121-43-7

Basic information

• Product Name: Trimethyl borate
• Synonyms: METHYL BORATE;METHYL BORATE-11B;BORON TRIMETHOXIDE;BORIC ACID TRIMETHYL ESTER;BORON METHOXIDE;TRIMETHOXYBORANE;TRIMETHYL BORATE;TRIMETHYL BORATE-11B
• CAS NO: 121-43-7
• Molecular Formula: C₃H₉BO₃
• Molecular Weight: 103.91
• EINECS: 204-468-9
• Product Categories: Boron Compounds;Organometallics;B (Classes of Boron Compounds);Boric Acid Esters;Boric Acid Triesters;organic or inorganic borate;Boronic Acids and Derivatives;Chemical Synthesis;Organoborates;Organometallic Reagents
• Mol File: 121-43-7.mol
• Article Data: 266

Chemical Properties

• Melting Point: -34 °C
• Boiling Point: 68-69 °C(lit.)
• Flash Point: 8 °F
• Appearance: Colorless/Liquid
• Density: 0.932 g/mL at 20 °C(lit.)
• Vapor Density: 3.59 (vs air)
• Refractive Index: n20/D 1.358(lit.)
• Storage Temp.: Flammables area
• Solubility: Miscible with tetrahydrofuran, ether, isoporpylamine, hexane and
• Water Solubility: reacts
• Sensitive: Moisture Sensitive
• Stability: Stable. Incompatible with oxidizing agents. Decomposes slowly in the presence of moisture, rapidly in water. Flammable.
• Merck: 14,9712
• BRN: 1697939
• CAS DataBase Reference: Trimethyl borate(CAS DataBase Reference)
• NIST Chemistry Reference: Trimethyl borate(121-43-7)
• EPA Substance Registry System: Trimethyl borate(121-43-7)

Safety Data

• Hazard Codes: Xn,F,T
• Statements: 11-21-23/25-36/37/38-10-36-61-60
• Safety Statements: 16-27-36/37/39-45-25-23-2-26-53
• RIDADR: UN 2416 3/PG 2
• WGK Germany: 3
• RTECS: ED5600000
• F: 21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 121-43-7(Hazardous Substances Data)

Usage

Chemical Properties

Water-white moisture-sensitive liquid, fumes in the air. It forms an azeotrope with methanol with an azeotrope of 55°C. Miscible with ether, methanol, hexane, tetrahydrofuran; It is stable in anhydrous state and decomposes into methanol and boric acid in presence of water.

Uses

Trimethyl borate is a useful reagent in organic synthesis. It is involved in the production of resins, waxes and paints and acts as a methylation agent. As a boron source, it is used to prepare flame retardants, anti-oxidants and corrosion inhibitors. It reacts with Grignard reagents followed by hydrolysis to prepare boronic acid. It is also used as a precursor of borate esters, which finds application in the Suzuki coupling reaction. It is used as neutron detector gas in the presence of a scintillation counter; as a promoter of diborane reactions.

Application

Trimethyl borate 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. It is also used in the preparation of sodium borohydride.

Preparation

The preparation method of trimethyl borate1. The direct reaction between boric acid and methanol is as follows:3CH30H+H3B03→B (OCH3) 3+3H20Usually the trimethyl borate formed in the reaction forms an azeotrope with excess methanol and is distilled out together, and then the trimethyl borate is obtained by separating the azeotrope.2. The direct reaction between boron oxide and methanol is as follows:B203+6CH30H→2B (OCH3) 3+3H203. Borax, methanol and sulfuric acid are directly reacted, and the reaction formula is :Na2B4O7.1OH2O+12CH30H+2H2S04→4B (OCH3)3+2NaHS04+17H20

Definition

ChEBI: Trimethyl borate is a member of the class of borate esters obtained by the formal condensation of three equivalents of methanol with boric acid.

Reactions

Trimethyl borate B(OCH3)3 is a popular borate ester used in organic synthesis.borate esters are prepared from alkylation of trimethyl borate:ArMgBr + B(OCH3 )3 → MgBrOCH3 + ArB(OCH3 )2ArB(OCH3 )2 + 2H2O → ArB(OH)2 + 2 HOCH3

General Description

Trimethyl borate appears as a water-white liquid. Denser than water. Vapors heavier than air. Used as a solvent and fungicide for fruit.

Air & Water Reactions

Highly flammable. Rapidly decomposes in water.

Reactivity Profile

Borates, such as Trimethyl borate, behave similarly to esters in that they react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters/borates with alkali metals and hydrides.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Moderately toxic by ingestion, skin contact, and intraperitoneal routes. An eye irritant. A very dangerous fire hazard when exposed to heat, flame, or oxidizers. Moderately explosive when exposed to flame. Will react with water or steam to produce toxic and flammable vapors. To fight fire, use dry chemical, CO2, spray, foam. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS and BORON COMPOUNDS.

Purification Methods

Carefully fractionate the borate through a gauze-packed column. Re-distil and collect it in weighed glass vials and seal them. Keep it away from moisture. It undergoes alkyl exchange with alcohols and forms azeotropes, e.g. with MeOH the azeotrope consists of 70% (MeO)3B and 30% MeOH with b 52-54o/760mm, d 0.87. [Charnley et al. J Chem Soc 2288 1952, Gerrard & Lappert Chem Ind (London) 53 1952, Schlesinger et al. J Am Chem Soc 75 213 1953.] It has also been dried with Na and then distilled. [Beilstein 1 IV 1269.]

InChI:InChI:1S/C3H9BO3/c1-5-4(6-2)7-3/h1-3H3

Synthetic route

(borane)diphenylphosphinomethanethiol acetate (446822-71-5) + methanol (67-56-1) → Trimethyl borate (121-43-7) + thioacetic acid S-[(diphenylphosphanyl)methyl] ester (324753-11-9)

Conditions	Yield
In toluene at 100℃; Inert atmosphere;	A n/a B 100%

methanol (67-56-1) + diphenyl(2-pyridyl)phosphane(P-B)borane(1:1) (1186392-98-2) → Trimethyl borate (121-43-7) + 2-(diphenylphosphino)pyridine (37943-90-1)

Conditions	Yield
at 120℃; Inert atmosphere; Microwave irradiation;	A n/a B 100%

methanol (67-56-1) + methylenebis(diphenylphosphane)-borane(1:2) (24442-15-7) → Trimethyl borate (121-43-7) + bis-diphenylphosphinomethane (2071-20-7)

Conditions	Yield
In toluene at 100℃; Inert atmosphere;	A n/a B 100%

dimethoxyboryl trimethylsilyl ketene (155402-41-8) → methyl (trimethylsilyl)acetate (2916-76-9) + Trimethyl borate (121-43-7)

Conditions	Yield
With methanol In diethyl ether for 0.5h;	A 77% B 99%
With methanol In diethyl ether methanol in abs. ether added to a soln. of the ketene, warmed up, further methanol added, stirred for 30 min; distd.;	A 77% B 90%

zirconium(IV) borohydride → Trimethyl borate (121-43-7) + zirconium tetramethoxide

Conditions	Yield
With CH3OH In pentane byproducts: H2; (Ar (N2) or vac.); dropwise addn. of excess of MeOH to Zr-complex in pentane with stirring (60 min, room temp.), stirring (1 h), standing (12-17 h); volatiles and solvent distn. (vac.); elem. anal.;	A n/a B 99%

methanol (67-56-1) + triphenylphosphine borane (2049-55-0) → Trimethyl borate (121-43-7) + triphenylphosphine (603-35-0)

Conditions	Yield
at 120℃; Inert atmosphere; Microwave irradiation;	A n/a B 99%

methanol (67-56-1) + (propane-1,3-diyl)bis(diphenylphosphane)-borane(1:2) (100809-49-2) → Trimethyl borate (121-43-7) + 1,3-bis-(diphenylphosphino)propane (6737-42-4)

Conditions	Yield
In toluene at 100℃; Inert atmosphere;	A n/a B 98%

carbon dioxide (124-38-9) + dimethylsulfide borane complex (13292-87-0) → boron trioxide + Trimethyl borate (121-43-7)

Conditions	Yield
With 1,3,5-Tri-tert-butylbenzene; bis-(phosphoranyl)methanido aluminum hydride In benzene-d6 at 110℃; for 1h; Solvent; Schlenk technique;	A n/a B 97.6%

methanol (67-56-1) + C12H27BCl2O2Si → Trimethyl borate (121-43-7) + 6-(tert-butyldimethylsilyl)oxyhexan-1-ol (103202-59-1)

Conditions	Yield
methanolysis;	A n/a B 97%

methanol (67-56-1) + (2-biphenyl)dicyclohexylphosphane-borane(1:1) (1186392-99-3) → Trimethyl borate (121-43-7) + CyJohnPhos (247940-06-3)

Conditions	Yield
In toluene at 100℃; Inert atmosphere;	A n/a B 97%

1-aza-4,6,11-trioxa-5-boratricyclo[3.3.3.0(1,5)]undecane (15277-97-1) + phenyl trimethylsiloxane (2996-92-1) → Trimethyl borate (121-43-7) + 1-phenyl-2,8,9-trioxa-5-aza-1-silatricyclo<3.3.3.01.5>undecane(phenylsilatrane)

Conditions	Yield
With aluminum (III) chloride In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux;	A n/a B 97%

methanol (67-56-1) + boric acid (11113-50-1) → Trimethyl borate (121-43-7)

Conditions	Yield
In N,N-dimethyl-formamide at 129 - 130℃; under 750.075 Torr;	96%
In methanol byproducts: H2O; removal of product by azeotropic distn.;; separation of azeotrope by distn. through Raschig-rings (coated with H2SO4), purity of product:99.6%;;	96.5%
In methanol byproducts: H2O; removal of product by azeotropic distn.;; separation of azeotrope by treatment with LiCl (reuse of upper layer), purity of product:99.6%;;	96%

chlorodimethoxyborane (868-81-5) + <β-Methyl-allyl>-triethyl-zinn (74348-94-0) → Trimethyl borate (121-43-7) + methallyl-dimethoxyborane (54857-24-8) + dimethallylmethoxyborane (74349-03-4) + chlorotriethylstannane (994-31-0)

Conditions	Yield
In dichloromethane (N2); into soln. of B compd. was dropped soln. of Sn compd. within 20 min at -10°C; mixt. was sepd. by fractionated distn. in vac., yielding mixt. of B compds. and sepd. Et3SnCl;	A n/a B n/a C n/a D 92%

methanol (67-56-1) + (1S,6R)-diethyl 5-oxo-3-oxabicyclo[4.1.0]heptane-7,7-dicarboxylate (1341221-68-8) → Trimethyl borate (121-43-7) + ((1S,5S,6R)-5-hydroxy-3-oxabicyclo[4.1.0]heptane-7,7-diyl)dimethanol (1341221-72-4)

Conditions	Yield
Stage #1: (1S,6R)-diethyl 5-oxo-3-oxabicyclo[4.1.0]heptane-7,7-dicarboxylate With sodium tetrahydroborate In tetrahydrofuran at 20 - 60℃; for 6h; Inert atmosphere; Stage #2: methanol In tetrahydrofuran at 60℃; for 1.16667h; Inert atmosphere; Stage #3: With acetic acid In tetrahydrofuran; methanol at 0℃; Inert atmosphere;	A n/a B 84%

methanol (67-56-1) + lithium bis(1,2-dicarba-closo-dodecaborane-1,2-diselena)borate diethyl ether disolvate → 1,2-dicarba-closo-dodecaborane(12) (16872-09-6) + Trimethyl borate (121-43-7) + 1,2-di(hydroseleno)-1,2-dicarba-closo-dodecaborane(12) (325820-04-0)

Conditions	Yield
In dichloromethane-d2 air- and moisture excluded; soln. of carborane cooled to 0 °C, CH3OH added, stand for 2 h at 60 °C; monitored by (11)B, (13)C, (1)H NMR;	A 80% B n/a C 20%
In dichloromethane-d2 air- and moisture excluded; soln. of carborane cooled to 0 °C, CH3OH added, stand for 24 h at room temp.; monitored by (11)B NMR;	A 20% B n/a C 30%

(chloromethyl)trimethoxysilane (5926-26-1) + 1-aza-4,6,11-trioxa-5-boratricyclo[3.3.3.0(1,5)]undecane (15277-97-1) → Trimethyl borate (121-43-7) + 1-(chloromethyl)silatrane

Conditions	Yield
With aluminum (III) chloride In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux;	A n/a B 76%

(dibromoboryl)(trimethylsily)ketene (94363-48-1) → methyl (trimethylsilyl)acetate (2916-76-9) + Trimethyl borate (121-43-7)

Conditions	Yield
With methanol; triethylamine In diethyl ether byproducts: Et3N.HBr; argon atmosphere; methanol and triethylamine soln. addn. to B-compd. soln. cooled to -30°C (stirring); ppt. filtration off, washing (ether), fractionation; elem. anal.;	A 74% B 32%

methanol (67-56-1) + triethylsilane (617-86-7) + ethene (74-85-1) + boron trichloride (10294-34-5) → Trimethyl borate (121-43-7) + ethylboronic acid dimethyl ester (7318-82-3) + diethyl methoxy borane (7397-46-8)

Conditions	Yield
In methanol; xylene byproducts: Et3SiCl; Ar-atmosphere; mixing BCl3, Et3SiH and C2H4, distillation of EtBCl2, addn. of MeOH; collection (distillation); NMR spectroscopy;	A n/a B 72% C n/a
In methanol; dichloromethane byproducts: Et3SiCl, HCl; Ar-atmosphere; mixing BCl3 and Et3SiH at -78°C, bubling of C2H4, distillation of EtBCl2 and Et2BCl, addn. of MeOH at -78°C, warming to 0°C; collection (distillation); NMR spectroscopy;
In neat (no solvent) byproducts: Et3SiCl; Ar-atmosphere; mixing BCl3, Et3SiH and C2H4, addn. of MeOH; collection (distillation); NMR spectroscopy;

1,1'-bis(o-carborane) (12075-02-4) → Cs(1+)*{(C2B10H11)C2B9H11}(1-)=Cs{(C2B10H11)C2B9H11} + Trimethyl borate (121-43-7)

Conditions	Yield
With KOH,; caesium chloride In ethanol byproducts: H2; by 2.5 fold molar quant. KOH in boiling ethanolic soln., 1.5 h; recrystm. (water);	A 69% B n/a

Methoxytrimethylsilane (1825-61-2) + benzenediazonium tetrafluoroborate (369-57-3) → Trimethyl borate (121-43-7) + trimethylsilyl fluoride (420-56-4) + methoxybenzene (100-66-3)

Conditions	Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane 1.) 0 to 55 deg C very slowly, 2.) sonication, reflux, 16 h;	A 66% B n/a C 51%
In 1,1,2-Trichloro-1,2,2-trifluoroethane 1.) 0 to 55 deg C very slowly, 2.) sonication, reflux, 16 h; other alkyl(acyl)oxytrimethylsilanes;	A 66% B n/a C 51%

methanol (67-56-1) + sodium metaborate → Trimethyl borate (121-43-7)

Conditions	Yield
With carbon monoxide In methanol byproducts: H2O; generation of Na-formate by treatment of NaBO2 in methanol with CO at 100°C, distn. of the soln.;;	64.6%
In methanol

lithium pentafluorophenyltrimethoxyborate → dimethyl pentafluorophenylboronate (848609-02-9) + Trimethyl borate (121-43-7)

Conditions	Yield
In neat (no solvent) byproducts: C6F5H; under Ar, teflon-perfluoropropylene block copolymer vessel evacuated at 3E-2 hPa, 150-170 °C for 3 h; distn., yields were determined by (19)F and (11)B NMR;	A 2.5% B 56%

1-(dichloroboryl)pentaborane → pentaborane(9) + 1-(dimethoxyboryl)pentaborane + Trimethyl borate (121-43-7) + (methoxy)dichloroborane (867-46-9) + chlorodimethoxyborane (868-81-5)

Conditions

Yield

With methanol In dichloromethane Teflon-valve-equipped standard vacuum line or a nitrogen-filled glovebox; solvent, BCl2B5H8, CH3OH condensed into reactor, vessel warmed to room temp. over 4 h,; contents were fractionated, boron NMR data indicated presence of B(OMe)2B5H8 and BCl(OMe)B5H8 in the molar ratio 3:2;addn. of additional methanol, stirred for 5 min at -60 and -20 ° C, sepn., B(OMe)2B5H8 isolated;by-products:other boron compds.,;

A n/a B 46% C n/a D n/a E n/a

bis(dimethylamino)[tris(trimethylsilyl)silyl]borane (81175-91-9) → Trimethyl borate (121-43-7) + (dimethylamino)dimethoxy borane (7318-74-3) + tris(dimethylamino)borane (4375-83-1)

Conditions	Yield
With methanol In hexane (under Ar); the borane is dissolved in hexane and treated with MeOH, mixt. is heated to 45°C; monitored by (11)B-NMR;	A 44% B 8% C 6%

methanol (67-56-1) → Trimethyl borate (121-43-7)

Conditions	Yield
With aluminum oxide; sodium borate; carbon dioxide at 80℃; under 1034.32 Torr; for 4h;	43%
With sodium borate; molecular sieve; carbon dioxide at 80℃; under 1034.32 Torr; for 4h;	38%
With sodium borate; carbon dioxide at 80℃; under 1034.32 Torr; for 4h;	28%

arachno-9-Et2S-6-SB9H11 + tetramethlyammonium chloride (75-57-0) → (CH3)4N(1+)*SB8H11(1-)=(CH3)4N{SB8H11} + Trimethyl borate (121-43-7)

Conditions	Yield
With methanol; potassium hydroxide In methanol; water byproducts: C2H6; N2 atmosphere, refluxing (overnight), evapn. of solvent, dissolving (water), pptn. on addn. of aq. soln. of Me4NCl; recrystn. (acetonitrile/acetone), drying (vac.);	A 32.3% B n/a

{bis(dimethylamino)boryl}ethoxyacetylene (94318-00-0) → {(dimethylamino)methoxyboryl}ethoxyacetylene (126686-31-5) + Trimethyl borate (121-43-7) + 1-ethoxyacetylene (927-80-0)

Conditions	Yield
With methanol In neat (no solvent) Ar atmospher; addn. of MeOH to (Me2N)2BCCOEt (dropwise, water-cooling), heating (50-60°C, 1 h); fractionation (trap, solid carbon dioxide-cooling); NMR- and IR-spectroscopy;	A 32% B n/a C n/a

arachno-9-Et3N-6-SB9H11 + tetramethlyammonium chloride (75-57-0) → (CH3)4N(1+)*SB8H11(1-)=(CH3)4N{SB8H11} + Trimethyl borate (121-43-7)

Conditions	Yield
With methanol; potassium hydroxide In methanol; water byproducts: C2H6, H2; N2 atmosphere, refluxing (overnight), evapn. of volatiles, dissolving (water), pptn. on addn. of aq. soln. of Me4NCl; recrystn. (acetonitrile/acetone), drying (vac.);	A 30% B n/a

1-I-B5H8 (30624-33-0) → pentaborane(9) (19624-22-7) + 2-methoxypentaborane(9) (23556-01-6) + Trimethyl borate (121-43-7)

Conditions	Yield
With (CH3)2O In Dimethyl ether byproducts: CH3I, HB(OCH3)2, H2; at -12°C, 15h;;	A n/a B 25% C n/a

bis{tris(trimethylsilyl)silyl} (dimethylamino)borane (81175-92-0) → Trimethyl borate (121-43-7)

Conditions	Yield
With methanol In chloroform-d1 (under Ar); the borane is dissolved in CDCl3 and treated with MeOH, mixt. is heated to 80°C for 0,5 h; monitored by (11)B-NMR;	6%

Trimethyl borate (121-43-7) → C19H31BN2O4

Conditions	Yield
Stage #1: 1,1-dimethylethyl (2S)-4-[(3-bromophenyl)methyl]-2-methyl-1-piperazine carboxylate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 2h;	100%

3-Bromothioanisole + Trimethyl borate (121-43-7) → 3-methylthiophenylboronic acid (128312-11-8)

Conditions	Yield
With sodium hydroxide; iodine; magnesium In tetrahydrofuran	100%

Trimethyl borate (121-43-7) → CH2CHC(O)(OCH2CH2)4OB(OC6H4)2

Conditions	Yield
With 2,2'-biphenyldiol; tetraethylene glycol monoacrylate In acetonitrile soln. of B(OCH3)3 and 2,2'-biphenyldiol stirred at 60°C for 1 h; tetraethylene glycol monoacrylate added, stirred at 60°C for 1.5 h; cooled; solvent evapd.; residue dissolved (toluene); insolubles filtered; solvent removed by evapn.;	100%

Trimethyl borate (121-43-7) + 2,3-naphthalenediol (92-44-4) + tetraethylene glycol monoacrylate (19812-60-3) → CH2CHC(O)(OCH2CH2)4O(BO2C10H6)

Conditions	Yield
In acetonitrile naphthalene diol reacted with soln. of B(OCH3)3 at 60°C for 1 h; tetraethylene glycol monoacrylate added, stirred for 2 h; cooled; solvent evapd. at 40°C for 24 h;	100%

Trimethyl borate (121-43-7) + benzene-1,2-diol (120-80-9) + tetraethylene glycol monoacrylate (19812-60-3) → CH2CHC(O)(OCH2CH2)4OB(O2C6H4)

Conditions	Yield
In acetonitrile stirring of catechol and B(OMe)3 at 60 °C for 1h, addn of tetraethylene glycol monoacrylate, 2 h stirring; cooling, vac. evapn. at 40 °C for 24 h;	100%

2-bromo-9,10-di(2-naphthyl)anthracene (474688-76-1) + Trimethyl borate (121-43-7) → (9,10-di (naphthalene-2-yl) anthracene-2-yl)boronic acid (867044-28-8)

Conditions	Yield
Stage #1: 2-bromo-9,10-di(2-naphthyl)anthracene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 17h; Inert atmosphere;	100%
Stage #1: 2-bromo-9,10-di(2-naphthyl)anthracene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 1h; Stage #3: With hydrogenchloride; water In tetrahydrofuran	70%
Stage #1: 2-bromo-9,10-di(2-naphthyl)anthracene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 1h; Stage #3: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 3h;	70%
Stage #1: 2-bromo-9,10-di(2-naphthyl)anthracene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 1h; Stage #3: With hydrogenchloride; water In tetrahydrofuran for 3h;	70%
Stage #1: 2-bromo-9,10-di(2-naphthyl)anthracene With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Stage #3: With hydrogenchloride; water In tetrahydrofuran for 3h;

Trimethyl borate (121-43-7) + 1,1-dimethylethyl (7-bromo-1-methyl-2-oxo-1,2,3,4-tetrahydro-1,5-naphthyridin-3-yl)carbamate (1073633-62-1) → [7-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-methyl-6-oxo-5,6,7,8-tetrahydro-1,5-naphthyridin-3-yl]boronic acid (1073633-63-2)

Conditions	Yield
Stage #1: 1,1-dimethylethyl (7-bromo-1-methyl-2-oxo-1,2,3,4-tetrahydro-1,5-naphthyridin-3-yl)carbamate With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 3h;	100%

2-bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene (872548-85-1) + Trimethyl borate (121-43-7) → (3-methyl-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}-2-naphthalenyl)boronic acid (872550-84-0)

Conditions	Yield
Stage #1: 2-bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran; hexanes at -78 - 20℃; for 20.5h; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexanes	100%

4-bromo-2,5-dimethyl-4'-(trimethylsilyl)-1,1'-biphenyl (871114-85-1) + Trimethyl borate (121-43-7) → 2,5-dimethyl-p-(4'-trimethylsilylphenyl)phenylboronic acid (1256293-81-8)

Conditions	Yield
Stage #1: 4-bromo-2,5-dimethyl-4'-(trimethylsilyl)-1,1'-biphenyl; Trimethyl borate With n-butyllithium In tetrahydrofuran Stage #2: With hydrogenchloride In tetrahydrofuran; water	100%

Trimethyl borate (121-43-7) + 2,2-bis(hydroxymethyl)butanoic acid (10097-02-6) → C6H9BO4 (1188369-89-2)

Conditions	Yield
In methanol	100%

Trimethyl borate (121-43-7) + 3-iodo-4-methylfuran (107658-18-4) → 4-methylfuran-3-ylboronic acid (1358063-54-3)

Conditions	Yield
Stage #1: 3-iodo-4-methylfuran With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; pentane at -78 - 20℃; for 1h; Inert atmosphere; Stage #3: With hydrogenchloride; water In tetrahydrofuran; pentane for 0.75h; Inert atmosphere;	100%

Trimethyl borate (121-43-7) + C8H9N3S (1599475-25-8) → C8H10BN3O2S (1599475-26-9)

Conditions	Yield
Stage #1: C8H9N3S With n-butyllithium In tetrahydrofuran at -78℃; for 6h; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; Stage #3: With hydrogenchloride; water In tetrahydrofuran for 0.5h;	100%

Trimethyl borate (121-43-7) + C8H7N3S (1599475-34-9) → C8H8BN3O2S (1599475-35-0)

Conditions	Yield
Stage #1: C8H7N3S With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; Stage #3: With hydrogenchloride; water In tetrahydrofuran for 0.5h;	100%

Trimethyl borate (121-43-7) + 12-(4-bromophenyl)-N,N-dimethyldodecan-1-amine → C20H36BNO2

Conditions	Yield
Stage #1: 12-(4-bromophenyl)-N,N-dimethyldodecan-1-amine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 12h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 20℃; for 0.333333h; pH=9; Inert atmosphere;	100%

Trimethyl borate (121-43-7) + (15-(4-bromophenyl)pentadecyloxy)(tert-butyl)dimethylsilane → C27H51BO3Si

Conditions	Yield
Stage #1: (15-(4-bromophenyl)pentadecyloxy)(tert-butyl)dimethylsilane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 12h; Inert atmosphere;	100%

1-bromo-2,3-dichloro-5-methoxybenzene (174913-19-0) + Trimethyl borate (121-43-7) → (2,3-dichloro-5-methoxyphenyl)boronic acid

Conditions	Yield
Stage #1: 1-bromo-2,3-dichloro-5-methoxybenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; for 1h;	100%

Trimethyl borate (121-43-7) + (SS)-ferrocenyl p-tolylsulfoxide (130225-27-3, 164297-25-0, 238753-24-7) → (Sp,SS)-2-(p-tolylsulfinyl)ferrocenyl boronic acid

Conditions	Yield
Stage #1: (SS)-ferrocenyl p-tolylsulfoxide With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere;	100%

Trimethyl borate (121-43-7) + (RS)-ferrocenyl p-tolylsulfoxide → (Rp,RS)-2-(p-tolylsulfinyl)ferrocenyl boronic acid

Conditions	Yield
Stage #1: (RS)-ferrocenyl p-tolylsulfoxide With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere;	100%

4-iodoisoxazole (847490-69-1) + Trimethyl borate (121-43-7) → (isoxazol-4-yl)boronic acid

Conditions	Yield
Stage #1: 4-iodoisoxazole With TurboGrignard In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at 0℃; for 4.5h; Inert atmosphere;	100%

Trimethyl borate (121-43-7) + 3-bromo-10-mesityl-10H-phenothiazine → (10-mesityl-10H-phenothiazin-3-yl)boronic acid

Conditions	Yield
Stage #1: 3-bromo-10-mesityl-10H-phenothiazine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Schlenk technique; Stage #3: With hydrogenchloride	100%

Trimethyl borate (121-43-7) + 2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridine (4984-62-7) → (2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-4-yl)boronic acid

Conditions	Yield
Stage #1: 2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridine With n-butyllithium In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: Trimethyl borate In diethyl ether at 20℃; for 1h;	100%

Trimethyl borate (121-43-7) + 4-bromo-2-(tert-butoxycarbonylamino)-6-chlorobenzo[d]thiazole → (2-((tert-butoxycarbonyl)amino)-6-chlorobenzo[d]thiazol-4-yl)boronic acid

Conditions	Yield
Stage #1: 4-bromo-2-(tert-butoxycarbonylamino)-6-chlorobenzo[d]thiazole With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at -10 - 20℃; for 2h; Stage #2: Trimethyl borate at -78℃; for 0.5h;	100%

Trimethyl borate (121-43-7) + 2.3-difluoroanisole (134364-69-5) → (2,3-difluoro-4-methoxyphenyl)boronic acid

Conditions	Yield
Stage #1: 2.3-difluoroanisole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane for 2h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at -30℃; for 2h; Inert atmosphere;	100%
Stage #1: 2.3-difluoroanisole With n-butyllithium In tetrahydrofuran; hexane at -85 - -75℃; for 2h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -85 - -75℃;

Trimethyl borate (121-43-7) + water (7732-18-5) + 2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridine (4984-62-7) → (2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-4-yl)boronic acid

Conditions	Yield
Stage #1: 2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridine With n-butyllithium In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: Trimethyl borate In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; Stage #3: water With hydrogenchloride at 0℃; for 0.166667h;	100%

Trimethyl borate (121-43-7) + C11H5BrFN → C11H7BFNO2

Conditions	Yield
Stage #1: C11H5BrFN With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at 20℃; for 16h;	100%

Trimethyl borate (121-43-7) + C25H25BrClN + water (7732-18-5) → C25H27BClNO2

Conditions	Yield
Stage #1: C25H25BrClN With n-butyllithium In tetrahydrofuran; hexane at -65℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -65 - 20℃; Inert atmosphere; Stage #3: water With hydrogenchloride In tetrahydrofuran; hexane at 0℃;	100%

Trimethyl borate (121-43-7) + 6-(2-bromo-3-(di([1,1′-biphenyl]-4-yl)amino)phenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine → dimethyl (2-(di([1,1′-biphenyl]-4-yl)amino)-6-((7-(diphenylamino)-9,9-dimethyl-9H-fluoren-3-yl)oxy)phenyl)boronate

Conditions	Yield
Stage #1: 6-(2-bromo-3-(di([1,1′-biphenyl]-4-yl)amino)phenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at 20℃; for 2h;	100%
Stage #1: 6-(2-bromo-3-(di([1,1′-biphenyl]-4-yl)amino)phenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere;	100%

Upstream product

• 681-84-5 Tetramethyl orthosilicate 

Downstream Products

• 330793-45-8 (4-PHENYLAMINOCARBONYLPHENYL)BORONIC ACID 
• 28177-48-2 2,6-Difluorophenol 
• 756520-78-2 2-(Methanesulfonylamino)phenylboronic acid 
• 129112-21-6 2-(N,N-DIETHYLAMINOCARBONYL)PHENYLBORONIC ACID 
• 355386-94-6 Quinoline-5-boronic acid 
• 126726-62-3 Isopropenylboronic acid pinacol ester 
• 481681-02-1 4-FLUORO-3-(HYDROXYMETHYL)BENZENEBORONIC ACID 
• 761446-44-0 1-Methyl-4-pyrazole boronic acid pinacol ester 
• 98437-23-1 2-Benzothienylboronic acid 
• 98546-51-1 4-(Methylthio)phenylboronic acid 
• 98437-24-2 Benzofuran-2-boronic acid 
• 32316-92-0 2-Naphthaleneboronic acid 
• 126747-14-6 4-Cyanophenylboronic acid 
• 163105-90-6 2-Methoxypyridine-3-boronic acid 
• 183158-34-1 2,3-Dimethylphenylboronic acid 
• 123324-71-0 4-tert-Butylphenylboronic acid 
• 132898-95-4 2,2'-BITHIOPHENE-5-BORONIC ACID 
• 146631-00-7 4-Benzyloxybenzeneboronic acid 
• 847818-74-0 1-Methyl-1H-pyrazole-5-boronic acid pinacol ester 
• 135145-90-3 2,5-Dichlorophenylboronic acid 
• 94839-07-3 3,4-METHYLENEDIOXYPHENYLBORONIC ACID 
• 86-58-8 8-Quinolineboronic acid 
• 99627-05-1 3,4,5-Trifluorophenol 
• 143-66-8 Sodium tetraphenylboron 
• 4463-42-7 Benzylboronic acid 
• 99768-12-4 Methyl 4-boronobenzoate 
• 51067-38-0 4-PHENOXYPHENYLBORONIC ACID 
• 4612-26-4 1,4-Phenylenebisboronic acid 
• 192182-55-1 1-METHYL-1H-INDOLE-5-BORONIC ACID 2,2-DIMETHYL PROPANE DIOL-1,3-CYCLIC ESTER 
• 142273-84-5 3-Methoxymethylphenylboronic acid 
• 16114-47-9 3,5-Dimethylisoxazole-4-boronic acid 
• 16152-51-5 4-Isopropylbenzeneboronic acid 
• 190661-29-1 2-Benzyloxyphenylboronic acid 
• 1193-03-9 2-FLUOROPHENYLBORONIC ACID 
• 138008-97-6 2-ISOPROPOXYPHENYLBORONIC ACID 
• 144104-59-6 5-Indolylboronic acid 
• 1993-03-9 2-Fluorophenylboronic acid 
• 5122-95-2 Biphenyl-3-boronic acid 

Recommend Products

• 121-43-7  Trimethyl borate 
• 67-56-1  methanol 
• 5419-55-6  Triisopropyl borate 
• 688-74-4  boric acid tributyl ester 
• 867-46-9  (methoxy)dichloroborane 
• 5565-36-6  1,4-bis-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzene 
• 106-37-6  1.4-dibromobenzene 
• 126-30-7  2,2-Dimethyl-1,3-propanediol 
• 17936-83-3  bis(dimethoxyboryl)phenylmethane 
• 98-87-3  benzylidene dichloride 
• 14559-88-7  2,2-dimethylethenylboronic acid 
• 38614-36-7  2-methylpropen-1-ylmagnesium bromide 
• 6867-35-2  lithium tetramethanolatoborate 
• 865-34-9  lithium methanolate 

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Thermodynamic modeling of decomposition processes of Trimethyl borate (cas 121-43-7) in different gas mixtures09/04/2019

A thermodynamic modeling on the chemical vapor deposition in the B-C-O-H, B-C-O-H-He and B-C-O-H-N systems was performed. The thermodynamic equilibrium in these systems was calculated by minimization of Gibbs free energy for the conditions: 300 ≤ Tdep, K ≤ 2000; 0.001 ≤ Ptotal, Torr ≤ 760; m...detailed