3-Benzyloxybenzaldehyde Chemical Properties

Melting point:

56-58 °C(lit.)

Boiling point:

180°C 0,08mm

Density 

1.1035 (rough estimate)

refractive index 

1.6000 (estimate)

Flash point:

180°C/0.08mm

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Fine Crystalline Powder

color 

White to light beige

Water Solubility 

Soluble in water 38.87 mg/L @ 25°C.

Sensitive 

Air Sensitive

BRN 

1956589

LogP

2.960 (est)

CAS DataBase Reference

1700-37-4(CAS DataBase Reference)

NIST Chemistry Reference

Benzyl 3-formylphenyl ether(1700-37-4)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29124990

MSDS

• Language:English Provider:3-Benzyloxybenzaldehyde
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Benzyloxybenzaldehyde Usage And Synthesis

Chemical Properties

WHITE TO LIGHT BEIGE FINE CRYSTALLINE POWDER

Uses

3-Benzyloxybenzaldehyde is used as a pharmaceutical intermediate. It activates the adenyl cyclase.

Synthesis

The general procedure for the synthesis of 3-(benzyloxy)benzaldehyde from benzyl bromide and m-hydroxybenzaldehyde was as follows: m-hydroxybenzaldehyde (3 g, 24.6 mmol) and anhydrous potassium carbonate (10.2 g, 73.8 mmol) were suspended in N,N-dimethylformamide (60 mL). Benzyl bromide (3.21 mL, 27.1 mmol) was added dropwise to this suspension and the reaction was stirred at room temperature for 14 hours. Upon completion of the reaction, the reaction mixture was poured into a mixture of ethyl acetate and water for liquid-liquid partitioning. The organic phase was separated, washed three times with water, the organic phase was dried with anhydrous magnesium sulfate, and the desiccant was removed by filtration. The filtrate was concentrated under reduced pressure and the resulting crude product was purified by silica gel column chromatography with an eluent ratio of heptane:ethyl acetate (4:1 to 1:1 gradient elution) to afford the target compound 3-(benzyloxy)benzaldehyde (5.16 g, 99% yield). The product was characterized by 1H-NMR (CDCl3) with the following chemical shift δ (ppm): 5.13 (2H, s, -OCH2-), 7.24-7.25 (1H, m, aryl ring H), 7.35-7.49 (8H, m, aryl ring H), 9.98 (1H, s, -CHO).

References

[1] Journal of the American Chemical Society, 1994, vol. 116, # 18, p. 8402 - 8403
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 7, p. 3188 - 3208
[3] Patent: US2007/105904, 2007, A1. Location in patent: Page/Page column 112
[4] Molecules, 2010, vol. 15, # 11, p. 7971 - 7984
[5] Journal of the American Chemical Society, 2001, vol. 123, # 22, p. 5382 - 5383

3-Benzyloxybenzaldehyde(1700-37-4)Related Product Information

• 4-Hydroxybenzaldehyde
• Benzyloxyacetyl chloride
• 4-Dimethylaminobenzaldehyde
• 2,3,4-Trimethoxybenzaldehyde
• Benzaldehyde
• 4-Methoxybenzylchloride
• p-Anisaldehyde
• p-Tolualdehyde
• 3-Benzyloxy-4-methoxybenzaldehyde
• 3,5-Dibenzyloxyacetophenone
• Tannic acid
• 3-Benzyloxy acetophenone
• M-(BENZOYLOXY)ACETOPHENONE
• PSOROMIC ACID
• 3,5-Dibenzyloxybenzaldehyde
• 3-BENZYLOXY-4-METHOXYBENZOIC ACID
• 3,4-Dibenzyloxybenzaldehyde
• Ellagic acid