506-96-7 Usage
Uses
1. Used in Fine Chemicals, Agrochemicals, and Pharmaceuticals:
Acetyl bromide is used as an acetylating agent for the synthesis of fine chemicals, agrochemicals, and pharmaceuticals. It helps incorporate the acetyl group into a molecule by substitution for protecting –OH groups, which is essential for various chemical reactions and product development.
2. Used in Dye Synthesis:
Acetyl bromide serves as an intermediate in the synthesis of dyes, contributing to the production of a wide range of colorants used in various industries.
3. Used in the Quantification of Lignin:
Acetyl bromide is employed in the quantification of lignin in cell wall residues of Arabidopsis, a model plant species, which aids in understanding the composition and structure of plant cell walls.
4. Used in the Total Synthesis of Cinchona Alkaloids:
Acetyl bromide is utilized in the total synthesis of cinchona alkaloids, such as quinidine and quinine, which are important compounds with medicinal applications.
5. Used in the Preparation of 9,10-Diarylanthracenes and Triarylmethanes:
Acetyl bromide is used to prepare 9,10-diarylanthracenes and triarylmethanes by reacting with arenes and various aromatic aldehydes using ZnBr2/SiO2, which are valuable compounds in the field of organic chemistry.
6. Used in the Preparation of Glycosyl Bromides:
Acetyl bromide is employed in the preparation of glycosyl bromides from free sugars or their peracetates, which are essential intermediates in the synthesis of various complex carbohydrates and related compounds.
Preparation
The preparation of acetyl bromide from acetic acid and bromine in the presence of red and yellow phosphorus.Reaction: Acetic anhydride was brominated with bromine at 80°C, and then the bromine was added between 95°C and 125°C. About 2.5h. After the addition was completed, reflux was continued for 3h and left overnight. Refined by fractional distillation.Acetyl bromide may also be prepared by reaction between phosphorus tribromide and acetic acid:3CH3COOH + PBr3 → 3 CH3COBr + H3PO3
Reactivity Profile
Acetyl bromide decomposes violently upon contact with water, steam, methanol or ethanol to form hydrogen bromide gas and acetic acid. Reacts vigorously with bases, both organic and inorganic. Incompatible with oxidizing agents and alcohols. Produces highly toxic fumes of bromine and carbonyl bromide when heated to decomposition [Sax, 9th ed., 1996, p. 34]. Vapor forms an explosive mixture with air [Kirk-Othmer, 3rd ed., Vol. 1, 1978, p. 162]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
Health Hazard
Exposures to acetyl bromide cause abdominal pain, sore throat, cough, burning sensation,
shortness of breath, and respiratory distress. Contact with the skin causes pain,
redness, blisters, dermatitis, and skin burn, severe deep burns, loss of vision, shock or
collapse. The occupational worker may show delayed symptoms and lung edema. The
vapor is corrosive to the eyes, the skin, and the respiratory tract. The irritation caused by
acetyl bromide may lead to chemical pneumonitis and pulmonary edema, and may cause
burns to the respiratory tract. The target organs include the eyes, skin, and the mucous
membranes.
Chemical Reactivity
Reactivity with Water: Reacts violently, forming corrosive and toxic fumes of hydrogen bromide; Reactivity with Common Materials: Attacks and corrodes wood and most metals in the presence of moisture. Flammable hydrogen gas may collect in enclosed spaces; Stability During Transport: Stable if protected from moisture; Neutralizing Agents for Acids and Caustics: Flood with water, rinse with dilute sodium bicarbonate or soda ash solution; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Safety Profile
Poison by ingestion, inhalation, skin contact, and intraperitoneal routes. See also HYDROBROMIC ACID and ACETIC ACID. Violent reaction on contact with water, steam, methanol, or ethanol produces toxic and reactive HBr. When heated to decomposition it emits highly corrosive and toxic fumes of carbonyl bromide and bromine. To fight fire, use dry chemical, CO2
Potential Exposure
Acetyl bromide is used as an acetylating agent in the organic synthesis of other chemicals, pesticides, perfume, pharmaceuticals, and it is also used as a dye intermediate.
storage
Acetyl bromide should be stored in a tightly sealed container, in a cool, dry, well-ventilated
area, away from water and incompatible substances.
Shipping
UN1716 Acetyl bromide, Hazard class: 8; Labels: 8-Corrosive material
Purification Methods
Boil acetyl bromide with PBr3/Ac2O for 1hour, then distil the latter off and redistil it. Store it dry. [Burton & Degering J Am Chem Soc 62 227 1940, Beilstein 2 IV 398.] LACHRYMATORY.
Incompatibilities
Acetyl bromide Vapor may form explosive mixture with air. Instability increases as temperature rises, Contact with moisture, water, steam, alcohols cause a violent reaction releasing corrosive carbonyl bromide, hydrogen bromide, and bromine gases. Incompatible with organic solvents, ethers, oxidizers, and strong bases. Corrodes or attacks most metals and wood in the presence of moisture. Contact with combustibles may cause ignition
Waste Disposal
Dispose of contents and container to an approved waste disposal plant. All federal, state, and local environmental regulations must be observed. Slow addition to sodium bicarbonate solution in a glass or plastic container. Mix slowly in another container containing lots of water. It is inappropriate and possibly dangerous to the environment to dispose of chemical wasteby flushing them down the toilet or discarding them to the trash
Precautions
Acetyl bromide is combustible and emits irritating or toxic fumes (or gases) in a fire. It should have no contact with naked flames or water. During use, occupational workers should use protective gloves, protective clothing, a face shield or eye protection in combination with breathing protection and should not eat, drink, or smoke. Acetyl bromide decomposes on heating and produces toxic and corrosive fumes, such as hydrogen bromide and carbonyl bromide. It reacts violently with water, methanol, or ethanol to form hydrogen bromide. Acetyl bromide attacks and damages many metals in the presence of water.
Check Digit Verification of cas no
The CAS Registry Mumber 506-96-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 6 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 506-96:
(5*5)+(4*0)+(3*6)+(2*9)+(1*6)=67
67 % 10 = 7
So 506-96-7 is a valid CAS Registry Number.
InChI:InChI=1/C2H3BrO/c1-2(3)4/h1H3
506-96-7Relevant articles and documents
Rate coefficients for the reactions CH3 + Br2 (224-358 K), CH3CO + Br2 (228 and 298 K), and Cl + Br 2 (228 and 298 K)
Khamaganov,Crowley
, p. 575 - 585 (2010)
Rate coefficients for the reactions of CH3 + Br2 (k2), CH3CO + Br2 (k3), and Cl + Br2 (k5) were measured using the laser-pulsed photolysis method combined with detection of the product Br atoms using resonance fluorescence. For the reactions involving organic radicals, the rate coefficients were observed to increase with decreasing temperature and within the temperature range explored, were adequately described by Arrhenius-like expressions: k2 (224-358 K) = 1.83×10-11 exp(252/T) and k3 (228-298 K) = 2.92×10-11 exp(361/T) cm 3 molecule-1 s1. The total, temperature-independent uncertainty for each reaction (including possible systematic errors in Br2 concentration measurement) was estimated as ～7% for k2 and 10% for k3. Accurate data on k5 was obtained at 298 K, with a value of 1.88×10-10 cm3 molecule-1 s-1 obtained (with an associated error of 6%). A limited data set at 228 K suggests that k5 is, within experimental uncertainty, independent of temperature.
Mapping-Out Catalytic Processes in a Metal–Organic Framework with Single-Crystal X-ray Crystallography
Burgun, Alexandre,Coghlan, Campbell J.,Huang, David M.,Chen, Wenqian,Horike, Satoshi,Kitagawa, Susumu,Alvino, Jason F.,Metha, Gregory F.,Sumby, Christopher J.,Doonan, Christian J.
, p. 8412 - 8416 (2017)
Single-crystal X-ray crystallography is employed to characterize the reaction species of a full catalytic carbonylation cycle within a MnII-based metal–organic framework (MOF) material. The structural insights explain why the Rh metalated MOF is catalytically competent toward the carbonylation of MeBr but only affords stoichiometric turn-over in the case of MeI. This work highlights the capability of MOFs to act as platform materials for studying single-site catalysis in heterogeneous systems.
Synthesis method for organic synthesis of intermediate acetyl bromide
-
Paragraph 0014; 0015, (2018/07/30)
The invention relates to a synthesis method for organic synthesis of an intermediate acetyl bromide. The method mainly includes the steps of: adding 3mol acetamide into a reaction container, raising the temperature to 50-55DEG C, controlling the stirring speed at 110-130rpm, slowly adding 4-5mol hydrogen bromide, then raising the temperature of the solution to 80-85DEG C, maintaining reflux for 90-110min, conducting reduced pressure distillation, collecting 50-55DEG C fraction, conducting washing with an acetone solution and a hexane solution respectively, and conducting dehydration with a dehydrant, thus obtaining the finished product acetyl bromide.
METHOD FOR PRODUCING a-HALO-TETRAACYL-GLUCOSE
-
, (2016/01/29)
There is provided an efficient and excellent preparation method of an α-halo-tetraacyl-glucose which is suitable for industrial preparation, which comprises reacting D-glucose or lower alkyl D-glucoside with a reactive derivative of a carboxylic acid and a metal halide to prepare the α-halo-tetraacyl-glucose represented by the formula (III): wherein R represents an optionally substituted lower alkyl group or an optionally substituted aryl group, and X represents a halogen atom, in one step, and the resulting α-halo-tetraacyl-glucose (III) can be converted into a compound of the formula (I) or a salt thereof by subjecting to a conventional method.
Photochemical reactions of acyl iodides with aryl halides
Voronkov,Vlasova,Belousova,Vlasov,Vakul'Skaya,Prozorova,Khutsishvili
, p. 17 - 21 (2013/03/29)
Photochemical reactions of acyl iodides RC(O)I (R = Me, Ph) with aryl halides, fluoro-, chloro-, and bromobenzenes, 1,4-dibromobenzene, 2- and 3-bromotoluenes, and 4-bromo-1,2-dimethylbenzene, were studied. Acetyl iodide reacted with chloro- and bromobenzenes and 1,4-dibromobenzene according to the exchange pattern to give iodobenzene and 1,4-diiodobenzene, respectively. No halogen exchange was observed in the reactions of acetyl iodide with fluorobenzene and hexafluorobenzene. Benzoyl iodide failed to react with chloro- and brombenzene under UV irradiation but underwent polycondensation with formation of black nonfusible oligomers which were found to possess paramagnetic and semiconducting properties. Ultraviolet irradiation of a mixture of MeCOI with 2- or 3-bromotoluene, as well as with 4-bromo-1,2-dimethylbenzene, also led to the formation of polymeric products as a result of polycondensation of aryl iodides formed initially via replacement of bromine by iodine. Irradiation of benzoyl iodide in 2- or 3-bromotoluene involved recombination of benzoyl radicals to give benzil as the only product.
Liquid-phase oxidation of bromovinyl compounds with molecular oxygen
Bayatyan,Bayatyan,Saakyan
, p. 1849 - 1852 (2008/02/08)
Liquid-phase oxidation of bromovinyl compounds with the aim to obtain the corresponding α-bromo acids was studied.
Inhibitors of the ICE/ced-3 family of cysteine proteases
-
, (2008/06/13)
This invention is directed to novel oxamyl dipeptide ICE/ced-3 family inhibitor compounds having the following structure: wherein A, B, R, R1, R1′ p and q are as defined herein. The invention is also directed to pharmaceutical compositions containing one or more of these compounds, as well as to the use of such compositions in the treatment of patients suffering inflammatory, autoimmnune and neurodegenerative diseases, for the prevention of ischemic injury, and for the preservation of organs that are to undergo a transplantation procedure.
Method for treating allergies using substituted pyrazoles
-
, (2008/06/13)
A method for treating an allergic condition, including an atopic allergic condition, using substituted pyrazoles.
Inhibitors of the ICE/ced-3 family of cysteine proteases
-
, (2008/06/13)
This invention is directed to novel sulfonimide (substituted)acyl dipeptidyl ICE/ced-3 family inhibitor compounds having the following structure: wherein A, B, X, R, R1, R2, n, q, and r are as defined herein. The invention is also directed to pharmaceutical compositions containing these compounds, as well as the use of such compositions in the treatment of patients suffering inflammatory, autoimmune and neurodegenerative diseases, for the prevention of ischemic injury, and for the preservation of organs that are to undergo a transplantation procedure.
