Product Name

  • Name

    Trimethyl borate

  • EINECS 204-468-9
  • CAS No. 121-43-7
  • Article Data266
  • CAS DataBase
  • Density 0.932 g/mL at 20 °C(lit.)
  • Solubility decomposes in water
  • Melting Point -34 °C
  • Formula C3H9BO3
  • Boiling Point 67.5 °C at 760 mmHg
  • Molecular Weight 103.914
  • Flash Point -8 °C
  • Transport Information UN 2416 3/PG 2
  • Appearance water-white liquid
  • Safety 16-27-36/37/39-45-25-23-2
  • Risk Codes 11-21-23/25-36/37/38-10
  • Molecular Structure Molecular Structure of 121-43-7 (Trimethyl borate)
  • Hazard Symbols HarmfulXn,FlammableF
  • Synonyms NSC 777;Trimethoxyborane;Trimethoxyborine;Trimethoxyboron;Boricacid (H3BO3), trimethyl ester;Methylborate ((MeO)3B) (6CI);Borester O;Boric acid trimethyl ester;Borontrimethoxide;
  • PSA 27.69000
  • LogP -0.08950

Synthetic route

(borane)diphenylphosphinomethanethiol acetate
446822-71-5

(borane)diphenylphosphinomethanethiol acetate

methanol
67-56-1

methanol

A

Trimethyl borate
121-43-7

Trimethyl borate

B

thioacetic acid S-[(diphenylphosphanyl)methyl] ester
324753-11-9

thioacetic acid S-[(diphenylphosphanyl)methyl] ester

Conditions
ConditionsYield
In toluene at 100℃; Inert atmosphere;A n/a
B 100%
methanol
67-56-1

methanol

diphenyl(2-pyridyl)phosphane(P-B)borane(1:1)
1186392-98-2

diphenyl(2-pyridyl)phosphane(P-B)borane(1:1)

A

Trimethyl borate
121-43-7

Trimethyl borate

B

2-(diphenylphosphino)pyridine
37943-90-1

2-(diphenylphosphino)pyridine

Conditions
ConditionsYield
at 120℃; Inert atmosphere; Microwave irradiation;A n/a
B 100%
methanol
67-56-1

methanol

methylenebis(diphenylphosphane)-borane(1:2)
24442-15-7

methylenebis(diphenylphosphane)-borane(1:2)

A

Trimethyl borate
121-43-7

Trimethyl borate

B

bis-diphenylphosphinomethane
2071-20-7

bis-diphenylphosphinomethane

Conditions
ConditionsYield
In toluene at 100℃; Inert atmosphere;A n/a
B 100%
dimethoxyboryl trimethylsilyl ketene
155402-41-8

dimethoxyboryl trimethylsilyl ketene

A

methyl (trimethylsilyl)acetate
2916-76-9

methyl (trimethylsilyl)acetate

B

Trimethyl borate
121-43-7

Trimethyl borate

Conditions
ConditionsYield
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

zirconium(IV) borohydride

A

Trimethyl borate
121-43-7

Trimethyl borate

B

zirconium tetramethoxide

zirconium tetramethoxide

Conditions
ConditionsYield
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

methanol

triphenylphosphine borane
2049-55-0

triphenylphosphine borane

A

Trimethyl borate
121-43-7

Trimethyl borate

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
at 120℃; Inert atmosphere; Microwave irradiation;A n/a
B 99%
methanol
67-56-1

methanol

(propane-1,3-diyl)bis(diphenylphosphane)-borane(1:2)
100809-49-2

(propane-1,3-diyl)bis(diphenylphosphane)-borane(1:2)

A

Trimethyl borate
121-43-7

Trimethyl borate

B

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

Conditions
ConditionsYield
In toluene at 100℃; Inert atmosphere;A n/a
B 98%
carbon dioxide
124-38-9

carbon dioxide

dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

A

boron trioxide

boron trioxide

B

Trimethyl borate
121-43-7

Trimethyl borate

Conditions
ConditionsYield
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

methanol

C12H27BCl2O2Si

C12H27BCl2O2Si

A

Trimethyl borate
121-43-7

Trimethyl borate

B

6-(tert-butyldimethylsilyl)oxyhexan-1-ol
103202-59-1

6-(tert-butyldimethylsilyl)oxyhexan-1-ol

Conditions
ConditionsYield
methanolysis;A n/a
B 97%
methanol
67-56-1

methanol

(2-biphenyl)dicyclohexylphosphane-borane(1:1)
1186392-99-3

(2-biphenyl)dicyclohexylphosphane-borane(1:1)

A

Trimethyl borate
121-43-7

Trimethyl borate

B

CyJohnPhos
247940-06-3

CyJohnPhos

Conditions
ConditionsYield
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

1-aza-4,6,11-trioxa-5-boratricyclo[3.3.3.0(1,5)]undecane

phenyl trimethylsiloxane
2996-92-1

phenyl trimethylsiloxane

A

Trimethyl borate
121-43-7

Trimethyl borate

B

1-phenyl-2,8,9-trioxa-5-aza-1-silatricyclo<3.3.3.01.5>undecane(phenylsilatrane)

1-phenyl-2,8,9-trioxa-5-aza-1-silatricyclo<3.3.3.01.5>undecane(phenylsilatrane)

Conditions
ConditionsYield
With aluminum (III) chloride In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux;A n/a
B 97%
methanol
67-56-1

methanol

boric acid
11113-50-1

boric acid

Trimethyl borate
121-43-7

Trimethyl borate

Conditions
ConditionsYield
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

chlorodimethoxyborane

<β-Methyl-allyl>-triethyl-zinn
74348-94-0

<β-Methyl-allyl>-triethyl-zinn

A

Trimethyl borate
121-43-7

Trimethyl borate

B

methallyl-dimethoxyborane
54857-24-8

methallyl-dimethoxyborane

C

dimethallylmethoxyborane
74349-03-4

dimethallylmethoxyborane

D

chlorotriethylstannane
994-31-0

chlorotriethylstannane

Conditions
ConditionsYield
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

methanol

(1S,6R)-diethyl 5-oxo-3-oxabicyclo[4.1.0]heptane-7,7-dicarboxylate
1341221-68-8

(1S,6R)-diethyl 5-oxo-3-oxabicyclo[4.1.0]heptane-7,7-dicarboxylate

A

Trimethyl borate
121-43-7

Trimethyl borate

B

((1S,5S,6R)-5-hydroxy-3-oxabicyclo[4.1.0]heptane-7,7-diyl)dimethanol
1341221-72-4

((1S,5S,6R)-5-hydroxy-3-oxabicyclo[4.1.0]heptane-7,7-diyl)dimethanol

Conditions
ConditionsYield
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

methanol

lithium bis(1,2-dicarba-closo-dodecaborane-1,2-diselena)borate diethyl ether disolvate

lithium bis(1,2-dicarba-closo-dodecaborane-1,2-diselena)borate diethyl ether disolvate

A

1,2-dicarba-closo-dodecaborane(12)
16872-09-6

1,2-dicarba-closo-dodecaborane(12)

B

Trimethyl borate
121-43-7

Trimethyl borate

C

1,2-di(hydroseleno)-1,2-dicarba-closo-dodecaborane(12)
325820-04-0

1,2-di(hydroseleno)-1,2-dicarba-closo-dodecaborane(12)

Conditions
ConditionsYield
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

(chloromethyl)trimethoxysilane

1-aza-4,6,11-trioxa-5-boratricyclo[3.3.3.0(1,5)]undecane
15277-97-1

1-aza-4,6,11-trioxa-5-boratricyclo[3.3.3.0(1,5)]undecane

A

Trimethyl borate
121-43-7

Trimethyl borate

B

1-(chloromethyl)silatrane

1-(chloromethyl)silatrane

Conditions
ConditionsYield
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

(dibromoboryl)(trimethylsily)ketene

A

methyl (trimethylsilyl)acetate
2916-76-9

methyl (trimethylsilyl)acetate

B

Trimethyl borate
121-43-7

Trimethyl borate

Conditions
ConditionsYield
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

methanol

triethylsilane
617-86-7

triethylsilane

ethene
74-85-1

ethene

boron trichloride
10294-34-5

boron trichloride

A

Trimethyl borate
121-43-7

Trimethyl borate

B

ethylboronic acid dimethyl ester
7318-82-3

ethylboronic acid dimethyl ester

C

diethyl methoxy borane
7397-46-8

diethyl methoxy borane

Conditions
ConditionsYield
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

1,1'-bis(o-carborane)

A

Cs(1+)*{(C2B10H11)C2B9H11}(1-)=Cs{(C2B10H11)C2B9H11}

Cs(1+)*{(C2B10H11)C2B9H11}(1-)=Cs{(C2B10H11)C2B9H11}

B

Trimethyl borate
121-43-7

Trimethyl borate

Conditions
ConditionsYield
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

Methoxytrimethylsilane

benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

A

Trimethyl borate
121-43-7

Trimethyl borate

B

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

C

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
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

methanol

sodium metaborate

sodium metaborate

Trimethyl borate
121-43-7

Trimethyl borate

Conditions
ConditionsYield
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

lithium pentafluorophenyltrimethoxyborate

A

dimethyl pentafluorophenylboronate
848609-02-9

dimethyl pentafluorophenylboronate

B

Trimethyl borate
121-43-7

Trimethyl borate

Conditions
ConditionsYield
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

1-(dichloroboryl)pentaborane

A

pentaborane(9)

pentaborane(9)

B

1-(dimethoxyboryl)pentaborane

1-(dimethoxyboryl)pentaborane

C

Trimethyl borate
121-43-7

Trimethyl borate

D

(methoxy)dichloroborane
867-46-9

(methoxy)dichloroborane

E

chlorodimethoxyborane
868-81-5

chlorodimethoxyborane

Conditions
ConditionsYield
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

bis(dimethylamino)[tris(trimethylsilyl)silyl]borane

A

Trimethyl borate
121-43-7

Trimethyl borate

B

(dimethylamino)dimethoxy borane
7318-74-3

(dimethylamino)dimethoxy borane

C

tris(dimethylamino)borane
4375-83-1

tris(dimethylamino)borane

Conditions
ConditionsYield
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

methanol

Trimethyl borate
121-43-7

Trimethyl borate

Conditions
ConditionsYield
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

arachno-9-Et2S-6-SB9H11

tetramethlyammonium chloride
75-57-0

tetramethlyammonium chloride

A

(CH3)4N(1+)*SB8H11(1-)=(CH3)4N{SB8H11}

(CH3)4N(1+)*SB8H11(1-)=(CH3)4N{SB8H11}

B

Trimethyl borate
121-43-7

Trimethyl borate

Conditions
ConditionsYield
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

{bis(dimethylamino)boryl}ethoxyacetylene

A

{(dimethylamino)methoxyboryl}ethoxyacetylene
126686-31-5

{(dimethylamino)methoxyboryl}ethoxyacetylene

B

Trimethyl borate
121-43-7

Trimethyl borate

C

1-ethoxyacetylene
927-80-0

1-ethoxyacetylene

Conditions
ConditionsYield
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

arachno-9-Et3N-6-SB9H11

tetramethlyammonium chloride
75-57-0

tetramethlyammonium chloride

A

(CH3)4N(1+)*SB8H11(1-)=(CH3)4N{SB8H11}

(CH3)4N(1+)*SB8H11(1-)=(CH3)4N{SB8H11}

B

Trimethyl borate
121-43-7

Trimethyl borate

Conditions
ConditionsYield
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

1-I-B5H8

A

pentaborane(9)
19624-22-7

pentaborane(9)

B

2-methoxypentaborane(9)
23556-01-6

2-methoxypentaborane(9)

C

Trimethyl borate
121-43-7

Trimethyl borate

Conditions
ConditionsYield
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

bis{tris(trimethylsilyl)silyl} (dimethylamino)borane

Trimethyl borate
121-43-7

Trimethyl borate

Conditions
ConditionsYield
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

Trimethyl borate

C19H31BN2O4

C19H31BN2O4

Conditions
ConditionsYield
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

3-Bromothioanisole

Trimethyl borate
121-43-7

Trimethyl borate

3-methylthiophenylboronic acid
128312-11-8

3-methylthiophenylboronic acid

Conditions
ConditionsYield
With sodium hydroxide; iodine; magnesium In tetrahydrofuran100%
Trimethyl borate
121-43-7

Trimethyl borate

CH2CHC(O)(OCH2CH2)4OB(OC6H4)2

CH2CHC(O)(OCH2CH2)4OB(OC6H4)2

Conditions
ConditionsYield
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

Trimethyl borate

2,3-naphthalenediol
92-44-4

2,3-naphthalenediol

tetraethylene glycol monoacrylate
19812-60-3

tetraethylene glycol monoacrylate

CH2CHC(O)(OCH2CH2)4O(BO2C10H6)

CH2CHC(O)(OCH2CH2)4O(BO2C10H6)

Conditions
ConditionsYield
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

Trimethyl borate

benzene-1,2-diol
120-80-9

benzene-1,2-diol

tetraethylene glycol monoacrylate
19812-60-3

tetraethylene glycol monoacrylate

CH2CHC(O)(OCH2CH2)4OB(O2C6H4)

CH2CHC(O)(OCH2CH2)4OB(O2C6H4)

Conditions
ConditionsYield
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

2-bromo-9,10-di(2-naphthyl)anthracene

Trimethyl borate
121-43-7

Trimethyl borate

(9,10-di (naphthalene-2-yl) anthracene-2-yl)boronic acid
867044-28-8

(9,10-di (naphthalene-2-yl) anthracene-2-yl)boronic acid

Conditions
ConditionsYield
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

Trimethyl borate

1,1-dimethylethyl (7-bromo-1-methyl-2-oxo-1,2,3,4-tetrahydro-1,5-naphthyridin-3-yl)carbamate
1073633-62-1

1,1-dimethylethyl (7-bromo-1-methyl-2-oxo-1,2,3,4-tetrahydro-1,5-naphthyridin-3-yl)carbamate

[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

[7-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-methyl-6-oxo-5,6,7,8-tetrahydro-1,5-naphthyridin-3-yl]boronic acid

Conditions
ConditionsYield
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

2-bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene

Trimethyl borate
121-43-7

Trimethyl borate

(3-methyl-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}-2-naphthalenyl)boronic acid
872550-84-0

(3-methyl-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}-2-naphthalenyl)boronic acid

Conditions
ConditionsYield
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

4-bromo-2,5-dimethyl-4'-(trimethylsilyl)-1,1'-biphenyl

Trimethyl borate
121-43-7

Trimethyl borate

2,5-dimethyl-p-(4'-trimethylsilylphenyl)phenylboronic acid
1256293-81-8

2,5-dimethyl-p-(4'-trimethylsilylphenyl)phenylboronic acid

Conditions
ConditionsYield
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

Trimethyl borate

2,2-bis(hydroxymethyl)butanoic acid
10097-02-6

2,2-bis(hydroxymethyl)butanoic acid

C6H9BO4
1188369-89-2

C6H9BO4

Conditions
ConditionsYield
In methanol100%
Trimethyl borate
121-43-7

Trimethyl borate

3-iodo-4-methylfuran
107658-18-4

3-iodo-4-methylfuran

4-methylfuran-3-ylboronic acid
1358063-54-3

4-methylfuran-3-ylboronic acid

Conditions
ConditionsYield
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

Trimethyl borate

C8H9N3S
1599475-25-8

C8H9N3S

C8H10BN3O2S
1599475-26-9

C8H10BN3O2S

Conditions
ConditionsYield
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

Trimethyl borate

C8H7N3S
1599475-34-9

C8H7N3S

C8H8BN3O2S
1599475-35-0

C8H8BN3O2S

Conditions
ConditionsYield
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

Trimethyl borate

12-(4-bromophenyl)-N,N-dimethyldodecan-1-amine

12-(4-bromophenyl)-N,N-dimethyldodecan-1-amine

C20H36BNO2

C20H36BNO2

Conditions
ConditionsYield
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

Trimethyl borate

(15-(4-bromophenyl)pentadecyloxy)(tert-butyl)dimethylsilane

(15-(4-bromophenyl)pentadecyloxy)(tert-butyl)dimethylsilane

C27H51BO3Si

C27H51BO3Si

Conditions
ConditionsYield
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

1-bromo-2,3-dichloro-5-methoxybenzene

Trimethyl borate
121-43-7

Trimethyl borate

(2,3-dichloro-5-methoxyphenyl)boronic acid

(2,3-dichloro-5-methoxyphenyl)boronic acid

Conditions
ConditionsYield
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

Trimethyl borate

(SS)-ferrocenyl p-tolylsulfoxide
130225-27-3, 164297-25-0, 238753-24-7

(SS)-ferrocenyl p-tolylsulfoxide

(Sp,SS)-2-(p-tolylsulfinyl)ferrocenyl boronic acid

(Sp,SS)-2-(p-tolylsulfinyl)ferrocenyl boronic acid

Conditions
ConditionsYield
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

Trimethyl borate

(RS)-ferrocenyl p-tolylsulfoxide

(RS)-ferrocenyl p-tolylsulfoxide

(Rp,RS)-2-(p-tolylsulfinyl)ferrocenyl boronic acid

(Rp,RS)-2-(p-tolylsulfinyl)ferrocenyl boronic acid

Conditions
ConditionsYield
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

4-iodoisoxazole

Trimethyl borate
121-43-7

Trimethyl borate

(isoxazol-4-yl)boronic acid

(isoxazol-4-yl)boronic acid

Conditions
ConditionsYield
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

Trimethyl borate

3-bromo-10-mesityl-10H-phenothiazine

3-bromo-10-mesityl-10H-phenothiazine

(10-mesityl-10H-phenothiazin-3-yl)boronic acid

(10-mesityl-10H-phenothiazin-3-yl)boronic acid

Conditions
ConditionsYield
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

Trimethyl borate

2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridine
4984-62-7

2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridine

(2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-4-yl)boronic acid

(2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-4-yl)boronic acid

Conditions
ConditionsYield
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

Trimethyl borate

4-bromo-2-(tert-butoxycarbonylamino)-6-chlorobenzo[d]thiazole

4-bromo-2-(tert-butoxycarbonylamino)-6-chlorobenzo[d]thiazole

(2-((tert-butoxycarbonyl)amino)-6-chlorobenzo[d]thiazol-4-yl)boronic acid

(2-((tert-butoxycarbonyl)amino)-6-chlorobenzo[d]thiazol-4-yl)boronic acid

Conditions
ConditionsYield
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

Trimethyl borate

2.3-difluoroanisole
134364-69-5

2.3-difluoroanisole

(2,3-difluoro-4-methoxyphenyl)boronic acid

(2,3-difluoro-4-methoxyphenyl)boronic acid

Conditions
ConditionsYield
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

Trimethyl borate

water
7732-18-5

water

2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridine
4984-62-7

2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridine

(2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-4-yl)boronic acid

(2,6-bis(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-4-yl)boronic acid

Conditions
ConditionsYield
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

Trimethyl borate

C11H5BrFN

C11H5BrFN

C11H7BFNO2

C11H7BFNO2

Conditions
ConditionsYield
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

Trimethyl borate

C25H25BrClN

C25H25BrClN

water
7732-18-5

water

C25H27BClNO2

C25H27BClNO2

Conditions
ConditionsYield
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

Trimethyl borate

6-(2-bromo-3-(di([1,1′-biphenyl]-4-yl)amino)phenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine

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

dimethyl (2-(di([1,1′-biphenyl]-4-yl)amino)-6-((7-(diphenylamino)-9,9-dimethyl-9H-fluoren-3-yl)oxy)phenyl)boronate

Conditions
ConditionsYield
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%

Trimethyl borate Chemical Properties

IUPAC Name: Trimethyl borate
Molecular Formula: C3H9BO3
EINECS: 204-468-9
Molecular Weight: 103.912760 g/mol
Appearance: Colorless clear liquid
Melting Point: -34 °C
Boiling Point: 68-69 °C(lit.)
Flash Point: 8 °F
Density: 0.932 g/mL at 20 °C(lit.)
Vapor density: 3.59 (vs air)
Refractive index: n20/D 1.358(lit.)
Sensitive: Moisture
Solubility: Ether, methanol, tetrahydrofuran, isopropylamine, and hexane
Structure of Trimethyl borate (CAS NO.121-43-7):
               
Product Category of Trimethyl borate (CAS NO.121-43-7): Boron Compounds;Organometallics;Boric Acid Esters;Boric Acid Triesters

Trimethyl borate Uses

 Trimethyl borate (121-43-7) is primarily used as a precursor to boronic esters and boronic acids for Suzuki couplings.
Other uses include :
1.Anti-oxidant in Brazing and Solder Flux
2.Catalyst of olefin polymerisation
3.Wood preservative
4.raw material in the production of specialty glasses using sol-gel technology
5.raw material in the production of borophosphosilicate glass film by chemical vapor deposition
6.component of some flame retardants in textile industry
7.component of some welding fluxes
8.in green fire compositions for special effects (as a solution of boric acid in methanol, where it forms in small amounts)

Trimethyl borate Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 1290mg/kg (1290mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.
mouse LDLo intraperitoneal 1gm/kg (1000mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.
rabbit LD50 skin 1980uL/kg (1.98mL/kg)   American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.
rabbit LDLo intraperitoneal 1600mg/kg (1600mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.
rat LD50 oral 6140mg/kg (6140mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.
rat LDLo intraperitoneal 1600mg/kg (1600mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.

Trimethyl borate Safety Profile

Hazard Codes: HarmfulXn,FlammableF
Risk Statements: 11-21-23/25-36/37/38-10 
R10:Flammable. 
R11:Highly flammable. 
R21:Harmful in contact with skin. 
R23/25:Toxic by inhalation and if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 16-27-36/37/39-45-25-23-2
S16:Keep away from sources of ignition. 
S23:Do not breathe vapour. 
S25:Avoid contact with eyes. 
S27:Take off immediately all contaminated clothing. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

Trimethyl borate Specification

 Trimethyl borate , its cas register number is 121-43-7. It also can be called Boric acid trimethyl ester ; Methyl borate ; and Boron methoxide .

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