硫代特戊酸 | 55561-02-9

• 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 - 有机酸及其衍生物 - 硫代酸
• 中文名称: 硫代特戊酸
• 中文别名: 三甲基硫代乙酸
• 英文名称: thiopivalic acid
• 英文别名: 2,2-dimethylpropanethioic S-acid；2-methyl-2-methylthiopropionic acid
• CAS: 55561-02-9
• 化学式: C₅H₁₀OS
• mdl: MFCD00009729
• 分子量: 118.2
• InChiKey: JHSXHKMJBWOMRU-UHFFFAOYSA-N

物化性质

• 沸点：
  125-127 °C
• 密度：
  0.966±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  8
• 危险品运输编号：
  UN 2920
• 包装等级：
  II
• 危险类别：
  8

SDS

Name:	Thiopivalic acid 97% Material Safety Data Sheet
Synonym:	Trimethylthiolacetic aci
CAS:	55561-02-9

Section 1 - Chemical Product MSDS Name:Thiopivalic acid 97% Material Safety Data Sheet
Synonym:Trimethylthiolacetic aci

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
55561-02-9	Thiopivalic acid, 97%		259-708-5

Hazard Symbols: C
Risk Phrases: 10 35

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Flammable. Causes severe burns.Stench.
Potential Health Effects
Eye:
Contact with eyes may cause severe irritation, and possible eye burns.
Skin:
May cause severe irritation and possible burns.
Ingestion:
Not available.
Inhalation:
May cause severe irritation of the respiratory tract with sore throat, coughing, shortness of breath and delayed lung edema. Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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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.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
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.
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.
Extinguishing Media:
Not available.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Not available.
Storage:
Flammables-area.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits.
Exposure Limits CAS# 55561-02-9: Personal Protective Equipment Eyes: Wear safety glasses and chemical goggles if splashing is possible.
Skin:
Wear appropriate protective gloves and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
Wear a NIOSH/MSHA or European Standard EN 149 approved full-facepiece airline respirator in the positive pressure mode with emergency escape provisions.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 125.0 - 127.0 deg C @ 760.00m
Freezing/Melting Point: 0 deg C
Autoignition Temperature: Not available.
Flash Point: 23 deg C ( 73.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: .9300g/cm3
Molecular Formula: C5H10OS
Molecular Weight: 118.19

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Not available.
Incompatibilities with Other Materials:
Strong oxidizing agents - strong bases.
Hazardous Decomposition Products:
Carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 55561-02-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Thiopivalic acid, 97% - 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
Shipping Name: CORROSIVE LIQUID, FLAMMABLE, N.O.S.*
Hazard Class: 8 (3)
UN Number: 2920
Packing Group: II
IMO
Shipping Name: CORROSIVE LIQUID, FLAMMABLE, N.O.S.
Hazard Class: 8 (3)
UN Number: 2920
Packing Group: II
RID/ADR
Shipping Name: CORROSIVE LIQUID, FLAMMABLE, N.O.S.
Hazard Class: 8
UN Number: 2920
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 10 Flammable.
R 35 Causes severe burns.
Safety Phrases:
S 16 Keep away from sources of ignition - No
smoking.
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 55561-02-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 55561-02-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 55561-02-9 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

制备方法

有机中间体。

用途简介

暂无相关信息。

反应信息

• 作为反应物：
  描述：

  硫代特戊酸 在 盐酸 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 6.0h， 生成 2-(tert-butyl)-4,4-dimethyl-1,3-thiazole-5(4H)-thione
  参考文献：
  名称：

  杂狄尔斯-阿尔德与1,3-噻唑-5-（4反应ħ）-thiones

  摘要：

  Hetro- Diels - Alder与1,3-噻唑-5（4 H）-硫酮的反应

  DOI：

  10.1002/hlca.19880710825
• 作为产物：
  描述：

  三甲基乙酸 在 劳森试剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以78%的产率得到硫代特戊酸
  参考文献：
  名称：

  用劳森试剂将羧酸转化为硫代酸的简单方法

  摘要：

  已经开发出一种使用劳森试剂将羧酸转化为硫酯的一步方案。

  DOI：

  10.1016/j.tetlet.2009.09.080

文献信息

• Asymmetric Desymmetrization of Oxetanes for the Synthesis of Chiral Tetrahydrothiophenes and Tetrahydroselenophenes
  作者：Renwei Zhang、Wengang Guo、Meng Duan、K. N. Houk、Jianwei Sun

  DOI：10.1002/anie.201910917

  日期：2019.12.9

  Chiral tetrahydrothiophenes and tetrahydroselenophenes are highly useful structural units. Described here is a new catalytic asymmetric approach for their synthesis. With a suitable chiral Brønsted acid catalyst, an oxetane desymmetrization by a well-positioned internal sulfur or selenium nucleophile proceeded efficiently to generate all-carbon quaternary stereocenters with excellent enantioselectivities

  手性四氢噻吩和四氢硒吩是高度有用的结构单元。这里描述了一种新的催化不对称合成方法。使用合适的手性布朗斯台德酸催化剂，通过位置适当的内部硫或硒亲核试剂进行的氧杂环丁烷脱对称反应可有效地进行，以产生具有出色对映选择性的全碳四元立体中心。分别以硫代酯和硒代酯的形式驯服硫和硒亲核试剂对这项工作的成功至关重要。该方法还允许容易地合成手性四氢噻喃。包括DFT计算在内的机械研究表明了分子内酰基转移途径。还展示了手性产品的实用性。
• Studies on topical antiinflammatory agents. II. Synthesis and vasoconstrictive activity of 21-substituted corticosteroids with sulfur-containing moieties.
  作者：Morihiro MITSUKUCHI、Tomoyuki IKEMOTO、Minoru TAGUCHI、Shohei HIGUCHI、Satoshi ABE、Hajime YASUI、Katsuo HATAYAMA、Kaoru SOTA

  DOI：10.1248/cpb.37.1795

  日期：——

  As part of the search for new topical antiinflammatory agents, various 21-substituted corticosteroids having sulfur-containing moieties were prepared and tested for vasoconstrictive activity in humans. A structure-activity relationship study revealed that substitution of the 21-hydroxy group with a lower alkyl-thio group enhanced the activity. The activities of the 21-methylthio (3Ad) and the 21-ethylthio (3Ae) compounds were more potent than that of 9α-fluoro-11β, 21-dihydroxy-16β-methyl-17α-valeroyloxy-1, 4-pregnadiene-3, 20-dione (betamethasone 17-valerate, BV).

  在寻找新型局部抗炎药物的过程中，制备并测试了多种含有硫元素的21-取代皮质类固醇在人体的血管收缩活性。结构-活性关系研究表明，将21-羟基基团用低级烷基硫基团替代可以增强活性。21-甲硫基（3Ad）和21-乙硫基（3Ae）化合物的活性比9α-氟-11β, 21-二羟基-16β-甲基-17α-戊酸氧基-1, 4-孕甾二烯-3, 20-二酮（倍他米松17-戊酸酯，BV）更强。
• 2,2-Disubstituted 4-Acylthio-3-oxobutyl Groups as Esterase- and Thermolabile Protecting Groups of Phosphodiesters
  作者：Emilia Kiuru、Zafar Ahmed、Harri Lönnberg、Leonid Beigelman、Mikko Ora

  DOI：10.1021/jo302421u

  日期：2013.2.1

  2-substituents and the size of the acylthio group. The acyl group evidently migrates from the sulfur atom to C3-gem-diol obtained by hydration of the keto group and the exposed mercapto group attacks on C1 resulting in departure of the protecting group as 4,4-disubstituted 3-acyloxy-4,5-dihydrothiophene with concomitant release of the desired phosphodiester.

  已经引入了五个不同的2，2-二取代的4-酰基硫基-3-氧代丁基作为酯酶不稳定的磷酸二酯保护基，它们另外是热不稳定的。的磷酸三酯1 - 3通过HPLC-ESI-MS制备，以确定在37酶和非酶去除这些基团的速率℃和pH 7.5。另外，1 H NMR光谱监测用于中间体和产物的结构表征。当用猪肝酯酶处理时，这些基团通过酶促脱酰基作用，然后快速化学环化成4,4-二取代的二氢噻吩-3（2 H）-一。可以通过4-酰硫基取代基的性质来调节酶促脱保护的速率，苯甲酰基和乙酰基的去除速度是新戊酰基的50和5倍。酶促脱保护后未观察到谷胱甘肽的烷基化。根据2-取代基的电负性和酰硫基的大小，非酶促脱保护的半衰期为0.57至35小时。酰基显然来自硫原子C3-迁移宝石由酮基的水合和产生保护基团的离去C1上的暴露的巯基的攻击得到二醇如4,4-二取代-3-酰氧基-4,5- -二氢噻吩并伴随释放所需的磷酸二酯。
• A Facile Synthesis of Thioacids by Hydrolysis of 1-(Acylthio)ethaniminium Chlorides
  作者：Masaharu Toriyama、Haruo Kamijo、Shigeyasu Motohashi、Toshio Takido、Kunio Itabashi

  DOI：10.1080/10426500307837

  日期：2003.8.1

  A facile method for the preparation of thioacids in moderate to good yields has been developed by hydrolysis of 1-(acylthio)ethaniminium chlorides under a liquid-liquid two phase system consisting of benzene and a sodium hydroxide aqueous solution at room temperature. We have achieved facile preparation of these compounds without use of toxic compounds such as hydrogen sulfide.

  通过在由苯和氢氧化钠水溶液组成的液-液两相系统下，在室温下水解 1-（酰硫基）乙胺氯化物，开发了一种以中等至良好收率制备硫代酸的简便方法。我们已经在不使用硫化氢等有毒化合物的情况下轻松制备了这些化合物。
• Mononucleoside Phosphotriester Derivatives with S-Acyl-2-thioethyl Bioreversible Phosphate-Protecting Groups: Intracellular Delivery of 3'-Azido-2',3'-dideoxythymidine 5'-Monophosphate
  作者：Isabelle Lefebvre、Christian Perigaud、Alain Pompon、Anne-Marie Aubertin、Jean-Luc Girardet、Andre Kirn、Gilles Gosselin、Jean-Louis Imbach

  DOI：10.1021/jm00020a007

  日期：1995.9

  The synthesis, in vitro anti-HIV-1 activity, and decomposition pathways of several mononucleoside phosphotriester derivatives of 3'-azido-2',3'-dideoxythymidine (AZT) incorporating a new kind of carboxylate esterase-labile transient phosphate-protecting group, namely, S-acyl-2-thioethyl, are reported. All the described compounds showed marked antiviral activity in thymidine kinase-deficient CEM cells

  3'-叠氮基2'，3'-二脱氧胸苷（AZT）的几种单核苷磷酸三酯衍生物的合成，体外抗HIV-1活性和分解途径，结合了一种新型的羧酸酯酶不稳定的瞬时磷酸保护基团据报道，即S-酰基-2-硫代乙基。所有描述的化合物在胸腺嘧啶激酶缺失的CEM细胞中均表现出显着的抗病毒活性，其中AZT实际上是无活性的。结果强烈支持这样的假说，即这种前核苷酸通过AZT的5'-单核苷酸的细胞内递送发挥其生物学作用。在细胞提取物和培养基中的分解研究证实了这一点。

表征谱图