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1,3-Benzodioxole

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Name

1,3-Benzodioxole

EINECS 205-992-0
CAS No. 274-09-9 Density 1.213 g/cm3
PSA 18.46000 LogP 1.41530
Solubility 0.2 g/100 mL (25 °C) in water Melting Point -18 °C
Formula C7H6O2 Boiling Point 173 °C at 760 mmHg
Molecular Weight 122.123 Flash Point 55 °C
Transport Information UN 1993 3/PG 3 Appearance clear colourless to light yellow liquid
Safety 23-24/25-36/37/39-26-16-36 Risk Codes 20/22-22-10-36/37/38-20/21/22
Molecular Structure Molecular Structure of 274-09-9 (1,3-Benzodioxole) Hazard Symbols HarmfulXn, IrritantXi
Synonyms

Benzene,1,2-(methylenedioxy)- (6CI,8CI);(Methylenedioxy)benzene;1,2-(Methylenedioxy)benzene;1,3-Dioxaindan;1,3-Dioxindan;2H-1,3-Benzodioxole;2H-Benzo[d]-1,3-dioxolane;Benzene,1,2-[methylenebis(oxy)]-;Benzodioxole;o-(Methylenedioxy)benzene;Methylene Dioxy Benzene;1,2-Methylenedioxybenzene;

Article Data 87

1,3-Benzodioxole Synthetic route

7228-38-8

5-chloro-1,3-benzodioxole

274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 5h;100%
Stage #1: 5-chloro-1,3-benzodioxole With ethidium Bromide; magnesium; iron(II) chloride; magnesium chloride In tetrahydrofuran at 22 - 52℃; for 23h;
Stage #2: With water In tetrahydrofuran
In isopropyl alcohol for 15h; Irradiation; Inert atmosphere;100 %Chromat.
94839-07-3

3,4-(methylenedioxy)-benzeneboronic acid

274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; tetrahydroxydiboron; 1,3-bis(bis(4-methoxyphenyl)phosphino)propane In water; 1,2-dichloro-ethane at 70℃; for 0.25h;99%
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); water In toluene at 90℃; for 1h; Microwave irradiation; Green chemistry;62%
Stage #1: 3,4-(methylenedioxy)-benzeneboronic acid With (HOCH2)2CMeCH2O-polymer In tetrahydrofuran Cyclization;
Stage #2: With Ag(NH3)NO3 In tetrahydrofuran for 8h; Protodeboronation; Heating; Further stages.;
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide; cyclohexanol at 110℃; for 12h;96%
With tris(dibenzylideneacetone)dipalladium (0); tris(2,4-di-tert-butylphenyl)phosphite; caesium carbonate In cyclohexanol at 120℃; for 10h;85 %Chromat.
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium tert-butylate; isopropyl alcohol at 100℃; Schlenk technique; Inert atmosphere;88%Chromat.
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; carbon dioxide; palladium diacetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 12h; Reagent/catalyst; Solvent; Irradiation;100 %Spectr.
With triethylamine In acetonitrile at 20℃; for 15h; Irradiation; Inert atmosphere;94 %Spectr.
75-09-2

dichloromethane

120-80-9

benzene-1,2-diol

274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide at 50 - 100℃; for 5.5h; Reagent/catalyst; Temperature; Microwave irradiation;95%
In 1-methyl-pyrrolidin-2-one Reagent/catalyst;94.69%
With sodium hydroxide In dimethyl sulfoxide at 90 - 120℃; for 0.5h; Temperature; Solvent; Reagent/catalyst;85.4%
74-97-5

chlorobromomethane

120-80-9

benzene-1,2-diol

A

274-09-9

Methylenedioxybenzene

B

263-29-6

dibenzo-tetroxecin

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20 - 110℃;A 88%
B 11%
75-11-6

diiodomethane

120-80-9

benzene-1,2-diol

274-09-9

Methylenedioxybenzene

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 110℃; for 1h; Inert atmosphere;80%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 80℃; for 12h;62.1%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 80℃; for 12h;62.1%
With potassium hydroxide; hydrogen
With sodium hydride 1.) HMPT, room temp.; 2.) room temp., 20 min; Yield given. Multistep reaction;
124-38-9

carbon dioxide

5876-51-7

5-iodo-1,3-benzodioxole

A

274-09-9

Methylenedioxybenzene

B

94-53-1

Piperonylic acid

Conditions
ConditionsYield
With tetraethylammonium tosylate; triphenylphosphine; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide Pt anode/Pt cathode; electrolysis with 2.5 mA/cm2;A 13%
B 76%
7228-38-8

5-chloro-1,3-benzodioxole

95-93-2

1,2,4,5-tetramethylbenzene

A

274-09-9

Methylenedioxybenzene

B

954367-93-2

3,4-methylenedioxy-2',3',5',6'-tetramethyl-biphenyl

Conditions
ConditionsYield
With triethylamine In 2,2,2-trifluoroethanol for 7h; Photolysis;A n/a
B 76%
930-68-7

cyclohexenone

994-30-9

triethylsilyl chloride

5876-51-7

5-iodo-1,3-benzodioxole

A

274-09-9

Methylenedioxybenzene

B

1416985-76-6

((3-(benzo[d][1,3]dioxol-5-yl)cyclohex-1-en-1-yl)oxy)triethylsilane

Conditions
ConditionsYield
With bis(acetylacetonate)nickel(II); manganese; 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl acetamide at 20℃; for 1h;A 5 mg
B 76%
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

677-22-5

tert-butylmagnesium chloride

A

274-09-9

Methylenedioxybenzene

B

7228-36-6

5-(tert-butyl)benzo[d][1,3]dioxole

Conditions
ConditionsYield
With 1.54H2O*Cl2Ni; 1,3-bis(cyclohexyl)imidazolium tetrafluoroborate In tetrahydrofuran at -10℃; for 1.5h; Kumada coupling reaction; Inert atmosphere;A 17 mg
B 73%

1,3-Benzodioxole Chemical Properties


IUPAC Name: 1,3-Benzodioxole
Canonical SMILES: C1OC2=CC=CC=C2O1
InChI: InChI=1S/C7H6O2/c1-2-4-7-6(3-1)8-5-9-7/h1-4H,5H2
InChIKey: FTNJQNQLEGKTGD-UHFFFAOYSA-N
Molecular Weight: 122.12134 [g/mol]
Molecular Formula: C7H6O2
XLogP3: 2.1
H-Bond Donor: 0
H-Bond Acceptor: 2 
EINECS: 205-992-0 
Melting Point: -18 °C 
Index of Refraction: 1.557
Molar Refractivity: 32.41 cm3
Molar Volume: 100.6 cm3
Surface Tension: 46.4 dyne/cm
Density: 1.213 g/cm3
Flash Point: 55 °C
Enthalpy of Vaporization: 39.25 kJ/mol
Boiling Point: 173 °C at 760 mmHg
Vapour Pressure: 1.73 mmHg at 25 °C
Water Solubility: 0.2 g/100 mL (25 °C)
Product Categories: Aromatic Ethers
Appearance of 1,2-Methylenedioxybenzene (CAS NO.274-09-9): clear colourless to light yellow liquid

1,3-Benzodioxole Uses

 1,2-Methylenedioxybenzene (CAS NO.274-09-9), in chemistry, especially organic chemistry, is an aromatic ring.

1,3-Benzodioxole Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 1220mg/kg (1220mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: COMA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
rat LD50 oral 580mg/kg (580mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT
Toxicology and Applied Pharmacology. Vol. 7, Pg. 18, 1965.

1,3-Benzodioxole Consensus Reports

Reported in EPA TSCA Inventory.

1,3-Benzodioxole Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:  Xn,IrritantXi
Hazard Note: Irritant
Risk Statements:
10:  Flammable 
22:  Harmful if swallowed 
20/21/22:  Harmful by inhalation, in contact with skin and if swallowed 
20/22:  Harmful by inhalation and if swallowed 
36/37/38:  Irritating to eyes, respiratory system and skin 
Safety Statements:
16:  Keep away from sources of ignition - No smoking 
23:  Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) 
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing 
24/25:  Avoid contact with skin and eyes 
36/37/39:  Wear suitable protective clothing, gloves and eye/face protection 
RIDADR: UN 1993 3/PG 3
WGK Germany: 3
RTECS of 1,2-Methylenedioxybenzene (CAS NO.274-09-9): DA5600000

1,3-Benzodioxole Specification

  1,2-Methylenedioxybenzene (CAS NO.274-09-9), its Synonyms are 1,3-Dioxaindan ; 1,3-Dioxindan ; 2H-1,3-Benzodioxole ; 3,4-Methylenedioxybenzene ; Benzene, 1,2-(methylenebis(oxy))- ; Benzodioxole ; Methylenedioxybenzene ; o-(Methylenedioxy)benzene ; 1,3-Benzodioxolane ; 1,3-Benzodioxole ; Benzene, 1,2-methylenedioxy- .

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