2'-Hydroxyacetophenone

Base Information

• Chemical Name: 2'-Hydroxyacetophenone
• CAS No.: 118-93-4
• Molecular Formula: C8H8O2
• Molecular Weight: 136.15
• Hs Code.: 29145000
• European Community (EC) Number: 204-288-0
• NSC Number: 44452,16933,9263
• UNII: 3E533Z76W0
• DSSTox Substance ID: DTXSID7040285
• Nikkaji Number: J5.308B
• Wikidata: Q27257104
• Metabolomics Workbench ID: 45613
• ChEMBL ID: CHEMBL3187012
• Mol file: 118-93-4.mol

Synonyms:Acetophenone,2'-hydroxy- (8CI);Acetophenone, o-hydroxy- (3CI);1-(2-Hydroxyphenyl)ethanone;1-(6-Hydroxyphenyl)ethanone;2-Acetylphenol;2-Hydroxyphenyl methyl ketone;2-Hydroxyphenylethanone;2'-Hydroxyacetophenone;Methyl 2-hydroxyphenyl ketone;NSC 16933;NSC 44452;NSC 83568;NSC 9263;o-Acetylphenol;o-Hydroxyacetophenone;o-Hydroxyhypnone;o-Hydroxyphenyl methyl ketone;

Chemical Property of 2'-Hydroxyacetophenone

Chemical Property:

• Appearance/Colour: Light yellow liquid
• Vapor Pressure: ~0.2 mm Hg ( 20 °C)
• Melting Point: 3-6 °C(lit.)
• Refractive Index: n20/D 1.558(lit.)
• Boiling Point: 218.4 °C at 760 mmHg
• PKA: 10.06(at 25℃)
• Flash Point: 87.5 °C
• PSA: 37.30000
• Density: 1.131 g/cm³
• LogP: 1.59480
• Storage Temp.: Store below +30°C.
• Solubility.: 0.2g/l
• Water Solubility.: slightly soluble
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 136.052429494
• Heavy Atom Count: 10
• Complexity: 131

Purity/Quality:

99% ^*data from raw suppliers

2’-Hydroxyacetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones
• Canonical SMILES: CC(=O)C1=CC=CC=C1O
• Description: It is a typical flavour additive for cherry kernel, cinnamon, rum, tobacco, coumarin, and tropical fruit. Moreover, it can be used as the intermediate or raw material in organic synthesis. Specifically, this chemical may act as the raw material to prepare a Schiff’s base al-alkoxide initiator that facilitates the controlled polymerization of DL-lactide.1 This substance can also function as the effective component in balsamic compounds for fabricating taste modifying compositions.2 Additionally, this chemical has been employed to react with benzoyl chloride for generating 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran, which exhibits good performance for treating cancer and other proliferative diseases such as psoriasis and restenosis.3
• Uses: 2'-Hydroxyacetophenone is used as pharmaceutical intermediate. 2’Hydroxyacetophenone is a phenolic compound used in the synthesis of potential anti-myobacterial and anticancer agents.

Technology Process of 2'-Hydroxyacetophenone

There total 224 articles about 2'-Hydroxyacetophenone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.0%

2-(2-hydroxy-4-phenylbut-3-yn-2-yl)phenol → 1,4-diphenyl-1,3-butadiyne (886-66-8) + o-hydroxyacetophenone (118-93-4,104809-67-8)

Guidance literature:

With copper(II) acetate monohydrate; In acetonitrile; for 4h; Reflux;

DOI:10.3184/174751913X13739011239995

Reference yield: 47.0%

phenylethane 1,2-diol (93-56-1) → methyl 2-oxo-2-phenylacetate (15206-55-0) + o-hydroxyacetophenone (118-93-4,104809-67-8) + Benzoylformic acid (611-73-4)

Guidance literature:

With sodium tetrahydroborate; 1% Pd/C; water; potassium hydroxide; In methanol; at 20 ℃; for 9h; In air;

DOI:10.1055/s-0029-1217115

Reference yield: 45.0%

2-(1-hydroxyethyl)phenol (87804-23-7,62019-23-2) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + o-hydroxyacetophenone (118-93-4,104809-67-8) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9)

Guidance literature:

With Amberlite IRA-120; urea-hydrogen peroxide; 1-n-butyl-3-methylimidazolim bromide; at 70 ℃; for 0.916667h;

DOI:10.1246/cl.2008.496

upstream raw materials:

3-methyl-benzofuran

1-benzopyran-4(4H)-one

sodium ethanolate

methyl magnesium iodide

Downstream raw materials:

2-chloro-2'-hydroxychalcone

1-(2-hydroxy-phenyl)-3-piperidin-1-yl-propan-1-one

2-(2-hydroxyphenyl)-1,8-naphthyridine

1-(2-hydroxyphenyl)-3-(5-nitro-2-furyl)-2-propen-1-one

Refernces

• 1、 Kathe, Prasad M.,Berkefeld, Andreas,Fleischer, Ivana. "Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization". supporting information. p. 1629 - 1632. Retrieved 2021/02/09.
• 2、 Dandia, Anshu,Saini, Pratibha,Chithra,Vennapusa, Sivaranjana Reddy,Parewa, Vijay. "Catalyst- and acid-free Markovnikov hydration of alkynes in a sustainable H2O/ethyl lactate system". . . Retrieved 2021/03/15.