6751-75-3

Basic information

• Product Name: 2-BROMORESORCINOL
• Synonyms: 2-BroMo-1,3-benzenediol;2-BroMo-1,3-dihydroxybenzene;2-Bromoresorcinol 95%
• CAS NO: 6751-75-3
• Molecular Formula: C₆H₅BrO₂
• Molecular Weight: 189.01
• Product Categories: Alcohols;Aryl;Building Blocks;C2 to C6;C6;Chemical Synthesis;Halogenated Hydrocarbons;New Products for Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 6751-75-3.mol

Chemical Properties

• Melting Point: 96-103℃
• Boiling Point: 235.3±20.0℃ (760 Torr)
• Flash Point: 96.1±21.8℃
• Appearance: /
• Density: 1.844±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.0329mmHg at 25°C
• Refractive Index: 1.657
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 7.91±0.10(Predicted)
• CAS DataBase Reference: 2-BROMORESORCINOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMORESORCINOL(6751-75-3)
• EPA Substance Registry System: 2-BROMORESORCINOL(6751-75-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 6751-75-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Bromoresorcinol is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form complex molecules, contributing to the development of new drugs and therapeutic agents.
Used in Organic Compounds Production:
It is utilized as a starting material in the production of dyes, pigments, and other organic chemicals, enhancing the color and properties of these products.
Used in Antifungal Applications:
2-Bromoresorcinol is used as an antifungal agent for its potential to combat fungal infections, providing a valuable alternative in the treatment of various fungal diseases.
Used in Antibacterial Applications:
It is employed as an antibacterial agent, leveraging its potential to inhibit bacterial growth, which can be instrumental in the development of new antimicrobial therapies.

InChI:InChI=1/C6H5BrO2/c7-6-4(8)2-1-3-5(6)9/h1-3,8-9H

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 2437-49-2 2,4,6-tribromoresorcinol 
• 7732-18-5 water 
• 608-21-9 1,2,3-tribromobenzene 
• 116595-48-3 3-bromo-2,4-dihydroxybenzoic acid 
• 108-46-3 recorcinol 
• 16932-45-9 1-bromo-2,6-dimethoxybenzene 

Downstream Products

• 1352651-05-8 2-bromo-1,3-bis(hept-6-enyloxy)benzene 
• 1352651-06-9 2-bromo-1 ,3-bis(dec-9-enyloxy)benzene 
• 1352651-07-0 2-bromo-1,3-bis(undec-10-enyloxy)benzene 
• 1352651-08-1 C₂₀H₃₁BO₄ 
• 1352651-09-2 2,6-bis(dec-9-enyloxy)phenylboronic acid 
• 1352651-10-5 2,6-bis(undec-10-enyloxy)phenylboronic acid 
• 1352659-13-2 6,14-bis[2,6-bis(dec-9-enyloxy)phenyl]-5,7,13,15-tetraoxa-6,14-diborahexacyclo[9.5.1.1(3.9).0(2,10).0(4.8).0(12,16)]octadecane 
• 1352659-14-3 6,14-bis[2,6-bis(undec-10-enyloxy)phenyl]-5,7,13,15-tetraoxa-6,14-diborahexacyclo[9.5.1.1(3.9).0(2,10).0(4.8).0(12,16)]octadecane 
• 13345-26-1 7-hydroxy benzopyrene 

Relevant articles and documents

1-Bromo-2,6-dihydroxybenzene containing R44(8) rings and C(2) helices

Molecules of the title compound (also known as 2-bromoresorcinol), C 6H5BrO2, are essentially planar and possess normal geometrical parameters. The crystal packing is influenced by O - H...O and O - H...O/Br hydrogen bonds

Total Synthesis of Caesalpinnone A

Total synthesis of caesalpinnone A was achieved in 12 steps starting from resorcinol. Key features of the synthesis include BINOL-phosphoric acid catalyzed [4 + 2] cycloaddition, trans-selective nucleophilic substitution, deallylation/oxa-Michael addition cascade, and late-stage photo-Fries rearrangement.

Kolbe-Schmitt type reaction under ambient conditions mediated by an organic base

The combined use of an organic base for resorcinols realized a Kolbe-Schmitt type reaction under ambient conditions. When resorcinols (3-hydroxyphenol derivatives) were treated with DBU under a carbon dioxide atmosphere, nucleophilic addition to carbon dioxide proceeded to afford the corresponding salicylic acid derivatives in high yields.

Synthesis of tetra-pincer nickel(ii) and palladium(ii) complexes of resorcin[4]arene-octophosphinite [Res(OPR2)8] and rhodium-catalyzed regioselective hydroformylation reaction

The condensation reaction of resorcinol with pentanal yielded resorcin[4]arene 1 which on bromination using N-bromosuccinimide at room temperature produced tetra-bromide derivative 2. The reactions of 2 with chlorodiphenylphosphine and o-phenylenephosphoro-chloridite yielded octaphosphinite 3 (hereafter referred to as octaphos) and octaphosphite 4, respectively. The reactions of 3 with Ni(COD)2 or Pd2(dba)3·CHCl3 in appropriate molar ratios yielded tetra-pincer complexes 5 and 6, respectively. The structures of both the complexes were established by single crystal X-ray diffraction studies. The resorcin[4]arene backbone adopts a boat structure in these complexes. Typically, the Rh-catalyzed hydroformylation of styrene prevalently delivers a branched (b) chiral aldehyde. A unique resorcin[4]arene skeleton based octaphos 3 was employed in the Rh-catalyzed hydroformylation of styrene. The hydroformylation of styrene with a metal to ligand ratio of 1:1 (M:L) was found to be regioselective, producing a linear (l) aldehyde as a major product with 100% conversion in 3 h. The l:b ratio surprisingly increased when the ortho positions of styrene were populated by methyl and chloro substituents. The hydroformylation of p-nitro styrene triggered a remarkably high linear:branched aldehyde ratio of 2.4 (71% linear aldehyde) despite its electron withdrawing nature. The highest linear selectivity of 97% (l:b ratio 27.8) was achieved in the case of 2,4,6-trimethylstyrene.

A dehydrobenzene precursor and its synthetic method

The invention discloses a benzyne precursor and a synthesis method thereof. The benzyne precursor has a structure shown as the formula which is shown in the specification. The synthesis method of the benzyne precursor comprises the two steps: synthesizing

Trifluoromethanesulfonyloxy-group-directed regioselective (3 + 2) cycloadditions of benzynes for the synthesis of functionalized benzo-fused heterocycles

Highly regioselective (3 + 2) cycloadditions of (trifluoromethanesulfonyloxy)benzynes [(triflyloxy)benzynes] with 1,3-dipoles followed by cross-coupling reactions provided multisubstituted benzo-fused heterocycles. The triflyloxy group at the 3-position of benzynes, and even that at the remote 4-position, greatly affected the regiocontrol of the cycloaddition. These groups also served to install other substituents at their ipso-positions.

Synthesis of 13C4-labelled oxidized metabolites of the carcinogenic polycyclic aromatic hydrocarbon benzo[a]pyrene

Polycyclic aromatic hydrocarbons (PAHs), such as benzo[a]pyrene (BaP), are ubiquitous environmental contaminants that are implicated in causing lung cancer. BaP is a component of tobacco smoke that is transformed enzymatically to active forms that interact with DNA. We reported previously development of a sensitive stable isotope dilution LC/MS method for analysis of BaP metabolites. We now report efficient syntheses of 13C4-BaP and the complete set of its 13C4-labelled oxidized metabolites needed as internal standards They include the metabolites not involved in carcinogenesis (Group A) and the metabolites implicated in initiation of cancer (Group B). The synthetic approach is novel, entailing use of Pd-catalyzed Suzuki, Sonogashira, and Hartwig cross-coupling reactions combined with PtCl2-catalyzed cyclization of acetylenic compounds. This synthetic method requires fewer steps, employs milder conditions, and product isolation is simpler than conventional methods of PAH synthesis. The syntheses of 13C4-BaP and 13C4-BaP-8-ol each require only four steps, and the 13C-atoms are all introduced in a single step. 13C4-BaP-8-ol serves as the synthetic precursor of all the oxidized metabolites of 13C-BaP implicated in initiation of cancer. The isotopic purities of the synthetic 13C 4-BaP metabolites were estimated to be ≥99.9%.

Urolithin as a Converging Scaffold Linking Ellagic acid and Coumarin Analogues: Design of Potent Protein Kinase CK2 Inhibitors

Casein kinase2 (CK2) is a ubiquitous, essential, and highly pleiotropic protein kinase; its abnormally high constitutive activity is suspected to underlie its pathogenic potential in neoplasia and other relevant diseases. Previously, using different in silico screening approaches, two potent and selective CK2 inhibitors were identified by our group: ellagic acid, a naturally occurring tannic acid derivative (Ki=20nM) and 3,8-dibromo-7-hydroxy-4-methylchromen-2-one (DBC, Ki=60nM). Comparing the crystallographic binding modes of both ellagic acid and DBC, an X-ray structure-driven merging approach was taken to design novel CK2 inhibitors with improved target affinity. A urolithin moiety is proposed as a possible bridging scaffold between the two known CK2 inhibitors, ellagic acid and DBC. Optimization of urolithinA as the bridging moiety led to the identification of 4-bromo-3,8-dihydroxy-benzo[c]chromen-6-one as a novel, potent and selective CK2 inhibitor, which shows a Ki value of 7nM against the protein kinase, representing a significant improvement in affinity for the target compared with the two parent fragments. Two become one: Comparing the crystallographic binding modes of ellagic acid (red) and 3,8-dibromo-7-hydroxy-4-methylchromen-2-one (DBC; blue), an X-ray structure-driven merging approach to the design of novel casein kinase2 (CK2) inhibitors was taken. Using this strategy, a potent and selective urolithin derivative, 4-bromo-3,8-dihydroxy-benzo[c]chromen-6-one was identified, which exhibits a Ki value of 7nM against CK2.

Enantioselective synthesis of (+)-estrone exploiting a hydrogen bond-promoted Diels?Alder reaction

Starting from Danes diene and methylcyclopentenedione, (+)-estrone is synthesized along the Quinkert?Dane route in 24% total yield. The key step is an enantioselective Diels?Alder reaction promoted by an amidinium catalyst as efficiently as by a traditional Ti-TADDOLate Lewis acid.

Towards allosteric receptors - Synthesis of Resorcinarene-Functionalized 2,2′-Bipyridines and their metal complexes

Based on a first: example of an allosteric hemicarcerand (1) we prepared four new 2,2′bipyridines that carry resorcinarene moieties in a highly convergent manner. Upon coordination to suitable transition metal ions or their complexes these compounds undergo conformational changes in a way that: they switch between "open" and. "closed" forms (2, 3, and 4) or vice versa (5), thus, bringing together or separating the two functional, moieties on the central, bipyridine, Among the transition metal complexes that act: as effectors for the conformational switching, [Re(CO)5Cl] and monomeric copper(I) complexes of sterically hindered 2,9-arylated 1,10-phenanthrolines proved, to be very effective.