115651-77-9

Basic information

• Product Name: (1R,2S)-2-DI-N-BUTYLAMINO-1-PHENYL-1-PROPANOL
• Synonyms: N,N-DIBUTYLNOREPHEDRINE;(+)-N,N-DI-N-BUTYLNOREPHEDRIN;(1R,2S)-2-DI-N-BUTYLAMINO-1-PHENYL-1-PROPANOL;(1R,2S)-(+)-2-(DIBUTYLAMINO)-1-PHENYL-1-PROPANOL;(+)-ALPHA-[1-(N,N-DI-N-BUTYLAMINO)ETHYL]BENZYL ALCOHOL;N,N-DIBUTYL-L-NOREPHEDRINE;(+)-DBNE, N,N-Dibutyl-L-(+)-norephedrine;(+)-DBNE, (1R,2S)-2-Dibutylamino-1-phenyl-1-propanol
• CAS NO: 115651-77-9
• Molecular Formula: C₁₇H₂₉NO
• Molecular Weight: 263.42
• Product Categories: Amino Alcohols (Chiral);Asymmetric Synthesis;Chiral Building Blocks;Synthetic Organic Chemistry
• Mol File: 115651-77-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 121 °C0.1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.944 g/mL at 20 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.501(lit.)
• PKA: 13.91±0.20(Predicted)
• CAS DataBase Reference: (1R,2S)-2-DI-N-BUTYLAMINO-1-PHENYL-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-2-DI-N-BUTYLAMINO-1-PHENYL-1-PROPANOL(115651-77-9)
• EPA Substance Registry System: (1R,2S)-2-DI-N-BUTYLAMINO-1-PHENYL-1-PROPANOL(115651-77-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 115651-77-9(Hazardous Substances Data)

Usage

General Description

"(1R,2S)-2-Di-N-Butylamino-1-Phenyl-1-Propanol" is a chemical compound. It is an organic compound belonging to the class of chemicals known as tertiary alcohols. Tertiary alcohols are organic compounds in which a hydroxy group, a functional group with the structure -OH, is bonded to a saturated carbon atom. Typically, chemicals with this structure can have multiple applications across varied fields. However, available information on this specific compound "(1R,2S)-2-Di-N-Butylamino-1-Phenyl-1-Propanol"'s properties, uses, or potential applications seems to be not widely available, indicating that it may not be familiar or commonly used in the field of chemistry or related industries. Always follow safety and handling guidelines when working with any chemical compounds.

InChI:InChI=1/C17H29NO/c1-4-6-13-18(14-7-5-2)15(3)17(19)16-11-9-8-10-12-16/h8-12,15,17,19H,4-7,13-14H2,1-3H3/t15-,17-/m0/s1

Upstream product

• 109-65-9 1-bromo-butane 
• 492-41-1 (1R,2S)-norephedrine 
• 542-69-8 1-iodo-butane 

Relevant articles and documents

Asymmetric Sulfinylations of N-Methylephedrine-Modified Tri- or Tetraalkyl Zincates by Symmetric Diaryl Sulfoxides

Diethylzinc was treated with 1 or 2 equiv. of AlkMgCl or PhMgBr (preferably) or with 1 equiv. of nBuLi (less efficiently) for forming species – plausibly zincates – which were sulfinylated by diaryl sulfoxides to give racemic alkyl aryl sulfoxides in yields reaching 100 %. Dialkylzinc reagents were also activated by treatments with 1 or 2 equiv. of an enantiomerically pure alkylmagnesium β-aminoalkoxide. This worked best when the alkoxide stemmed from a dialkylmagnesium reagent and an equimolar amount of N-methyl-(–)-ephedrine. This second activation mode allowed sulfinylations of what was originally the dialkylzinc reagent with diaryl sulfoxides. This generated alkyl aryl sulfoxides with enantiomeric ratios up to 93:7 in up to 100 % yield.

Enantioselective Addition of Diethylzinc to α-Branched Aldehydes

Reaction of diethylzinc with α-branched aldehydes in the presence of a catalytic amount of (1R,2S)-(-)-1-phenyl-2-piperidinopropane-1-thiol 1 provided the corresponding secondary alcohols in almost 100percent enantiomeric excess.

Chiral N,N-Dialkylnorephedrines as Catalysts of the Highly Enantioselective Addition of Dialkylzincs to Aliphatic and Aromatic Aldehydes. The Asymmetric Synthesis of Secondary Aliphatic and Aromatic Alcohols of High Optical Purity

The chiral N,N-dialkylnorephedrine-catalyzed addition of dialkylzincs to aliphatic and aromatic aldehydes afforded secondary alcohols of high optical purity (to > 95percent ee).Among the N,N-di(primary alkyl)norephedrines, N,N-di-n-butylnorephedrine (DBNE, 3d) was found to be the most effective catalyst. 1-Phenyl-2-(1-pyrrolidinyl)propan-1-ol (3i) and N,N-diallylnorephedrine (3j) were also highly effective catalysts.The method described provides optically active secondary aliphatic alcohols of high optical purity which cannot be prepared by conventional methods.