ANISOIN

Base Information

• Chemical Name: ANISOIN
• CAS No.: 119-52-8
• Molecular Formula: C16H16O4
• Molecular Weight: 272.301
• Hs Code.: 2914.50 DERIVATION
• European Community (EC) Number: 204-330-8
• NSC Number: 8504,7960
• DSSTox Substance ID: DTXSID60883311
• Nikkaji Number: J312C
• ChEMBL ID: CHEMBL370299
• Mol file: 119-52-8.mol

Synonyms:p-Anisoin(7CI,8CI);(?à)-p-Anisoin;1-Oxo-1,2-bis(p-methoxyphenyl)-2-hydroxyethane;2-Hydroxy-1,2-bis(4-methoxyphenyl)ethanone;4,4'-Dimethoxybenzoin;NSC 7960;NSC 8504;p,p'-Dimethoxybenzoin;

Chemical Property of ANISOIN

Chemical Property:

• Appearance/Colour: pale yellow to beige powder
• Vapor Pressure: 3.11E-09mmHg at 25°C
• Melting Point: 108-111 °C(lit.)
• Refractive Index: 1.578
• Boiling Point: 459.373 °C at 760 mmHg
• PKA: 12.14±0.20(Predicted)
• Flash Point: 170.967 °C
• PSA: 55.76000
• Density: 1.195 g/cm³
• LogP: 2.62010
• Storage Temp.: Store below +30°C.
• Water Solubility.: Soluble in water, ethanol and acetone.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 272.10485899
• Heavy Atom Count: 20
• Complexity: 302

Purity/Quality:

99.5% ^*data from raw suppliers

2-Hydroxy-1,2-bis(4-methoxyphenyl)ethanone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: COC1=CC=C(C=C1)C(C(=O)C2=CC=C(C=C2)OC)O
• Uses: Anisoin is a useful pre-chromatographic derivatization fluorogenic reagent for LC (liquid chromatography) analysis of guanidino compounds. It is widely used as photoinitiators in polymerization reactions. It is widely used in UV curing inks, wood coatings, paper coatings, optical fiber, PCB, screen printing, paper varnish and other surfaces.

Technology Process of ANISOIN

There total 81 articles about ANISOIN 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: 98.0%

1,2-bis-(4-methoxyphenyl)-2-[(trimethylsilyl)oxy]ethanone (28698-07-9) → 4,4'-dimethoxybenzoin (119-52-8)

Guidance literature:

With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate; at 20 ℃; for 0.0833333h; Green chemistry;

DOI:10.1016/j.molcata.2012.08.002

Reference yield: 95.0%

4-methoxy-benzaldehyde (123-11-5) → 4,4'-dimethoxybenzoin (119-52-8)

Guidance literature:

With 1,3-dimethylbenzimidazolium Iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; for 1.5h; Heating;

DOI:10.1248/cpb.42.2633

Reference yield: 94.0%

1,2-bis(4-methoxyphenyl)-1,2-ethanedione (1226-42-2) → 4,4'-dimethoxybenzoin (119-52-8)

Guidance literature:

With ammonium chloride; zinc; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1007/s706-002-8250-y

upstream raw materials:

1,2-dimethoxyethane

4-methoxy-benzaldehyde

potassium cyanide

1,2-bis(4-methoxyphenyl)-1,2-ethanedione

Downstream raw materials:

4,4'-dimethoxy-α-pyrrolidino-deoxybenzoin

1,2-bis(4-methoxyphenyl)-2-oxoethyl acetate

(E)-1,2-Bis(4-methoxyphenyl)-1,2-bis(methylthio)ethylen

1,2-bis(4-methoxyphenyl)-1,2-ethanedione

Refernces

• 1、 Haghighi, Ali Javaheri,Mokhtari, Javad,Karimian, Khashayar. "N-PEGylated Thiazolium Salt: A Green and Reusable Homogenous Organocatalyst for the Synthesis of Benzoins and Acyloins". . p. 1646 - 1652. Retrieved 2021.
• 2、 Qiu,Chen,Zhang,Zhou. "Partial reduction of α-diketones by sodium hydrogen selenide". . p. 1529 - 1534. Retrieved 1992.
• 3、 Liu, Yongjun,Xu, Xiaoliang,Zhang, Yongmin. "Direct Formation of Benzoins from Diarylmethanones via a Rearrangement Reaction Promoted by Samarium Metal in DMF". . p. 445 - 448. Retrieved 2004.
• 4、 Seo, Ue Ryung,Chung, Young Keun. "Poly(4-vinylimidazolium) iodides: A highly recyclable organocatalyst precursor for benzoin condensation reaction". . p. 32371 - 32374. Retrieved 2014.
• 5、 Lappert, Michael F.,Maskell, Robin K.. "A New Class of Benzoin Condensation Catalyst, the Bi-(1,3-dialkylimidazolidin-2-ylidenes)". . p. 580 - 581. Retrieved 1982.
• 6、 Fragnelli, Maria Caterina,Hoyos, Pilar,Romano, Diego,Gandolfi, Raffaela,Alcántara, Andrés R.,Molinari, Francesco. "Enantioselective reduction and deracemisation using the non-conventional yeast Pichia glucozyma in water/organic solvent biphasic systems: Preparation of (S)-1,2-diaryl-2-hydroxyethanones (benzoins)". . p. 523 - 528. Retrieved 2012.
• 7、 Gerhardt. "-". . p. 270. Retrieved 1845.
• 8、 Ma, Shuang,Toy, Patrick H.. "Self-supported N-heterocyclic carbenes and their use as organocatalysts". . . Retrieved 2016.
• 9、 Rafiński, Zbigniew. "Enantioselective benzoin condensation catalyzed by spirocyclic terpene-based N-heterocyclic carbenes". . p. 1860 - 1867. Retrieved 2016.
• 10、 Liao, Jian,Zhang, Yili,Li, Zhi,Chen, Daimo,Chan, Albert S. C.. "Preparation of optically pure (1r,2s)- and (1s,2r)-di-p-methoxyphenyl amino alcohol". . p. 3465 - 3472. Retrieved 2000.