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Trimethylboroxine

Product Name
Trimethylboroxine
CAS No.
823-96-1
Chemical Name
Trimethylboroxine
Synonyms
2,4,6-triMethyl-1,3,5,2,4,6-trioxatriborinane;2,4,6-Trimethylboroxin;2,4,6-Tr;METHYLBOROXIN;TRIMETHYLBOROXINE;trimethylboroxin,;TRIMEETHYLBOROXINE;Methylboric anhydride;Trimethylcyclotriborane;Methaneboronic anhydride
CBNumber
CB0104810
Molecular Formula
C3H9B3O3
Formula Weight
125.53
MOL File
823-96-1.mol
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Trimethylboroxine Property

Melting point:
−38 °C(lit.)
Boiling point:
78-80 °C(lit.)
Density 
0.898 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.362(lit.)
Flash point:
16 °F
storage temp. 
Flammables area
solubility 
Chloroform (Sparingly), Dichloromethane (Slightly), THF (Soluble)
form 
Solution
color 
Colorless to yellow
Water Solubility 
Not miscible in water.
Sensitive 
Moisture Sensitive & Hygroscopic
BRN 
1757008
Exposure limits
ACGIH: TWA 50 ppm; STEL 100 ppm (Skin)
OSHA: TWA 200 ppm(590 mg/m3)
NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3)
InChIKey
GBBSAMQTQCPOBF-UHFFFAOYSA-N
CAS DataBase Reference
823-96-1(CAS DataBase Reference)
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Safety

Hazard Codes 
F,C,Xi
Risk Statements 
11-34-41-37/38-19
Safety Statements 
9-16-26-33-36/37/39-45-46-37/39-3
RIDADR 
UN 2924 3/PG 2
WGK Germany 
3
2-10-21
TSCA 
Yes
HazardClass 
3.1
PackingGroup 
II
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H314Causes severe skin burns and eye damage

H335May cause respiratory irritation

H351Suspected of causing cancer

Precautionary statements

P201Obtain special instructions before use.

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P370+P378In case of fire: Use … for extinction.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
903965
Product name
Trimethylboroxine
Purity
50% THF solution
Packaging
5ML
Price
$59.2
Updated
2024/03/01
Sigma-Aldrich
Product number
903965
Product name
Trimethylboroxine
Purity
50% THF solution
Packaging
25ML
Price
$231
Updated
2024/03/01
Sigma-Aldrich
Product number
903965
Product name
Trimethylboroxine
Purity
50% THF solution
Packaging
250ML
Price
$1290
Updated
2024/03/01
Sigma-Aldrich
Product number
323136
Product name
Trimethylboroxine
Purity
99%
Packaging
1g
Price
$20.8
Updated
2024/03/01
Sigma-Aldrich
Product number
323136
Product name
Trimethylboroxine
Purity
99%
Packaging
5g
Price
$131
Updated
2024/03/01
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Trimethylboroxine Chemical Properties,Usage,Production

Chemical Properties

colorless to yellow solution

Uses

Trimethylboroxine is used as a derivatizing agent for GLC analysis. It is used in a diverse array of areas, including as a polymerization additive. It is also used in the preparation of CBS catalysts for asymmetric reductions.

Uses

Trimethylboroxine (TMB) is a cyclic anhydride of methyl-boronic acid. It can be used as a:

  • Methylating agent for the methylation of various aromatic halides and C(sp3)?H bonds using palladium catalyst.
  • Reagent in the preparation of polymer supported CBS (Corey, Bakshi, and Shibata) catalysts.

Uses

Trimethylboroxine (TMB) is a cyclic anhydride of methyl-boronic acid. It can be been used:

  • As a derivatizing agent for gas chromatographic/mass spectrometric analysis.
  • In the preparation of methylaluminoxane (MAO) which is used in the polymerization of olefins.
  • As an electrolyte additive to enhance the interface stability of electrode/electrolyte.
  • In methylation of aryl halides by palladium-catalyzed Suzuki-Miyaura coupling reaction.
  • In the preparation of CBS (Corey, Bakshi and Shibata) catalysts for asymmetric reductions of ketones to alcohols.

Preparation

Trimethylboroxine is prepared by heating B(CH3)3 and B2O3 together in a sealed tube. The B2O3 powder is made by dehydrating H3BO3 under vacuum over P2O5 , at 220℃. The very hygro-scopic oxide is placed with strict exclusion of moisture in a 200-ml. thick-wall Pyrex tube provided with a ground joint, and a melting-point capillary is fastened to the tube just below the joint. The tube is connected to a vacuum pump and immersed in liquid nitrogen, and when a high vacuum has been established, a quantity of B(CH3)3 equivalent to 4.25 g. (0.061 mole) of B2O3 is condensed in the tube. The tube is sealed off, heated to 600℃ and kept at this temperature for six hours; in the process the contents turn into a clear, colorless liquid. When the tube has cooled down, the tip is broken under a nitrogen blanket and sealed to a tube leading to the vacuum pump. The tube is evacuated and the contents of the tube are transferred into a -78℃ trap. The crude product is purified by removing volatile contaminants at -45℃ and then distilling the product from a -10℃ trap into a receiver held at -78℃.

Application

Trimethylboroxine (TMB) is a cyclic anhydride of methyl-boronic acid. It can be been used:
As a derivatizing agent for gas chromatographic/mass spectrometric analysis.
In the preparation of methylaluminoxane (MAO) which is used in the polymerization of olefins.
As an electrolyte additive to enhance the interface stability of electrode/electrolyte.
In methylation of aryl halides by palladium-catalyzed Suzuki-Miyaura coupling reaction.
In the preparation of CBS (Corey, Bakshi and Shibata) catalysts for asymmetric reductions of ketones to alcohols.

Purification Methods

Possible impurity is methylboronic acid. If present, then add a few drops of conc H2SO4 and distil it immediately, then fractionate it through an efficient column. [McCusker et al. J Am Chem Soc 79 5179 1957, IR: Goubeau & Keller Z Anorg Allgem Chem 272 303 1953, Beilstein 4 IV 4378.]

Structure and conformation

The B and O atoms in trimethylboroxine form a symmetrical six-membered ring.

Trimethylboroxine Preparation Products And Raw materials

Raw materials

Preparation Products

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Trimethylboroxine Suppliers

SIGMA-RBI
Tel
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Fax
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Country
Switzerland
ProdList
6896
Advantage
91
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View Lastest Price from Trimethylboroxine manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
Trimethylboroxine 823-96-1
Price
US $30.00-10.00/KG
Min. Order
50KG
Purity
99%
Supply Ability
500000kg
Release date
2024-11-05
Hebei Yanxi Chemical Co., Ltd.
Product
Trimethylboroxine 823-96-1
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10 tons
Release date
2023-11-27
Hebei Fengjia New Material Co., Ltd
Product
Trimethylboroxine 823-96-1
Price
US $6.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
100000
Release date
2024-08-08

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