Cyanophthalide

Base Information

• Chemical Name: Cyanophthalide
• CAS No.: 27613-27-0
• Molecular Formula: C9H5NO2
• Molecular Weight: 159.144
• Hs Code.: 2932209090
• European Community (EC) Number: 621-994-8
• DSSTox Substance ID: DTXSID60454560
• Nikkaji Number: J660.736E
• Mol file: 27613-27-0.mol

Synonyms:cyanophthalide;27613-27-0;3-Cyanophthalide;3-Oxo-1,3-dihydroisobenzofuran-1-carbonitrile;3-OXO-1H-2-BENZOFURAN-1-CARBONITRILE;3-oxo-1,3-dihydro-2-benzofuran-1-carbonitrile;3-oxo-1H-isobenzofuran-1-carbonitrile;starbld0033109;3-Cyanophthalide, 98%;1,3-Dihydro-3-oxo-1-isobenzofurancarbonitrile;1-Isobenzofurancarbonitrile, 1,3-dihydro-3-oxo-;SCHEMBL111858;DTXSID60454560;PUIVIZQHTBRFTR-UHFFFAOYSA-N;CBA61327;CS-0498584

Chemical Property of Cyanophthalide

Chemical Property:

• Melting Point: 120-121 °C(Solv: ethanol (64-17-5); hexane (110-54-3))
• Boiling Point: 394.1±42.0 °C(Predicted)
• PSA: 50.09000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: 1.42168
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 159.032028402
• Heavy Atom Count: 12
• Complexity: 253

Purity/Quality:

3-Cyanophthalide 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 4292885
• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(OC2=O)C#N

Technology Process of Cyanophthalide

There total 13 articles about Cyanophthalide 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: 96.0%

potassium cyanide (151-50-8) + o-carboxybenzaldehyde (119-67-5) → 3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile (27613-27-0)

Guidance literature:

With hydrogenchloride; dicyclohexyl-carbodiimide;

Reference yield: 91.0%

2-benzofuran-1(3H)-one (87-41-2) + sodium cyanide (143-33-9,25596-52-5) → 3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile (27613-27-0)

Guidance literature:

With PEG₄₀₀; at 150 ℃; for 12h;

DOI:10.1081/SCC-100104474

Reference yield: 85.0%

3-hydroxy-1(3H)-isobenzofuranone (16859-59-9) + potassium cyanide (151-50-8) → 3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile (27613-27-0)

Guidance literature:

3-hydroxy-1(3H)-isobenzofuranone; potassium cyanide; With hydrogenchloride; at 0 ℃; for 0.666667h;

With dicyclohexyl-carbodiimide; In ethyl acetate; for 8h;

DOI:10.1002/hlca.200390058

upstream raw materials:

2-(Cyano-hydroxy-methyl)-benzoic acid

2-(Cyano-trimethylsilanyloxy-methyl)-N,N-diethyl-benzamide

2-benzofuran-1(3H)-one

sodium cyanide

Downstream raw materials:

1,3-dimethoxy-9,10-anthraquinone

1,4-dimethoxyanthraquinone

1,4-difluoroanthracene-9,10-dione

1,4-dihydroxy-9,10-anthracenedione

Refernces

• 1、 Sk, Md Raja,Chakraborty, Soumen,Mal, Dipakranjan. "Studies directed toward total synthesis of rhodocomatulins: A regioselective synthesis of brominated hydroxyanthraquinones by anionic annulations". . p. 309 - 317. Retrieved 2018/02/09.
• 2、 Sakulsombat, Morakot,Angelin, Marcus,Ramstr?m, Olof. "Tandem reversible addition-intramolecular lactonization for the synthesis of 3-functionalized phthalides". supporting information; experimental part. p. 75 - 78. Retrieved 2010/03/01.