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| CAS No.: | 593-90-8 |
|---|---|
| Name: | TRIMETHYLBORON |
| Molecular Structure: | |
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| Formula: | C3H9 B |
| Molecular Weight: | 55.9155 |
| Synonyms: | Trimethylborane;Trimethylboron |
| EINECS: | 209-816-3 |
| Density: | 0.559 g/cm3 |
| Melting Point: | -161,5°C |
| Boiling Point: | 20 °C at 760 mmHg |
| Flash Point: | °C |
| Appearance: | colorless gas |
| Hazard Symbols: | F,C |
| Risk Codes: | 11-17-34 |
| Safety: | The gas ignites spontaneously in air or when mixed with chlorine. When heated to decomposition it emits acrid smoke and irritating fumes. See also BORANES and BORON COMPOUNDS. |
| PSA: | 0.00000 |
| LogP: | 1.37060 |

| Conditions | Yield |
|---|---|
| at 130.0°C, 74.1 Torr equilibrium; | A 99.6% B 99.6% |
| at 130.0°C, 74.1 Torr equilibrium; | A 99.6% B 99.6% |
| at 54.8°C, 57.6 Torr equilibrium; | A 90.8% B 90.8% |
| at 54.8°C, 57.6 Torr equilibrium; | A 90.8% B 90.8% |

Triisopropyl borate


methyllithium

B

trimethylborane

C

diisopropoxymethylborane

| Conditions | Yield |
|---|---|
| With hydrogenchloride In diethyl ether under N2; to cold (-78 °C) soln. of boron compd. in Et2O slowly added MeLi, stirred for 0.5 h, warmed to room temp., stirred for 0.5 h,Li(BMe4) detected by (11)B NMR, cooled to 0 °C, added soln. of HCl in Et2O, stirred for 15 min, warmed; not isolated, monitored by (11)B NMR; | A 1% B <1 C 98% |


tri-sec-butylborate


methyllithium

B

CH3B(OCH(CH3)CH2CH3)2

C

trimethylborane

| Conditions | Yield |
|---|---|
| With hydrogenchloride In diethyl ether under N2; to cold (-78 °C) soln. of boron compd. in Et2O slowly added MeLi, stirred for 0.5 h, warmed to room temp., stirred for 0.5 h,Li(BMe4) detected by (11)B NMR, cooled to 0 °C, added soln. of HCl in Et2O, stirred for 15 min, warmed; not isolated, monitored by (11)B NMR; | A 1% B 98% C <1 |


triisobutyl borate


methyllithium

B

CH3B(OCH2CH(CH3)2)2

C

trimethylborane

| Conditions | Yield |
|---|---|
| With hydrogenchloride In diethyl ether under N2; to cold (-78 °C) soln. of boron compd. in Et2O slowly added MeLi, stirred for 0.5 h, warmed to room temp., stirred for 0.5 h,Li(BMe4) detected by (11)B NMR, cooled to 0 °C, added soln. of HCl in Et2O, stirred for 15 min, warmed; not isolated, monitored by (11)B NMR; | A 1% B 98% C <1 |


methyllithium


2,4,4,5,5-pentamethyl-[1,3,2]dioxaborolane

A

(CH3)2BOC(CH3)2C(CH3)2OH

B

trimethylborane

| Conditions | Yield |
|---|---|
| With hydrogenchloride In diethyl ether byproducts: LiCl; 1 equiv of MeLi slowly adding to a soln. of the boronic ester at -78°C, stirring for 3 h at the same temp., 1 equiv of anhydrous HCl in Et2O adding, warming to room temp., stirring for 15 min; the content was detd. by (11)B NMR spectrum; | A 98% B <1 |


trimethyl-borane; compound with trimethylamine

A

trimethylborane

B

trimethylamine

| Conditions | Yield |
|---|---|
| at 111.3°C, 64.5 Torr equilibrium; | A 96% B 96% |
| at 111.3°C, 64.5 Torr equilibrium; | A 96% B 96% |
| at 65.8°C, 47.5 Torr equilibrium; | A 63.8% B 63.8% |

| Conditions | Yield |
|---|---|
| With hydrogenchloride In diethyl ether byproducts: LiCl, 2-propanol; 2 equiv of MeLi slowly adding to a soln. of the boronic ester at -78°C, stirring for 3 h at the same temp., 1 equiv of anhydrous HCl in Et2O adding, warming to room temp., stirring for 15 min; the content was detd. by (11)B NMR spectrum; | A 95% B <1 |
| With hydrogenchloride In diethyl ether byproducts: LiCl, 2-propanol; 1 equiv of MeLi slowly adding to a soln. of the boronic ester at -78°C, stirring for 3 h at the same temp., 1 equiv of anhydrous HCl in Et2O adding, warming to room temp., stirring for 15 min; the content was detd. by (11)B NMR spectrum; | A 95% B <1 |


methyllithium


2-methyl-[1,3,2]dioxaborinane

A

(CH3)2BO(CH2)3OH

B

trimethylborane

| Conditions | Yield |
|---|---|
| With hydrogenchloride In diethyl ether byproducts: LiCl; 2 equiv of MeLi slowly adding to a soln. of the boronic ester at -78°C, stirring for 3 h at the same temp., 1 equiv of anhydrous HCl in Et2O adding, warming to room temp., stirring for 15 min; the content was detd. by (11)B NMR spectrum; | A 92% B <7 |


bis[tert-butyl(dimethylboryl)amino]methylphosphanoxide

A

trimethylborane

B

1,3-di-tert-butyl-2,4-dimethyl-1,3,2,4-diazaphosphaboretidine-2-oxide

| Conditions | Yield |
|---|---|
| In neat (no solvent) heating at 160-170°C for 5 h in a stream of N2 with condensationof the volatiles in a trap cooled at -78°C;; distn.; elem. anal.;; | A 88% B 75% |

| Conditions | Yield |
|---|---|
| In diethyl ether at room temp. for 2 h, molar ratio BCl3:ether:MeMgBr01:2:3; by fractional condensation; | 87% |
| In diethyl ether at room temp. for 2 h, molar ratio BCl3:ether:MeMgBr01:2:3; by fractional condensation; | 87% |