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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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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)
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)
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)
Warwick J Belcher et al.
Dalton transactions (Cambridge, England : 2003), (12)(12), 1602-1614 (2008-03-13)
The reactions of boron halides with free base porphyrins under conditions where partial hydrolysis of the boron halides can occur give diboron porphyrin complexes containing BOB moieties in which each boron is bonded to two porphyrin nitrogen atoms. BF(3).OEt(2) with
Dean Marković et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(20), 5969-5975 (2010-04-17)
The first ene reactions of SO(2) and unfunctionalized alkenes are reported. Calculations suggest that the endergonic ene reactions of SO(2) with alkenes can be used to generate beta,gamma-unsaturated sulfinyl and sulfonyl compounds. Indeed, in the presence of one equivalent of
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