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242284

Sigma-Aldrich

Aniline

ACS reagent, ≥99.5%

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Synonym(s):
Aminobenzene, Benzenamine
Linear Formula:
C6H5NH2
CAS Number:
62-53-3
Molecular Weight:
93.13
Beilstein:
605631
EC Number:
200-539-3
MDL number:
MFCD00007629
eCl@ss:
39030407
PubChem Substance ID:
24854547
NACRES:
NA.21

grade

ACS reagent

Quality Level

200

vapor density

3.22 (185 °C, vs air)

vapor pressure

0.7 mmHg ( 25 °C)

Assay

≥99.5%

form

liquid

autoignition temp.

1139 °F

expl. lim.

11 %

impurities

Hydrocarbons, passes test
 Nitrobenzene, passes test (lim. ~0.001%)
≤0.01% chlorobenzene

ign. residue

≤0.005%

refractive index

n20/D 1.586 (lit.)

bp

184 °C (lit.)

mp

−6 °C (lit.)

solubility

water: soluble

density

1.022 g/mL at 25 °C (lit.)

SMILES string

Nc1ccccc1

InChI

1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2

InChI key

PAYRUJLWNCNPSJ-UHFFFAOYSA-N

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Application

Aniline is an aromatic primary amine that may be used as a reactant in the synthesis of organic intermediates such as 3-chloro-N-phenyl-pyridin-2-amine, (Z)-methyl 3-(phenylamino)but-2-enoate, 2-iodo-N-phenylbenzamide, 2,4-dichloroquinoline and N-(2-propynyl)aniline.

Biochem/physiol Actions

The acute toxicity of aniline involves its activation in vivo to 4-hydroxyaniline and the formation of adducts with hemoglobin. In erythrocytes, this is associated with the release of iron and the accumulation of methemoglobin and the development of hemolytic anemia and inflammation of the spleen. Tumor formation is often observed in the spleen on prolonged administration.

Physical properties

Material darkens in storage to reddish-brown with no loss in purity.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 2 - Eye Dam. 1 - Muta. 2 - Skin Sens. 1 - STOT RE 1

Target Organs

Blood

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

158.0 °F - closed cup

Flash Point(C)

70 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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Potassium tert-Butoxide Mediated Synthesis of
Phenanthridinone
Bhakuni BS, et al
Organic Syntheses, 90, 164-173 (2013)
Synthesis of caboline
He l, et al
Organic Syntheses, 93, 272-285 (2016)
Synthesis of Tetrasubstituted 1H-Pyrazoles by Coppermediated
Coupling of Enaminones with Nitriles
Suri M and Glorius F
Organic Syntheses, 91, 211-220 (2014)
Synthesis of Quinolines by Electrophilic Cyclization of N-(2-Alkynyl)Anilines: 3-Iodo-4-Phenylquinoline
Chen Y, et al
Organic Syntheses, 89, 294-306 (2012)
The application of fast scan cyclic voltammetry. Mechanistic study of the initial stage of electropolymerization of aniline in aqueous solutions.
Yang H and Bard AJ.
Journal of Electroanalytical Chemistry, 339(1), 423-449 (1992)
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