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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

Signal Word

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

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

35.6 °F - closed cup

Flash Point(C)

2 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Poisonous substance

PRTR

Class I Designated Chemical Substances

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

348325-800ML:4548173138732
348325-VAR:
348325-100ML:4548173138725
348325-BULK:
348325-4X25ML:4548173314969

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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)
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)
Boron Trichloride
Miyaura N, et al.
e-EROS Encyclopedia of Reagents for Organic Synthesis (2006)
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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