| Identification | More | [Name]
2-Chloroaniline | [CAS]
95-51-2 | [Synonyms]
1-AMINO-2-CHLOROBENZENE
2-CHLOROANILINE
2-CHLOROBENZENAMINE
2-CHLOROPHENYLAMINE
AKOS BBS-00003671
FAST YELLOW GC BASE
OCA
O-CHLOROANILINE
ORTHO-CHLOROANILINE
1,2-aminochlorobenzene
2-chloro-benzenamin
Aniline, o-chloro-
Azoic diazo component 44, base
Benzenamine, 2-chloro-
Benzenamine,2-chloro-
Benzeneamine,2-chloro-
o-Aminochlorobenzene
o-Aminochloro-benzene
o-Chloraniline
o-Chloroaminobenzene | [EINECS(EC#)]
202-426-4 | [Molecular Formula]
C6H6ClN | [MDL Number]
MFCD00007656 | [Molecular Weight]
127.57 | [MOL File]
95-51-2.mol |
| Chemical Properties | Back Directory | [Appearance]
clear pale yellow to brown liquid | [Melting point ]
0-3 °C
| [Boiling point ]
208-210 °C(lit.)
| [density ]
1.213 g/mL at 25 °C(lit.)
| [vapor density ]
4.41 (vs air)
| [vapor pressure ]
0.5 hPa (20 °C) | [refractive index ]
n20/D 1.589
| [Fp ]
98 °C
| [storage temp. ]
2-8°C | [solubility ]
water: soluble5.13g/L at 20°C | [form ]
Liquid | [pka]
2.65(at 25℃) | [color ]
Clear pale yellow to brown | [Odor]
Characteristic odour | [explosive limit]
2.4-14.2%(V) | [Water Solubility ]
5.13 g/L (20 ºC) | [Merck ]
14,2118 | [BRN ]
606077 | [Dielectric constant]
13.4 | [LogP]
1.72 at 20℃ and pH6-8 | [Uses]
Dye intermediate, standards for colorimetric
apparatus, manufacture of petroleum solvents and
fungicides. | [CAS DataBase Reference]
95-51-2(CAS DataBase Reference) | [NIST Chemistry Reference]
o-Chloroaniline(95-51-2) | [EPA Substance Registry System]
95-51-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,N,F | [Risk Statements ]
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R33:Danger of cumulative effects.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R11:Highly Flammable. | [Safety Statements ]
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 2019 6.1/PG 2
| [WGK Germany ]
2
| [RTECS ]
BX0525000
| [F ]
8-10-23 | [Autoignition Temperature]
>500 °C | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29214210 | [Safety Profile]
Poison by skin contact,
ingestion, and subcutaneous routes.
Mutation data reported. When heated to
decomposition it emits toxic fumes of Cl
and NOx. See also ANILINE DYES. | [Hazardous Substances Data]
95-51-2(Hazardous Substances Data) |
| Hazard Information | Back Directory | [General Description]
Clear amber liquid with an amine odor. Occurs in both alpha and beta forms. | [Reactivity Profile]
O-CHLOROANILINE(95-51-2) is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. | [Air & Water Reactions]
Sensitive to prolonged exposure to air and darkens on exposure to light. Insoluble in water. | [Hazard]
Toxic by ingestion. | [Fire Hazard]
This chemical is combustible. | [Description]
properties:m-isomerColorless to yellow liquid that may turn brown on exposureto air. Molecular weight=127.57; Specific gravity(H2O:1)=1.216; Boiling point (decomposes)=230℃;Melting point=-11℃; Vapor pressure=,0.1 mmHg at20℃; Flash point=118℃(cc); Autoignitiontemperature=.540℃. Slight solubility in water;solubility=0.6%.o-isomerColorless to yellow liquid that may turn brown on exposureto air. Molecular weight=127.57; Specific gravity(H2O:1)=1.21; Boiling point=208.7℃; Meltingpoint=-2℃; Flash point=108℃; Autoignitiontemperature=.500℃; solubility in water=0.5% at 20℃.p-isomer (see also P:0400)The p-isomer is a colorless to pale yellow crystalline solid.Molecular weight=127.6; Specific gravity (H2O:1)=1.4;Boiling point=232℃; Melting point=69.5-72.5℃; Vaporpressure=0.015 mmHg at 20℃; Flash point=120-123℃(oc); Autoignition temperature=685℃. HazardIdentification (based on NFPA 704 M Rating System): p-isomer Health 3, Flammability 1, Reactivity 0. Soluble in hotwater; solubility (cold)=0.4% at 20℃. | [Chemical Properties]
clear pale yellow to brown liquid | [Preparation]
The synthesis method of 2-chloroaniline is to reflux 2-nitrochlorobenzene with iron filings, dilute hydrochloric acid and water for 6~8h, distill to get crude product, and then distill to get finished product. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 39, p. 2718, 1974 DOI: 10.1021/jo00932a011
Tetrahedron Letters, 26, p. 3277, 1985 DOI: 10.1016/S0040-4039(00)98171-1 | [Potential Exposure]
RTECS Compound Description (mand o-isomers): Tumorigen, Mutagen (p-isomer):Tumorigen, Mutagen, Primary Irritant. Chloroanilines areused to make dyes, other chemicals, insecticides, and manyother industrial products. | [First aid]
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Medical observation is recommended.Note to physician: Treat for methemoglobinemia.Spectrophotometry may be required for precise determination of levels of methemoglobinemia in urine. | [storage]
Color Code—Blue: Health Hazard/Poison (p-isomer): Store in a secure poison location. Prior to workingwith chloroaniline you should be trained on its proper handling and storage. Store in tightly closed containers in acool, well-ventilated area away from oxidizers (such asperchlorates, peroxides, permanganates, chlorates, andnitrates), since violent reactions occur. A regulated, markedarea should be established where this chemical is handled,used, or stored in compliance with OSHA Standard1910.1045. | [Shipping]
Chloroanilines are required by DOT to carry a“POISONOUS/TOXIC MATERIALS” label. They fall inHazard Class 6.1 and Packing Group II. | [Purification Methods]
Free it from small amounts of the p-isomer by dissolving in one equivalent of H2SO4 and steam distilling. The p-isomer remains behind as the sulfate. [Sidgwick & Rubie J Chem Soc 1013 1921.] An alternative method is to dissolve it in warm 10% HCl (11mL/g of amine) and on cooling, o-chloroaniline hydrochloride separates out. The latter can be recrystallised until the acetyl derivative has a constant melting point (m 90o). (In this way, yields are better than via the recrystallisation of the picrate from EtOH or of the acetyl derivative from pet ether.) [King & Orton J Chem Soc 1377 1911]. [Beilstein 12 III 1281, 12 IV 1115.] | [Incompatibilities]
Contact with strong oxidizers may causefire and explosions. The aqueous solution of the m-isomeris a weak base. Incompatible with strong acids, organicanhydrides, isocyanates, aldehydes. |
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