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3-Chloroaniline

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Name

3-Chloroaniline

EINECS 203-581-0
CAS No. 108-42-9 Density 1.216
PSA 26.02000 LogP 2.50340
Solubility Water solubility: 6.8 g/L (20 °C) Melting Point -11--9 °C(lit.)
Formula C6H6ClN Boiling Point 227.8 °C at 760 mmHg
Molecular Weight 127.573 Flash Point 123.9 °C
Transport Information UN 2019 6.1/PG 2 Appearance clear pale yellow to brown liquid
Safety 28-36/37-45-60-61-28A Risk Codes 23/24/25-33-50/53
Molecular Structure Molecular Structure of 108-42-9 (3-Chloroaniline) Hazard Symbols ToxicT,DangerousN
Synonyms

Aniline,m-chloro- (8CI);1-Amino-3-chlorobenzene;3-Amino-1-chlorobenzene;3-Chloro-1-aminobenzene;3-Chlorobenzenamine;3-Chlorophenylamine;5-Chloroaniline;Fast Orange GC Base;NSC 17581;Orange GC base;m-Aminochlorobenzene;m-Chloroaniline;m-Chlorophenylamine;

Article Data 289

3-Chloroaniline Synthetic route

121-73-3

3-Chloronitrobenzene

108-42-9

3-chloro-aniline

Conditions
ConditionsYield
With 2 weight% platinum on carbon; ethanol at 100℃; under 7500.75 Torr; for 8h; Autoclave;100%
With hydrogen In ethanol at 20℃; under 7500.75 Torr; for 8h; Catalytic behavior; Sealed tube;100%
With hydrazine hydrate In ethanol; water at 80℃; for 1h; chemoselective reaction;100%
95-76-1

m,p-dichloroaniline

108-42-9

3-chloro-aniline

Conditions
ConditionsYield
100%
608-27-5

2,3-dichloroaniline

108-42-9

3-chloro-aniline

Conditions
ConditionsYield
100%
7440-05-3

palladium

636-30-6

2,4,5-trichloroaniline

108-42-9

3-chloro-aniline

Conditions
ConditionsYield
With hydrogenchloride; potassium iodide98.2%
3296-06-8

1-azido-3-chlorobenzene

108-42-9

3-chloro-aniline

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran for 2h; Ambient temperature;98%
Stage #1: 1-azido-3-chlorobenzene With hydrazine hydrate for 0.166667h; Inert atmosphere;
Stage #2: for 10h; Irradiation; chemoselective reaction;
90%
With zinc(II) tetrahydroborate In 1,2-dimethoxyethane for 3.5h; Ambient temperature;89%
634-91-3

3,4,5-trichloroaniline

A

108-42-9

3-chloro-aniline

B

626-43-7

3,5-Dichloroaniline

Conditions
ConditionsYield
A 97.9%
B n/a
608-27-5

2,3-dichloroaniline

95-50-1

1,2-dichloro-benzene

95-76-1

m,p-dichloroaniline

108-42-9

3-chloro-aniline

Conditions
ConditionsYield
With HI; hydrogen iodide96.5%
concentrated aqueous sodium hydroxide

concentrated aqueous sodium hydroxide

608-27-5

2,3-dichloroaniline

108-95-2

phenol

108-42-9

3-chloro-aniline

Conditions
ConditionsYield
With hydrogen; palladium/charcoal In tantalum; water; toluene96%
625-99-0

3-iodochlorobenzene

108-42-9

3-chloro-aniline

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide; C17H14N2O3; potassium hydroxide In ethanol at 60℃; for 24h; Schlenk technique; Inert atmosphere;96%
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide In dimethyl sulfoxide at 25℃; for 24h; Inert atmosphere; Sealed tube;90%
With copper(l) iodide; tetra(n-butyl)ammonium hydroxide; ammonia In water at 25℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;89%
108-37-2

1-bromo-3-chlorobenzene

108-42-9

3-chloro-aniline

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h;93%
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; Sealed tube;93%
With ammonium hydroxide; copper(l) iodide; 2,2-[μ-(N,N'-piperazindiyl)dimethyl]-bis(4,6-di-tert-butyl-phenol) In water at 120℃; for 12h;85%

3-Chloroaniline Chemical Properties

Molecular Formula: C6H6ClN
Formula Weight: 127.57 
EINECS: 203-581-0 
Index of Refraction: 1.598
Molar Refractivity: 35.38 cm3
Molar Volume: 103.6 cm3
Surface Tension: 45.3 dyne/cm
Density: 1.23 g/cm3
Flash Point: 123.9 °C
Enthalpy of Vaporization: 46.43 kJ/mol
Boiling Point: 227.8 °C at 760 mmHg
Vapour Pressure: 0.0762 mmHg at 25 °C
Melting point: -11--9 °C(lit.)
Water solubility: 6.8 g/L (20 °C)
Appearance: Clear pale yellow to brown liquid
Structure of 3-Chloroaniline (CAS NO.108-42-9):
                      
IUPAC Name: 3-Chloroaniline
Canonical SMILES: C1=CC(=CC(=C1)Cl)N
InChI: InChI=1S/C6H6ClN/c7-5-2-1-3-6(8)4-5/h1-4H,8H2
InChIKey: PNPCRKVUWYDDST-UHFFFAOYSA-N
Product Category of 3-Chloroaniline (CAS NO.108-42-9): Chlorobenzene Series;Amines;Nitrogen Compounds;CAlphabetic;Chemical Class;European Community: ISO and DIN

3-Chloroaniline Uses

 3-Chloroaniline (CAS NO.108-42-9) is used as an intermediate in the production of a number of products, including agricultural chemicals, azo dyes and pigments, bactericide or biocide and pharmaceuticals.

3-Chloroaniline Production

In the presence of ferrous sulfate, 3-CHLOROANILINE (108-42-9) is synthesized from m-nitrochlorobenzne by condensation of iron powder.

3-Chloroaniline Toxicity Data With Reference

1.    

mmo-asn 200 mg/L

    CJMIAZ    Canadian Journal of Microbiology. 16 (1970),369.
2.    

orl-rat LD50:256 mg/kg

    GISAAA    Gigiena i Sanitariya. 31 (12)(1966),6.
3.    

skn-rat LD50:250 mg/kg

    85GMAT    Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow.: USSR, Centre of International Projects, GKNT,1982,34.
4.    

orl-mus LD50:334 mg/kg

    GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 13 (5)(1969),29.
5.    

ihl-mus LC50:550 mg/m3/4H

    85GMAT    Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow.: USSR, Centre of International Projects, GKNT,1982,34.
6.    

ivn-dog LDLo:50 mg/kg

    AEPPAE    Naunyn-Schmiedebergs Archiv fuer Experimentelle Pathologie und Pharmakologie. 244 (1963),387.
7.    

skn-cat LD50:223 mg/kg

    GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 13 (5)(1969),29.
8.    

scu-cat LDLo:125 mg/kg

    AHBAAM    Archiv fuer Hygiene und Bakteriologie. 110 (1933),12.
9.    

orl-gpg LD50:250 mg/kg

    GISAAA    Gigiena i Sanitariya. 31 (12)(1966),6.

 3-Chloroaniline (CAS NO.108-42-9) hasn't been listed as a carcinogen by NTP, IARC, ACGIH, or CA Prop 65. And the toxicological properties have not been fully investigated. You can see actual entry in RTECS for complete information.

3-Chloroaniline Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

3-Chloroaniline Safety Profile

Safety: DANGER: POISON, irritates skin, eyes, lungs
Hazard Codes: ToxicT,DangerousN
Risk Statements: 23/24/25-33-50/53 (Toxic by inhalation, in contact with skin and if swallowed; Danger of cumulative effects; Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment)
Safety Statements: 28-36/37-45-60-61-28A (After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer);
Poison by ingestion, skin contact, subcutaneous, and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl and NOx. See also ANILINE DYES.

3-Chloroaniline Standards and Recommendations

ASSAY: 99.0% min
WATER: 0.3% max

3-Chloroaniline Specification

 3-Chloroaniline , its cas register number is 108-42-9. It also can be called 1-Amino-3-chlorobenzene ; m-Aminochlorobenzene ; 3-Chlorophenylamine ; Fast Orange GC base ; and 3-Chlorobenzenamine . It should be stored in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, 3-Chloroaniline (CAS NO.108-42-9) darkens on exposure to light and air. It is not compatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides, chloroformates, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: Hydrogen chloride, nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.

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