Dimethylformamide 2-(1-Piperidinylmethyl)-3-pyridinol 2-(Dimethylaminomethyl)-3-hydroxypyridine 3-[(4,6-DIMETHYLPYRIMIDIN-2-YL)OXY]-N-METHYL-N-PHENYL-2-PYRIDINEMETHANAMINE 3-[(4,6-DIMETHOXYPYRIMIDIN-2-YL)OXY]-N-(4-METHOXYPHENYL)-N-METHYL-2-PYRIDINEMETHANAMINE (2S,4R)-1-[[3-[(4,6-DIMETHOXYPYRIMIDIN-2-YL)OXY]PYRIDIN-2-YL]CARBONYL]-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID, ETHYL ESTER 1-BENZYL-5-OXO-3-PYRROLIDINECARBOXYLIC ACID 3-[(4,6-DIMETHOXYPYRIMIDIN-2-YL)OXY]-N-METHYL-N-PHENYL-2-PYRIDINEMETHANAMINE (4S)-3-[[3-[(4,6-DIMETHOXYPYRIMIDIN-2-YL)OXY]PYRIDIN-2-YL]CARBONYL]THIAZOLIDINE-4-CARBOXYLIC ACID, METHYL ESTER 2-((Isopentylmethylamino)methyl)-3-pyridinol dimethylcarbamate oxalate 3-Pyridinol, 2-(1-piperidinylmethyl)-, dimethylcarbamate, oxalate aminostigmine 1-(3,4-DIMETHOXY-PYRIDIN-2-YLMETHYL)-PIPERAZINE