乙酰扁桃酰氯 | 1638-63-7

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 乙酰扁桃酰氯
• 中文别名: O-乙酰氯化扁桃酸；乙酰基扁桃酰氯；1-(氯甲酰)苄基乙酸酯；0-乙酰基苦杏仁酸氯化物
• 英文名称: 2-acetoxy-2-phenylacetyl chloride
• 英文别名: O-acetyl mandelic acid chloride；2-Chloro-2-oxo-1-phenylethyl acetate；(2-chloro-2-oxo-1-phenylethyl) acetate
• CAS: 1638-63-7
• 化学式: C₁₀H₉ClO₃
• mdl: MFCD00000714
• 分子量: 212.633
• InChiKey: BERNQQVIUAZUHY-UHFFFAOYSA-N

物化性质

• 熔点：
  36°C
• 沸点：
  125-130 °C10 mm Hg(lit.)
• 密度：
  0.943 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 稳定性/保质期：
  避免与不相容的材料、湿空气或水接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S26,S27,S28,S36/37/39,S45
• 危险类别码：
  R34
• WGK Germany：
  3
• 海关编码：
  2915390090
• 危险品运输编号：
  UN 3265 8/PG 2
• 包装等级：
  III
• 危险类别：
  8
• 储存条件：
  密封储存，存放在阴凉干燥的库房中，并远离腐蚀区域。冷藏时温度应保持在4°C。

SDS

Name:	O-Acetylmandelic acid chloride 95% Material Safety Data Sheet
Synonym:	1-(Chloroformyl)benzyl acetate; 2-Acetoxy-2-phenylacetyl chloride
CAS:	1638-63-7

Section 1 - Chemical Product MSDS Name:O-Acetylmandelic acid chloride 95% Material Safety Data Sheet
Synonym:1-(Chloroformyl)benzyl acetate; 2-Acetoxy-2-phenylacetyl chloride

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1638-63-7	O-Acetylmandelic acid chloride	95	216-674-6

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye burns. Lachrymator (substance which increases the flow of tears). May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid immediately.
Skin:
In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Get medical aid immediately. Wash clothing before reuse.
Ingestion:
If swallowed, do NOT induce vomiting. Get medical aid immediately.
If victim is fully conscious, give a cupful of water. Never give anything by mouth to an unconscious person.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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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. Use water spray to keep fire-exposed containers cool. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
If water is the only media available, use in flooding amounts. Do NOT get water inside containers. Cool containers with flooding quantities of water until well after fire is out. In case of fire, use carbon dioxide or dry chemical.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation. Do not get water inside containers.

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Section 7 - HANDLING and STORAGE
Handling:
Keep container tightly closed. Do not get on skin or in eyes. Do not ingest or inhale. Use with adequate ventilation. Do not allow contact with water. Discard contaminated shoes. Keep from contact with moist air and steam.
Storage:
Keep container closed when not in use. Corrosives area. Keep refrigerated. (Store below 4C/39F.) Store protected from moisture.

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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# 1638-63-7: Personal Protective Equipment Eyes: Wear chemical splash goggles and face shield.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear, colorless to pale yellow
Odor: chlorine-like
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 125-130 deg C @ 10 mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 112 deg C ( 233.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: .9430 g/ml
Molecular Formula: CH3CO2CH(C6H5)COCl
Molecular Weight: 212.63

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Moisture, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents, strong bases, alcohols, moisture.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1638-63-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
O-Acetylmandelic acid chloride - 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: CORROSIVE LIQUID, N.O.S.*
Hazard Class: 8
UN Number: 1760
Packing Group: III
IMO
Shipping Name: CORROSIVE LIQUID, N.O.S.
Hazard Class: 8
UN Number: 1760
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE LIQUID, N.O.S.
Hazard Class: 8
UN Number: 1760
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 1638-63-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1638-63-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1638-63-7 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

纯度在95%以上的商品沸点为125-130℃（1.33kPa），相对密度为0.943，折光率为1.5140，闪点大于110℃。

用途

主要用于医药中间体的生产，用于半合成或全合成制取后马托品氢溴酸盐。

生产方法

由扁桃酸乙酰化反应得到乙酰基扁桃酸，再经氯化而得。具体步骤如下：在干燥回流装置中，放入相当于1份扁桃酸乙酰化所得的乙酰基扁桃酸（约1.29份），然后加入2.38份二氯亚砜，在60-65℃条件下反应2.5小时，反应过程中产生的氯化氢及二氧化硫气体将被排出。随后升温至60-70℃，减压回收过量的二氯亚砜。再加入无水苯1.8倍量，进行减压共沸蒸馏，以去除多余的二氯亚砜和乙酰氯，直至蒸馏温度逐渐升至80℃且不再有苯馏出时，再加无水苯1.2倍量，再次减压蒸馏，直至蒸馏温度达到90℃为止。最终得到淡黄色油状物，即为乙酰扁桃酰氯，其产量约为原料扁桃酸的1.44倍。

反应信息

• 作为反应物：
  描述：

  乙酰扁桃酰氯 在 sodium hydroxide 作用下， 以 氯仿 为溶剂， 生成 2-羟基-2-苯基-1-哌啶-1-基乙酮
  参考文献：
  名称：

  Freer, Andrew A.; Isaacs, Neil W.; Kirby, Gordon W., Journal of Chemical Research, Miniprint, 1996, # 2, p. 601 - 621

  摘要：

  DOI：
• 作为产物：
  描述：

  扁桃酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 乙酰扁桃酰氯
  参考文献：
  名称：

  新型丙酮酸脱氢酶激酶抑制剂的设计、合成与评价

  摘要：

  目的：目前的工作描述了作为丙酮酸脱氢酶激酶 (PDK) 抑制剂的新型化合物的合成和生物学评价。这些药物应该成为一种新的治疗方法，用于治疗通过控制血乳酸水平而改善的病症。方法：制备属于 N-(4-(N-烷基/芳烷基氨磺酰基)苯基)-2-甲基丙酰胺和 1,2,4-苯并噻二嗪 1,1-二氧化物的四个系列化合物，并作为 PDK 抑制剂进行评估。结果：新合成的 N-(4-(N-烷基/芳烷基氨磺酰基)苯基)-2-甲基丙酰胺在结构上与先前报道的参考化合物 4 和 5 相关，被发现是有效的 PDK 抑制剂（即 10d：IC50 = 41 nM）。1,2,4-苯并噻二嗪 1, 在 6 位带有 (甲基/三氟甲基)-丙酰胺部分的 1-二氧化物也被设计为 N-(4-(N-烷基/芳烷基氨磺酰基)苯基)-2-羟基-2- 的构象限制闭环类似物甲基丙酰胺。他们中的大多数被发现不如他们的开环类似物有效。有趣的是，4-位烃侧

  DOI：

  10.2174/1573406418666220819102627

文献信息

• Substituted pyrroloquinoxalinones and diones
  申请人：Eli Lilly and Company

  公开号：US04075206A1

  公开（公告）日：1978-02-21

  Substituted pyrroloquinoxalinones and diones, useful as anti-inflammatory and anti-thrombotic agents.

  取代吡咯喹喔喹啉酮和二酮，可用作抗炎和抗血栓药物。
• Asymmetrische Synthesen über heterocyclische Zwischenstufen, XVI. Enantioselektive Synthese von α-Alkyl-α-phenylglycinen durch Alkylieren von an C-6 chiral substituierten 3,6-Dihydro-3-phenyl-2H-1,4-oxazin-2-onen
  作者：Wolfgang Hartwig、Ulrich Schöllkopf

  DOI：10.1002/jlac.198219821105

  日期：1982.11.22

  Ausgehend von DL-Phenylglycin und (S)-2-Hydroxyalkansäuren 4 werden die 3,6-Dihydro-3-phenyl-2H-1,4-oxazin-2-one 3 aufgebaut, die an C-6 ein endocyclisches Chiralitätszentrum besitzen. Die Anionen 10 von 3 reagieren mit Alkylhalogeniden an C-3 mit guten chemischen Ausbeuten und mit 50 bis mehr als 95% d. e. (asymmetrische Induktion). Bei der Hydrolyse der Addukte 11 werden die 2-Hydroxyalkansäuren

  从DL-苯基甘氨酸和（S）-2-羟基链烷酸4开始，构建了3,6-二氢-3-苯基-2 H -1,4-恶嗪-2-酮3，它们的内环中心为C-6的手性。阴离子10的3与烷基卤化物反应，在C-3具有良好的化学产率，并用50至95％以上的德（不对称诱导）。在加合物11的水解过程中，释放出2-羟基链烷酸4和旋光的（S）-α-烷基-α-苯基甘氨酸14。
• Scavenger assisted combinatorial process for preparing libraries of amides, carbamates and sulfonamides
  申请人：ELI LILLY AND COMPANY

  公开号：EP0825164A2

  公开（公告）日：1998-02-25

  This invention relates to a novel solution phase process for the preparation of amide, carbamate, and sulfonamide combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.

  这项发明涉及一种用于制备酰胺、碳酸酯和磺酰胺组合库的新型溶液相过程。这些库在药物发现中具有实用价值，并用于形成新型检测套件的微孔板组件。
• [EN] HETEROCYCLIC INHIBITORS OF GLUTAMINASE<br/>[FR] INHIBITEURS HÉTÉROCYCLIQUES DE GLUTAMINASE
  申请人：CALITHERA BIOSCIENCES INC

  公开号：WO2013078123A1

  公开（公告）日：2013-05-30

  The invention relates to the heterocyclic compounds of Formula (I) as defined further herein, and pharmaceutical preparations thereof. The invention further relates to methods of treating cancer, immunological or neurological diseases using the heterocyclic compounds of the invention.

  本发明涉及式(I)定义的杂环化合物及其药物制剂。本发明进一步涉及使用本发明的杂环化合物治疗癌症、免疫性或神经疾病的方法。
• The Synthesis of Chiral α-Aryl α-Hydroxy Carboxylic Acids via RuPHOX-Ru Catalyzed Asymmetric Hydrogenation
  作者：Huan Guo、Jing Li、Delong Liu、Wanbin Zhang

  DOI：10.1002/adsc.201700846

  日期：2017.10.25

  A ruthenocenyl phosphino‐oxazoline‐ruthenium complex (RuPHOX−Ru) catalyzed asymmetric hydrogenation of α‐aryl keto acids has been successfully developed, affording the corresponding chiral α‐aryl α‐hydroxy carboxylic acids in high yields and with up to 97% ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 5000 S/C) and the resulting products can be transformed

  已成功开发了钌烯基膦基-恶唑啉-钌络合物（RuPHOX-Ru）催化的α-芳基酮酸不对称氢化反应，可提供高收率和ee高达97％的相应手性α-芳基α-羟基羧酸。该反应可以在相对较低的催化剂负载量（至多5000 S / C）下以克为单位进行，所得产物可以转化为几种手性结构单元，生物活性化合物和手性药物。