Conditions | Yield |
---|---|
With chlorine In water at 240℃; Temperature; Inert atmosphere; | 89.4% |
With chlorine at 160 - 195℃; Temperature; Concentration; Irradiation; | 70.21% |
With chlorine at 186.9 - 206.9℃; |
picoline hydrochloride
A
2-trichloromethylpyridine
B
2,3,5-trichloropyridine
C
2-(trichloromethyl)-3,5-dichloropyridine
D
2,3-dichloro-6-(trichloromethyl)pyridine
E
nitrapyrin
F
3,4,5-trichloro-2-trichloromethyl pyridine
Conditions | Yield |
---|---|
With chlorine at 150℃; for 2h; Product distribution; Kinetics; Irradiation; other temp.: 80, 90, 100, 120 deg. C; other reaction time: 2 to 45 h; reaction without irradiation; reaction in C4Cl6; |
picoline hydrochloride
A
2-trichloromethylpyridine
B
2-(trichloromethyl)-5-chloropyridine
C
2-(trichloromethyl)-3,5-dichloropyridine
D
2,5-dichloro-6-(trichloromethyl)pyridine
E
nitrapyrin
F
2-(trichloromethyl)-3-chloropyridine
Conditions | Yield |
---|---|
With chlorine at 185℃; for 21h; Product distribution; Rate constant; various temperatures, residence times and chlorine feed rates; | A 28.3 % Chromat. B 2.7 % Chromat. C n/a D 1.2 % Chromat. E 64.8 % Chromat. F 0.6 % Chromat. |
α-picoline
picoline hydrochloride
A
2,5-dichloro-6-(trichloromethyl)pyridine
B
nitrapyrin
Conditions | Yield |
---|---|
Stage #1: α-picoline; picoline hydrochloride With chlorine at 195℃; for 36h; Industry scale; Stage #2: With chlorine at 170℃; for 8h; Product distribution / selectivity; UV-irradiation; Industry scale; |
α-picoline
picoline hydrochloride
A
2-trichloromethylpyridine
B
2,5-dichloro-6-(trichloromethyl)pyridine
C
nitrapyrin
Conditions | Yield |
---|---|
Stage #1: α-picoline; picoline hydrochloride With chlorine Industry scale; Stage #2: With chlorine Product distribution / selectivity; UV-irradiation; Industry scale; |
Conditions | Yield |
---|---|
Stage #1: α-picoline; picoline hydrochloride With chlorine at 195℃; Industry scale; Stage #2: With chlorine at 170℃; Product distribution / selectivity; UV-irradiation; Industry scale; |
nitrapyrin
4-fluoroaniline
6-chloro-N-(4-fluorophenyl)pyridin-2-amide
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate; oxygen In N,N-dimethyl-formamide at 25 - 30℃; Temperature; Reagent/catalyst; Solvent; Electrolysis; | 97% |
With hydrogenchloride; triethylamine In toluene | 95% |
Stage #1: nitrapyrin With sulfuric acid at 135℃; for 6h; Stage #2: 4-fluoroaniline With triethylamine In toluene at 20 - 120℃; for 1.75h; |
nitrapyrin
Conditions | Yield |
---|---|
With antimony(V) trichloride difluoride; SbF3Cl2; hydrogen fluoride at 120℃; under 3750.38 - 26252.6 Torr; for 6h; Temperature; Reagent/catalyst; Pressure; Autoclave; Inert atmosphere; Large scale; | 96.7% |
Multi-step reaction with 2 steps 1: iron(III) chloride; hydrogen fluoride / 22 h / 160 - 180 °C / 11251.1 - 18751.9 Torr 2: hydrogen fluoride / 22 h / 160 - 180 °C / 11251.1 - 18751.9 Torr View Scheme | |
With hydrogen fluoride for 15h; Time; Large scale; |
nitrapyrin
6-chloro-N-(4-fluorophenyl)pyridin-2-amide
Conditions | Yield |
---|---|
With sulfuric acid | 95% |
With sulfuric acid | |
With sulfuric acid |
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide; toluene at 150℃; for 8h; | 95% |
nitrapyrin
6-chloro-2-chloromethylpyridine
2-Chloro-6-(dichloromethyl)-pyridine
Conditions | Yield |
---|---|
90.1% |
Conditions | Yield |
---|---|
With sulfuric acid; water at 100℃; for 8h; | 90% |
With sulfuric acid at 100℃; for 6h; Time; | 90% |
Conditions | Yield |
---|---|
Stage #1: nitrapyrin With sulfuric acid at 135℃; for 6h; Stage #2: isopropyl alcohol at 20 - 65℃; for 0.5h; | 88.4% |
nitrapyrin
2-Chloro-6-(dichloromethyl)-pyridine
Conditions | Yield |
---|---|
With chloroform; sodium hydroxide Ambient temperature; | 88% |
With chloroform; sodium hydroxide In dimethyl sulfoxide Rate constant; Mechanism; Ambient temperature; other solvents; accelerating and inhibiting additives added; other catalyst (PTC); in the presence of 40percent NaOD in D2O; |
nitrapyrin
2-chloro-6-trifluoromethylpyridine
Conditions | Yield |
---|---|
With hydrogen fluoride at 330℃; | 80% |
nitrapyrin
1-t-Butoxycarbonylpiperazine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 70℃; Inert atmosphere; | 19% |
Conditions | Yield |
---|---|
With sodium 2.) reflux, 15 h; Yield given. Multistep reaction; |
nitrapyrin
A
2,3-dichloro-6-(trichloromethyl)pyridine
B
2,5-dichloro-6-(trichloromethyl)pyridine
Conditions | Yield |
---|---|
With chlorine; ZnCl2, HCl, water and type L zeolite (EZ-200) mixed, dried and calcined at 200℃; under 25.8581 Torr; for 12.5h; | |
With tetrachloromethane; chlorine; Type L zeolite (TOSOH, HSZ-500KOA Lot#50KA1103) calcined at 200℃; under 25.8581 Torr; for 11h; | |
With chlorine; Cs-ion exchanged Type L zeolite at 200℃; under 25.8581 Torr; for 8h; |
Nitroethane
nitrapyrin
4-fluoroaniline
A
6-chloro-N-(4-fluorophenyl)pyridin-2-amide
Conditions | Yield |
---|---|
With hydrogenchloride; sulfuric acid; triethylamine | |
With hydrogenchloride; sulfuric acid; triethylamine |
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; dichloromethane |
nitrapyrin
methyl phosphite
2-Chloro-6-(dichloromethyl)-pyridine
Conditions | Yield |
---|---|
With sodium hydroxide In 1-methyl-pyrrolidin-2-one; water |
nitrapyrin
B
2-chloro-6-trifluoromethylpyridine
Conditions | Yield |
---|---|
With iron(III) chloride; hydrogen fluoride at 160 - 180℃; under 11251.1 - 18751.9 Torr; for 22h; | A 90.96 %Chromat. B 7.67 %Chromat. |
nitrapyrin
C
2-chloro-6-trifluoromethylpyridine
Conditions | Yield |
---|---|
With hydrogen fluoride at 180 - 200℃; under 15001.5 - 22502.3 Torr; | A 51.87 %Chromat. B 8.22 %Chromat. C 38.66 %Chromat. |
With hydrogen fluoride at 150 - 175℃; for 12h; | A 40.28 %Chromat. B 10.22 %Chromat. C 48.49 %Chromat. |
nitrapyrin
N-(4-fluorophenyl)-6-(3-trifluoromethylphenoxy)pyridine-2-carboxamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide / toluene; dimethyl sulfoxide / 8 h / 150 °C 2: iron(III) chloride; water / 1,2-dichloro-ethane / 25 h / Resolution of racemate 3: sodium hydroxide / 1,2-dichloro-ethane; water / 3 h / 15 - 20 °C / pH 8 View Scheme | |
Multi-step reaction with 4 steps 1: sodium hydroxide / toluene; dimethyl sulfoxide / 8 h / 150 °C 2: water; hydrogenchloride / 8 h / 120 °C 3: thionyl chloride / 4 h / Reflux 4: sodium hydroxide / 1,2-dichloro-ethane; water / 3 h / 15 - 20 °C / pH 8 View Scheme | |
Multi-step reaction with 4 steps 1: sulfuric acid; water / 8 h / 100 °C 2: potassium carbonate; copper(l) chloride / N,N-dimethyl-formamide / 6 h / 140 °C 3: pyridine; bis(trichloromethyl) carbonate / ethyl acetate / 2 h / 35 - 50 °C 4: triethylamine; bis(trichloromethyl) carbonate / dichloromethane / 3 h View Scheme | |
Multi-step reaction with 4 steps 1: sulfuric acid / 6 h / 100 °C 2: potassium carbonate; copper(l) chloride / N,N-dimethyl-formamide / 8 h / 140 °C 3: bis(trichloromethyl) carbonate; triethylamine / ethyl acetate / 2 h / 35 - 50 °C 4: bis(trichloromethyl) carbonate; triethylamine / dichloromethane / 3 h View Scheme |
nitrapyrin
2-(3-trifluoromethylphenoxy)-6-pyridinecarbonyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / toluene; dimethyl sulfoxide / 8 h / 150 °C 2: iron(III) chloride; water / 1,2-dichloro-ethane / 25 h / Resolution of racemate View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydroxide / toluene; dimethyl sulfoxide / 8 h / 150 °C 2: water; hydrogenchloride / 8 h / 120 °C 3: thionyl chloride / 4 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: sulfuric acid; water / 8 h / 100 °C 2: potassium carbonate; copper(l) chloride / N,N-dimethyl-formamide / 6 h / 140 °C 3: pyridine; bis(trichloromethyl) carbonate / ethyl acetate / 2 h / 35 - 50 °C View Scheme | |
Multi-step reaction with 3 steps 1: sulfuric acid / 6 h / 100 °C 2: potassium carbonate; copper(l) chloride / N,N-dimethyl-formamide / 8 h / 140 °C 3: bis(trichloromethyl) carbonate; triethylamine / ethyl acetate / 2 h / 35 - 50 °C View Scheme |
nitrapyrin
6-(3-α,α,α-trifluoromethylphenoxy)picolinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / toluene; dimethyl sulfoxide / 8 h / 150 °C 2: water; hydrogenchloride / 8 h / 120 °C View Scheme | |
Multi-step reaction with 2 steps 1: sulfuric acid; water / 8 h / 100 °C 2: potassium carbonate; copper(l) chloride / N,N-dimethyl-formamide / 6 h / 140 °C View Scheme | |
Multi-step reaction with 2 steps 1: sulfuric acid / 6 h / 100 °C 2: potassium carbonate; copper(l) chloride / N,N-dimethyl-formamide / 8 h / 140 °C View Scheme |
nitrapyrin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran / 70 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 3 h 3: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / tetrahydrofuran / 3 h 4: dichloromethane / 3 h View Scheme |
nitrapyrin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran / 70 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 3 h 3: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / tetrahydrofuran / 3 h 4: dichloromethane / 3 h 5: triethylamine / dichloromethane / 3 h View Scheme |
nitrapyrin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran / 70 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 3 h View Scheme |
NCI Carcinogenesis Studies (ipr); Clear Evidence: mouse, rat RRCRBU Recent Results in Cancer Research. 52 (1975),1. . Reported in EPA TSCA Inventory.
OSHA PEL: Total Dust: 15 mg/m3; Respirable Fraction: 5 mg/m3
ACGIH TLV: TWA 10 mg/m3; STEL 20 mg/m3; Not Classifiable as a Human Carcinogen
The Nitrapyrin, with the CAS registry number 1929-82-4, is also known as 2-Trichloromethyl-6-chloropyridine. It belongs to the product categories of Organics; Pyridine. Its EINECS number is 217-682-2. This chemical's molecular formula is C6H3Cl4N and molecular weight is 230.91. What's more, its systematic name is 2-chloro-6-(trichloromethyl)pyridine. Its classification codes are: (1)Agricultural Chemical; (2)Fungicide, bactericide, wood preservative; (3)Growth regulator / Fertilizer; (4)Insect attractant, repellent and chemosterilant; (5)Mutation data; (6)Reproductive Effect. It is used as nitrogen and soil nitrogen oxide inhibitors and protective agents. It should be sealed and stored at the temperature of 0 - 6 °C. Moreover, it should be protected from oxides.
Physical properties of Nitrapyrin are: (1)ACD/LogP: 3.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.41; (4)ACD/LogD (pH 7.4): 3.41; (5)ACD/BCF (pH 5.5): 229.93; (6)ACD/BCF (pH 7.4): 229.93; (7)ACD/KOC (pH 5.5): 1706.24; (8)ACD/KOC (pH 7.4): 1706.24; (9)#H bond acceptors: 1; (10)Index of Refraction: 1.576; (11)Molar Refractivity: 48.275 cm3; (12)Molar Volume: 145.929 cm3; (13)Polarizability: 19.138 10-24cm3; (14)Surface Tension: 46.6119995117188 dyne/cm; (15)Density: 1.582 g/cm3; (16)Flash Point: 134.906 °C; (17)Enthalpy of Vaporization: 47.574 kJ/mol; (18)Boiling Point: 258.174 °C at 760 mmHg; (19)Vapour Pressure: 0.0219999998807907 mmHg at 25°C
Uses of Nitrapyrin: it can be used to produce 2-chloro-6-dichloromethyl-pyridine at the ambient temperature. It will need reagent CHCl3 and catalyst 50% aq. NaOH. The yield is about 88%.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. It is irritating to eyes, respiratory system and skin. It is toxic to aquatic organisms as it may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you must avoid contact with eyes and need wear suitable protective clothing and gloves. You should avoid releasing it to the environment just refering to special instructions/safety data sheet.
You can still convert the following datas into molecular structure:
(1)SMILES: ClC(Cl)(Cl)c1nc(Cl)ccc1
(2)Std. InChI: InChI=1S/C6H3Cl4N/c7-5-3-1-2-4(11-5)6(8,9)10/h1-3H
(3)Std. InChIKey: DCUJJWWUNKIJPH-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
chicken | LD50 | oral | 235mg/kg (235mg/kg) | "Pesticide Index," Frear, E.H., ed., State College, PA, College Science Pub., 1969Vol. 5, Pg. 166, 1976. | |
mouse | LD50 | oral | 710mg/kg (710mg/kg) | Guide to the Chemicals Used in Crop Protection. Vol. 6, Pg. 122, 1973. | |
mouse | LD50 | unreported | 3113mg/kg (3113mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(4), Pg. 52, 1983. | |
rabbit | LD50 | oral | 713mg/kg (713mg/kg) | Fundamental and Applied Toxicology. Vol. 11, Pg. 464, 1988. | |
rabbit | LD50 | skin | 850mg/kg (850mg/kg) | Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 819, 1966. | |
rat | LD50 | oral | 940mg/kg (940mg/kg) | Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 819, 1966. | |
rat | LD50 | unreported | 3675mg/kg (3675mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(4), Pg. 52, 1983. |
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