triethylborane

• ChemBase ID: 129989
• Molecular Formular: C6H15B
• Molecular Mass: 97.9943
• Monoisotopic Mass: 98.12668088
• SMILES: B(CC)(CC)CC
• Canonical SMILES: CCB(CC)CC
• InChI: InChI=1S/C6H15B/c1-4-7(5-2)6-3/h4-6H2,1-3H3
• InChIKey: LALRXNPLTWZJIJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: triethylborane
• IUPAC Traditional name: triethylborane
• Synonyms: Triethylborane; triethylborine; triethylboron; Triethylborane; Triethylborane solution; Triethylborane, 1M soln. in THF; 三乙基硼; 三乙基硼 溶液; 三乙基硼烷, 1M THF溶液

Database IDs

• CAS Number: 97-94-9
• EC Number: 202-620-9
• MDL Number: MFCD00009022
• Beilstein Number: 1731462
• PubChem SID: 162224275; 24881503; 24855572; 24851669; 24850826
• PubChem CID: 7357
• Chemspider ID: 7079
• Wikipedia Title: Triethylborane

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.1847
• LogD (pH = 7.4): 3.1847
• Log P: 3.1847
• Molar Refractivity: 30.3477 cm^3
• Polarizability: 13.867316 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: N/A, Highly reactive in water
• Apperance: Colorless to pale yellow liquid
• Melting Point: -93 °C(lit.); -93°C
• Boiling Point: 95 °C(lit.); 95°C
• Flash Point: 1.4 °F; -17 °C; -17.22°C; -17°C(1°F); -32.8 °F; -36 °C
• Auto Ignition Point: -20 °C
• Density: 0.675 g/mL at 20 °C; 0.675 g/mL at 25 °C; 0.677 g/cm^3; 0.677 g/mL at 25 °C(lit.); 0.703 g/mL at 25 °C; 0.865; 0.865 g/mL at 25 °C
• Refractive Index: n20/D 1.380; n20/D 1.397(lit.)

Safety Information

• Storage Warning: Air Sensitive
• RTECS: ED2100000
• European Hazard Symbols: Corrosive (C); Flammable (F); Nature polluting (N)
• UN Number: 2845; 3399; UN2924
• German water hazard class: 3
• Hazard Class: 3; 4.2; 4.3
• Packing Group: 1; 2; II
• Risk Statements: 11-19-34; 11-19-34-37; 17-19-22-34-67; 17-22-34; 17-34; 17-34-48/20-51/53-62-65-67; R11 R14/15 R17 R19 R34 R35 R36/37
• Safety Statements: 16-26-36/37/39-45; 26-36/37/39-45; 26-36/37/39-45-61-62; 7-23-26-36/37/39-43-45; S6 S7/8 S16 S33 S36/37/39 S43A S45 S29
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• Main Hazard: Spontaneously flammable in air; causes burns
• GHS Hazard statements: H225-H250-H261-H314-H335; H225-H250-H301-H314; H225-H314-H318; H250-H261-H302-H304-H314-H336-H361f-H373-H411; H250-H301-H314; H250-H302-H314-H336
• GHS Precautionary statements: P210-P222-P231 + P232-P261-P280-P422; P210-P222-P231-P280-P301 + P310-P422; P210-P280-P305+P351+P338-P309-P310; P222-P231 + P232-P261-P273-P280-P422; P222-P231-P261-P280-P305 + P351 + P338-P422; P222-P231-P280-P301 + P310-P305 + P351 + P338-P422
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2845 4.2/PG 1; UN 3399 4.3/PG 2
• Supplemental Hazard Statements: May form explosive peroxides.

Product Information

• Purity: ≥95%
• Concentration: ~1 M in THF; ~15% in hexane; 1.0 M in hexanes; 1.0 M in THF; 1M soln. in THF; 2.0 M in diethyl ether
• Grade: purum
• Linear Formula: (C2H5)3B

DETAILS

Sigma Aldrich - 179701

Packaging
100, 800 mL in Sure/Seal™
Application
Catalyst for:
• Allylation of aldehydes1
• Decarboxylative C-C bond cleavage reactions2
• Rhenium hydride / boron Lewis acid cocatalysis of alkene hydrogenations3
• Regioselective hydroxyalkylation of unsaturated oxime ethers4Reactant for radical reductions of alkyl bromides with N-heterocyclic carbene boranes5Reactant for synthesis of tetramethylammonium trialkylphenylborate salts with oxidation potential6

Sigma Aldrich - 195030

Packaging
100, 800 mL in Sure/Seal™
Application
Catalyst for:
• Allylation of aldehydes1
• Decarboxylative C-C bond cleavage reactions2
• Rhenium hydride / boron Lewis acid cocatalysis of alkene hydrogenations3
• Regioselective hydroxyalkylation of unsaturated oxime ethers4Reactant for radical reductions of alkyl bromides with N-heterocyclic carbene boranes5Reactant for synthesis of tetramethylammonium trialkylphenylborate salts with oxidation potential6

Sigma Aldrich - 594377

Packaging
100 mL in Sure/Seal™
Application
Catalyst for:
• Allylation of aldehydes1
• Decarboxylative C-C bond cleavage reactions2
• Rhenium hydride / boron Lewis acid cocatalysis of alkene hydrogenations3
• Regioselective hydroxyalkylation of unsaturated oxime ethers4Reactant for radical reductions of alkyl bromides with N-heterocyclic carbene boranes5Reactant for synthesis of tetramethylammonium trialkylphenylborate salts with oxidation potential6

Sigma Aldrich - 257192

Packaging
100 g in Sure-Pac™
Application
Reagent for:
• Enantioselective umpolung allylation of aldehydes1
• Preparation of tetramethylammonium trialkylphenylborate salts2Catalyst for:
• Radical reductions of alkyl bromides and iodides bearing electron withdrawing groups with N-heterocyclic carbene boranes3
• Synthesis of 1-substituted pyrrolines by N-diallylation of amines and ring-closing metathesis4
• Decarboxylative C-C bond cleavage reactions5
• Alkene hydrogenations6
• Aminyl radical cyclizations onto silyl enol ethers7Modifier for single-site organochromium ethylene polymerization catalysts8
Used with lithium tri-tert-butoxyaluminohydride (cat. no. L2904) in the reductive cleavage of ethers and epoxides. Used in the deoxygenation of primary and secondary alcohols.
Recommended products
Angled septum-inlet adapter Z118206 or straight septum-inlet adapter, 6mm I.D. inlet, Z118141 or straight septum-inlet adapter, 13mm I.D. inlet, Z118192 is recommended.

Sigma Aldrich - 90371

Application
Catalyst for:
• Allylation of aldehydes1
• Decarboxylative C-C bond cleavage reactions2
• Rhenium hydride / boron Lewis acid cocatalysis of alkene hydrogenations3
• Regioselective hydroxyalkylation of unsaturated oxime ethers4Reactant for radical reductions of alkyl bromides with N-heterocyclic carbene boranes5Reactant for synthesis of tetramethylammonium trialkylphenylborate salts with oxidation potential6

Sigma Aldrich - 90369

Application
Catalyst for:
• Allylation of aldehydes1
• Decarboxylative C-C bond cleavage reactions2
• Rhenium hydride / boron Lewis acid cocatalysis of alkene hydrogenations3
• Regioselective hydroxyalkylation of unsaturated oxime ethers4Reactant for radical reductions of alkyl bromides with N-heterocyclic carbene boranes5Reactant for synthesis of tetramethylammonium trialkylphenylborate salts with oxidation potential6

REFERENCES

• Radical initiator for hydrostannylation of alkynes: Tetrahedron, 45, 923 (1989).
• Reacts with metal enolates to give the enoxytriethylborates, useful in selective alkylation and aldol reactions: Tetrahedron Lett., 2975 (1976); 32, 5521 (1991).