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Sigma-Aldrich

Aniline

ACS reagent, ≥99.5%

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Synonym(s):
Aminobenzene, Benzenamine
Linear Formula:
C6H5NH2
CAS Number:
Molecular Weight:
93.13
Beilstein/REAXYS Number:
605631
EC Number:
MDL number:
UNSPSC Code:
12352100
eCl@ss:
39030407
PubChem Substance ID:
NACRES:
NA.21

grade

ACS reagent

Quality Level

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.

signalword

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

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Synthesis of Tetrasubstituted 1H-Pyrazoles by Coppermediated
Coupling of Enaminones with Nitriles
Suri M and Glorius F
Organic Syntheses, 91, 211-220 (2014)
Potassium tert-Butoxide Mediated Synthesis of
Phenanthridinone
Bhakuni BS, et al
Organic Syntheses, 90, 164-173 (2013)
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)
Atsuhiro Tanaka et al.
Chemical communications (Cambridge, England), 49(25), 2551-2553 (2013-02-21)
A functionalized plasmonic Au/TiO2 photocatalyst with an Ag co-catalyst was successfully prepared by the combination of two types of photodeposition methods, and it quantitatively converted nitrobenzene and 2-propanol to aniline and acetone under irradiation of visible light.

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