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82104-74-3

Basic Information
CAS No.: 82104-74-3
Name: 5-Cyanophthalide
Article Data: 15
Molecular Structure:
Molecular Structure of 82104-74-3 (5-Cyanophthalide)
Formula: C9H5NO2
Molecular Weight: 159.144
Synonyms: 1,3-Dihydro-1-oxoisobenzofuran-5-carbonitrile;
EINECS: 279-900-2
Density: 1.36 g/cm3
Melting Point: 201-205 °C(lit.)
Boiling Point: 407.5 °C at 760 mmHg
Flash Point: 199.3 °C
Appearance: white to pale yellow crystalline solid
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 20/21/22-36/37/38
Safety: 36/37-36-26
PSA: 50.09000
LogP: 1.22868
Synthetic route
934473-85-5

5-hydroxamyl phthalide

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%
4792-29-4

5-carboxyphtalide

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

64169-34-2

5-bromophthalide

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%
64169-34-2

5-bromophthalide

86164-70-7

2-methyl-2-phenylmalononitrile

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%
14906-59-3

4-cyanopyridine N-oxide

64169-34-2

5-bromophthalide

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%
389613-68-7

1-oxo-3-hydroxy-1,3-dihydro-N-phenylisoindole-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%
65399-05-5

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

82104-74-3

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

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

4-cyanobenzanilide

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
6068-72-0

4-cyanobenzoyl chlorIde

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
452978-39-1

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

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
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    CAS NO.:82104-74-3

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    82104-74-3

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Chemistry

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

Uses

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

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

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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