219897-38-8

• 常用中文名：(S)-(+)-1-(Alpha-氨基苄基)-2-萘酚
• 常用英文名：2-Naphthalenol,1-[(S)-aminophenylmethyl]-
• CAS号：219897-38-8
• 分子式：C₁₇H₁₅NO
• 分子量：249.30700
• 发布时间：2018-12-15 17:30:17
• 更新时间：2024-01-08 12:05:52

• (S)-1-(α-氨基苄基)-2-萘酚[(S)-Betti碱] 在有机合成中主要被用于不对称催化反应中的手性配体或者不对称合成中的手性辅助合成试剂。(S)-Betti碱在手性拆分中比它的对映体廉价，因此得到更广泛的应用。

  外消旋Betti碱的合成已经有近百年的历史，由于容易发生逆Mannich反应，因此直到1998年才再次被拆分。但是用该方法拆分的手性Betti碱没有应用方面的报道。

  手性Betti碱具有1,3-氨基-羟基结构，可以与金属离子形成稳定的六元环配合物。该试剂本身不是一个很好的手性配体，但是它的许多叔胺衍生物已经证明是非常优秀的手性配体，并用于金属离子催化的不对称反应。这些手性Betti碱的叔胺衍生物主要是通过直接拆分或者使用手性胺进行的Mannich反应来制备 (式1，式2)^[3~6]。

  

  最近文献报道了外消旋Betti碱在丙酮溶液中被高效动力学手性拆分的方法，(S)-Betti碱作为酒石酸盐可以定量地从反应体系中沉淀出来，(R)-Betti碱则同时被转化成为相应的缩酮衍生物。(S)-Betti碱酒石酸盐不仅是该试剂的一种安全储存方式，而且可以代替(S)-Betti碱直接参与反应 (式3)。

  

  该试剂与二羰基化合物发生缩合反应可以方便地构筑手性5~7元含氮环状结构。它可以发生手性苯基甘氨醇相似的反应，但具有下列明显的优势：(1) 该试剂是一个氨基酚化合物，具有更高的反应活性。(2) 该试剂的羟基直接与位阻很大的萘环相连，所以反应具有较高的立体选择性。该试剂与末端二醛发生缩合反应生成的嗪中间体既可以用于手性配体的合成 (式4)，也可以用于含有手性哌啶的天然产物的全合成 (式5)。

  

名称

• 中文名: (S)-(+)-1-(Alpha-氨基苄基)-2-萘酚
• 英文名: 1-[(S)-amino(phenyl)methyl]naphthalen-2-ol
• 英文别名: unii-690biu4wik

物化性质

• 沸点: 451.1ºC at 760mmHg
• 熔点: 133-137ºC
• 分子式: C₁₇H₁₅NO
• 分子量: 249.30700
• 闪点: 226.6ºC
• 精确质量: 249.11500
• PSA: 46.25000
• LogP: 4.29380
• 蒸汽压: 9.38E-09mmHg at 25°C
• 储存条件:

  密闭于4 ºC阴凉干燥环境中

• 稳定性:

  1.遵照规定使用和储存则不会分解。

  2.该试剂在游离胺状态下不稳定，会自动分解。一般以盐酸盐或者酒石酸盐的形式储存和使用。

• 分子结构:

  1、 摩尔折射率：无可用

  2、 摩尔体积（cm³/mol）：无可用

  3、 等张比容（90.2K）：无可用

  4、 表面张力（dyne/cm）：无可用

  5、 极化率：无可用

• 计算化学:

  1、 疏水参数计算参考值（XlogP）：3.9

  2、 氢键供体数量：2

  3、 氢键受体数量：1

  4、 可旋转化学键数量：2

  5、 拓扑分子极性表面积（TPSA）：47.9

  6、 重原子数量：19

  7、 表面电荷：1

  8、 复杂度：287

  9、 同位素原子数量：0

  10、 确定原子立构中心数量：1

  11、 不确定原子立构中心数量：0

  12、 确定化学键立构中心数量：0

  13、 不确定化学键立构中心数量：0

  14、 共价键单元数量：1

• 更多:

  1. 性状：白色粉末

  2. 密度（g/mL,25/4℃）：无可用

  3. 相对蒸汽密度（g/mL,空气=1）：无可用

  4. 熔点（ºC）：133-134

  5. 沸点（ºC,常压）：无可用

  6. 沸点（ºC,5.2kPa）：无可用

  7. 折射率：无可用

  8. 闪点（ºC）：无可用

  9. 比旋光度（º）：无可用

  10. 自燃点或引燃温度（ºC）：无可用

  11. 蒸气压（kPa,25ºC）：无可用

  12. 饱和蒸气压（kPa,60ºC）：无可用

  13. 燃烧热（KJ/mol）：无可用

  14. 临界温度（ºC）：无可用

  15. 临界压力（KPa）：无可用

  16. 油水（辛醇/水）分配系数的对数值：无可用

  17. 爆炸上限（%,V/V）：无可用

  18. 爆炸下限（%,V/V）：无可用

  19. 溶解性：不溶于水,溶于大多数有机溶剂。

MSDS

Name: (S)-(+)-1-(alpha-Aminobenzyl)-2-naphthol 98% Material Safety Data Sheet Synonym: (S)-Betti bas CAS: 219897-38-8 Section 1 - Chemical Product MSDS Name:(S)-(+)-1-(alpha-Aminobenzyl)-2-naphthol 98% Material Safety Data Sheet Synonym:(S)-Betti bas Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 219897-38-8 (S)-(+)-1-(alpha-Aminobenzyl)-2-naphth 98% unlisted Hazard Symbols: XI Risk Phrases: 36/37/38 Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Irritating to eyes, respiratory system and skin.Moisture sensitive. Potential Health Effects Eye: Causes eye irritation. Skin: Causes skin irritation. May be harmful if absorbed through the skin. Ingestion: May cause irritation of the digestive tract. May be harmful if swallowed. Inhalation: Causes respiratory tract irritation. May be harmful if inhaled. Chronic: Not available. Section 4 - FIRST AID MEASURES Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid. Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Ingestion: Get medical aid. Wash mouth out with water. Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Notes to Physician: Treat symptomatically and supportively. Section 5 - FIRE FIGHTING MEASURES General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. Section 6 - ACCIDENTAL RELEASE MEASURES General Information: Use proper personal protective equipment as indicated in Section 8. Spills/Leaks: Vacuum or sweep up material and place into a suitable disposal container. Section 7 - HANDLING and STORAGE Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Storage: Keep refrigerated. (Store below 4C/39F.) Store in a tightly closed container. Store in a dry area. Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 219897-38-8: Personal Protective Equipment Eyes: Not available. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure. Respirators: Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Powder Color: white to off-white Odor: Not available. pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: 133 - 137 deg C Autoignition Temperature: Not available. Flash Point: Not available. Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: 259 deg C Solubility in water: Insoluble. Specific Gravity/Density: Molecular Formula: C17H15NO Molecular Weight: 249.31 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Not available. Conditions to Avoid: Incompatible materials. Incompatibilities with Other Materials: Strong oxidizing agents, strong reducing agents. Hazardous Decomposition Products: Nitrogen oxides, carbon monoxide, carbon dioxide. Hazardous Polymerization: Has not been reported Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 219897-38-8 unlisted. LD50/LC50: Not available. Carcinogenicity: (S)-(+)-1-(alpha-Aminobenzyl)-2-naphthol - Not listed by ACGIH, IARC, or NTP. Section 12 - ECOLOGICAL INFORMATION Section 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations. Section 14 - TRANSPORT INFORMATION IATA Shipping Name: Not regulated. Hazard Class: UN Number: Packing Group: IMO Shipping Name: Not regulated. Hazard Class: UN Number: Packing Group: RID/ADR Shipping Name: Not regulated. Hazard Class: UN Number: Packing group: Section 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives Hazard Symbols: XI Risk Phrases: R 36/37/38 Irritating to eyes, respiratory system and skin. Safety Phrases: S 36 Wear suitable protective clothing. S 37/39 Wear suitable gloves and eye/face protection. WGK (Water Danger/Protection) CAS# 219897-38-8: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 219897-38-8 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 219897-38-8 is not listed on the TSCA inventory. It is for research and development use only. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

生态学数据: 通常对水是不危害的，若无政府许可，勿将材料排入周围环境。

安全

• 危害码 (欧洲): Xi: Irritant;
• 风险声明 (欧洲): R36/37/38
• 安全声明 (欧洲): 37/39-36
• 海关编码: 2922299090

合成路线

481-82-3 ~42% 219897-38-8

文献：Periasamy, Mariappan; Anwar, Shaik; Reddy, Meda Narsi Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009 , vol. 48, # 9 p. 1261 - 1273

135-19-3 ~% 219897-38-8

文献：Synthesis (Germany), , vol. 45, # 7 art. no. SS-2012-H0910-OP, p. 899 - 902

53983-77-0 ~% 219897-38-8

文献：Synthesis (Germany), , vol. 45, # 7 art. no. SS-2012-H0910-OP, p. 899 - 902

上下游产品

上游产品  3
481-82-3 135-19-3 53983-77-0
下游产品  1
219897-59-3

海关

海关编码	2922299090
中文概述	2922299090. 其他氨基(萘酚、酚)及醚、酯〔包括它们的盐, 但含有一种以上含氧基的除外〕. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:30.0%
申报要素	品名, 成分含量, 用途, 乙醇胺及其盐应报明色度, 乙醇胺及其盐应报明包装
Summary	2922299090. other amino-naphthols and other amino-phenols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%