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D38405

Sigma-Aldrich

2,4-Dibromoaniline

98%

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About This Item

Linear Formula:
Br2C6H3NH2
CAS Number:
615-57-6
Molecular Weight:
250.92
Beilstein:
2206653
EC Number:
210-434-4
MDL number:
MFCD00007633
UNSPSC Code:
12352100
PubChem Substance ID:
24893786
NACRES:
NA.22

Assay

98%

form

crystals

mp

78-80 °C (lit.)

SMILES string

Nc1ccc(Br)cc1Br

InChI

1S/C6H5Br2N/c7-4-1-2-6(9)5(8)3-4/h1-3H,9H2

InChI key

DYSRXWYRUJCNFI-UHFFFAOYSA-N

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Application

2,4-Dibromoaniline can be used as:
  • A starting material to synthesize acetylenic amine by reacting with trimethylsilylacetylene, which is used as a ligand to prepare the bis-amido complex of Ti(IV).
  • A substrate in the Pd-catalyzed ortho-selective cross-coupling reactions of dihaloarenes with Grignard reagents.
  • A reactant to prepare dialkyl-substituted aminoaryl sulfides using a Grignard reagent.
  • A starting material to synthesize substituted 2-mercapto benzimidazoles.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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DHTP Ligands for the Highly Ortho-Selective, Palladium-Catalyzed Cross-Coupling of Dihaloarenes with Grignard Reagents: A Conformational Approach for Catalyst Improvement
Ishikawa S and Manabe K
Angewandte Chemie (International Edition in English), 122(4), 784-787 (2010)
Copper (I)-catalyzed synthesis of substituted 2-mercapto benzimidazoles
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Synthesis and crystal structure of (η5-C5H5)2 Ti(NH (2, 4-(C CSiMe3) 2C6H3)) 2
Zhang L, et al.
Journal of Chemical Crystallography, 35(9), 673-677 (2005)

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