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[ CAS No. 2491-38-5 ] {[proInfo.proName]}

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Chemical Structure| 2491-38-5
Chemical Structure| 2491-38-5
Structure of 2491-38-5 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Details of [ 2491-38-5 ]

CAS No. :2491-38-5 MDL No. :MFCD00072424
Formula : C8H7BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :LJYOFQHKEWTQRH-UHFFFAOYSA-N
M.W : 215.04 Pubchem ID :4964
Synonyms :
α-Bromo-4-hydroxyacetophenone; 2-Bromo-4'-hydroxyacetophenone; 4-Hydroxyphenacyl bromide; 4-Hydroxyphenacyl bromide; SHP-1 Inhibitor II
Chemical Name :2-Bromo-1-(4-hydroxyphenyl)ethanone

Calculated chemistry of [ 2491-38-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.53
TPSA : 37.3 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.39
Log Po/w (XLOGP3) : 1.83
Log Po/w (WLOGP) : 1.97
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 2.21
Consensus Log Po/w : 1.8

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.6
Solubility : 0.543 mg/ml ; 0.00252 mol/l
Class : Soluble
Log S (Ali) : -2.23
Solubility : 1.26 mg/ml ; 0.00584 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.04
Solubility : 0.198 mg/ml ; 0.000923 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.4

Safety of [ 2491-38-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P270-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P406-P405 UN#:3261
Hazard Statements:H302-H314-H290 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2491-38-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 2491-38-5 ]
  • Downstream synthetic route of [ 2491-38-5 ]

[ 2491-38-5 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 2491-38-5 ]
  • [ 124-41-4 ]
  • [ 32136-81-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 1, p. 55 - 59
[2] Chemical Communications, 2015, vol. 51, # 34, p. 7349 - 7351
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 191 - 194
[4] Patent: WO2004/52816, 2004, A1, . Location in patent: Page 38
[5] Patent: WO2004/113273, 2004, A1, . Location in patent: Page 37
  • 2
  • [ 2491-38-5 ]
  • [ 32136-81-5 ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydroxide In methanol EXAMPLE 3
Preparation of alpha-methoxy-4-hydroxyacetophenone
2 g of alpha-bromo-4-hydroxyacetophenone are dissolved in 11 g of methanol.
30 g of a saturated solution of sodium hydroxide in methanol (1 g NaOH/ 4.2 ml methanol) is added dropwise to the alpha-bromo-4-hydroxyacetophenone solution.
After the addition is complete, the solution is added to 30 g of ice and acidified to pH 6.
Alpha-methoxy-4-hydroxyacetophenone precipitates out and is filtered and dried to a greenish yellow product in about 85percent yield; the product is determined by 1-H-NMR to be substantially pure.
Reference: [1] Patent: US5107034, 1992, A,
  • 3
  • [ 2491-38-5 ]
  • [ 7440-44-0 ]
  • [ 32136-81-5 ]
Reference: [1] Patent: US5107034, 1992, A,
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Technical Information

? Acidity of Phenols ? Alkyl Halide Occurrence ? Appel Reaction ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Chugaev Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Halogenation of Phenols ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Jones Oxidation ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Martin's Sulfurane Dehydrating Reagent ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Oxidation of Phenols ? Passerini Reaction ? Paternò-Büchi Reaction ? Pechmann Coumarin Synthesis ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Alcohols ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Alcohols ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Reimer-Tiemann Reaction ? Ritter Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Swern Oxidation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
Historical Records

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