CAS 823-96-1 Trimethylboroxine (HCID 574072)

Names & identifiers

Preferred name: Trimethylboroxine
IUPAC: 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane
English name: Trimethylboroxine
Molecular formula: C3H9B3O3
Molecular weight: 125.53

Names & synonyms

Trimethylboroxine823-96-1TrimethylboroxinDTXSID90341570RefChem:899827DTXCID10292651617-330-12,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinanetrimethyl-1,3,5,2,4,6-trioxatriborinane2,4,6-trimethylboroxineMFCD00013354Trimethylboroxine 50% w/w soln. in THF

Show more names

Trimethylcyclotriboroxane2,4,6-Trimethylboroxin2,4,6-TrMETHYLBOROXINtrimethylboroxin,TRIMEETHYLBOROXINEMethylboric anhydrideTrimethylcyclotriborane

C3H9B3O3Trimethylboroxin (50% Solution in THF)Boroxin, trimethyl-2,4,6-Trimethyl-1,3,5,2,4,6-trioxatriborinane; 2,4,6-Trimethylboroxine; Methaneboronic anhydrideMethaneboronic anhydridetrimethyboroxinetrimethyl boroxintrimethylboroxaine

Database identifiers

CAS: 823-96-1
PubChem CID: 574072
DTXSID: DTXSID90341570
EC Number: 617-330-1
Nikkaji: J375.125B

Properties

Computed structural properties

Topological polar surface area: 27.7 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 0
Heavy atoms: 9
Formal charge: 0
Complexity: 69.3

Physicochemical properties

Melting point: 38 °C · −38 °C(lit.)
Boiling point: 78 · 78-80 °C(lit.)
Density: 0.898 g/mL · 0.898 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.362(lit.)
Flash point: 16 °F · 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 · 1757008
InChI: 1S/C3H9B3O3/c1-4-7-5(2)9-6(3)8-4/h1-3H3
InChIKey: GBBSAMQTQCPOBF-UHFFFAOYSA-N
SMILES: Cb1ob(C)ob(C)o1
CAS DataBase Reference: 823 · 823-96-1(CAS DataBase Reference)
UNSPSC Code: 12352103 · 12352103
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS05,GHS07,GHS08
Signal word: Danger
Hazard statements: 225 · H225-H314-H335-H351
Precautionary statements: 201 · P201-P210-P233-P261-P280-P370+P378
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes: F,C,Xi
Risk Statements: 11 · 11-34-41-37/38-19
Safety Statements: 9 · 9-16-26-33-36/37/39-45-46-37/39-3
RIDADR: 2924 · UN 2924 3/PG 2
WGK Germany: 3 · 3
F: 2 · 2-10-21
TSCA: Yes
HazardClass: 3.1 · 3.1
PackingGroup: II
HS Code: 29319090 · 29319090
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 2 Skin · Flam. Liq. 2Skin Corr. 1B
Limited Quantities: 1 L · 1.0 L (0.3 gallon) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H225 (30.3%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P319, P321, P332+P317, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 152 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesFlam. Liq. 2 (30.3%)

Safety data

F: 2-10-21
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk: 3
tsca: Yes
ridadr: UN 2924 3/PG 2
hs_code: 29319090
risk_code: 11-34-41-37/38-19
Signal word: Danger
Symbol(GHS): GHS02,GHS05,GHS07,GHS08
hazard_code: F,C,Xi
safety_code: 9-16-26-33-36/37/39-45-46-37/39-3
hazard_class: 3.1
Storage Class: 3 - Flammable liquids
packing_group: II
Hazard statements: H225-H314-H335-H351
Limited Quantities: 1.0 L (0.3 gallon) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Hazard Classifications: Flam. Liq. 2Skin Corr. 1B
Precautionary statements: P201-P210-P233-P261-P280-P370+P378

Chemistry & industry

Applications · 3 items

UsesTrimethylboroxine (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.

UsesTrimethylboroxine 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.

UsesTrimethylboroxine (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 methods · 1 item

PreparationTrimethylboroxine 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℃.