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656-42-8

Basic Information
CAS No.: 656-42-8
Name: 2,2-Difluorobenzodioxole-5-carboxaldehyde
Article Data: 6
Molecular Structure:
Molecular Structure of 656-42-8 (2,2-Difluorobenzodioxole-5-carboxaldehyde)
Formula: C8H4 F2 O3
Molecular Weight: 186.115
Synonyms: Benzaldehyde,3,4-[(difluoromethylene)dioxy]- (6CI,8CI);2,2-Difluoro-1,3-benzodioxol-5-carboxaldehyde; 2,2-Difluoro-1,3-benzodioxolo-5-carboxaldehyde;2,2-Difluoro-5-formylbenzodioxole;2,2-Difluorobenzo[1,3]dioxole-5-carboxaldehyde;2,2-Difluorobenzo[d][1,3]dioxole-5-carboxaldehyde;2,2-Difluorobenzodioxole-5-carboxaldehyde; 2,2-Difluoroindan-5-carboxaldehyde;3,4-(Difluoromethylenedioxy)benzaldehyde;5-Formyl-2,2-difluoro-1,3-benzodioxole
Density: 1.422 g/mL at 25 °C(lit.)
Boiling Point: 202-203 °C(lit.)
Flash Point: 205 °F
Solubility: Sparingly soluble in water (0.31 g/L at 25°C).
Hazard Symbols: R36/37/38:Irritating to eyes, respiratory system and skin.;
Risk Codes: R36/37/38;
Safety: 1369253
PSA: 35.53000
LogP: 1.82060
Synthetic route
1269252-03-0

2-thioxobenzo[d][1,3]dioxole-5-carbaldehyde

656-42-8

2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

Conditions
ConditionsYield
With bromine trifluoride In CFCl3; chloroform at 0℃; for 0.0166667h;95%
149045-78-3

5-dichloromethyl-2,2-difluorobenzo-(1,3)-dioxole

100-97-0

hexamethylenetetramine

656-42-8

2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

Conditions
ConditionsYield
With hydrogenchloride In water
33070-32-5

5-bromo-2,2-difluoro-2H-1,3-benzodioxole

68-12-2, 33513-42-7

N,N-dimethyl-formamide

656-42-8

2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

Conditions
ConditionsYield
Stage #1: 5-bromo-2,2-difluoro-2H-1,3-benzodioxole With n-butyllithium In tetrahydrofuran for 0.166667h; Cooling with acetone-dry ice;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 2h; Cooling with acetone-dry ice;
Stage #3: With water; ammonium chloride In tetrahydrofuran
Stage #1: 5-bromo-2,2-difluoro-2H-1,3-benzodioxole With isopropylmagnesium chloride In tetrahydrofuran at -10 - 0℃; for 5h; Inert atmosphere; Large scale;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -25℃; for 2h; Reagent/catalyst; Temperature; Inert atmosphere; Large scale;
28.6 g
139-85-5

3,4-dihydroxybenzaldehyde

656-42-8

2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium carbonate / water / 2 h / 0 °C
2: bromine trifluoride / CFCl3; chloroform / 0.02 h / 0 °C
View Scheme
1583-59-1

2,2-difluoro-1,3-benzodioxole

656-42-8

2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: iron; bromine / 20 - 30 °C / Inert atmosphere; Large scale
2.1: isopropylmagnesium chloride / tetrahydrofuran / 5 h / -10 - 0 °C / Inert atmosphere; Large scale
2.2: 2 h / -25 °C / Inert atmosphere; Large scale
View Scheme
656-42-8

2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

57260-71-6

1-t-Butoxycarbonylpiperazine

tert-butyl 4-[(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]piperazine-1-carboxylate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In tetrahydrofuran at 0 - 20℃;99%
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 16h;
656-42-8

2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

343338-28-3

(S)-2-methylpropane-2-sulfinamide

(S)-N-[(1E)-(2,2-difluoro-1,3-benzodioxol-5-yl)methylene]-2-methylpropane-2-sulfinamide

Conditions
ConditionsYield
With copper(II) sulfate In dichloromethane at 18 - 25℃; for 16h; Inert atmosphere;95%
656-42-8

2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

1576-35-8

toluene-4-sulfonic acid hydrazide

N'-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methylene)-4-methylbenzenesulfonohydrazide

Conditions
ConditionsYield
In ethanol Reflux;88%
In methanol at 20℃; for 12h; Inert atmosphere; Sealed tube;
656-42-8

2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

1779-49-3

Methyltriphenylphosphonium bromide

2,2-difluoro-5-vinylbenzo[d][1,3]dioxole

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 0.25h; Schlenk technique; Inert atmosphere;
Stage #2: 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde In tetrahydrofuran at 0 - 25℃; for 48h; Schlenk technique; Inert atmosphere;
85%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
80%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere;
76%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 0.25h; Schlenk technique; Inert atmosphere;
Stage #2: 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde In tetrahydrofuran at 0 - 20℃; Schlenk technique; Inert atmosphere;
50%
656-42-8

2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

123-82-0

2-heptylamine

C15H21F2NO2

Conditions
ConditionsYield
With triethylsilane; palladium on carbon; TPGS-750-M In water at 45℃; for 4h;85%
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    2,2-Difluorobenzodioxole-5-carboxaldehyde Chemical Properties Boiling point 202-203 °C(lit.) density 1.422 g/mL at 25 °C(lit.) refractive index n20/D 1.5000(lit.) Fp 205 °F storage temp. Keep in dark place,Sealed in dr

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Chemistry

Molecular Structure of 2,2-Difluorobenzodioxole-5-carboxaldehyde (CAS No.656-42-8):
 
Molecular Formula: C8H4F2O3
Molecular Weight: 186.1124
CAS No: 656-42-8
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 1
Polar Surface Area: 35.53 Å2
Index of Refraction: 1.525
Molar Refractivity: 38.02 cm3
Molar Volume: 124 cm3
Surface Tension: 41.5 dyne/cm
Density: 1.5 g/cm3
Flash Point: 79.1 °C
Enthalpy of Vaporization: 44.68 kJ/mol
Boiling Point: 210.5 °C at 760 mmHg
Vapour Pressure: 0.191 mmHg at 25°C
IUPAC Name: 2,2-Difluoro-1,3-benzodioxole-5-carbaldehyde
InChI: InChI=1/C8H4F2O3/c9-8(10)12-6-2-1-5(4-11)3-7(6)13-8/h1-4H
InChIKey: GGERGLKEDUUSAP-UHFFFAOYAB
Std. InChI: InChI=1S/C8H4F2O3/c9-8(10)12-6-2-1-5(4-11)3-7(6)13-8/h1-4H
Std. InChIKey: GGERGLKEDUUSAP-UHFFFAOYSA-N
Product Categories: Heterocycles series;Aldehydes;Benzodiozoles, Benzodioxines Benzodioxepines;Benzodiozoles, Benzodioxines Benzodioxepines

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 3
Hazard Note: Irritant

Specification

   2,2-Difluorobenzodioxole-5-carboxaldehyde (CAS No.656-42-8), its synonyms are 2,2-Difluoro-5-formyl-1,3-benzodioxole ; 2,2-Difluoro-1,3-benzodioxole-5-carboxaldehyde ; 2,2-Difluoro-5-formylbenzodioxole .