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Fluazinam

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Name

Fluazinam

EINECS 200-835-2
CAS No. 79622-59-6 Density 1.766 g/cm3
PSA 116.56000 LogP 7.10540
Solubility 1.7 mg l-1 (25 °C) Melting Point 113 °C
Formula C13H4Cl2F6N4O4 Boiling Point 376.1 °C at 760 mmHg
Molecular Weight 465.096 Flash Point 181.3 °C
Transport Information UN 2811 Appearance Light yellow crystals
Safety 26-36/37/39-45-60-61-36/37-16 Risk Codes 23-41-43-50/53-36-20/21/22-11
Molecular Structure Molecular Structure of 79622-59-6 (Fluazinam) Hazard Symbols ToxicT,DangerousN
Synonyms

Frowncide;Frowncide SC;IKF 1216;Mapro;PP 192;Shirlan (Zeneca);ASC66825;ASC 67178;Altima;

Article Data 14

Fluazinam Synthetic route

29091-09-6

2,4-dichloro-3,5-dinitro-benzotrifluoride

79456-26-1

2-amino-3-chloro-5-(trifluoromethyl)pyridine

79622-59-6

fluazinam

Conditions
ConditionsYield
With potassium hydroxide In 2-methyltetrahydrofuran at 20℃; for 4h; Concentration; Temperature; Solvent;98%
Stage #1: 2,4-dichloro-3,5-dinitro-benzotrifluoride; 2-amino-3-chloro-5-(trifluoromethyl)pyridine With methoxybenzene; potassium hydroxide at 55℃; for 6h;
Stage #2: With hydrogenchloride at 85℃; pH=3.7; Temperature; Reagent/catalyst; pH-value;
98.5%
With edetate disodium; potassium hydroxide In acetonitrile at 0 - 5℃; for 3h; Reagent/catalyst; Temperature;97.5%
3099-50-1

3-trichloromethyl-pyridine

79622-59-6

fluazinam

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: phosphorus pentachloride / 16 h / 210 °C / Autoclave
2: hydrogen fluoride; iron(III) chloride; pyridine / 130 - 175 °C / Autoclave
3: ammonia / water / 9 h / 80 °C / 13501.4 - 16501.7 Torr / Autoclave
4: potassium hydroxide / acetonitrile / 6.25 h / 5 - 40 °C
View Scheme
Multi-step reaction with 5 steps
1: phosphorus pentachloride / 16 h / 210 °C / Autoclave
2: phosphorus pentachloride / 16 h / 210 °C / Autoclave
3: hydrogen fluoride; iron(III) chloride; pyridine / 130 - 175 °C / Autoclave
4: ammonia / water / 9 h / 80 °C / 13501.4 - 16501.7 Torr / Autoclave
5: potassium hydroxide / acetonitrile / 6.25 h / 5 - 40 °C
View Scheme

5-chloro-3-trichloromethyl pyridine

79622-59-6

fluazinam

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: phosphorus pentachloride / 16 h / 210 °C / Autoclave
2: hydrogen fluoride; iron(III) chloride; pyridine / 130 - 175 °C / Autoclave
3: ammonia / water / 9 h / 80 °C / 13501.4 - 16501.7 Torr / Autoclave
4: potassium hydroxide / acetonitrile / 6.25 h / 5 - 40 °C
View Scheme
59-67-6

nicotinic acid

79622-59-6

fluazinam

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: phosphorus pentachloride / 14 h / 210 °C / 1500.15 - 27752.8 Torr / Autoclave
2: hydrogen fluoride; iron(III) chloride; pyridine / 130 - 175 °C / Autoclave
3: ammonia / water / 9 h / 80 °C / 13501.4 - 16501.7 Torr / Autoclave
4: potassium hydroxide / acetonitrile / 6.25 h / 5 - 40 °C
View Scheme
Multi-step reaction with 4 steps
1: phosphorus pentachloride / 64 h / 185 °C / 18751.9 - 30003 Torr / Autoclave
2: hydrogen fluoride; iron(III) chloride; pyridine / 130 - 175 °C / Autoclave
3: ammonia / water / 9 h / 80 °C / 13501.4 - 16501.7 Torr / Autoclave
4: potassium hydroxide / acetonitrile / 6.25 h / 5 - 40 °C
View Scheme
Multi-step reaction with 4 steps
1: phosphorus pentachloride / 72 h / 185 °C / 18751.9 - 30003 Torr / Autoclave
2: hydrogen fluoride; iron(III) chloride; pyridine / 130 - 175 °C / Autoclave
3: ammonia / water / 9 h / 80 °C / 13501.4 - 16501.7 Torr / Autoclave
4: potassium hydroxide / acetonitrile / 6.25 h / 5 - 40 °C
View Scheme
69045-83-6

2,3-dichloro-5-(trichloromethyl)pyridine

79622-59-6

fluazinam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen fluoride; iron(III) chloride; pyridine / 130 - 175 °C / Autoclave
2: ammonia / water / 9 h / 80 °C / 13501.4 - 16501.7 Torr / Autoclave
3: potassium hydroxide / acetonitrile / 6.25 h / 5 - 40 °C
View Scheme
69045-84-7

2,3-dichloro-5-trifluoromethylpyridine

79622-59-6

fluazinam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: ammonia / tetrahydrofuran / 28 h / 100 °C / 4500.45 - 12001.2 Torr / Autoclave; Inert atmosphere
2.1: potassium hydroxide / tetrahydrofuran / 1 h / 0 - 5 °C
2.2: 3.5 h / 0 - 10 °C
View Scheme
39716-58-0

pent-4-enoyl chloride

79622-59-6

fluazinam

C18H10Cl2F6N4O5

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 25℃; for 19h;70%
39716-58-0

pent-4-enoyl chloride

79622-59-6

fluazinam

C30H17Cl2F6N4O5S2(1+)*BF4(1-)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 19 h / 0 - 25 °C
2: trifluoroacetic anhydride; trifluoroacetic acid / acetonitrile / 1.25 h / 0 °C / Inert atmosphere
View Scheme

Fluazinam Chemical Properties

Product Name: Fluazinam (CAS NO.79622-59-6)

Molecular Formula:C13H4Cl2F6N4O4
Molar mass:465.091679g/mol
Density:1.766 g/cm 
Melting point:113°C                                        
Boiling Point:376.1 °C at 760 mmHg           
Index of Refraction:1.571
Vapour Pressure:7.41E-06 mmHg at 25°C     
Storage temp:2-8°C
Index of Refraction: 1.571 
Molar Refractivity: 86.55 cm3 
Molar Volume: 263.3 cm
XLogP3-AA: 6
H-Bond Donor: 1
H-Bond Acceptor: 12
Structure Descriptors of Fluazinam (CAS NO.79622-59-6):
  IUPAC Name: 3-chloro-N-[3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl]-5-(trifluoromethyl)pyridin-2-amine
  Canonical SMILES: C1=C(C=NC(=C1Cl)NC2=C(C=C(C(=C2[N+](=O)[O-])Cl)C(F)(F)F)[N+](=O)[O-])C
(F)(F)F
  InChI: InChI=1S/C13H4Cl2F6N4O4/c14-6-1-4(12(16,17)18)3-22-11(6)23-9-7(24(26)27)2-5(13(19,20)21)8(15)10(9)25(28)29/h1-3H,(H,22,23) 
  InChIKey: UZCGKGPEKUCDTF-UHFFFAOYSA-N
Product Categories: API intermediates

Fluazinam Uses

 Fluazinam (CAS NO.79622-59-6) is very effective to Botrytis genus Phytophthora, Plasmopara genus Sclerotinia spp and Cladosporium spp bacteria.

Fluazinam Toxicity Data With Reference

1.    

orl-qal LD50:1782 mg/kg

    HBPTO*    Handbook of pesticide toxicology. 2 (2001),1229.
2.    

ihl-rat LC50:470 mg/m3

    HBPTO*    Handbook of pesticide toxicology. 2 (2001),1229.

Fluazinam Safety Profile

Moderately toxic by ingestion and inhalation. Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NOx, F, and Cl.
Safety Information of Fluazinam (CAS NO.79622-59-6):
Hazard Codes:T;N,N,T,Xn,F
Risk Statements:
11:  Highly Flammable
20:  Harmful by inhalation
21:  Harmful in contact with skin
22:  Harmful if swallowed 
23:  Toxic by inhalation
36:  Irritating to the eyes
41:  Risk of serious damage to eyes
43:  May cause sensitization by skin contact
50:  Very Toxic to aquatic organisms
53:  May cause long-term adverse effects in the aquatic environment
Safety Statements:
16:  Keep away from sources of ignition - No smoking
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:  Wear suitable protective clothing 
37:  Wear suitable gloves
39:  Wear eye/face protection
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
60:  This material and/or its container must be disposed of as hazardous waste
61:  Avoid release to the environment. Refer to special instructions safety data sheet

Fluazinam Specification

 Fluazinam , its CAS NO. is 79622-59-6, the synonyms are 3-Chloro-n-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-2-pyridinamine ; 3-Chloro-n-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-5-2-pyridinamin ; Frowncide ; Shirlan Flow ; Shirlan (Zeneca) ; Fluazinam solution .

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