2316-64-5

Basic information

• Product Name: 5-Bromo-2-hydroxybenzyl alcohol
• Synonyms: BROMOSALIGENIN;2-HYDROXYMETHYL-4-BROMOPHENOL;5-BROMOSALIGENIN;5-BROMOSALICYL ALCOHOL;5-BROMO-2-HYDROXYBENZYL ALCOHOL;4-BROMO-2-HYDROXYMETHYLPHENOL;RARECHEM AL BD 0040;5-BROMO-2-HYDROXYBENZYL ALCOHOL, 98+%
• CAS NO: 2316-64-5
• Molecular Formula: C7H7BrO2
• Molecular Weight: 203.03
• EINECS: 219-026-0
• Product Categories: Benzhydrols, Benzyl & Special Alcohols
• Mol File: 2316-64-5.mol

Chemical Properties

• Melting Point: 110-112 °C(lit.)
• Boiling Point: 327.437 °C at 760 mmHg
• Flash Point: 151.829 °C
• Appearance: White to light brown/Crystalline Powder or Flakes
• Density: 1.5178 (rough estimate)
• Vapor Pressure: 0.00205mmHg at 25°C
• Refractive Index: 1.4620 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: water: soluble0.7% at 25°C(lit.)
• PKA: 9.36±0.18(Predicted)
• BRN: 509726
• CAS DataBase Reference: 5-Bromo-2-hydroxybenzyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-hydroxybenzyl alcohol(2316-64-5)
• EPA Substance Registry System: 5-Bromo-2-hydroxybenzyl alcohol(2316-64-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2316-64-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
5-Bromo-2-hydroxybenzyl alcohol is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in the Synthesis of 7-bromo-2,3-diphenyl-5H-imidazo[2,1-b][1,3]benzoxazine:
5-Bromo-2-hydroxybenzyl alcohol is used as a starting material for the synthesis of 7-bromo-2,3-diphenyl-5H-imidazo[2,1-b][1,3]benzoxazine, a compound with potential applications in the pharmaceutical industry.
Used in the Synthesis of 6-bromo-2-octyl-4H-1,3,2-benzodioxaphosphorin 2-oxide:
5-Bromo-2-hydroxybenzyl alcohol is utilized as a synthetic precursor for the production of 6-bromo-2-octyl-4H-1,3,2-benzodioxaphosphorin 2-oxide, which may have applications in the development of new pharmaceutical agents.
Used in the Synthesis of 4-bromo-2-(5-iodo-1H-indol-3-ylmethyl)-phenol:
5-Bromo-2-hydroxybenzyl alcohol is also used in the synthesis of 4-bromo-2-(5-iodo-1H-indol-3-ylmethyl)-phenol, a compound that could be relevant in the pharmaceutical sector for the development of novel therapeutics.

InChI:InChI=1/C7H7BrO2/c8-6-1-2-7(10)5(3-6)4-9/h1-3,9-10H,4H2

Upstream product

• 5532-69-4 4-bromo-2-(hydroxymethyl)phenol 
• 90-01-7 salicylic alcohol 
• 89-55-4 5-bromosalicyclic acid 
• 886504-46-7 3,4,5-tribromo-2-hydroxy-benzaldehyde 
• 1761-61-1 5-bromosalicyclaldehyde 
• 106-41-2 4-bromo-phenol 
• 7732-18-5 water 
• 67-64-1 acetone 
• 7647-01-0 hydrogenchloride 
• 7726-95-6 bromine 
• 82944-17-0 6-bromo-2,2-dimethylbenzo[1,3]dioxin-4-one 
• 50-00-0 formaldehyd 
• 123-75-1 pyrrolidine 
• 5460-29-7 2-(3-bromopropyl)isoindole-1,3-dione 

Downstream Products

• 80866-82-6 5-bromo-2-methoxy-benzyl alcohol 
• 1761-61-1 5-bromosalicyclaldehyde 
• 78563-03-8 5,5'-dibromo-2,2'-dihydroxy-diphenyl-methane 
• 133308-49-3 2-(2'-hydroxymethyl-4'-bromophenoxy)-1-phenylethanone 
• 198068-00-7 5-Bromo-2-hydroxybenzyl alcohol bis-TMS ether 
• 189684-09-1 3-[(allyloxy)methyl]-4-(allyloxy)bromobenzene 
• 627903-82-6 [2-(hydroxymethyl)-4-bromophenoxy]acetaldehyde dimethyl acetal 
• 817631-18-8 [5-bromo-2-(methoxyethoxymethoxy)]benzyl alcohol 
• 2362-12-1 4-Bromo-2-methylphenol 
• 177759-46-5 [2-(Benzyloxy)-5-bromophenyl]methanol 
• 760989-96-6 C₁₃H₁₉BO₄ 
• 54030-32-9 4-hydroxy-3-(hydroxymethyl)benzaldehyde 
• 54030-33-0 2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-carboxaldehyde 
• 189683-84-9 6-formyl-2-methyl-1,3-benzodioxin 

Relevant articles and documents

A Quantitative Assay of Sodium Triacetoxyborohydride

Sodium triacetoxyborohydride (STAB) is a common reducing agent with potency that degrades over time and is not uniformly assigned. A simple assay based on an aldehyde reduction has been developed to determine the active borohydride content of this reagent. The HPLC assay yield of a salicylaldehyde reduction has been shown to accurately determine this potency and has been validated against the H2 evolution method as well as yields obtained from a reductive amination. The use of these assay data to adjust the STAB charge as well to optimize a reductive amination has been demonstrated.

Porous Ge@C materials via twin polymerization of germanium(II) salicyl alcoholates for Li-ion batteries

The germylenes, germanium(ii) 2-(oxidomethyl)phenolate (1), germanium(ii) 4-methyl-2-(oxidomethyl)phenolate (2) and germanium(ii) 4-bromo-2-(oxidomethyl)phenolate (3) were synthesized and their thermally induced twin polymerization to give organic-inorganic hybrid materials was studied. The compounds 1-3 form oligomers including dimers, trimers and tetramers as a result of intermolecular coordination of the benzylic oxygen atom to germanium. The structural motifs were studied by single crystal X-ray diffraction analysis and DFT-D calculations. Thermally induced twin polymerization of these germylenes gave hybrid materials based on germanium-containing phenolic resins. Carbonization of these resins under reductive conditions resulted in porous materials that are composed of germanium and carbon (Ge@C materials), while oxidation with air provided non-porous germanium dioxide. The porous Ge@C materials were tested as potential anode materials for rechargeable Li-ion batteries. Reversible capacities of 540 mA h g-1 were obtained at a current density of 346 mA g-1 without apparent fading for 100 cycles, which demonstrates that germanium is well accessible in the hybrid material.

Synthesis, characterization and Twin Polymerization of a novel dioxagermine

The synthesis of 6-bromo-2,2-di-tert-butyl-4H-1,3,2-benzo[d]dioxagermine (1) via an alcohol/alkoxide exchange starting from di-tert-butyl-di-ethoxy germane is reported. Characterization of the title compound including single crystal X-ray diffraction and TGA/DSC analysis, mass spectrometry, 1H NMR, 13C{1H} NMR and IR spectroscopy is reported. DFT-D calculations have been carried out to assign the absorption band maxima of the IR spectrum to the corresponding vibrational modes. The suitability for Twin Polymerization of the novel dioxagermine 1 has been studied by TGA/DSC analysis and mass spectrometry. Proton-assisted Twin Polymerization of 1 results in an organic-inorganic hybrid material composed of a phenolic resin and [ tBu2GeO]n.

5-Diacetoxymethyl-cycloSal-d4TMP - A prototype of enzymatically activated cyclosal-pronucleotides

A new class of "lock-in"-modified cycloSal-pronucleotides has been synthesized. On the example of 5-diacetoxymethyl-cycloSal-d4T-monophosphate (5-di-AM-cycloSal-d4TMP), the concept of enzymatically activated cycloSal-pronucleotides is elucidated. Synthesis, hydrolysis studies, and antiviral activities against HIV are presented. Copyright Taylor & Francis Group, LLC.

Diels-Alder reaction of 4-bromo-6-spiroepoxycyclohexa-2,4-dienone with electron-rich and neutral dienophiles

Spirodienone 1, prepared by Adler-Becker oxidation of 4-bromo-2- hydroxymethylphenol, undergoes [4+2] cycloaddition with various dienophiles (enol ethers, enol esters, styrenes, N-methylvinylacetamide) under thermal conditions (20-160°C). Three sets of experiments have been carried out, either with CH2Cl2 as solvent or neat with 1, or under tandem oxidation- cycloaddition conditions with phase-transfer catalysis. Complete regio- and syn diastereofacial selectivities were obtained but a switch in endo/exo selectivity has been observed between enol ethers and styrenes (endo addition), enol esters (low selectivity) and an enamide (exo addition). The FMO analysis confirms that theses reactions are under LUMO(diene) control and that the observed regioselectivity is in agreement with orbital coefficients. Except for vinyl acetate, the formation of the major isomer is qualitatively confirmed at the AM1 level.

Asymmetric Retro-Claisen Reaction by Synergistic Chiral Primary Amine/Palladium Catalysis

We described herein a chiral primary amine/palladium catalyzed asymmetric retro-Claisen reaction of β-diketones with salicylic carbonates. A series of chiral α-alkylated ketones and macrolides were obtained with good yields and excellent enantioselectivities upon a sequence of decarboxylative benzylation, retro-Claisen cleavage, and enamine protonation. This strategy features broad substrate scope, mild conditions, as well as high atom economy with salicylic carbonates as the o-quinone methide precursors.

Enthalpies, Free Energies, and Entropies of Transfer of Phenols from Nonpolar Solvents to Water

The enthalpies of transfer of seven phenols from 1-octanol to water and from toluene to water were determined by calorimetry.In the case of two phenols, whose rate of solution in water was found to be too slow for measurement by the usual heat of solution method, a new two-phase titration method was employed.The free energies of transfer between these solvents were determined by measuring the appropriate partition coefficients.The nature of the nonpolar solvent (toluene or 1-octanol) was found to cause large changes in the average values of the thermodynamic parameters of transfer into water, as well as changes in the ordering of the phenols in the series with respect to these transfer parameters.A curious correlation was observed between the octanol-water partition coefficients and the toluene -> water entropies of transfer.

Preparation method of racemic salbutamol

The invention discloses a preparation method of racemic salbutamol. The method comprises the following steps: taking 5-bromosalicylaldehyde as a raw material, carrying out reduction reaction on the 5-bromosalicylaldehyde and sodium borohydride to obtain an intermediate I; carrying out alkylation reaction on the intermediate I, sodium hydride and benzyl halide to obtain an intermediate II; carryingout cross-coupling reaction on the intermediate II and vinyl potassium trifluoroborate to obtain an intermediate III; carrying out addition reaction on the intermediate III and N-bromo succinimide toobtain an intermediate IV; carrying out alkylation reaction on the intermediate IV and tert-butylamine to obtain an intermediate V; and carrying out deprotection reaction on the intermediate V in a hydrogen atmosphere to obtain the racemic salbutamol. The 5-bromosalicylaldehyde is used as a reaction raw material for the first time to reduce the production cost, and bromine atoms are introduced, so that functional groups can be directionally introduced to the 5th site by the reaction, and the selectivity and yield of the reaction are improved; no high-risk highly toxic reagent is involved; andthe Suzuki-Miyaura cross-coupling reaction is applied to synthesis of salbutamol for the first time, and a catalytic amount of palladium catalyst is used, so that efficient introduction of double bonds on an aromatic ring can be realized, and the cost is reduced while the reaction yield is increased.

A synthetic approach to chrysophaentin F

The chrysophaentins are a newly discovered natural product family displaying promising anti-infective activity. Herein we describe an approach to chrysophaentin F that uses an array of metal catalysed coupling reactions (Cu, Ni, Pd, W, Mo) to form key bonds.

New pyrido[3,4-g]quinazoline derivatives as CLK1 and DYRK1A inhibitors: synthesis, biological evaluation and binding mode analysis

Cdc2-like kinase 1 (CLK1) and dual specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) are involved in the regulation of alternative pre-mRNA splicing. Dysregulation of this process has been linked to cancer progression and neurodegenerative diseases, making CLK1 and DYRK1A important therapeutic targets. Here we describe the synthesis of new pyrido[3,4-g]quinazoline derivatives and the evaluation of the inhibitory potencies of these compounds toward CDK5, CK1, GSK3, CLK1 and DYRK1A. Introduction of aminoalkylamino groups at the 2-position resulted in several compounds with low nanomolar affinity and selective inhibition of CLK1 and/or DYRK1A. Their evaluation on several immortalized or cancerous cell lines showed varying degree of cell viability reduction. Co-crystal structures of CLK1 with two of the most potent compounds revealed two alternative binding modes of the pyrido[3,4-g]quinazoline scaffold that can be exploited for future inhibitor design.