Product Name

  • Name

    Borane-2-picoline complex

  • EINECS 609-767-1
  • CAS No. 3999-38-0
  • Article Data14
  • CAS DataBase
  • Density 1.297 g/mL at 25 °C
  • Solubility Slightly sol. in water, cyclohexane, very sol. in methanol, THF, diglyme, and benzene
  • Melting Point 48 °C
  • Formula C6H10BN
  • Boiling Point
  • Molecular Weight 106.963
  • Flash Point 100°(212°F)
  • Transport Information
  • Appearance
  • Safety 36/37-43-26-36/37/38-14/15
  • Risk Codes 14/15-40-36/37/38-26
  • Molecular Structure Molecular Structure of 3999-38-0 (Borane-2-picoline complex)
  • Hazard Symbols F,Xn,Xi
  • Synonyms 2-Picoline,compd. with BH3 (1:1) (7Cl);2-Picoline, compd. with BH3 (6Cl);2-Picoline,compd. with borane (1:1) (8Cl);Pyridine, 2-methyl-, compd. with borane (1:1);Borane, compd. with 2-methylpyridine (1:1);Borane, compd. with 2-picoline(1:1) (8Cl);2-picoline borane;
  • PSA 3.88000
  • LogP -0.58900

Synthetic route

α-picoline
109-06-8

α-picoline

sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

2-picoline borane complex
3999-38-0

2-picoline borane complex

Conditions
ConditionsYield
With iodine In 1,2-dimethoxyethane byproducts: NaI, H2; addn. of stoichiometric amounts of I2 in DME to Na(BH4) (15-20% excess) and CH3C5H4N (7-10% excess), stirring for 3h, evapn., extn. with C6H6, evapn.;; dissolving in C6H6, pptn. with hexane;;94%
With I2 In 1,2-dimethoxyethane byproducts: NaI, H2; addn. of stoichiometric amounts of I2 in DME to Na(BH4) (15-20% excess) and CH3C5H4N (7-10% excess), stirring for 3h, evapn., extn. with C6H6, evapn.;; dissolving in C6H6, pptn. with hexane;;94%
With water; sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 4h;94%
α-picoline
109-06-8

α-picoline

diborane
19287-45-7

diborane

2-picoline borane complex
3999-38-0

2-picoline borane complex

Conditions
ConditionsYield
In pentane introduction of B2H6 (from Na(BH4) and (C2H5)2O*BF3 in diglyme) in the pentane-soln.; evapn. of solvent and excess of substituted pyridine;; recrystn.;;93.9%
In pentane introduction of B2H6 (from Na(BH4) and (C2H5)2O*BF3 in diglyme) in the pentane-soln.; evapn. of solvent and excess of substituted pyridine;; recrystn.;;93.9%
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.;
In nitrobenzene determination of react.-enthalpy at 25°C;;
In nitrobenzene determination of react.-enthalpy at 25°C;;
α-picoline
109-06-8

α-picoline

2-picoline borane complex
3999-38-0

2-picoline borane complex

Conditions
ConditionsYield
With sodium monobenzoxyborohydride In tetrahydrofuran at 40℃; for 5h; Inert atmosphere;93%
μ-(CH3)2N-B2H52*2-CH3-C5H4N

μ-(CH3)2N-B2H52*2-CH3-C5H4N

2-picoline borane complex
3999-38-0

2-picoline borane complex

Conditions
ConditionsYield
In neat (no solvent) 28.5°C, 20min;;83%
In neat (no solvent) 28.5°C, 20min;;83%
α-picoline
109-06-8

α-picoline

borane tetrahydrofuran

borane tetrahydrofuran

2-picoline borane complex
3999-38-0

2-picoline borane complex

Conditions
ConditionsYield
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);
α-picoline
109-06-8

α-picoline

2-picoline borane complex
3999-38-0

2-picoline borane complex

hydrotris(2-methylpyridine)boron(2+) diiodide
72541-44-7

hydrotris(2-methylpyridine)boron(2+) diiodide

Conditions
ConditionsYield
With iodine In benzene borane mixed with I2 in benzene at room temp., temp. raised to 60°C, additional I2 and benzene added, soln. refluxed for 8 h, to soln. 2-CH3C5H4N added, mixt. refluxed for 2 h; soln. cooled, solvent and excess 2-methylpyridine removed by filtration, solid washed with benzene;83.2%
2-picoline borane complex
3999-38-0

2-picoline borane complex

57272

57272

C29H33BCuF6N3

C29H33BCuF6N3

Conditions
ConditionsYield
at 25℃; for 1h; Glovebox;80%
2-picoline borane complex
3999-38-0

2-picoline borane complex

C24H13CuF10N2

C24H13CuF10N2

C23H17BCuF10N3

C23H17BCuF10N3

Conditions
ConditionsYield
at 25℃; for 1h; Glovebox;62%
ethyl diazoalaninate
6111-99-5

ethyl diazoalaninate

2-picoline borane complex
3999-38-0

2-picoline borane complex

ethyl 2-((2-methylpyridin-1-yl)boraneyl)propanoate

ethyl 2-((2-methylpyridin-1-yl)boraneyl)propanoate

Conditions
ConditionsYield
With cytochrome c from Rhodothermus marinus, V75R M100D M103T mutant In acetonitrile at 20℃; for 6h; pH=7.4; Catalytic behavior; Microbiological reaction; enantioselective reaction;42%
With D-glucose In acetonitrile at 20℃; for 24h; Catalytic behavior; Microbiological reaction; Sealed tube; enantioselective reaction;42%
2-picoline borane complex
3999-38-0

2-picoline borane complex

hydrogen cation

hydrogen cation

iodate
15454-31-6

iodate

A

2-methylpyridine conjugate acid
16969-46-3

2-methylpyridine conjugate acid

B

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
In water byproducts: I(1-);A >99
B n/a
In water byproducts: I(1-);A >99
B n/a
...Expand
2-picoline borane complex
3999-38-0

2-picoline borane complex

2-methylpyridine borane complex

2-methylpyridine borane complex

C6H9BN

C6H9BN

2-picoline borane complex
3999-38-0

2-picoline borane complex

2-methylpyridine borane complex

2-methylpyridine borane complex

Conditions
ConditionsYield
With 2-(2'-Chlorphenyl-4,5-diphenylimidazolyl-Radikal In tert-butylbenzene Kinetics; Reagent/catalyst;
2-picoline borane complex
3999-38-0

2-picoline borane complex

ethanol
64-17-5

ethanol

A

α-picoline
109-06-8

α-picoline

B

triethyl borate
150-46-9

triethyl borate

Conditions
ConditionsYield
With ReBr2(NO)(CH3CN)(PTA)2 at 50℃; for 4h; Kinetics; Reagent/catalyst; Temperature; Inert atmosphere;
...Expand
2-picoline borane complex
3999-38-0

2-picoline borane complex

hydrogen
1333-74-0

hydrogen

Conditions
ConditionsYield
With ethanol In ethanol byproducts: B(OC2H5)3, 2-methylpyridine; ethanolysis of 2-methylpyridine-borane at 50°C;
With ethanol; ReBr2(NO)(CH3CN)(PTA)2 In ethanol Kinetics; byproducts: B(OC2H5)3, 2-methylpyridine; ethanolysis of 2-methylpyridine-borane with 1 mol.-% ReBr2(NO)(MeCN)(1,3,5-triaza-7-phosphaadamantane)2 at room temp. or at 50°C;
2-picoline borane complex
3999-38-0

2-picoline borane complex

{[Cl2NN]Cu}(toluene)

{[Cl2NN]Cu}(toluene)

C23H23BCl4CuN3

C23H23BCl4CuN3

Conditions
ConditionsYield
In toluene at -35 - 25℃; for 1h; Inert atmosphere;0.135 g
In (2)H8-toluene at -80.16 - 79.84℃; for 1h; Kinetics; Inert atmosphere;
2-picoline borane complex
3999-38-0

2-picoline borane complex

N-(3-chloro-2-methylphenyl)-2-[(2S)-pyrrolidin-2-yl]-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide

N-(3-chloro-2-methylphenyl)-2-[(2S)-pyrrolidin-2-yl]-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide

N-(3-chloro-2-methylphenyl)-2-[(2S)-1-methylpyrrolidin-2-yl]-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide

N-(3-chloro-2-methylphenyl)-2-[(2S)-1-methylpyrrolidin-2-yl]-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide

Conditions
ConditionsYield
Stage #1: N-(3-chloro-2-methylphenyl)-2-[(2S)-pyrrolidin-2-yl]-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide With formaldehyd In methanol; water at 20℃;
Stage #2: 2-picoline borane complex In methanol; water for 3h;		11 mg
2-picoline borane complex
3999-38-0

2-picoline borane complex

C24H28B2N2Si

C24H28B2N2Si

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hexane; diethyl ether / 4 h / -70 - 20 °C / Inert atmosphere
2: diethyl ether / 40 h / -30 - 20 °C / Inert atmosphere
View Scheme
2-picoline borane complex
3999-38-0

2-picoline borane complex

C24H22N2Si

C24H22N2Si

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hexane; diethyl ether / 4 h / -70 - 20 °C / Inert atmosphere
2: diethyl ether / 40 h / -30 - 20 °C / Inert atmosphere
3: tert-butylamine / tetrahydrofuran / 15 h / 80 °C / Inert atmosphere; Sealed tube
View Scheme
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

2-picoline borane complex
3999-38-0

2-picoline borane complex

2-picolyl-N-borane

2-picolyl-N-borane

Conditions
ConditionsYield
In diethyl ether; hexane at -70 - 20℃; for 4h; Inert atmosphere;
2-picoline borane complex
3999-38-0

2-picoline borane complex

4-diazo-2-tosyl-1,4-dihydroisoquinolin-3(2H)-one

4-diazo-2-tosyl-1,4-dihydroisoquinolin-3(2H)-one

C22H23BN2O3S

C22H23BN2O3S

Conditions
ConditionsYield
With tetrakis(actonitrile)copper(I) hexafluorophosphate In 1,2-dichloro-ethane at 80℃; for 4h; Sealed tube;

Borane-2-picoline complex Specification

The Borane-2-picoline complex, with the CAS registry number 3999-38-0, has the systematic name of 2-methylpyridine - borane (1:1). It belongs to the following product categories: B (Classes of Boron Compounds); Boranes; Reduction; Synthetic Organic Chemistry. And the molecular formula of the chemical is C6H10BN.

The characteristics of Borane-2-picoline complex are as followings: (1)H-Bond Donor 0 ; (2)H-Bond Acceptor 1; (3)Rotatable Bond Count 0; (4)Exact Mass 107.09063; (5)MonoIsotopic Mass 107.09063; (6)Topological Polar Surface Area 12.9; (7)Heavy Atom Count 8; (8)Formal Charge 0; (9)Complexity 52.1; (10)Isotope Atom Count 0; (11)Defined Atom StereoCenter Count 0; (12)Undefined Atom StereoCenter Count 0; (13)Defined Bond StereoCenter Count 0; (14)Undefined Bond StereoCenter Count 0; (15)Covalently-Bonded Unit Count 2.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: B.N(CC)(CC)CC
(2)InChI: InChI=1/C6H15N.BH3/c1-4-7(5-2)6-3;/h4-6H2,1-3H3;1H3
(3)InChIKey: KDKNBGWKECQREO-UHFFFAOYAR

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