Acetyl bromide

Violently decomposed by alcohol and by water with formation of hydrobromic acid and acetic acid. Miscible with ether, chloroform, and benzene.1,2 

Alcohols and Water. Acetyl bromide reacts violently with alcohols or water.1 

The vapor irritates the respiratory system and eyes. The liquid burns skin and eyes. Swallowing causes severe internal irritation and damage. Avoid breathing vapor. Prevent contact with skin and eyes.2 

Wear nitrile rubber gloves, laboratory coat, and eye protection. A self-contained breathing apparatus may be necessary, depending on the size of the spill. Cover the spill with a 1 1 1 mixture by weight of sodium carbonate or calcium carbonate, clay cat litter (bentonite), and sand. When the acetyl bromide has been absorbed, scoop the mixture into a plastic pail and, in the fume hood, very slowly add the mixture to a pail of cold water. Allow it to stand for 24 hours. Test pH of the solution and neutralize if necessary with sodium carbonate. Decant the solution to the drain, flushing with at least 50 times its volume of water. Treat the solid residue as normal refuse.3-5 Wash the area of the spill thoroughly with soap and water.2 

Package Lots. Place in a separate labeled container for recycling or disposal by burning. Dissolve in a flammable solvent and burn in a furnace with a scrubber.3 

---

Acetyl bromide Acrylonitrile monomer Allyl chloride Allyl chloroformate Allyl iodide... 

Acetone cyanohydrin (stabilized), 6 Acetone tliiosemicarbazide, 6 Acetonitrile, 6 Acetophenetidin, 7 Acetophenone, 7 Acetyl acetone peroxide, 7 Acetyl bromide, 7 Acetyl chloride, 7... 

Surface-mediated addition of HC1 or HBr can be carried out in the presence of silica or alumina.150 The hydrogen halides can be generated from thionyl chloride, oxalyl chloride, oxalyl bromide, phosphorus tribromide, or acetyl bromide. The kinetic products from HC1 and 1-phenylpropyne result from syn addition, but isomerization to the more stable Z-isomer occurs upon continued exposure to the acidic conditions. 

Acetyl bromide cleaves dibenzyl sulfide, while diethyl or diisopropyl are resistant (27). 

Acylation of the piperazine nitrogen atoms of 47/,87/-bis[l,2,5]oxadiazolo[3,4- 4 -< ]pyrazine 59 with acetyl bromide proceeds smoothly in the presence of pyridine in acetonitrile to give 60 (Equation 9) <1997CHE618>. 

The addition of HBr to an alkyne can be facilitated by using acetyl bromide (CH3COBr) and alumina instead of aqueous HBr. 

The preparation reported here is based on the method of Christie and Rapoport.4 9-Bromo-9-phenylfluorene has also been prepared by a light-initiated reaction of bromine and 9-phenylfluorene in carbon disulfide,2 by addition of phenylmagnesium bromide to fluorene36 followed by treatment with acetyl bromide,5 and by treatment of 9-phenylfluorene with N-bromosuccinimide.6... 

Benzyl Bromide [Reductive Bromination of an Acetal].506 To a suspension of tin(II) bromide (5.1 mg, 0.02 mmol) and benzaldehyde dimethyl acetal (54.8 mg, 0.36 mmol) in CH2C12 (2.5 mL) were added successively Et3SiH (65.0 mg, 0.56 mmol) and acetyl bromide (96.8 mg, 0.79 mmol) in CH2C12 (1 mL) at room temperature under an argon atmosphere. The mixture was stirred for 3 hours at room temperature and quenched with a phosphate buffer (pH 7). 

Triphenylbromomethane may be made in a similar manner by substituting acetyl bromide for the acetyl chloride. 

---