三甲基氢氧化锡 | 56-24-6

• 物质功能分类: 化学试剂
• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 中文名称: 三甲基氢氧化锡
• 中文别名: 羟基三甲基锡烷；三甲基锡醇
• 英文名称: trimethyltin(IV) hydroxide
• 英文别名: trimethyl tin hydroxide；trimethylstannanol；Trimethylzinnhydroxid；Me₃SnOH；trimethylstannol；hydroxyl(trimethyl)stannane；hydroxy(trimethyl)stannane；Trimethyl-hydroxy-stannan；Trimethyl-zinnhydroxyd；Me3SnOH；trimethylstannanylium;hydroxide
• CAS: 56-24-6
• 化学式: C₃H₁₀OSn
• 分子量: 180.822
• InChiKey: OJZNYUDKNVNEMV-UHFFFAOYSA-M

物化性质

• 熔点：
  118°C
• 沸点：
  80°C
• 闪点：
  26℃
• 溶解度：
  氯仿（可溶，超声处理）、甲醇（少量，超声处理）、水（少量溶解）
• 暴露限值：
  ACGIH: TWA 0.1 mg/m3; STEL 0.2 mg/m3 (Skin)NIOSH: IDLH 25 mg/m3; TWA 0.1 mg/m3

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  6.1
• 危险品标志：
  T+,N
• 安全说明：
  S1/2,S26,S27,S28,S45,S60,S61
• 危险类别码：
  R26/27/28,R50/53
• 包装等级：
  III
• 危险类别：
  6.1
• 危险品运输编号：
  UN 3146
• 储存条件：
  室温

SDS

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Section 1: Product Identification
Chemical Name: Trimethyltin hydroxide, 98%
CAS Registry Number: 56-24-6
Formula: (CH3)3SnOH
EINECS Number: none
Chemical Family: organotin compound
Synonym: Hydroxytrimethylstannane, Trimethylstannanol

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 56-24-6 100% 0.1mg/m3 0.1mg/m3

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Section 3: Hazards Identification
Organo tin compounds may act as delayed poisons, causing headache, dizziness; psycho-neurologic
Emergency Overview:
disturbances; sore throat, vomiting; urine retention; vision impairment; skin burns, liver and kidney damage.
Primary Routes of Exposure: Ingestion, inhalation, skin, eyes
Eye Contact: Causes severe irritation of the eyes.
Harmful in contact with skin. Causes light to mild irritation. prolonged contact may dry the skin and lead to
Skin Contact:
rashes or more severe irritation.
Harmful by inhalation. Irritating to the nose, mucous membranes and respiratory tract. High doses may cause
Inhalation:
long-term neurological damage.
Harmful if swallowed. may cause delayed and permanent psycho-neurological disturbances, impairment of
Ingestion:
vision, unsteadiness, nausea and vomiting.
Harmful by inhalation, in contact with skin and if swallowed. Irritating to skin, eyes and respiratory tract.
Acute Health Affects:
Ingestion may cause delayed poisoning with cerebral edema.
Repeated exposure to certain organic tin compounds may cause problems with vision, skin, respiratory
Chronic Health Affects:
system, central nervous system, liver, kidneys, urinary tract, and blood.
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: no data
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: carbon dioxide or dry powder
Fire fighters should be equipped with a NIOSH approved positive pressure self-contained breathing apparatus
Special Fire Fighting Procedures:
and full protective clothing.
Hazardous Combustion and carbon monoxide, carbon dioxide, soot, organic fumes and tin compounds.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Small spills can be mixed with vermiculite, ground limestone, sodium carbonate or other suitable
Spill and Leak Procedures:
noncombustible adsorbent and swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store in a cool, dry, well ventilated area away from heat and direct sunlight. Keep containers tightly sealed.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves. Consult with glove manufacturer to determine the proper type of glove.
Ventilation: Work with this product in a well-ventilated area, preferably a fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Work with this product in a well-ventilated area, preferably a fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: white pwdr.
Molecular Weight: 180.8
Melting Point: 118°
Boiling Point: 80°C subl.
Vapor Pressure: no data
Specific Gravity: no data
Odor: pungent
Solubility in Water: soluble

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SECTION 10: Stability and Reactivity
Stability: air sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: none
Incompatibility: strong oxidizing agents and halogens
Decomposition Products: carbon monoxide, carbon dioxide, tin oxide, and organic fumes.

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SECTION 11: Toxicological Information
RTECS Data: Subcutaneous (mouse); LDLo: 1800 ug/kg.
Carcinogenic Effects: No data available
Mutagenic Effects: No data available
Tetratogenic Effects: No data available

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SECTION 12: Ecological Information
Avoid release to the environment. Very toxic to aquatic organisms. May cause long-term adverse effects in the
Ecological Information:
aquatic environment.

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SECTION 13: Disposal Considerations
Disposal: Dispose of according to federal, state, and local regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory.
SARA (Title 313): Title compound not listed.
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

三甲基氢氧化锡在常温常压下呈现白色固体粉末状，属于有机锡试剂，可用作有机合成反应和医药化学中间体。它广泛应用于药物分子、生物活性分子以及农药分子的合成。

合成方法

将干燥的反应烧瓶中加入三甲基氯化锡（370 mg）和无水甲醇（5 mL），然后向所得反应溶液中慢慢加入氢氧化钾固体（104 mg，1.9 mmol）。在环境温度下搅拌反应1小时后，可以明显观察到氯化钾固体析出。反应结束后，过滤掉氯化钾固体沉淀，并将含有产物的滤液在真空条件下减压蒸发浓缩，从而得到目标产物分子三甲基氢氧化锡。

危害

三甲基氢氧化锡具有高毒性，误食或皮肤直接接触均对身体造成极大伤害。特别是在高温下，它有一定的挥发性，使用时需格外注意安全，并采取适当的防护措施。

概述

三甲基氢氧化锡是一种化学试剂，其化学式为Me3SnOH，可用于全合成丹参酚酸A。

反应信息

• 作为反应物：
  描述：

  三甲基氢氧化锡 在 尿素 作用下， 以 neat (no solvent) 为溶剂， 生成 Trimethylzinnisocyanat
  参考文献：
  名称：

  Sedel'nikova, V. N.; Lopatin, M. A.; Sennikov, P. G., Journal of general chemistry of the USSR, 1984, vol. 54, p. 1404 - 1408

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(三甲基锡烷基)萘 以 甲醇 为溶剂， 生成 三甲基氢氧化锡
  参考文献：
  名称：

  芳香反应性。第XXXV部分。芳基三甲基锡的碱裂解：一种不寻常的亲电芳族取代

  摘要：

  我们通过分光光度法测量了一系列X·C 6 H 4 ·SnMe 3化合物中芳基-锡键的甲醇碱水溶液的裂解速率。在该反应中，确定速率的步骤可能涉及分离碳负离子X·C 6 H 4 –，间位取代基的作用与Hammettσ常数（σ= 2·18）一致，但对位取代基显示异常图案。例如，不仅通过诸如p -CF 3和p -Cl的吸电子基团，而且通过诸如p -OMe和p -NMe 2。对于对位取代基时，效果大致与它们线σ 1周的常数。

  DOI：

  10.1039/j29670001036
• 作为试剂：
  描述：

  methyl 5-hydroxy-4-iodo-6-oxopyran-2-carboxylate 在 偶氮二甲酸二叔丁酯 、 三苯基膦 、 三甲基氢氧化锡 作用下， 以 四氢呋喃 为溶剂， 反应 16.17h， 生成 5-[2-(tert-butoxy)ethoxy]-4-iodo-6-oxopyran-2-carboxylic acid
  参考文献：
  名称：

  THIADIAZOLE DERIVATIVES AS INHIBITORS OF CYCLIC GMP-AMP SYNTHASE AND USES THEREOF

  摘要：

  The present disclosure relates to compounds of Formula (I): (I) or a pharmaceutically acceptable salt thereof, wherein Ring A, R1, R2, R3, R4, and m are described herein, methods of preparation, methods of treatment, and pharmaceutical compositions comprising same. The present disclosure further relates to the use of the compounds of Formula (I), and pharmaceutically acceptable salts thereof, in the treatment of cGAS-related diseases and disorders.

  公开号：

  WO2024137607A1

文献信息

• New organotin(IV) ascorbates: synthesis, spectral characterization, biological and potentiometric studies
  作者：Mala Nath、Ruchi Jairath、George Eng、Xueqing Song、Ashok Kumar

  DOI：10.1016/j.saa.2004.03.018

  日期：2005.1

  structure with octahedral geometry around tin with trans organic groups has been tentatively proposed. The complexes have been assayed for their anti-inflammatory and cardiovascular activity. Ph(2)Sn(Asc) has been found to show the highest activity among the studied complexes. It is suggested on the basis of potentiometric studies of Me(2)Sn(IV) and Me(3)Sn(IV) systems with L-ascorbic acid that under

  通式R（3）Sn（HAsc）（其中R = Me，n-Pr，n-Bu和Ph）和R（2）Sn（Asc）（其中R = n-Bu）的新有机锡（IV）抗坏血酸通过R（n）SnCl（4-n）（其中n = 2或3）与抗坏血酸单钠的反应合成了α和β）。在紫外-可见，红外，远红外，（1）H和（13）C NMR以及（119）Sn Mossbauer光谱研究的基础上，讨论了这些配合物中的键合和配位行为。L-抗坏血酸充当R（3）Sn（HAsc）通过O（1）和O（3）配位的单阴离子二齿配体。Mossbauer研究以及IR和NMR研究表明，对于这些聚合物衍生物，多面体为锡周围的三角双锥体，赤道位置具有三个有机基团。在R（2）Sn（Asc）中，L-抗坏血酸起双齿四齿配体的作用，并已尝试性地提出了一种具有围绕锡的八面体几何结构和反式有机基团的聚合物结构。已经测定了复合物的抗炎和心血管活性。已发现Ph（2）Sn（Asc）在
• Preparation and structure of triorganotin, triorganolead and tetraphenylantimony derivatives of acetylenedicarboxylic acid, terephthalic acid and dithioterephthalic acid
  作者：A. Glowacki、F. Huber、H. Preut

  DOI：10.1002/recl.19881070333

  日期：——

  Triorganotin, triorganolead and tetraphenylantimony derivatives of acetylenedicarboxylic acid (H2ADC), terephthalic acid (H2TER) and dithioterephthalic acid (H2DTT) (R3M)2X (M = Sn, Pb; R = Me, Ph; X = ADC, TER, DTT) and (Ph4Sb)2X (X = ADC, TER) were prepared by neutralization of R3MOH or Ph4SbOH with the appropriate acid (X = ADC, DTT) or by reaction of R3MCl or Ph4SbCl with K2TER. The crystal structures

  乙炔二羧酸（H 2 ADC），对苯二甲酸（H 2 TER）和二硫代对苯二甲酸（H 2 DTT）（R 3 M）2 X的三有机锡，三有机油和四苯基锑衍生物（M = Sn，Pb; R = Me，Ph; X = ADC，TER，DTT和（Ph 4 Sb）2 X（X = ADC，TER）通过用适当的酸（X = ADC，DTT）中和R 3 MOH或Ph 4 SbOH或通过与R 3 MCl或带有K 2 TER的Ph 4 SbCl 。（Me 3 Sn）2 ADC和（Me 3 Sn）2的晶体结构TER通过X射线衍射测定。Sn原子处于稍微变形的三角双锥体环境中，C（Me）位于赤道平面，O（羧基）位于顶端。羧酸酯基桥接，导致形成折叠的22元[（Me 3 Sn）2 ADC]和26元[（Me 3 Sn）2 TER]环的二维聚合物。从振动光谱推断出固体（Ph 3 Sn）2 ADC，（R 3 Pb）2 ADC（R = Me，Ph）和（Me
• [EN] ORGANOTIN(IV) COMPLEXES WITH N-ACETYLCYSTEINE POSSESSING ANTITUMORAL ACTIVITY, PROCESS FOR THEIR PRODUCTION AND THEIR USE<br/>[FR] COMPLEXES D'ORGANOÉTAIN(IV) AVEC LA N-ACÉTYLCYSTÉINE POSSÉDANT UNE ACTIVITÉ ANTITUMORALE, LEUR PROCÉDÉ DE FABRICATION ET LEUR UTILISATION
  申请人：UNIV PALERMO

  公开号：WO2010015590A1

  公开（公告）日：2010-02-11

  Organotin(IV) compounds with N-acetylcysteine having the general formula (1 ) o (2): wherein: R1, R2 and R3 are each independently selected from the group consisting of : H, an alkyl, alkoxyl, alkenyl or alkynyl group with up to 12 carbon atoms, an isocyclic or heterocyclic aromatic or aralkyl group with up to 12 carbon atoms, and they are preferably chosen from methyl, ethyl, butyl or phenyl, are synthetized by simple procedures from commercial products, and are active as anticancer agents. In particular, the Bu2Sn-N-acetylcysteinate derivative was found to have a potent and selective anticancer activity in vitro against several cancer cell lines.

  有机锡（IV）化合物与N-乙酰半胱氨酸具有通式（1）o（2）：其中：R1、R2和R3分别独立地选自以下组：H，具有多达12个碳原子的烷基，烷氧基，烯基或炔基，具有多达12个碳原子的异环芳香族或杂环芳香族或芳基，它们优选选自甲基，乙基，丁基或苯基，通过简单的程序从商业产品合成，并且作为抗癌剂活性。特别是发现Bu2Sn-N-乙酰半胱氨酸酯衍生物在体外对几种癌细胞系具有强效和选择性的抗癌活性。
• Triorganotin 4-isopropylbenzoates as model transesterification catalysts for triorganotin carboxylates grafted to cross-linked polystyrene
  作者：Luigi Angiolini、Daniele Caretti、Laura Mazzocchetti、Elisabetta Salatelli、Rudolph Willem、Monique Biesemans

  DOI：10.1016/j.jorganchem.2006.01.002

  日期：2006.4

  the reaction between ethyl acetate and primary, secondary or tertiary alcohol, respectively, displayed, as expected, a strong decrease of activity on passing from the primary to the tertiary alcohol reactant. Different activities by the tin carboxylates were also observed in the reaction between primary alcohol and ethyl acetate. The reaction mechanism, as elucidated by Sn NMR, involves coordination

  从4-异丙基苯甲酸开始，分别制备了三种在锡上分别带有甲基，丁基和苯基取代基的三有机锡羧酸盐，并通过光谱和热技术对其进行了全面表征，特别是考虑到溶液中锡原子的配位数以及在固态。分别在乙酸乙酯与伯醇，仲醇或叔醇之间的反应中作为酯交换催化剂测试的三有机锡化合物，按预期显示出从伯醇到叔醇反应物传递时活性大大降低。在伯醇与乙酸乙酯之间的反应中还观察到了羧酸锡的不同活性。通过Sn NMR阐明了反应机理，涉及酯底物和醇反应物与三有机锡化合物的配位，反应的转化不仅与锡原子的路易斯酸度有关，而且与反应物的性质有关。还对十三十二酸甘油酯（作为天然甘油三酸酯的模型）与乙醇之间的反应进行了初步的催化测试，以模拟生物柴油燃料的制备。尽管在这种情况下，相对于在乙酸乙酯上的反应获得了较低的转化率，但是有机锡衍生物的催化活性似乎相当大。还对十三十二酸甘油酯（作为天然甘油三酸酯的模型）与乙醇之间的反应进行了初步的催化测试，
• Structural studies in main group chemistry
  作者：Philip G. Harrison、John A. Richards

  DOI：10.1016/s0022-328x(00)94399-7

  日期：1980.1

  The tin derivatives of N-acylhydroxylamines, (CH3)2Sn[ON(CH3)COCH3], R2Sn[ON(Ph)COPh]2 (R  CH3, PH, n-C4H9, n-C8H17), n-C4H9Sn[ON(Ph)COPh]3, (CH3)3Sn[ON(Ph)SO2C6H4CH3], X2Sn[ON(E)COPh]2 (X  Cl, Br, I; E  H, Ph), (CH3)2SnX[ON(Ph)COPh] (X  Cl, Br, I); Cl2Sn[ON(CH3)COCH3]2 have been prepared. The reaction of N-acetyl-N-methylhydroxylamine with hexamethyldisilazane yielded the trimethylsilyl hydrazine

  N-酰基羟胺，（CH 3）2 Sn [ON（CH 3）COCH 3 ]，R 2 Sn [ON（Ph）COPh] 2（RCH 3，PH，nC 4 H 9，nC 8的锡衍生物H 17），nC 4 H 9 Sn [ON（Ph）COPh] 3，（CH 3）3 Sn [ON（Ph）SO 2 C 6 H 4 CH 3 ]，X 2 Sn [ON（E）COPh] 2（XCl，Br，I; EH，Ph），（CH 3）2 SnX [ON（Ph）COPh]（XCl，Br，I）; 已经制备了Cl 2 Sn [ON（CH 3）COCH 3 ] 2。N-乙酰基-N-甲基羟胺与六甲基二硅氮烷的反应产生三甲基甲硅烷基肼，（CH 3）3 SiNH-N（CH 3）COCH 3。从尝试的三有机锡衍生物的几种合成中，仅分离出歧化产物，特别是（CH 3）3 Sn [（ON（CH 3）COCH 3 ]，其可从羟胺和（CH 3）