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539392

Sigma-Aldrich

2-Bromo-4′-cyanoacetophenone

96%

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About This Item

Linear Formula:
BrCH2COC6H4CN
CAS Number:
20099-89-2
Molecular Weight:
224.05
MDL number:
MFCD00052931
UNSPSC Code:
12352100
PubChem Substance ID:
24878394
NACRES:
NA.22

Assay

96%

mp

92-96 °C (lit.)

SMILES string

BrCC(=O)c1ccc(cc1)C#N

InChI

1S/C9H6BrNO/c10-5-9(12)8-3-1-7(6-11)2-4-8/h1-4H,5H2

InChI key

LJANCPRIUMHGJE-UHFFFAOYSA-N

General description

2-Bromo-4′-cyanoacetophenone can be synthesized from ethylbenzene via aerobic photooxidation using aqueous HBr.

Application

2-Bromo-4′-cyanoacetophenone may be used to synthesize:
  • 3-acylindolizines
  • (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol
  • 1-[2-(4-cyanophenyl)-2-oxoethyl]-1,10-phenanthrolinium bromide

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 + H312 + H332,H314

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

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

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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Application of DMF?methyl sulfate adduct in the regioselective synthesis of 3-acylated indolizines.
Przewloka T, et al.
Tetrahedron Letters, 48(33), 5739-5742 (2007)
New 1, 10-phenanthroline derivatives with potential antitumoral activity.
Dumitrascu F, et al.
Rev. Roum. Chim., 53(3), 183-187 (2008)
Synthesis and antifungal activity of novel thiazole-containing triazole antifungals. II. Optically active ER-30346 and its derivatives.
Tsuruoka, Akihiko, et al.
Chemical & Pharmaceutical Bulletin, 46(4), 623-630 (1998)
Norihiro Tada et al.
Organic & biomolecular chemistry, 8(20), 4701-4704 (2010-08-27)
The direct synthesis of α-bromoketones from alkylarenes by aerobic photooxidation with hydrobromic acid is reported. The key success for this direct oxidative reaction is due to control of bromination with acetic acid and ethanol, which are generated in situ by

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