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38721-52-7

38721-52-7 Structure

38721-52-7 Structure
IdentificationMore
[Name]

Lithium triisobutylhydroborate
[CAS]

38721-52-7
[Synonyms]

LITHIUM TRIISOBUTYLHYDROBORATE
LITHIUM TRI-S-BUTYLHYDROBORATE
LITHIUM TRI-SEC-BUTYLBOROHYDRIDE
LITHIUM TRI-SEC-BUTYLHYDRIDOBORATE
L-SELECTRIDE(R)
lithium,(beta-4)-borate(1-hydrotris(1-methylpropyl)-
lithiumtri-sec-butylborohydride,calselect?li,
lithiumtri-sec-butylborohydride,calselect?li,intetrahydrofuran
lithium tri-sec-butylhydroborate
Lithiumbutylborohydride
L-selectride
Lithium tri-sec-butylborohydride, in tetrahydrofuran, 1M solution
LITHIUM TRI-SEC-BUTYLBOROHYDRIDE SOL.
LITHIUM TRI-SEC-BUTYLBOROHYDRIDE SOL., 1 M IN THF A 800 ML
L-SELECTRIDE, 1.0M SOLUTION IN TETRAHYDR OFURAN
1.0MinTHF
1.0MsolutioninTHF
Lithium tri-sec-butylborohydride, 1M solution in THF
Borate(1-), hydrotris(1-methylpropyl)-, lithium, (T-4)-
lithium tri-sec-butylborohydride solution
[EINECS(EC#)]

254-101-1
[Molecular Formula]

C12H28BLi
[MDL Number]

MFCD00011708
[Molecular Weight]

190.1
[MOL File]

38721-52-7.mol
Questions And AnswerBack Directory
[Description]

Lithium tri-sec-butylborohydride, commercially available as a one molar solution in tetrahydrofuran. It is widely used as a mild and strong reducing agent with high stereoselectivity in organic synthesis.
[Features]

Lithium tri-sec-butylborohydride is a new type of hydride reducing agent, which has the characteristics of strong reducing ability and high regio- and stereoselectivity.
[Preparation]

Lithium triisobutylhydroborate can be prepared by:In a 3000ml three-necked flask, add 1000ml of 1mol/L tri-sec-butylboron tetrahydrofuran solution, add 1000ml of 1mol/L triethylenediamine tetrahydrofuran solution simultaneously, introduce nitrogen to start stirring, put the mixture of the two in an ice-water bath After cooling to 0° C., 1000 ml of a 1 mol/L lithium aluminum hydride solution in tetrahydrofuran was slowly added dropwise to the above mixed solution with a constant pressure funnel for about 10 hours.
Chemical PropertiesBack Directory
[Appearance]

clear colourless solution
[density ]

0.89 g/mL at 25 °C
[Fp ]

1 °F
[storage temp. ]

Flammables area
[solubility ]

Miscible with tetrahydrofuran.
[form ]

Liquid
[color ]

Colorless to yellow
[Water Solubility ]

reacts
[Sensitive ]

Moisture Sensitive
[BRN ]

4007327
[InChI]

InChI=1S/C12H28B.Li/c1-7-10(4)13(11(5)8-2)12(6)9-3;/h10-13H,7-9H2,1-6H3;/q-1;+1
[InChIKey]

ACJKNTZKEFMEAK-UHFFFAOYSA-N
[SMILES]

[Li+].[BH-](C(C)CC)(C(C)CC)C(C)CC
[CAS DataBase Reference]

38721-52-7(CAS DataBase Reference)
[EPA Substance Registry System]

Borate(1-), hydrotris(1-methylpropyl)-, lithium, (T-4)- (38721-52-7)
Safety DataBack Directory
[Symbol(GHS) ]

Flame (GHS02)Corrosion (GHS05)Exclamation Mark (GHS07)Health Hazard (GHS08)
GHS02,GHS05,GHS07,GHS08
[Signal word ]

Danger
[Hazard statements ]

H318-H225-H250-H260-H314-H335-H351
[Precautionary statements ]

P310-P370+P378i-P402+P404-P210-P231+P232-P280-P305+P351+P338-P370+P378-P422
[Hazard Codes ]

F,C
[Risk Statements ]

R11:Highly Flammable.
R14/15:Reacts violently with water, liberating extremely flammable gases .
R17:Spontaneously flammable in air.
R34:Causes burns.
R35:Causes severe burns.
R19:May form explosive peroxides.
[Safety Statements ]

S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S7/8:Keep container tightly closed and dry .
S30:Never add water to this product .
[RIDADR ]

UN 3394 4.2/PG 1
[WGK Germany ]

1
[F ]

10
[TSCA ]

Yes
[REACH Registrations]

Active
[HazardClass ]

4.3
[PackingGroup ]

II
[HS Code ]

29319090
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Tri-sec-butylborane-->Lithium Aluminum Hydride
Hazard InformationBack Directory
[Physical properties]

clear colourless solution
[Uses]

Lithium triisobutylhydroborate is used as a reducing agent. Reagent for: Enantioselective synthesis of a-amino acids via reduction of N-tert-butanesulfinyl ketimine esters. Diastereoselective reduction reactions. Hydride reduction of the Danishefsky pyranones. Asymmetric reductive aldol reaction of enones with a-alkoxy aldehydes. Synthesis of alkanols by carbonylation reactions.
[Uses]

L-Selectride Solution is a reducing agent which is used in the preparation of oxygen heterocycles. Used also as a reactant in the synthesis of novel bicicyclo[3.1.0]hexane analags which may prove useful in the treatment of depression.
[Production Methods]

L-Selectride can be readily prepared by addition of tri-sec-butylborane to a tetrahydrofuran solution of lithium aluminium hydride at room temperature. It is obtained as colorless solution in tetrahydrofuran[1].
L-Selectride preparation
[References]

[1] H.J.-Wang. (2009). Lithium tri-sec-Butylborohydride (l-Selectride): A Powerful and Highly StereoselectiveReducing Reagent. Synlett, 34 1, 2037–2038. https://doi.org/10.1055/S-0029-1217551
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Lithium tri-sec-butylborohydride, 1M solution in THF, AcroSeal?(38721-52-7)
[Alfa Aesar]

Lithium tri-sec-butylborohydride, 1.0M solution in THF, pa ckaged under Argon in resealable ChemSeal™ bottles(38721-52-7)
[Sigma Aldrich]

38721-52-7(sigmaaldrich)
[TCI AMERICA]

Lithium Tri-sec-butylborohydride  (21% in Tetrahydrofuran, ca. 1.0mol/L)(38721-52-7)
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