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178934

Sigma-Aldrich

Boron trichloride solution

1.0 M in methylene chloride

Synonym(s):

Boron chloride, Trichloroborane

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About This Item

Empirical Formula (Hill Notation):
BCl3
CAS Number:
10294-34-5
Molecular Weight:
117.17
MDL number:
MFCD00011313
UNSPSC Code:
12352106
PubChem Substance ID:
24850781
NACRES:
NA.22

vapor pressure

29.72 psi ( 55 °C)
9.05 psi ( 20 °C)

Quality Level

200

form

liquid

reaction suitability

core: boron
reagent type: Lewis acid
reagent type: catalyst

concentration

1.0 M in methylene chloride

density

1.326 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

ClB(Cl)Cl

InChI

1S/BCl3/c2-1(3)4

InChI key

FAQYAMRNWDIXMY-UHFFFAOYSA-N

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General description

Boron trichloride is a boron halide. It participates in the hydroboration of alkenes. It forms strongly polarized donor-acceptor complexes with trimethyl- and triethylsilyl triflate. Boron trichloride assisted reaction between acid chlorides and alkynyltrifluoroborate salts have been reported to form ynones.

Boron trichloride solution is used as a Lewis acid catalyst in the synthesis of BN-phenanthrenes.

Application

Boron trichloride may be used in the synthesis of Cl-BODIPYs (BODIPY - Boron-dipyrromethene) and tris(dimethylamino)borane. It may be used in the synthesis of sceptrins and nakamuric acid.
For preparing methyl esters of fatty acids and for transesterification of triglycerides.

Packaging

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

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

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Carc. 2 - Eye Dam. 1 - Repr. 1B - Skin Corr. 1B - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Organometallic chemistry. 21. Silyl trifluoromethanesulfonate (triflate)-boron trichloride (tribromide) complexes.
Olah GA, et al.
Organometallics, 3(9), 1337-1340 (1984)
Hydroboration with boron halides and trialkylsilanes.
Soundararajan R and Matteson DS.
The Journal of Organic Chemistry, 55(8), 2274-2275 (1990)
Metal-Free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts.
Taylor C and Bolshan Y.
Organic Letters, 16(2), 488-491 (2013)
Bis (pinacolato) diboron.
Ishiyama T, et al.
Organometallic Syntheses, 77, 176-185 (2000)
Xiaolei Wang et al.
Organic chemistry frontiers : an international journal of organic chemistry, 2(8), 978-984 (2015-09-04)
Sceptrins and nakamuric acid are structurally unique antibiotics isolated from marine sponges. Recent studies suggest that the biosynthesis of these dimeric pyrrole-imidazole alkaloids involves a single-electron transfer (SET)-promoted [2+2] cycloaddition to form their cyclobutane core skeletons. We describe herein the
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