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2-Chloro-5-Hydroxymethylpyridine

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Name

2-Chloro-5-Hydroxymethylpyridine

EINECS -0
CAS No. 21543-49-7 Density 1.324 g/cm3
PSA 33.12000 LogP 1.22730
Solubility N/A Melting Point 51-54 °C(lit.)
Formula C6H6ClNO Boiling Point 276.7 °C at 760 mmHg
Molecular Weight 143.573 Flash Point 121.2 °C
Transport Information N/A Appearance white crystalline powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 21543-49-7 (2-Chloro-5-hydroxymethylpyridine) Hazard Symbols IrritantXi
Synonyms

(6-Chloro-3-pyridinyl)methanol;2-Chloro-5-pyridinemethanol;5-Hydroxymethyl-2-chloropyridine;6-Chloro-3-pyridinemethanol;2-Chloro-5-hydroxymethylpyridine;(6-chloropyridin-3-yl)methanol;2-chloro-5-Hydroxymethyl Pyridine;

Article Data 42

2-Chloro-5-Hydroxymethylpyridine Specification

The 2-Chloro-5-Hydroxymethylpyridine, with the cas register number 21543-49-7, has other names as 2-chloro-5-hydroxymethylpyridine; 6-chloropyridine-3-methanol; (6-chloropyridin-3-yl)methanol; 6-chloro-3-(hydroxymethyl)pyridine; 6-chloro-3-pyridinemethanol; (6-chloro-3-pyridinyl)methanol; 2-chloro-2-(hydroxymethyl)pyridine; 6-chloropyridine-3-methanol,98%.

The physical properties of this chemical are as followings: (1)ACD/LogP: 0.21; (2)#H bond acceptors: 2; (3)#H bond donors: 1; (4)#Freely Rotating Bonds: 2; (5)Polar Surface Area: 22.12; (6)Index of Refraction: 1.572; (7)Molar Refractivity: 35.69 cm3; (8)Molar Volume: 108.4 cm3; (9)Polarizability: 14.14 ×10-24 cm3; (10)Surface Tension: 51.7 dyne/cm; (11)Density: 1.324 g/cm3; (12)Flash Point: 121.2 °C; (13)Enthalpy of Vaporization: 54.43 kJ/mol; (14)Boiling Point: 276.7 °C at 760 mmHg; (15)Vapour Pressure: 0.00227 mmHg at 25°C.

This is a kind of white crystalline powder, and is insoluble in water while soluble in Chloroform and methyl alcohol. This chemical could be the medical intermediate, such as being the intermediate of pesticide, such as imidacloprid and  acetamiprid. When comes to its product categories, they are various, including pyridine; fluorobenzene; alcohols and derivatives; heterocycles; hydroxymethyl's; pyridines; chloropyridines; halopyridines; boronic acid; c6heterocyclic building blocks; halogenated heterocycles; heterocyclic building blocks; while its raw materials are including ethyl acetate, dichloromethane, potassium carbonate, chloroform, hydrogen, 2-chloro-3-cyanopyridine, 2-(hydroxymethyl)pyridine.

It is irritant  to eyes, respiratory system and skin, and it may cause inflammation to the skin or other mucous membranes. Therefore, we should be very cautious while using this chemical. Wear suitable protective clothing, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. You could also refer to WGK Germany  3 to obtain more safety information.

People could produce this chemical through the following two ways. The first method is belowL: 2-chloro-5-chloromethylpyridine reacts with sodium acetate in the solvent to generate acetic acid ester,and then go through the hydrolyzation to obtain this chemical. The second method: Firstly, in the hydrogenation reactor, add 2-Chloro-3-cyanopyridine methyl alcohol and 6%H2SO4 aqueous solution, and then plus Raney nickel (containing water), stir, and then go through the hydrogen till it finish its reaction; Secondly, remove the catalytic agent and boil off methyl alcohol, and get the residue; Thirdly, neutralize the residue with NaOH aqueous solution and then extract with chloroform and lastly boil off chloroform and then you could get this chemical.

With a list of the following reaction gragphic, this chemical could be the reactant and also the resultant in the labrary.
6-chloro-nicotinic acid could react in the following conditions to produce 2-Chloro-5-Hydroxymethylpyridine: (1) reagent: LiAlH4 and solvent: tetrahydrofuran; reaction time: 2 hours; reaction temperature: 0 ℃; yield: 60%. (2) reagent: DIBAL and solvent: toluene; reaction time: 2 hours; reaction temperature: Ambient temperature; yield: 70%. (3) reagent: borane dimethyl sulfide complex and solvent: tetrahydrofuran; reaction time: 16 hours; reaction temperature: Heating; yield: 79%.


Besides, 2-Chloro-5-Hydroxymethylpyridine could react with 1-(2-amino-9H-purin-6-yl)-4-dimethylamino-pyridinium; chloride in the following reaction to produce 6-(6-chloro-pyridin-3-ylmethoxy)-9H-purin-2-ylamine: (1) reagent: NaH and solvent: dimethylsulfoxide; reaction time: 45 min/72 hour(s); reaction temperature: 60 ℃; yield: 62%.

In addition, you could obtain the molecular structure by converting the following datas:
SMILES:Clc1ncc(cc1)CO
InChI:InChI=1/C6H6ClNO/c7-6-2-1-5(4-9)3-8-6/h1-3,9H,4H2
InChIKey:GOXYBEXWMJZLJB-UHFFFAOYAF

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