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(S)-N-Boc-pyrrolidin-2-ylboronic acid, also known as (2S)-2-(tert-Butoxycarbonyl)pyrrolidin-2-ylboronic acid, is a specialized chiral boronic acid used in research and laboratory applications, particularly in the field of organic chemistry. It belongs to the group of organic boronic acids, which are notable for their ability to form stable covalent bonds with diverse substrates and are commonly used in various synthesis processes like Suzuki-Miyaura coupling reactions. The (S) prefix in its name indicates its stereochemistry, making it a chiral compound with different forms that are mirror images of each other.

149716-79-0

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  • 1-Pyrrolidinecarboxylic acid, 2-borono-, 1-(1,1-dimethylethyl) ester, (2S)-

    Cas No: 149716-79-0

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149716-79-0 Usage

Uses

Used in Organic Chemistry Research:
(S)-N-Boc-pyrrolidin-2-ylboronic acid is used as a reagent for the synthesis of various organic compounds. Its ability to form stable covalent bonds with a wide range of substrates makes it a valuable tool in the development of new chemical entities and the modification of existing ones.
Used in Pharmaceutical Industry:
(S)-N-Boc-pyrrolidin-2-ylboronic acid is used as an intermediate in the synthesis of pharmaceutical compounds. Its unique chemical properties and reactivity allow for the creation of novel drug candidates with potential therapeutic applications.
Used in Material Science:
(S)-N-Boc-pyrrolidin-2-ylboronic acid is used as a building block in the development of new materials with specific properties. Its versatility in forming covalent bonds can lead to the creation of advanced materials with applications in various industries, such as electronics, energy, and biotechnology.
Used in Suzuki-Miyaura Coupling Reactions:
(S)-N-Boc-pyrrolidin-2-ylboronic acid is used as a coupling partner in Suzuki-Miyaura coupling reactions, a widely used method for the formation of carbon-carbon bonds. This reaction is essential in the synthesis of complex organic molecules, including those found in pharmaceuticals and agrochemicals.

Check Digit Verification of cas no

The CAS Registry Mumber 149716-79-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,9,7,1 and 6 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 149716-79:
(8*1)+(7*4)+(6*9)+(5*7)+(4*1)+(3*6)+(2*7)+(1*9)=170
170 % 10 = 0
So 149716-79-0 is a valid CAS Registry Number.
InChI:InChI=1S/C9H18BNO4/c1-9(2,3)15-8(12)11-6-4-5-7(11)10(13)14/h7,13-14H,4-6H2,1-3H3/t7-/m1/s1

149716-79-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Boc-Pyrrolidin-2-(S)-ylboronic acid

1.2 Other means of identification

Product number -
Other names (S)-N-Boc-pyrrolidin-2-ylboronic acid

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:149716-79-0 SDS

149716-79-0Downstream Products

149716-79-0Relevant articles and documents

Preparing technology of chiral N-BOC-pyrrolidine-2-boric acid

-

, (2018/07/03)

The invention discloses a preparing technology of chiral N-BOC-pyrrolidine-2-boric acid, and belongs to the field of agent intermediate synthesis. N-BOC-pyrrolidine and sec-butyllithium are subjectedto proton abstraction at low temperature, halogen boron agent is added, after a reaction is completed, saturated ammonium chloride is added to conduct cancellation, after evaporation to dryness of anorganic layer, mandelic acid and ethyl acetate are added, and after salt resolution, acidic hydrolysis is conducted to obtain chiral N-BOC-pyrrolidine-2-boric acid. By means of the method, the operating steps are short, raw materials are easily recycled, products with two structures can be obtained simply by changing the structure of a resolving agent, and the preparing technology has potential practical value.

A (-)-sparteine-directed highly enantioselective synthesis of boroproline. Solid- and solution-state structure and properties

Batsanov, Andrei S.,Grosjean, Christophe,Schuetz, Thorben,Whiting, Andrew

, p. 6276 - 6279 (2008/02/10)

(Chemical Equation Presented) A two-step, direct asymmetric synthesis of the trifluoroacetate ammonium salt of boroproline is reported. (-)-Sparteine-mediated lithiation of N-Boc-pyrrolidine afforded N-Boc-aminoboronic acid in good yield and enantioselectivity as determined by HPLC (pinanediol ester). Deprotection using TFA yielded the ammonium salt; full characterization data are presented, and the structure in aqueous solution and the occurrence of a B-N species are discussed.

A practical synthesis of L-valyl-pyrrolidine-(2R)-boronic acid: Efficient recycling of the costly chiral auxiliary (+)-pinanediol

Gibson, Frank S.,Singh, Ambarish K.,Soumeillant, Maxime C.,Manchand, Percy S.,Humora, Michael,Kronenthal, David R.

, p. 814 - 816 (2013/09/06)

A practical synthesis of L-valyl-pyrrolidine-(2R)-boronic acid (1) is detailed. A previously disclosed synthesis of 1 (Snow, R.; Kelly, T. R.; Adams, J.; Coutts, S.; Perry, C. (Boehringer Ingelheim Pharmaceuticals, Inc.). WO 93/10127, 1993) was significantly improved by developing an efficient process for recycling the costly chiral auxiliary (+)- pinanediol.

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