2,6-Dichlor-4-nitroanilin

Bezeichnung:2,6-Dichlor-4-nitroanilin

CAS-Nr99-30-9

Englisch Name:2,6-Dichloro-4-nitroaniline

CBNumberCB9854765

SummenformelC6H4Cl2N2O2

Molgewicht207.01

MOL-Datei99-30-9.mol

Synonyma

2,6-Dichlor-4-nitroanilin

2,6-Dichlor-4-nitrobenzolamin

DCNA

2,6-Dichlor-4-nitroanilin physikalisch-chemischer Eigenschaften

Schmelzpunkt	190-192 °C (lit.)
Siedepunkt	130°C 2mm
Dichte	1.6257 (rough estimate)
Dampfdruck	1.6 x 10^-4 Pa (20 °C)
Brechungsindex	1.6560 (estimate)
Flammpunkt	130°C/2mm
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit	0.006g/l (HSDB)
pka	pK1:-3.31(+1) (25°C)
Aggregatzustand	powder
Farbe	Light Yellow to Yellow
Wasserlöslichkeit	1 g/L (60 ºC)
BRN	1459581
Henry's Law Constant	1.2×10² mol/(m³Pa) at 25℃, HSDB (2015)
InChI	1S/C6H4Cl2N2O2/c7-4-1-3(10(11)12)2-5(8)6(4)9/h1-2H,9H2
InChIKey	BIXZHMJUSMUDOQ-UHFFFAOYSA-N
SMILES	Nc1c(Cl)cc(cc1Cl)[N+]([O-])=O
LogP	2.800
CAS Datenbank	99-30-9(CAS DataBase Reference)
NIST chemische Informationen	2,6-Dichloro-4-nitroaniline(99-30-9)
EPA chemische Informationen	Dichloran (99-30-9)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn,N,T+
R-Sätze:	33-36/37/38-20/21/22-51/53-26/27/28
S-Sätze:	22-26-36-37/39-61-45-36/37-28
RIDADR	2811
WGK Germany	3
RTECS-Nr.	BX2975000
TSCA	TSCA listed
HazardClass	6.1(b)
PackingGroup	III
HS Code	29214210
Speicherklasse	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Acute Tox. 1 Dermal Acute Tox. 2 Inhalation Acute Tox. 2 Oral Aquatic Chronic 1 STOT RE 2
Giftige Stoffe Daten	99-30-9(Hazardous Substances Data)

Gefahreninformationscode (GHS)

2,6-Dichloro-4-nitroaniline Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
GERUCHLOSE GELBE KRISTALLE.
PHYSIKALISCHE GEFAHREN
Staubexplosion der pulverisierten oder granulierten Substanz in Gemischen mit Luft möglich.
CHEMISCHE GEFAHREN
Zersetzung beim Erhitzen oder Verbrennen unter Bildung giftiger und ätzender Rauche mit Stickstoffoxiden und Chlorwasserstoff.
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation des Aerosols und durch Verschlucken.
INHALATIONSGEFAHREN
Nur ungenügende Angaben vorhanden über die Geschwindigkeit, mit der eine gesundheitsschädliche Konzentration in der Luft beim Verdampfen bei 20°C erreicht wird.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt die Augen, die Haut und die Atemwege.
LECKAGE
NICHT in die Kanalisation spülen. Verschüttetes Material in Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen. Persönliche Schutzausrüstung: Atemschutzgerät, P2-Filter für schädliche Partikel.
R-Sätze Betriebsanweisung:
R33:Gefahr kumulativer Wirkungen.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
Dicloran is a protective fungicide. It has a low aqueous solubility and is volatile. Based on its chemical properties, it may leach to groundwater. It can also be quite persistent in soils but not usually so in water. It is moderately toxic to mammals but is not expected to bioaccumulate. Exposure may damage reproduction and/or development. Dicloran is moderately toxic to most aquatic organisms, birds, honeybees and earthworms.
Chemische Eigenschaften
yellow granular powder and chunks
Chemische Eigenschaften
Dicloran is a yellow crystalline solid or power. Odorless.
Verwenden
It is used as dyestuff, agricultural and pharmaceutical intermediate.
Verwenden
Dicloran is a protectant fungicide used to control various rots pathogens (Botrytis, Monilinia, Rhizopus and Sclerotinia) in a wide variety of fruits and vegetables.
Verwenden
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.
Landwirtschaftliche Anwendung
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.
Handelsname
AL-50®; ALLISAN®; BORTRAN®; BOTRAN®; DITRANIL®; FUMITE DICLORAN SMOKE ACARICIDE®; RESISAN®; RD-6584®; U-2069®
Mechanism of action
Protective, contact action, thought to act by inhibiting respiration inhibiting spore germination. Lipid peroxidation inhibitor.
Synthese

100-01-6

99-30-9

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.
mögliche Exposition
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).
Stoffwechselwegen
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).
Versand/Shipping
UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required
läuterung methode
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.
Inkompatibilitäten
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
Einzelnachweise
[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
Pestizidtyp
Fungicide

2,6-Dichloro-4-nitroaniline Upstream-Materialien And Downstream Produkte

2,6-Dichlor-4-nitroanilin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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