2,6-Dichloro-4-nitroaniline Chemical Properties

Melting point:

190-192 °C (lit.)

Boiling point:

130°C 2mm

Density 

1.6257 (rough estimate)

vapor pressure 

1.6 x 10^-4 Pa (20 °C)

refractive index 

1.6560 (estimate)

Flash point:

130°C/2mm

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

0.006g/l (HSDB)

form 

powder

pka

pK1:-3.31(+1) (25°C)

color 

Light Yellow to Yellow

Water Solubility 

1 g/L (60 ºC)

BRN 

1459581

LogP

2.800

CAS DataBase Reference

99-30-9(CAS DataBase Reference)

NIST Chemistry Reference

2,6-Dichloro-4-nitroaniline(99-30-9)

EPA Substance Registry System

Dichloran (99-30-9)

Safety Information

Hazard Codes 

Xi,Xn,N,T+

Risk Statements 

33-36/37/38-20/21/22-51/53-26/27/28

Safety Statements 

22-26-36-37/39-61-45-36/37-28

RIDADR 

2811

WGK Germany 

3

RTECS 

BX2975000

TSCA 

Yes

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29214210

Hazardous Substances Data

99-30-9(Hazardous Substances Data)

MSDS

• Language:English Provider:2,6-Dichloro-4-nitroaniline
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,6-Dichloro-4-nitroaniline Usage And Synthesis

Chemical Properties

yellow granular powder and chunks

Chemical Properties

Dicloran is a yellow crystalline solid or power. Odorless.

Uses

Dicloran is a protectant fungicide used to control various rots pathogens (Botrytis, Monilinia, Rhizopus and Sclerotinia) in a wide variety of fruits and vegetables.

Uses

It is used as dyestuff, agricultural and pharmaceutical intermediate.

Uses

Dichloran is a component for pesticide formulations.

Definition

ChEBI: A nitroaniline that is 4-nitroaniline in which the hydrogens at positions 2 and 6 are replaced by chlorines. An agricultural fungicide, it is not approved for use in the European Union.

Agricultural Uses

Fungicide: Used to control fungi on a variety of crops. The top crop usages in California are on celery, head lettuce, and grapes (table, wine and raisin). Not approved for use in EU countries. Actively registered in the U.S. Sixty-five global suppliers.

Trade name

AL-50®; ALLISAN®; BORTRAN®; BOTRAN®; DITRANIL®; FUMITE DICLORAN SMOKE ACARICIDE®; RESISAN®; RD-6584®; U-2069®

Synthesis

The general procedure for the synthesis of 2,6-dichloro-4-nitroaniline from 4-nitroaniline was as follows: 30 mL of the mother liquor obtained in step 1) was added to a 500 mL three-necked flask with 13.8 g (0.1 mol) of p-nitroaniline, and the mixture was cooled down to 10 °C under mechanical stirring. Subsequently, 25.5 mL of 30% hydrogen peroxide solution (dried and processed at 20°C) was slowly added dropwise for 2 hours. Upon completion of the reaction, the mixture was allowed to stand at room temperature until a solid precipitate precipitated. The filter cake and the filtrate were separated by filtration, and the filter cake was dried at 65 °C for 4 hours to give 20.5 g of 2,6-dichloro-4-nitroaniline in 99.0% yield. The volume of the filtrate collected in step 3) was about 240 mL, and the concentration of HCl in the filtrate was measured to be 25.8% by titration using 1 mol/L sodium hydroxide standard solution.

Potential Exposure

Dichloran is a substituted benzene/ chlorophenyl fungicide Used to control fungi on a variety of crops. The top crop usages in California are on celery, head lettuce, and grapes (table, wine and raisin).

Metabolic pathway

The metabolism of 2,6-dichloro-4-nitroaniline (DCNA) in rat hepatic microsomes gives rise to the unique metabolite 3,5-dichloro-4-aminophenol (DCAP).

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required

Purification Methods

Crystallise Dichloran from aqueous EtOH or *benzene/EtOH. [Beilstein 12 IV 1681.]

Degradation

Dicloran (1) is stable to hydrolytic degradation (pH 5-9) up to 300 °C. Degradation occurred when dicloran in pH 7 solution was irradiated with UV light (>290 nm); the estimated DT₅₀ was 41 days (PM). Smith-Downey and Fordham (1990) reported the hydrolysis of dicloran in 6 M base to yield 3,5-dichloro-4-aminophenol(2) as the only product detected.

Incompatibilities

Keep away from strong oxidizing agents, strong acids; acid anhydrides; acid chlorides; acetic anhydride; and carbon dioxide

Waste Disposal

Consult with a licensed waste disposal service or environmental regulatory agencies for guidance on acceptable disposal practices. Dissolve or mix material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber

References

[1] Patent: CN104592044, 2016, B. Location in patent: Paragraph 0038; 0039; 0091
[2] Patent: CN104610071, 2016, B. Location in patent: Paragraph 0037-0039
[3] Synthetic Communications, 2012, vol. 42, # 24, p. 3655 - 3663,9
[4] Patent: CN105461571, 2016, A. Location in patent: Paragraph 0042; 0043; 0044; 0045; 0046
[5] Tetrahedron Letters, 2003, vol. 44, # 21, p. 4085 - 4088

2,6-Dichloro-4-nitroaniline(99-30-9)Related Product Information

• 2,6-Dichloroaniline
• N-Methyl-4-nitroaniline
• 2,6-DICHLORO-4-NITRO ANILINE(2,6-DCPNA)
• 3-Nitroaniline
• 4-Nitroaniline
• 4-Chloro-2-nitroaniline
• 2-Nitroaniline
• 2-Chloro-4-nitroaniline
• 3,4-DICHLORO-2-NITROANILINE,3,4-DICHLORO-2-NITROANILINE
• 2,5-DICHLORO-4-NITROANILINE,2,5-DICHLORO-4-NITROANILINE
• 3,5-dichloro-2-nitroaniline,3,5-dichloro-2-nitroaniline
• 4,5-Dichloro-2-nitroaniline
• 2,4-DICHLORO-6-NITROANILINE
• 3,5-DICHLORO-4-NITROANILINE,3,5-DICHLORO-4-NITROANILINE
• 2,6-Dichloro-4-nitroaniline
• Nitroaniline
• 2,6-dichloro-3-nitroaniline,2,6-dichloro-3-nitroaniline
• 2,4-Dichloro-5-nitroaniline,2,4-Dichloro-5-nitroaniline