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1929-82-4

Basic Information
CAS No.: 1929-82-4
Name: Nitrapyrin
Article Data: 8
Molecular Structure:
Molecular Structure of 1929-82-4 (Nitrapyrin)
Formula: C6H3Cl4N
Molecular Weight: 230.909
Synonyms: 2-Chloro-6-Trichloromethylpyridine;2-Trichloromethyl-6-chloropyridine;6-Chloro-2-(trichloromethyl)pyridine;N-Serve;N-Serve 24E;2-Chloro-6-(trichloromethyl)pyridine;
EINECS: 217-682-2
Density: 1.582 g/cm3
Melting Point: 62-63 °C
Boiling Point: 258.2 °C at 760 mmHg
Flash Point: 134.9 °C
Solubility: insoluble in water
Appearance: colorless crystals or off-white crystalline solid
Hazard Symbols: HarmfulXn, DangerousN
Risk Codes: 22-51/53-36/37/38
Safety: 24-61-37/39-26
Transport Information: UN 2811
PSA: 12.89000
LogP: 3.56170
Synthetic route
109-06-8

α-picoline

1929-82-4

nitrapyrin

Conditions
ConditionsYield
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℃;
14401-91-3

picoline hydrochloride

A

4377-37-1

2-trichloromethylpyridine

B

55934-01-5

2,3,5-trichloropyridine

C

1128-16-1

2-(trichloromethyl)-3,5-dichloropyridine

D

51492-01-4

2,3-dichloro-6-(trichloromethyl)pyridine

E

1929-82-4

nitrapyrin

F

1201-30-5

3,4,5-trichloro-2-trichloromethyl pyridine

Conditions
ConditionsYield
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;
14401-91-3

picoline hydrochloride

A

4377-37-1

2-trichloromethylpyridine

B

1197-03-1

2-(trichloromethyl)-5-chloropyridine

C

1128-16-1

2-(trichloromethyl)-3,5-dichloropyridine

D

1817-13-6

2,5-dichloro-6-(trichloromethyl)pyridine

E

1929-82-4

nitrapyrin

F

1817-12-5

2-(trichloromethyl)-3-chloropyridine

Conditions
ConditionsYield
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.
109-06-8

α-picoline

14401-91-3

picoline hydrochloride

A

1817-13-6

2,5-dichloro-6-(trichloromethyl)pyridine

B

1929-82-4

nitrapyrin

Conditions
ConditionsYield
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;
109-06-8

α-picoline

14401-91-3

picoline hydrochloride

A

4377-37-1

2-trichloromethylpyridine

B

1817-13-6

2,5-dichloro-6-(trichloromethyl)pyridine

C

1929-82-4

nitrapyrin

Conditions
ConditionsYield
Stage #1: α-picoline; picoline hydrochloride With chlorine Industry scale;
Stage #2: With chlorine Product distribution / selectivity; UV-irradiation; Industry scale;
109-06-8

α-picoline

14401-91-3

picoline hydrochloride

1929-82-4

nitrapyrin

Conditions
ConditionsYield
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;
1929-82-4

nitrapyrin

371-40-4

4-fluoroaniline

137640-94-9

6-chloro-N-(4-fluorophenyl)pyridin-2-amide

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate; oxygen In N,N-dimethyl-formamide at 25 - 30℃; Temperature; Reagent/catalyst; Solvent; Electrolysis;97%
With hydrogenchloride; triethylamine In toluene95%
Stage #1: nitrapyrin With sulfuric acid at 135℃; for 6h;
Stage #2: 4-fluoroaniline With triethylamine In toluene at 20 - 120℃; for 1.75h;
1929-82-4

nitrapyrin

2-fluoro-6-(trifluoromethyl)pyridine

Conditions
ConditionsYield
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;
1929-82-4

nitrapyrin

137640-94-9

6-chloro-N-(4-fluorophenyl)pyridin-2-amide

Conditions
ConditionsYield
With sulfuric acid95%
With sulfuric acid
With sulfuric acid
1929-82-4

nitrapyrin

98-17-9

3-Trifluoromethylphenol

2-(3-trifluoromethylphenoxy)-6-trichloromethylpyridine

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide; toluene at 150℃; for 8h;95%
Downstream Products
1817-13-6
51492-01-4
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    Product Name: Nitrapyrin CAS: 1929-82-4 MF: C6H3Cl4N MW: 230.91 EINECS: 217-682-2 Mol File: 1929-82-4.mol Nitrapyrin Structure Nitrapyrin Chemical Properties Melting point 62-63°C Boiling point 136-138°C density

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Consensus Reports

NCI Carcinogenesis Studies (ipr); Clear Evidence: mouse, rat RRCRBU    Recent Results in Cancer Research. 52 (1975),1. . Reported in EPA TSCA Inventory.

Standards and Recommendations

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

Specification

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%.

Pyridine,2-chloro-6-(trichloromethyl)- can be used to produce 2-chloro-6-dichloromethyl-pyridine at the ambient temperature

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.