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Lithium tri-sec-butylborohydride

Lithium tri-sec-butylborohydride, dissolved as a mole solution in tetrahydrofuran, plays an important role in the field of organic synthesis as a mild and highly stereoselective strong reducing agent. It is widely used in the asymmetric selective reduction of ketones to produce alcohols. At the same time, it can also effectively catalyze the 1,4 conjugate addition reduction reaction of enols to produce ketones or alcohols. In addition, tri-sec-butyl-lithium borohydride is also suitable for the selective reduction of conjugated double bonds and iodides in exocyclic acrylonitrile derivatives. It has demonstrated excellent desemracemic properties in dilipid, dehalogenated monocymidine, rearrangement of 5-trimethylsilylbaine, and de-protected n-methoxycarbonyl opioid substitutions for N-non-opioids. In particular, tri-sec-butyl-lithium borohydride can effectively reduce conjugated carbonyl compounds at low temperatures, showing its excellent reducing ability.

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Borohydride
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176
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2024-08-22 13:56:40
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Detailed Description

Name	Lithium tri-sec-butylborohydride
Synonyms	L-selectride
	L-SELECTRIDE(R)
	l-selectride solution
	Lithiumbutylborohydride
	LITHIUM TRI-S-BUTYLHYDROBORATE
	LITHIUM TRIISOBUTYLHYDROBORATE
	Lithium triisobutylhydroborate
	lithium tri-sec-butylhydroborate
	LITHIUM TRI-SEC-BUTYLBOROHYDRIDE
	Lithium tri-sec-butylborohydride
	LITHIUM TRI-SEC-BUTYLHYDRIDOBORATE
	LITHIUM TRI-SEC-BUTYLBOROHYDRIDE, 1M IN THF
	lithium hydrido[tris(1-methylpropyl)]borate(1-)
	(beta-4)-borate(1-hydrotris(1-methylpropyl)-lithium
CAS	38721-52-7
EINECS	254-101-1
InChI	InChI=1/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
Physico-chemical Properties
Molecular Formula	C12H25BLi
Molar Mass	187.08
Density
Flash Point
Water Solubility	reacts
Solubility	Miscible with tetrahydrofuran.
Appearance	Liquid
Color	Colorless to yellow
BRN	4007327
Storage Condition	Flammables area
Sensitive	Moisture Sensitive
Risk and Safety
Risk Codes	R11 - Highly Flammable
	R14/15 -
	R17 - Spontaneously flammable in air
	R34 - Causes burns
	R35 - Causes severe burns
	R19 - May form explosive peroxides
	R40 - Limited evidence of a carcinogenic effect
	R37 - Irritating to the respiratory system
Safety Description	S16 - Keep away from sources of ignition.
	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 ... (there follows the type of fire-fighting equipment to be used.)
	S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
	S7/8 -
	S30 - Never add water to this product.
UN IDs	UN 3394 4.2/PG 1
WGK Germany	1
FLUKA BRAND F CODES	10
TSCA	Yes
HS Code	29319090
Hazard Class	4.3
Packing Group	II
Reference Information
EPA chemical information	Information provided by: ofmpub.epa.gov (external link)
product description	lithium tri-sec-butyl borohydride, the commercial form of this product is one mole solution dissolved in tetrahydrofuran. This product is widely used as a mild and highly stereoselective Strong reducing agent in Organic synthesis. It is used for asymmetric selective reduction of ketones to obtain alcohols. It can also be used for conjugated addition and reduction of enols 1 and 4 to obtain ketones or alcohols. It is used for selective reduction of conjugated double bonds and iodides of extracyclic propylene fine derivatives. For diesters, dehalogenated monocyclic pyrimidine, in the rearrangement of 5-trimethylsilylbain and deprotected N-methoxycarbonyl opioid substitution of N-non-opioid reactions, it is an effective de-racemization reagent, under low temperature conditions, Can effectively reduce conjugated carbonyl compounds.
characteristics	lithium tri-sec-butyl borohydride is a new type of hydride reducing agent, which has the characteristics of strong reduction ability, high regional and stereoselectivity.
Use	Lithium tri-sec-butyl borohydride is a particularly powerful and highly stereoselective reducing agent for diastereoselective reduction of ketone compounds, so that alcohol compounds are selectively reduced. It is also an effective de-racemization reagent, which can effectively reduce conjugated carbonyl compounds under low temperature conditions, and can be used in the pharmaceutical industry and perfume industry.

Lithium tri-sec-butylborohydride is an important organic compound, which has been widely used in many fields such as Chemical synthesis, material preparation and energy science. Below, we will discuss the characteristics of Lithium tri-sec-butylborohydride in detail in order to better understand and apply this compound.

First, from the perspective of chemical structure, Lithium tri-sec-butylborohydride shows its unique molecular configuration. The compound contains a variety of elements including boron, hydrogen, lithium and carbon, and the interaction between these elements gives trIS lithium borohydride its unique chemical properties. This compound is highly Reactive and can react with other compounds in a variety of chemical reactions to form entirely new compounds.

Secondly, Lithium tri-sec-butylborohydride showed superior selectivity during the reaction. It is able to precisely target specific functional groups for reduction, while remaining inert to other functional groups, without any effect. This unique selectivity gives Lithium tri-sec-butylborohydride an important advantage in the synthesis of complex compounds, helping to avoid unnecessary side reactions and the formation of products, thereby improving the efficiency and purity of the reaction.