2-Benzyloxybenzaldehyde Chemical Properties

Melting point:

46-47°C

Boiling point:

326 °C (lit.)

Density 

1.339 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.6(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol (Slightly)

form 

Liquid

Specific Gravity

1.339

color 

Colorless to yellow

Water Solubility 

Insoluble in water.

Sensitive 

Air Sensitive

BRN 

780307

InChI

InChI=1S/C14H12O2/c15-10-13-8-4-5-9-14(13)16-11-12-6-2-1-3-7-12/h1-10H,11H2

InChIKey

PBEJTRAJWCNHRS-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=CC=C1OCC1=CC=CC=C1

CAS DataBase Reference

5896-17-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29124990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Benzyloxybenzaldehyde Usage And Synthesis

Chemical Properties

Clear pale yellow liquid

Uses

2-Benzyloxybenzaldehyde is used as an organic chemical synthesis intermediate.

Uses

2-Benzyloxybenzaldehyde may be used in the synthesis of:

• 2-benzyloxy-2′-hydroxy-3′,4′,6′-trimethoxychalcone
• N²-(2-benzyloxy)benzylidenyl isonicotinic acid hydrazide
• 2-hydroxy-2′-methoxybenzophenone
• 2′-hydroxy-5,6,7-trimethoxyflavone

General Description

2-Benzyloxybenzaldehyde is a benzaldehyde derivative. It undergoes enantioselective cyanoformylation with ethyl cyanoformate in the presence of a vanadium(V) chiral salen complex and imidazole to form the corresponding cyanohydrin carbonate.

Synthesis

(Preparation of 2-benzyloxybenzaldehyde) 185 g of N,N-dimethylformamide (DMF) and 82.8 g (0.6 mol) of anhydrous potassium carbonate were added to a three-necked flask, and 61 g (0.5 mol) of salicylaldehyde was added slowly dropwise under stirring. Subsequently, the reaction system was warmed up to 50 °C, and 75.9 g (0.6 mol) of benzyl chloride was slowly added dropwise at this temperature for a controlled dropwise time of 1 hour. After the dropwise addition was completed, the reaction mixture was warmed up to 70 °C and the reaction was continued with stirring for 2 hours. Upon completion of the reaction, the mixture was transferred to a partition funnel and washed sequentially with 185 g of toluene and 330 g of water. The organic phases were combined and the solvent was removed by distillation under reduced pressure (internal temperature 90 °C, pressure 10 mmHg) to give 104.5 g of the brown liquid product 2-benzyloxybenzaldehyde, which was analyzed to have a purity of 97.9% and a yield of 96.5%.

References

[1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 9, p. 2625 - 2636
[2] Patent: US6603029, 2003, B1
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 17, p. 3648 - 3661
[4] Patent: CN108822095, 2018, A. Location in patent: Paragraph 0121; 0122; 0123
[5] Tetrahedron, 2015, vol. 71, # 33, p. 5217 - 5228

2-Benzyloxybenzaldehyde(5896-17-3)Related Product Information

• 4-Hydroxybenzaldehyde
• o-Anisaldehyde
• 2,5-Dimethoxybenzaldehyde
• 2,6-Dimethoxybenzaldehyde
• 2,3-Dimethoxybenzaldehyde
• 2,4-Dimethoxybenzaldehyde
• 3,5-Dimethoxybenzaldehyde
• p-Anisaldehyde
• Veratraldehyde
• 2-(Trifluoromethyl)benzaldehyde
• 4-Methoxybenzylchloride
• 2-Nitrobenzaldehyde
• Salicylaldehyde
• 3-(METHOXYMETHOXY)BENZALDEHYDE
• (Trifluoromethoxy)benzene
• 4-Dimethylaminobenzaldehyde
• 2-Ethoxyphenol
• Benzaldehyde