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Basic Information
CAS No.: 97-02-9
Name: 2,4-Dinitroaniline
Article Data: 165
Molecular Structure:
Molecular Structure of 97-02-9 (2,4-Dinitroaniline)
Formula: C6H5N3O4
Molecular Weight: 183.123
Synonyms: Aniline,2,4-dinitro- (8CI);1-Amino-2,4-dinitrobenzene;2,4-Dinitrobenzenamine;NSC 8731;
EINECS: 202-553-5
Density: 1.586 g/cm3
Melting Point: 177 °C
Boiling Point: 400.6 °C at 760 mmHg
Flash Point: 196.1 °C
Solubility: water: 0.06 g/L (20 °C)
Appearance: yellow crystalline solid
Hazard Symbols: VeryT+,DangerousN
Risk Codes: 26/27/28-33-51/53
Safety: 28-36/37-45-61-28A
Transport Information: UN 1596 6.1/PG 2
PSA: 117.66000
LogP: 2.71280
Synthetic route
89-02-1

2,4-dinitrobenzenesulfonic acid

97-02-9

2,4-Dinitroanilin

Conditions
ConditionsYield
With ammonium hydroxide In methanol at 70℃; for 0.25h;100%
839-93-0

1-(2,4-dinitrophenyl)piperidine

97-02-9

2,4-Dinitroanilin

Conditions
ConditionsYield
With ammonium hydroxide In methanol at 70℃; for 12h;100%
97-00-7

1-chloro-2,4-dinitro-benzene

97-02-9

2,4-Dinitroanilin

Conditions
ConditionsYield
With ammonium hydroxide In formamide at 85℃; under 3000.2 - 3750.3 Torr; for 4h;96%
With 2,2,2-trifluoroacetamide; potassium carbonate; tetrabutylammomium bromide In N,N-dimethyl-formamide at 80℃; for 2h;95%
With copper(ll) sulfate pentahydrate; oxygen; potassium carbonate; formamide at 150 - 160℃; for 2.5h;56%
7474-11-5

1-(2,4-dinitrophenyl)-3,5-dimethylpyrazole

A

67-51-6

3,5-dimethyl-1H-pyrazole

B

97-02-9

2,4-Dinitroanilin

Conditions
ConditionsYield
at 165 - 175℃;A n/a
B 96%
137353-85-6

N-tert-butyl-α-(3-aminophenyl)nitrone

4185-69-7

1-(2,4-dinitrophenyl)-pyridinium chloride

A

1176727-65-3

N-tert-butyl-α-[3-(pyrid-1'-yl)phenyl]nitrone chloride

B

97-02-9

2,4-Dinitroanilin

Conditions
ConditionsYield
In methanol for 18h; Zincke reaction; Inert atmosphere; Reflux;A 96%
B n/a
6075-97-4

1‐(2,4‐dinitrophenyl)‐3,4,5‐trimethyl‐1H‐pyrazole

A

5519-42-6

3,4,5-Trimethylpyrazole

B

97-02-9

2,4-Dinitroanilin

Conditions
ConditionsYield
at 165 - 175℃;A n/a
B 94%
53406-00-1

3-carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride

371-40-4

4-fluoroaniline

A

87384-50-7

3-Carbamoyl-1-(4-fluoro-phenyl)-pyridinium; chloride

B

97-02-9

2,4-Dinitroanilin

Conditions
ConditionsYield
In methanolA 80%
B n/a
109-73-9

N-butylamine

97-00-7

1-chloro-2,4-dinitro-benzene

A

13059-86-4

2,4-dinitro-N-butylaniline

B

N-butyl-3-chloro-2,6-dinitroaniline

C

97-02-9

2,4-Dinitroanilin

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 10℃; Electrolysis;A 80%
B 15%
C 5%
709-49-9

1-iodo-2,4-dinitrobenzene

97-02-9

2,4-Dinitroanilin

Conditions
ConditionsYield
With acetamidine hydrochloride; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 20h; Inert atmosphere; Green chemistry;78%
With ethanol; ammonia im Sonnenlicht;
3886-69-9

(R)-1-phenyl-ethyl-amine

33107-14-1

2-(2,4-dinitrophenyl)-isoquinolinium chloride

A

(+)-2-[(1R)-1-phenethyl]isoquinolinium chloride

B

97-02-9

2,4-Dinitroanilin

Conditions
ConditionsYield
In butan-1-ol for 15h; Heating;A 77%
B n/a
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Chemistry

Chemical Name: 2,4-Dinitroaniline
IUPAC NAME: 2,4-dinitroaniline
CAS No.: 97-02-9
EINECS: 202-553-5
RTECS: BX9100000
RTECS Class: Agricultural Chemical and Pesticide; Mutagen; Reproductive Effector; Primary Irritant
EC Class: Very toxic; Danger of cumulative effects; Dangerous for the Environment
Molecular Formula: C6H5N3O4
Molecular Weight: 183.12 g/mol
Density: 1.586 g/cm3
Melting Point: 177 °C
Flash Point: 196.1 °C
Boiling Point: 400.6 °C at 760 mmHg
2,4-DINITROANILINE(97-02-9) is stable under normal temperatures and pressures.but incompatible with oxidizing materials, vigorous reaction with Chlorine + Hydrochloric Acid evolves gases.and the yellow needle-like crystals is not dissolve in water, slightly soluble in ethanol, soluble in hot hydrochloric acid.Following is the structure of 2,4-DINITROANILINE(97-02-9):

                       
The chemical synonymous of 2,4-DINITROANILINE(97-02-9) are 1-Amino-2,4-dinitrobenzene;2,4-Dinitraniline;2,4-Dinitroaminobenzene;2,4-Dinitroanilin;2,4-dinitro-anilin;2,4-Dinitroanilina;2,4-Dinitrobenzamine;2,4-DINITROANILINE.

Uses

2,4-DINITROANILINE(97-02-9) is used for the manufacture of azo dyes and disperse dyes, but also can be used as printing ink, toner and Preparation of preservatives.and it is an intermediate for disperse dyes, neutral dyes, sulfur dyes, organic pigments.

Production

Product Categories about 2,4-DINITROANILINE(97-02-9) are Intermediates of Dyes and Pigments;Anilines, Aromatic Amines and Nitro Compounds;C2 to C6;Nitrogen Compounds;Alpha Sort;Amines;Analytical Standards;AromaticsChemical Class;AromaticsVolatiles/ Semivolatiles;Chemical Class;D;DAlphabetic;DID - DINAnalytical Standards;Nitro Compounds.

Toxicity Data With Reference

1.   

eye-rbt 500 mg/24H MLD

   28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,132.
2.   

mmo-sat 10 µg/plate

   ENMUDM    Environmental Mutagenesis. 5 (Suppl 1)(1983),3.
3.   

mma-sat 2 µg/plate

   MUREAV    Mutation Research. 67 (1979),1.
4.   

orl-rat LD50:285 mg/kg

   TSCAT*    Office of Toxic Substances Report. (U.S. Environmental Protection Agency, Office of Toxics Substances, 401M Street SW, Washington, DC 20460) OTS 206512 .
5.   

ipr-rat LDLo:250 mg/kg

   NCNSA6    National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. 5 (1953),32.
6.   

orl-mus LD50:370 mg/kg

   GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 25 (8)(1981),50.
7.   

ipr-mus LDLo:400 mg/kg

   JAPMA8    Journal of the American Pharmaceutical Association, Scientific Edition. 48 (1959),419.
8.   

orl-gpg LD50:1050 mg/kg

   GISAAA    Gigiena i Sanitariya. 47 (10)(1982),15.
guinea pigLD50oral1050mg/kg (1050mg/kg) Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 47(10), Pg. 15, 1982.
mouseLD50oral370mg/kg (370mg/kg) Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(8), Pg. 50, 1981.
mouseLDLointraperitoneal400mg/kg (400mg/kg) Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 48, Pg. 419, 1959.
ratLD50oral285mg/kg (285mg/kg) Office of Toxic Substances Report. Vol. OTS,
ratLDLointraperitoneal250mg/kg (250mg/kg) National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 32, 1953.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Poison by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. Mutation data reported. An eye irritant. Combustible and explosive when exposed to heat or flame; can react with oxidizing materials. To fight fire, use CO2, dry chemical. Mixtures with charcoal ignite at 350°C. Vigorous reaction with chlorine + hydrochloric acid evolves gases. When heated to decomposition it emits highly toxic fumes of NOx.
Hazard Codes:
    T+: Very toxic
    N: Dangerous for the environment  
Risk Statements about 2,4-DINITROANILINE(97-02-9):
    R33 Danger of cumulative effects.
    R26/27/28: Very toxic by inhalation, in contact with skin and if swallowed.
    R51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic
Safety Statements  about 2,4-DINITROANILINE(97-02-9):
    S28 After contact with skin, wash immediately with plenty of soap-suds.
    S45 In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
    S61 Avoid release to the environment. Refer to special instructions / safety data sheets.
    S36/37: Wear suitable protective clothing and gloves.
    S28A After contact with skin, wash immediately with plenty of water.
Health Hazard: May cause headache, nausea, stupor. Irritating to skin and mucous membrane.

Specification

1. Storage: Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.
2. Handling: Avoid ingestion and inhalation. Avoid contact with eyes, skin, and clothing. Wash hands before eating. Use only in a well ventilated area. Minimize dust generation and accumulation. Wash clothing before reuse.
3. Personal Protection: Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure.
4. Fire Fighting: Wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. To extinguish fire, use water fog, dry chemical, carbon dioxide, or regular foam.
5. Reactivity Profile: 2,4-Dinitroaniline may decompose violently at elevated temperatures. 2,4-Dinitroaniline can react with oxidizing materials, i.e. chlorine/hydrochloric acid. . In mixture with powdered charcoal ignited upon heating, [Cahiers, 1980, (99), 278].