619-42-1 Usage
Description
Methyl 4-bromobenzoate is a halogenated benzoate compound that serves as a versatile reagent in organic synthesis. It is characterized by the presence of a bromine atom attached to a benzene ring, with a methyl ester group attached to the carboxylic acid. This unique structure allows it to participate in various chemical reactions and be used in the synthesis of different compounds.
Uses
Used in Organic Synthesis:
Methyl 4-bromobenzoate is used as a reagent in organic synthesis for the preparation of various compounds. Its bromine atom can be replaced by other functional groups, making it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Environmental Applications:
Methyl 4-bromobenzoate is used to stimulate microbial dechlorination of polychlorinated biphenyls (PCBs). PCBs are a group of toxic, persistent environmental pollutants that pose a significant risk to human health and the environment. By promoting the dechlorination process, Methyl 4-bromobenzoate helps in the bioremediation of contaminated sites.
Used in Cancer Therapy:
Methyl 4-bromobenzoate is used in the preparation of stable radioiodinating reagents to label monoclonal antibodies for radiotherapy of cancer. Radiolabeled antibodies can specifically target cancer cells, allowing for targeted radiation therapy with minimal damage to healthy tissues.
Used in Pharmaceutical Synthesis:
Methyl 4-bromobenzoate is used as a starting material in the synthesis of three-carbon-bridged 5-substituted furo[2,3-d]pyrimidine and 6-substituted pyrrolo[2,3-d]pyrimidine analogs, which are employed as antifolates. Antifolates are a class of drugs that inhibit the synthesis of folic acid, an essential nutrient for cell growth and replication, and are used in the treatment of various cancers.
Used in Cross-Coupling Reactions:
Methyl 4-bromobenzoate is used in cross-coupling reactions to synthesize various derivatives, such as methyl 4-tri-n-butylstannylbenzoate, methyl 4-(2-pyridyl)benzoate, and methyl 4-imidazo[1,2-a]pyridin-3-ylbenzoate. These reactions involve the formation of carbon-carbon bonds and are essential for the synthesis of complex organic molecules, including pharmaceuticals and agrochemicals.
Purification Methods
Crystallise the ester from MeOH. EtOH (m 81o, also 80.5o, 79.5o) or *C6H6/pet ether (m 78-79o). [Beilstein 9 H 352, 9 III 1405, 9 IV 1017.]
Check Digit Verification of cas no
The CAS Registry Mumber 619-42-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 9 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 619-42:
(5*6)+(4*1)+(3*9)+(2*4)+(1*2)=71
71 % 10 = 1
So 619-42-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H7BrO2/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5H,1H3
619-42-1Relevant articles and documents
The tremulanes, a new group of sesquiterpenes from the aspen rotting fungus Phellinus tremulae
Ayer,Cruz
, p. 7529 - 7534 (1993)
A series of new sesquiterpenes, the tremulanes, possessing a previously unreported substituted perhydroazulene carbon skeleton, has been isolated from liquid cultures of the aspen (Populus tremuloides) rotting fungus Phellinus tremulae. The structures were determined by NMR techniques (1H- 1H COSY, HMQC, and HMBC) and other physical methods including, in the case of tremulenolide A (6), X-ray crystallography. The chemical correlation of tremulenediol A (10) with tremulenolide A (6) is described as is the correlation of tremulenedial (8) with tremulenediol B (11). The absolute configuration of the compounds is assigned by application of the olefin octant rule to the allylic alcohol tremulenediol A (10). These new sesquiterpenes do not obey the biogenetic isoprene rule and it is suggested that they may not be derived from farnesyl pyrophosphate.
Acetyl nitrate mediated conversion of methyl ketones to diverse carboxylic acid derivatives
Bernard, Josephine,Capilato, Joseph N.,Hoy, Erik P.,Mattiucci, Joseph,Pellegrinelli, Peter J.,Perez, Lark J.,Philippi, Shane,Schnorbus, Logan
supporting information, p. 5298 - 5302 (2021/06/30)
The development of a novel acetyl nitrate mediated oxidative conversion of methyl ketones to carboxylic acid derivatives is described. By analogy to the haloform reaction and supported by experimental and computational investigation we propose a mechanism for this transformation.
Method for preparing carboxylic ester compounds by oxidizing and breaking carbon-carbon bonds of secondary alcohol compounds
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Paragraph 0056-0057; 0092, (2021/06/02)
The invention discloses a method for preparing carboxylic ester compounds by oxidizing and breaking carbon-carbon bonds of secondary alcohol compounds. The method comprises the following steps: adding a secondary alcohol compound, an additive and a nitrogen-doped mesoporous carbon loaded monatomic catalyst into a fatty primary alcohol solvent, putting into a pressure container, sealing, introducing oxygen source gas with a certain pressure, controlling the pressure of the oxygen source gas to be 0.1-1 MPa and the reaction temperature to be 80-150 DEG C, and obtaining a product after the reaction to be the carboxylic ester compound. The nitrogen-doped mesoporous carbon-loaded monatomic catalyst adopted by the invention is high in activity, the highest separation yield of the carboxylic ester compound as a reaction product reaches 99%, the method is wide in application range, the reaction conditions are easy to control, the catalyst can be recycled, the post-treatment is simple, and the method is suitable for industrial production.
