PRODUCTS

BORANE, THF

Borane, THF can also be used to synthesize the chiral borane catalyst, which is used in the enantioselective halo-aldol reaction.
Borane, THF is used to prepare 9-unsubstituted acridines by reduction of corresponding acridones.
Borane, THF is used to reduce nylon surface amide groups to secondary amines.

CAS Number: 14044-65-6
EC Number: 237-881-8
MDL Number: MFCD00012429
IUPAC Name: Borane–tetrahydrofuran complex; boron, trihydro(tetrahydrofuran)-
Molecular Formula: C₄H₁₁BO
Molar Mass: 85.94 g/mol

SYNONYMS:
BH₃‑THF, BTHF, Borane‑THF, Trihydro(tetrahydrofuran)boron, THF‑borane complex, Borane tetrahydrofuran complex, Borane-THF (1:1), Boron hydride (BH3)-THF (1:1), Tetrahydrofuran-trihydroborane complex, Trihydrido(tetrahydrofuran)boron, 14044-65-6, Borane-tetrahydrofuran, Borane tetrahydrofuran, Tetrahydrofuran borane, tetrahydrofuran-borane, Boron, trihydro(tetrahydrofuran)-, (T-4)-, 5EAR4ERR1L, (TETRAHYDROFURAN)BORANE, BORANE-THF (1:1), TETRAHYDROFURAN-BORANE (1:1), TRIHYDRO(TETRAHYDROFURAN)BORANE, BORON HYDRIDE (BH3)-THF (1:1), DTXSID50930823, Tetrahydrofuran--borane, CCRIS 3411, BoraneTHF, EINECS 237-881-8, EC 237-881-8, DTXCID201359545, (T4)Trihydro(tetrahydrofuran)boron, Boron, trihydro(tetrahydrofuran), (T4), 237-881-8, Trihydro(tetrahydrofuran)boron, BH3.THF, boron;oxolane, boron; oxolane, borane THF, borane.THF, boron tetrahydrofuran, Borane tetrahydofuran, borane tetrahydrofurane, borane tetra hydrofuran, borane tetra-hydrofuran, borane tetrahydro-furan, borane- tetrahydrofuran, BH3THF, BH3-THF, BH3/THF, Boron hydride tetrahydrofuran, SCHEMBL42270, SCHEMBL379231, RMCYTHFAWCWRFA-UHFFFAOYSA-N, AKOS015833620, T2346, A807650, Q18384165, borane-tetrahydrofuran complex, tetrahydrofuran borane, bh3.thf, borane tetrahydrofuran complex solution, borane-d3-thf complex solution, borane-tetrahydrofuran, unii-5ear4err1l, oxolane borane, boron; oxolane, borane thf, (T-4)-Trihydro(tetrahydrofuran)boron, Borane, compound with tetrahydrofuran (1:1), (Tetrahydrofuran)borane, Borane-THF complex (1:1), Borane-tetrahydrofuran, Tetrahydrofuran borane, Trihydro(tetrahydrofuran)boron

Borane, THF is an adduct derived from borane and tetrahydrofuran (THF).
These solutions, which are colorless, are used for reductions and hydroboration, reactions that are useful in synthesis of organic compounds.
A common alternative to Borane, THF is borane–dimethylsulfide, which has a longer shelf life and effects similar transformations.

Borane, THF can reduce carboxylic acids to alcohols and is a common route for the reduction of amino acids to amino alcohols (e.g. valinol).
Borane, THF adds across alkenes to give organoboron compounds that are useful intermediates.
The following organoboron reagents are prepared from borane-THF: 9-borabicyclononane, Alpine borane, diisopinocampheylborane.

Borane, THF is also used as a source of borane (BH3) for the formation of adducts.
Borane, THF is a complex of borane with tetrahydrofuran, and is generally purchased as a solution in THF.
Borane, THF can decompose violently, therefore BH3-THF is typically only available in 1 M concentration.

It is recommended that Borane, 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 Borane, THF and is available in much higher concentrations (10 M).

USES and APPLICATIONS of BORANE, THF:
Borane, THF can be used as a reducing agent for the reduction of various functional groups such as carboxylic acids, aldehydes, ketones, esters, acid chlorides, nitriles, epoxides, amides, lactones, oximes, and imines into corresponding alcohols and amines.
Grignard reagents, arylmercury, arylthalium, and allyl and propargyllithium compounds react with Borane, THF to give organoboranes, which can be oxidized to the corresponding alcohols, phenols, and 1,3-diols.

Reducing agent: Borane, THF converts carboxylic acids, aldehydes, ketones, esters, nitriles, epoxides, amides, imines to alcohols/amines.
Hydroboration reagent: Borane, THF adds BH₂ groups to alkenes/alkynes for organic synthesis.
Specialized uses of Borane, THF: Synthesis of chiral catalysts, reduction of nylon amide groups, preparation of acridines.

Borane, THF is widely used as a reducing agent in organic synthesis.
Borane, THF is also used as a reagent in hydroboration reactions.

PREPARATION AND USES of BORANE, THF:
Borane, THF is commercially available but can also be generated by the dissolution of diborane in THF.
Alternatively, Borane, THF can be prepared by the oxidation of sodium borohydride with iodine in THF.

REACTIVITY of BORANE, THF:
Borane, THF is a Lewis-base complex of borane (BH₃) with THF, used as a stable alternative to diborane.
*Reactivity:
Borane, THF hydrolyzes on contact with water, releasing flammable H₂ and producing boric acid.
Sensitive to air and moisture; Borane, THF may form explosive peroxides in contact with oxygen or upon aging.

PHYSICAL and CHEMICAL PROPERTIES of BORANE, THF:
CAS Number: 14044-65-6
EC Number: 237-881-8
Appearance: Colorless liquid (or white solid at low temperatures)
Melting Point: −17 °C (or ~66 °C for solid form)
Boiling Point: ~35–66 °C (decomposes)
Density: ~0.898 g/mL at 25 °C
Flash Point: −17 °C (closed cup)
Auto‑Ignition Temperature: ~103 °C
Vapor Pressure: ~145 mmHg at 20 °C
Solubility: Reacts violently with water (releases H₂), miscible with THF

Linear Formula: BH3OC4H8
Molecular Weight: 85.94 g/mol
Beilstein Number: 3668402
MDL Number: MFCD00012429
UNSPSC Code: 12352005
PubChem Substance ID: 24850560
NACRES: NA.22

Physical State: Liquid
Color: Colorless
Odor: No data available
Melting / Freezing Point: No data available
Initial Boiling Point and Range: 65.5 - 66.5 °C
Flammability (solid, gas): No data available
Upper / Lower Flammability or Explosive Limits:
Upper 12.42 % (V), Lower 1.58 % (V)
Autoignition Temperature: No data available
Decomposition Temperature: No data available
pH: No data available

Viscosity, Kinematic: No data available
Viscosity, Dynamic: No data available
Water Solubility: No data available
Partition Coefficient (n-octanol/water): No data available
Vapor Pressure: No data available
Density: 0.898 g/cm³ at 25 °C
Relative Density: No data available
Relative Vapor Density: No data available
Particle Characteristics: No data available

Explosive Properties: Not classified as explosive
Oxidizing Properties: None
Other Safety Information: No data available
IUPAC Name: Oxolane borane
Molecular Formula: C4H11BO
InChI Key: RMCYTHFAWCWRFA-UHFFFAOYSA-N
SMILES: B.C1CCOC1
Synonym: Borane-tetrahydrofuran complex
Molecular Weight: 82.92 g/mol
Hydrogen Bond Donor Count: 0

Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 83.0668200 Da
Monoisotopic Mass: 83.0668200 Da
Topological Polar Surface Area: 9.2 Å²
Heavy Atom Count: 6
Formal Charge: 0
Complexity: 22.8
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0

Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 2
Compound Is Canonicalized: Yes
Molecular Formula: C4H11BO
Molecular Weight: 85.94
InChI: InChI=1S/C4H11BO/c5-6-3-1-2-4-6/h1-4H2,5H3
InChI Key: NPKJJCLQKCPGEZ-UHFFFAOYSA-N
SMILES: B+3([H-])([H-])[H-]

FIRST AID MEASURES of BORANE, THF:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of BORANE, THF:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.

FIRE FIGHTING MEASURES of BORANE, THF:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of BORANE, THF:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of BORANE, THF:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.

STABILITY and REACTIVITY of BORANE, THF:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available