85116-38-7

Basic information

• Product Name: (-)-IPC2B(ALLYL), 1M IN PENTANE
• Synonyms: (-)-B-Allyldiisopinocampheylborane solution;(-)-Ipc2B(allyl)borane solution;(-) - Ipc2B (allyl) borane;(-)-B-ALLYLDIISOPINOCAMPHEYLBORANE 1 M IN DIOXANE
• CAS NO: 85116-38-7
• Molecular Formula: C₂₃H₃₉B
• Molecular Weight: 326.37
• Mol File: 85116-38-7.mol
• Article Data: 52

Chemical Properties

• Boiling Point: 35-36 °C
• Flash Point: -49 °C
• Appearance: /
• Density: 0.638 g/mL at 25 °C
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.496
• Storage Temp.: ?20°C
• CAS DataBase Reference: (-)-IPC2B(ALLYL), 1M IN PENTANE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-IPC2B(ALLYL), 1M IN PENTANE(85116-38-7)
• EPA Substance Registry System: (-)-IPC2B(ALLYL), 1M IN PENTANE(85116-38-7)

Safety Data

• Hazard Codes: F+,Xn,N,F
• Statements: 12-51/53-65-66-67-40-36/37-19-11-36/37/38
• Safety Statements: 9-16-29-33-61-62-36/37-26
• RIDADR: UN 1265 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 85116-38-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C23H39B/c1-8-9-24(20-12-16-10-18(14(20)2)22(16,4)5)21-13-17-11-19(15(21)3)23(17,6)7/h8,14-21H,1,9-13H2,2-7H3/t14-,15-,16+,17+,18-,19-,20-,21-/m1/s1

Upstream product

• 2622-05-1 allylmagnesium bromide 
• 85116-37-6 (-)-diisopinocamphenylborane chloride 
• 1730-25-2 allylmagnesium bromide 
• 85134-98-1 (-)-B-methoxydiisopinocampheylborane 
• 7785-70-8 (+)-α-pinene 
• 21932-54-7 diisopinocampheylborane 
• 7103-09-5 4-but-1-enylmagnesium bromide 
• 99438-28-5 (+)-B-methoxydiisocamphenylborane 
• 106-95-6 allyl bromide 

Downstream Products

• 517907-57-2 (S)-(-)-1-(pyridin-2-yl)but-3-en-1-ol 
• 144635-03-0 (S)-1-(pyridin-3-yl)but-3-en-1-ol 
• 6398-51-2 (S)-1-(2-furyl)-3-buten-1-ol 
• 99328-46-8 (4R,5S)-5-Methyl-hept-1-en-4-ol 
• 99342-24-2 (4S,5S)-5-Methyl-hept-1-en-4-ol 
• 89046-67-3 (2S,3R)-2-methyl-1-(phenylmethoxy)hex-5-en-3-ol 
• 106357-32-8 (2S,3S)-1-(benzyloxy)-2-methylhept-5-en-3-ol 
• 106268-78-4 (4R,5S)-5-phenyl-1-hepten-4-ol 
• 106268-77-3 (4S,5S)-5-phenyl-1-hepten-4-ol 
• 106268-80-8 (4R,5R)-5-phenyl-1-hepten-4-ol 
• 106268-79-5 (4S,5R)-5-phenyl-1-hepten-4-ol 
• 94233-71-3 (4R,5S)-5-(phenylmethoxy)hex-1-en-4-ol 
• 94233-72-4 (4S,5S)-5-(phenylmethoxy)hex-1-en-4-ol 
• 85551-57-1 (R)-1-Phenylbut-3-en-1-ol 

Relevant articles and documents

Double diastereoselection in asymmetric [2+3] cycloaddition of chiral oxazoline N-oxides: Application to the kinetic resolution of a racemic α,β-unsaturated δ-lactone

The asymmetric [2+3] cycloaddition reaction between chiral oxazoline N-oxide 1 and α,β-unsaturated lactone 2 was studied. A double diastereoselection was observed, (1R)-1 and (R)-2 gave a mismatched pair with almost no cycloadduct obtained. A transition state model is proposed, accounting for the destabilization of transition state in the cycloaddition reaction. This result has led to kinetic resolution studies, in which both enantiomers of 1 were reacted with racemic lactone 2. The enantiomeric excess of the recovered lactone 2 was determined to be up to 70% ee, by 13C-{1H} NMR analysis in a chiral liquid crystalline solvent. The experimental results are in agreement with predicted enantiomeric excesses and consistent with the transition state models.

Approach to the Core Structure of 15- epi -Exiguolide

The synthesis of seco acid 41 of the macrolactone part of 15- epi -exiguolide, containing a bis-pyran subunit and a trans double bond, is described. Key features of the synthetic strategy include a Feringa-Minnaard asymmetric organocuprate addition to uns

Studies on C18-C20 aldol couplings of rhizopodin

The aldol addition of an enol(ate) to a carbonyl compound is one of the most powerful and versatile C-C bond forming reactions. In complex target synthesis the coupling of two chiral partners may complicate the stereochemical outcome by multiple stereoinductions. Here, we report studies on pivotal aldol couplings employed in the rhizopodin synthesis, detailing the various directing effects exerted by the stereogenic centers present in this sterically hindered connection. Georg Thieme Verlag Stuttgart. New York.

Syntheses of (-)-cryptocaryolone and (-)-cryptocaryolone diacetate via a diastereoselective oxy-Michael addition and oxocarbenium allylation

The total syntheses of both (-)-cryptocaryolone and (-)-cryptocaryolone diacetate is presented herein. The usage of a diastereoselective oxy-Michael addition/benzylidene acetal formation coupled with a selective axial oxocarbenium allylation allowed for the preparation of the α-C-glycoside moiety present in the bicyclic bridged structure. In addition, the syn-1,3-diol of the linear portion was installed via a Wacker oxidation followed by a subsequent directed reduction of the appropriate homoallylic alcohol precursor.