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(S)-(+)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate

Catalog Number
ACM35193647
Product Name
(S)-(+)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate
CAS
35193-64-7
  • Product Overview
  • Usage
Synonyms
(aS)-2,2'-Phosphinicobisoxy-1,1'-binaphthalene; (R)-(-)-BNP ACID; AK163708; ANW-28102; SC11524; J-019988; (+/-)1,1'-binaphthyl-2,2'-diyl hydrogen phosphate; RT-003435; VC30236; (+/-)-2,2'-Dihydroxy-1,1'-binaphthyl Hydrogenphosphate;
IUPAC Name
13-hydroxy-12,14-dioxa-13λ5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene 13-oxide;
Molecular Weight
348.294g/mol
Molecular Formula
C20H13O4P;
Canonical SMILES
C1=CC=C2C(=C1)C=CC3=C2C4=C(C=CC5=CC=CC=C54)OP(=O)(O3)O;
InChI
InChI=1S/C20H13O4P/c21-25(22)23-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)24-25/h1-12H,(H,21,22);
InChI Key
JEHUZVBIUCAMRZ-UHFFFAOYSA-N;
Storage
Refrigerator
Complexity
508
Covalently-Bonded Unit Count
1
EC Number
609-734-1
Exact Mass
348.055g/mol
H-Bond Acceptor
4
H-Bond Donor
1
Heavy Atom Count
25
Monoisotopic Mass
348.055g/mol
NSC Number
244999
Topological Polar Surface Area
55.8A^2
Application
(S)-(+)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate serves as a versatile compound with several key applications in chemistry. It is primarily used as a chiral quenching agent, effectively participating in complex reactions due to its unique structure. One of its notable functions is as a chiral Brønsted acid catalyst, where it enhances the enantioselective Mannich reaction, a process significant for the synthesis of various pharmaceuticals. Additionally, it is involved in the asymmetric hetero Diels-Alder reaction, facilitated by its interaction with chiral lanthanide(III) complexes. Beyond these roles, it acts as an efficient acidic resolving agent for certain amine and racemic mixtures, making it invaluable in producing enantiomerically pure compounds. This compound typically appears as a white to light yellow crystalline powder, reflecting its purity and readiness for use in sophisticated chemical processes.
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