2,6-二甲氧基苯甲酸 | 1466-76-8

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香酸
• 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: 2,6-二甲氧基苯甲酸
• 中文别名: 2,6-二甲氧基苯酸；雷锁酸二甲醚
• 英文名称: 2-6-dimethoxybenzoic acid
• 英文别名: 2,6-Dimethoxybenzoic acid
• CAS: 1466-76-8
• 化学式: C₉H₁₀O₄
• mdl: MFCD00002437
• 分子量: 182.176
• InChiKey: MBIZFBDREVRUHY-UHFFFAOYSA-N

物化性质

• 熔点：
  185-187 °C (lit.)
• 沸点：
  275.56°C (rough estimate)
• 密度：
  1.2481 (rough estimate)
• 溶解度：
  14.7g/l可溶
• LogP：
  0.660
• 物理描述：
  Solid
• 蒸汽压力：
  1.90e-07 mmHg
• 保留指数：
  1460
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，没有已知危险反应。应避免与氧化物、碱接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xn
• 安全说明：
  S26,S36,S37/39
• 危险类别码：
  R22,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2918990090
• 危险品运输编号：
  NONH for all modes of transport
• RTECS号：
  DG8598725
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  保持贮藏器密封，储存在阴凉、干燥处，并确保工作间有良好的通风或排气装置。

SDS

Name:	2 6-Dimethoxybenzoic Acid 99% Material Safety Data Sheet
Synonym:	None known
CAS:	1466-76-8

Section 1 - Chemical Product MSDS Name:2 6-Dimethoxybenzoic Acid 99% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1466-76-8	2,6-Dimethoxybenzoic Acid	99	215-985-4

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.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
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.
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:

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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:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, 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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
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# 1466-76-8: 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:
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: Powder
Color: white to off-white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 186.00 - 187.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: 35 wt% (25 c)
Specific Gravity/Density:
Molecular Formula: C9H10O4
Molecular Weight: 182.18

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
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# 1466-76-8: DG8598725 LD50/LC50:
CAS# 1466-76-8: Oral, rat: LD50 = >500 mg/kg.
Carcinogenicity:
2,6-Dimethoxybenzoic Acid - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
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# 1466-76-8: No information available.
Canada
CAS# 1466-76-8 is listed on Canada's NDSL List.
CAS# 1466-76-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1466-76-8 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

2,6-二甲氧基苯甲酸是一种在植物来源的食物中发现的多酚化合物。

化学性质

本品为固体，熔点186～187℃，难溶于水，但能溶于碱及有机溶剂，如苯、甲苯。

用途

2,6-二甲氧基苯甲酸是杀螨剂苯螨特的中间体，并且用作医药中间体和有机合成原料。

生产方法

该化合物可通过三步反应合成：

1. 第一步：以N,N-二甲基甲酰胺（DMF）为溶剂，间苯二酚∶碳酸钾∶二氧化碳=1.0∶0.5∶1.5，在1.3MPa、135～137℃条件下反应16.5小时后，经酸化制得2,6-二羟基苯甲酸。

2. 第二步：使2,6-二羟基苯甲酸∶硫酸二甲酯=1∶3，在碱性条件下反应得到2,6-二羟基苯甲酸甲酯。

3. 第三步：将上一步产物经碱催化水解、酸化，最终制得2,6-二甲氧基苯甲酸。

反应信息

• 作为反应物：
  描述：

  2,6-二甲氧基苯甲酸 在 potassium tert-butylate 、 氧气 、 copper diacetate 、 silver carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1,2,3-三甲氧基苯
  参考文献：
  名称：

  芳香羧酸的脱羧醚化

  摘要：

  脱羧 Chan-Evans-Lam 型偶联是一种从容易获得的芳族羧酸开始区域特异性构建二芳基和烷基芳基醚的新策略。它们允许在有氧条件下，在碳酸银作为脱羧催化剂和乙酸铜作为交叉偶联催化剂存在下，通过与原硅酸烷基酯或硼酸芳基酯反应，将各种芳族羧酸盐转化为相应的芳基醚。

  DOI：

  10.1021/ja304539j
• 作为产物：
  描述：

  2,6-二甲氧基苯甲腈 在 barium dihydroxide 作用下， 生成 2,6-二甲氧基苯甲酸
  参考文献：
  名称：

  Lobry de Bruyn, Recueil des Travaux Chimiques des Pays-Bas, 1883, vol. 2, p. 237

  摘要：

  DOI：
• 作为试剂：
  描述：

  在 2,6-二甲氧基苯甲酸 作用下， 以 氘代氯仿 为溶剂， 反应 2.0h， 生成 间苯二甲醚
  参考文献：
  名称：

  金（I）催化的原脱羧机理

  摘要：

  描述了金催化的原脱羧反应的机理研究。已通过实验和计算研究了每个反应步骤。更具体地说，已经通过动力学研究确定了用于脱羧步骤的活化参数。关于芳基金中间体水解的进一步实验研究表明，原脱脂可以在高转化率下与脱羧过程竞争。速率限制步骤中的此切换已显示为取决于p K a。这些研究得到了DFT计算的支持，使人们能够更好地了解反应机理的哪些普遍特征是造成脱羧过程的原因。

  DOI：

  10.1002/chem.201405716

文献信息

• [EN] DISUBSTITUTED OCTAHY-DROPYRROLO [3,4-C] PYRROLES AS OREXIN RECEPTOR MODULATORS<br/>[FR] OCTAHYDROPYRROLO [3,4-C] PYRROLES DISUBSTITUÉS UTILISÉS COMME MODULATEURS DU RÉCEPTEUR DE L'OREXINE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2012145581A1

  公开（公告）日：2012-10-26

  Disubstituted octahydropyrrolo[3,4-c]pyrrole compounds are described, which are useful as orexin receptor modulators. Such compounds may be useful in pharmaceutical compositions and methods for the treatment of diseased states, disorders, and conditions mediated by orexin activity, such as insomnia.

  描述了二取代的八氢吡咯[3,4-c]吡咯化合物，这些化合物可用作促进睡眠素受体的调节剂。这些化合物可能在药物组合物和治疗由促进睡眠素活性介导的疾病状态、紊乱和病况的方法中有用，比如失眠。
• AZOLE INHIBITORS OF CYTOKINE PRODUCTION
  申请人：——

  公开号：US20010044445A1

  公开（公告）日：2001-11-22

  Compounds having the formula 1 are useful for treating diseases that are prevented by or ameliorated with Interleukin-2, Interleukin-4, or Interleukin-5 production inhibitors.

  具有以下化学式的化合物对于治疗由白细胞介素-2、白细胞介素-4或白细胞介素-5产生抑制剂预防或改善的疾病是有用的。
• Dimethylmalonyltrialkylphosphoranes: probing the steric effect on phosphorus and its stereochemical consequence in esterification reactions of chiral secondary alcohols
  作者：J. Dyck、S. Zavorine、A.J. Robertson、A. Capretta、V. Larichev、J. Britten、J. McNulty

  DOI：10.1016/j.jorganchem.2004.10.046

  日期：2005.5

  High chemical yields and high levels of stereochemical inversion are demonstrated in the phosphorane-mediated esterification reaction of chiral alcohols with non-hindered carboxylic acids through the incorporation of sterically non-hindered alkyl groups of phosphorus.

  通过引入空间上不受阻碍的烷基磷，手性醇与不受阻碍的羧酸的膦烷介导的酯化反应证明了高化学产率和高水平的立体化学转化。
• Dimethylmalonyltrialkylphosphoranes:  New General Reagents for Esterification Reactions Allowing Controlled Inversion or Retention of Configuration on Chiral Alcohols
  作者：James McNulty、Alfredo Capretta、Vladimir Laritchev、Jeff Dyck、Al J. Robertson

  DOI：10.1021/jo026639y

  日期：2003.2.1

  through reaction of a trialkylphosphine with 2-chlorodimethylmalonate in the presence of triethylamine. These new reagents promote the condensation reaction of carboxylic acids with alcohols to provide esters along with trialkylphosphine oxide and dimethylmalonate. The condensation reaction of chiral secondary alcohols can be controlled to give either high levels of inversion or retention through a

  在三乙胺存在下，通过使三烷基膦与2-氯二甲基丙二酸酯反应制备了新型的三烷基膦。这些新试剂促进了羧酸与醇的缩合反应，以提供酯以及三烷基氧化膦和丙二酸二甲酯。可以控制手性仲醇的缩合反应，以通过涉及反应介质，溶剂的碱性以及调节羧酸的电子和空间性质以及所用磷烷的空间性质的微妙相互作用，实现高水平的转化或保留。 。推测有一个连贯的机制来解释这些观察结果，这些观察结果涉及通过初始的酰氧基phosph离子进行的反应。
• [EN] BORONIC ACID DERIVATIVES AND THERAPEUTIC USES THEREOF<br/>[FR] DÉRIVÉS D'ACIDE BORONIQUE ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：REMPEX PHARMACEUTICALS INC

  公开号：WO2016003929A1

  公开（公告）日：2016-01-07

  Disclosed herein are antimicrobial compounds compositions, pharmaceutical compositions, the use and preparation thereof. Some embodiments relate to boronic acid derivatives and their use as therapeutic agents.

  本文揭示了抗微生物化合物组合物、药物组合物及其使用和制备。一些实施例涉及硼酸衍生物及其作为治疗剂的使用。

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