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Dimethylaminoborane
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Name

Dimethylaminoborane

 EINECS 200-823-7
CAS No. 74-94-2 Density 0.69 g/cm3
PSA 23.85000 LogP -0.95740
Solubility 125 g/L in water at 20°C Melting Point 36 °C(lit.)
Formula C2H10BN Boiling Point 59-65 °C
Molecular Weight 58.9191 Flash Point 65 °C
Transport Information UN 2926 4.1/PG 2 Appearance white crystalline powder with an amine odour
Safety 16-28-36/37-45-33-15 Risk Codes 11-24/25-36/37/38-20
Molecular Structure Molecular Structure of 74-94-2 (Dimethylaminoborane) Hazard Symbols FlammableF,ToxicT
Synonyms

Dimethylamine,compd. with BH3 (6CI);Dimethylamine, compd. with borane (1:1) (8CI);Methanamine, N-methyl-, compd. with borane (1:1);Borane, compd. withN-methylmethanamine (1:1);Borane, compd. with dimethylamine (1:1) (8CI);Methanamine, N-methyl-, boron complex;(Dimethylamine)trihydroboron;Dimethylamine compound with borane (1:1);Dimethylamine-borane;NSC 10218;Boron,trihydro(N-methylmethanamine)-, (T-4)-;

Article Data 42

Dimethylaminoborane Synthetic route

16940-66-2

sodium tetrahydroborate

dimethylammonium salt

dimethylammonium salt

74-94-2

dimethylamine borane

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 4h;93%
124-40-3

dimethyl amine

19287-45-7

diborane

74-94-2

dimethylamine borane

Conditions
ConditionsYield
In neat (no solvent) excess amine, 30-40°C, concn. of soln.;; distn. in vac. (60°C/2Torr) or recrystn. (petroleum ether);;91%
In neat (no solvent) excess amine, 30-40°C, concn. of soln.;; distn. in vac. (60°C/2Torr) or recrystn. (petroleum ether);;91%
In diethyl ether product in liquid form, crystn. on standing;; distn. in vac.;;961 %
In gas determination of react.-enthalpy;;
for 2h; Inert atmosphere; Gas phase; Cooling with ice;
16940-66-2

sodium tetrahydroborate

124-40-3

dimethyl amine

74-94-2

dimethylamine borane

Conditions
ConditionsYield
With iodine In 1,2-dimethoxyethane byproducts: NaI, H2; dropwise addn. of NaBH4 and I2 in DME to amine in DME, removal of solvent, addn. of C6H6, filtration, evapn. of filtrate in a N2 stream, drying in vac.;; recrystn. from CH2Cl2/hexane mixture;;84.4%
With potassium dihydrogenphosphate In water at -20 - 5℃; for 10h; Solvent; Reagent/catalyst; Autoclave; Large scale;84.5%
With boron trifluoride diethyl etherate In tetrahydrofuran refluxing, filtartion, evapn. of solvent;;
506-59-2

N,N-dimethylammonium chloride

74-94-2

dimethylamine borane

Conditions
ConditionsYield
With sodium tetrahydroborate In 1,2-dimethoxyethane at 20℃; Cooling with ice;71%
With lithium borohydride In diethyl ether at -78 - 20℃;

lithium borohydride

506-59-2

N,N-dimethylammonium chloride

74-94-2

dimethylamine borane

Conditions
ConditionsYield
In neat (no solvent) in vac., 3h;; distn. in vac. at 75-76°C/0.5Torr;;70%
In diethyl ether byproducts: H2, LiCl; room temp., 3h, filtration, evapn.;; recrystn. from C6H6/petroleum ether;;
In diethyl ether amine hydrochloride was added at -78°C to soln. LiBH4 in Et2O andstirred for 30 min, allowed to warm to room temp. and stirred for 5 h; react. mixt. was cooled to -45°C, slvent was removed in vacuo, residue was heated in vacuo at 65°C for sublimation;

potassium borohydride

506-59-2

N,N-dimethylammonium chloride

74-94-2

dimethylamine borane

Conditions
ConditionsYield
With sodium hydroxide In 1,2-dimethoxyethane; water at -5 - 15℃; for 6 - 10h; Conversion of starting material;55.1%
With sodium hydroxide In tetrahydrofuran; water at -10 - 15℃; for 10 - 14h; Conversion of starting material;54%

Me3N*BH2SPh

124-40-3

dimethyl amine

A

74-94-2

dimethylamine borane

B

1387442-05-8

Me2NH*BH2SPh

Conditions
ConditionsYield
at 20℃; for 36h;A 10%
B 46%
1838-13-7

dimethylamine borane

lithium borohydride

74-94-2

dimethylamine borane

Conditions
ConditionsYield
In tetrahydrofuran; water at 20℃; for 4h; Inert atmosphere;10%

calcium borohydride

124-40-3

dimethyl amine

74-94-2

dimethylamine borane

Conditions
ConditionsYield
In tetrahydrofuran

boron trioxide

1333-74-0

hydrogen

124-40-3

dimethyl amine

74-94-2

dimethylamine borane

Conditions
ConditionsYield
With aluminium trichloride; aluminium In neat (no solvent) High Pressure; heating the mixture under a H2-pressure of 800-900kg/cm**2 to 273°C for 10h; in mixture with other products;;

Dimethylaminoborane Consensus Reports

Reported in EPA TSCA Inventory.

Dimethylaminoborane Specification

The Dimethylaminoborane, with the CAS registry number 74-94-2, is also known as Dimethylamine compound with borane (1:1). It belongs to the product categories of Organometallics; B (Classes of Boron Compounds); Boranes; Reduction; Synthetic Organic Chemistry; Organoboron and borato-metal complexes. Its EINECS number is 200-823-7. This chemical's molecular formula is C2H10BN and molecular weight is 58.92. What's more, its systematic name is Trihydrido(N-methylmethanamine)boron. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Mutation data; (3)Skin / Eye Irritant. It should be sealed and stored in a cool and ventilated place. Moreover, it should be protected from oxides, heat and fire. It is sensitive to water and air. This chemical is used in reductivealkylation of protein.

Physical properties of Dimethylaminoborane are: (1)#H bond acceptors: 1; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 1; (4)Polar Surface Area: 4.44 Å2.

When you are using this chemical, please be cautious about it as the following:
This chemical is highly flammable, so you should keep it away from sources of ignition - No smoking. It is toxic in contact with skin and if swallowed and is harmful by inhalation. After contact with skin, you must wash immediately with plenty of ... (to be specified by the manufacturer). This substance is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing and gloves. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible). You need take precautionary measures against static discharges and keep this chemical away from heat.

You can still convert the following datas into molecular structure:
(1)SMILES: [BH3-][NH+](C)C
(2)Std. InChI: InChI=1S/C2H10BN/c1-4(2)3/h4H,1-3H3
(3)Std. InChIKey: RUOMFVPJBOADHA-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 55900ug/kg (55.9mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.
guinea pig LDLo oral 50mg/kg (50mg/kg)   National Technical Information Service. Vol. OTS0535833.
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   Journal of Pharmaceutical Sciences. Vol. 69, Pg. 1025, 1980.
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#05150.
mouse LDLo oral 50mg/kg (50mg/kg)   National Technical Information Service. Vol. OTS0535833.
rabbit LD50 intraperitoneal 35100ug/kg (35.1mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.
rabbit LD50 skin 210mg/kg (210mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES National Technical Information Service. Vol. OTS0535833.
rat LD50 intraperitoneal 39mg/kg (39mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.
rat LD50 oral 59mg/kg (59mg/kg)   American Industrial Hygiene Association Quarterly. Vol. 16, Pg. 280, 1955.

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