| Identification | More | [Name]
4-N-BUTOXYBENZALDEHYDE | [CAS]
5736-88-9 | [Synonyms]
4-BUTOXYBENZALDEHYDE
4-N-BUTOXYBENZALDEHYDE
4-N-BUTYLOXYBENZALDEHYDE
AKOS B000285
OTAVA-BB BB7020401737
P-BUTOXYBENZALDEHYDE
P-N-BUTOXYBENZALDEHYDE
TIMTEC-BB SBB008007
4-butoxy-benzaldehyd
Benzaldehyde, p-butoxy-
BUTOXYBENZALDEHYDE
Methyl 3-formyl-1H-indole-4-carboxylate
1-ethyl-1h-pyrazole-5-carbaldehyde
1,5-dimethyl-4-(trifluoromethyl)-1h-pyrazole-3-carbaldehyde
1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazole-4-carbaldehyde
4-pyrrolidin-1-ylpyridine-2-carbaldehyde
1-(1-benzylpiperidin-4-yl)-1h-pyrrole-2-carbaldehyde
6-bromoimidazo[1,2-a]pyridine-3-carbaldehyde
5-(4-methylpiperazin-1-yl)-2-furaldehyde
5-(1h-imidazol-1-yl)-2-furaldehyde | [EINECS(EC#)]
227-247-9 | [Molecular Formula]
C11H14O2 | [MDL Number]
MFCD00003389 | [Molecular Weight]
178.23 | [MOL File]
5736-88-9.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR YELLOW TO ORANG-RED LIQUID | [Melting point ]
184 °C | [Boiling point ]
285 °C (lit.) | [density ]
1.031 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.539(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
Liquid | [color ]
Clear yellow to orang-red | [Specific Gravity]
1.031 | [InChI]
InChI=1S/C11H14O2/c1-2-3-8-13-11-6-4-10(9-12)5-7-11/h4-7,9H,2-3,8H2,1H3 | [InChIKey]
XHWMNHADTZZHGI-UHFFFAOYSA-N | [SMILES]
C1C=C(OCCCC)C=CC=1C=O | [CAS DataBase Reference]
5736-88-9(CAS DataBase Reference) | [EPA Substance Registry System]
Benzaldehyde, 4-butoxy- (5736-88-9) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29124990 |
| Hazard Information | Back Directory | [Chemical Properties]
CLEAR YELLOW TO ORANG-RED LIQUID | [Uses]
4-Butoxybenzaldehyde has been used in the synthesis of:
- 6-amino-4-(4-butoxyphenyl)-3,5-dicyanopyridine-2(1H)-thione
- 16-(p-butoxybenzylidene)androsta-1,4-diene-3,17-dione via condensation reaction with androsta-1,4-diene-3,17-dione
| [Synthesis Reference(s)]
The Journal of Organic Chemistry, 66, p. 2966, 2001 DOI: 10.1021/jo0056848 | [General Description]
Kinetic constant for the inhibition of the diphenolase activity of mushroom tyrosinase by 4-butoxybenzaldehyde has been evaluated. | [Synthesis]
In a 100 mL round-bottomed flask equipped with a reflux condenser tube and a magnetic stirrer, p-hydroxybenzaldehyde (35 g, 287 mmol) and 1-bromobutane (30.92 mL, 287 mmol) were dissolved in N,N-dimethylformamide (DMF, 750 mL). The reaction mixture was stirred for 20 min under nitrogen protection. Subsequently, anhydrous potassium carbonate (118.83 g, 860 mmol) was added and the reaction was continued to be stirred at 70 °C for 20 hours. After completion of the reaction, the mixture was cooled to room temperature. The reaction was quenched with excess water and extracted with ethyl acetate. The organic phases were combined, washed several times with water, dried over anhydrous sodium sulfate and filtered. The crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 20:1) to afford the brown oily target product 4-butoxybenzaldehyde. Yield: 95%; 1H NMR (500 MHz, CDCl3) δH (ppm): 9.89 (s, 1H), 7.84 (d, J = 8.8 Hz, 2H), 7.00 (d, J = 8.6 Hz, 2H), 4.06 (t, J = 6.3 Hz, 2H), 1.79-1.85 (m, 2H), 1.49-1.57 (m. 2H), 1.01 (t, J = 7.3 Hz, 3H); 13C NMR (125 MHz, CDCl3) δC (ppm): 190.7, 164.2, 131.9, 129.8, 114.7, 68.1, 31.0, 19.1, 13.7; ESI-MS: m/z 179.2 ([M + H]+). The following alkoxybenzaldehyde derivatives 4b-h were synthesized by a similar method. | [References]
[1] Journal of the American Chemical Society, 2014, vol. 136, # 46, p. 16399 - 16410
[2] Journal of the American Chemical Society, 2010, vol. 132, # 39, p. 13675 - 13683
[3] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 286 - 307
[4] Synthetic Communications, 2001, vol. 31, # 21, p. 3323 - 3328
[5] Patent: CN107556333, 2018, A. Location in patent: Paragraph 0076-0079 |
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