2,2-Difluorobenzodioxole-5-carboxaldehyde supplier

Name
2,2-Difluorobenzodioxole-5-carboxaldehyde
EINECS
CAS No. 656-42-8
Article Data6
CAS DataBase
Density 1.422 g/mL at 25 °C(lit.)
Solubility Sparingly soluble in water (0.31 g/L at 25°C).
Melting Point
Formula C8H4 F2 O3
Boiling Point 202-203 °C(lit.)
Molecular Weight 186.115
Flash Point 205 °F
Transport Information
Appearance
Safety 1369253
Risk Codes R36/37/38;
Molecular Structure
Hazard Symbols R36/37/38:Irritating to eyes, respiratory system and skin.;
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
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With triethylsilane; palladium on carbon; TPGS-750-M In water at 45℃; for 4h;	85%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 75-16-1
methylmagnesium bromide

: 1009032-10-3
1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)ethan-1-ol

Conditions

Conditions	Yield
Stage #1: 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde; methylmagnesium bromide In diethyl ether at 0 - 20℃; for 0.25 - 0.333333h; Stage #2: With water at 0℃;	83.5%

: 110-85-0
piperazine

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 1093211-85-8
1-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)piperazine

Conditions

Conditions	Yield
With hydrogen; 20% palladium hydroxide-activated charcoal In methanol; toluene at 20 - 70℃; under 760.051 Torr; for 36h;	83%
Stage #1: piperazine; 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde In methanol at 20℃; for 18h; Stage #2: With 20% palladium hydroxide on charcoal; hydrogen In methanol at 70℃; under 760.051 Torr;	83%
Stage #1: piperazine; 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde In methanol at 20℃; for 18h; Inert atmosphere; Stage #2: With 10 wt% Pd(OH)2 on carbon; hydrogen In methanol at 70℃; under 760.051 Torr;	83%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 108-91-8
cyclohexylamine

: 1443830-94-1
N-[(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]cyclohexanamine

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane at 25℃; Molecular sieve;	82%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 662157-81-5
2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid hydrazide

: 2',4'-difluoro-4-hydroxy-N'-[(2,2-difluoro-1,3-benzodioxol-5-yl)methylidene] biphenyl-3-carbohydrazide

Conditions

Conditions	Yield
In ethanol for 2h; Reflux;	82%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: (1S,3S,4R)-4-[(3aS,4R,5S,7aS)-4-(aminomethyl)-7a-methyl-1-methylidene-octahydro-1H-inden-5-yl]-3-(hydroxymethyl)-4-methylcyclohexan-1-ol

: (1S,3S,4R)-4-((3aS,4R,5S,7aS)-4-(((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methylamino)methyl)-7a-methyl-1-methyleneoctahydro-1H-inden-5-yl)-3-(hydroxymethyl)-4-methylcyclohexanol

Conditions

Conditions	Yield
Stage #1: 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde; (1S,3S,4R)-4-[(3aS,4R,5S,7aS)-4-(aminomethyl)-7a-methyl-1-methylidene-octahydro-1H-inden-5-yl]-3-(hydroxymethyl)-4-methylcyclohexan-1-ol In methanol for 0.5h; Reflux; Inert atmosphere; Stage #2: With methanol; sodium tetrahydroborate at 20℃; Inert atmosphere;	81%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: N-methyl-N-tosylpropiolamide

: (±)-(4R,5R)-5-(2,2-difluorobenzo[d][1,3]dioxole-5-carbonyl)-2-methyl-4-(p-tolyl)isothiazolidin-3-one 1,1-dioxide

Conditions

Conditions	Yield
With eosin Y disodium salt In acetonitrile at 80℃; for 48h; Smiles Aromatic Rearrangement; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation; diastereoselective reaction;	80%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 72768-97-9
(2,2-difluoro-1,3-benzodioxol-5-yl)methanol

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20 - 30℃; for 3.5h; Reagent/catalyst; Inert atmosphere; Large scale;	77.7%
With methanol; sodium tetrahydroborate

: 4971-56-6
tetrahydrofuran-2,4-dione

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 54258-41-2
1,10-phenanthroline-5-amine

: (9aR,13S)-13-((3,4-difluoromethylenedioxy)phenyl)-9a-hydroxy-9a,10,12a,13-tetrahydrofuro[3,4-b]pyrido[3,2-f][1,10]phenanthrolin-12(9H)-one

Conditions

Conditions	Yield
In ethanol Reflux;	77%

...Expand

: 673-32-5
1-Phenylprop-1-yne

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-4-phenylbut-3-yn-1-ol

Conditions

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine; (1,2,3,4,5-pentamethylcyclopentadienyl)(tetrahydrofuran)dicarbonyliron(II) tetrafluoroborate; boron trifluoride diethyl etherate In toluene at 100℃; for 24h;	76%

: 541-57-1
4-hydroxy-2(5H)-furanone

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 867069-17-8
9-(2,2-difluoro-1,3-benzodioxol-5-yl)-6,9-dihydro[1,3]dioxolo[4,5-g]furo[3,4-b]quinolin-8(5H)-one

Conditions

Conditions	Yield
Inert atmosphere; Reflux;	75%

...Expand

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 7677-24-9
trimethylsilyl cyanide

: 2-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2-(trimethylsilyloxy)acetonitrile

Conditions

Conditions	Yield
Stage #1: 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde With zinc(II) iodide In dichloromethane at 10 - 15℃; Stage #2: trimethylsilyl cyanide In dichloromethane at 20℃; for 1h;	75%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 27318-90-7
1,10-phenanthroline-5,6-dione

: 1187485-75-1
2-(3',3'-difluoro-3,4-methylenedioxyphenyl)imidazo[4,5-f][1,10]phenanthroline

Conditions

Conditions	Yield
With ammonium acetate; acetic acid for 2h; Reflux;	74%
With ammonium acetate; acetic acid for 2h; Reflux;	74%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 1254928-30-7
[1-(6-ethyl-4,4-dimethyI-1,2,3,4-tetrahydro-quinolin-7-yl)-ethyl]-carbamic acid tert-butyl ester

: 1254928-67-0
{1-[1-(2,2-difluoro-benzo[1,3]dioxol-5-ylmethyl)-6-ethyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl]-ethyl}-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With sodium cyanoborohydride In tetrahydrofuran at 65℃; for 20h; sealed tube;	74%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 294619-51-5
3,4-(difluoromethylenedioxy)-6-nitrobenzaldehyde

Conditions

Conditions	Yield
With nitric acid; trifluoroacetic acid In dichloromethane at -60 - 4℃; Nitration;	73%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 1219810-39-5
(2,2-difluorobenzo-1,3-dioxol-5-yl)methyl 2,2-difluorobenzo-1,3-dioxole-5-carboxylate

Conditions

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; sodium formate; cyclohexyldiphenylphosphine In 1,4-dioxane at 80℃; for 20h; Tishchenko reaction; Inert atmosphere;	73%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 146322-07-8
1-(2,2-difluorobenzo[1,3]dioxan-5-yl)ethanone oxime

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In methanol at 20℃; for 6h;	72%

: 123-75-1
pyrrolidine

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: C21H17F2NO5

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 2h;	71%

...Expand

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 768-56-9
4-Phenyl-1-butene

: 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2-methyl-4-phenylbutan-1-ol

Conditions

Conditions	Yield
With chromium chloride; (±)N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II); phenylsilane; 1-fluoro-2,4,6-trimethylpyridin-1-ium tetrafluoroborate In tetrahydrofuran; acetonitrile at 22℃; for 24h; Inert atmosphere; chemoselective reaction;	71%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 141-82-2
malonic acid

: 721-13-1
3-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-acrylic acid

Conditions

Conditions	Yield
With piperidine; pyridine for 3h; Heating / reflux;	70%
With piperidine In pyridine for 3h; Heating / reflux;	70%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 141-82-2
malonic acid

: 387350-55-2
3-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-acrylic acid

Conditions

Conditions	Yield
With pyridine; piperidine for 3h; Knoevenagel Condensation; Heating / reflux;	70%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 557-93-7
2-bromoprop-1-ene

: 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)butan-1-one

Conditions

Conditions	Yield
With acetylacetonatodicarbonylrhodium(l); potassium formate; potassium carbonate; triphenylphosphine In 1,2-dimethoxyethane at 130℃; for 16h; Inert atmosphere; Sealed tube;	66%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 1826-67-1
vinyl magnesium bromide

: 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	64%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 53947-84-5
2-[(2-carboxyacetyl)amino]benzoic acid

: (E)-2-[[3-(2,2-difluoro-1,3-benzodioxol-5-yl)-1-oxo-2-propenyl]amino]benzoic acid

Conditions

Conditions	Yield
With piperidine In toluene for 0.5h; Knoevenagel Condensation; Dean-Stark; Reflux;	62%

: 656-42-8
2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

: 1895-39-2
sodium chlorodifluoroacetate

: 5-(2,2-difluorovinyl)-2,2-difluorobenzo[d][1,3]dioxole

Conditions

Conditions	Yield
With triphenylphosphine In N,N-dimethyl-formamide at 100℃; Inert atmosphere;	62%

2,2-Difluorobenzodioxole-5-carboxaldehyde Chemical Properties

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

2,2-Difluorobenzodioxole-5-carboxaldehyde Safety Profile

Hazard Codes: Irritant Xi
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

2,2-Difluorobenzodioxole-5-carboxaldehyde 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 .

Product Name

2,2-Difluorobenzodioxole-5-carboxaldehyde

Synthetic route

2,2-Difluorobenzodioxole-5-carboxaldehyde Chemical Properties

2,2-Difluorobenzodioxole-5-carboxaldehyde Safety Profile

2,2-Difluorobenzodioxole-5-carboxaldehyde Specification

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