rac-2,3-dimethylsuccinic acid | 608-40-2

• 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 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: rac-2,3-dimethylsuccinic acid
• 英文别名: (+/-)-RR-2,3-dimethylbutanedioic acid；racemic 2,3-dimethylsuccinic acid；acide dimethyl-2,3 succinique DL；(D,L)-2,3-dimethylsuccinic acid；d,l-2,3-dimethylsuccinic acid；DL-2,3-Dimethylsuccinic acid；(2S,3S)-2,3-dimethylbutanedioic acid
• CAS: 608-40-2；5866-39-7；5866-40-0；13545-04-5；57694-62-9；608-39-9；143291-17-2
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: KLZYRCVPDWTZLH-IMJSIDKUSA-N

物化性质

• 熔点：
  118-122 °C
• 沸点：
  311.39°C (rough estimate)
• 密度：
  1.4528 (rough estimate)
• 稳定性/保质期：
  性质与稳定性：在常温常压下，该物质不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

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
• 海关编码：
  2917190090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将产品存放在阴凉干燥的环境中。

SDS

Name:	2 3-Dimethylsuccinic Acid (Mixture of D L and Meso) 99+% Material Safety Data Sheet
Synonym:	None known
CAS:	13545-04-5

Section 1 - Chemical Product MSDS Name:2 3-Dimethylsuccinic Acid (Mixture of D L and Meso) 99+% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13545-04-5	2,3-Dimethylsuccinic Acid	>99	236-915-9

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.The toxicological properties of this material have not been fully investigated.
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. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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. 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.
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# 13545-04-5: 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: Solid
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 120 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:
Specific Gravity/Density:
Molecular Formula: C6H10O4
Molecular Weight: 146.14

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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, 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# 13545-04-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,3-Dimethylsuccinic Acid - 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 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# 13545-04-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13545-04-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13545-04-5 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

用途

2,3-二甲基丁二酸用作研究用化合物。

反应信息

• 作为反应物：
  描述：

  rac-2,3-dimethylsuccinic acid 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 racem.-2,3-dimethyl-1,4-bis-(toluene-4-sulfonyloxy)-butane
  参考文献：
  名称：

  Stereoselective coupling reaction of thioamides via a dithia-Cope rearrangement

  摘要：

  DOI：

  10.1021/ja00474a047
• 作为产物：
  描述：

  2,3-二甲基马来酸酐 在 盐酸 、 potassium chloride 作用下， 生成 rac-2,3-dimethylsuccinic acid
  参考文献：
  名称：

  Effect of Structure on the Stereochemistry of Electrode Reactions. Unsaturated C₄-Dibasic Acids and Esters. Stereospecific Reduction of the Double Bond

  摘要：

  DOI：

  10.1021/ja01545a037

文献信息

• Stéréospécificité de l'addition de Michael d'ènethiolates avec les énones acycliques
  作者：Kafui Kpegba、Patrick Metzner、Rosé Rakotonirina

  DOI：10.1016/s0040-4020(01)80066-1

  日期：1989.1

  E-enones (3-penten-2-one, chalcone) occurs with high stereospecificity: anti/syn product ratios are identical to the cis/trans enethiolate ratios. A pseudo-cyclic transition state is proposed with substituents of the enone C-C double bond occupying favorable equatorial positions. The 1,4-addition reaction is kineticaly controlled. In contrast to ester enolates, enethiolates allow the use of enones without

  锂化二硫酯与无环 β 取代的 E 烯酮的 1,4-加成反应得到非对映异构体 5-氧代烷基硫代硫酸盐。通过化学相关性将反构型分配给主要的非对映异构体。这种立体化学取决于前手侧伴侣的构型。通过捕获实验分析中间烯硫酸盐的 cisl/trans 比率。观察到 2 例二硫酯的高选择性顺式去质子化。E-烯酮 （3-penten-2-one， chalcone） 的 Michael 添加具有很高的立体特异性：抗/syn 产物比率与顺式/反式烯乙酸盐比率相同。提出了一种伪循环过渡态，烯酮 C-C 双键的取代基占据有利的赤道位置。1,4-加成反应是动力学控制的。与酯烯醇酯相比，烯硫醇酯允许使用烯酮，而不需要叔丁基或苯基。观察到的非对映选择性（抗/合成比高达 95 ： 5）提供了一种通过在非环系列中形成碳-碳键来创建两个邻近碳取代不对称中心的新方法。然而，当使用不饱和二酯作为受体时，观察到较差的选择性。
• Dynamic behavior of dicobalt hexacarbonyl propargyl cations and their reactions with chiral nucleophiles
  作者：Stuart L. Schreiber、Michael T. Klimas、Tarek Sammakia

  DOI：10.1021/ja00253a030

  日期：1987.9

  4-Phenyl-2,4,6-triazatetra~yclo[6.3.2.0~~~.0~~~] trideca- 10,12-diene-3,5dione was prepared by the reported procedure.’ Spectral parameters are as follows: I3C NMR (CDCI,, 30 “C, 25.2 MHz, CHC1, assigned as 76.91 ppm) 6 73.750 (Cl/C5), 40.957 (C2/C4/C6/C8), 127.532 (C6/C9), 131.516, 127.752 (ipso/para C), 128.830, 125.435 (meta/para C), 148.573 (C=O); ’H NMR (CDzCIz, XL 200 MHz, 30 OC, tetramethylsilane)

  4-Phenyl-2,4,6-triazatetra-yclo[6.3.2.0~~~.0~~~] trideca-10,12-diene-3,5dione 通过报道的程序制备。光谱参数如下： I3C NMR (CDCI,, 30"C, 25.2 MHz, CHC1, 指定为 76.91 ppm) 6 73.750 (Cl/C5), 40.957 (C2/C4/C6/C8), 127.592 (C6/C8) ), 131.516, 127.752 (ipso/para C), 128.830, 125.435 (meta/para C), 148.573 (C=O); 'H NMR (CDzClz, XL 200 MHz, 30 OC, 四甲基硅烷) 6 7.49 (Ph), 4.92 (t, J = 7.7 Hz, Hl/H5), 4.35 (主要偶联 t, J = 7.7 Hz, H2/H4/
• Double asymmetric hydrogenation of conjugated dienes catalysed by ruthenium binap complexes
  作者：Hitoshi Muramatsu、Hiroyuki Kawano、Youichi Ishii、Masahiko Saburi、Yasuzo Uchida

  DOI：10.1039/c39890000769

  日期：——

  Buta-1,3-diene-2,3-dicarboxylic acid is smoothly hydrogenated in the presence of a ruthenium–(R)-binap complex as a catalyst via two consecutive 1,2-hydrogen additions, giving rise to (S,S)-2,3-dimethylsuccinic acid with 98% diastereoisomeric excess and 96% enantiomeric excess.

  丁-1,3-二烯-2,3-二羧酸被平稳地在钌（的存在下氢化- [R）-BINAP络合物作为催化剂通过两个连续的1,2-氢的添加，从而产生（小号，小号）-2,3-二甲基琥珀酸，其非对映异构体过量为98％，对映异构体过量为96％。
• Simple and efficient methods for discrimination of chiral diacids and chiral alpha-methyl amines
  作者：Sachin R. Chaudhari、N. Suryaprakash

  DOI：10.1039/c2ob25599e

  日期：——

  The three-component chiral derivatization protocols have been developed for 1H, 13C and 19F NMR spectroscopic discrimination of chiral diacids by their coordination and self-assembly with optically active (R)-α-methylbenzylamine and 2-formylphenylboronic acid or 3-fluoro-2-formylmethylboronic acid. These protocols yield a mixture of diastereomeric imino-boronate esters which are identified by the well-resolved

  通过手性二酸的配位和自组装与光学活性的相互作用，开发了用于手性二酸的1 H，13 C和19 F NMR光谱学鉴别的三组分手性衍生方案。（R）-α-甲基苄胺 和 2-甲酰基苯基硼酸或3-氟-2-甲酰基甲基硼酸。这些方案产生了非对映异构亚氨基硼酸酯的混合物，该混合物由良好解析的非对映异构体峰鉴定，在其相应的1 H和19 F NMR光谱中具有显着的化学位移差异，范围高达0.6和2.1 ppm ，没有消旋或动力学拆分从而可以确定对映体纯度。还已经开发了使用光学纯的方法来鉴别手性α-甲基胺的方案反式-1,2-环己烷二甲酸 与...结合 2-甲酰基苯基硼酸或3-氟-2-氟甲基硼酸。在大量的手性二酸和手性α-甲基胺上已经证明了所提出的策略。
• Highly diastereoselective tandem alkylation of acyclic α,β-unsaturated esters based on the novel use of dithioacetal unit
  作者：Hisashi Kawasaki、Kiyoshi Tomioka、Kenji Koga

  DOI：10.1016/s0040-4039(00)98610-6

  日期：1985.1

  Highly diastereoselective tandem alkylation process of acyclic α,β-unsaturated esters was developed based on the novel use of dithioacetal as a stereocontrolling unit.

  基于二硫缩醛作为立体控制单元的新用途，开发了无环α，β-不饱和酯的高度非对映选择性串联烷基化方法。