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5447-02-9

Basic Information
CAS No.: 5447-02-9
Name: 3,4-Dibenzyloxybenzaldehyde
Article Data: 104
Molecular Structure:
Molecular Structure of 5447-02-9 (3,4-Dibenzyloxybenzaldehyde)
Formula: C21H18O3
Molecular Weight: 318.372
Synonyms: 3,4-dibenzyloxybenzaldehyde
EINECS: 226-662-2
Density: 1.176 g/cm3
Melting Point: 91-94 °C (dec.)(lit.)
Boiling Point: 492.4 °C at 760 mmHg
Flash Point: 243.9 °C
Appearance: off-white solid
Safety: 22-24/25
PSA: 35.53000
LogP: 4.65710
Synthetic route
100-44-7

benzyl chloride

139-85-5

3,4-dihydroxybenzaldehyde

5447-02-9

3,4-dibenzyloxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 15h;100%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 15h;99%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 130℃; for 4h;96%
100-39-0

benzyl bromide

139-85-5

3,4-dihydroxybenzaldehyde

5447-02-9

3,4-dibenzyloxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In acetone at 80℃; for 6h;97.4%
With potassium carbonate In acetonitrile for 24h; Reflux;96%
With potassium carbonate In acetonitrile for 24h; Reflux;96%
100-39-0

benzyl bromide

139-85-5

3,4-dihydroxybenzaldehyde

A

5447-02-9

3,4-dibenzyloxybenzaldehyde

B

4049-39-2

4-benzyloxy-3-hydroxy-benzaldehyde

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetone for 72h; Inert atmosphere; Reflux;A n/a
B 93%
Stage #1: 3,4-dihydroxybenzaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere;
Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0℃; for 6h; Inert atmosphere; regioselective reaction;

C23H24O4

5447-02-9

3,4-dibenzyloxybenzaldehyde

Conditions
ConditionsYield
With water In methanol at 25 - 30℃; for 0.333333h;92%
253336-68-4

3,4-bis(phenylmethoxy)-benzonitrile

5447-02-9

3,4-dibenzyloxybenzaldehyde

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene at -78℃; Inert atmosphere;92%
With diisobutylaluminium hydride In toluene at -78℃; for 3.5h;92%
150258-69-8

1,2-bis(benzyloxy)-4-(bromomethyl)benzene

5447-02-9

3,4-dibenzyloxybenzaldehyde

Conditions
ConditionsYield
With trihexyl (tetradecyl) phosphonium tetrafluoroborate; dihydrogen peroxide In water at 50℃; for 0.5h; Inert atmosphere;90%

acetic acid acetoxy-(3,4-bis-benzyloxy-phenyl)-methyl ester

5447-02-9

3,4-dibenzyloxybenzaldehyde

Conditions
ConditionsYield
β‐cyclodextrin In methanol; water at 60℃; for 8h; Product distribution;80%
100-39-0

benzyl bromide

139-85-5

3,4-dihydroxybenzaldehyde

A

5447-02-9

3,4-dibenzyloxybenzaldehyde

B

4049-39-2

4-benzyloxy-3-hydroxy-benzaldehyde

C

50773-56-3

3-benzyloxy-4-hydroxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 60℃; for 16h;A n/a
B 74%
C n/a
Stage #1: 3,4-dihydroxybenzaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere;
Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.75h; Inert atmosphere; regioselective reaction;
100-44-7

benzyl chloride

139-85-5

3,4-dihydroxybenzaldehyde

A

5447-02-9

3,4-dibenzyloxybenzaldehyde

B

4049-39-2

4-benzyloxy-3-hydroxy-benzaldehyde

C

50773-56-3

3-benzyloxy-4-hydroxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;A 6%
B 50%
C 9%
1486-54-0

3,4-dibenzyloxybenzoyl chloride

5447-02-9

3,4-dibenzyloxybenzaldehyde

Conditions
ConditionsYield
With quinoline; Pd-BaSO4; sulfur Hydrogenation.Reagens 4: Xylol;
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Specification

The 3,4-Dibenzyloxybenzaldehyde, with the CAS registry number 5447-02-9, is also known as NSC16747. It belongs to the product categories of Aromatic Aldehydes & Derivatives (substituted);Aromatics. Its EINECS registry number is 226-662-2. This chemical's molecular formula is C21H18O3 and molecular weight is 318.37. Its IUPAC name is called 3,4-bis(phenylmethoxy)benzaldehyde. This chemical is off-white solid. When you are using this chemical, please be cautious about it. You should not breathe its dust. In addition, you must avoid contacting it with skin and eyes.

Physical properties of 3,4-Dibenzyloxybenzaldehyde: (1)ACD/LogP: 4.92; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.92; (4)ACD/LogD (pH 7.4): 4.92; (5)ACD/BCF (pH 5.5): 3245.66; (6)ACD/BCF (pH 7.4): 3245.66; (7)ACD/KOC (pH 5.5): 11349.72; (8)ACD/KOC (pH 7.4): 11349.72; (9)#H bond acceptors: 3; (10)#Freely Rotating Bonds: 7; (11)Index of Refraction: 1.622; (12)Molar Refractivity: 95.33 cm3; (13)Molar Volume: 270.5 cm3; (14)Surface Tension: 47.4 dyne/cm; (15)Density: 1.176 g/cm3; (16)Flash Point: 243.9 °C; (17)Enthalpy of Vaporization: 75.93 kJ/mol; (18)Boiling Point: 492.4 °C at 760 mmHg; (19)Vapour Pressure: 7.7E-10 mmHg at 25°C.

Preparation: this chemical can be prepared by chloromethyl-benzene and 3,4-dihydroxy-benzaldehyde. This reaction will need reagent aq. NaI, K2CO3 and solvent aq. ethanol. The reaction time is 4.5 hours. The yield is about 94%.

Uses of 3,4-Dibenzyloxybenzaldehyde: it can be used to produce 2-(3,4-bis-benzyloxy-phenyl)-[1,3]dithiane. This reaction will need reagent HCl (gas) and solvent CHCl3 with reaction time of 1 hour. The yield is about 86%.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)COC2=C(C=C(C=C2)C=O)OCC3=CC=CC=C3
(2)InChI: InChI=1S/C21H18O3/c22-14-19-11-12-20(23-15-17-7-3-1-4-8-17)21(13-19)24-16-18-9-5-2-6-10-18/h1-14H,15-16H2
(3)InChIKey: XDDLXZHBWVFPRG-UHFFFAOYSA-N