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348325

Sigma-Aldrich

Boron trichloride solution

1.0 M in heptane

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:
24861566
NACRES:
NA.22

form

liquid

Quality Level

100

reaction suitability

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

concentration

1.0 M in heptane

density

0.74 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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Application

  • Boron trichloride, a Lewis acid, is a general reagent for the cleavage of a wide range of ether and acetal protecting groups.
  • It is a useful reagent to directly convert aromatic aldehydes to the corresponding gem-dichlorides.
  • It can also be used in the transmetallation reaction with less nucleophilic reagents such as tin and zirconium organometallic compounds to synthesize a variety of organoboranes.

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

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Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Inhalation - Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 1B - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

supp_hazards

EUH014

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

35.6 °F - closed cup

flash_point_c

2 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR9175
SHBQ3744
SHBP2433
SHBQ0720
SHBM6661

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Migration of 1-alkenyl groups from zirconium to boron compounds.
Cole T E, et al.
Organometallics, 10(10), 3777-3781 (1991)
Boron Trichloride
Miyaura N, et al.
e-EROS Encyclopedia of Reagents for Organic Synthesis (2006)
Impact of Different Environmental Stimuli on the Release of 1-MCP from Boron-MCP Complexes.
Shahrin T, et al.
Journal of Plant Studies, 6(1), 46-46 (2016)
Conversion of aromatic aldehydes to gem-dichlorides using boron trichloride. A new highly efficient method for preparing dichloroarylmethanes.
Kabalka G W and Wu Z
Tetrahedron Letters, 41(5), 579-581 (2000)
Juan Xie et al.
Carbohydrate research, 340(3), 481-487 (2005-02-01)
Boron trichloride has been found to promote selective deprotection of 1,2- or 1,3-cis oriented secondary benzyl ethers of per-benzylated C-glycosyl derivatives. The reactivity towards BCl(3) follows the order: C-4>or=C-2>C-6>C-3 for C-glucopyranosyl derivatives and C-3>or=C-4>C-6>C-2 for C-galactopyranosyl derivatives. Preparatively useful selective
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