1-(2-aminonaphthalen-1-yl)naphthalen-2-amine

• ChemBase ID: 139649
• Molecular Formular: C20H16N2
• Molecular Mass: 284.35444
• Monoisotopic Mass: 284.13134852
• SMILES: c1ccc2c(c1)ccc(c2c1c2ccccc2ccc1N)N
• Canonical SMILES: Nc1ccc2c(c1c1c(N)ccc3c1cccc3)cccc2
• InChI: InChI=1S/C20H16N2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12H,21-22H2
• InChIKey: DDAPSNKEOHDLKB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2-aminonaphthalen-1-yl)naphthalen-2-amine
• IUPAC Traditional name: 1-(2-aminonaphthalen-1-yl)naphthalen-2-amine
• Synonyms: (R)-(+)-DABN; (R)-(+)-1,1′-Bi(2-naphthylamine); (R)-(+)-1,1′-Binaphthalene-2,2′-diamine; (R)-(+)-2,2′-Diamino-1,1′-binaphthalene; (R)-(+)-1,1′-Binaphthyl-2,2′-diamine; (S)-(-)-DABN; (S)-(-)-1,1′-Bi(2-naphthylamine); (S)-(-)-1,1′-Binaphthalene-2,2′-diamine; (S)-(-)-2,2′-Diamino-1,1′-binaphthalene; (S)-(-)-1,1′-Binaphthyl-2,2′-diamine; (S)-BINAM; (S)-(-)-2,2'-Diamino-1,1'-binaphthyl; (S)-(-)-1,1'-Bi(2-naphthylamine); (R)-BINAM; (R)-(+)-2,2'-Diamino-1,1'-binaphthyl; (R)-(+)-1,1'-Bi(2-naphthylamine); (R)-[1,1'-Binaphthalene]-2,2'-diamine; (S)-(-)-1,1'-Binaphthyl-2,2'-diamine; (1,1'-biNaphthalene)-2,2'-diamine; (r)-(+)-2,2'-diamino-1,1'-biNaphthalene; (s)-(-)-2,2'-diamino-1,1'-biNaphthalene; ( )-1,1'-Binaphthyl-2,2'-diamine; ( )-BINAM; ( )-1,1'-Bi(2-naphthylamine); 1,1′-Binaphthyl-2,2′-diamine; (S)-(-)-1,1′-Bi(2-naphthylamine); (R)-(+)-1,1′-Bi(2-naphthylamine); (R)-(+)-1,1′-联(2-萘胺); (R)-(+)-1,1′-联萘-2,2′-二胺; (R)-(+)-2,2′-二氨基-1,1′-联萘; (R)-(+)-1,1′-联萘-2,2′-二胺; (S)-(-)-1,1′-联(2-萘胺); (S)-(-)-1,1′-联萘-2,2′-二胺; (S)-(-)-2,2′-二氨基-1,1′-联萘; (S)-(-)-1,1′-联萘-2,2′-二胺; (S)-(-)-1,1'-二(2-萘胺); (R)-(+)-1,1'-联(2-萘胺); ( )-1,1'-双(2-萘胺); 1,1′-联萘-2,2′-二胺; (S)-(-)-1,1′-联(2-萘胺); (R)-(+)-1,1′-联(2-萘胺)

Database IDs

• CAS Number: 18741-85-0; 4488-22-6; 18531-95-8
• EC Number: 000-000-0
• MDL Number: MFCD00145204
• Beilstein Number: 5279621; 2419071
• PubChem SID: 24859701; 24863894; 24882434; 24859700; 24863896; 162233897
• PubChem CID: 20571

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.9269788
• LogD (pH = 7.4): 3.9413865
• Log P: 3.9415727
• Molar Refractivity: 93.4954 cm^3
• Polarizability: 38.99884 Å^3
• Polar Surface Area: 52.04 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: slightly beige
• Melting Point: 188-193°C; 238-242°C; 240-242 °C; 240-243 °C; 240-244 °C(lit.); 242-243°C; 242-244 °C(lit.)
• Optical Rotation: [α]20/D +156±2°, c = 1% in pyridine; [α]20/D +157°, c = 1 in pyridine; [α]20/D -156±2°, c = 1% in pyridine; [α]20/D -157°, c = 1 in pyridine

Safety Information

• RTECS: DU3090000
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-41; 36/37/38
• Safety Statements: 26-36; 26-37; 26-39
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H302-H318; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.5% (sum of enantiomers, HPLC); 96%; 97%; 99%
• Grade: for chiral derivatization
• Optical Purity: ee: 99% (HPLC); enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Linear Formula: H2NC10H6C10H6NH2
• Empirical Formula (Hill Notation): C20H16N2

DETAILS

Sigma Aldrich - 382426

Caution
May darken in storage.
Packaging
1 g in glass bottle
Application
1,1′-Binaphthyl-2,2′-diamine derivatives have been used for asymmetric hydrogenations,1 cyclopropanations,2,3 and formation of chiral lactones.3,4,5

Sigma Aldrich - 631698

Packaging
1 g in glass bottle

Sigma Aldrich - 382434

Packaging
1 g in glass bottle
250 mg in glass bottle
Application
Used in the synthesis of chiral lactones.1

Sigma Aldrich - 32787

Other Notes
Preparation of N-alkylated derivatives and use as chiral auxiliaries 1,2; Amides of this diamine react diastereoselectively 3