Conditions | Yield |
---|---|
With C16H25N3O2S In n-heptane for 48h; Reflux; Molecular sieve; Inert atmosphere; | 98% |
With tetrabutylammonium acetate; oxiranyl-methanol In hexane for 24h; Reflux; | 97% |
With tetramethylammonium methyl carbonate In hexane for 2h; Reagent/catalyst; Time; Molecular sieve; Reflux; Green chemistry; | 92% |
Conditions | Yield |
---|---|
With potassium fluoride at 150℃; for 2h; Reagent/catalyst; Temperature; | 96.36% |
With ethanol; copper | |
With diethylamine at 130 - 140℃; |
benzyl chloride
N,N-diisopropylethylamine hydrochloride
benzyl salicylate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine | 95.5% |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 40℃; | 95% |
Stage #1: salicylic acid With sodium hydrogencarbonate In N,N-dimethyl-formamide at 70℃; for 0.166667h; Stage #2: benzyl bromide In N,N-dimethyl-formamide for 4h; | 94% |
With sodium hydrogencarbonate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 40℃; for 0.666667h; | 88% |
Conditions | Yield |
---|---|
With K5 In toluene at 85℃; for 8h; | 95% |
benzyl 2-(benzyloxy)benzoate
benzyl salicylate
Conditions | Yield |
---|---|
With methyl-phenyl-thioether; trifluoroacetic acid In toluene at 20℃; for 0.0833333h; | 93% |
Conditions | Yield |
---|---|
In 1,2-dichloro-benzene at 180℃; for 4h; chemoselective reaction; | 93% |
Conditions | Yield |
---|---|
With di-tert-butyl peroxide; C11H23N2(1+)*Br4Fe(1-) at 110℃; for 24h; | 87% |
Conditions | Yield |
---|---|
With di(n-butyl)tin oxide In methanol for 5h; Heating; | 86% |
Conditions | Yield |
---|---|
With nnano-SiO2-supported Preyssler heteropolyacid In dichloroethane at 80℃; for 0.05h; Microwave irradiation; | 74% |
With aluminium trichloride; sodium iodide In acetonitrile for 1.5h; Heating; | 64% |
With 1,1'-carbonyldiimidazole In acetonitrile at 65℃; for 3h; | 64% |
With 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt for 15h; Heating; | |
With ionic liquid based on Keggin (H3PW12O40) heteroployacid for 0.0333333h; Catalytic behavior; Concentration; Microwave irradiation; Green chemistry; |
Conditions | Yield |
---|---|
With triethylamine at 90℃; for 2h; | 65% |
Conditions | Yield |
---|---|
With 1,1'-carbonyldiimidazole In dichloromethane at 25℃; for 12h; Solvent; Inert atmosphere; | A 15% B 55% C 7% |
aspirin
benzyl alcohol
A
Benzyl acetate
B
benzyl salicylate
C
2-acetoxybenzoic acid benzyl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; for 19h; Inert atmosphere; | A 40% B 8% C 41% |
2-benzyloxybenzoic acid
A
benzyl salicylate
C
salicylic acid
D
phenol
Conditions | Yield |
---|---|
at 190℃; |
Conditions | Yield |
---|---|
at 130 - 140℃; |
Conditions | Yield |
---|---|
In chloroform; benzene for 1.5h; Heating; Yield given; |
Conditions | Yield |
---|---|
In chloroform; benzene for 1.5h; Heating; Yield given; |
Conditions | Yield |
---|---|
With salicylic acid at 200℃; im geschlossenen Rohr; |
Conditions | Yield |
---|---|
at 130 - 140℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: K2CO3 / TEBAC / benzene; CHCl3 / 0.67 h / Heating 2: benzene; CHCl3 / 1.5 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: K2CO3 / TEBAC / benzene; CHCl3 / 0.33 h / Heating 2: benzene; CHCl3 / 1.5 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 12 h / 25 °C / Inert atmosphere 2: dmap / dichloromethane / 12 h / 25 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 19 h / 0 - 25 °C / Inert atmosphere 2: dmap / dichloromethane / 12 h / 25 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 12 h / 0 - 25 °C / Inert atmosphere 2: pyridine / dichloromethane / 12 h / 25 °C / Inert atmosphere 3: dmap / dichloromethane / 12 h / 25 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 2: dmap / dichloromethane / 12 h / 25 °C / Inert atmosphere View Scheme |
2-acetoxybenzoic acid benzyl ester
benzyl salicylate
Conditions | Yield |
---|---|
With dmap In dichloromethane at 25℃; for 12h; Reagent/catalyst; Solvent; Inert atmosphere; |
Conditions | Yield |
---|---|
With graphene oxide supported quaternary ammonium salt at 120℃; for 8h; |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 100% |
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Ambient temperature; | 96% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 18h; | 96% |
ethyl 5-bromovalerate
benzyl salicylate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile Reflux; | 94% |
benzyl salicylate
trans-4-guanidinomethylcyclohexanecarboxylic acid hydrochloride
2'-benzyloxycarbonylphenyl trans-4-guanidinomethylcyclohexanecarboxylate hydrochloride
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In pyridine; N,N-dimethyl-formamide | 89% |
bis(trichloromethyl) carbonate
benzyl salicylate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; triethylamine In tetrahydrofuran; dichloromethane; water at 0 - 20℃; for 2.5h; Inert atmosphere; | 89% |
benzyl salicylate
Z-DL-Phe-OH
2-(N-benzyloxycarbonyl-DL-phenylalanyloxy)-benzoic acid benzyl ester
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 24h; | 88% |
benzyl salicylate
2-Methoxybenzoic acid
A
benzyl 2-methoxybenzoate
B
salicylic acid
Conditions | Yield |
---|---|
Stage #1: 2-Methoxybenzoic acid With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.5h; Stage #2: benzyl salicylate at 110℃; for 24h; | A 87% B n/a |
6-bromo-hexanoic acid ethyl ester
benzyl salicylate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile Reflux; | 86% |
Conditions | Yield |
---|---|
With iodine; aluminium In acetonitrile at 80℃; for 18h; | 86% |
isocyanate de chlorosulfonyle
benzyl salicylate
benzyl O-carbamoylsalicylate
Conditions | Yield |
---|---|
In dichloromethane for 2h; Ambient temperature; | 85% |
(S)-1-(2-phenylacetyl)pyrrolidine-2-carboxylic acid
benzyl salicylate
(S)-1-Phenylacetyl-pyrrolidine-2-carboxylic acid 2-benzyloxycarbonyl-phenyl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; | 85% |
Conditions | Yield |
---|---|
With di-tert-butyl-diazodicarboxylate; triethylamine; triphenylphosphine In dichloromethane at 0℃; for 2.5h; intermolecular Mitsunobu reaction; | 84% |
Conditions | Yield |
---|---|
With caesium carbonate; N-ethyl-N,N-diisopropylamine at 40℃; for 12h; Molecular sieve; | 84% |
With silver(l) oxide In quinoline at 20℃; for 1h; Koenigs-Knorr Glycosidation; | 80% |
benzyl salicylate
(4S)-1-butyryl-4-<(carboxymethyl)methylamino>-L-proline 4-tert-butyl ester
(4S)-1-butyryl-4-<(carboxymethyl)methylamino>-L-proline 4-tert-butyl ester 2-ester with benzyl salicylate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; | 83% |
benzyl salicylate
methyl dichlorophosphoridate
bis(2-(benzyloxycarbonyl)phenyl) methyl phosphate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 0.5h; Ambient temperature; | 82% |
With sodium hydride 1.) THF, RT, 1 h, 2.) THF, RT, overnight; Yield given. Multistep reaction; |
Clofibric acid
benzyl salicylate
benzyl O-<2-(p-chlorophenoxy)-2-methylpropionyl>salicylate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; | 78% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 24h; Inert atmosphere; | 78% |
benzyl salicylate
(S)-1-(3,3-dimethylbutanoyl)pyrrolidine-2-carboxylic acid
(S)-1-(3,3-Dimethyl-butyryl)-pyrrolidine-2-carboxylic acid 2-benzyloxycarbonyl-phenyl ester
Conditions | Yield |
---|---|
With dmap In dichloromethane Ambient temperature; | 77% |
benzyl salicylate
N-((benzyloxy)carbonyl)-L-phenylalaninol
C31H29NO5
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 0℃; for 2h; Mitsunobu reaction; | 77% |
Reported in EPA TSCA Inventory.
1.Introduction of Benzyl salicylate
Benzyl salicylate, with its CAS NO 118-58-1, is a kind of Colorless clear liquid. It has synonyms of 2-Hydroxybenzoic acid phenylmethyl ester ; Benzyl o-hydroxybenzoate and salicylic acid benzyl ester . Benzyl salicylate should be stored in shady and cool warehouse and mainly used in cosmetics and flavors.
2.Properties of Benzyl salicylate
(1) Boiling point: 320 °C at 760 mmHg (2) Flash Point: 146.4 °C (3) Density: 1.224 g/cm3
(4) Refractive index: n20/D 1.581(lit.) (5) Water Solubility: Slightly soluble (6) Index of Refraction: 1.607
(7) Molar Refractivity: 64.39 cm3 (8) Molar Volume: 186.4 cm3 (9) Surface Tension: 51.4 dyne/cm
(10) Enthalpy of Vaporization: 58.4 kJ/mol (11) Vapour Pressure: 0.000175 mmHg at 25°C (12) XLogP3-AA: 3.2
(13) H-Bond Donor: 1 (14) H-Bond Acceptor: 3
3.Structure descriptors of Benzyl salicylate
IUPAC Name: benzyl 2-hydroxybenzoate
Canonical SMILES: C1=CC=C(C=C1)COC(=O)C2=CC=CC=C2O
InChI: InChI=1S/C14H12O3/c15-13-9-5-4-8-12(13)14(16)17-10-11-6-2-1-3-7-11/h1-9,15H,10H2
InChIKey: ZCTQGTTXIYCGGC-UHFFFAOYSA-N
4.Safety information of Benzyl salicylate
Hazard Codes:
Risk Statements 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-36-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S24/25:Avoid contact with skin and eyes.
WGK Germany 2
RTECS VO1750000
5.Toxity data of Benzyl salicylate
1. | orl-rat LD50:2227 mg/kg | FCTXAV Food and Cosmetics Toxicology. 11 (1973),1029. |
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