(甲硫基)乙酸 | 2444-37-3

• 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
• 中文名称: (甲硫基)乙酸
• 中文别名: (甲硫基)二醋酸；甲基硫代乙酸；(甲基巯基)乙酸；(甲基硫代)乙酸
• 英文名称: methylsulfanyl-acetic acid
• 英文别名: (Methylthio)acetic acid；2-(methylthio)acetic acid；2-methylsulfanylacetic acid
• CAS: 2444-37-3
• 化学式: C₃H₆O₂S
• mdl: MFCD00075444
• 分子量: 106.145
• InChiKey: HGTBAIVLETUVCG-UHFFFAOYSA-N

物化性质

• 熔点：
  13-14 °C(lit.)
• 沸点：
  130-131 °C27 mm Hg(lit.)
• 密度：
  1.219 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• LogP：
  0.655 (est)
• 稳定性/保质期：
  在常温常压下保持稳定，请避免与氧化物直接接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2930909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将容器密封后，存放在紧密封装的容器中，并储存在阴凉、干燥的地方。

SDS

Name:	(Methylthio)acetic acid Material Safety Data Sheet
Synonym:
CAS:	2444-37-3

Section 1 - Chemical Product MSDS Name:(Methylthio)acetic acid Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2444-37-3	(Methylthio)acetic acid		219-483-6

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.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. 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.
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 water spray, dry chemical, carbon dioxide, or chemical foam.

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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:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 2444-37-3: 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: Liquid
Color: Not available.
Odor: stench
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 99 - 100 deg C @4mmHg
Freezing/Melting Point: 13 - 14 deg C
Autoignition Temperature: Not available.
Flash Point: 110 deg C ( 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.219
Molecular Formula: C3H6O2S
Molecular Weight: 106.14

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, sulfur oxides (SOx), including sulfur oxide and sulfur dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2444-37-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(Methylthio)acetic 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
Shipping Name: AVIATION REGULATED LIQUID, N.O.S.*
Hazard Class: 9
UN Number: 3334
Packing Group:
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

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# 2444-37-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2444-37-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2444-37-3 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

反应信息

• 作为反应物：
  描述：

  (甲硫基)乙酸 在 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 1.25h， 生成 (methylthio)acetyl chloride
  参考文献：
  名称：

  合成和生物学评估基于6-磷酸葡萄糖酸脱氢酶的底物抑制剂作为抗非洲锥虫病的潜在药物。

  摘要：

  描述了三个系列的6-磷酸葡萄糖酸酯（6PG）类似物的合成和生物学评估。测试了6PG的（2R）-2-甲基-4,5-二脱氧，（2R）-2-甲基-4-脱氧和2,4-二脱氧类似物作为来自羊肝的6-磷酸葡萄糖酸脱氢酶（6PGDH）的抑制剂。还有布鲁氏锥虫，其中的酶是经过验证的药物靶标。在这三个系列的类似物中，发现七种化合物以微摩尔浓度竞争性地抑制布鲁氏杆菌和绵羊肝酶中的6PGDH。六种抑制剂属于（2R）-2-甲基-4-脱氧系列（6、8、10、12、21、24），一种是（2R）-2-甲基-4,5-二脱氧类似物（29b ）。6PG的2,4-二脱氧类似物不抑制两种酶。还评估了化合物对T的锥虫杀螨作用。

  DOI：

  10.1016/s0968-0896(03)00191-3
• 作为产物：
  描述：

  (甲硫基)乙酸乙酯 在 potassium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 16.0h， 生成 (甲硫基)乙酸
  参考文献：
  名称：

  3-硫代2-氮杂环丁酮：合成及体外抗菌和抗真菌活性

  摘要：

  通过[2 + 2]乙烯酮-亚胺环加成反应，由S-取代的巯基乙酸和席夫碱合成了一系列3-硫醇化的β-内酰胺。然后，某些3-甲硫β内酰胺转化成3-（甲基亚磺酰基），使用β内酰胺和3-（甲磺酰基）β内酰胺米-CPBA不同的反应条件下。所有化合物均通过光谱数据和元素分析进行​​了表征，并评估了它们对包括金黄色葡萄球菌（耐甲氧西林的菌株）在内的致病菌株的体外抗菌和抗真菌活性。初步筛选结果表明，其中一些化合物具有中等至非常好的抗菌和抗真菌活性。

  DOI：

  10.1016/j.tet.2011.05.043
• 作为试剂：
  描述：

  4-苯甲酰苯甲酸 在 (甲硫基)乙酸 作用下， 生成 二氧化碳
  参考文献：
  名称：

  Photoinduced Electron Transfer between Sulfur-Containing Carboxylic Acids and the 4-Carboxybenzophenone Triplet State in Aqueous Solution

  摘要：

  The mechanism of photoinduced electron transfer between sulfur-containing carboxylic acids and the 4-carboxybenzophenone (CB) triplet state in aqueous solution was investigated using laser flash photolysis and steady-state photolysis techniques. Bimolecular rate constants for quenching of the CB triplet state by six sulfur-containing acids, with varying numbers of COO- groups and varying locations with respect to the sulfur atom, were found to be in the range (0.3-2.1) X 10(9) M(-1) s(-1) depending on the charge of the acid molecule. The observation of ketyl radical anions and intermolecular (S therefore S)-bonded radical cations of some of the acids was direct evidence for the participation of electron transfer in the mechanism of quenching. An additional absorption band at approximately 410 nm in the transient absorption spectra for some of the acids was assigned to intramolecularly (S therefore O)-bonded species (for acids for which a five-member ring structure was sterically favorable). Quantum yields of formation of intermediates from flash photolysis experiments and quantum yields of CO2 formation and CB disappearance from the steady-state measurements were determined. The values of these quantum yields clearly indicated that the diffusion apart (escape of the radical ions) of the charge-transfer complex, formed as a primary photochemical step, is the main photochemical pathway (contribution of similar to 90%). Competing processes of proton transfer and back electron transfer within the CT complex gave only minor contributions to these yields. A detailed mechanism of the CB-sensitized photooxidation of sulfur-containing carboxylic acids is proposed, discussed, and compared with that for sulfur-containing amino acids in aqueous solution.

  DOI：

  10.1021/j100069a014

文献信息

• 一种合成β-S氨基酸的方法
  申请人：上海交通大学

  公开号：CN110963980B

  公开（公告）日：2022-03-08

  本发明公开了甲基(R)‑2‑(叔丁基)‑3‑甲酰‑2,3‑二氢噻唑‑4‑甲酸甲酯(I)在制备β‑S氨基酸(II)的中的用途，本发明原料简单易得，通用中间体合成简单；以共同的中间体，可以发散的合成多种不同的β‑S氨基酸，本发明路线短，产率高，可大量合成。
• Exploring the Synthetic Applicability of a Cyanobacterium Nitrilase as Catalyst for Nitrile Hydrolysis
  作者：Chandrani Mukherjee、Dunming Zhu、Edward R. Biehl、Ling Hua

  DOI：10.1002/ejoc.200600699

  日期：2006.12

  specificity and synthetic applicability of the nitrilase from cyanobacterium Synechocystis sp. strain PCC 6803 have been examined. This nitrilase catalyzed the hydrolysis of both aromatic and aliphatic nitriles to the corresponding acids in high yields. Furthermore, the stereoselective hydrolysis of phenyl-substituted β-hydroxy nitriles to (S)-enriched β-hydroxy carboxylic acids and selective hydrolysis of α

  蓝藻集胞藻腈水解酶的底物特异性和合成适用性。菌株 PCC 6803 已被检查。这种腈水解酶以高产率催化芳香族和脂肪族腈水解为相应的酸。此外，还实现了苯基取代的 β-羟基腈立体选择性水解为 (S) 富集的 β-羟基羧酸，以及具有五个或更少亚甲基的 α,ω-二腈选择性水解为 ω-氰基羧酸。这表明来自集胞藻属的腈水解酶。PCC 6803 可能是“绿色”腈水解的有用酶催化剂。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• A Phosphetane Catalyzes Deoxygenative Condensation of α-Keto Esters and Carboxylic Acids via P^III/P^V═O Redox Cycling
  作者：Wei Zhao、Patrick K. Yan、Alexander T. Radosevich

  DOI：10.1021/ja511889y

  日期：2015.1.21

  A small-ring phosphacycle is found to catalyze the deoxygenative condensation of α-keto esters and carboxylic acids. The reaction provides a chemoselective catalytic synthesis of α-acyloxy ester products with good functional group compatibility. Based on both stoichiometric and catalytic mechanistic experiments, the reaction is proposed to proceed via catalytic P(III)/P(V)═O cycling. The importance

  发现小环磷酸环可催化 α-酮酯和羧酸的脱氧缩合。该反应提供了具有良好官能团相容性的α-酰氧基酯产物的化学选择性催化合成。基于化学计量和催化机理实验，建议反应通过催化 P(III)/P(V)=O 循环进行。观察到的温度依赖性产物选择性效应证实了环应变在磷环催化剂中的重要性。结果表明，与路易斯碱（亲核）催化相反，通过 P(III)/P(V)=O 氧化还原循环操作的有机磷基催化剂的设计标准存在固有差异。
• Influence of sulfur groups on carboxylic acid strengths
  作者：Erwin Boschmann、Roger D. Miller

  DOI：10.1016/j.tet.2018.04.007

  日期：2018.5

  The relative acid strength for a series of monocarboxylic acids of the general formula RX(CH2)nCOOH and related dicarboxylic acids of the general formula HOOC(CH2)nX(CH2)nCOOH, where R = Ph or Me, X = CH2, S, SO, or SO2; and n = 1 or 2 as appropriate; have been studied as a function of X. It is found that sulfur containing acids have lower pKa values than the corresponding carbon analogues, that the

  一系列通式R X （CH 2）n COOH的一元羧酸和通式HOOC （CH 2）n X （CH 2）n COOH的相关二元羧酸的相对酸强度，其中R = Ph或Me X = CH 2，S ，SO或SO 2；n = 1或2（视情况而定）；已经研究了作为X的函数。发现含硫的酸具有比相应的碳类似物更低的pKa值，对于硫代酸而言，pK a最高，对于磺酰基酸而言，pK a最低。s随着n的增加而增加，而对于二元羧酸体系，只有硫原子在n从1变为2时pK a（2）– pK a（1）差异显着降低。
• 7-Amino 2-lower alkyl-2 or 3-cephem-4-carboxylic acid derivatives and
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04113940A1

  公开（公告）日：1978-09-12

  A compound of the formula ##STR1## wherein R.sup.1 is amino or substituted amino, R.sup.2 is carboxy or protected carboxy, R.sup.3 is lower alkyl and X is --S-- or ##STR2## or a pharmaceutically acceptable salt thereof is effective against various microorganisms.

  该化合物的公式为##STR1##，其中R.sup.1是氨基或取代氨基，R.sup.2是羧基或保护羧基，R.sup.3是低级烷基，X是--S--或##STR2##，或其药物可接受的盐对各种微生物有效。

表征谱图