N-羟甲基-3,4,5,6-四氢邻苯二甲酰亚胺 | 4887-42-7

• 物质功能分类: 化学农药原药 - 杀虫剂中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: N-羟甲基-3,4,5,6-四氢邻苯二甲酰亚胺
• 中文别名: N-羟甲基-3,4,5,6-四氢酞亚胺；N-羟甲基-四羟基邻苯二胺
• 英文名称: N-hydroxymethyl-3,4,5,6-tetrahydrophthalimide
• 英文别名: N-methyloltetrahydrophthalimide；N-hydroxymethyl-3,4,5,6-tetrahydrophthalamide；N-hydroxymethyl-3,4,5,6-tetrahydroimine；alcohol of tetramethrin；2-hydroxymethyl-4,5,6,7-tetrahydro-isoindole-1,3-dione；3,4,5,6-tetrahydro-N-(hydroxymethyl)phthalimide；N-Hydroxymethyl-3,4,5,6-tetrahydro-phthalimid；3,4,5,6-tetrahydro-phthalimidomethyl alcohol；3,4,5,6-tetrahydrophthalimido-mehtyl alcohol；N-(3,4,5,6-tetrahydrophthalimide)-methylalcohol；3,4,5,6-tetrahydrophthalimidomethylol；2-(hydroxymethyl)-4,5,6,7-tetrahydroisoindole-1,3-dione
• CAS: 4887-42-7
• 化学式: C₉H₁₁NO₃
• mdl: MFCD00051728
• 分子量: 181.191
• InChiKey: QQHOVRKETYPQHY-UHFFFAOYSA-N

物化性质

• 熔点：
  81-85 °C(lit.)
• 沸点：
  314.29°C (rough estimate)
• 密度：
  1.2375 (rough estimate)
• 稳定性/保质期：
  避免与不相容的材料接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 储存条件：
  密封存储，应存放于阴凉干燥的仓库中。

SDS

Name:	N-Hydroxymethyl-3,4,5,6-Tetrahydrophthalimide, 98% Material Safety Data Sheet
Synonym:	None Known.
CAS:	4887-42-7

Section 1 - Chemical Product MSDS Name: N-Hydroxymethyl-3,4,5,6-Tetrahydrophthalimide, 98% Material Safety Data Sheet
Synonym: None Known.

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4887-42-7	N-Hydroxymethyl-3,4,5,6-Tetrahydrophth	98%	225-500-8

Hazard Symbols: XI
Risk Phrases: 36/37/38

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SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Irritating to eyes, respiratory system and skin. Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation. Inhalation may be fatal as a result of spasm, inflammation, edema of the larynx and bronchi, chemical pneumonitis and pulmonary edema. May cause burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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SECTION 4 - FIRST AID MEASURES
Eyes:
Immediately 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. Do NOT use mouth-to-mouth resuscitation.
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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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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:
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. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 4887-42-7: 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: Crystalline powder
Color: slightly yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 80-84 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: C9H11NO3
Molecular Weight: 181.0819

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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:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Acid anhydrides, acid chlorides, acids, oxidizing agents, carbon dioxide.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 4887-42-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-Hydroxymethyl-3,4,5,6-Tetrahydrophthalimide - 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 Not regulated as a hazardous material. IMO Not regulated as a hazardous material. 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 37/39 Wear suitable gloves and eye/face protection. WGK (Water Danger/Protection) CAS# 4887-42-7: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 4887-42-7 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 4887-42-7 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 2/01/2000 Revision #3 Date: 3/04/2004 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质 本品为无色结晶或稍具绿黄色结晶，熔点80～82℃，相对密度1.4600，微溶于水，易溶于苯、氯仿、二氯乙烷、乙醇、甲苯等有机溶剂，难溶于石油醚。

用途 N-羟甲基-3,4,5,6-四氢邻苯二甲酰亚胺（简称胺醇）是卫生用杀虫剂胺菊酯的重要中间体。

生产方法 胺醇的制备首先由丁二烯与顺丁二酸酐通过Diels-Alder反应生成1,2,3,6-四氢邻苯二甲酸酐（简称四氢苯酐或△⁴），再经异构化得到3,4,5,6-四氢邻苯二甲酸酐（简称△¹），最后由△¹通过氨化、羟甲基化而制得。

具体步骤如下：在反应器中加入3,4,5,6-四氢邻苯二甲酰亚胺、37％甲醛溶液和稀氢氧化钠溶液，以二氯乙烷为溶剂进行搅拌加热回流。冷却分层后进行后处理，并通过减压蒸馏得到黏稠状的粗胺醇；再用甲苯重结晶，可得到纯度为97%的精胺醇。

反应信息

• 作为反应物：
  描述：

  N-羟甲基-3,4,5,6-四氢邻苯二甲酰亚胺 、 10-羟基喜树碱 在 硫酸 作用下， 反应 12.0h， 以90%的产率得到(19S)-8-[(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
  参考文献：
  名称：

  新型亲脂性 9-取代喜树碱衍生物的半合成、细胞毒活性和口服有效性

  摘要：

  尽管 9 取代的喜树碱在癌症治疗中是有希望的候选者，但该位置的有限可及性已将这些衍生物的研究减少到一些标准修改。我们在此报告了一种基于 Tscherniac-Einhorn 反应的新型半合成路线，以合成在第 9 位具有酰胺甲基和酰亚胺甲基取代的新的亲脂性喜树碱衍生物。评估了化合物的抗增殖活性、拓扑异构酶 I 抑制和口服可用性。初步数据表明，相对于拓扑替康，大体积的亚氨基甲基修饰是有效口服给药的合适亲脂性替代物。此外，该通用程序为获得新的喜树碱衍生物铺平了道路。

  DOI：

  10.1021/ml400125z
• 作为产物：
  描述：

  N-羟甲基邻苯二甲酰亚胺 在 platinum on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 105.0~110.0 ℃ 、1.8 MPa 条件下， 反应 12.0h， 以93.7%的产率得到N-羟甲基-3,4,5,6-四氢邻苯二甲酰亚胺
  参考文献：
  名称：

  一种N-羟甲基-3,4,5,6-四氢邻苯二甲酰亚胺的合成方法

  摘要：

  本发明公开了一种N‑羟甲基‑3,4,5,6‑四氢邻苯二甲酰亚胺的合成方法，将邻苯二甲酰亚胺、四丁基溴化铵加入到水中，加毕滴加甲醛水溶液，滴毕保温反应，反应结束后脱干溶剂以丙酮水溶液重结晶，重结晶后料投入高压釜后加入Pd/C,通氢气保温保压反应，反应结束后脱干溶剂以甲苯重结晶，该方法的两步合成收率可达到80％以上，产品液谱归一含量可达到97.6％。该方法中使用的溶剂经回收处理后可套用于反应系统内，还原催化剂可套用10次以上，本发明工艺过程简单，易操作、反应选择性强，产品收率、质量，能耗低、无含磷、含氮废水产生，生产现场环境得到显著改善，有利于工业化清洁生产。

  公开号：

  CN112939843B

文献信息

• Method for producing cyclopropanecarboxylates
  申请人：——

  公开号：US20020052525A1

  公开（公告）日：2002-05-02

  There is provided a method for producing a cyclopropanecarboxylate of formula (1): 1 which comprises contacting a cyclopropanecarboxylate of formula (2): 2 with a monohydroxy compound of formula (3): R 7 OH  (3) in the presence of a lithium compound of formula (4): R 8 OLi  (4), wherein R 1 , R 2 , R 3 , R 4 and R 5 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group; R 6 represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted phenyl group; R 7 and R 8 do not simultaneously represent the same and each independently represent a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

  提供了一种生产公式（1）环丙烷甲酸酯的方法： 1 该方法包括接触 一种公式（2）的环丙烷甲酸酯： 2 与一种公式（3）的单羟基化合物： R 7 OH  (3) 在公式（4）的锂化合物存在下： R 8 OLi  (4)， 其中R 1 ，R 2 ，R 3 ，R 4 和R 5 每个独立代表 一个氢原子，一个卤素原子， 一个取代或不取代的烷基团， 一个取代或不取代的烯丙基团，或 一个取代或不取代的芳基团； R 6 代表一个有1到10个碳原子的烷基团或 一个取代或不取代的苯基团； R 7 和R 8 不同时代表相同的，且每个独立代表 一个取代或不取代的烷基团，或 一个取代或不取代的芳基团。
• Process for producing cyclopropanecarboxylates
  申请人：——

  公开号：US20020151741A1

  公开（公告）日：2002-10-17

  There is disclosed a process process for producing a cyclopropanecarboxylate of formula (1): 1 which process comprises reacting cyclopropanecarboxylic acid of formula (2): 2 with a monohydroxy compound of formula (3): R 6 OH  (3), in the presence of a catalyst compound comprising an element of to Group 4 of the Periodic Table of Elements.

  披露了一种制备公式(1)所示的环丙烷甲酸酯的方法：1该方法包括将公式(2)所示的环丙烷甲酸与公式(3)所示的单一羟基化合物反应：R6OH  (3)，在含有元素周期表第4族元素的催化剂化合物存在下。
• Process for Producing 3-(2-Cyano-1-propenyl)-2,2- Dimethylcyclopropanecarboxylic Acid or Salt Thereof
  申请人：Uekawa Toru

  公开号：US20120016150A1

  公开（公告）日：2012-01-19

  A process for producing comprising reacting a 3-formyl-2,2-dimethylcyclopropanecarboxylate and propionitrile in the presence of a base to obtain 3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid or its salt.

  生产过程包括在碱的存在下，通过将3-甲酰基-2,2-二甲基环丙基羧酸酯和丙腈反应，得到3-(2-氰丙烯基)-2,2-二甲基环丙基羧酸或其盐。
• [EN] ESTER DERIVATIVES OF (PYRIDINYLOXY-PHENYL)-METHANOL AND PROCESS OF PREPARATION THEREOF<br/>[FR] DERIVES ESTERS DE (PYRIDINYLOXY-PHENYL)-METHANOL ET LEUR PROCEDE DE PREPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2004087667A1

  公开（公告）日：2004-10-14

  The present invention relates to novel pyridinyloxy phenyl methanol derivatives of the formula (III) with X=(a) or (b), obtained by the reaction of 4-/3-(3,5,6-pyridinyl-2-oxy)phenylmethanol and 4-/3-(2,3,5,6-pyridinyl-4-oxy)phenyl methanol with the acid chloride.

  本发明涉及具有以下结构的新型吡啶氧基苯甲醇衍生物（III）：X =（a）或（b），通过4-/3-(3,5,6-吡啶基-2-氧基)苯甲醇和4-/3-(2,3,5,6-吡啶基-4-氧基)苯甲醇与酸氯反应而得到。
• Process for the preparation of carboxylic acid esters
  申请人：Souda Hiroshi

  公开号：US20050113581A1

  公开（公告）日：2005-05-26

  There is provided a process for preparing a carboxylic acid ester of formula (3): R 2 COOR 1 (3) wherein R 1 is an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an aralkyl group which may be substituted, or a heteroarylalkyl group which may be substituted, and R 2 is an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an aryl group which may be substituted, a heteroaryl which may be substituted, an aralkyl group which may be substituted, or a heteroarylalkyl group which may be substituted, which process is characterized by the steps of reacting a monohydroxy compound of formula (1): R 1 OH   (1) wherein R 1 is as defined above, with a zirconium compound of formula (6): Zr(OR 8 ) 4 (6) wherein R 8 is an alkyl group or an aryl group which may be substituted and is not the same as R 1 , to prepare a zirconium catalyst, and reacting a carboxylic acid of formula (2): R 2 COOH   (2) wherein R 2 is as defined above, with the monohydroxy compound of formula (1) in the presence of the zirconium catalyst.

  提供了一种制备化学式为(3)的羧酸酯的方法：R2COOR1 (3)，其中R1是可以被取代的烷基、可以被取代的烯基、可以被取代的炔基、可以被取代的芳基或可以被取代的杂芳基烷基，R2是可以被取代的烷基、可以被取代的烯基、可以被取代的炔基、可以被取代的芳基、可以被取代的杂芳基、可以被取代的芳基烷基或可以被取代的杂芳基烷基。该方法的特征在于将化学式为(1)的单羟基化合物：R1OH (1)（其中R1如上定义）与化学式为(6)的锆化合物反应：Zr(OR8)4 (6)（其中R8是可以被取代的烷基或芳基，且不同于R1），制备锆催化剂，然后在锆催化剂存在的情况下，将化学式为(2)的羧酸：R2COOH (2)（其中R2如上定义）与化学式为(1)的单羟基化合物反应。