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211249

Sigma-Aldrich

Boron trichloride solution

1.0 M in hexanes

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:
24852663
NACRES:
NA.22

vapor pressure

16.13 psi ( 55 °C)
5.22 psi ( 20 °C)

form

liquid

reaction suitability

core: boron
reagent type: catalyst

concentration

1.0 M in hexanes

density

0.738 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 (BCl3) is a commonly used reagent in organic synthesis for the cleavage of C-O bonds in a wide variety of ethers.

Application

BCl3 can be used as:       
  • A reagent in the synthesis of dichloroarylmethanes (geminal dichlorides) from aryl aldehydes.    
  • A Lewis acid for the preparation of syn chlorinated products by reacting aldehydes with α,β-unsaturated ketones in the presence of a Lewis base via Baylis–Hillman reaction.,·
  •  A catalyst to prepare (Z)-2-(1-trimethylgermyl-1-alkenyl)-1,3,2-dioxaborinanes by hydroboration reaction between 1-trimethylgermyl-1-alkynes with dichloroborane-methyl sulfide and 1,3-propane diol.

For preparing methyl esters of fatty acids and for transesterification of triglycerides.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system, Nervous system

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

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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A novel synthesis of (Z)-2-(1-trimethylgermyl-1-alkenyl)-1, 3, 2-dioxaborinanes and their conversion into carboxylic acids
Bhat NG, et al.
Tetrahedron Letters, 46(31), 5109-5111 (2005)
Titanium (IV) chloride, zirconium (IV) chloride or boron trichloride and phosphine-promoted Baylis-Hillman reaction of aldehydes with α , β -unsaturated ketone
Shi M, et al.
Journal of the Chemical Society. Perkin Transactions 1, (4), 390-393 (2001)
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)
Jayaraman Selvakumar et al.
Organic & biomolecular chemistry, 8(18), 4056-4058 (2010-07-29)
Isoindoloisoquinalinone, pyrroloisoquinolinone and benzo[a]quinolizinone units are constructed via intramolecular cyclization of the methoxy substituted N-phenethylimides using BBr(3).
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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