89104-48-3

Basic information

• Product Name: (4R,5R)-2-CHLORO-4,5-DIMETHYL-1,3,2-DIOXAPHOSPHOLANE 2-OXIDE
• Synonyms: (4R,5R)-(+)-2-CHLORO-4,5-DIMETHYL-1,3,2- DIOXAPHOSP;(4R,5R)-(+)-2-CHLOR-4,5-DIMETHYL-1,3,2-;(+)-BIS[(R)-1-PHENYLETHY]AMINE HYDROCHLORIDE;(S)-TERT-BUTYL 1-(4-HYDROXYPHENYL)ETHYLCARBAMATE;(S)-(1,2,3,4-tetrahydro-7-methoxy-2-naphthyl)amine;2-chloro-4,5-dimethyl-1,3,2-dioxaphospholane-2-oxide;(4R,5R)-2-Chloro-4,5-diMe.-1,3,2-Dioxa-P;(4R,5R)-2-CHLORO-4,5-DIMETHYL-1,3,2-DIOXAPHOSPHOLANE 2-OXIDE
• CAS NO: 89104-48-3
• Molecular Formula: C₄H₈ClO₃P
• Molecular Weight: 170.53
• Product Categories: chiral
• Mol File: 89104-48-3.mol
• Article Data: 1

Chemical Properties

• Flash Point: 56 °C
• Appearance: /
• Density: 1.300 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.437
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (4R,5R)-2-CHLORO-4,5-DIMETHYL-1,3,2-DIOXAPHOSPHOLANE 2-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5R)-2-CHLORO-4,5-DIMETHYL-1,3,2-DIOXAPHOSPHOLANE 2-OXIDE(89104-48-3)
• EPA Substance Registry System: (4R,5R)-2-CHLORO-4,5-DIMETHYL-1,3,2-DIOXAPHOSPHOLANE 2-OXIDE(89104-48-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 89104-48-3(Hazardous Substances Data)

Usage

General Description

(4R,5R)-2-CHLORO-4,5-DIMETHYL-1,3,2-DIOXAPHOSPHOLANE 2-OXIDE is a chemical compound that is used in organic synthesis and pharmaceutical research. It is a phospholane oxide, which is a type of organophosphorus compound. This particular compound has a chloro substitution at the 2 position and methyl groups at the 4 and 5 positions of the phospholane ring. It is commonly used as a chiral building block in the synthesis of various pharmaceuticals and agrochemicals. Additionally, it can be used as a ligand in asymmetric catalysis to facilitate enantioselective reactions. Its unique structure and chiral properties make it a valuable tool in the production of chiral molecules with specific biological activity.

InChI:InChI=1/C4H8ClO3P/c1-3-4(2)8-9(5,6)7-3/h3-4H,1-2H3/t3-,4-/m1/s1

Upstream product

• 6982-25-8 d,l-2,3-butanediol 
• 1029272-42-1 (2R,3S)-2,3-butanediol 

Downstream Products

• 88853-17-2 (2S,4S,5R)-4,5-Dimethyl-2-phenoxy-[1,3,2]dioxaphospholane 2-oxide 
• 88853-18-3 (2R,4R,5S)-4,5-Dimethyl-2-phenoxy-[1,3,2]dioxaphospholane 2-oxide 
• 112245-48-4 (4R,5R)-2-<(1'S)-1'-methyl-3'-(trityloxy)propoxy>-4,5-dimethyl-1,3,2-dioxaphospholane 2-oxide 
• 112114-71-3 (4R,5R)-2-<(1'R)-1'-methyl-3'-(trityloxy)propoxy>-4,5-dimethyl-1,3,2-dioxaphospholane 2-oxide 
• 2365-02-8 (4R,5R)-4,5-Dimethyl-2-(4-nitro-phenoxy)-[1,3,2]dioxaphospholane 2-oxide 
• 2365-02-8 racem-4,5-Dimethyl-2-<4-nitro-phenoxy>-1,3,2-dioxaphospholan-2-oxid 

Relevant articles and documents

Chemistry of β-(phosphatoxy)alkyl and β-(acyloxy)alkyl radicals. Migration reactions: Scope and stereoselectivity of β-(phosphatoxy)alkyl rearrangement. Mechanism of β-(phosphatoxy)alkyl and β-(acyloxy)alkyl migration

An in depth study of the mechanism of the β-(phosphatoxy)alkyl radical migration is presented. Examples are presented which define the scope and limitations of the migration and show that, in certain cases, it is highly stereoselective. It is shown that phosphoranyl radicals are not intermediates in this rearrangement. A series of experiments with stereochemically-, 18O-, and deuterium-labeled probes indicate that the migration is intramolecular, proceeds through competing 1,2- and 2,3-pathways, and does not involve fragmentation to a cage pair followed by recombination. The deuterium-labeled probe is also applied to the β-(acyloxy)alkyl migration with the same result. The changing proportions of 1,2- and 2,3-shifts in going from the β-(phosphatoxy)alkyl to the β-(acyloxy)alkyl migration are discussed in terms of the conformational equilibria of the two different esters and the Curtin-Hammett principle.