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2,6-Dichloro-4-nitroaniline

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Name

2,6-Dichloro-4-nitroaniline

EINECS 202-746-4
CAS No. 99-30-9 Density 1.624 g/cm3
PSA 71.84000 LogP 3.58820
Solubility 1 g/L in water at 60 °C Melting Point 190-192 °C(lit.)
Formula C6H4Cl2N2O2 Boiling Point 323 °C at 760 mmHg
Molecular Weight 207.016 Flash Point 149.1 °C
Transport Information UN 2811 Appearance yellow granular powder and chunks
Safety 22-26-36-37/39 Risk Codes 33-36/37/38-20/21/22
Molecular Structure Molecular Structure of 99-30-9 (2,6-Dichloro-4-nitroaniline) Hazard Symbols IrritantXi,HarmfulXn
Synonyms

Aniline,2,6-dichloro-4-nitro- (6CI,8CI);1-Amino-2,6-dichloro-4-nitrobenzene;2,6-Dichloro-4-nitrobenzenamine;2,6-Dichloro-p-nitroaniline;4-Nitro-2,6-dichloroaniline;AL 50;Allisan;Batran;Bortran;Botran;Botran 75B;Botran 75W;CNA;DCNA;Ditranil;NSC 218;U-2069;

Article Data 53

2,6-Dichloro-4-nitroaniline Synthetic route

100-01-6

4-nitro-aniline

99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With hydrogenchloride; dihydrogen peroxide In water at -8 - 20℃; for 2h; Temperature; Reagent/catalyst;99.5%
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; for 0.133333h; Green chemistry;99%
Stage #1: 4-nitro-aniline With hydrogenchloride In water at 63℃; for 0.5h;
Stage #2: With chlorine In water for 0.166667h; Temperature; Time;
98.65%
609-20-1

2,6-dichloro-p-phenylenediamine

99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h;92%
59992-52-8

2,6-dichloro-4-aminonitrobenzene

99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With nickel(II) tetrafluoroborate hexahydrate; ammonia; hydrogen; bis(2-diphenylphosphinoethyl)phenylphosphine In 2,2,2-trifluoroethanol at 120℃; under 37503.8 Torr; for 24h; chemoselective reaction;90%
100-01-6

4-nitro-aniline

A

99-30-9

4-nitro-2,6-dichloroaniline

B

121-87-9

2-Chloro-4-nitroaniline

Conditions
ConditionsYield
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In 1,4-dioxane at 20 - 25℃; Solvent; Green chemistry;A n/a
B 50%
With hydrogenchloride; sodium chlorate In water; acetic acid at 20℃; for 40h;A 9%
B 32%
Chlorierung;
With methanol; chlorine
22134-75-4

4-amino-3,5-dichloro-benzenesulfonamide

99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With ammonium nitrate; sulfuric acid at 0 - 5℃; for 0.25h;21%
100-01-6

4-nitro-aniline

A

99-30-9

4-nitro-2,6-dichloroaniline

B

121-87-9

2-Chloro-4-nitroaniline

C

3646-57-9, 89103-79-7

bis(4-nitrophenyl)diazene

Conditions
ConditionsYield
With sodium hydroxide; sodium hypochlorite In ethanol at 25℃; for 0.0833333h;A n/a
B 15%
C 9%
60-29-7

diethyl ether

408326-80-7

N,N-dichloro-4-nitro-aniline

99-30-9

4-nitro-2,6-dichloroaniline

697-88-1

4-bromo-2,6-dichloroaniline

99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With nitric acid; acetic acid
13633-34-6

1,3-dichloro-2,5-dinitro-benzene

99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With ethanol; ammonia in der Kaelte;
408326-80-7

N,N-dichloro-4-nitro-aniline

99-30-9

4-nitro-2,6-dichloroaniline

Conditions
ConditionsYield
With hydrogenchloride; diethyl ether
With diethyl ether
With acetic anhydride

2,6-Dichloro-4-nitroaniline Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

2,6-Dichloro-4-nitroaniline Specification

The Benzenamine,2,6-dichloro-4-nitro-, with the CAS registry number 99-30-9, is also known as 2,6-Dichloro-4-nitrobenzenamine. It belongs to the product categories of Intermediates of Dyes and Pigments; Pharmaceutical intermediate. Its EINECS number is 202-746-4. This chemical's molecular formula is C6H4Cl2N2O2 and molecular weight is 207.01. What's more, its systematic name is 2,6-dichloro-4-nitroaniline. Its classification codes are: (1)Agricultural Chemical; (2)Fungicide, bactericide, wood preservative; (3)Mutation data; (4)Tumor data. It should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from oxides, strong acids, heat and fire. It should also be prevented from direct sunlight. It is used as dye intermediates.

Physical properties of Benzenamine,2,6-dichloro-4-nitro- are: (1)ACD/LogP: 3.54; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.54; (4)ACD/LogD (pH 7.4): 3.54; (5)ACD/BCF (pH 5.5): 287.48; (6)ACD/BCF (pH 7.4): 287.48; (7)ACD/KOC (pH 5.5): 2002.05; (8)ACD/KOC (pH 7.4): 2002.05; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 49.06 Å2; (13)Index of Refraction: 1.655; (14)Molar Refractivity: 46.82 cm3; (15)Molar Volume: 127.4 cm3; (16)Polarizability: 18.56×10-24cm3; (17)Surface Tension: 63.8 dyne/cm; (18)Density: 1.624 g/cm3; (19)Flash Point: 149.1 °C; (20)Enthalpy of Vaporization: 56.49 kJ/mol; (21)Boiling Point: 323 °C at 760 mmHg; (22)Vapour Pressure: 0.000269 mmHg at 25°C.

Preparation: this chemical can be prepared by paranitroaniline chloridizing in the mixture of hydrochloric acid and glacial acetic acid.

Uses of Benzenamine,2,6-dichloro-4-nitro-: it can be used to produce 1,2,3-trichloro-5-nitro-benzene. It will need reagents conc. aq. HCl, conc. aq. H2SO4, Cu2Cl2 and solvent acetic acid with the reaction time of 1 hour. The yield is about 47%.

Benzenamine,2,6-dichloro-4-nitro- can be used to produce 1,2,3-trichloro-5-nitro-benzene

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. It has a danger of cumulative effects. You should not breathe dust. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1cc(cc(Cl)c1N)[N+]([O-])=O
(2)Std. InChI: InChI=1S/C6H4Cl2N2O2/c7-4-1-3(10(11)12)2-5(8)6(4)9/h1-2H,9H2
(3)Std. InChIKey: BIXZHMJUSMUDOQ-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
duck LD50 oral > 2gm/kg (2000mg/kg)   Pesticide Manual. Vol. 9, Pg. 265, 1991.
guinea pig LD50 oral 1450mg/kg (1450mg/kg)   Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 343, 1966.
mammal (species unspecified) LD50 unreported 1500mg/kg (1500mg/kg)   "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 87, 1971.
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03022.
mouse LD50 oral 1500mg/kg (1500mg/kg)   Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 343, 1966.
mouse LD50 skin > 5gm/kg (5000mg/kg)   Pesticide Manual. Vol. 9, Pg. 265, 1991.
mouse LD50 unreported 4490mg/kg (4490mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: ATAXIA
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 54(11), Pg. 4, 1989.
rabbit LD50 skin > 2gm/kg (2000mg/kg)   Pesticide Manual. Vol. 9, Pg. 265, 1991.
rat LC50 inhalation > 21600mg/m3/1 (21600mg/m3)   Pesticide Manual. Vol. 9, Pg. 265, 1991.
rat LD50 oral 2400mg/kg (2400mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Office of Toxic Substances Report. Vol. OTS.

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