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2,4-Dichloroaniline

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Name

2,4-Dichloroaniline

EINECS 209-057-8
CAS No. 554-00-7 Density 1.401 g/cm3
PSA 26.02000 LogP 3.15680
Solubility soluble in alcohol, ether Melting Point 59-62°C(lit.)
Formula C6H5Cl2N Boiling Point 242.1 °C at 760 mmHg
Molecular Weight 162.018 Flash Point 100.2 °C
Transport Information UN 3442 6.1/PG 2 Appearance white needle crystal
Safety 28-36/37-45-60-61 Risk Codes 23/24/25-33-50/53
Molecular Structure Molecular Structure of 554-00-7 (2,4-Dichloroaniline) Hazard Symbols ToxicT,DangerousN,IrritantXi
Synonyms

Aniline,2,4-dichloro- (6CI,8CI);2,4-Dichlorobenzenamine;2,4-Dichlorophenylamine;4-Chloro-2-chloroaniline;NSC 8756;o,p-Dichloroaniline;

Article Data 109

2,4-Dichloroaniline Synthetic route

611-06-3

2,4-dichloronitrobenzene

554-00-7

2,4-Dichloroaniline

Conditions
ConditionsYield
With hydrogen In ethanol; water at 25℃; under 760.051 Torr; for 3h; Autoclave;99.9%
With hydrogen In tetrahydrofuran; water at 120℃; under 22502.3 Torr; for 4h; Autoclave;99%
Stage #1: 2,4-dichloronitrobenzene With 2.0%Pt-0.5%Rh/C In methanol for 0.0833333h;
Stage #2: With hydrogen In methanol at 30℃; under 760.051 Torr; for 2.5h; Catalytic behavior; Reagent/catalyst;
98.9%
1965-25-9

1-azido-2,4-dichlorobenzene

554-00-7

2,4-Dichloroaniline

Conditions
ConditionsYield
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 0.166667h; Ambient temperature;97%
With sodium sulfide; water for 0.5h; Reflux;95%
With methanol; samarium; iodine for 6h; Ambient temperature;86%
296778-52-4

tert-butyl (2,4-dichlorophenyl)carbamate

554-00-7

2,4-Dichloroaniline

Conditions
ConditionsYield
With tin(II) trifluoromethanesulfonate In dichloromethane at 20℃; for 2h;95%
106-47-8

4-chloro-aniline

554-00-7

2,4-Dichloroaniline

Conditions
ConditionsYield
With sodium perborate; potassium chloride; sodium vanadate In acetic acid at 20℃; for 2.66667h; Chlorination;93%
13665-50-4

2,2',4,4'-Tetrachloroazobenzene

554-00-7

2,4-Dichloroaniline

Conditions
ConditionsYield
With perchloric acid In isopropyl alcohol; acetonitrile at 25℃; for 0.933333h; pH=2; Inert atmosphere; Irradiation;79%
36984-15-3

2-(2,4-dichlorophenoxy)propanamide

554-00-7

2,4-Dichloroaniline

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 3h; Green chemistry;77%
With potassium hydroxide at 140℃;114.3 mg
120-83-2

2,4-dichlorophenol

554-00-7

2,4-Dichloroaniline

Conditions
ConditionsYield
With potassium carbonate; potassium iodide; Chloroacetamide In N,N-dimethyl-formamide at 90 - 150℃; for 4h; Smiles Aromatic Rearrangement;62%
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / Inert atmosphere; Reflux
2: 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; ammonium carbamate / water; 1,2-dichloro-ethane / 24 h / 33 °C / 760.05 Torr / Sealed tube; Inert atmosphere; Irradiation
View Scheme
95-51-2

2-Chloroaniline

A

554-00-7

2,4-Dichloroaniline

B

608-31-1

2,6-Dichloroaniline

Conditions
ConditionsYield
With chlorine In chlorobenzene at 15℃; for 6h; Solvent; Reagent/catalyst; Temperature;A 60%
B 35%
116278-63-8

N-(4-chlorophenyl)-O-pivaloylhydroxylamine

A

28443-50-7

2-amino-5-chlorophenol

B

554-00-7

2,4-Dichloroaniline

C

116278-66-1

N-(4-chloro-2-hydroxyphenyl)-2,2-dimethylpropanamide

D

106-51-4

p-benzoquinone

Conditions
ConditionsYield
In water; acetonitrile at 40℃; Rate constant; pH=1.0, μ=0.5M; other pH values; other N-aryl-O-pivaloylhydroxylamines;A 3.6%
B 53.2%
C 8.3%
D 3.8%
116278-63-8

N-(4-chlorophenyl)-O-pivaloylhydroxylamine

A

554-00-7

2,4-Dichloroaniline

B

116278-66-1

N-(4-chloro-2-hydroxyphenyl)-2,2-dimethylpropanamide

C

106-51-4

p-benzoquinone

Conditions
ConditionsYield
In water; acetonitrile at 40℃; pH=4.7 (1:1 HOAc/KOAc);A 49.6%
B 26.2%
C 7%

2,4-Dichloroaniline Consensus Reports

Reported in EPA TSCA Inventory.

2,4-Dichloroaniline Specification

This chemical is called 2,4-Dichloroaniline, and its CAS registry number is 554-00-7. With the classification code Mutation data, its product categories are Intermediates of Dyes and Pigments; Chlorobenzene Series; Organics; Amines; AromaticsPesticides & Metabolites; Chemical Class; D; DAlphabetic; DIA - DIC; C2 to C6; Nitrogen Compounds. It should be stored at 0-6°C. Ensure that the surroundings is ventilated and dry. Moreover, this chemical could be obtained by the acetanilide.

Other characteristics of the 2,4-Dichloroaniline can be summarised as followings: (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): 71.32; (6)ACD/BCF (pH 7.4): 71.34; (7)ACD/KOC (pH 5.5): 738.08; (8)ACD/KOC (pH 7.4): 738.32; (9)#H bond acceptors: 1; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 26.02 Å2; (13)Index of Refraction: 1.613; (14)Molar Refractivity: 40.27 cm3; (15)Molar Volume: 115.6 cm3; (16)Polarizability: 15.96×10-24cm3; (17)Surface Tension: 48.3 dyne/cm; (18)Density: 1.401 g/cm3; (19)Flash Point: 100.2 °C; (20)Enthalpy of Vaporization: 47.9 kJ/mol; (21)Boiling Point: 242.1 °C at 760 mmHg; (22)Vapour Pressure: 0.0347 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. Besides, it's very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. Its container must be disposed of as hazardous waste. Avoid releasing it to the environment. Refer to special instructions / safety data sheets.

You can still convert the following datas into molecular structure:
1.SMILES: Clc1cc(Cl)c(N)cc1
2.InChI: InChI=1/C6H5Cl2N/c7-4-1-2-6(9)5(8)3-4/h1-3H,9H2
3.InChIKey: KQCMTOWTPBNWDB-UHFFFAOYAS

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 113mg/kg (113mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 72, Pg. 241, 1913.
mouse LD50 intraperitoneal 400mg/kg (400mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Office of Toxic Substances Report. Vol. OTS,
mouse LD50 oral 400mg/kg (400mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Office of Toxic Substances Report. Vol. OTS,
rat LD50 intraperitoneal 400mg/kg (400mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Office of Toxic Substances Report. Vol. OTS,
rat LD50 oral 1600mg/kg (1600mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Office of Toxic Substances Report. Vol.

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