5-Cyanophthalide

Base Information

• Chemical Name: 5-Cyanophthalide
• CAS No.: 82104-74-3
• Molecular Formula: C9H5NO2
• Molecular Weight: 159.144
• Hs Code.: 29322090
• European Community (EC) Number: 279-900-2
• DSSTox Substance ID: DTXSID40868641
• Nikkaji Number: J320.372G
• Wikidata: Q72458955
• Mol file: 82104-74-3.mol

Synonyms:5-Cyanophthalide;82104-74-3;1-Oxo-1,3-dihydroisobenzofuran-5-carbonitrile;1-oxo-3H-2-benzofuran-5-carbonitrile;5-cyano phthalide;1-oxo-1,3-dihydro-2-benzofuran-5-carbonitrile;1,3-Dihydro-1-oxoisobenzofuran-5-carbonitrile;5-Isobenzofurancarbonitrile, 1,3-dihydro-1-oxo-;EINECS 279-900-2;MFCD01072882;EC 279-900-2;5-Cyanophthalid;5-Cyanophthalide, 97%;SCHEMBL1641;DTXSID40868641;AMY40169;BCP13095;AC9502;AKOS015836116;AC-5340;CS-W016184;AS-11983;BP-12876;SY051382;C2001;Diethyl 1-butylpyrrolidine-2,5-dicarboxylate;FT-0620351;EN300-396646;A840246;AR-011/40257489;W-104188

Chemical Property of 5-Cyanophthalide

Chemical Property:

• Appearance/Colour: white to pale yellow crystalline solid
• Vapor Pressure: 7.53E-07mmHg at 25°C
• Melting Point: 201-205 °C(lit.)
• Refractive Index: 1.606
• Boiling Point: 407.5 °C at 760 mmHg
• Flash Point: 199.3 °C
• PSA: 50.09000
• Density: 1.36 g/cm³
• LogP: 1.22868
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.5
• 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:

99% ^*data from raw suppliers

5-Cyanophthalide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36/37-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(C=CC(=C2)C#N)C(=O)O1
• Uses: 5-Cyanophthalide is a useful synthetic intermediate.

Technology Process of 5-Cyanophthalide

There total 19 articles about 5-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: 91.0%

5-hydroxamyl phthalide (934473-85-5) → 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile (82104-74-3)

Guidance literature:

With thionyl chloride; at 80 ℃; for 6h; Product distribution / selectivity; Heating / reflux;

Reference yield: 89.5%

5-carboxyphtalide (4792-29-4) → 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile (82104-74-3)

Guidance literature:

5-carboxyphtalide; With ethyl phosphate; ammonium carbonate; In acetonitrile; at 0 - 25 ℃; for 6h;

at 90 - 95 ℃; for 12h;

Reference yield: 84.0%

potassium cyanide + 5-bromophthalide (64169-34-2) → 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile (82104-74-3)

Guidance literature:

potassium cyanide; With acetic acid; In ethylene glycol; at 20 ℃; Sealed tube;

5-bromophthalide; With P(t-Bu)3 Palladacycle Gen_. 3; potassium acetate; In 1,4-dioxane; water; at 60 ℃; for 16h; Sealed tube;

DOI:10.1039/c7sc03912c

upstream raw materials:

5-amino-3H-isobenzofuran-1-one

1-oxo-3-hydroxy-1,3-dihydro-N-phenylisoindole-5-carbonitrile

4-cyanobenzanilide

4-cyanobenzoyl chlorIde

Downstream raw materials:

1-oxo-1,3-dihydroisobenzofuran-5-carboxamide

1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile

4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile

4-(bis(4-fluorophenyl)hydroxymethyl)-3-(hydroxymethyl)benzonitrile

Refernces

• 1、 Chen, Hui,Sun, Shuhao,Liu, Yahu A.,Liao, Xuebin. "Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C-CN Bond Cleavage and Cyano Transfer". . p. 1397 - 1405. Retrieved 2020/02/04.
• 2、 Kristensen, Steffan K.,Eikeland, Espen Z.,Taarning, Esben,Lindhardt, Anders T.,Skrydstrup, Troels. "Ex situ generation of stoichiometric HCN and its application in the Pd-catalysed cyanation of aryl bromides: Evidence for a transmetallation step between two oxidative addition Pd-complexes". . p. 8094 - 8105. Retrieved 2017/11/27.