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135968

Sigma-Aldrich

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
Beilstein:
1697546
EC Number:
208-061-7
MDL number:
MFCD00000114
UNSPSC Code:
12352100
PubChem Substance ID:
24848248
NACRES:
NA.22

vapor density

4.3 (vs air)

Quality Level

200

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.)

SMILES string

CC(Br)=O

InChI

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

InChI key

FXXACINHVKSMDR-UHFFFAOYSA-N

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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

Signal Word

Danger

Hazard Statements

H290,H314

Hazard Classifications

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

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 2

Flash Point(F)

No data available

Flash Point(C)

No data available

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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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
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)
Laser microdissection and genetic manipulation technologies to probe lignin heterogeneity and configuration in plant cell walls
Biomass Conversion (2012)
R D Hatfield et al.
Journal of agricultural and food chemistry, 47(2), 628-632 (1999-11-24)
The acetyl bromide assay was developed to provide a rapid and sensitive method for quantifying lignin in woody plant species. The original procedure cautioned against prolonged reaction times and advised keeping the reaction temperature at 70 degrees C to prevent
R S Fukushima et al.
Journal of agricultural and food chemistry, 49(7), 3133-3139 (2001-07-17)
Lignin extracted with acidic dioxane was investigated as a possible standard for quantitatively determining lignin content in plant samples using the spectrophotometric method employing acetyl bromide. Acidic dioxane lignins were analyzed for carbohydrate, total protein, nitrobenzene oxidation products, and UV
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