Product Name

  • Name

    5-Cyanophthalide

  • EINECS 279-900-2
  • CAS No. 82104-74-3
  • Article Data15
  • CAS DataBase
  • Density 1.36 g/cm3
  • Solubility
  • Melting Point 201-205 °C(lit.)
  • Formula C9H5NO2
  • Boiling Point 407.5 °C at 760 mmHg
  • Molecular Weight 159.144
  • Flash Point 199.3 °C
  • Transport Information
  • Appearance white to pale yellow crystalline solid
  • Safety 36/37-36-26
  • Risk Codes 20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 82104-74-3 (5-Cyanophthalide)
  • Hazard Symbols HarmfulXn, IrritantXi
  • Synonyms 1,3-Dihydro-1-oxoisobenzofuran-5-carbonitrile;
  • PSA 50.09000
  • LogP 1.22868

Synthetic route

5-hydroxamyl phthalide
934473-85-5

5-hydroxamyl phthalide

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
With thionyl chloride at 80℃; for 6h; Product distribution / selectivity; Heating / reflux;91%
5-carboxyphtalide
4792-29-4

5-carboxyphtalide

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
Stage #1: 5-carboxyphtalide With ethyl phosphate; ammonium carbonate In acetonitrile at 0 - 25℃; for 6h;
Stage #2: at 90 - 95℃; for 12h;		89.5%
With thionyl chloride; SULFAMIDE In sulfolane; water
With thionyl chloride; SULFAMIDE In sulfolane; water
potassium cyanide

potassium cyanide

5-bromophthalide
64169-34-2

5-bromophthalide

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
Stage #1: potassium cyanide With acetic acid In ethylene glycol at 20℃; Sealed tube;
Stage #2: 5-bromophthalide With P(t-Bu)3 Palladacycle Gen. 3; potassium acetate In 1,4-dioxane; water at 60℃; for 16h; Sealed tube;		84%
5-bromophthalide
64169-34-2

5-bromophthalide

2-methyl-2-phenylmalononitrile
86164-70-7

2-methyl-2-phenylmalononitrile

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
With C10H8Br2N2Ni*(x)H2O; zinc In N,N-dimethyl acetamide at 80℃; for 16h; Inert atmosphere; Sealed tube;57%
4-cyanopyridine N-oxide
14906-59-3

4-cyanopyridine N-oxide

5-bromophthalide
64169-34-2

5-bromophthalide

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
With potassium fluoride; 4,4'-dimethyl-2,2'-bipyridines; trifluoroacetic acid; sodium iodide; nickel dichloride; zinc In N,N-dimethyl acetamide at 60℃; for 36h;38%
1-oxo-3-hydroxy-1,3-dihydro-N-phenylisoindole-5-carbonitrile
389613-68-7

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

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
Stage #1: 1-oxo-3-hydroxy-1,3-dihydro-N-phenylisoindole-5-carbonitrile With sodium tetrahydroborate In methanol at 20℃; for 24h;
Stage #2: With hydrogenchloride In methanol at 20℃; for 48h; pH=1;		35%
5-amino-3H-isobenzofuran-1-one
65399-05-5

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

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
With potassium cyanide; copper(II) sulfate ueber eine wss. Diazoniumsalz-Loesung;
4-cyanobenzanilide
17922-96-2

4-cyanobenzanilide

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / 0.67 h / -20 - 20 °C
1.2: 68 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C
2.1: NaBH4 / methanol / 24 h / 20 °C
2.2: 35 percent / aq. HCl / methanol / 48 h / 20 °C / pH 1
View Scheme
4-cyanobenzoyl chlorIde
6068-72-0

4-cyanobenzoyl chlorIde

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 92 percent / pyridine / CH2Cl2 / 20 h
2.1: BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / 0.67 h / -20 - 20 °C
2.2: 68 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C
3.1: NaBH4 / methanol / 24 h / 20 °C
3.2: 35 percent / aq. HCl / methanol / 48 h / 20 °C / pH 1
View Scheme
(E,Z)-1-oxo-1,3-dihydroisobenzofuran-5-carbaldehyde oxime
452978-39-1

(E,Z)-1-oxo-1,3-dihydroisobenzofuran-5-carbaldehyde oxime

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
Stage #1: (E,Z)-1-oxo-1,3-dihydroisobenzofuran-5-carbaldehyde oxime With triethylamine; trifluoroacetic acid In tetrahydrofuran at 0 - 20℃; for 1h;
Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water
4,4-dimethyl-2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)oxazoline
265137-37-9

4,4-dimethyl-2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)oxazoline

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
In thionyl chloride; water; N,N-dimethyl-formamide; toluene11.9 g (75%)
thionyl chloride
7719-09-7

thionyl chloride

1-oxo-1,3-dihydroisobenzofuran-5-carboxamide
85118-25-8

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

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide; toluene
5-bromophthalide
64169-34-2

5-bromophthalide

Cu(CN)2

Cu(CN)2

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
In water
5-bromophthalide
64169-34-2

5-bromophthalide

Zn(CN)2

Zn(CN)2

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
tetrakis(triphenylphosphine)palladium (0) In N,N-dimethyl-formamide
With NaCN; tetrakis(triphenylphosphine)palladium (0) In N,N-dimethyl-formamide
5-iodoisobenzofuran-1(3H)-one
41284-92-8

5-iodoisobenzofuran-1(3H)-one

Zn(CN)2

Zn(CN)2

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
tetrakis(triphenylphosphine)palladium (0) In N,N-dimethyl-formamide
5-chloro-3H-isobenzofuran-1-one
54109-03-4

5-chloro-3H-isobenzofuran-1-one

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
With NaCN; triphenylphosphine; nickel dichloride In tetrahydrofuran; water; acetonitrile
(1-oxo-1,3-dihydroisobenzofuran-5-yl)carbonyl chloride
227954-90-7

(1-oxo-1,3-dihydroisobenzofuran-5-yl)carbonyl chloride

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
With SULFAMIDE In sulfolane; water
3,4-bis(hydroxymethyl)benzonitrile
1446757-51-2

3,4-bis(hydroxymethyl)benzonitrile

A

6-cyanoisobenzofuran-1(3H)-one
89877-62-3

6-cyanoisobenzofuran-1(3H)-one

B

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Conditions
ConditionsYield
With Oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In water; acetonitrile at 30℃; for 8h; Green chemistry; Overall yield = 56 %;
methanol
67-56-1

methanol

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

methyl 2-(chloromethyl)-4-cyanobenzoate

methyl 2-(chloromethyl)-4-cyanobenzoate

Conditions
ConditionsYield
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile With thionyl chloride; boron trifluoride diethyl etherate; N-benzyl-N,N,N-triethylammonium chloride at 90℃; for 72h;
Stage #2: methanol With N-ethyl-N,N-diisopropylamine In ethanol; dichloromethane pH=8;		99%
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

5-cyano-2-(p-dimethylaminophenyl)indan-1,3-dione

5-cyano-2-(p-dimethylaminophenyl)indan-1,3-dione

Conditions
ConditionsYield
With sodium methylate In ethyl acetate for 0.166667h; Heating;98%
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

sodium 4-cyano-2-(hydroxymethyl)benzoate

sodium 4-cyano-2-(hydroxymethyl)benzoate

Conditions
ConditionsYield
With sodium hydroxide In water for 2h; Reflux;97%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 2h;
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

potassium 4-cyano-2-(hydroxymethyl)benzoate

potassium 4-cyano-2-(hydroxymethyl)benzoate

Conditions
ConditionsYield
With potassium hydroxide In water; isopropyl alcohol at 35 - 40℃; for 2h;97%
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

(1-oxo-1,3-dihydroisobenzofuran-5-yl)methanaminium chloride

(1-oxo-1,3-dihydroisobenzofuran-5-yl)methanaminium chloride

Conditions
ConditionsYield
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile With ammonia; hydrogen In water; isopropyl alcohol at 80℃; under 15001.5 Torr; for 24h; Autoclave;
Stage #2: With hydrogenchloride In methanol; ethyl acetate Cooling with ice;		95%
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile With ammonium hydroxide; hydrogen In water; isopropyl alcohol under 37503.8 Torr; for 4h; Autoclave; Heating;
Stage #2: With hydrogenchloride In methanol		90%
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile With borane-ammonia complex; C17H16BrMnN2O3S In hexane at 60℃; for 12h;
Stage #2: With hydrogenchloride In diethyl ether; water		50%
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon / 1,4-dioxane; water / 16 h / 80 °C
2: hydrogenchloride / water / 100 °C
View Scheme
3-(N,N-dimethylamino)propylmagnesium chloride
19070-16-7

3-(N,N-dimethylamino)propylmagnesium chloride

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

4-flourophenylmagnesium bromide
352-13-6

4-flourophenylmagnesium bromide

4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile
103146-25-4

4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile

Conditions
ConditionsYield
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile; 4-flourophenylmagnesium bromide With diethylene glycol dimethyl ether; tetrabutyl-ammonium chloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
Stage #2: 3-(N,N-dimethylamino)propylmagnesium chloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;		90%
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile; 4-flourophenylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 3.5h; Grignard reaction;
Stage #2: 3-(N,N-dimethylamino)propylmagnesium chloride In tetrahydrofuran at 0 - 20℃; Grignard reaction;		79%
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile; 4-flourophenylmagnesium bromide In tetrahydrofuran at -5℃; for 0.25h;
Stage #2: 3-(N,N-dimethylamino)propylmagnesium chloride In tetrahydrofuran at -5℃;
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile; 4-flourophenylmagnesium bromide In tetrahydrofuran at -5℃; for 0.25h;
Stage #2: 3-(N,N-dimethylamino)propylmagnesium chloride In tetrahydrofuran at -5 - 20℃; for 0.5h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran pH=2; Product distribution / selectivity;
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile; 4-flourophenylmagnesium bromide In tetrahydrofuran at 5 - 15℃; for 4h; Inert atmosphere;
Stage #2: 3-(N,N-dimethylamino)propylmagnesium chloride In tetrahydrofuran at 0 - 15℃; for 4h;		98.8 g
...Expand
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

4-cyano-2-hydroxymethylbenzoic acid
1378843-02-7

4-cyano-2-hydroxymethylbenzoic acid

Conditions
ConditionsYield
With lithium hydroxide In methanol; water for 5h; Solvent; Reagent/catalyst;87.3%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 0.25h;
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

pivaloyl chloride
3282-30-2

pivaloyl chloride

4-flourophenylmagnesium bromide
352-13-6

4-flourophenylmagnesium bromide

5-cyano-2-(4-fluorobenzoyl)benzyl pivalate

5-cyano-2-(4-fluorobenzoyl)benzyl pivalate

Conditions
ConditionsYield
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile; 4-flourophenylmagnesium bromide In tetrahydrofuran; dichloromethane at 0 - 25℃; for 18h;
Stage #2: pivaloyl chloride In tetrahydrofuran; dichloromethane at 60℃; for 2h;		87%
...Expand
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

methylmagnesium bromide
75-16-1

methylmagnesium bromide

3-(hydroxymethyl)-4-(1-hydroxy-1-methylethyl)benzonitrile
1109262-40-9

3-(hydroxymethyl)-4-(1-hydroxy-1-methylethyl)benzonitrile

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 1h;87%
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
64169-67-1

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

Conditions
ConditionsYield
In tetrahydrofuran; chloroform86.5%
In tetrahydrofuran; 1,2-dichloro-ethane85%
In tetrahydrofuran; chlorobenzene78%
In tetrahydrofuran; benzene78%
In tetrahydrofuran; toluene70%
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

4-flourophenylmagnesium bromide
352-13-6

4-flourophenylmagnesium bromide

4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
260371-16-2

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

Conditions
ConditionsYield
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile; 4-flourophenylmagnesium bromide In tetrahydrofuran; 1,2-dimethoxyethane at -10℃; for 3.5h;
Stage #2: With water; ammonium chloride In tetrahydrofuran; 1,2-dimethoxyethane at 20℃; for 0.0833333h;		86.2%
In tetrahydrofuran at 0 - 5℃; for 5h; Solvent; Temperature;85%
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile; 4-flourophenylmagnesium bromide In tetrahydrofuran; dichloromethane at -6 - -2℃;
Stage #2: With water; ammonium chloride In tetrahydrofuran; dichloromethane
In tetrahydrofuran; toluene at -4 - -2℃; Product distribution / selectivity;
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

N'-hydroxy-1-oxo-1,3-dihydroisobenzofuran-5-carboximidamide
1146973-38-7

N'-hydroxy-1-oxo-1,3-dihydroisobenzofuran-5-carboximidamide

Conditions
ConditionsYield
With hydroxylamine In ethanol; water at 20℃; for 63h; Heating / reflux;86.2%
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

magnesium
7439-95-4

magnesium

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
64169-67-1

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

Conditions
ConditionsYield
Stage #1: magnesium; 1-Bromo-4-fluorobenzene; iodine In tetrahydrofuran
Stage #2: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile In tetrahydrofuran; dichloromethane at -6 - -2℃;		86%
Stage #1: magnesium; 1-Bromo-4-fluorobenzene; iodine In tetrahydrofuran
Stage #2: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile In tetrahydrofuran; toluene at -6 - -2℃;
...Expand
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

4-flourophenylmagnesium bromide
352-13-6

4-flourophenylmagnesium bromide

4-(bis(4-fluorophenyl)hydroxymethyl)-3-(hydroxymethyl)benzonitrile
762266-07-9

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

Conditions
ConditionsYield
In toluene at 0 - 80℃; for 10h; Temperature; Solvent;84%
In tetrahydrofuran at 0 - 20℃; for 17h; Inert atmosphere;64.18%
In tetrahydrofuran at 25 - 35℃;
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

2-Methyl-1-phenyl-2-propanol
100-86-7

2-Methyl-1-phenyl-2-propanol

5-(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)isobenzofuran-1(3H)-one

5-(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)isobenzofuran-1(3H)-one

Conditions
ConditionsYield
With sulfuric acid In toluene at 0 - 20℃;82%
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

3,4-bis(hydroxymethyl)benzonitrile
1446757-51-2

3,4-bis(hydroxymethyl)benzonitrile

Conditions
ConditionsYield
With phenylsilane; potassium hydroxide In tetrahydrofuran at 66℃; for 6h;75%
With phenylsilane; potassium hydroxide In tetrahydrofuran for 4h; Schlenk technique; Inert atmosphere; Reflux;68%
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

C16H25N

C16H25N

C24H29NO2

C24H29NO2

Conditions
ConditionsYield
With tris[2-phenylpyridinato-C2,N]iridium(III); sodium acetate In N,N-dimethyl acetamide at 20℃; for 2h; Inert atmosphere; Glovebox; Irradiation; diastereoselective reaction;73%
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

1-(tert-butoxycarbonyl)-L-proline
15761-39-4

1-(tert-butoxycarbonyl)-L-proline

tert-butyl 2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)pyrrolidine-1-carboxylate
1588517-25-2

tert-butyl 2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With Ir[p-F(tert-butyl)2-phenylpyridine]3; cesium fluoride In dimethyl sulfoxide at 20℃; for 48h; Inert atmosphere; Irradiation;70%
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

N-carbobenzyloxyproline
1148-11-4

N-carbobenzyloxyproline

benzyl 2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)pyrrolidine-1-carboxylate

benzyl 2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With 1-(4-(9H-carbazol-9-yl)phenyl)-3-amino-9H-fluorene-2,4-dicarbonitrile; cesium fluoride In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation;69%
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile
260371-16-2

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

Conditions
ConditionsYield
Stage #1: 1-Bromo-4-fluorobenzene With magnesium In tetrahydrofuran Reflux; Inert atmosphere;
Stage #2: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;		63%
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

ethyl hexa-2,3-dienoate
131431-64-6, 113644-17-0

ethyl hexa-2,3-dienoate

3-ethyl-9-hydroxy-1-oxo-1,3-dihydronaphtho[2,3-c]furan-6-carbonitrile

3-ethyl-9-hydroxy-1-oxo-1,3-dihydronaphtho[2,3-c]furan-6-carbonitrile

Conditions
ConditionsYield
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.75h; Inert atmosphere;
Stage #2: ethyl hexa-2,3-dienoate In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere; regioselective reaction;		60%
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl ((1-oxo-1,3-dihydroisobenzofuran-5-yl)methyl)carbamate

tert-butyl ((1-oxo-1,3-dihydroisobenzofuran-5-yl)methyl)carbamate

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 0 - 20℃; for 12h; Inert atmosphere;56%
formic acid
64-18-6

formic acid

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

N-((1-oxo-1,3-dihydroisobenzofuran-5-yl)methyl)formamide

N-((1-oxo-1,3-dihydroisobenzofuran-5-yl)methyl)formamide

Conditions
ConditionsYield
With palladium 10% on activated carbon In 1,4-dioxane; water at 80℃; for 16h;55%
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

(E)-1-phenyl-N-(piperidin-1-yl)methanimine
1885-87-6

(E)-1-phenyl-N-(piperidin-1-yl)methanimine

A

1-[(E)-benzylideneamino]piperidine-2-carbonitrile

1-[(E)-benzylideneamino]piperidine-2-carbonitrile

B

5-[1-[(E)-benzylideneamino]-2-piperidyl]-3H-isobensofuran-1-one

5-[1-[(E)-benzylideneamino]-2-piperidyl]-3H-isobensofuran-1-one

Conditions
ConditionsYield
With tris[2-phenylpyridinato-C2,N]iridium(III); lithium acetate In dimethyl sulfoxide at 40℃; for 0.166667h; Inert atmosphere; Irradiation;A 15%
B 50%
...Expand
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

4-flourophenylmagnesium bromide
352-13-6

4-flourophenylmagnesium bromide

4-(1-(4-fluorophenyl)vinyl)-3-(hydroxymethyl)benzonitrile

4-(1-(4-fluorophenyl)vinyl)-3-(hydroxymethyl)benzonitrile

Conditions
ConditionsYield
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile; 4-flourophenylmagnesium bromide
Stage #2: Methyltriphenylphosphonium bromide With potassium tert-butylate		47%
...Expand
1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile
82104-74-3

1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile

ethyl 4-phenylbuta-2,3-dienoate
91962-64-0

ethyl 4-phenylbuta-2,3-dienoate

9-hydroxy-1-oxo-3-phenyl-1,3-dihydronaphtho[2,3-c]furan-6-carbonitrile

9-hydroxy-1-oxo-3-phenyl-1,3-dihydronaphtho[2,3-c]furan-6-carbonitrile

Conditions
ConditionsYield
Stage #1: 1-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.75h; Inert atmosphere;
Stage #2: ethyl 4-phenylbuta-2,3-dienoate In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere; regioselective reaction;		45%

5-Cyanophthalide Chemical Properties

Molecular structure of 5-Cyanophthalide (CAS NO.82104-74-3) is:

Product Name: 5-Cyanophthalide
CAS Registry Number: 82104-74-3
IUPAC Name: 1-Oxo-3H-2-benzofuran-5-carbonitrile
Molecular Weight: 159.1415 [g/mol]
Molecular Formula: C9H5NO2
XLogP3: 0.5
H-Bond Donor: 0
H-Bond Acceptor: 3 
EINECS: 279-900-2
Melting Point: 201-205 °C(lit.) 
Surface Tension: 60 dyne/cm
Density: 1.36 g/cm3
Flash Point: 199.3 °C
Enthalpy of Vaporization: 65.94 kJ/mol
Boiling Point: 407.5 °C at 760 mmHg
Vapour Pressure: 7.53E-07 mmHg at 25°C
Product Categories: Phthalides; Intermediatesofcitalopram; API intermediates; Aromatics Compounds; Aromatics; Miscellaneous Reagents

5-Cyanophthalide Uses

 5-Cyanophthalide (CAS NO.82104-74-3) is a useful synthetic intermediate.

5-Cyanophthalide Safety Profile

Safty information about 5-Cyanophthalide (CAS NO.82104-74-3) is:
Hazard Codes: HarmfulXn,Xi
Risk Statements: 20/21/22-36/37/38 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 36/37-36-26 
S36/37:Wear suitable protective clothing and gloves. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3

5-Cyanophthalide Specification

 5-Cyanophthalide , its cas register number is 82104-74-3. It also can be called 1,3-Dihydro-1-oxoisobenzofuran-5-carbonitrile .It is a white to pale yellow crystalline solid.

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