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2',3'-DIHYDROXYACETOPHENONE is an organic compound that serves as a key intermediate in the synthesis of various pharmaceutical compounds. It is characterized by the presence of two hydroxyl groups at the 2' and 3' positions of the acetophenone molecule, which allows for further chemical modifications and functionalization.

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  • 13494-10-5 Structure
  • Basic information

    1. Product Name: 2',3'-DIHYDROXYACETOPHENONE
    2. Synonyms: 2',3'-DIHYDROXYACETOPHENONE;3-Acetylcatechol;1-(2,3-dihydroxyphenyl)ethan-1-one;3-Acetyl-1,2-benzenediol;Ethanone,1-(2,3-dihydroxyphenyl)-
    3. CAS NO:13494-10-5
    4. Molecular Formula: C8H8O3
    5. Molecular Weight: 152.15
    6. EINECS: N/A
    7. Product Categories: Aromatics;Intermediates
    8. Mol File: 13494-10-5.mol
  • Chemical Properties

    1. Melting Point: 198-200℃
    2. Boiling Point: 294 °C at 760 mmHg
    3. Flash Point: 145.9 °C
    4. Appearance: /
    5. Density: 1.291g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: Sealed in dry,Room Temperature
    8. Solubility: Chloroform, Methanol
    9. PKA: 8.98±0.10(Predicted)
    10. CAS DataBase Reference: 2',3'-DIHYDROXYACETOPHENONE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 2',3'-DIHYDROXYACETOPHENONE(13494-10-5)
    12. EPA Substance Registry System: 2',3'-DIHYDROXYACETOPHENONE(13494-10-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: 36/37/38
    3. Safety Statements: 26-36/37/39
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 13494-10-5(Hazardous Substances Data)

13494-10-5 Usage

Uses

Used in Pharmaceutical Industry:
2',3'-DIHYDROXYACETOPHENONE is used as a reagent for the synthesis of antiproliferative agents, which are compounds that inhibit cell proliferation and are often used in cancer treatment. Its role in the synthesis of these agents is due to its ability to be chemically modified and incorporated into the structure of the final product.
2',3'-DIHYDROXYACETOPHENONE is also used as a reagent for the synthesis of opioid receptor agonists, which are drugs that bind to and activate opioid receptors in the nervous system. These agonists are used to treat pain and are also involved in the management of addiction and other neurological disorders.
Furthermore, 2',3'-DIHYDROXYACETOPHENONE is used in the synthesis of anticoagulants, which are medications that help prevent blood clots from forming. These compounds are essential in the treatment and prevention of conditions such as deep vein thrombosis, pulmonary embolism, and stroke.

Preparation

Also obtained by bioconversion of acetophenone through the living cells of Escherichia coli carrying plasmid pUC6256B expressing todCI-bphA2A3A4 and bphB (39.2%).

Check Digit Verification of cas no

The CAS Registry Mumber 13494-10-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,4,9 and 4 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 13494-10:
(7*1)+(6*3)+(5*4)+(4*9)+(3*4)+(2*1)+(1*0)=95
95 % 10 = 5
So 13494-10-5 is a valid CAS Registry Number.

13494-10-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(2,3-Dihydroxyphenyl)ethanone

1.2 Other means of identification

Product number -
Other names 2',3'-Dihydroxyacetophenone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13494-10-5 SDS

13494-10-5Relevant articles and documents

Synthetic method of benzodioxole derivative

-

Paragraph 0024-0025, (2021/02/13)

The invention provides a synthetic method of a benzodioxole derivative, which is used for preparing a 7-bromobenzo [ D ] [1,3] dioxol-4-one benzodioxole derivative through acylation reaction, substitution reaction and reaction with dihalomethane. The meth

Extensive structure modification on luteolin-cinnamic acid conjugates leading to BACE1 inhibitors with optimal pharmacological properties

Sun, De-Yang,Cheng, Chen,Moschke, Katrin,Huang, Jian,Fang, Wei-Shuo

, (2020/01/13)

BACE1 inhibitory conjugates derived from two natural products, luteolin (1) and p-hydroxy-cinnamic acid (2), were subjected to systematic structure modifications, including various positions in luteolin segment for conjugation, different linkers (length, bond variation), as well as various substitutions in cinnamic acid segment (various substituents on benzene, and replacement of benzene by heteroaromatics and cycloalkane). Optimal conjugates such as 7c and 7k were chosen on the basis of a series of bioassay data for further investigation.

Solvent Dependence of the Monomer–Dimer Equilibrium of Ketone-Substituted Triscatecholate Titanium(IV) Complexes

Kwamen, A. Carel N.,Jenniches, Judith,Oppel, Iris M.,Albrecht, Markus

, p. 10550 - 10554 (2020/07/24)

Hierarchical helicates based on ketone-substituted titanium(IV)triscatecholates show different monomer-dimer behavior depending on different solvents. The dimerization constants of a whole series of differently alkyl-substituted complexes is analyzed to show that the solvent has a very strong influence on the dimerization. Hereby, effects like solvophobicity/philicity, sterics, electronics of the substituents and weak side-chain—side-chain interactions seem to act in concert.

Practical and efficient synthesis of hydroxyaryl ketones catalyzed by HF@SiO2 under solvent-free condition

Paghandeh, Hossein,Saeidian, Hamid,Ghaffarzadeh, Mohammad

, p. 809 - 814 (2018/09/26)

A wide variety of hydroxyaryl ketones bearing different motifs was successfully synthesized with good yields and excellent selectivities in the presence of HF@SiO2 as an environmental friendly acid under solvent-free condition. Mild and green reaction conditions and excellent yields (50-91%) make this method an attractive method for the efficient synthesis of hydroxyaryl ketones. Fries rearrangement of phenyl benzoate in the presence of HF@SiO2 led to p-hydroxybenzophenone, while phenyl acetate in the same conditions produced o-hydroxyacetophenone as a single isomer.

LYSYL OXIDASE-LIKE 2 INHIBITORS AND USES THEREOF

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Paragraph 00387, (2017/02/24)

Described herein are compounds that are LOXL2 inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with LOXL2 activity.

Catalytic application of fluorous silica gel in Fries rearrangement

Ghaffarzadeh, Mohammad,Ahmadi, Maryam

, p. 77 - 81 (2014/03/21)

Commercially available fluorous silica gel (Fluoro Flash) with no further post-modification was successfully investigated and applied merely as a catalyst in Fries rearrangement of various aryl esters under solvent free conditions in 4 h and optimized temperatures. In addition to good yields and recyclability of the catalyst, toxicity of reaction medium, by-products, and wastes were minimized. Also, low catalyst loading was another advantage of this methodology.

SYNTHESIS AND ANTICANCER ACTIVITY OF ARYL AND HETEROARYL-QUINOLIN DERIVATIVES

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Page/Page column 16-17, (2012/02/01)

A compound of Formula I is disclosed as follows: or a pharmaceutically acceptable salt, prodrug, solvate, or metabolite thereof, wherein R is hydrogen, P(═O)(OH)2, P(═O)(O(C1-C18)alkylene(C6-C20)aryl)2, P(═O)(OH)(OM), P(═O)(OM)2, P═O(O2M), S(═O)(OH)2, S(═O)(O(C1-C18)alkylene(C6-C20)aryl)2, S(═O)(OH)(OM), S(═O)(OM)2; M is a monovalent or divalent metal ion, or alkylammonium ion; W is (C6-C20)aryl, (C6-C20)heteroaryl, (C1-C18)alkyl(C6-C20)aryl, (C1-C18)alkyl(C6-C20)heteroaryl, hydroxy(C6-C20)aryl, hydroxy(C6-C20)heteroaryl, (C1-C18)alkoxy(C6-C20)aryl, (C1-C18)alkoxy(C6-C20)heteroaryl, (C1-C18)alkylenedioxy(C6-C20)aryl, (C1-C18)alkylenedioxy(C6-C20)heteroaryl, halo(C6-C20)aryl, halo(C6-C20)heteroaryl, (C1-C18)alkylamino(C6-C20)aryl, (C1-C18)alkylamino(C6-C20)heteroaryl, (C1-C18)cycloalkylamino(C6-C20)aryl, or (C1-C18)cycloalkylamino(C6-C20)heteroaryl, and their OR8 substutes; R5 is (C1-C18alkoxy, hydrogen, hydroxyl, O—(C1-C18)alkyl(C6-C20)aryl, halo or OR8, or R5 and R6 are (C1-C18)dioxy provided that R7 is hydrogen; R6 is hydroxyl, O—(C1-C18)alkyl(C6-C20)aryl, halo or ORR, (C1-C18)alkoxy, (C1-C18)alkylamino, or (C1-C18)cycloalkylamino, or R6 and R7 are (C1-C18)dioxy provided that R5 is hydrogen; R7 is hydrogen, halo or OR8, hydroxyl, or O—(C1-C18)alkyl(C6-C20)aryl; and R8 is P(═O)(OH)2, P(═O)(O(C1-C18)alkyl(C6-C20)aryl)2, P(═O)(OH)(OM), or P(═O)(OM)2, P═O(O2M).

Preparative monohydroxyflavanone syntheses and a protocol for gas chromatography-mass spectrometry analysis of monohydroxyflavanones

Kagawa, Hitoshi,Shigematsu, Asako,Ohta, Shigeru,Harigaya, Yoshihiro

, p. 547 - 554 (2007/10/03)

We describe a facile efficient, and preparative approach for monohydroxyflavanone syntheses. Using this protocol, a hydroxyl is regio-selectively introduced at one carbon of a flavanone A- or B-ring per synthesis. The seven possible isomers were each synthesized from the corresponding monomethoxymethoxylated 2′-hydroxychalcones in acidic solution. These monohydroxyflavanones were characterized using a gas chromatography-mass spectrometry (GC-MS) system that incorporated a DB-5 capillary column. Ours is the first report of a preparative synthetic method during which a single hydroxyl can be selectively added to a flavanone A- or B-ring at any position. We are also the first to develop a procedure that separates the seven isomers by GC and characterizes the mass spectra of the isomers. Both the synthetic method and the GC-MS conditions may become important tools during future flavanone metabolism and oxidation studies.

Hierarchical assembly of helicate-type dinuclear titanium(IV) complexes

Albrecht, Markus,Mirtschin, Sebastian,De Groot, Marita,Janser, Ingo,Runsink, Jan,Raabe, Gerhard,Kogej, Michael,Schalley, Christoph A.,Froehlich, Roland

, p. 10371 - 10387 (2007/10/03)

The ligands 4-7-H2 were used in coordination studies with titanium(IV) and gallium(III) ions to obtain dimeric complexes Li 4[(4-7)6Ti2] and Li6[(4/5a) 6Ga2]. The X-ray crystal structures of Li 4[(4)6Ti2], Li4[(5b) 6Ti2], and Li4[(7a)6Ti2] could be obtained. While these complexes are triply lithium-bridged dimers in the solid state, a monomer/dimer equilibrium is observed in solution by NMR spectroscopy and ESI FT-ICR MS. The stability of the dimer is enhanced by high negative charges (Ti(IV) versus Ga(III)) of the monomers, when the carbonyl units are good donors (aldehydes versus ketones and esters), when the solvent does not efficiently solvate the bridging lithium ions (DMSO versus acetone), and when sterical hindrance is minimized (methyl versus primary and secondary carbon substituents). The dimer is thermodynamically favored by enthalpy as well as entropy. ESI FT-ICR mass spectrometry provides detailed insight into the mechanisms with which monomeric triscatecholate complexes as well as single catechol ligands exchange in the dimers. Tandem mass spectrometric experiments in the gas phase show the dimers to decompose either in a symmetric (Ti) or in an unsymmetric (Ga) fashion when collisionally activated. The differences between the Ti and Ga complexes can be attributed to different electronic properties and a charge-controlled reactivity of the ions in the gas phase. The complexes represent an excellent example for hierarchical self-assembly, in which two different noncovalent interactions of well balanced strengths bring together eleven individual components into one well-defined aggregate.

Microwave assisted direct ortho-acylation of phenol and naphthol derivatives by BF3·(C2H5)2O

Naeimi, Hossein,Moradi, Leila

, p. 284 - 287 (2008/02/04)

The solventless acylation of phenol and naphthol derivatives with various organic acids and BF3·(C2H5) 2O, under microwave conditions, was studied. High yields of the o-acylated products were achieved in a very short time.

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