反式-2,3-二甲基丙烯酸 | 13201-46-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 反式-2,3-二甲基丙烯酸
• 中文别名: 2-甲基丁-2-烯酸
• 英文名称: 2-methylbut-2-enoic acid
• 英文别名: 2-methyl-2-butenoic acid；2,3-dimethylacrylic acid；2-Butenoic acid, 2-methyl-
• CAS: 13201-46-2
• 化学式: C₅H₈O₂
• mdl: MFCD00002654
• 分子量: 100.117
• InChiKey: UIERETOOQGIECD-UHFFFAOYSA-N

物化性质

• 熔点：
  61-64 °C(lit.)
• 沸点：
  95-96 °C12 mm Hg(lit.)
• 密度：
  0.969 g/mL at 25 °C(lit.)
• LogP：
  1.076 (est)
• 保留指数：
  921;934
• 稳定性/保质期：
  存在于烤烟烟叶、白肋烟烟叶、香料烟烟叶以及烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• 海关编码：
  2916190090
• 危险品运输编号：
  UN 3261 8/PG 2

SDS

Name:	2-Methylbut-2-enoic acid 97% Material Safety Data Sheet
Synonym:	2,3-Dimethylacrylic aci
CAS:	13201-46-2

Section 1 - Chemical Product MSDS Name:2-Methylbut-2-enoic acid 97% Material Safety Data Sheet
Synonym:2,3-Dimethylacrylic aci

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13201-46-2	2-Methylbut-2-enoic acid	97%	236-167-3

Hazard Symbols: C
Risk Phrases: 34

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

---

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 immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:
Treat symptomatically and supportively.

---

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.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

---

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.

---

Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

---

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# 13201-46-2: Personal Protective Equipment Eyes: Not available.
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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white crystalline solid
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 95 - 96 deg C @11.5mmHg
Freezing/Melting Point: 63 - 64 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: C5H8O2
Molecular Weight: 100

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13201-46-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Methylbut-2-enoic acid - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3261
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing group: III

---

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# 13201-46-2: No information available.
Canada
CAS# 13201-46-2 is listed on Canada's DSL List.
CAS# 13201-46-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13201-46-2 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  反式-2,3-二甲基丙烯酸 在 lithium aluminium tetrahydride 作用下， 生成 (E)-2-methyl-2-buten-1-ol
  参考文献：
  名称：

  烷基碘的钯催化 Heck 型反应

  摘要：

  描述了未活化的烷基碘化物的钯催化的 Heck 型反应。该过程在烯烃和烷基碘组分方面显示出广泛的底物范围，并提供对各种环状产物的有效访问。该反应被提议通过混合有机金属-自由基机制进行，促进与烷基卤化物偶联伙伴的 Heck 型过程。还报告了最初的分子间研究，证明了这种方法在合成中的潜在广泛适用性。

  DOI：

  10.1021/ja2091883
• 作为产物：
  描述：

  (2-oxo-1,2-diphenylethyl) 2-methylbut-2-enoate 在 potassium phosphate 、 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 维生素 C 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以100%的产率得到反式-2,3-二甲基丙烯酸
  参考文献：
  名称：

  Desyl和Phenacyl作为多功能，光催化可裂解的保护基团：在不同（可见）光下的经典方法

  摘要：

  已经开发了使用可见光光氧化还原催化来脱保护经典苯甲酰基（Pac）和去甲酰基（Dsy）保护基的高效催化策略。故意使用具有K 3 PO 4的中性两相乙腈/水混合物，并施加催化量的[Ru（bpy）3 ]（PF 6）2与抗坏血酸结合使用是对Pac和Dsy保护的羧酸进行真正的催化脱保护的关键。我们温和而稳健的方案允许以非常好的定量产量快速而选择性地释放游离羧酸，而只需要低的催化剂负载量（1 mol％）。从市场上可买到的前体容易引入的Pac和Dsy均可用于直接保护羧酸和氨基酸，与许多其他常见的保护基团具有正交性。我们进一步证明了这些先前被低估的保护基团与我们的催化裂解条件相结合的普遍适用性和多功能性，这是由获得的高官能团耐受性所强调的。而且，该方法可以成功地适应固相合成的要求。作为有效可见光，光催化连接子裂解的原理证明，将Boc保护的三肽从市售的溴化王树脂中分离出来。

  DOI：

  10.1021/acscatal.7b02117
• 作为试剂：
  描述：

  2-苯乙胺 、 氯甲酸甲酯 在 三乙胺 、 反式-2,3-二甲基丙烯酸 作用下， 生成 methyl N-(2-phenylethyl)carbamate 、 1,3-dichloro-2-(chloromethyl)propan-2-amine hydrochloride
  参考文献：
  名称：

  Activation of 2-Alkenoic Acids as Mixed Anhydrides with Diphenylphosphinic Acid for the Formation of Carboxamides

  摘要：

  DOI：

  10.1055/s-1980-29029

文献信息

• Expedient Iron-Catalyzed C−H Allylation/Alkylation by Triazole Assistance with Ample Scope
  作者：Gianpiero Cera、Tobias Haven、Lutz Ackermann

  DOI：10.1002/anie.201509603

  日期：2016.1.22

  for the iron‐catalyzed C−H allylation of arenes, heteroarenes, and alkenes with ample scope. The versatile catalyst also proved competent for site‐selective methylation, benzylation, and alkylation with challenging primary and secondary halides. Triazole‐assisted C−H activation proceeded chemo‐, site‐, and diastereo‐selectively, and the modular TAM directing group was readily removed in a traceless

  三唑的协助为广泛范围内的芳烃，杂芳烃和烯烃的铁催化的CHH烯丙基化的统一策略奠定了基础。事实证明，这种多功能催化剂还可胜任具有选择性的一级和二级卤化物的定点甲基化，苄基化和烷基化。三唑辅助的CH活化是化学，位点和非对映选择性的，在极温和的反应条件下，模块化TAM导向基团很容易以无痕方式除去。
• Inhibitors of CYP 17
  申请人：BOCK Mark G.

  公开号：US20100331326A1

  公开（公告）日：2010-12-30

  The present invention provides compounds of Formula (I) and (II), or a pharmaceutically acceptable salts thereof, where R 53 , R 54 , p, q, and n are as defined herein. The compounds of the present invention have been found to be useful as 17α-hydroxylase/C 17,20 -lyase inhibitors.

  本发明提供了式(I)和(II)的化合物，或其药用可接受的盐， 其中R 53 ，R 54 ，p，q和n如本文所述定义。本发明的化合物被发现作为17α-羟化酶/C 17,20 -裂解酶抑制剂是有用的。
• Hydroarylation of Activated Alkenes Enabled by Proton-Coupled Electron Transfer
  作者：Zhaosheng Liu、Shuai Zhong、Xiaochen Ji、Guo-Jun Deng、Huawen Huang

  DOI：10.1021/acscatal.1c00649

  日期：2021.4.16

  of N-arylacrylamides with high 5-exo-trig selectivity through robust proton-coupled electron transfer (PCET). This mild hydroarylation protocol provides a straightforward entry to structurally valuable oxindoles and complements previously established 6-endo-trig cyclization by photochemical triplet energy transfer (TET).

  烯烃的加氢芳基化已被证明是一种原子经济的方法，可从易于获取的原材料中获得官能化的芳烃。在这里，我们报告了可见光诱导的光催化系统，该系统能够通过强大的质子耦合电子转移（PCET）使N-芳基丙烯酰胺具有高的5-exo-trig选择性进行分子内加氢芳基化。这种温和的氢芳化方案可直接进入结构上有价值的羟吲哚，并通过光化学三重态能量转移（TET）补充了先前建立的6-内-trig环化反应。
• Synthesis of Succinimides via Intramolecular Alder-Ene Reaction of 1,6-Enynes
  作者：Xia Chen、Yuling Lu、Zhenhua Guan、Lianghu Gu、Chunmei Chen、Hucheng Zhu、Zengwei Luo、Yonghui Zhang

  DOI：10.1021/acs.orglett.1c00888

  日期：2021.4.16

  A novel and convenient method has been developed for the facile synthesis of functionalized succinimide derivatives via intramolecular Alder-ene reaction of 1,6-enynes. This reaction features mild and metal-free reaction conditions, which offers a green and efficient entry to synthetically important succinimide scaffolds. Preliminary mechanistic studies suggest that a diradical intermediate might be

  通过1，6-烯炔的分子内Alder-ene反应，容易合成功能化的琥珀酰亚胺衍生物。该反应具有温和且无金属的反应条件，为合成重要的琥珀酰亚胺支架提供了绿色且有效的入口。初步的机理研究表明，双自由基中间体可能参与了这种转变。
• Regiocontrolled Coupling of Aromatic and Vinylic Amides with α-Allenols To Form γ-Lactams via Rhodium(III)-Catalyzed C–H Activation
  作者：Zhi Zhou、Guixia Liu、Xiyan Lu

  DOI：10.1021/acs.orglett.6b02903

  日期：2016.11.4

  rhodium(III)-catalyzed C–H activation has been demonstrated. This [4 + 1] annulation reaction provides an efficient method for the synthesis of isoindolinones and 1,5-dihydro-pyrrol-2-ones bearing a tetrasubstituted carbon atom α to the nitrogen atom with good functional group tolerance. The hydroxyl group in the allene substrate is essential in controlling the chemo- and regioselectivity of the reaction probably by

  芳香族和乙烯基酰胺与α-烯醇通过铑（III）催化的CH活化进行了温和的区域控制偶联，从而形成γ-内酰胺。该[4 +1]环化反应为合成具有良好官能团耐受性的对氮原子带有四取代碳原子α的异吲哚啉酮和1,5-二氢-吡咯-2-酮提供了一种有效的方法。丙二烯底物中的羟基可能通过与铑催化剂的配位相互作用控制反应的化学和区域选择性。

表征谱图