2-Allylphenol

Base Information

• Chemical Name: 2-Allylphenol
• CAS No.: 1745-81-9
• Molecular Formula: C9H10O
• Molecular Weight: 134.178
• Hs Code.: 29071900
• European Community (EC) Number: 217-119-0
• NSC Number: 1538
• UNII: O04F145ZJZ
• DSSTox Substance ID: DTXSID3022164
• Nikkaji Number: J34.550D
• Wikidata: Q27093513
• Metabolomics Workbench ID: 122959
• ChEMBL ID: CHEMBL1229950
• Mol file: 1745-81-9.mol

Synonyms:2-allylphenol;2-allylphenol potassium;2-allylphenol sodium

Chemical Property of 2-Allylphenol

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid.
• Vapor Pressure: 0.0783mmHg at 25°C
• Melting Point: -6 °C
• Refractive Index: n20/D 1.546(lit.)
• Boiling Point: 219.999 °C at 760 mmHg
• PKA: pK1: 10.28 (25°C)
• Flash Point: 88.889 °C
• PSA: 20.23000
• Density: 1.014 g/cm³
• LogP: 2.12070
• Storage Temp.: Store below +30°C.
• Solubility.: 7 g/L (20°C)
• Water Solubility.: 7 g/L (20 ºC)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 134.073164938
• Heavy Atom Count: 10
• Complexity: 109

Purity/Quality:

99% ^*data from raw suppliers

2-Allylphenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,C
• Hazard Codes: C,Xi
• Statements: 21/22-34-36/38
• Safety Statements: 26-36/37/39-45-24/25-23

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: C=CCC1=CC=CC=C1O
• Uses: 2-Allylphenol is an protected intermediate in the synthesis of metabolites of Diclofenac (D436450), a nonsteroidal anti-inflammatory compound an decycloxygenase (COX) inhibitor.

Technology Process of 2-Allylphenol

There total 77 articles about 2-Allylphenol 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: 100.0%

allyl phenyl ether (1746-13-0) → o-Allylphenol (1745-81-9)

Guidance literature:

In toluene; at 250 ℃; for 1.75h; microwave irradiation;

DOI:10.1021/jo060692v

Reference yield: 98.0%

2-allyl-1-(trimethylsiloxy)benzene (18042-43-8) → o-Allylphenol (1745-81-9)

Guidance literature:

With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate; at 20 ℃; for 0.0666667h; Green chemistry;

DOI:10.1016/j.molcata.2012.08.002

Reference yield: 92.0%

2-(iodomethyl)-2,3-dihydro-1-benzofuran (59152-49-7) → o-Allylphenol (1745-81-9)

Guidance literature:

With dimethylboron bromide; tetra-(n-butyl)ammonium iodide; triethylamine; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1016/S0040-4039(00)96843-6

upstream raw materials:

quinoline

4-hydroxy-3-allyl-benzoic acid

diphenylether

allyl phenyl ether

Downstream raw materials:

2-methyl-2,3-dihydro-1-benzofuran

3-allylsalicylaldehyde

5-allyl-4-hydroxy-isophthalaldehyde

2-allylphenyl acetate

Refernces

• 1、 Kistiakowsky,Tichenor. "-". . p. 2302. Retrieved 1942.
• 2、 Somerville, Kristina,Tilley, Michael,Li, Guanlong,Mallik, Debasis,Organ, Michael G.. "A flow reactor with inline analytics: Design and implementation". . p. 1315 - 1320. Retrieved 2014.
• 3、 Sauks, Jennifer M.,Mallik, Debasis,Lawryshyn, Yuri,Bender, Timothy,Organ, Michael. "A continuous-flow microwave reactor for conducting high-temperature and high-pressure chemical reactions". . p. 1310 - 1314. Retrieved 2014.
• 4、 Sato, Masahiro,Otabe, Nobuhiro,Tuji, Tomoya,Matsushima, Keiichiro,Kawanami, Hajime,Chatterjee, Maya,Yokoyama, Toshiro,Ikushima, Yutaka,Suzuki, Toshishige Maro. "Highly-selective and high-speed Claisen rearrangement induced with subcritical water microreaction in the absence of catalyst". . p. 763 - 766. Retrieved 2009.
• 5、 Le Noble. "-". . p. 1470. Retrieved 1963.
• 6、 Miller,Wood. "-". . p. 39. Retrieved 1965.
• 7、 Iwakura, Izumi,Yabushita, Atsushi,Kobayashi, Takayoshi. "Non-thermal reaction triggered by a stimulated Raman process using 5-fs laser pulses in the electronic ground state: Claisen rearrangement of allyl phenyl ether". . p. 567 - 571. Retrieved 2011.
• 8、 Priede, Elina,Nakurte, Ilva,Zicmanis, Andris. "Structure effect of imidazolium-based dicationic ionic liquids on claisen rearrangement". . p. 1803 - 1809. Retrieved 2014.
• 9、 Mathew, Nevin T.,Khaire,Mayadevi,Jha,Sivasanker. "Rearrangement of allyl phenyl ether over Al-MCM-41". . p. 105 - 113. Retrieved 2005.
• 10、 Kupczyk-Subotkowska, Lidia,Subotkowski, Witold,Saunders, William H.,Shine, Henry J.. "Claisen Rearrangement of Allyl Phenyl Ether. 1-14C and β-14C Kinetic Isotope Effects. A Clearer View of the Transition Structure". . p. 3441 - 3445. Retrieved 1992.