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523267

Sigma-Aldrich

4-Bromo-2-iodoaniline

97%

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About This Item

Linear Formula:
BrC6H3(I)NH2
CAS Number:
66416-72-6
Molecular Weight:
297.92
MDL number:
MFCD02093764
UNSPSC Code:
12352100
PubChem Substance ID:
24874329
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

mp

69-72 °C (lit.)

functional group

bromo
iodo

SMILES string

Nc1ccc(Br)cc1I

InChI

1S/C6H5BrIN/c7-4-1-2-6(9)5(8)3-4/h1-3H,9H2

InChI key

HHTYEQWCHQEJNV-UHFFFAOYSA-N

General description

4-Bromo-2-iodoaniline is a 2-iodoaniline derivative. It can be prepared by reacting 4-bromoaniline with iodine.

Application

4-Bromo-2-iodoaniline may be used in the following:
  • Preparation of quinolone derivatives.
  • Synthesis of a resin-bound sulfonamide, which was used as a starting material for the preparation of 2,3,5-trisubstituted indoles.

Signal Word

Danger

Hazard Statements

H301,H315,H318,H335,H411

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 2 - Eye Dam. 1 - 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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

523267-VAR:
523267-BULK:
523267-5G:4548173989242

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Certificates of Analysis (COA)

Lot/Batch Number
MKBR8925V
MKBF3972V
MKBF3972
MKBB5426
05626DH

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T Y Wu et al.
Organic letters, 3(24), 3827-3830 (2001-11-27)
2,3,5-Trisubstituted indoles are synthesized in three steps starting from resin-bound aniline 2. R1 is introduced by a palladium-mediated coupling of the aryl iodide with terminal alkynes followed by intramolecular cyclization to form the indole core. Acylation at C-3 with an
ON SOME HALOGEN DERIVATIVES OF AROMATIC AMINES AND THEIR ANALYSIS. I. 1.
Dains FB, et al.
Journal of the American Chemical Society, 40(6), 930-936 (1918)
Palladium-catalyzed synthesis of 2-quinolone derivatives from 2-iodoanilines.
Cortese NA, et al.
The Journal of Organic Chemistry, 43(15), 2952-2958 (1978)
Shaei Huang et al.
Bioorganic & medicinal chemistry letters, 16(22), 5907-5912 (2006-09-23)
Through a comparison of X-ray co-crystallographic data for 1 and 2 in the Chek1 active site, it was hypothesized that the affinity of the indolylquinolinone series (2) for Chek1 kinase would be improved via C6 substitution into the hydrophobic region

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