(S)-(-)-2,2-Dihydroxy-1,1-Binaphthyl (S)-(-)-1,1-联-2-萘酚

CAS 18531-99-2 MFCD00004068

化学结构图

18531-99-2
SMILES: Oc1ccc2ccccc2c1-c1c(O)ccc2ccccc12

化学属性

Mol. FormulaHOC10H6C10H6OH
Mol. Weight286.32
Melting Point208-210
TSCANo
Density1.301
Solubilitydioxane: 50 mg/mL, clear
Appearance white to off-white pwdr.

别名和识别编码

Chemical Name(S)-(-)-2,2-Dihydroxy-1,1-Binaphthyl
CAS Number18531-99-2
Alfabeta NameBINAPHTHOL S112(())------,'
MDL NumberMFCD00004068
Synonym 1,1'-聯(2-萘酚) 联萘酚 (+)-2,2′-二羟基-1,1′-联萘 (R)-(+)-1,1′-联萘-2,2′-二醇 (R)-BINOL 2,2'-二羥-1,1'-聯萘 (S)-(-)-1,1′-联(2-萘酚) (R)-(+)-1,1′-联(2-萘酚) R-联萘酚 (±)-1,1′-联萘-2,2′-二醇 (±)-2,2′-二羟基-1,1′-联萘 (+/-)-1,1'-BI(2-NAPHTHOL) (S)-(-)-BINOL AURORA KA-7212 1,1′-联-2-萘酚 Bis-beta-naphthol (S)-(-)-1,1′-联萘-2,2′-二醇 2,2'-Dihydroxybinaphthalene (±)-1,1′-联萘-2,2′-二醇 (±)-2,2′-二羟基-1,1′-联萘 2,2'-Dihydroxybinaphthalene 2,2'-Dihydroxydinaphthyl 2,2'-Dinaphthol BINOL (-)-2,2′-二羟基-1,1′-联萘
PubChem Substance ID11762
Beilstein Registry Number4296068
Reaxys-RN997518
Merck Number14,1226
EC Number210-014-0
Chemical Name Translation(S)-(-)-1,1-联-2-萘酚
InChIKeyPPTXVXKCQZKFBN-UHFFFAOYSA-N
LabNetwork Molecule IDLN00009837
InChIInChI=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
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分类

  • Asymmetric Synthesis, BINOLs, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes
  • {SNA} Catalysis and Inorganic Chemistry, Chemical Synthesis, Other Ligands
  • {SNA} Asymmetric Synthesis, BINOLs, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes
  • {SNA} Building Blocks, Chemical Synthesis, Organic Building Blocks, Oxygen Compounds, Polyols

相关文献及参考

  • Merck: 14,1226
  • Forms a complex with lithium aluminum hydride, useful for the asymmetric reduction of ketones: J. Am. Chem. Soc., 101, 3129, 5843 (1979); alkynyl alcohols: Tetrahedron Lett., 22, 247 (1981); or steroidal enones: J. Chem. Soc., Chem. Commun., 115 (1981).
  • For diastereoselective alkyation of
  • The complex with diisopropoxytitanium dichloride catalyzes the "glyoxylate ene reaction", in which glyoxylate ester adds to alkenes in a highly stereospecific manner: J. Am. Chem. Soc., 111, 1940 (1989):
  • See also (R)-(+)-2,2'-Bis(diphenyl­phosphino)-1,1'-binaphthyl­, B23785.
  • Chiral precursor of various reagents used in enantioselective syntheses.
  • In combination with Titanium(IV)­ isopropoxide, A13703, catalyzes the asymmetric allylation of aldehydes using allylstannanes to give chiral homoallylic secondary alcohols: J. Am. Chem. Soc., 115, 8467 (1993). The same transformation has also been achieved using the dichlorotitanium complex: J. Am. Chem. Soc., 115, 7001 (1993).
  • See also (R)-(+)-2,2'-Bis(diphenyl­phosphino)-1,1'-binaphthyl­, B23785.
  • Used in combination with 2-Formyl­benzeneboronic acid, B25434 in a protocol for determining the enantiomeric excess of primary amines by NMR: Org. Lett., 8, 609
  • Merck: 14,1226 Beilstein:6,1051
  • Merck 14 ,1226
  • Forms a chiral boron-containing Lewis acid which has been used in asymmetric Diels-Alder reactions: Tetrahedron, 49, 1749 (1993); J. Am. Chem. Soc., 115, 1151 (1993).
  • For further example usingɑ-Methyl­styrene, L03609, see: Org. Synth. Coll., 9, 596 (1998).

安全信息

Warnings IRRITANT
GHS Symbol
WGK Germany3
Hazard statements
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H301 Toxic if swallowed 吞食有毒
Personal Protective Equipment Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes T
RTECSDU3106100
Precautionary statements
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • P301+P310+P330
  • P302+P352+P332+P313+P362+P364
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P305+P351+P338+P337+P313
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • P332+P313
  • P301+P310
  • P308+P313
  • P302+P350
Signal word
UN Number UN 2811 6.1/PG 3
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
  • S37/39 Wear suitable gloves and eye/face protection 穿戴适当的手套和眼睛/面保护；
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R25 Toxic if swallowed 吞咽有毒
  • R36 Irritating to eyes 刺激眼睛
Packing GroupIII
Hazard Class6.1
Storage condition 2-8°C 
TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 42 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AECTCV Archives of Environmental Contamination and Toxicology.
   (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ
   070944)  V.1-    1973-  Volume(issue)/page/year: 14,111,1985

其他信息

  • 可燃性危险特性:可燃; 燃烧产生刺激烟雾
  • 储运特性:通风低温干燥; 与库房食品原料分开存放
  • 存储注意事项:湿度敏感;氮气保护
  • Sigma Aldrich:602-09-5(sigmaaldrich)
  • 不溶于水，微溶于醋酸和乙醇。
  • MSDS 信息:2,2'-Dihydroxy-1,1'-binaphthyl(602-09-5).msds
  • 海关编码:29072900
  • 毒性分级:高毒
  • 1,1'-联-2-萘酚价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 B0461 1,1'-联-2-萘酚 1,1'-Bi-2-naphthol 5G 366元 2014/06/02 B0461 1,1'-联-2-萘酚 1,1'-Bi-2-naphthol 25G 995元 2010/06/21 147350050 1,1'-联-2-萘酚 1,1'-Bi-2-naphthol 99% 5 GR 388元
  • 图谱信息:1,1'-联-2-萘酚(602-09-5)核磁图( 13 CNMR) 1,1'-联-2-萘酚(602-09-5)红外图谱(IR2) 1,1'-联-2-萘酚(602-09-5)核磁图( 1 HNMR) 1,1'-联-2-萘酚(602-09-5)红外图谱(IR1) 1,1'-联-2-萘酚(602-09-5)质谱(MS)
  • 检测方法:HPLC
  • MOL 文件:602-09-5.mol
  • TCI Shanghai:1,1'-联-2-萘酚 1,1'-Bi-2-naphthol,>;99.0%(GC)(602-09-5)
  • Acros Organics:1,1'-联-2-萘酚 1,1'-Bi-2-naphthol, 99%(602-09-5)
  • F:10
  • 用途一:手性拆分剂，广泛用于手性液晶,药物,香料,农药的手性合成。
  • 类别:有毒物品
  • 急性毒性:口服-小鼠 LDL0: 42 毫克/公斤
  • 下游产品:1,1'-联萘-2,2'-双二苯膦 --> 联萘二溴
  • 灭火剂:干粉,泡沫,沙土,二氧化碳, 雾状水
  • Alfa Aesar:(±)-1,1-联萘酚,99% (+/-)-1,1'-Bi(2-naphthol), 99%(602-09-5)

系列性分类

  1. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  1. Chemical Synthesis 化学合成
  2. Catalysis and Inorganic Chemistry 催化剂和无机化学
  3. Other Ligands - Catalysis and Inorganic Chemistry
  1. Chemical Synthesis 化学合成
  2. Catalysis and Inorganic Chemistry 催化剂和无机化学
  3. Other Ligands - Catalysis and Inorganic Chemistry
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Oxygen Compounds 氧化合物
  5. Phenols 酚类
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Oxygen Compounds 氧化合物
  5. Protected Alcohols/Phenols - Oxygen Compounds
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Oxygen Compounds 氧化合物
  5. Polyols - Oxygen Compounds
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Oxygen Compounds 氧化合物
  5. Polyols - Oxygen Compounds
  1. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  3. Chiral Catalysts, Ligands, and Reagents - Asymmetric Synthesis
  4. Privileged Ligands and Complexes - Chiral Catalysts, Ligands, and Reagents
  5. BINOLs - Privileged Ligands and Complexes
  1. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  3. Chiral Catalysts, Ligands, and Reagents - Asymmetric Synthesis
  4. Privileged Ligands and Complexes - Chiral Catalysts, Ligands, and Reagents
  5. BINOLs - Privileged Ligands and Complexes
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Oxygen Compounds 氧化合物
  5. Phenols
  1. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  3. Chiral Catalysts, Ligands, and Reagents - Asymmetric Synthesis
  4. Privileged Ligands and Complexes
  5. BINAPs
  1. Chemical Synthesis 化学合成
  2. Catalysis and Inorganic Chemistry 催化剂和无机化学
  3. Osmium
  1. BINOL
  2. Oxygen

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