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Sigma-Aldrich

4-Bromoaniline

97%

Synonym(s):

1-Amino-4-bromobenzene, p-Bromoaniline

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About This Item

Linear Formula:
BrC6H4NH2
CAS Number:
106-40-1
Molecular Weight:
172.02
Beilstein:
742031
EC Number:
203-393-9
MDL number:
MFCD00007822
UNSPSC Code:
12352100
PubChem Substance ID:
24846426

Quality Level

200

Assay

97%

form

solid

mp

56-62 °C (lit.)

SMILES string

Nc1ccc(Br)cc1

InChI

1S/C6H6BrN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2

InChI key

WDFQBORIUYODSI-UHFFFAOYSA-N

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Application

4-Bromoaniline can be used as a starting material for the preparation of:
  • Sharpless asymmetric ligands for dihydroxylation of alkenes.
  • Chemical intermediates such as 4-bromophenyl azide , 4-bromonitrosobenzene , N-(4-bromophenyl)-4-methylbenzenesulfonamide , and ethyl 4-(4-(4-methylphenylsulfonamido)phenyl)butanoate.

It is also used in the surface functionalization of carbon nanotubes via preparation of 4-bromo benzenediazonium derivatives.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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A triazine core for a new class of Sharpless asymmetric dihydroxylation ligands
McNamara CA, et al.
Tetrahedron Letters, 45(46), 8527-8529 (2004)
Thermal azide-alkene cycloaddition reactions: straightforward multi-gram access to δ 2-1, 2, 3-triazolines in deep eutectic solvents
Sebest F, et al.
Green Chemistry, 20(17), 4023-4035 (2018)
Photoactive boron-nitrogen-carbon hybrids: from azo-borazines to polymeric materials
Oubaha H, et al.
The Journal of Organic Chemistry, 20(17), 4023-4035 (2019)
Solvent-free functionalization of carbon nanotubes
Dyke CA and Tour JM
Journal of the American Chemical Society, 125(5), 1156-1157 (2003)
Nickel-catalyzed cross-coupling of aryl halides with alkyl halides: Ethyl 4-(4-(4-methylphenylsulfonamido)-phenyl) butanoate
Everson DA, et al.
Organic Syntheses, 90(17), 200-200 (2013)
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