PRODUCTS

TRIMETHOXYBORON

Trimethoxyboron is the organoboron compound with the formula B(OCH3)3.
Trimethoxyboron is a colourless liquid that burns with a green flame.
Trimethoxyboron power to aid the preparation of sodium borohydride and act as a weak Lewis acid (AN = 23) is well respected among chemists worldwide.

CAS Number: 121-43-7
EC Number: 204-468-9
IUPAC Name: Trimethyl borate
Chemical Formula: C3H9BO3

Other names: (MeO)3B, 121-43-7, 1212-43-7, 197926-EP2269975A2, 197926-EP2269997A2, 197926-EP2275415A2, 27060-EP2281822A1, 27060-EP2292589A1, 27060-EP2308866A1, 27060-EP2314583A1, 32599-EP2270006A1, 32599-EP2272817A1, 32599-EP2284148A1, 32599-EP2295421A1, 32599-EP2298770A1, 32599-EP2298774A1, 32599-EP2301926A1, 32599-EP2301933A1, 32599-EP2305627A1, 32599-EP2311826A2, 32599-EP2311827A1, 3349-42-6, 4-01-00-01269 (Beilstein Handbook Reference), 46674-EP2292604A2, 46674-EP2308873A1, 46674-EP2311826A2, 63156-11-6, 82U64J6F5N, 95696-EP2371831A1, A804732, AI3-60245, AKOS000121036, AMY11113, AT28213, B(OCH3)3, B(OMe)3, B0226, B0522, Borate de trimthyle, Borester O, boric acid (H_3_BO_3_), trimethyl ester, Boric acid (H3BO3), trimethyl ester, Boric acid trimethyl, Boric acid trimethyl ester, Boric acid, trimethyl ester, BORON METHOXIDE, Borsaeuretrimethylester, BRN 1697939, C3-H9-B-O3, C3H9BO3, CHEBI:38913, DTXSID0037738, EC 204-468-9, EINECS 204-468-9, F0001-0343, FT-0600432, HSDB 5589, J-004497, LS-45040, Methyl borate, Methyl borate, ((MeO)3B), Methyl borate, (MeO)3 B, MFCD00008346, NA2416, NSC 777, NSC-777, NSC777, Q423710, SCHEMBL15840, STL264209, trimethoxy borane, trimethoxy boron, trimethoxyboran, Trimethoxyborane, Trimethoxyborine, Trimethoxyboron, trimethy borate, trimethyborate, TRIMETHYL BORATE, TRIMETHYL BORATE [HSDB], TRIMETHYL BORATE [MI], Trimethyl borate [UN2416] [Flammable liquid], Trimethyl borate [UN2416] [Flammable liquid], Trimethyl borate, >=98%, Trimethyl borate, 99.999% (trace metal basis), Trimethyl borate, azeotrope, 70%, in methanol, Trimethyl borate, purified by redistillation, >=99.5%, Trimethyl borate, purum, >=99.0% (GC), Trimethyl borate-11B, Trimethyl borate-11B, 99 atom % 11B, 98% (CP), trimethyl boric acid, trimethyl orthoborate, trimethyl-borate, Trimethylborat, trimethylborate, trimethylboric acid, Trimethylester kyseliny borite, Trimethylester kyseliny borite [Czech], UN 2416, UN2416, UNII-82U64J6F5N, Urea,N-(cyclohexylmethyl)-N'-cyclopentyl-, WLN: 1OBO1 & O1, 1212-43-7 [RN], 121-43-7 [RN], 1697939 [Beilstein], 204-468-9 [EINECS], 3349-42-6 [RN], 82U64J6F5N, Borate de triméthyle [French] [ACD/IUPAC Name], Boric acid (H3BO3), trimethyl ester [ACD/Index Name], BORIC ACID TRIMETHYL ESTER, ED5600000, METHYL BORATE, MFCD00008346 [MDL number], Trimethyl borate [ACD/IUPAC Name] [Wiki], TRIMETHYL BORATE-11B, 97 ATOM, Trimethylborat [German] [ACD/IUPAC Name], (MeO)3B, 31649-91-9 [RN], 4-01-00-01269 [Beilstein], 4-01-00-01269 (Beilstein Handbook Reference) [Beilstein], 486-73-7 [RN], 63156-11-6 [RN], B(OCH3)3, B(OMe)3, borato de trimetila [Portuguese], Borester O, boric acid, trimethyl ester, BORON METHOXIDE, Borsaeuretrimethylester, CHEBI:38913, EINECS 204-468-9, ST5409749, TL8000570, trimethoxyboramethane, trimethoxyborane, TRIMETHOXYBORINE, TRIMETHOXYBORON, Trimethyl borate [UN2416] [Flammable liquid], Trimethylborate, Trimethylester kyseliny borite [Czech], Trimethylester kyseliny borite [Czech], UN 2416, UNII:82U64J6F5N, UNII-82U64J6F5N, Urea,N-(cyclohexylmethyl)-N'-cyclopentyl-, WLN: 1OBO1 & O1

Trimethoxyboron is an intermediate in the preparation of sodium borohydride and is a popular reagent in organic chemistry.
Trimethoxyboron is a weak Lewis acid (AN = 23, Gutmann-Beckett method).

Borate esters are prepared by heating boric acid or related boron oxides with alcohols under conditions where water is removed.

Trimethoxyboron is the main precursor to sodium borohydride.
Trimethoxyboron is often used as a reagent in organic synthesis reactions, such as Suzuki couplings and Grignard reactions.

Trimethoxyboron is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.
Trimethoxyboron is used by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Molecular Weight: 103.92 g/mol
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 3
Exact Mass: 104.0644743 g/mol
Monoisotopic Mass: 104.0644743 g/mol

Topological Polar Surface Area: 27.7Å²
Heavy Atom Count: 7
Complexity: 31.7
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Trimethoxyboron is generally immediately available in most volumes.
Broad range of products for hydrogen storage research, advanced fuel cells and battery applications.

Hydrogen can easily be generated from renewable energy sources and is the most abundant element in the universe.
Hydrogen is produced from various sources such as fossil fuels, water and renewables.

Hydrogen is nonpolluting and forms water as a harmless byproduct during use.
The challenges associated with the use of hydrogen as a form of energy include developing safe, compact, reliable, and cost-effective hydrogen storage and delivery technologies.

Currently, hydrogen can be stored in these three forms: Compressed Hydrogen, Liquid Hydrogen and Chemical Storage.
High purity, submicron and nanopowder forms may be considered.

A member of the class of Borate Ester, Trimethoxyboron is a colorless liquid that ignites with an impressive green flame.
Trimethoxyboron power to aid the preparation of sodium borohydride and act as a weak Lewis acid (AN = 23) is well respected among chemists worldwide.
Borate ester, prepared by heating boron oxides and alcohols under dehydrating conditions, is a popular reagent in organic chemistry.

Trimethoxyboron reacts with a Grignard reagent or organolithium compounds to yield dimethyl boronates, which upon subsequent aqueous acid treatment afford corresponding boronic acids.
The resultant boronic acids or esters are useful intermediates in various cross-coupling reactions such as Suzuki coupling and Chan-Lam coupling.
Trimethoxyboron is also used in the preparation of sodium borohydride.

Trimethoxyboron is a useful reagent in organic synthesis.
Trimethoxyboron is involved in the production of resins, waxes and paints and acts as a methylation agent.

As a boron source, Trimethoxyboron is used to prepare flame retardants, anti-oxidants and corrosion inhibitors.
Trimethoxyboron reacts with Grignard reagents followed by hydrolysis to prepare boronic acid.

Trimethoxyboron is also used as a precursor of borate esters, which finds application in the Suzuki coupling reaction.
Trimethoxyboron is an intermediate in the preparation of sodium borohydride.

Applications of Trimethoxyboron:
Trimethoxyboron reacts with a Grignard reagent or organolithium compounds to yield dimethyl boronates, which upon subsequent aqueous acid treatment afford corresponding boronic acids.
The resultant boronic acids or esters are useful intermediates in various cross-coupling reactions such as Suzuki coupling and Chan-Lam coupling.
Trimethoxyboron is also used in the preparation of sodium borohydride.

Trimethoxyboron is the main precursor to sodium borohydride by Trimethoxyboron reaction with sodium hydride:
4 NaH + B(OCH3)3 → NaBH4 + 3 NaOCH3

Trimethoxyboron is a gaseous anti-oxidant in brazing and solder flux.
Otherwise, Trimethoxyboron has no announced commercial applications.
Trimethoxyboron has been explored as a fire retardant, as well as being examined as an additive to some polymers.

Organic synthesis:
Trimethoxyboron is a useful reagent in organic synthesis, as a precursor to boronic acids, which are used in Suzuki couplings.

These boronic acids are prepared via reaction of the Trimethoxyboron with Grignard reagents followed by hydrolysis:
ArMgBr + B(OCH3)3 → MgBrOCH3 + ArB(OCH3)2
ArB(OCH3)2 + 2 H2O → ArB(OH)2 + 2 HOCH3

Uses of Trimethoxyboron:
Trimethoxyboron is also an anti-oxidant in the brazing and solder flux and has been explored as a fire retardant.
Additionally, Trimethoxyboron has been examined as an additive to some polymers.

Trimethoxyboron is the main reactant in the Brown-Schlesinger method of producing sodium borohydride, and Trimethoxyboron is successfully recreated from sodium metaborate (NaBO2) via a sequential process that includes reacting with sulfuric acid, cooling crystallization, and reactive esterification distillation.

The metaborate is first transformed to boric acid (H3BO3) by treating Trimethoxyboron with sulfuric acid, obviating the need to synthesize borax (Na2B4O710H2O) in traditional techniques.
Boric acid is separated and purified from coexisting sodium sulphate by cooling crystallization (Na2SO4).

Following that, Trimethoxyboron is made by esterifying boric acid with methanol, with reactive esterification distillation used to speed up the process and purify Trimethoxyboron .
X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), and gas chromatography are used to demonstrate the formation of boric acid and Trimethoxyboron (GC).
Sodium metaborate could be converted to boric acid at a rate of about 55%, with a manufacturing yield of 74.1 to 96.5% for Trimethoxyboron esterified from boric acid as-produced.

Trimethoxyboronis potassium (sodium) boron hydrogen intermediate.
Vulcanizing agent, wood preservative, catalyst, gelling agent, heat stabilizer, hydrogen flame extinguishing agent, also used for flame retardant treatment of cotton and preparation of active silica, and as a gas chromatographic analysis reagent for carbohydrate derivatives.

Trimethoxyboron is used as a flame retardant, welding and brazing flux, chemical intermediate, fungicide, and a solvent for waxes, resins, and oils.
Trimethoxyboron is used as solvent for waxes, resins, oils; catalyst in manufacture of ketones; analysis of paint and varnish ingredients; as neutron detector gas in presence of a scintillation counter; as promoter of diborane reactions
Trimethoxyboron is intermediate in preparation of metal borohydrides.

Protection of Wood-based Materials:
Trimethoxyboron has a high vapour pressure injected into a container containing the wood beneath a vacuum during vapour phase treatments.
Trimethoxyboron then volatilizes and diffuses into the wood by combining with any moisture to form methanol and boric acid.

The borate is released during the reaction and is deposited in the wood.
Some methanol and borate remain in the wood when the vacuum is released.
This method has been used to cure a variety of composites, but Trimethoxyboron utility is limited because the wood being processed cannot be too wet (moisture content less than 6–8%).

Widespread uses by professional workers:
Trimethoxyboron is used in the following products: welding & soldering products and laboratory chemicals.
Trimethoxyboron is used in the following areas: building & construction work and scientific research and development.

Trimethoxyboron is used for the manufacture of: fabricated metal products.
Other release to the environment of Trimethoxyboron is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use as reactive substance.

Uses at industrial sites:
Trimethoxyboron is used in the following products: welding & soldering products, biocides (e.g. disinfectants, pest control products) and plant protection products.
Trimethoxyboron has an industrial use resulting in manufacture of another substance (use of intermediates).

Trimethoxyboron is used for the manufacture of: chemicals.
Release to the environment of Trimethoxyboron can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates) and as processing aid.

Industry Uses:
Intermediates

Industrial Processes with risk of exposure:
Welding
Brazing
Farming (Pesticides)

Properties of Trimethoxyboron:

Chemical Properties:
Dehydration produces Trimethoxyboron, which decomposes to methanol and boric acid when coming in contact with water.
In the presence of oxygen, Trimethoxyboron burns to generate boron trioxide.
Trimethoxyboron emits a vivid green hue in flames, which overpowers other flame colours.

Synthesis of Trimethoxyboron:
Trimethoxyboron is a boron triester with a single boron atom and three methoxide groups.
Trimethoxyboron can be made by mixing a large amount of dry methanol with boric acid, boron oxide, and a tiny amount of sulfuric acid, and heating the mixture to dehydrate Trimethoxyboron if necessary.

Due to the extra methanol used, the finished product would be an azeotropic mixture of methanol (25%) and Trimethoxyboron (75%).
Pure Trimethoxyboron can be obtained by converting methanol to Trimethoxyboron with a boron trihalide, such as boron tribromide.
However, the trihalide should be added gradually to avoid hydrolysis of the previously present boron tribromide.

Trimethoxyboron is an essential reagent in organic synthesis because Trimethoxyboron acts as a precursor to boronic acids.
These boronic acids, used in Suzuki couplings, are made by reacting Trimethoxyboron with Grignard reagents.

B(OCH3)3 + ArMgBr → MgBrOCH3 + ArB(OCH3)2

ArB(OCH3)2 + 2 H2O → ArB(OH)2 + 2 HOCH3

Methods of Manufacturing of Trimethoxyboron:
Trimethoxyboron is manufacture from pyridine-boron trichloride complex; from methanol and boric oxide, borax or boric acid; from methyl orthosilicates and boron halide; from boric acid and methanol.

Handling and Storage of Trimethoxyboron:

Advice on safe handling:
Work under hood.
Do not inhale substance/mixture.
Avoid generation of vapours/aerosols.

Advice on protection against fire and explosion:
Keep away from open flames, hot surfaces and sources of ignition.
Take precautionary measures against static discharge.

Hygiene measures of Trimethoxyboron:
Immediately change contaminated clothing.
Apply preventive skin protection.
Wash hands and face after working with substance.

Conditions for safe storage, including any incompatibilities:

Storage conditions:
Keep container tightly closed in a dry and well-ventilated place.
Keep away from heat and sources of ignition.
Keep locked up or in an area accessible only to qualified or authorized persons.

Storage class:
Storage class (TRGS 510): 3: Flammable liquids

Stability and Reactivity of Trimethoxyboron:

Reactivity:
Vapors may form explosive mixture with air.

Chemical stability:
Trimethoxyboron is chemically stable under standard ambient conditions (room temperature).

Possibility of hazardous reactions:

Exothermic reaction with:
Oxidizing agents
Acids
Fluorine
Water
Violent reactions possible with:
Alkali metals

Conditions to avoid:
Methanol is given off during processing and by reaction with water.
Avoid moisture.
Warming.

Incompatible materials:
Strong oxidizing agents

First Aid Measures of Trimethoxyboron:
Call 911 or emergency medical service.
Ensure that medical personnel are aware of Trimethoxyboron (s) involved and take precautions to protect themselves.

Move victim to fresh air if Trimethoxyboron can be done safely.
Give artificial respiration if victim is not breathing.

Administer oxygen if breathing is difficult.
Remove and isolate contaminated clothing and shoes.

In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes.
Wash skin with soap and water.

In case of burns, immediately cool affected skin for as long as possible with cold water.
Do not remove clothing if adhering to skin.

Keep victim calm and warm.
Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed.

General advice:
First aiders need to protect themselves.
Show Trimethoxyboron safety data sheet to the doctor in attendance.

After inhalation:
Fresh air.
Immediately call in physician.

If breathing stops:
Immediately apply artificial respiration, if necessary also oxygen.

In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.
Call a physician immediately.

After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.

If swallowed:
Give water to drink (two glasses at most).
Seek medical advice immediately.
In exceptional cases only, if medical care is not available within one hour, induce vomiting (only in persons who are wide awake and fully conscious), administer activated charcoal (20 - 40 g in a 10% slurry) and consult a doctor as quickly as possible.

Fire Fighting Measures:
The majority of these products have a very low flash point.
Use of water spray when fighting fire may be inefficient.

SMALL FIRE:
Dry chemical, CO2, water spray or alcohol-resistant foam.
Do not use dry chemical extinguishers to control fires involving nitromethane (UN1261) or nitroethane (UN2842).

LARGE FIRE:
Water spray, fog or alcohol-resistant foam.
Avoid aiming straight or solid streams directly onto Trimethoxyboron .
If Trimethoxyboron can be done safely, move undamaged containers away from the area around the fire.

FIRE INVOLVING TANKS OR CAR/TRAILER LOADS:
Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles.
Cool containers with flooding quantities of water until well after fire is out.

Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank.
ALWAYS stay away from tanks engulfed in fire.
For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn.

Suitable extinguishing media:
Carbon dioxide (CO2) Foam Dry powder

Unsuitable extinguishing media:
For Trimethoxyboron no limitations of extinguishing agents are given.

Special hazards arising from Trimethoxyboron or mixture:
Carbon oxides
Borane/boron oxides

Combustible.
Pay attention to flashback.
Vapors are heavier than air and may spread along floors.

Development of hazardous combustion gases or vapours possible in the event of fire.
Forms explosive mixtures with air at ambient temperatures.

Advice for firefighters:
Stay in danger area only with self-contained breathing apparatus.
Prevent skin contact by keeping a safe distance or by wearing suitable protective clothing.

Further information:
Remove container from danger zone and cool with water.
Prevent fire extinguishing water from contaminating surface water or the ground water system.

Fire Fighting Procedures:
To fight fire use dry chemical, CO2, spray, foam.

If material on fire or involved in fire:
Do not extinguish fire unless flow can be stopped.
Use water in flooding quantities as fog.

Solid stream of water may be ineffective.
Cool all affected containers with flooding quantities of water.

Use "alcohol" foam, dry chemical or carbon dioxide.
Keep run-off water out of sewers and water sources.

Accidental Release Measures of Trimethoxyboron:

Personal precautions, protective equipment and emergency procedures:

Advice for non-emergency personnel:
Do not breathe vapors, aerosols.
Avoid substance contact.

Ensure adequate ventilation.
Keep away from heat and sources of ignition.
Evacuate the danger area, observe emergency procedures, consult an expert.

Environmental precautions of Trimethoxyboron:
Do not let product enter drains.
Risk of explosion.

Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.

Observe possible material restrictions.
Take up carefully with liquid-absorbent material.

Dispose of properly.
Clean up affected area.