Lithium triethylborohydride , 1MinTHF , 22560-16-3

Synonym(s):
Lithium triethylborohydride solution

CAS NO.：22560-16-3

Empirical Formula: C6H13BLi

Molecular Weight: 102.92

MDL number: MFCD00011703

EINECS: 245-076-8

PRODUCT Properties

• Melting point: 66-67° (Binger); mp 78-83° (dec) (Brown, 1977)
• Density: 0.892 g/mL at 25 °C
• Flash point: 1 °F
• storage temp.: Flammables + water-Freezer (-20°C)e area
• solubility: Miscible with tetrahydrofuran and benzene.
• form: Liquid
• color: Colorless to light gray
• Sensitive: Air & Moisture Sensitive
• Merck: 14,5544
• BRN: 4151240
• Exposure limits: ACGIH: TWA 50 ppm; STEL 100 ppm (Skin); OSHA: TWA 200 ppm(590 mg/m3); NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3)
• InChI: InChI=1S/C6H13B.Li/c1-4-7(5-2)6-3;/h4-7H,1-3H3;/q-1;+1
• InChIKey: NOLZOGXVNKCSTH-UHFFFAOYSA-N
• SMILES: [B+3]([H-])([CH-]C)([CH-]C)[CH-]C.[Li+]
• CAS DataBase Reference: 22560-16-3(CAS DataBase Reference)

Description and Uses

Lithium triethylborohydride is the organoboron compound with the formula LiEt3BH. Commonly referred to as LiTEBH or Superhydride, it is a powerful reducing agent used in organometallic and organic chemistry. It is a colorless or white liquid but is typically marketed and used as a THF solution. The related reducing agent sodium triethylborohydride is commercially available as toluene solutions.
LiBHEt3 is a stronger reducing agent than lithium borohydride and lithium aluminium hydride.

LiTEBH can be used as a reagent:

• To reduce alkyl halides to alkanes via dehydrogenation reactions.
• For the selective reduction of epoxides to Markovnikov alcohols.
• To reduce tosylates or mesylates primary alcohols to hydrocarbons.
• For reductive cyclization reactions for the preparation of useful intermediates.
• In the synthesis of hepta(manno-3-deoxy-6-O-t-butyldimethylsilyl)-β-cyclodextrin by reduction of hepta(manno-2,3-anhydro-6-O-t-butyldimethylsilyl)-β-cyclodextrin.
• For hydrodefluorination of C-F bonds using Ni catalyst.
• To prepare alkynyl alcohols from cleavage of cyclic keto-vinyl triflates.
• In the stereoselective reduction of bicyclic imides, isoquinolines, and pyridines.
• To prepare tungsten and molybdenum hydride complexes.

Safety

• Symbol(GHS): GHS02,GHS05,GHS07,GHS08
• Signal word: Danger
• Hazard statements: H318-H333-H225-H260-H302-H314-H335-H351
• Precautionary statements: P210-P231+P232-P280-P370+P378-P402+P404-P403+P235-P223-P303+P361+P353-P305+P351+P338-P405-P501a
• Hazard Codes: F,C
• Risk Statements: 11-14/15-19-34-40-37
• Safety Statements: 16-26-33-36/37/39-43-45
• RIDADR: UN 3399 4.3/PG 1
• WGK Germany: 1
• F: 10-23
• HazardClass: 4.3
• PackingGroup: I
• HS Code: 29319090
• Excepted Quantities: Not Permitted as Excepted Quantity