Product Name

  • Name

    Trifluralin

  • EINECS 216-428-8
  • CAS No. 1582-09-8
  • Article Data29
  • CAS DataBase
  • Density 1.337 g/cm3
  • Solubility <0.01 g/100 mL at 22.5 °C in water
  • Melting Point 48.5 °C
  • Formula C13H16F3N3O4
  • Boiling Point 369.1 °C at 760 mmHg
  • Molecular Weight 335.283
  • Flash Point 177 °C
  • Transport Information UN 2588
  • Appearance Yellow-orange crystalline solid
  • Safety 2-24-37-60-61-36-26-16
  • Risk Codes 36-43-50/53-20/21/22-11
  • Molecular Structure Molecular Structure of 1582-09-8 (Trifluralin)
  • Hazard Symbols IrritantXi,DangerousN
  • Synonyms Crisalin;Benzenamine,2,6-dinitro-N,N-dipropyl-4- (trifluoromethyl)-;Trifloran;Crisalina;Biobarrier;Synfloran;Trifluraline;TRI-4;Tristan skuaTristar;Elancolan;Nitran K;Super-Treflan;Olitref;Agreflan;Triflurex;Trefanocide;Brassix;
  • PSA 94.88000
  • LogP 5.19460

Synthetic route

C13H17F3N3O5(1-)
72283-22-8

C13H17F3N3O5(1-)

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

Conditions
ConditionsYield
With potassium hydroxide In water; dimethyl sulfoxide at 25℃; Equilibrium constant; Rate constant; var. of solvent mixture, var. KOH concentrations;
C17H26F3N4O4(1-)*K(1+)
79871-51-5

C17H26F3N4O4(1-)*K(1+)

A

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

B

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With water In dimethyl sulfoxide Equilibrium constant;
C18H26F3N4O4(1-)*K(1+)
79816-19-6

C18H26F3N4O4(1-)*K(1+)

A

piperidine
110-89-4

piperidine

B

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

Conditions
ConditionsYield
With water In dimethyl sulfoxide Equilibrium constant;
4-chloro-3,5-dinitrobenzotrifluoride
393-75-9

4-chloro-3,5-dinitrobenzotrifluoride

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

Conditions
ConditionsYield
In water
4-chloro-3,5-dinitrobenzotrifluoride
393-75-9

4-chloro-3,5-dinitrobenzotrifluoride

di-n-propylamine
142-84-7

di-n-propylamine

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

Conditions
ConditionsYield
Reflux;
With water; sodium hydroxide at 85 - 90℃; for 5h; Large scale;
With sodium hydroxide; ascorbic acid In water at 60℃; for 2h; pH=7.5 - 8.5; Temperature;33.02 g
piperidine
110-89-4

piperidine

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

C18H26F3N4O4(1-)*K(1+)
79816-19-6

C18H26F3N4O4(1-)*K(1+)

Conditions
ConditionsYield
With potassium hydroxide In water; dimethyl sulfoxide Equilibrium constant;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

C13H17F3N3O5(1-)
72283-22-8

C13H17F3N3O5(1-)

Conditions
ConditionsYield
With potassium hydroxide In water; dimethyl sulfoxide at 25℃; Equilibrium constant; Rate constant; var.of solvent mixture, var. KOH concentrations;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

N-butylamine
109-73-9

N-butylamine

C17H26F3N4O4(1-)*K(1+)
79871-51-5

C17H26F3N4O4(1-)*K(1+)

Conditions
ConditionsYield
With potassium hydroxide In water; dimethyl sulfoxide at 25℃; Rate constant; Equilibrium constant;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

1-Dipropylamino-2,6-dinitro-4-tribrommethyl-benzol
16766-93-1

1-Dipropylamino-2,6-dinitro-4-tribrommethyl-benzol

Conditions
ConditionsYield
With aluminum tri-bromide
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

A

3-nitro-5-trifluoromethyl-1,2-phenylenediamine
2078-01-5

3-nitro-5-trifluoromethyl-1,2-phenylenediamine

B

2,6-dinitro-4-trifluoromethylaniline
445-66-9

2,6-dinitro-4-trifluoromethylaniline

C

α,α,α-trifluoro-5-nitro-N4-propyltoluene-3,4-diamine
2078-02-6

α,α,α-trifluoro-5-nitro-N4-propyltoluene-3,4-diamine

D

α,α,α-trifluoro-2,6-dinitro-N-propyl-p-toluidine
2077-99-8

α,α,α-trifluoro-2,6-dinitro-N-propyl-p-toluidine

E

2,6-dinitro-4-trifluoromethyl-2',6'-dinitro-4'-<(trifluoromethyl)azo>benzene
69145-34-2

2,6-dinitro-4-trifluoromethyl-2',6'-dinitro-4'-<(trifluoromethyl)azo>benzene

F

2-ethyl-7-nitro-5-(trifluoromethyl)-1H-benzimidazole
51026-15-4

2-ethyl-7-nitro-5-(trifluoromethyl)-1H-benzimidazole

Conditions
ConditionsYield
In methanol; water Mechanism; Irradiation;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

A

di-n-propylamine
142-84-7

di-n-propylamine

B

C7H2N2O7(2-)*2K(1+)

C7H2N2O7(2-)*2K(1+)

C

potassium; 2,6-dinitro-4-trifluoromethyl-phenolate

potassium; 2,6-dinitro-4-trifluoromethyl-phenolate

D

C13H16(2)HF3N3O5(1-)*K(1+)

C13H16(2)HF3N3O5(1-)*K(1+)

E

C19H30F3N4O4(1-)*K(1+)

C19H30F3N4O4(1-)*K(1+)

Conditions
ConditionsYield
With potassium deuteroxide In dimethylsulfoxide-d6; water-d2 Mechanism; other dinitroaniline herbicides; other nucleophiles;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

trifluralin-d2

trifluralin-d2

Conditions
ConditionsYield
With deuteriated sodium hydroxide In dimethylsulfoxide-d6; water-d2 for 24h;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

α,α,α-Trifluoro-2,6-dinitro-p-cresol
393-77-1

α,α,α-Trifluoro-2,6-dinitro-p-cresol

Conditions
ConditionsYield
With sodium hydroxide; water In 1,4-dioxane for 18h; Heating;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

α,α,α-trifluoro-2,6-diamino-N,N-dipropyl-p-toluidine
2078-06-0

α,α,α-trifluoro-2,6-diamino-N,N-dipropyl-p-toluidine

Conditions
ConditionsYield
With iron In methanol
With zero-valent iron nanoparticles with palladium In methanol
With sodium tetrahydroborate In water for 0.333333h; Reagent/catalyst;
With sodium tetrahydroborate In ethanol; water at 30℃; for 0.416667h;
2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
1582-09-8

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine

A

2-ethyl-4-nitro-6-(trifluoromethyl)-1H-benzimidazole
51026-15-4

2-ethyl-4-nitro-6-(trifluoromethyl)-1H-benzimidazole

B

α,α,α-trifluoro-2,6-dinitro-N-propyl-p-toluidine
2077-99-8

α,α,α-trifluoro-2,6-dinitro-N-propyl-p-toluidine

Conditions
ConditionsYield
With 2,3-Dimethyl-2-butene; ozone Kinetics;

Trifluralin Chemical Properties

The molecular formula of  Trifluralin (1582-09-8) is C13H16F3N3O4 and its formula weight is 335.28 g/mol.
Trifluralin(1582-09-8) has the property of being dissolved in most organic solvents, xylene 58%, acetone 40% , ethanol, 7%. It is not soluble in water.
The chemical synonyms of  Trifluralin (1582-09-8) are Trifurex ; TRIFLUREX ; TRIFLURALIN ; trilin 4ec ; Trifiuralin ; treflam ; TREFLAN ; TREFLAN(R). Its  IUPAC Name is 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)aniline.
The molecular structure of  Trifluralin (1582-09-8):

Index of Refraction: 1.527
Density: 1.337 g/cm3
Flash Point: 177 °C
Melting point 48.5 °C
Surface Tension: 41.6 dyne/cm 
Enthalpy of Vaporization: 61.58 kJ/mol
Boiling Point: 369.1 °C at 760 mmHg
Vapour Pressure: 1.21E-05 mmHg at 25 °C 
Water solubility of  Trifluralin (1582-09-8):  <0.01 g/100 mL at 22.5 °C 
Appearance of  Trifluralin (1582-09-8): Yellow-orange crystalline solid

Trifluralin Uses

Trifluralin (1582-09-8) is used as herbicides for fruit, cotton, soybeans and other crops.

Trifluralin Toxicity Data With Reference

1.    

mma-sat 1 mg/plate

    ENMUDM    Environmental Mutagenesis. 8 (Suppl 7)(1986),1.
2.    

mrc-asn 100 µg/plate

    AISSAW    Annali dellIstituto Superiore di Sanita. 18 (1982),123.
3.    

cyt-hmn:lym 2 ppm

    PATHAB    Pathologica. 73 (1981),707.
4.    

sce-hmn:lym 1 mg/L

    BSIBAC    Bolletino della Societe Italiana di Biologia Sperimentale. 60 (1984),2149.
5.    

cyt-mus-ipr 200 mg/kg

    EESADV    Ecotoxicology and Environmental Safety. 4 (1980),263.
6.    

orl-mus TDLo:10 mg/kg (6-15D preg):TER

    TJADAB    Teratology, A Journal of Abnormal Development. 15 (1977),15A.
7.    

ipr-mus TDLo:200 mg/kg (1D male):REP

    EESADV    Ecotoxicology and Environmental Safety. 4 (1980),263.
8.    

orl-mus TDLo:180 g/kg/78W-C:CAR

    NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-34 ,1978.
9.    

ipr-mus TDLo:2600 µg/kg/39D-I:ETA

    PATHAB    Pathologica. 73 (1981),707.
10.    

orl-mus TD:340 g/kg/78W-C:CAR

    NCITR*    National Cancer Institute Carcinogenesis Technical

Trifluralin Consensus Reports

NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-34 ,1978. ; No Evidence: rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-34 ,1978. . EPA Genetic Toxicology Program. Community Right-To-Know List.

Trifluralin Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Human mutation data reported. When heated to decomposition it emits very toxic fumes of F and NOx. See also FLUORIDES.
Hazard Codes: IrritantXi,DangerousN,HarmfulXn,FlammableF
Risk Statements: 36-43-50/53-20/21/22-11
 R36:Irritating to eyes. 
R43:May cause sensitization by skin contact. 
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R11:Highly flammable.
Safety Statements: 2-24-37-60-61-36-26-16 
S2:Keep out of the reach of children. 
S24:Avoid contact with skin. 
S37:Wear suitable gloves. 
S60:This material and its container must be disposed of as hazardous waste. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S16:Keep away from sources of ignition.
RIDADR: UN 2588
RTECS: XU9275000
Hazardous Substances Data: 1582-09-8(Hazardous Substances Data)

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