321845-12-9

Basic information

• Product Name: 6-chloro-5-nitropyridin-3-ylmethanol
• CAS NO: 321845-12-9
• Molecular Weight: 188.57
• Mol File: 321845-12-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 6-chloro-5-nitropyridin-3-ylmethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-5-nitropyridin-3-ylmethanol(321845-12-9)
• EPA Substance Registry System: 6-chloro-5-nitropyridin-3-ylmethanol(321845-12-9)

Safety Data

• Hazardous Substances Data: 321845-12-9(Hazardous Substances Data)

Usage

General Description

6-chloro-5-nitropyridin-3-ylmethanol is a chemical compound with the molecular formula C6H5ClN2O3. It is a yellow crystalline solid and is primarily used as a building block in the synthesis of pharmaceuticals and agrochemicals. 6-chloro-5-nitropyridin-3-ylmethanol is also used as an intermediate in the production of various organic compounds. It is important to handle 6-chloro-5-nitropyridin-3-ylmethanol with care, as it can be toxic if ingested or inhaled and may cause irritation to the eyes and skin. Proper safety precautions and handling procedures should be followed when working with this chemical.

Upstream product

• 7477-10-3 6-chloro-5-nitronicotinic acid 

Downstream Products

• 321845-13-0 5-amino-6-chloropyridin-3-ylmethanol 
• 321845-11-8 5-azido-6-chloropyridin-3-ylmethyl chloride 

Relevant articles and documents

5-Azidoimidacloprid and an acyclic analogue as candidate photoaffinity probes for mammalian and insect nicotinic acetylcholine receptors

The 5-azido analogue of the major insecticide imidacloprid, 1-(5-azido-6-chloropyridin-3-ylmethyl)-2-nitroiminoimidazolidine (1), and an acyclic analogue, N-(5-azido-6-chloropyridin-3-ylmethyl)-N′-methyl-N″′-nitrog uanidine (2), were prepared in good yields as candidate photoaffinity probes for mammalian and insect nicotinic acetylcholine receptors (nAChRs). The essential intermediate was 5-azido-6-chloropyridin-3-ylmethyl chloride (3) prepared in two ways: from 6-chloro-5-nitronicotinic acid by selective reduction and then diazotization, and from N-(6-chloropyridin-3-ylmethyl)morpholine by an electrophilic azide introduction with lithium diisopropylamide followed by chlorine substitution of morpholine with ethyl chloroformate. Coupling of 3 with 2-nitroiminoimidazolidine gave 1. Conversion of 3 to 2 was achieved in good yields via the hexahydrotriazine intermediate 14. Fortuitously, the azido substituent in 1 and 2 increases the affinity 7-79-fold for rat brain and recombinant α4β2 nAChRs (Kis 4.4-60 nM competing with [3H](-)-nicotine) while maintaining high potency on both insect nAChRs (Drosophila and Myzus) (Kis 1-15 nM competing with [3H]imidacloprid). Azidopyridinyl compounds 1 and 2 are therefore candidate photoaffinity probes for characterization of both mammalian and insect receptors.