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CAS RN: 850661-66-4 | Product Number: I0801

(S)-4-Isopropyl-3-(1-naphthylmethyl)-2,5,5-triphenyl-1,3,2-oxazaborolidine (ca. 6% in Toluene, ca. 0.1mol/L)


Purity:
Synonyms:
Documents:
10ML
€168.00
2   ≥20 

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Product Number I0801
Molecular Formula / Molecular Weight C__3__4H__3__2BNO = 481.45  
Physical State (20 deg.C) Liquid
Store Under Inert Gas Store under inert gas
Condition to Avoid Moisture Sensitive
Packaging and Container 10ML-Vial (View image)
CAS RN 850661-66-4
Reaxys Registry Number 10385893
PubChem Substance ID 160871411
Specifications
Appearance Colorless to Light yellow clear liquid
Concentration(HNMR) 5.0 to 8.0 w/w%
Functionality test to pass test
Properties (reference)
GHS
Pictogram Pictogram Pictogram Pictogram
Signal Word Danger
Hazard Statements H332 : Harmful if inhaled.
H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
H370 : Causes damage to organs.
H372 : Causes damage to organs through prolonged or repeated exposure.
H335 : May cause respiratory irritation.
H361d : Suspected of damaging the unborn child.
H336 : May cause drowsiness or dizziness.
H304 : May be fatal if swallowed and enters airways.
H225 : Highly flammable liquid and vapour.
Precautionary Statements P260 : Do not breathe dust/ fume/ gas/ mist/ vapours/ spray.
P210 : Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.
P201 : Obtain special instructions before use.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish.
P331 : Do NOT induce vomiting.
P308 + P311 : IF exposed or concerned: Call a POISON CENTER/doctor.
P301 + P310 : IF SWALLOWED: Immediately call a POISON CENTER/doctor.
Related Laws:
Transport Information:
UN Number UN1294
Class 3
Packing Group II
HS Number 2934999090
Application
An Efficient Asymmetric Organocatalyst for Regio- and Enantio-selective Diels-Alder Reactions

Typical procedure: To a dried Schlenk flask was charged CH2Cl2 (1.95 mL) and a 0.1 M solution of (S)-4-isopropyl-3-(1-naphthylmethyl)-2,5,5-triphenyl- 1,3,2-oxazaborolidine in CH2Cl2 (300 micro-L, 0.03 mmol) under argon atmosphere. After this solution cooled to -78 °C, a 0.1 M solution of 1-[bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzene in CH2Cl2 (250 micro-L, 0.025 mmol) was added dropwise. The solution was stirred for 15 minutes at the same temperature. To this catalyst solution was added ethyl acrylate (108 micro-L, 1.0 mmol) dropwise. After 1-2 minutes, mono-substituted cyclopentadiene (1.25 mmol) (1:1 (v/v) room temperature solution in CH2Cl2) was added dropwise. Upon completion, the reaction was quenched with 100 micro-L of Et3N at the same temperature. The reaction mixture was allowed to warm to room temperature and the solvent was removed in vacuo. The crude product was purified by flash column chromatography (elution with hexanes/ether = 30:1) to give (1R, 2R, 4R)-5-Methyl-bicyclo[2.2.1]hept- 5-ene-2-carboxylic acid ethyl ester (173 mg, 96% yield, 99 %ee).

References


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