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13292-87-0

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13292-87-0 Usage

Uses

Different sources of media describe the Uses of 13292-87-0 differently. You can refer to the following data:
1. Borane-dimethyl sulfide complex is used for hydroborations and reductions. Used with a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones. CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketones to 1,3-diols. Highly enantioselective reduction of ketones catalyzed by C3-symmetric tripodal hydroxyamides.
2. Borane-dimethyl sulfide (BH3 Me2S) can be used as a reagent: For the selective synthesis of 1,3,5-oxygenated compounds from dimethyl 3-oxoglutarate. For the conversion of ozonides to alcohols. In the CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketones to 1,3-diols. For enantioselective reduction of ketones to chiral secondary alcohols in the presence of C3-symmetric tripodal hydroxyamide as a ligand. For the hydroboration reduction and other applications. With a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones.

General Description

Borane dimethyl sulfide complex (BMS) acts as a highly efficient and selective reducing agent in the presence of catalytic sodium tetrahydroborate for α-hydroxy esters. Asymmetric borane reduction of a variety of prochiral ketones with BMS using spiroborate esters as catalyst has been reported.

Check Digit Verification of cas no

The CAS Registry Mumber 13292-87-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,2,9 and 2 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 13292-87:
(7*1)+(6*3)+(5*2)+(4*9)+(3*2)+(2*8)+(1*7)=100
100 % 10 = 0
So 13292-87-0 is a valid CAS Registry Number.
InChI:InChI=1/C2H6S.BH3/c1-3-2;/h1-2H3;1H3

13292-87-0 Well-known Company Product Price

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  • TCI America

  • (D1843)  Dimethyl Sulfide Borane  >90.0%(T)

  • 13292-87-0

  • 25mL

  • 490.00CNY

  • Detail
  • TCI America

  • (D1843)  Dimethyl Sulfide Borane  >90.0%(T)

  • 13292-87-0

  • 100mL

  • 1,250.00CNY

  • Detail
  • Alfa Aesar

  • (42965)  Borane-dimethyl sulfide complex, 2M in THF, packaged under Argon in resealable ChemSeal? bottles   

  • 13292-87-0

  • 100ml

  • 536.0CNY

  • Detail
  • Alfa Aesar

  • (42965)  Borane-dimethyl sulfide complex, 2M in THF, packaged under Argon in resealable ChemSeal? bottles   

  • 13292-87-0

  • 500ml

  • 2310.0CNY

  • Detail
  • Alfa Aesar

  • (42963)  Borane-dimethyl sulfide complex, 2M in toluene, packaged under Argon in resealable ChemSeal? bottles   

  • 13292-87-0

  • 100ml

  • 1436.0CNY

  • Detail
  • Alfa Aesar

  • (42963)  Borane-dimethyl sulfide complex, 2M in toluene, packaged under Argon in resealable ChemSeal? bottles   

  • 13292-87-0

  • 500ml

  • 5941.0CNY

  • Detail
  • Alfa Aesar

  • (L07705)  Borane-dimethyl sulfide complex, 94%   

  • 13292-87-0

  • 25ml

  • 529.0CNY

  • Detail
  • Alfa Aesar

  • (L07705)  Borane-dimethyl sulfide complex, 94%   

  • 13292-87-0

  • 100ml

  • 1519.0CNY

  • Detail
  • Alfa Aesar

  • (43327)  Borane-dimethyl sulfide complex, nominally 5M in ether, packaged under Argon in resealable ChemSeal? bottles   

  • 13292-87-0

  • 50ml

  • 801.0CNY

  • Detail
  • Alfa Aesar

  • (43327)  Borane-dimethyl sulfide complex, nominally 5M in ether, packaged under Argon in resealable ChemSeal? bottles   

  • 13292-87-0

  • 250ml

  • 2748.0CNY

  • Detail
  • Alfa Aesar

  • (42967)  Borane-dimethyl sulfide complex, packaged under Argon in resealable ChemSeal? bottles   

  • 13292-87-0

  • 5ml

  • 198.0CNY

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  • Alfa Aesar

  • (42967)  Borane-dimethyl sulfide complex, packaged under Argon in resealable ChemSeal? bottles   

  • 13292-87-0

  • 25ml

  • 495.0CNY

  • Detail

13292-87-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Borane-methyl sulfide complex

1.2 Other means of identification

Product number -
Other names Borane - Dimethyl Sulfide Complex

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13292-87-0 SDS

13292-87-0Synthetic route

A

dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

B

dichloroborane-dimethyl sulfide

dichloroborane-dimethyl sulfide

Conditions
ConditionsYield
In not given equimolar mixt. of products not sepd., detd. by (11)B-NMR spectroscopy;
lithium borohydride

lithium borohydride

C8H14BBrS(CH3)2
70160-59-7

C8H14BBrS(CH3)2

A

dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

B

9-bora-bicyclo[3.3.1]nonane
280-64-8

9-bora-bicyclo[3.3.1]nonane

Conditions
ConditionsYield
In tetrahydrofuran byproducts: LiBr; 0°C, 0.25 h; detected by 11B NMR;
boron dimethyl-trifluoro sulphide
353-43-5

boron dimethyl-trifluoro sulphide

hydrogen
1333-74-0

hydrogen

dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

Conditions
ConditionsYield
With 1,2,2,6,6-pentamethylpiperidine In toluene at 75℃; under 15001.5 Torr; for 4h; Autoclave;> 90 %Spectr.
boron dimethyl-trifluoro sulphide
353-43-5

boron dimethyl-trifluoro sulphide

boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

hydrogen
1333-74-0

hydrogen

dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

Conditions
ConditionsYield
With 1,2,2,6,6-pentamethylpiperidine In toluene at 100℃; under 15001.5 Torr; for 2h; Autoclave;60 %Spectr.
dimethylsulfide
75-18-3

dimethylsulfide

diborane
19287-45-7

diborane

dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

Conditions
ConditionsYield
at 0 - 5℃; for 1.25h; Inert atmosphere;
boron tribromide dimethyl sulfide complex
29957-59-3

boron tribromide dimethyl sulfide complex

dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

dibromoborane dimethylsulfide
55671-55-1

dibromoborane dimethylsulfide

Conditions
ConditionsYield
In benzene at 80℃; for 18h; Inert atmosphere; Glovebox;100%
In not given molar ratio BH3SMe2:BBr3SMe2 1:2; followed by NMR;
dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

2'-hydroxy-2-diphenylphosphinobiphenyl
155566-51-1

2'-hydroxy-2-diphenylphosphinobiphenyl

(2'-hydroxy-biphenyl-2-yl)-diphenylphosphane borane
917477-90-8

(2'-hydroxy-biphenyl-2-yl)-diphenylphosphane borane

Conditions
ConditionsYield
In tetrahydrofuran; dichloromethane (N2); addn. of soln. of borane complex in THF to soln. of phosphine deriv. in CH2Cl2 at room temp., stirring for 24 h; evapn., NMR;100%
formaldehyd
50-00-0

formaldehyd

Diethylphosphine
627-49-6

Diethylphosphine

dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

(borane)diethylphosphinomethane alcohol
635689-45-1

(borane)diethylphosphinomethane alcohol

Conditions
ConditionsYield
Stage #1: Diethylphosphine; dimethylsulfide borane complex In tetrahydrofuran for 2h;
Stage #2: formaldehyd With potassium hydroxide In tetrahydrofuran; water for 4h;
100%
dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

1-(dipropylphosphanylmethyl-propyl-phosphanyl)-propane
686353-30-0

1-(dipropylphosphanylmethyl-propyl-phosphanyl)-propane

C13H36B2P2
1422260-95-4

C13H36B2P2

Conditions
ConditionsYield
In diethyl ether for 2h; Inert atmosphere; Schlenk technique;100%
dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

[Ir(fac-bis[(2-diphenylphosphino)phenyl]phosphide)(COD)]
1420831-79-3

[Ir(fac-bis[(2-diphenylphosphino)phenyl]phosphide)(COD)]

[Ir(fac-bis[(2-diphenylphosphino)phenyl]phosphide)(BH3)(COD)]

[Ir(fac-bis[(2-diphenylphosphino)phenyl]phosphide)(BH3)(COD)]

Conditions
ConditionsYield
In toluene at 20℃; Inert atmosphere; Schlenk technique;100%
dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

N-benzhydryl-1,1-diphenylphosphinoamine
1425274-89-0

N-benzhydryl-1,1-diphenylphosphinoamine

C25H25BNP
1446469-42-6

C25H25BNP

Conditions
ConditionsYield
In toluene at 20℃; for 12h; Schlenk technique; Inert atmosphere; Glovebox;100%
dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

4-(dihexylamino)pyridine
95758-21-7

4-(dihexylamino)pyridine

4-dihexylaminopyridine borane

4-dihexylaminopyridine borane

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 0℃; for 0.166667h; Schlenk technique;100%
dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

C26H24OP2

C26H24OP2

C26H30B2OP2

C26H30B2OP2

Conditions
ConditionsYield
In tetrahydrofuran; toluene for 16h; Schlenk technique; Inert atmosphere;100%
dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

C44H36Fe2OP2

C44H36Fe2OP2

C44H42B2Fe2OP2

C44H42B2Fe2OP2

Conditions
ConditionsYield
In tetrahydrofuran for 16h; Schlenk technique; Inert atmosphere;100%
dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

C19H32ClGeN

C19H32ClGeN

C19H35BClGeN

C19H35BClGeN

Conditions
ConditionsYield
In tetrahydrofuran; benzene at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;100%
dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

4-methoxy-phenol
150-76-5

4-methoxy-phenol

tris(4-methoxiphenyloxy)borane
42080-75-1

tris(4-methoxiphenyloxy)borane

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 60℃; for 23h; Inert atmosphere; Schlenk technique;99.1%
dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

(1S,2R)-(+)-ephedrine
321-98-2

(1S,2R)-(+)-ephedrine

(2RP,4SC,5RC)-(+)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine borane

(2RP,4SC,5RC)-(+)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine borane

Conditions
ConditionsYield
In tetrahydrofuran N2-atmosphere; addn. of 1.3 equiv. of borane to ligand, stirring (room temp., overnight); solvent removal (vac.), chromy. (SiO2, Et2O/pentane=1:1);99%
(2R,5S)-2,3-diphenyl-1,3-diazaphosphabicyclo[3.3.0]octane

(2R,5S)-2,3-diphenyl-1,3-diazaphosphabicyclo[3.3.0]octane

dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

(2R,5S)-2-phenyl-3-oxa-1-azaphosphabicyclo[3.3.0]octane-borane complex

(2R,5S)-2-phenyl-3-oxa-1-azaphosphabicyclo[3.3.0]octane-borane complex

Conditions
ConditionsYield
In tetrahydrofuran N2-atmosphere; addn. of 1.3 equiv. of borane to ligand, stirring (room temp., overnight); solvent removal (vac.), chromy. (SiO2, Et2O/pentane=1:1);99%
(2R,5S)-2,-phenyl-3-o-anisyl-1,3-diazaphosphabicyclo[3.3.0]octane

(2R,5S)-2,-phenyl-3-o-anisyl-1,3-diazaphosphabicyclo[3.3.0]octane

dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

(2R,5S)-2-(2-methoxyphenyl)-3-oxa-1-aza-2-phosphabicyclo[3.3.0]octane(P-B)borane

(2R,5S)-2-(2-methoxyphenyl)-3-oxa-1-aza-2-phosphabicyclo[3.3.0]octane(P-B)borane

Conditions
ConditionsYield
In tetrahydrofuran N2-atmosphere; addn. of 1.3 equiv. of borane to ligand, stirring (room temp., overnight); solvent removal (vac.), chromy. (SiO2, Et2O/pentane=1:1);99%
dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

(NCN)0.5Si(NCN)CH(CH3)B(C2H4Si(NCN)0.5NCN)

(NCN)0.5Si(NCN)CH(CH3)B(C2H4Si(NCN)0.5NCN)

Conditions
ConditionsYield
With Si(CHCH2)(NCN)0.5 In toluene byproducts: SMe2; Ar-atmosphere; dropwise addn. of borane to Si-compd. at 0°C, slowwarming to room temp., stirring (room temp., 2 h); solvent removal (vac.), drying (70°C, 1E-3 mbar, 24 h); elem. anal.;99%
HSi(CHCH2)NCN

HSi(CHCH2)NCN

dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

HSi(NCN)CH(CH3)B(C2H4SiHNCN)

HSi(NCN)CH(CH3)B(C2H4SiHNCN)

Conditions
ConditionsYield
In toluene byproducts: SMe2; Ar-atmosphere; dropwise addn. of borane to Si-compd. at 0°C, slowwarming to room temp., stirring (room temp., 2 h); solvent removal (vac.), drying (70°C, 1E-3 mbar, 24 h); elem. anal.;99%
CH3Si(CHCH2)NCN

CH3Si(CHCH2)NCN

dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

CH3Si(NCN)CH(CH3)B(C2H4Si(CH3)NCN)

CH3Si(NCN)CH(CH3)B(C2H4Si(CH3)NCN)

Conditions
ConditionsYield
In toluene byproducts: SMe2; Ar-atmosphere; dropwise addn. of borane to Si-compd. at 0°C, slowwarming to room temp., stirring (room temp., 2 h); solvent removal (vac.), drying (70°C, 1E-3 mbar, 24 h); elem. anal.;99%
dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

(s)-N-methylvalinol
78617-54-6

(s)-N-methylvalinol

(2R,4S)-3-methyl-4-isopropyl-2-phenyl-1,3,2-oxazaphospholidine-borane complex

(2R,4S)-3-methyl-4-isopropyl-2-phenyl-1,3,2-oxazaphospholidine-borane complex

Conditions
ConditionsYield
In tetrahydrofuran N2-atmosphere; addn. of 1.3 equiv. of borane to ligand, stirring (room temp., overnight); solvent removal (vac.), chromy. (SiO2, Et2O/pentane=1:1);99%

13292-87-0Related news

Reductive cleavage of permethylated polysaccharides with Borane-methyl sulfide complex (cas 13292-87-0) and butyltin trichloride07/17/2019

Several per-O-methylated monosaccharides and polysaccharides were used as models in an attempt to identify more convenient reagents for accomplishing reductive cleavage of glycosidic linkages. Included in the model studies were methyl α- and β-d-glucopyranoside, methyl α- and β-d-mannopyrano...detailed

13292-87-0Relevant articles and documents

Coyle, T. D.,Kaesz, H. D.,Stone, F. G. A.

, p. 2989 - 2994 (1959)

Reactions of pentaborane(11) with ethers

Kodama, Goji,Saturnino, Dennis J.

, p. 2243 - 2249 (1975)

Reactions of pentaborane(11) (B5H11) with ethers were studied at low temperatures by means of 11B NMR spectroscopy. The reactions of B5H11 with dimethyl and diethyl thioethers give the symmetrical cleavage products R2S·BH3 and R2S·B4H8. Species that are produced in the reaction system of B5H11 and oxoethers are very dependent upon the base strength of the ether. Strongly basic tetrahydrofuran can effect the unsymmetrical cleavage of B5H11 to produce H2B(THF)2+B4H9 -. Evidence for the formation of this cleavage product is based on the NMR spectral evidence and on the observed reaction products produced in the reaction of HCl with the B5H11-THF system. A second species is observable in the THF-B5H11 system which is more predominant at higher temperatures. This species is assigned as the simple adduct B5H11·THF. Moderately basic ethers like dimethyl and diethyl ethers produce only one observable species which is considered to be B5H11·OR2. Weakly basic diisopropyl ether does not react with B5H11. No direct evidence for the symmetrical cleavage of B5H11 by oxoethers has been observed. The similarities and differences between these reactions and analogous B4H10 reactions are discussed.

Coordination Chemistry of Borane in Solution: Application to a STING Agonist

Lemaire, Sébastien,Zhdanko, Alexander,van der Worp, Boris A.

, (2022/04/09)

Equilibrium constants were determined for ligand exchange reactions of borane complexes with various oxygen, sulfur, nitrogen, and phosphorus nucleophiles in solution, and a binding affinity scale was built spanning a range of 12 orders of magnitude. While the Keq are minimally dependent on the solvent, the rate of ligand exchange varies significantly. The fastest and slowest rates were observed in THF and CDCl3, respectively. Moreover, the ligand exchange rate differs in a very broad range depending on stability of the starting complex. Binding of BH3 was found to be much more sensitive to steric factors than protonation. Comparing nitrogen bases having equal steric properties, a linear correlation of BH3 binding affinity vs. Br?nsted acidity was found. This correlation can be used to quickly estimate the BH3 binding affinity of a substrate if pKa is known. Kinetic studies suggest the ligand exchange to occur as a bimolecular SN2 reaction unless other nucleophilic species were present in the reaction mixture.

Stabilizer-containing borane reagent combination solution, and preparation method and use thereof

-

Paragraph 0035-0036, (2018/06/04)

The invention provides a stabilizer-containing borane reagent combination solution. The borane reagent combination solution comprises a borane-dimethyl sulfide complex, tetrahydrofuran and a stabilizer, wherein the concentration of the borane-dimethyl sulfide complex in tetrahydrofuran is 1-10 mol/L, and a molar ratio of the borane-dimethyl sulfide complex to the stabilizer is 100:1 to 1000:1. Thecombination solution has the advantages of high concentration, good thermal stability, realization of high-efficiency utilization of a reaction container, and saving of the tetrahydrofuran reagent toreduce the cost; and the combination solution achieves a good reaction enantioselectivity and a high enantiomeric excess value (% ee) of a product when applied to Corey asymmetric reduction.

Synthesis of nido-B11H14- and alkyl derivatives via systematic cage enlargement of the decaborane(14) system: Crystal structure of 7-Thx-B11H13-

Gaines, Donald F.,Bridges, Adam N.,Hayashi, Randy K.

, p. 1243 - 1244 (2008/10/08)

-

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