Name: 4-Chloro-2-nitroaniline
SKU: 89-63-4

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Basic Information

Molecular Structure:
CAS No.:	89-63-4
Name:	4-Chloro-2-nitroaniline

Formula:	C₆H₅ClN₂O₂
Molecular Weight:	172.571
Synonyms:	Aniline,4-chloro-2-nitro- (8CI);(4-Chloro-2-nitrophenyl)amine;1-Amino-2-nitro-4-chlorobenzene;2-Nitro-4-chloroaniline;4-Chloro-2-nitrobenzenamine;Daito Red Base 3GL;Devol Red F;Diazo Fast Red 3GL;Fast Red 3GL Base;Fast Red3GL Special Base;Hiltonil Fast Red 3GL Base;Mitsui Red 3GL Base;NSC 3546;NaphtoelanFast Red 3GL Base;PCON;PCONA;Red Base Ciba VI;Red Base Irga VI;Shinnippon Fast Red 3GL Base;p-Chloro-o-nitroaniline;
EINECS:	201-925-4
Density:	1.494 g/cm³
Melting Point:	115-119 °C
Boiling Point:	308.8 °C at 760 mmHg
Flash Point:	140.5 °C
Solubility:	insoluble in water
Appearance:	bright orange powder
Hazard Symbols:	T+, N, T
Risk Codes:	26/27/28-33-51/53
Safety:	28-36/37-45-61-28A
Transport Information:	UN 2237 6.1/PG 3
PSA:	71.84000
LogP:	2.93480

Synthetic route

: 88-74-4
2-nitro-aniline

: 89-63-4
4-Chloro-2-nitroaniline

Conditions

Conditions	Yield
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; for 0.0833333h; Green chemistry;	99.2%
With copper dichloride; 1-hexyl-3-methylimidazol-1-ium chloride at 40℃; for 16h; regioselective reaction;	85%
With N-chloro-succinimide In acetonitrile for 10h; Heating;	57%
Multi-step reaction with 2 steps 1: diethyl ether; hypochlorous acid / 20 °C 2: hydrochloric acid; diethyl ether / -20 °C View Scheme

: 610-40-2
3,4-dinitro-chlorobenzene

: 89-63-4
4-Chloro-2-nitroaniline

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol; water at 20℃; for 4h; Green chemistry;	90%

: 106-47-8
4-chloro-aniline

: 89-63-4
4-Chloro-2-nitroaniline

Conditions

Conditions	Yield
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 3h;	92%
Multi-step reaction with 3 steps 1: acetic acid / 0.25 h / Heating 2: 60percent nitric acid, conc. sulfuric acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min 3: conc. sulfuric acid / 0.25 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane 2: nitric acid; acetic anhydride / dichloromethane 3: hydrogenchloride / water / Reflux View Scheme

: N-(4-chloro-2-nitrophenyl) pyrimidin-2-amine

: 89-63-4
4-Chloro-2-nitroaniline

Conditions

Conditions	Yield
Stage #1: N-(4-chloro-2-nitrophenyl) pyrimidin-2-amine With triethylsilane; trifluoroacetic acid at 50℃; Inert atmosphere; Stage #2: With acetic acid; hydrazine In methanol at 20℃; Inert atmosphere; regioselective reaction;	80%

: 108-42-9
3-chloro-aniline

: 89-63-4
4-Chloro-2-nitroaniline

Conditions

Conditions	Yield
With nitric acid In sulfuric acid; acetic acid at 20 - 25℃; for 10.5h; Temperature;

: 121-73-3
3-Chloronitrobenzene

A: 769-11-9
2-chloro-6-nitroaniline

B: 89-63-4
4-Chloro-2-nitroaniline

C: 121-87-9
2-Chloro-4-nitroaniline

Conditions

Conditions	Yield
With 2,4,6-trichlorosulfenamide; potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.333333h;	A 26% B 7% C 38%
With O-Methylhydroxylamin; potassium tert-butylate; copper(l) chloride In N,N-dimethyl-formamide for 1h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With potassium tert-butylate; N,N,N-trimethylhydrazinium iodide In dimethyl sulfoxide Ambient temperature; Yield given. Yields of byproduct given;
With O-Methylhydroxylamin; potassium tert-butylate; copper(l) chloride In N,N-dimethyl-formamide at 20℃; Substitution; Amination; Title compound not separated from byproducts;

...Expand

: 52010-24-9
N-(2-nitro-4-chlorophenyl)benzamide

: 89-63-4
4-Chloro-2-nitroaniline

Conditions

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 12h;	99%

: 881-51-6
N-(4-chloro-2-nitrophenyl)-acetamide

: 89-63-4
4-Chloro-2-nitroaniline

Conditions

Conditions	Yield
With sulfuric acid
With hydrogenchloride
With sodium methylate

: 1516-58-1
o-azidonitrobenzene

A: 769-11-9
2-chloro-6-nitroaniline

B: 88-74-4
2-nitro-aniline

C: 89-63-4
4-Chloro-2-nitroaniline

Conditions

Conditions	Yield
With boron trichloride In benzene Ambient temperature;	A 17% B 3% C 64%
With boron trichloride In benzene at 50℃; for 6h;	A 3% B 3% C 64%
With boron trichloride In benzene at 50℃; for 6h;	A 17% B 3% C 64%

...Expand

: 539-03-7
N-(4-chlorophenyl)acetamide

: 89-63-4
4-Chloro-2-nitroaniline

Conditions

Conditions	Yield
With nitric acid Kochen des Reaktionsproduktes mit Natronlauge;
With nitric acid at -10℃; durch Erwaermen des Reaktionsprodukts mit etwas konz. Schwefelsaeure auf 100grad;
Multi-step reaction with 2 steps 1: 60percent nitric acid, conc. sulfuric acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min 2: conc. sulfuric acid / 0.25 h / 100 °C View Scheme

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The IUPAC name of Kayaku Fast Red 3GL Base is 4-chloro-2-nitroaniline. With the CAS registry number 89-63-4, it is also named as Azofix Red 3GL Salt. The product's categories are Intermediates of Dyes and Pigments; Anilines, Aromatic Amines and Nitro Compounds; Organics. It is bright orange powder which is insoluble in water, soluble in alcohol, ether and acetic acid, and slightly soluble in crude gasoline. It is also stable, combustible and incompatible with strong oxidizing agents. When heated to decomposition it emits toxic vapors of NO_x and Cl⁻. What's more, this chemical can form explosive products on reaction with nitric acid. So the storage environment should be well-ventilated, low-temperature and dry. Keep Kayaku Fast Red 3GL Base separate from raw materials of food.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.74; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.74; (4)ACD/LogD (pH 7.4): 2.74; (5)ACD/BCF (pH 5.5): 71.65; (6)ACD/BCF (pH 7.4): 71.65; (7)ACD/KOC (pH 5.5): 740.59; (8)ACD/KOC (pH 7.4): 740.59; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.646; (13)Molar Refractivity: 41.92 cm³; (14)Molar Volume: 115.5 cm³; (15)Polarizability: 16.62×10^-24 cm³; (16)Surface Tension: 62.2 dyne/cm; (17)Enthalpy of Vaporization: 54.95 kJ/mol; (18)Vapour Pressure: 0.000667 mmHg at 25°C; (19)Exact Mass: 172.003955; (20)MonoIsotopic Mass: 172.003955; (21)Topological Polar Surface Area: 71.8; (22)Heavy Atom Count: 11; (23)Complexity: 159.

Preparation of Kayaku Fast Red 3GL Base: It can be obtained by forcing ammonolysis of 2,5-Dichloronitrobenzene.

Uses of Kayaku Fast Red 3GL Base: It is used in the production of yellow pigment 10G, disperse yellow 211, UV absorber UV-326 and so on. It is not only used in dyeing cotton and printing cotton, but also used for dyeing of viscose fiber, silk and polyester. What's more, it can react with sulfuric acid dimethyl ester to get 4-chloro-N-methyl-2-nitro-aniline. This reaction which is a kind of methylation needs reagents NaOH, Bu₄NHSO₄and solvent toluene, H₂O at temperature of 20 °C. The yield is 100%.

When you are using this chemical, please be cautious about it as the following:
It is very toxic by inhalation, in contact with skin and if swallowed. And it has danger of cumulative effects. Wha's more, this chemical is also toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must wear suitable protective clothing and gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) Avoid release to the environment. Refer to special instructions / safety data sheets.

People can use the following data to convert to the molecule structure.
1. SMILES:Clc1cc([N+]([O-])=O)c(N)cc1
2. InChI:InChI=1/C6H5ClN2O2/c7-4-1-2-5(8)6(3-4)9(10)11/h1-3H,8H2
3. InChIKey:PBGKNXWGYQPUJK-UHFFFAOYAL

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LD50	oral	3gm/kg (3000mg/kg)	BEHAVIORAL: GENERAL ANESTHETIC	National Technical Information Service. Vol. OTS0536149,
mouse	LD50	intraperitoneal	200mg/kg (200mg/kg)		Office of Toxic Substances Report. Vol. OTS,
mouse	LD50	intravenous	63mg/kg (63mg/kg)		"Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 6, Pg. 139, 1954.
mouse	LD50	oral	800mg/kg (800mg/kg)		Office of Toxic Substances Report. Vol. OTS,
rat	LD50	intraperitoneal	200mg/kg (200mg/kg)		Office of Toxic Substances Report. Vol. OTS,
rat	LD50	oral	400mg/kg (400mg/kg)		Office of Toxic Substances Report. Vol. OTS,

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Consensus Reports

Specification