Borane-tetrahydrofuran complex
- CAS NO.:14044-65-6
- Empirical Formula: C4H11BO
- Molecular Weight: 85.94
- MDL number: MFCD00012429
- EINECS: 237-881-8
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-04-23 13:52:06
What is Borane-tetrahydrofuran complex?
Description
Borane tetrahydrofuran complex (BH3-THF) is widely used as a reducing agent in organic synthesis. It is also used as a reagent in hydroboration reactions.It is a charge-transfer complex that is a useful surrogate for diborane1 in organic synthesis. It can be used to reduce carboxylic acids to alcohols or nitriles to primary amines. It reacts with olefins to add the BH2 functional group. Alkyl- or arylboranes formed in this way can further react with unsaturated compounds such as olefins, imines, ketones, and alkynes (the hydroboration reaction) to make useful boron-containing intermediates.
Description
Borane–tetrahydrofuran (BH3–THF) is a charge-transfer complex that is a useful surrogate for diborane1 in organic synthesis. It can be used to reduce carboxylic acids to alcohols or nitriles to primary amines. It reacts with olefins to add the BH2 functional group. Alkyl- or arylboranes formed in this way can further react with unsaturated compounds such as olefins, imines, ketones, and alkynes (the hydroboration reaction) to make useful boron-containing intermediates.
Charge-transfer complexes such as BH3–THF form when a Lewis base (THF in this case) “donates” its unshared electron pair to an electron-deficient Lewis acid such as borane. The electrostatic attraction between the components is not as strong as a covalent bond; but in many cases it is sufficient to make the complex behave as a covalent compound. As an example, BH3–THF can be distilled without decomposing.
BH3–THF’s relative stability makes it a convenient way to use extremely toxic and flammable diborane. But it is not without its own risks. In particular, it reacts violently with water to produce copious amounts of hydrogen. As a result, BH3–THF is normally sold as a 1 M (≈10 wt%) solution in THF. It is available from numerous chemical supply houses worldwide.
1. Under standard conditions, borane dimerizes to produce the more electronically stable diborane.
Description
Borane-tetrahydrofuran (BH3-THF) is a complex of borane with tetrahydrofuran, and is generally purchased as a solution in THF. BH3-THF can decompose violently, therefore BH3-THF is typically only available in 1 M concentration. It is recommended that BH3-THF solutions be stored at 0-5 C, and that reactions are performed at under 35 C. Borane-dimethylsulfide (BH3-SMe2) is more stable than BH3-THF and is available in much higher concentrations (10 M).
The Uses of Borane-tetrahydrofuran complex
Borane-tetrahydrofuran complex is used to reduce Nylon surface amide groups to secondary amines.It is an important reagent used in the reduction of certain functional groups viz. aldehyde, ketone, carboxylic acid, amide, oxime, imine and nitrile. It is also used as hydro borating agent. It acts as a borane source for oxazaborolidine catalyzed asymmetric reductions.
The Uses of Borane-tetrahydrofuran complex
To a 0.24M THF suspension of the SM (71.7 mmol) at 0 C was added BH3-THF (1M, 220 mmol). The reaction mixture was stirred under Ar at RT for 66 h then quenched by addition of EtOH (15 mL) at 0 C and stirred an additional 15 min. The mixture was poured into H2O and extracted with DCM. The combined organics were washed with brine, dried (Na2SO4), and concentrated to provide the crude product as a white solid. [10.16 g, 62%]
Properties of Borane-tetrahydrofuran complex
Melting point: | -17 °C |
Boiling point: | 35 °C |
Density | 0.898 g/mL at 25 °C |
Flash point: | 1 °F |
storage temp. | Store at <= 20°C. |
solubility | reacts violently |
appearance | colorless liquid |
form | Liquid |
color | Colorless |
Water Solubility | REACTS |
Sensitive | Air & Moisture Sensitive |
Safety information for Borane-tetrahydrofuran complex
Signal word | Danger |
Pictogram(s) |
Flame Flammables GHS02 Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07 Health Hazard GHS08 |
GHS Hazard Statements |
H225:Flammable liquids H260:Substances And Mixtures Which, In Contact With Water,Emit Flammable Gases H302:Acute toxicity,oral H315:Skin corrosion/irritation H318:Serious eye damage/eye irritation H319:Serious eye damage/eye irritation H333:Acute toxicity,inhalation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation H351:Carcinogenicity |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P223:Keep away from any possible contact with water, because of violent reaction and possible flash fire. P280:Wear protective gloves/protective clothing/eye protection/face protection. P231+P232:Handle under inert gas. Protect from moisture. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P370+P378:In case of fire: Use … for extinction. P405:Store locked up. P402+P404:Store in a dry place. Store in a closed container. P403+P235:Store in a well-ventilated place. Keep cool. |
Computed Descriptors for Borane-tetrahydrofuran complex
Abamectin manufacturer
Sanpra Synthesis Private Limited
JLS Laboratories Pvt Limited
SREEGANAPHARMACEUTICALS
VASISTA LIFE SCIENCES PRIVATE LIMITED
Oceanic Pharmachem Pvt Ltd
AMINO ORGANICS
JSK Chemicals
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