(2,6-Dichloro-3-pyridinyl)methanol

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(2,6-Dichloro-3-pyridinyl)methanol Basic information
Product Name:(2,6-Dichloro-3-pyridinyl)methanol
Synonyms:3-PyridineMethanol, 2,6-dichloro-;(2,6-Dichloropyridin-3-yl);(2,6-Dichloro-3-pyridinyl)methanol;2,6-Dichloro-3-(hydroxyme...;2,6-Dichloro-3-(hydroxyMethyl)pyridine;2,6-Dichloro-3-pyridineMethanol, 95%;2,6-Dichloropyridine-3-methanol;2,6-Dichloro-3-pyridinemethanol,95%
CAS:55304-90-0
MF:C6H5Cl2NO
MW:178.02
EINECS:
Product Categories:
Mol File:55304-90-0.mol
(2,6-Dichloro-3-pyridinyl)methanol Structure
(2,6-Dichloro-3-pyridinyl)methanol Chemical Properties
Melting point 67-69°
Boiling point 311.6±37.0 °C(Predicted)
density 1.478±0.06 g/cm3(Predicted)
storage temp. Inert atmosphere,Room Temperature
form solid
pka12+-.0.10(Predicted)
AppearanceWhite to off-white Solid
InChIInChI=1S/C6H5Cl2NO/c7-5-2-1-4(3-10)6(8)9-5/h1-2,10H,3H2
InChIKeyFWEVVZQDRPWAND-UHFFFAOYSA-N
SMILESC1(Cl)=NC(Cl)=CC=C1CO
CAS DataBase Reference55304-90-0
Safety Information
WGK Germany WGK 3
HazardClass IRRITANT
HS Code 2933399990
Storage Class11 - Combustible Solids
MSDS Information
(2,6-Dichloro-3-pyridinyl)methanol Usage And Synthesis
Synthesis
2,6-Dichloronicotinic acid

38496-18-3

(2,6-Dichloro-3-pyridinyl)methanol

55304-90-0

The general procedure for the synthesis of 2,6-dichloro-3-hydroxymethylpyridine from 2,6-dichloronicotinic acid was as follows: 2,6-dichloronicotinic acid (1000 mg, 5.21 mmol) was dissolved in anhydrous tetrahydrofuran (5 mL) and the solution was cooled to 0 °C. Borane-tetrahydrofuran complex (7.82 mL, 7.82 mmol, 1.0 M tetrahydrofuran solution) was slowly added under stirring. The reaction mixture was stirred overnight at room temperature. Subsequently, water (1 mL) and potassium carbonate were added and stirring was continued for 2 hours. After completion of the reaction, the mixture was filtered and the filtrate was concentrated to give the crude product. The crude product was purified by silica gel column chromatography with the eluent being a 10:90 to 20:80 ethyl acetate/hexane solvent mixture to give 2,6-dichloro-3-hydroxymethylpyridine (876 mg, 94% yield). The structure of the product was confirmed by 1H NMR (400 MHz, MeOH-d4): δ 7.96 (d, 1H, J = 8.0 Hz), 7.45 (d, 1H, J = 8.0 Hz), 4.64 (s, 2H).

References[1] Patent: WO2006/44454, 2006, A1. Location in patent: Page/Page column 62
[2] Patent: WO2014/100695, 2014, A1. Location in patent: Paragraph 00408
[3] Patent: WO2006/85212, 2006, A2. Location in patent: Page/Page column 43
[4] Patent: US6573274, 2003, B1
(2,6-Dichloro-3-pyridinyl)methanol Preparation Products And Raw materials
Raw materials2 6-Dichloropyridine-3-carboxaldehyde-->2,6-Dichloronicotinic acid-->Borane THF-->Potassium carbonate-->Tetrahydrofuran-->Water
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