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C1930

Sigma-Aldrich

2-Chloro-6-(trichloromethyl)pyridine

≥98%

Synonym(s):

Nitrapyrin, 2-Chloro-6-(trichloromethyl)pyridine, CP

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About This Item

Empirical Formula (Hill Notation):
C6H3Cl4N
CAS Number:
Molecular Weight:
230.91
Beilstein:
1618997
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Agency

suitable for SM 5210

Assay

≥98%

form

powder

solubility

ethanol: 10 mg/mL, clear, colorless to faintly yellow

SMILES string

Clc1cccc(n1)C(Cl)(Cl)Cl

InChI

1S/C6H3Cl4N/c7-5-3-1-2-4(11-5)6(8,9)10/h1-3H

InChI key

DCUJJWWUNKIJPH-UHFFFAOYSA-N

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General description

2-Chloro-6-(trichloromethyl)pyridine is a chlorinatedheterocyclic compound that belongs to the pyridine family and serves as anactive ingredient found in commercially available nitrogen stabilizers. Iteffectively delays the conversion of ammonium (NH⁺) to nitrate (NO⁻). Thisprocess enhances nitrogen retention and improves nitrogen use efficiency,ultimately leading to increased crop yields.

Application

  • Biological and chemical nitrification inhibitors exhibited different effects on soil gross N nitrification rate and N(2)O production: a (15)N microcosm study.: This study examines the effects of biological and chemical nitrification inhibitors, including 2-Chloro-6-(trichloromethyl)pyridine, on soil nitrogen processes. The findings highlight the differential impacts on soil nitrogen dynamics and greenhouse gas emissions (Lan et al., 2023).
  • Nitrous oxide emissions from manured soils as a function of various nitrification inhibitor rates and soil moisture contents.: This paper explores the relationship between nitrification inhibitor application rates, including 2-Chloro-6-(trichloromethyl)pyridine, and soil moisture on nitrous oxide emissions, providing insights into optimizing inhibitor use for environmental benefits (Lin and Hernandez-Ramirez, 2020).
  • Nitrate losses in subsurface drainage from a corn-soybean rotation as affected by fall and spring application of nitrogen and nitrapyrin.: Investigating the seasonal application of nitrapyrin, a derivative of 2-Chloro-6-(trichloromethyl)pyridine, this study assesses its efficacy in reducing nitrate leaching and improving nitrogen use efficiency in agricultural systems (Randall and Vetsch, 2005).
  • Oxidation of Nitrapyrin to 6-Chloropicolinic Acid by the Ammonia-Oxidizing Bacterium Nitrosomonas europaea.: This foundational research elucidates the microbial degradation pathway of nitrapyrin, contributing to our understanding of its environmental fate and persistence (Vannelli and Hooper, 1992).

Pictograms

Skull and crossbonesEnvironment

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Chronic 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

212.0 °F - closed cup

Flash Point(C)

100 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Zhongqing Zhang et al.
Royal Society open science, 7(9), 200259-200259 (2020-10-14)
The nitrapyrin was easily adsorbed by soil, but most current studies have focused on comparing the effects of nitrapyrin application at different soil organic matter levels and in different soil types. The adsorption kinetics and isotherm adsorption of the nitrification
Facilitating nitrification inhibition through green, mechanochemical synthesis of a novel nitrapyrin complex
Casali, Lucia and Broll, et al.
Crystal Growth & Design, 21, 5792-5799 (2021)
Kristina Bayer et al.
Environmental microbiology, 10(11), 2942-2955 (2008-03-28)
The potential for nitrification in the Mediterranean sponge Aplysina aerophoba was assessed using a combined physiological and molecular approach. Nitrate excretion rates in whole sponges reached values of up to 344 nmol g(-1) dry weight (wt) h(-1) (unstimulated) and 1325
J A Zahn et al.
FEBS letters, 397(1), 35-38 (1996-11-11)
Binding of the ligand, nitric oxide, in the presence of reductant was used to identify a ferrous S = 3/2 signal, characteristic of a ferrous nitrosyl complex, and a g= 2.03 copper or iron signal in membranes of the ammonia-oxidizing
Q R Shen et al.
Chemosphere, 50(6), 747-753 (2003-04-12)
Because low concentration of nitrite could be toxic to biological systems and high amounts of nitrite have been observed in a river of northern China since 1990, nitrite from agricultural soil sources should be investigated. In this paper, effects of

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