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BINAP is an acronym for the organophosphorus compound 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl. This chiral ligand
Ligand

In chemistry, a ligand is either an atom, ion, or molecule that bonds to a central metal, generally involving formal donation of one or more of its electrons....
 is widely used in asymmetric synthesis
Chiral synthesis

Asymmetric synthesis, also called chiral synthesis, enantioselective synthesis or stereoselective synthesis, is organic synthesis which introduces one or more new and desired elements of chirality....
. It consists of a pair of 1-diphenylphosphinonaphthyl
Naphthalene

Naphthalene, also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or antimite and not to be confused with naphtha, is a crystalline, Aromaticity, white, solid hydrocarbon with formula Carbon10hydrogen8 and the structure of two fused benzene rings....
 groups linked at the 2 positions (Figure 1). This C2-symmetric framework lacks stereogenic atom
Stereocenter

A stereocenter, or stereogenic center, is any point, though not necessarily an atom, in a molecule bearing groups such that an interchanging of any two groups leads to a stereoisomer ....
 (see axial chirality
Axial chirality

Axial chirality is a special case of chirality in which a molecule does not possess a stereogenic center but an axis of chirality - an axis is about which a set of substituents is held in a spatial arrangement that is not superposable on its mirror image....
). The barrier to racemization is high due to steric hindrance that limits rotation about the bond linking the naphthyl rings.






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BINAP is an acronym for the organophosphorus compound 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl. This chiral ligand
Ligand

In chemistry, a ligand is either an atom, ion, or molecule that bonds to a central metal, generally involving formal donation of one or more of its electrons....
 is widely used in asymmetric synthesis
Chiral synthesis

Asymmetric synthesis, also called chiral synthesis, enantioselective synthesis or stereoselective synthesis, is organic synthesis which introduces one or more new and desired elements of chirality....
. It consists of a pair of 1-diphenylphosphinonaphthyl
Naphthalene

Naphthalene, also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or antimite and not to be confused with naphtha, is a crystalline, Aromaticity, white, solid hydrocarbon with formula Carbon10hydrogen8 and the structure of two fused benzene rings....
 groups linked at the 2 positions (Figure 1). This C2-symmetric framework lacks stereogenic atom
Stereocenter

A stereocenter, or stereogenic center, is any point, though not necessarily an atom, in a molecule bearing groups such that an interchanging of any two groups leads to a stereoisomer ....
 (see axial chirality
Axial chirality

Axial chirality is a special case of chirality in which a molecule does not possess a stereogenic center but an axis of chirality - an axis is about which a set of substituents is held in a spatial arrangement that is not superposable on its mirror image....
). The barrier to racemization is high due to steric hindrance that limits rotation about the bond linking the naphthyl rings. The dihedral angle
Dihedral angle

In geometry, the angle between two Plane s is called their dihedral or torsion angle.The dihedral angle of two planes can be seen by looking at the planes "edge on", i.e., along their line of intersection....
 is approximately 90°.

BINAP is used in organic synthesis
Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
 for enantioselective transformations catalyzed by its complexes
Complex (chemistry)

In chemistry, a complex, also called a "coordination compound" or "metal complex", is a structure consisting of a central atom or molecule connected to surrounding atoms or molecules....
 of ruthenium
Ruthenium

Ruthenium is a chemical element that has the symbol Ru and atomic number 44. A rare transition metal of the platinum group of the periodic table, ruthenium is found associated with platinum ores and used as a catalyst in some platinum alloys....
, rhodium
Rhodium

Rhodium is a chemical element that is a rare, silvery-white, hard transition metal and a member of the platinum group. Rhodium is found in platinum ores and is used in alloys with platinum and as a catalyst....
, and palladium
Palladium

Palladium is a rare and lustrous silvery-white metal that was discovered in 1803 by William Hyde Wollaston, who named it palladium after the 2 Pallas, which in turn, was named after the epithet of the Greek mythology goddess Athena, acquired by her when she slew Athena#Pallas_Athena....
. As pioneered by Ryoji Noyori
Ryoji Noyori

is a Japanese chemist. He won the Nobel Prize in Chemistry in 2001. Noyori shared half of the prize with William S. Knowles for the study of chirally catalyzed hydrogenations; the second half of the Prize went to K....
 and his co-workers, Rh complexes of BINAP are useful for the synthesis of (-)-menthol
Menthol

Menthol is an organic compound #Production or obtained from peppermint or other Mentha oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above....
. This synthetic method was industrialized by Takasago International Corporation. In part for this work, Ryoji Noyori
Ryoji Noyori

is a Japanese chemist. He won the Nobel Prize in Chemistry in 2001. Noyori shared half of the prize with William S. Knowles for the study of chirally catalyzed hydrogenations; the second half of the Prize went to K....
 was awarded the 2001 Nobel Prize in Chemistry
Nobel Prize in Chemistry

The Nobel Prize in Chemistry is awarded annually by the Royal Swedish Academy of Sciences to scientists in the various fields of chemistry. It is one of the five Nobel Prizes established by the will of Alfred Nobel in 1895, awarded for outstanding contributions in chemistry, Nobel Prize in Physics, Nobel Prize in Literature, Nobel Peace Pri...
.

BINAP is prepared from BINOL (1,1'-bi-2-naphthol
1,1'-Bi-2-naphthol

1,1'-Bi-2-naphthol is an organic compound that is often used as a ligand for transition-metal catalysed asymmetric synthesis. BINOL has axial chirality and the two enantiomers can be readily separated and are stable toward racemisation....
) via its bis-triflate derivatives. Both the R and S enantiomer
Enantiomer

In chemistry, an enantiomer is one of two stereoisomers that are Superpose complete mirror images of each other, much as one's left and right Chirality are "the same" but opposite....
s as well as the racemate are commercially available.

BINOL can be reacted with Chlorodiphenylphosphine
Chlorodiphenylphosphine

Chlorodiphenylphosphine is a liquid with a very pungent odor that is often described as being garlic-like and detectable even in the ppb range....
 to make phosphinous acid, diphenyl-[1,1'-binapthalene]-2-2'-diyl ester (BINAPO)