• Name

  BORANE-N,N-DIETHYLANILINE COMPLEX

• EINECS 236-305-2
• CAS No. 13289-97-9
• Article Data9
• CAS DataBase
• Density 0.92 g/cm³
• Solubility may decompose in water
• Melting Point -30--27 °C(lit.)
• Formula C₁₀H₁₅N^.BH₃
• Boiling Point 213.5 °C at 760 mmHg
• Molecular Weight 163.071
• Flash Point 97.8 °C
• Transport Information UN 3398 4.3/PG 2
• Appearance clear colorless to amber liquid
• Safety 16-33-36/37/39-43-9
• Risk Codes 10-14
• Molecular Structure
• Hazard Symbols R10:;
• Synonyms Aniline,N,N-diethyl-, compd. with BH3 (7CI);Aniline, N,N-diethyl-, compd. with borane(1:1) (8CI);Borane, compd. with N,N-diethylaniline (1:1);(N,N-Diethylaniline)trihydroboron;Borane-N,N-diethylaniline;Diethylphenylamine-borane;N,N-Diethylaniline-borane;NSC 239123;
• PSA 3.24000
• LogP 1.34890

Synthetic route

tetra-amminezinc tetrahydroborate

5882-45-1

N,N-diethylaniline hydrochloride

13289-97-9

N,N-diethylaniline borane complex

Conditions

Conditions	Yield
In pyridine byproducts: NH3, H2, C5H5N*BH3; addn. of a warm soln. (70°C) of hydrochloride in C5H5N to BH4-salt in C5H5N, warming to 50-55°C; distn. in vac.;; product-mixture of (C2H5)2(C6H5)N*BH3 and C5H5N*BH3; removal of C5H5N*BH3 at 65°C/1Torr;;
In pyridine byproducts: NH3, H2, C5H5N*BH3; addn. of a warm soln. (70°C) of hydrochloride in C5H5N to BH4-salt in C5H5N, warming to 50-55°C; distn. in vac.;; product-mixture of (C2H5)2(C6H5)N*BH3 and C5H5N*BH3; removal of C5H5N*BH3 at 65°C/1Torr;;

91-66-7

N,N-diethylaniline

19287-45-7

diborane

13289-97-9

N,N-diethylaniline borane complex

Conditions

Conditions	Yield
In neat (no solvent) addn. of diborane to amine at liquid N2 temp., keeping at -111°C, -78°C and 0°C consecutively, stirring at 0°C for 4-6 h (vacuum line); cooling to -78°C, removal of B2H6 by distn.;
at 20℃; for 12h; Inert atmosphere; Glovebox;

16940-66-2

sodium tetrahydroborate

91-66-7

N,N-diethylaniline

13289-97-9

N,N-diethylaniline borane complex

Conditions

Conditions	Yield
In diethylene glycol byproducts: H2; N2; I2 in diglyme introduced at room temp. to generator flask contg. NaBH4 in diglyme; generated H2 and B2H6 bubbled through soln. of PhNEt2 in toluene or benzene of side tube at 0°C; excess B2H6 drifven off with stream of N2;

borane tetrahydrofuran

91-66-7

N,N-diethylaniline

13289-97-9

N,N-diethylaniline borane complex

Conditions

Conditions	Yield
In tetrahydrofuran addn. of borane soln. to amine soln. at 0°C during 1 h, stirring for 1 h (N2); evapn. (vac.), drying (vac., overnight);
In tetrahydrofuran dropwise addn. of 2.0M BH3*THF to a THF soln. of the amine (10 mmol); performed under a dry N2 atm.;; removal of solvent and excess of BH3*THF under reduced pressure immediately after addn.;;	>99

22348-32-9, 63401-04-7, 112022-88-5, 112068-01-6

(S)-diphenylprolinol

5882-45-1

N,N-diethylaniline hydrochloride

A

13289-97-9

N,N-diethylaniline borane complex

B

(S)-Corey-Bakshi-Shibata oxazaborolidine

Conditions

Conditions	Yield
Stage #1: N,N-diethylaniline hydrochloride With sodium tetrahydroborate In 1,2-dimethoxyethane; dichloromethane; water at 20 - 30℃; for 6h; Inert atmosphere; Large scale reaction; Stage #2: (S)-diphenylprolinol In 1,2-dimethoxyethane; dichloromethane at 25 - 30℃; for 1h; Inert atmosphere;

...Expand

14044-65-6

borane-THF

91-66-7

N,N-diethylaniline

13289-97-9

N,N-diethylaniline borane complex

Conditions

Conditions	Yield
In neat (no solvent) for 12h; Inert atmosphere; Glovebox; Cooling with ice;

688-73-3

tri-n-butyl-tin hydride

10294-34-5

boron trichloride

91-66-7

N,N-diethylaniline

13289-97-9

N,N-diethylaniline borane complex

Conditions

Conditions	Yield
In neat (no solvent) for 12h; Temperature; Inert atmosphere; Glovebox;

...Expand

13289-97-9

N,N-diethylaniline borane complex

7664-41-7

ammonia

A

10043-11-5

ammonia borane complex

B

91-66-7

N,N-diethylaniline

Conditions

Conditions	Yield
In neat (no solvent) at 0℃; under 750.075 Torr; for 3h; Inert atmosphere; Glovebox;	A 95% B n/a
In toluene Product distribution / selectivity;

...Expand

13289-97-9

N,N-diethylaniline borane complex

7664-41-7

ammonia

A

10043-11-5

ammonia borane complex

B

(bisammine)dihydroborium(+1) tetrahydroborate(1-)

C

91-66-7

N,N-diethylaniline

Conditions

Conditions	Yield
In toluene Product distribution / selectivity;
Product distribution / selectivity;

...Expand

13289-97-9

N,N-diethylaniline borane complex

942617-40-5

1-(1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropyl)-ethanone

942618-15-7

(R)-1-(1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropyl)-ethanol

Conditions

Conditions	Yield
With (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 25℃; for 1.16667h;

13289-97-9

N,N-diethylaniline borane complex

7732-18-5

water

1333-74-0

hydrogen

Conditions

Conditions	Yield
In water; ethylene glycol quantitative hydrolysis in a 1:1-mixture at 25°C within 3h;;
In water
In water
In water; ethylene glycol

13289-97-9

N,N-diethylaniline borane complex

111-66-0

oct-1-ene

3248-78-0

trioctylborane

Conditions

Conditions	Yield
byproducts: N,N-diethyl aniline; 25°C, 2h;;	>99

67-56-1

methanol

13289-97-9

N,N-diethylaniline borane complex

1333-74-0

hydrogen

Conditions

Conditions	Yield
In water byproducts: 11;
In water

13289-97-9

N,N-diethylaniline borane complex

2049-55-0

triphenylphosphine borane

Conditions

Conditions	Yield
With triphenylphosphine In not given treating complex with PPh3; almost quantitative yiild of product;	>99

13289-97-9

N,N-diethylaniline borane complex

121589-95-5

2-(2'-methylaminoethoxy)-o-phenylene-1,3,2-dioxaborolane

DEANB/5 mol% SpiroCAT formulation

Conditions

Conditions	Yield
at 45℃; for 3h; Inert atmosphere;

N,N-Diethylanilineborane Specification