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Chemical Structure| 6959-48-4 Chemical Structure| 6959-48-4
Chemical Structure| 6959-48-4

3-(Chloromethyl)pyridine HCl

CAS No.: 6959-48-4

4.5 *For Research Use Only !

Cat. No.: A257736 Purity: 95%

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Product Citations

Product Citations

Boyao Zhang ; George-Eugen Maftei ; Bartosz Bartmanski ; Michael Zimmermann ;

Abstract: Organic carcinogens, in particular DNA-reactive compounds, contribute to the irreversible initiation step of tumorigenesis through introduction of genomic instability. Although carcinogen bioactivation and detoxification by human enzymes has been extensively studied, carcinogen biotransformation by human-associated bacteria, the microbiota, has not yet been systematically investigated. We tested the biotransformation of 68 mutagenic carcinogens by 34 bacterial species representative for the upper and lower human gastrointestinal tract and found that the majority (41) of the tested carcinogens undergo bacterial biotransformation. To assess the functional consequences of microbial carcinogen metabolism, we developed a pipeline to couple gut bacterial carcinogen biotransformation assays with Ames mutagenicity testing and liver biotransformation experiments. This revealed a bidirectional crosstalk between gut microbiota and host carcinogen metabolism, which we validated in gnotobiotic mouse models. Overall, the systematic assessment of gut microbiota carcinogen biotransformation and its interplay with host metabolism highlights the gut microbiome as an important modulator of exposome-induced tumorigenesis.

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Product Details of 3-(Chloromethyl)pyridine HCl

CAS No. :6959-48-4
Formula : C6H7Cl2N
M.W : 164.03
SMILES Code : ClCC1=CC=CN=C1.[H]Cl
MDL No. :MFCD00012818

Safety of 3-(Chloromethyl)pyridine HCl

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P261-P280-P305+P351+P338-P310
Class:8
UN#:3261
Packing Group:

Application In Synthesis of 3-(Chloromethyl)pyridine HCl

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 6959-48-4 ]

[ 6959-48-4 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 6959-48-4 ]
  • [ 53052-06-5 ]
  • [ 88594-61-0 ]
  • 3
  • [ 6959-48-4 ]
  • [ 39903-01-0 ]
  • [ 941603-84-5 ]
YieldReaction ConditionsOperation in experiment
29% With potassium carbonate; sodium iodide; In acetone;Heating / reflux; 00 suspension of <strong>[39903-01-0]2-amino-5-bromo-pyridin-3-ol</strong> (1.00 g, 5.29 mmol) in acetone (40 mL) was added to a solution of 3-chloromethylpyridine hydrochloride (1.12 g, 6.87 mmol), K2CO3 (2.19 g, 15.8 mmol) and NaI (2.37 g, 15.8 mmol). The mixture was heated to reflux overnight. After cooling, the mixture was dissolved in water and extracted with EtOAc (3x). The combined organics were washed with brine, dried and concentrated. Purification by column chromatography (silica gel, hexanes/EtOAc, 1 :4) gave the title compound (430 mg, 29percent) as a brown oil: 1H NMR (300 MHz, DMSO-^) delta 8.71 (d, J= 1.8 Hz, IH), 8.55 (d, J= 3.0 Hz IH), 7.96-7.92 (m, IH), 7.60 (d, J= 3.0 Hz, IH), 7.45-7.35 (m, IH), 7.34 (d, J= 3.0 Hz, IH), 6.04 (br s, 2H), 5.20 (s, 2H); ESI MS m/z 280 (M + H)+.
  • 4
  • [ 6959-48-4 ]
  • [ 71486-53-8 ]
  • [ 1225498-23-6 ]
YieldReaction ConditionsOperation in experiment
100% With N-ethyl-N,N-diisopropylamine; sodium iodide; In acetonitrile; at 80℃; for 1h; 0.200 g (1.034 mmol) of 1-methyl-4-oxopiperidine-3-carboxylate hydrochloride (commercially available, ABCR), 0.54 mL (3.102 mmol) of diisopropylethylamine, 0.155 g (1.034 mmol) of sodium iodide and 0.170 g (1.034 mmol) of 3-(chloromethyl)pyridine hydrochloride were stirred at 80 °C in 5.0 mL of anhydrous CH3CN.The reaction was monitored by HPLC and UPLC-MS. After 1h at 80°C, the insoluble inorganic materials were filtered off and the filtrate was concentrated in vacuo to give a yellowish residue.This residue was dissolved in CH2C12, washed with brine, H2O, dried over Na2SO4 and concentrated in vacuo to give pure methyl 4-oxo-1-(pyridin-3-ylmethyl)piperidine-3-carboxylate (0.257 g, 1.034 mmol, quantitative yield).The product was used for the next step without further manipulation.
With N-ethyl-N,N-diisopropylamine; sodium iodide; In acetonitrile; at 80℃; for 1h; 0.200 g (1.034 mmol) of l-methyl-4-oxopiperidine-3-carboxylate hydrochloride (commercially available, ABCR), 0.54 mL (3.102 mmol) of diisopropylethylamine, 0.155 g (1.034 mmol) of sodium iodide and 0.170 g (1.034 mmol) of 3- (chloromethyl)pyridine hydrochloride were stirred at 80 °C in 5.0 mL of anhydrous CH3CN. The reaction was monitored by HPLC and UPLC-MS. After lh at 80°C, the insoluble inorganic materials were filtered off and the filtrate was concentrated in vacuo to give a yellowish residue. This residue was dissolved in CH2CI2, washed with brine, H20, dried over Na2S04 and concentrated in vacuo to give pure methyl 4-oxo-l- (pyridin-3-ylmethyl)piperidine-3-carboxylate (0.257 g, 1.034 mmol, quantitative yield). The product was used for the next step without further manipulation
  • 5
  • [ 6959-48-4 ]
  • [ 71486-53-8 ]
  • 2-phenyl-5-(pyridin-3-ylmethyl)-1,4,5,6,7-hexahydro-3H-pyrazolo[4,3-c]pyridin-3-one [ No CAS ]
  • 6
  • [ 6959-48-4 ]
  • [ 71486-53-8 ]
  • [ 1331732-74-1 ]
 

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