| Identification | More | [Name]
3,4-Dimethoxyacetophenone | [CAS]
1131-62-0 | [Synonyms]
1-(3,4-DIMETHOXYPHENYL)ETHAN-1-ONE
1-(3,4-DIMETHOXYPHENYL)-ETHANO
1-(3,4-DIMETHOXYPHENYL)-ETHANONE
3',4'-DIMETHOXYACETOPHENONE
3,4-DIMETHOXYACETOPHENONE
4-ACETYLPYROCATECHOL DIMETHYL ETHER
4-ACETYLVERATROLE
ACETOVERATRON
ACETOVERATRONE
AKOS 220-35
AKOS BBS-00003221
LABOTEST-BB LT00000195
1-(3,4-dimethoxyphenyl)-ethanon
3,4-Dimethoxyacetophenon
3,4-Dimethoxyphenyl methyl ketone
3,4-Dimethoxyphenylmethylketone
Acetophenone, 3',4'-dimethoxy-
Acetophenone,3’,4’-dimethoxy-
Ethanone,1-(3,4-dimethoxyphenyl)-
Methyl3,4-dimethoxyphenylketone | [EINECS(EC#)]
214-468-0 | [Molecular Formula]
C10H12O3 | [MDL Number]
MFCD00008737 | [Molecular Weight]
180.2 | [MOL File]
1131-62-0.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow to beige crystalline powder | [Melting point ]
47-54 °C(lit.)
| [Boiling point ]
286-288 °C(lit.)
| [density ]
1.1272 (rough estimate) | [refractive index ]
1.5224 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
hot water: soluble | [form ]
Crystalline Powder | [color ]
Yellow to beige | [Odor]
at 10.00 % in dipropylene glycol. sweet woody floral | [Odor Type]
woody | [Water Solubility ]
SOLUBLE IN HOT WATER | [BRN ]
781213 | [InChI]
1S/C10H12O3/c1-7(11)8-4-5-9(12-2)10(6-8)13-3/h4-6H,1-3H3 | [InChIKey]
IQZLUWLMQNGTIW-UHFFFAOYSA-N | [SMILES]
COc1ccc(cc1OC)C(C)=O | [LogP]
1.822 (est) | [CAS DataBase Reference]
1131-62-0(CAS DataBase Reference) | [NIST Chemistry Reference]
Ethanone, 1-(3,4-dimethoxyphenyl)-(1131-62-0) | [EPA Substance Registry System]
1131-62-0(EPA Substance) |
| Questions And Answer | Back Directory | [Synthesis]
To a stirred mixture of 3´,4´-dihydroxyacetophenone (100 mg, 0.66 mmol) and anhydrous K2CO3 (5 g, 36 mmol) in dry acetone (10 mL) was added MeI (1 mL, 16 mmol). The mixture was heated at reflflux for 45 min, cooled to room temperature, fifiltered, and evaporated under reduced pressure. The residue was dissolved in CH2Cl2, washed with 2 portions of water, dried over anhydrous Na2SO4, and evaporated under reduced pressure. The product was purifified by flflash chromatography (silica, hexane/EtOAc 4:1, v/v). Removal of the solvent gave a 93% yield of the product, 3´,4´-dimethoxyacetophenone (110 mg, 0.61 mmol). Reference: Khatib, S.; Nerya, O.; Musa, R.; Shmuel, M.; Tamir, S.; Vaya, J. Bioorg. Med. Chem. 2005, 13, 433−441.
|
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P280-P271 | [Hazard Codes ]
Xi | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [TSCA ]
Yes | [HS Code ]
29145000 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
yellow to beige crystalline powder | [Uses]
3',4'-Dimethoxyacetophenone is used as Catalytic agent; Petrochemical additive. It is also used in agrochemical, pharmaceutical and dyestuff field. | [Definition]
ChEBI: A member of the class of acetophenones that is acetophenone substituted by methoxy groups at positions 3' and 4' respectively. | [Preparation]
Obtained by reaction of dimethyl sulfate with acetoguaiacone in the presence of sodium hydroxide in ethanol, first at 50°, then at reflux for 1 h (78%). | [Synthesis Reference(s)]
Tetrahedron Letters, 36, p. 409, 1995 DOI: 10.1016/0040-4039(94)02221-V | [References]
[1] G. Hawkes. “An unusual anodic methoxylation: 3,4-dimethoxyacetophenone.” Tetrahedron Letters 33 1 (1992): 8133–8136.
[2] P. Kuzmi?, M. Soucek. “Substituent effects in aromatic photochemistry. UV irradiation of 3,4-dimethoxybenzonitrile and 3,4-dimethoxyacetophenone in the presence of inorganic anions.” Collection of Czechoslovak Chemical Communications 52 1 (1987): 980–988.
[3] Virginia Vetere . “Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalysts.” Catalysis Today 107 (2005): Pages 266-272. |
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