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Merck
CN

298425

Sigma-Aldrich

Tributylborane

Synonym(s):

TBB, Tributylboron

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About This Item

Linear Formula:
[CH3(CH2)3]3B
CAS Number:
122-56-5
Molecular Weight:
182.15
EC Number:
204-554-6
MDL number:
MFCD00009423
UNSPSC Code:
12352001
PubChem Substance ID:
24857985
NACRES:
NA.22

Key Documents

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reaction suitability

reagent type: reductant

bp

109 °C/20 mmHg (lit.)

density

0.747 g/mL at 25 °C (lit.)

SMILES string

CCCCB(CCCC)CCCC

InChI

1S/C12H27B/c1-4-7-10-13(11-8-5-2)12-9-6-3/h4-12H2,1-3H3

InChI key

CMHHITPYCHHOGT-UHFFFAOYSA-N

Application

Reactant for:
  • Addition reactions for synthesis of phenyltrialkylborate salts
  • Boron-based multicomponent reactions for generation of substituted aziridines, oxazolidines, and pyrrolidines
  • Suzuki-Miyaura cross coupling of halopurines with trialkylboranes for the synthesis of adenosine A2A receptor antagonists
  • Multicomponent C-alkylation reactions with aromatic aldimines
  • One-pot alkylation-boration and electrophilic substitution

Packaging

Supplied in a Sure/Pac™ cylinder and has a 1/4-turn bronze ball valve with a female 1/4" NPT outlet thread (Z122661) installed. Before using the cylinder, ensure that the valve is closed, then remove carbon steel plug that seals the outlet valve.

Compatible with the following:
For instructions please refer to technical bulletin AL-136: The Aldrich Sure/Pac™ Cylinder System

Legal Information

Aldrich is a registered trademark of Sigma-Aldrich Co. LLC
Sure/Pac is a trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Hazard Statements

H250,H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Pyr. Liq. 1 - Skin Corr. 1B

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBG9723V
SHBC9794V
SHBB1471V
06911DJ
00212ED

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Tetrahedron Letters, 33, 3779-3779 (1992)
Tetrahedron Letters, 35, 7201-7201 (1994)
S M Moerlein et al.
Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine, 44(9), 1213-1218 (1993-09-01)
Because [15O]butanol is the radiopharmaceutical of choice for PET studies of cerebral perfusion and neurological activation, we have developed a microprocessor-controlled radiosynthetic system for the preparation of this radiotracer in up to ten batches at a time. An IBM-compatible minicomputer
The Journal of Organic Chemistry, 59, 5530-5530 (1994)
R M Carvalho et al.
Journal of dental research, 82(8), 597-601 (2003-07-30)
Re-expansion of dried demineralized dentin is required to optimize resin adhesion. This study tested the hypothesis that bond strengths to dentin depend upon the ability of experimental HEMA(2-hydroxy-ethyl-methacrylate)/solvent primers to re-expand the matrix. Dentin surfaces were acid-etched with 37% phosphoric
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