3-氯甲基苯甲酸甲酯 | 34040-63-6

• 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: 3-氯甲基苯甲酸甲酯
• 中文别名: 间氯甲基苯甲酸甲酯；3-(氯甲基L)-苯甲酸甲基酯
• 英文名称: methyl 3-(chloromethyl)benzoate
• CAS: 34040-63-6
• 化学式: C₉H₉ClO₂
• mdl: MFCD00157184
• 分子量: 184.622
• InChiKey: NEXHXAMAIMAABX-UHFFFAOYSA-N

物化性质

• 沸点：
  148-160 °C(Press: 21 Torr)
• 密度：
  1.19g/ml

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 3-(chloromethyl)benzoate
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Methyl 3-(chloromethyl)benzoate
CAS number: 34040-63-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C9H9ClO2
Molecular weight: 184.6

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen chloride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-氯甲基苯甲酸甲酯 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 methyl 2-[(3-methoxycarbonylphenyl)methylsulfanyl]benzoate
  参考文献：
  名称：

  El-Bardan, Ali A.; Gohar, Gamal A.; El-Zahraa, Fatma, Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 69, # 12, p. 147 - 152

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(氯甲基)苯甲酰氯 在 三乙胺 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 生成 3-氯甲基苯甲酸甲酯
  参考文献：
  名称：

  Prodrugs of inhibitors of farnesyl-protein transferase

  摘要：

  本发明涵盖了包含适当取代的氨基烷基苯甲酰基团的肽类似化合物。这些化合物抑制了法尼基蛋白转移酶酶和某些蛋白质的法尼醇化。此外，这些法尼基蛋白转移酶抑制剂与先前描述的抑制法尼基蛋白转移酶的抑制剂不同，因为它们没有硫醇基团。缺乏硫醇基团在改善动物的药代动力学行为、预防硫醇依赖性化学反应（如快速自氧化和与内源硫醇形成二硫键）以及减少全身毒性方面提供了独特的优势。本发明还包括含有这些法尼醇转移酶抑制剂的化疗组合物和其生产方法。

  公开号：

  US05534537A1

文献信息

• <i>N</i>-Hydroxyphthalimide/benzoquinone-catalyzed chlorination of hydrocarbon C–H bond using <i>N</i>-chlorosuccinimide
  作者：Zi-Hao Li、Béla Fiser、Biao-Lin Jiang、Jian-Wei Li、Bao-Hua Xu、Suo-Jiang Zhang

  DOI：10.1039/c9ob00216b

  日期：——

  The direct chlorination of C–H bonds has received considerable attention in recent years. In this work, a metal-free protocol for hydrocarbon C–H bond chlorination with commercially available N-chlorosuccinimide (NCS) catalyzed by N-hydroxyphthalimide (NHPI) with 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ) functioning as an external radical initiator is presented. Aliphatic and benzylic substituents

  近年来，CH键的直接氯化反应受到了广泛的关注。在这项工作中，对烃的C-H键氯化不含金属的协议与市售Ñ氯琥珀酰亚胺（NCS）通过催化Ñ提出了具有2,3-二氰基5,6-二氯苯醌（DDQ）作为外部自由基引发剂的-羟基邻苯二甲酰亚胺（NHPI）。发现脂族和苄基取代基以及杂芳族取代基具有良好的耐受性。实验和理论分析均表明该反应经历了其中NHPI充当催化剂而不是引发剂的过程。另一方面，由PINO物种而不是高反应性N中心自由基进行的C–H键的氢提取使该方案获得的一氯化的高化学选择性合理化，因为后者对C具有反应性（sp 3）–一氯化物的H键。目前的结果有望为进一步开发用于脂肪族和苄基烃CH的高度选择性官能化的硝氧基自由基体系提供希望。
• Bicyclic nitrogen heterocycles
  申请人：Hoffmann-La Roche Inc.

  公开号：US06150373A1

  公开（公告）日：2000-11-21

  Amino-substituted dihydropyrimido[4,5-d]pyrimidinones of the formula in which R.sup.1 represents hydrogen, lower alkyl, aryl, aryl-lower alkyl, heteroaryl, heteroaryl-lower alkyl, lower cycloalkyl or lower cycloalkyl-lower alkyl, R.sup.2 represents lower alkyl, aryl, aryl-lower alkyl, heteroaryl, heteroaryl-lower alkyl, lower cycloalkyl or lower cycloalkyl-lower alkyl, and R.sup.3 represents hydrogen, lower alkyl, aryl, aryl-lower alkyl, heteroaryl, heteroaryl-lower alkyl, lower cycloalkyl, lower cycloalkenyl or lower cycloalkyl-lower alkyl, and pharmaceutically acceptable salts thereof are protein kinase inhibitors. They can be used in the treatment or prophylaxis of inflammatory, immunological, oncological, bronchopulmonary, dermatological and cardiovascular disorders, in the treatment of asthma, central nervous system disorders or diabetic complications or for the prevention of graft rejection following transplant surgery.

  氨基取代的二氢嘧啶[4,5-d]嘧啶酮的公式，其中R.sup.1代表氢，低级烷基，芳基，芳基-低级烷基，杂芳基，杂芳基-低级烷基，低级环烷基或低级环烷基-低级烷基，R.sup.2代表低级烷基，芳基，芳基-低级烷基，杂芳基，杂芳基-低级烷基，低级环烷基或低级环烷基-低级烷基，R.sup.3代表氢，低级烷基，芳基，芳基-低级烷基，杂芳基，杂芳基-低级烷基，低级环烷基，低级环烯基或低级环烷基-低级烷基，以及药用可接受的盐，它们是蛋白激酶抑制剂。它们可用于治疗或预防炎症、免疫、肿瘤、支气管肺、皮肤和心血管疾病，在治疗哮喘、中枢神经系统疾病或糖尿病并发症，或用于预防移植手术后的移植物排斥反应。
• Correlation of carbon-13 substituent-induced chemical shifts:Meta- andpara-substituted methyl benzoates
  作者：Miloš Buděšńský、Otto Exner

  DOI：10.1002/mrc.1260270612

  日期：1989.6

  Carbon‐13 NMR spectra are reported for 69 substituted methyl benzoates in deuteriochloroform or in its mixture with dimethyl sulphoxide‐d6. The substituent‐induced chemical shifts (SCS) of the CO carbon correlate poorly with dual substituent parameters (DSP) in all possible modifications, and for meta derivatives in particular this correlation is both overpara meterized and imprecise. A much better

  69 取代的苯甲酸甲酯在氘代氯仿中或其与二甲基亚砜-d6 的混合物中的碳 13 NMR 谱报告。在所有可能的修饰中，CO 碳的取代基诱导化学位移 (SCS) 与双取代基参数 (DSP) 的相关性很差，特别是对于间位衍生物，这种相关性既过度参数化又不精确。先前通过主成分分析 (PCA) 从更大的集合中导出的参数（指定为 Bm、Bp 和 Cp）获得了更好的相关性。CH3 碳的 SCS 与原始的简单哈米特方程非常相关，不需要 DSP 处理。在如此大的集合中，取代基的聚类并不重要。
• Visible Light-Catalyzed Benzylic C–H Bond Chlorination by a Combination of Organic Dye (Acr⁺-Mes) and <i>N</i>-Chlorosuccinimide
  作者：Ming Xiang、Chao Zhou、Xiu-Long Yang、Bin Chen、Chen-Ho Tung、Li-Zhu Wu

  DOI：10.1021/acs.joc.0c01000

  日期：2020.7.17

  By combining “N-chlorosuccinimide (NCS)” as the safe chlorine source with “Acr+-Mes” as the photocatalyst, we successfully achieved benzylic C–H bond chlorination under visible light irradiation. Furthermore, benzylic chlorides could be converted to benzylic ethers smoothly in a one-pot manner by adding sodium methoxide. This mild and scalable chlorination method worked effectively for diverse toluene

  通过将作为安全氯源的“ N-氯琥珀酰亚胺（NCS）”与作为光催化剂的“ Acr + -Mes”相结合，我们在可见光照射下成功实现了苄基C–H键氯化。此外，通过加入甲醇钠可以一锅法将苄基氯平稳地转化为苄基醚。这种温和且可扩展的氯化方法可有效地用于多种甲苯衍生物，尤其是对于缺电子的底物。仔细的机理研究表明，NCS提供了一个氢抽象剂“ N-中心的琥珀酰亚胺基”，该基团依赖于Acr • -Mes的还原能力来裂解苄基的C–H键。
• Silver-Catalyzed C(sp³)–H Chlorination
  作者：Jun Ozawa、Motomu Kanai

  DOI：10.1021/acs.orglett.7b00367

  日期：2017.3.17

  A silver-catalyzed chlorination of benzylic, tertiary, and secondary C(sp3)–H bonds was developed. The reaction proceeded with as low as 0.2 mol % catalyst loading at room temperature under air atmosphere with synthetically useful functional group compatibility. The regioselectivity and reactivity tendencies suggest that the chlorination proceeded through a radical pathway, but an intermediate alkylsilver

  开发了银催化的苄基，叔和仲C（sp 3）-H键的氯化反应。反应在室温下在空气气氛下以低至0.2mol％的催化剂负载量进行，具有合成上有用的官能团相容性。区域选择性和反应性趋势表明氯化是通过自由基途径进行的，但是不能排除中间的烷基银物种。