3D Mol Similar

(S)-(-)-1,1'-Bi-2-naphthol

Iupac Name：1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol

CAS No.: 18531-99-2

Molecular Weight：286.32

Modify Date.: 2022-11-11 05:18

Introduction: Chiral ligand. View more+

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1. Names and Identifiers

1.1 Name: (S)-(-)-1,1'-Bi-2-naphthol
1.2 Synonyms: (+/-)-1,1'-BINAPHTHALENE-2,2'-DIOL (1S)-[1,1'-Binaphthalene]-2,2'-diol (1S)-2,2'-DIHYDROXY-[1,1']-BINAPHTHYL (R)-(+)-1,1'-BI-2-NAPHTHOL (R)-(+)-2,2'-DIHYDROXY-1,1'-BINAPHTHYL (S)-(-)-1 1'-BI-2-NAPHTHOL (S)-(-)-1,1 -BI(2-NAPHTHOL)/(S)-(-)-1,1'-BINAPHTHALENE-2,2'-DIOL/(S)-(-)-BINOL/(S)-(+)-2,2'-DIHYDROXY-1,1'-DINAPHTHYL (S)-(-)-1,1&lsquo-Bi-2-naphthol (s)-(-)-1,1’-bi-2-nanphthol (S)-(-)-1,1'-BI(2-NAPHTHOL) (S)-(-)-1,1-Bi-2-naphthol (S)-(-)-1,1'-BI-2-NAPHTYOL (S)-(-)-1,1'-Binaphthalene-2,2'-diol (S)-(-)-1,1''-BINAPHTHYL-2,2''-DIOL FOR SY (S)-(-)-1,1'-BINAPHTHYL-2,2'-DIOL FOR SYNTHESIS (S)-(-)-2,2'-DIHYDROXY-1,1'-BINAPHTHYL (S)-(-)-2,2-Dihydroxy-1,1-Binaphthyl (S)-(-)-2,2'-Dihydroxy-1,1'-dinaphthyl (S)-(-)-BINOL (S)-(-)-BINOL (S)-(-)-2,2'-Dihydroxy-1,1'-binaphthyl (S)-(+)-1,1'-BI-2-NAPHTHOL (S)-(+)-1,1-BI-2-NAPHTHOL (S)-[1,1'-Binaphthalene]-2,2'-diol (S)-1,1'-BI-2-NAPHTHOL (S)-1,1-Bi-2-Naphthol (S)-1,1'-Binaphthalene-2,2'-diol, (S)-BINOL (S)-2,2'-DIHYDROXY-[1,1']-BINAPHTHYL [1,1']BINAPHTHALENYL-2,2'-DIOL 1,1'-BI-2,2'-NAPHTHOLS Dihydroxydinaphthylwhitepowder EINECS 210-014-0 MFCD00004068 S-(-)-1,1'-BI-2-NAPHTHOL S-(-)-1,1'-BI-2-NAPHTHOL / (S)-(-)BINOL S-(-)-1.1'-Bi-2-Naphthol S-(-)-1.1'-binaphthyl-2.2'-diol S-BINOL/S-(-)-1.1'-BINAPHTHYL-2.2'-DIOL

1.3 CAS No.: 18531-99-2

1.4 CID: 11762

1.5 EINECS(EC#): 606-050-5; 210-014-0; 606-048-4

1.6 Molecular Formula: C20H14O2 (isomer)

1.7 Inchi: InChI=1S/C20H14O2/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/h1-12,21-22H

1.8 InChkey: PPTXVXKCQZKFBN-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=C2C(=C1)C=CC(=C2C3=C(C=CC4=CC=CC=C43)O)O

1.10 Isomers Smiles: C1=CC=C2C(=C1)C=CC(=C2C3=C(C=CC4=CC=CC=C43)O)O

2. Properties

2.1 Density: 1 g/cm3

2.1 Melting point: 215-218 °C

2.1 Boiling point: 388.69°C (rough estimate)

2.1 Refractive index: -36.0 ° (C=1, THF)

2.1 Flash Point: 218.9°C

2.1 Precise Quality: 286.09900

2.1 PSA: 40.46000

2.1 logP: 5.07120

2.1 Solubility: dioxane: 50?mg/mL, clear

2.2 Appearance: Beige powder

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: white to light yellow crystal powde

2.5 Color/Form: White to light gray

2.6 pKa: 8.29±0.50(Predicted)

2.7 Water Solubility: dioxane: 50?mg/mL, clear

2.8 Stability: Stable under normal temperatures and pressures.

2.9 StorageTemp: Keep in dark place,Inert atmosphere,Room temperature

3. Use and Manufacturing

3.1 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 32 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H301 (87.5%): Toxic if swallowed [Danger Acute toxicity, oral]
H315 (18.75%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (96.88%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (12.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501

3.2 Purification Methods: Dissolve it in cold 2.5N NaOH, extract with CH2Cl2, and acidify with 5% HCl. Collect the white precipitate and recrystallise it from aqueous EtOH and dry it in a vacuum [Akimoto & Yamada Tetrahedron 27 5999 1971]. It is optically stable in dioxane-water (100o/24hours). Racemisation: 72% in 1.2N HCl at 100o/24hours and 68% in 0.67M KOH in BuOH at 118o/23hours [Kyba et al. J Am Chem Soc 95 2693 1973]. It has also been crystallised from *C6H6 (solubility is 1%) using Norite or aqueous EtOH after chromatography through silica gel, eluting with Me2CO/*C6H6. [Kyba et al. J Org Chem 42 4173 1977; see also Brussee & Jansen Tetrahedron Lett 24 3261 1983, Akimoto & Yamada Tetrahedron 27 5999 1971, Beilstein 6 IV 7020.] (S)-(-)-1,1'-Bi-2-naphthol Preparation Products And Raw materials Preparation Products

3.3 Usage: Chiral ligand.

4. Safety and Handling

4.1 Symbol: GHS06

4.1 Hazard Codes: T,Xi

4.1 Signal Word: Danger

4.1 Risk Statements: 25-36-36/37/38

4.1 Safety Statements: 26-45-24/25-36

4.1 Packing Group: III

4.1 Hazard Class: 6.1

4.1 Hazard Declaration: H301-H319

4.1 RIDADR: UN 2811 6.1/PG 3

4.1 Caution Statement: P301 + P310-P305 + P351 + P338

4.1 WGK Germany: 3

4.1 RTECS: DU3106100

4.1 Safety: Poison by ingestion and intraperitoneal routes. An eye irritant. When heated to decomposition it emits acrid smoke and fumes. See also various napthol entries.

4.2 Specification: Chiral binaphthol , its cas register number is 602-09-5. It also can be called 1,1'-Bi-2-naphthol ; 2,2'-Dihydroxy-1,1'-binaphthalene ; 2,2'-Dihydroxybinaphthalene ; Bis-beta-naphthol ; alpha-Binaphthyl-2,2'-diol and beta-Binaphthol .When heated to decomposition it emits acrid smoke and fumes. And Chiral binaphthol (CAS NO.602-09-5) wiil cause eye irritant.

4.3 Toxicity

1.	eye-rbt 50 mg MOD	DCTODJ Drug and Chemical Toxicology. 8 (1985),451.
2.	orl-rat LD50:113 mg/kg	DCTODJ Drug and Chemical Toxicology. 8 (1985),451.
3.	ipr-rat LD50:20 mg/kg	DCTODJ Drug and Chemical Toxicology. 8 (1985),451.
4.	ipr-mus LD50:6 mg/kg	DCTODJ Drug and Chemical Toxicology. 8 (1985),451.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301 Toxic if swallowed H319 Causes serious eye irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

18531-99-2Total: 45 Synthesis Route

135-19-3 327 Suppliers

18531-99-2 242 Suppliers

Literatures:
Takizawa, Shinobu; Rajesh, Doss; Katayama, Tomomi; Sasai, Hiroaki Synlett, 2009 , # 10 p. 1667 - 1669
Yield: ~98%

602-09-5 176 Suppliers

18531-99-2 242 Suppliers

Literatures:
Hu, Gang; Holmes, Daniel; Gendhar, Brina Fay; Wulff, William D. Journal of the American Chemical Society, 2009 , vol. 131, # 40 p. 14355 - 14364
Yield: ~96%

573-97-7 68 Suppliers

18531-99-2 242 Suppliers

Literatures:
Angewandte Chemie, , vol. 106, # 18 p. 1962 - 1964
Yield: null

View all

7. Precursor and Product

precursor:

76373-11-0

78265-35-7

77196-14-6

79044-27-2

80409-66-1

78265-10-8

602-09-5

93530-92-8

3401-47-6

80317-64-2

80373-29-1

135-19-3

75640-87-8

51439-63-5

573-97-7

883-21-6

20717-79-7

80317-59-5

80317-69-7

129647-55-8

93531-00-1

18531-96-9

View all

product :

75640-87-8

13185-00-7

18531-94-7

128544-06-9

39648-74-3

602-09-5

75640-70-9

173831-50-0

8. Other Information

8.0 Merck: 14,1226

8.1 BRN: 3592999

8.2 Chemical Properties: white to light yellow crystal powde

8.3 Uses: Chiral ligand.

8.4 Purification Methods: Dissolve it in cold 2.5N NaOH, extract with CH2Cl2, and acidify with 5% HCl. Collect the white precipitate and recrystallise it from aqueous EtOH and dry it in a vacuum [Akimoto & Yamada Tetrahedron 27 5999 1971]. It is optically stable in dioxane-water (100o/24hours). Racemisation: 72% in 1.2N HCl at 100o/24hours and 68% in 0.67M KOH in BuOH at 118o/23hours [Kyba et al. J Am Chem Soc 95 2693 1973]. It has also been crystallised from *C6H6 (solubility is 1%) using Norite or aqueous EtOH after chromatography through silica gel, eluting with Me2CO/*C6H6. [Kyba et al. J Org Chem 42 4173 1977; see also Brussee & Jansen Tetrahedron Lett 24 3261 1983, Akimoto & Yamada Tetrahedron 27 5999 1971, Beilstein 6 IV 7020.]

8.5 Uses

(S)-BINOL ligand in combination with titanium(IV) isopropoxide, forms (S)-(-)-BINOL-Ti complex, which is an effective chiral catalyst for:

asymmetric addition of alkynylzinc to unactivated ketones
enantioselective ring-opening reaction of meso-stilbene oxide and cyclohexene oxide with anilines
asymmetric aryl transfers from triaryl(tetrahydrofuran)aluminum reagents to a wide variety of ketones

It can also react with zirconium(IV) isopropoxide isopropanol complex to form a chiral Lewis acid catalyst for the facile enantioselective allylation of aldehydes by allyltributyltin.

9. Computational chemical data

Molecular Weight: 286.32g/mol
Molecular Formula: C₂₀H₁₄O₂
Compound Is Canonicalized: True
XLogP3-AA: 5.3
Exact Mass: 286.099379685
Monoisotopic Mass: 286.099379685
Complexity: 346
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 40.5
Heavy Atom Count: 22
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccB4MAAAAAAAAAAAAAAAAAAAAAAAAAAwYMGAAAAAAADBVAAAGgAACAAADASAmAAwBsAAAgCAAiBCAAACAAAgIAAIiAAGCIgIJiKCERKAcAAkwBEImAfAwPAOoAADAAAYAABAAAYAADAAAAAAAAAAAA==

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