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5-tert-Butyl-2-hydroxybenzaldehyde

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Name

5-tert-Butyl-2-hydroxybenzaldehyde

EINECS N/A
CAS No. 2725-53-3 Density 1.072
PSA 37.30000 LogP 2.50220
Solubility N/A Melting Point 100-103 °C
Formula C11H14O2 Boiling Point 252.054 °C at 760 mmHg
Molecular Weight 178.231 Flash Point 103.964 °C
Transport Information N/A Appearance N/A
Safety 23-24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 2725-53-3 (5-TERT-BUTYL-2-HYDROXY-BENZALDEHYDE) Hazard Symbols N/A
Synonyms

Salicylaldehyde,5-tert-butyl- (6CI,7CI);2-Hydroxy-5-tert-butylbenzaldehyde;5-(1,1-Dimethylethyl)salicylaldehyde;5-tert-Butyl-2-hydroxybenzaldehyde;5-tert-Butylsalicylaldehyde;

Article Data 66

5-tert-Butyl-2-hydroxybenzaldehyde Synthetic route

50-00-0

formaldehyd

98-54-4

para-tert-butylphenol

2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
With triethylamine; magnesium chloride In acetonitrile for 3h; Heating;98%
With triethylamine; magnesium chloride In acetonitrile for 3h; Reflux;98%
With triethylamine; magnesium chloride In acetonitrile for 8h; Reflux;96%
98-54-4

para-tert-butylphenol

100-97-0

hexamethylenetetramine

2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
With trifluoroacetic acid at 80℃; for 24h; Inert atmosphere;61.06%
Stage #1: para-tert-butylphenol; hexamethylenetetramine With trifluoroacetic acid at 120℃; for 0.5h; Microwave irradiation;
Stage #2: With water; potassium carbonate
46%
With trifluoroacetic acid for 1.5h; Heating;29%
With acetic acid
With boric acid; glycerol
67-66-3

chloroform

98-54-4

para-tert-butylphenol

2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
With sodium hydroxide In water for 8h; Inert atmosphere; Reflux;42.5%
With sodium hydroxide In methanol; water at 65℃; for 2h;27.3%
With sodium hydroxide In methanol; water at 65 - 70℃; for 3h;25%
81441-06-7

2-aminomethyl-4-tert-butyl-phenol

2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
With hexamethylenetetramine In acetic acid for 4h; Heating;17%
98-54-4

para-tert-butylphenol

(CH2O)x

(CH2O)x

2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
Stage #1: para-tert-butylphenol With magnesium methanolate In methanol; toluene for 1h; Heating;
Stage #2: (CH2O)x In toluene at 110℃; for 3h;
Stage #3: With sulfuric acid In toluene at 60℃; for 1.5h;
98-54-4

para-tert-butylphenol

CH3MgO

2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
In methanol; toluene for 3h; Heating;
108-95-2

phenol

2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: zinc chloride / 180 °C
2: NaOH; water
View Scheme
64-17-5

ethanol

98-54-4

para-tert-butylphenol

2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
With chloroform; potassium hydroxide In water at 60℃; for 15h; Reimer-Tiemann Phenol Formylation;
50-00-0

formaldehyd

88-18-6

2-tert-Butylphenol

2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

Conditions
ConditionsYield
With triethylamine; magnesium chloride In tetrahydrofuran for 5h; Inert atmosphere; Reflux;
2725-53-3

2-hydroxy-5-t-butylbenzaldehyde

18162-48-6

tert-butyldimethylsilyl chloride

1108723-71-2

5-(tert-butyl)-2-((tert-butyldimethylsilyl)oxy)benzaldehyde

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 15h;100%
With 1H-imidazole In dichloromethane at 0℃; Sealed tube;
With 1H-imidazole In dichloromethane at 0℃; Sealed tube;
With dmap; triethylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;
With 1H-imidazole In N,N-dimethyl-formamide

5-tert-Butyl-2-hydroxybenzaldehyde Specification

The 5-tert-Butylsalicylaldehyde with cas registry number of 2725-53-3 is a kind of Aromatic compounds. Both its systematic name and IUPAC name are the same which is called 5-tert-butyl-2-hydroxybenzaldehyde. This chemical has irritation. Therefore, avoid contact with skin and eyes. And do not breathe vapour.

The physical properties about this chemical are: (1)ACD/LogP: 3.44; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.443; (4)ACD/LogD (pH 7.4): 3.402; (5)ACD/BCF (pH 5.5): 243.676; (6)ACD/BCF (pH 7.4): 221.363; (7)ACD/KOC (pH 5.5): 1777.984; (8)ACD/KOC (pH 7.4): 1615.178; (9)#H bond acceptors: 2#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.554; (12)Molar Refractivity: 53.275 cm3; (13)Molar Volume: 166.217 cm3; (14)Surface Tension: 39.003 dyne/cm; (15)Density: 1.072 g/cm3; (16)Flash Point: 103.964 °C; (17)Enthalpy of Vaporization: 50.918 kJ/mol; (18)Boiling Point: 252.054 °C at 760 mmHg; (19)Vapour Pressure: 0.012 mmHg at 25°C ; (20)Refractive index: n20/D 1.539(lit.).

Preparation of 5-tert-Butylsalicylaldehyde: it can be made by reaction of formaldehyde with 4-tert-butyl-phenol. The reaction will need reagents triethylamine, anhyd. MgCl2 and solvent acetonitrile at the condition of heating. The reaction time is 3 hours with 98% yield.

Uses of 5-tert-Butylsalicylaldehyde: it react with 2,2-dimethoxy-propane to produce 6-tert-butyl-2,4-dimethoxy-2-methyl-chroman. The reaction is a type of Condensation which needs reagent I2 and solvent CH2Cl2 with reaction time of 0.5 hour. The yield is about 83%.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(C)(C)c1ccc(c(c1)C=O)O;
(2)InChI: InChI=1/C11H14O2/c1-11(2,3)9-4-5-10(13)8(6-9)7-12/h4-7,13H,1-3H3;
(3)InChIKey: ZVCQQLGWGRTXGC-UHFFFAOYAF

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