| Identification | More | [Name]
2,5-Dimethoxybenzaldehyde | [CAS]
93-02-7 | [Synonyms]
2,5-DIMETHOXYBENZALDEHYDE
AKOS BBS-00003162
2,5-dimethoxy-benzaldehyd
Benzaldehyde, 2,5-dimethoxy-
2,5-Dimethoxybenzaldehyde, 98+% | [EINECS(EC#)]
202-211-5 | [Molecular Formula]
C9H10O3 | [MDL Number]
MFCD00003314 | [Molecular Weight]
166.17 | [MOL File]
93-02-7.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow crystalline solid | [Melting point ]
46-48 °C (lit.) | [Boiling point ]
146 °C/10 mmHg (lit.) | [density ]
1.1708 (rough estimate) | [refractive index ]
1.5260 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
795mg/l | [form ]
Crystalline Powder, Crystals and/or Chunks | [color ]
Yellow to beige | [Water Solubility ]
Soluble in chloroform and methanol. Slightly soluble in water. | [Sensitive ]
Air Sensitive | [BRN ]
509301 | [InChIKey]
AFUKNJHPZAVHGQ-UHFFFAOYSA-N | [LogP]
1.910 | [CAS DataBase Reference]
93-02-7(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzaldehyde, 2,5-dimethoxy-(93-02-7) | [EPA Substance Registry System]
93-02-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing . | [WGK Germany ]
2
| [RTECS ]
CU5740500
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29124900 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
trans-Anethole-->p-Anisaldehyde-->4-Methoxyphenol-->Dimethyl sulfate-->2-Hydroxy-5-methoxybenzaldehyde | [Preparation Products]
2,5-Dimethoxybenzylamine-->1-(2 5-DIMETHOXYPHENYL)-2-AMINOPROPANE&-->4-IODO-2,5-DIMETHOXYPHENETHYLAMINE-->2,5-DIMETHOXYBENZYL ALCOHOL-->2-Amino-1-(2,5-dimethoxyphenyl)ethanol-->4 7-DIMETHOXY-1-INDANONE 97-->4-Bromo-2,5-dimethoxybenzaldehyde-->2,5-Dimethoxycinnamic acid-->2-(2,5-Dimethoxy-phenyl)-benzothiazole-->3-[(5Z)-5-[(2,5-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid-->2,5-Dimethoxy-Beta-Nitrostyrene |
| Hazard Information | Back Directory | [Chemical Properties]
yellow crystalline solid
| [Uses]
2,5-Dimethoxybenzaldehyde is used in the preparation of 2,5-dimethoxyphenethylamine, which is utilized to prepare psychoactive drugs such as 2,5-dimethoxy-4-bromophenethylamine, 2,5-dimethoxy-4-iodophenethylamine and 4-Chloro-2,5-dimethoxy-phenethylamine. It acts as an intermediate in organic synthesis. | [Application]
2,5-Dimethoxybenzaldehyde, also known as 2C-H, is an organic compound and a benzaldehyde derivative. It can be used to produce 2,5-dimethoxyphenethylamine. 2C-H is also used to produce many other substituted phenethylamines such as 2C-B, 2C-I and 2C-C. | [Definition]
ChEBI: 2,5-dimethoxy-Benzaldehyde is a dimethoxybenzene. | [Preparation]
2,5-Dimethoxybenzaldehyde synthesis: Anethole is oxidized to anisaldehyde , which after isolation is subjected to a BaeyerVilliger oxidation reaction with performic or peracetic acid. The O-formyl-4-methoxyphenol obtained this way is hydrolyzed . 4-Methoxyphenol is subsequently formylated using the Reimer-Tiemann method and the obtained 2-hydroxy-5-methoxybenzaldehyde is methylated with dimethylsulfate to 2,5-dimethoxybenzaldehyde.
Reaction
A : Anisaldehyde from anethole via oxidative cleavage: 20 g anise oil was suspended in a mixture of 150 mL water and 30 mL conc. sulfuric acid; addition of 55 g sodium bichromate at such a rate that the temperature did not exceed 40°C. The reaction mixture was extracted with 4 x 125 mL toluene and the solvent evaporated. The residual oil was vacuum distilled to yield 9.1 g anisaldehyde.
B : O-formyl-4-methoxyphenol: 6 mL anisaldehyde was dissolved in 75 mL dichloromethane (DCM). A mixture of 12 g hydrogen peroxide and 10 mL conc. formic acid was added over 30 min. The reaction mixture was gently refluxed for 21 h.
C: B 4-methoxyphenol: Evaporating the solvent from reaction mixture and taking up the residue in 100 mL aqueous NaOH (20%) (25 mL MeOH as co-solvent) yielded 4.1 g 4-methoxyphenol as a white crystalline product after the usual work-up and purification steps.
D : Reimer-Tiemann formylation of 4-methoxyphenol: 124.1 g 4-methoxyphenol was dissolved in NaOH solution (320 g NaOH in 400 mL water). In total, 161 mL chloroform was added. The usual work-up and steam distillation yielded 109.8 g of a clear yellow oil that did not solidify upon standing at room temperature (GC/MS: 94% 2-hydroxy-5-methoxybenzaldehyde).
E: D Methylation of 2-hydroxy-5-methoxybenzaldehyde: The yellow oil from was used without further purification. A 250 mL RB flask was charged with 100 mL acetone, 14 g anhydrous potassium carbonate and 10 g 2-hydroxy-5-methoxybenzaldehyde; the mixture was brought at reflux temperature and 11 g dimethyl sulfate was added. The reaction was continued for 4 hours. The solvent is evaporated and the crude end product crystallized in cold water. Recrystallization from EtOH/water yielded 8.3 g 2,5-dimethoxybenzaldehyde (GC/MS: 98%+ 2,5-dimethoxybenzaldehyde) |
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