| Identification | More | [Name]
2-Benzyloxybenzaldehyde | [CAS]
5896-17-3 | [Synonyms]
2-BENZYLOXYBENZALDEHYDE
AKOS AU36-M26
ASISCHEM N43068
O-(BENZYLOXY)BENZALDEHYDE
OTAVA-BB BB7018801948
2-(Phenylmethoxy)benzaldehyde
CCY1a | [Molecular Formula]
C14H12O2 | [MDL Number]
MFCD00016583 | [Molecular Weight]
212.24 | [MOL File]
5896-17-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear pale yellow liquid | [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.)
| [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Chloroform, Methanol (Slightly) | [form ]
Liquid | [color ]
Colorless to yellow | [Specific Gravity]
1.339 | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29124990 | [Storage Class]
10 - Combustible liquids |
| Hazard Information | Back Directory | [Chemical Properties]
Clear pale yellow liquid | [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
| [Uses]
2-Benzyloxybenzaldehyde is used as an organic chemical synthesis intermediate. | [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 |
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