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Merck

135968

Acetyl bromide

99%

Synonym(s):

Acetic acid bromide

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About This Item

Linear Formula:
CH3COBr
CAS Number:
506-96-7
Molecular Weight:
122.95
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24848248
EC Number:
208-061-7
Beilstein/REAXYS Number:
1697546
MDL number:
MFCD00000114
Assay:
99%
Form:
liquid

Key Documents

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InChI key

FXXACINHVKSMDR-UHFFFAOYSA-N

InChI

1S/C2H3BrO/c1-2(3)4/h1H3

SMILES string

CC(Br)=O

vapor density

4.3 (vs air)

vapor pressure

92.2 mmHg ( 25 °C)

assay

99%

form

liquid

refractive index

n20/D 1.45 (lit.)

bp

75-77 °C (lit.)

mp

−96 °C (lit.)

solubility

benzene: miscible, chloroform: miscible, diethyl ether: miscible

density

1.663 g/mL at 25 °C (lit.)

Quality Level

200

Related Categories

General description

Acetyl bromide effectively mediates Nazarov cyclization of a cross-conjugated pentadienone to give (±)-methyl rocaglate. It is added to dissolve Arabidopsis lignin during acetyl bromide method for rapid microscale determination of lignin content in Arabidopsis.

Application

Acetyl bromide can be used:
  • In the quantification of lignin in cell wall residues of Arabidopsis.
  • In the total synthesis of cinchona alkaloids named quinidine and quinine.
  • To prepare 9,10-diarylanthracenes and triarylmethanes by reacting with arenes and various aromatic aldehydes using ZnBr2/SiO2.
  • To prepare glycosyl bromides from free sugars or their peracetates.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H290,H314

Hazard Classifications

Eye Dam. 1 - Met. Corr. 1 - Skin Corr. 1B

supp_hazards

EUH014

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 2

flash_point_f

No data available

flash_point_c

No data available

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBH4979V
SHBH3924V
SHBG9822V
STBG0902V
SHBF7034V

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Annelie Gutsch et al.
BMC plant biology, 19(1), 271-271 (2019-06-23)
The heavy metal cadmium (Cd) accumulates in the environment due to anthropogenic influences. It is unessential and harmful to all life forms. The plant cell wall forms a physical barrier against environmental stress and changes in the cell wall structure
Catalytic asymmetric total syntheses of quinine and quinidine
Raheem IT, et al.
Journal of the American Chemical Society, 126(3), 706-707 (2004)
Mild one-pot preparation of glycosyl bromides
Hunsen M, et al.
Carbohydrate Research, 340(17), 2670-2674 (2005)
Oliver R A Corea et al.
Methods in molecular biology (Clifton, N.J.), 908, 229-250 (2012-07-31)
Single and multiple T-DNA knockouts of genes encoding arogenate dehydratases (ADTs) in Arabidopsis were obtained in homozygous form. These were analyzed for potential differences in lignin contents and compositions, as well as for distinct phenotypes over growth and development. Of
Convenient synthesis of triarylmethanes and 9, 10-diarylanthracenes by alkylation of arenes with aromatic aldehydes using acetyl bromide and ZnBr2/SiO2
Kodomari M, et al.
Tetrahedron Letters, 49(16), 2537-2540 (2008)
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