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[aR,(+)]-Dinaphthol

(R)-(+)-1,1'-Bi-2-naphthol

CAS: 18531-94-7

Molecular Formula: C20H14O2

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[aR,(+)]-Dinaphthol - Names and Identifiers

Name (R)-(+)-1,1'-Bi-2-naphthol
Synonyms (R)-(+)-Binol
[aR,(+)]-Dinaphthol
(R)-(+)-1,1'-Bi-2-na
R-(+)-1_Bi-2-naphthol
(R)-(+)-BI-2-NAPHTHOL
R-(+)-1,1'-Bi-2-Naphthol
(R)-(+)-1,1-Bi-2-Naphthol
(R)-(+)-1,1'-Bi-2-naphthol
(R)-(+)-1,1'-Bi(2-Naphthol)
[1,1'-Binaphthalene]-2,2'-Diol
(R)-[1,1']-Binaphth-2-ol, (R)-BINOL
(R)-(+)-1,1'-Binaphthalene-2,2'-Diol
[aR,(+)]-1,1'-Binaphthalene-2,2'-diol
(+)-2,2μ-Dihydroxy-1,1μ-dinaphthyl, (R)-(+)-1,1μ-Binaphthalene-2,2μ-diol, (R)-BINOL
CAS 18531-94-7
EINECS 606-048-4

[aR,(+)]-Dinaphthol - Physico-chemical Properties

Molecular FormulaC20H14O2
Molar Mass286.32
Density1.301
Melting Point215-218°C
Boling Point388.69°C (rough estimate)
Specific Rotation(α)35.5 º (c=1, THF)
Water SolubilityInsoluble in water. Solubility in THF within almost transparency). Soluble in dioxane 50 mg/mL.
Solubility dioxane: 50mg/mL, clear
AppearanceWhite crystalline powder
Colorwhite to off-white
Merck14,1226
BRN3616837
pKa8.29±0.50(Predicted)
Storage ConditionStore below +30°C.
Refractive Index36.0 ° (C=1, THF)
MDLMFCD00004068
Physical and Chemical PropertiesMelting point 205-211°C. The specific optical rotation was 35.5 ° (c = 1, THF).
UseFor the synthesis of a variety of Chiral Pharmaceutical Intermediates

[aR,(+)]-Dinaphthol - Risk and Safety

Risk CodesR25 - Toxic if swallowed
R36 - Irritating to the eyes
R36/37/38 - Irritating to eyes, respiratory system and skin.
Safety DescriptionS26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S24/25 - Avoid contact with skin and eyes.
S36 - Wear suitable protective clothing.
UN IDsUN 2811 6.1/PG 3
WGK Germany3
RTECSDU3106100
FLUKA BRAND F CODES10
TSCANo
HS Code29071590
Hazard Class6.1
Packing GroupIII
ToxicityLD50 orally in Rabbit: 113 mg/kg

[aR,(+)]-Dinaphthol - Reference Information

Preparation Commercially available racemic 1,1 '-bi-2-naphthol and commercially available (S)-proline are mixed in acetonitrile in a molar ratio of 1:1 (the amount of acetonitrile is 15 times the weight of racemic 1,1'-bi-2-naphthol), heated and refluxed for 3 hours, when it is cold to room temperature, white solids are precipitated, and white solids and acetonitrile filtrate are obtained by suction filtration. White solids are heated and dissolved with ethanol, naturally cooled to room temperature, let stand, and precipitate bulk colorless transparent crystals (molecular inclusion compound crystallization, Mp220-225 ℃,1HNMR(DMSO-d6):δ9.32(s,4H,disappearedafteradding D2O),7.85(d,J = 8.1Hz,8H),7.33(d,J = 9Hz,4H),7.25-7.14(m,8H),6.93(d,J = 8.1Hz,4H),3.66(t,J = 8.1Hz,1H),3.24-3.16(m,1H),3.05-2.96(m,1H),2.02-1.91(m,2H),1.80-1.66(m,2H).13CNMR(DMSO-d6):δ171.6,152.1,133.3,128.2,127.6,126.9,125.0,123.8,121.6,117.7,113.9,59.9,44.7,28.7,23.4.), suction filtration, at room temperature, the molecular inclusion compound is crystallized and added to the ethyl acetate-water two-phase system (the volume ratio of organic phase and water phase is 2:1) Stirred for 1 hour, liquid separation, aqueous phase is extracted with ether, organic phase is combined, organic phase is dried, evaporated and residue is recrystallized with toluene to obtain enantipurity (S)-1,1 '-bi-2-naphthol bulk crystal, total yield: 68%,100% ee,m.p.208-210 ℃;[α]D20 =-36.5(c1,inTHF).
After the aqueous phase is evaporated and concentrated to dry, recrystallized with ethanol to recover (S)-proline, yield: 92%.
acetonitrile filtrate is evaporated and concentrated to dry, the residue is extracted with ether, the ether extract is evaporated, and the evaporated residue is recrystallized twice in toluene to obtain enantiomeric R-1,1 '-bi-2-naphthol, with a total yield of 41%,100% ee,m.p.208-210 ℃;[α]D20 = +36.4(c1,inTHF).
Uses Used for the synthesis of a variety of chiral pharmaceutical intermediates
Used as a chiral reagent
Atropine isomeric diols have many uses: in the asymmetric selective reduction of ketones The ligand in the chiral titanium catalyst is used for stereoselective reactions, such as glyoxylic acid reaction and Diels-Alder reaction; used for catalyzing the asymmetric oxidation of sulfide to sulfoxide Chiral auxiliary in the reaction; chiral lanthanide trifluoromethanesulfonic acid is generated from binaphthol, which is used as a catalyst for asymmetric Diels-Alder reactions; binaphthol derivatives have recently been found to be used in asymmetric Claisen rearrangement reactions and asymmetric epoxidation reactions; these diols (BINAP-H) lithium aluminum hydride derivatives have been widely used in the reduction reaction of ketones; chiral binaphthol salt precursors, salts used in asymmetric reactions of olefin epoxidation
Last Update：2024-04-09 15:16:48
[aR,(+)]-Dinaphthol
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Featured ProductsSpot supply
Product Name: (|R|)-(+)-1,1'-Bi(2-naphthol) Visit Supplier Webpage Request for quotation
CAS: 18531-94-7
Tel: +86-18821248368
Email: Int06@meryer.com
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Wuhan UCchem Biotechnology Co., LTD
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Changsha Changtang import and Export Co., Ltd.
Product Name: (R)-(+)-1,1'-Bi-2-naphthol Request for quotation
CAS: 18531-94-7
Tel: +86 18942506900
Email: lilyqu@chemoway.com
Mobile: +86 18942506900
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Spot supply
Product Name: (R)-(+)-1,1'-Bi(2-naphthol) Visit Supplier Webpage Request for quotation
CAS: 18531-94-7
Tel: +86-400-900-4166
Email: product@acmec-e.com
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SKYRUN INDUSTRIAL CO.,LTD
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CAS: 18531-94-7
Tel: +86 0571-86722205
Email: sales@chinaskyrun.com
Mobile: +8618958170122
QQ: 2531159185 Click to send a QQ messageSend QQ message
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Shanghai Yuanye Bio-Technology Co., Ltd.
Multiple Specifications
Product Name: (R)-(+)-1,1′-Bi(2-naphthol) Visit Supplier Webpage Request for quotation
CAS: 18531-94-7
Tel: 18301782025
Email: 3008007409@qq.com
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View History
[aR,(+)]-Dinaphthol
methyl 7-hydroxy-1-naphthylcarbamate
(E)-4-壬烯醛
N-苄基-beta-丙氨酸乙酯
H-p-Chloro-D-Phe-OMe.HCl
阿魏酸哌嗪
2-methoxy-N-methylpyridine-3-carboxamide
2-苯氧基-1-苯乙醇
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