Editing BINAP (section)

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 435068880
| ImageFile = BINAP Enantiomers Structural Formulae V.1.svg
| ImageSize = 250
| PIN = ([1,1′-Binaphthalene]-2,2′-diyl)bis(diphenylphosphane)
| OtherNames = BINAP
|Section1={{Chembox Identifiers
| CASNo = 76189-55-4
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Comment = (''R'')
| CASNo1 = 76189-56-5
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1_Comment = (''S'')
| PubChem = 634876
| PubChem_Comment = (+)
| EC_number = 616-304-7
619-338-0
616-305-2
918-620-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4F1X2F8NA3
| UNII_Comment = (''R'')
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = OX12238KWH
| UNII1_Comment = (''S'')
| ChEMBL = 1275990
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 551072
| ChemSpiderID_Comment = (Rac)
| SMILES = c1ccc(cc1)P(c2ccccc2)c3ccc4ccccc4c3c5c6ccccc6ccc5P(c7ccccc7)c8ccccc8
| SMILES_Comment = (Rac)
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C44H32P2/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38/h1-32H
| StdInChI_Comment = (Rac)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = MUALRAIOVNYAIW-UHFFFAOYSA-N
  }}
|Section2={{Chembox Properties
| C=44 | H=32 | P=2
| Appearance = Colorless solid
| Density =
| MeltingPtC = 239 to 241
| MeltingPt_notes = (''R'')<br>238–240&nbsp;°C (''S'')
| BoilingPt = 
| Solubility = organic solvents
  }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt = 
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335|413}}
| PPhrases = {{P-phrases|261|264|271|273|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
 }}
}}

[[Image:BINAP 3D.png|thumb|right|Ball and stick model of BINAP viewed as above]]

'''BINAP''' (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) is an [[organophosphorus compound]].  This [[Optical isomerism|chiral]] [[diphosphines|diphosphine]] [[ligand]] is widely used in [[chiral synthesis|asymmetric synthesis]].  It consists of a pair of 2-diphenylphosphino[[naphthalene|naphthyl]] groups linked at the 1 and 1′ positions.  This [[C2-Symmetric ligands|C<sub>2</sub>-symmetric framework]] lacks a [[stereocenter|stereogenic atom]], but has [[axial chirality]] due to restricted rotation ([[atropisomer]]ism). The barrier to [[racemization]] is high due to [[steric hindrance]], which limits rotation about the bond linking the naphthyl rings.  The [[dihedral angle]] between the naphthyl groups is approximately 90°.  The natural [[bite angle]] is 93°.<ref name="vanLeeuwen">{{cite journal |last1=Birkholz (née Gensow) |first1=Mandy-Nicole |last2=Freixa |first2=Zoraida |last3=van Leeuwen |first3=Piet W. N. M. |title=Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions |journal=Chemical Society Reviews |date=2009 |volume=38 |issue=4 |pages=1099–1118 |doi=10.1039/B806211K |pmid=19421583}}</ref>