2-萘甲醇 | 1592-38-7

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-萘甲醇
• 中文别名: Β-萘甲醇；β-萘甲醇
• 英文名称: 2-Naphthalenemethanol
• 英文别名: naphthalen-2-ylmethanol；2-naphthylmethanol；2-naphthylcarbinol；2-naphthalenmethanol
• CAS: 1592-38-7
• 化学式: C₁₁H₁₀O
• 分子量: 158.2
• InChiKey: MFGWMAAZYZSWMY-UHFFFAOYSA-N

物化性质

• 熔点：
  79-81 °C (lit.)
• 沸点：
  178°C/12mmHg(lit.)
• 密度：
  0.9887 (rough estimate)
• 溶解度：
  可溶于乙腈（少许）、氯仿（少许）
• 稳定性/保质期：
  在常温常压下稳定，应避免与酸、醋酸酐及酸性氯化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  F,Xi,C
• 安全说明：
  S24/25
• 危险类别码：
  R11
• WGK Germany：
  3
• 海关编码：
  2906299090
• 危险品运输编号：
  NONH for all modes of transport
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥处。

SDS

Name:	2-Naphthalenemethanol 98% Material Safety Data Sheet
Synonym:	None Known
CAS:	1592-38-7

Section 1 - Chemical Product MSDS Name:2-Naphthalenemethanol 98% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1592-38-7	2-Naphthalenemethanol	98%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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.

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
In case of fire, use carbon dioxide, dry chemical powder or appropriate foam.

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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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 1592-38-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white to yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 79 - 81 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C11H10O
Molecular Weight: 158.20

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Acids, acid chlorides, acid anhydrides, oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1592-38-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Naphthalenemethanol - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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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
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 1592-38-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1592-38-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1592-38-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质：白色固体粉末，熔点为79-82℃。

用途：作为敏乐啶的中间体。

反应信息

• 作为反应物：
  描述：

  2-萘甲醇 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 100.0 ℃ 、202.66 kPa 条件下， 反应 24.0h， 以73%的产率得到2-甲基萘
  参考文献：
  名称：

  在没有额外碱的简单条件下，可回收的Pd / C催化羰基一步还原为烃

  摘要：

  分别用水合肼，氢气和甲酸铵开发了用于合成烃的羰基还原剂。简单的，温和和有效的条件进行了通过采用可回收利用Pd / C作为在100正常溶剂催化剂提供ö C和平稳地进行，以产生相应的产品具有良好到优异的产率的反应。并证明了克级反应和催化剂的循环利用。此外，已经提出了该机制。

  DOI：

  10.1016/j.tetlet.2019.151447
• 作为产物：
  描述：

  2-甲基萘 在 cytochrome P₄₅₀ monooxygenase enzyme CYP₁₀₁B₁ 作用下， 生成 2-萘甲醇
  参考文献：
  名称：

  取代的芳族烃的选择性氧化和脱开的观察通过由CYP101B1系统萘氧化期间氧化还原循环†

  摘要：

  细胞色素P450单加氧酶CYP101B1，来自Novosphingobium芳烃DSM12444有效且选择性地氧化了各种萘和联苯衍生物。甲基取代的萘是比乙基萘和萘本身更好的底物。用2-甲基萘获得单取代烷基萘的最高产物形成活性。烷基萘的氧化对苄基甲基或次甲基CH键具有区域选择性。来自1-和2-乙基萘氧化的产物是高度对映体选择性的，并且明显过量地产生了单个立体异构体。与1-和2-甲基萘相比，双取代的底物2,7-二甲基萘具有更高的产物形成活性。甲基取代的联苯也是比联苯更好的底物，并且具有与1-甲基萘相似的生物催化参数。CYP101B1催化的2-和3-甲基联苯的氧化对甲基CH键具有选择性。例外的是4-甲基联苯的周转量，它以4'-（4-甲基苯基）苯酚为主要产物（占70％），其余部分由4-联苯甲醇构成。药物分子双氯芬酸也被CYP101B1区域选择性氧化为4'-羟基双氯芬酸。带有萘的CYP101B1系统

  DOI：

  10.1039/c7cy00088j

文献信息

• B(C₆F₅)₃-Catalyzed Hydrodesulfurization Using Hydrosilanes – Metal-Free Reduction of Sulfides
  作者：Kodai Saito、Kazumi Kondo、Takahiko Akiyama

  DOI：10.1021/acs.orglett.5b01651

  日期：2015.7.2

  B(C6F5)3-catalyzed hydrodesulfurization of carbon–sulfur bonds was achieved using triethylsilane as the reducing agent. The corresponding products were obtained in good yields under mild reaction conditions. This protocol could be applied to the reduction of sulfides, including benzyl and alkyl sulfides and dithianes, with high chemoselectivities.

  使用三乙基硅烷作为还原剂，实现了B（C 6 F 5）3催化的碳硫键加氢脱硫。在温和的反应条件下以高收率获得了相应的产物。该方案可用于具有高化学选择性的硫化物的还原，包括苄基和烷基硫化物以及二噻烷。
• A Bifunctional Copper Catalyst Enables Ester Reduction with H₂: Expanding the Reactivity Space of Nucleophilic Copper Hydrides
  作者：Birte M. Zimmermann、Trung Tran Ngoc、Dimitrios-Ioannis Tzaras、Trinadh Kaicharla、Johannes F. Teichert

  DOI：10.1021/jacs.1c09626

  日期：2021.10.13

  activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered “soft” copper(I) hydrides to previously

  采用基于铜 (I)/NHC 配合物和胍有机催化剂的双功能催化剂，促进了以 H 2作为末端还原剂的催化酯还原成醇。这里采用的方法能够通过氢键同时活化酯，并从 H 2形成亲核的氢化铜 (I) ，从而导致氢化物催化转移到酯。由胍亚基介导的质子穿梭进一步促进了还原步骤。这种酯还原的双功能方法首次将通常认为的“软”氢化铜 (I) 的反应性转变为以前不反应的“硬”酯亲电子试剂，并为用催化剂和 H 2替代化学计量还原剂铺平了道路.
• Clean and selective oxidation of aromatic alcohols using silica-supported Jones’ reagent in a pressure-driven flow reactor
  作者：Charlotte Wiles、Paul Watts、Stephen J. Haswell

  DOI：10.1016/j.tetlet.2006.05.157

  日期：2006.7

  By exploiting the high surface to volume ratio obtained within continuous flow reactors, we are able to oxidise selectively an array of primary alcohols to either the aldehyde or carboxylic acid, depending on the flow rates employed, demonstrating a degree of reaction control unattainable in traditional stirred reactors.

  通过利用连续流动反应器中获得的高表面积体积比，我们能够根据所使用的流速将一系列伯醇选择性地氧化为醛或羧酸，证明了在传统搅拌条件下无法实现的反应控制程度反应堆。
• Selective aerobic oxidation of allylic and benzylic alcohols catalyzed by N-hydroxyindole and copper(I) chloride
  作者：Shu-Su Shen、Vita Kartika、Ying Shan Tan、Richard D. Webster、Koichi Narasaka

  DOI：10.1016/j.tetlet.2011.12.058

  日期：2012.2

  1-hydroxy-2-methyl-6-trifluoromethyl-1H-indole-3-carboxylate acted as a catalyst for the chemoselective aerobic oxidation of allylic and benzylic alcohols. A variety of primary and secondary allylic and benzylic alcohols were oxidized into the corresponding α,β-unsaturated carbonyl compounds in good yields without affecting non-allylic alcohols.

  在氯化铜（I）的存在下，1-羟基-2-甲基-6-三氟甲基-1 H-吲哚-3-羧酸叔丁酯用作烯丙基和苄基醇的化学选择性好氧氧化的催化剂。各种一次和二次烯丙基和苄基醇的被氧化成相应的α，β -以良好产率的不饱和羰基化合物在不影响非烯丙基醇。
• A general and practical oxidation of alcohols to primary amides under metal-free conditions
  作者：Xiao-Feng Wu、Muhammad Sharif、Jian-Bo Feng、Helfried Neumann、Anahit Pews-Davtyan、Peter Langer、Matthias Beller

  DOI：10.1039/c3gc40668g

  日期：——

  A general procedure for oxidation of both benzyl alcohols and alkyl alcohols to primary amides under catalyst free conditions has been developed. 34 examples of primary amides were produced from their corresponding alcohols in moderate to excellent yields. This is a practical procedure for primary amides synthesis; water and tert-butanol are the only by-products. A commercial drug, Piracetam, was prepared

  一般程序 氧化作用 两者 苄醇 和 烷基醇 到 伯酰胺 在下面 催化剂自由条件得到了发展。34个例子伯酰胺 是从它们对应的 酒类产量中等至优异。这是一个实际的程序伯酰胺 合成; 水 和 叔丁醇是唯一的副产品。商业广告药品， 拉西坦一步制备了，收率为73％。

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