对甲苯磺酸 | 104-15-4

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸的卤化、磺化、硝化或亚硝化衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 对甲苯磺酸
• 中文别名: 4-甲苯磺酸；甲苯磺酸；对甲基苯磺酸；4-甲基苯磺酸；甲苯-4-磺酸
• 英文名称: toluene-4-sulfonic acid
• 英文别名: p-toluenesulphonic acid monohydrate；para-toluenesulphonic acid；Toluene-p-sulfonic acid；p-Toluenesulfonic acid；p-tolylsulfonic acid；pTSA；TsOH；p-TsOH；4-methylbenzenesulfonic acid；p-toluenesulfonic acid monohydrate；4-methylbenzene-1-sulfonic acid；para-toluenesulfonic acid；p-toluenesulphonic acid；4-toluenesulfonic acid；tosic acid；p-toluenesulfonic acid hydrate；p‐toluenesulfonic acid；p-methyl benzenesulfonic acid；toluenesulfonic acid；tosylic acid；Hydron;4-methylbenzenesulfonate
• CAS: 104-15-4
• 化学式: C₇H₈O₃S
• mdl: MFCD00064387
• 分子量: 172.205
• InChiKey: JOXIMZWYDAKGHI-UHFFFAOYSA-N

物化性质

• 熔点：
  106~107℃
• 沸点：
  116 °C
• 密度：
  1.07
• 闪点：
  41 °C
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• LogP：
  0.41 at 25℃
• 物理描述：
  Toluene sulfonic acid, liquid, with more than 5% free sulfuric acid appears as colorless to black solid. Odorless or nearly odorless. (USCG, 1999)
• 颜色/状态：
  MONOCLINIC LEAFLETS OR PRISMS
• 蒸汽压力：
  0.0000027 [mmHg]
• 稳定性/保质期：
  1. 该物质可与金属、强氧化剂、强碱、胺类、硝酸铵、三氟化氯、硝酸、高锰酸盐、过氧化钠、过氧化氢、乙醛以及多种酸（如矿物酸、氧化铬酸、次氯酸、硝酸和硫酸）发生反应。 2. 具有一定毒性，可刺激皮肤、眼睛及黏膜。实验数据显示，大鼠经口LD₅₀为2480毫克/千克，小鼠经口LD₅₀为400毫克/千克。其钠盐则无毒。生产过程中使用的甲苯具有毒性，可能损害人体肝脏、造血系统和神经系统。浓硫酸有极强的腐蚀性，因此在生产时应确保设备密封良好，防止泄漏，并要求操作人员穿戴防护装备。
• 解离常数：
  -1.34

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

产生3-甲基邻苯二酚的假单胞菌：Focht, DD & Williams, FD，《加拿大微生物学杂志》，16卷，309页（1970年）；产生4-甲基邻苯二酚的假单胞菌：Cain, RB & Farr, DR，《生物化学杂志》，106卷，859页（1968年）。/来自表格/

YIELDS 3-METHYLCATECHOL IN PSEUDOMONAS: FOCHT, DD & WILLIAMS, FD, CAN J MICROBIOL, 16, 309 (1970); YIELDS 4-METHYLCATECHOL IN PSEUDOMONAS: CAIN, RB & FARR, DR, BIOCHEM J. 106, 859 (1968). /FROM TABLE/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 暴露途径

所有暴露途径均可能产生严重的局部影响。

Serious local effects by all routes of exposure.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 吸入症状

喉咙痛。咳嗽。灼热感。呼吸困难。气短。

Sore throat. Cough. Burning sensation. Laboured breathing. Shortness of breath.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 皮肤症状

红肿。疼痛。严重皮肤烧伤。

Redness. Pain. Serious skin burns.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 眼睛症状

红斑。疼痛。烧伤。

Redness. Pain. Burns.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 摄入症状

喉咙痛。喉咙和胸部有灼热感。休克或晕厥。

Sore throat. Burning sensation in the throat and chest. Shock or collapse.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

吸收、分配和排泄

很可能会以对甲苯磺酸的形态被排出。/来自表格/

PROBABLY EXCRETED AS P-TOLUENESULFONIC ACID. /FROM TABLE/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

经口服或肠道外给药后，对甲苯磺酸盐在组织中均匀分布，除了大脑和脂肪组织。

FOLLOWING ORAL OR IP ADMIN, P-TOLUENESULFONATE WAS EVENLY DISTRIBUTED IN TISSUES, EXCEPT IN BRAIN & FAT TISSUES.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S23,S26,S45
• 危险类别码：
  R34,R10
• 海关编码：
  2904909090
• 危险品运输编号：
  2585
• 危险类别：
  8
• RTECS号：
  XT6300000
• 包装等级：
  III
• 储存条件：
  密封保存，存放在阴凉、干燥的地方，并远离火源。建议使用塑料袋外加木箱包装，然后存放于阴凉、通风、干燥处，并按照有毒化学品的规定进行储运。

SDS

Name:	p-Toluenesulfonic Acid Monohydrate Material Safety Data Sheet
Synonym:	Benzenesulfonic acid, 4-methyl-, monohydrate; Toluene, 4-sulfonic acid, monohydrate; PTSA monohydrate
CAS:	104-15-4

Section 1 - Chemical Product MSDS Name:p-Toluenesulfonic Acid Monohydrate Material Safety Data Sheet
Synonym:Benzenesulfonic acid, 4-methyl-, monohydrate; Toluene, 4-sulfonic acid, monohydrate; PTSA monohydrate

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
104-15-4	p-Toluenesulfonic acid monohydrate	> 97.5	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.Hygroscopic (absorbs moisture from the air).
Potential Health Effects
Eye:
Causes severe eye irritation and possible burns.
Skin:
Causes skin irritation. Not expected to cause an allergic skin reaction.
Ingestion:
May be harmful if swallowed.
Inhalation:
Dust is irritating to the respiratory tract.
Chronic:
Chronic exposure may cause effects similar to those of acute exposure.

---

Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid immediately.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

---

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. This material in sufficient quantity and reduced particle size is capable of creating a dust explosion. Contact with metals may evolve flammable hydrogen gas.
Extinguishing Media:
Use water spray, 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. Avoid generating dusty conditions. Provide ventilation.

---

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. Keep container tightly closed. Avoid breathing dust. Do not get in eyes. Avoid contact with skin and clothing.
Storage:
Store in a cool, dry, well-ventilated area away from incompatible substances.

---

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# 104-15-4: CAS# 6192-52-5: 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 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: white
Odor: none reported
pH: Not applicable.
Vapor Pressure: 0.0000027 mm Hg @ 25 deg C
Viscosity: Not available.
Boiling Point: 140 deg C @ 20 mmHg
Freezing/Melting Point: 103 deg C
Autoignition Temperature: 350 deg C ( 662.00 deg F)
Flash Point: 180 deg C ( 356.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Soluble.
Specific Gravity/Density: Not available.
Molecular Formula: C7H8O3S.H2O
Molecular Weight: 190.22

---

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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 104-15-4: XT6300000 CAS# 6192-52-5: DB7164000 LD50/LC50:
CAS# 104-15-4: Oral, rat: LD50 = 2480 mg/kg.
CAS# 6192-52-5: Oral, mouse: LD50 = 1683 mg/kg; Oral, rat: LD50 = 2570 mg/kg.
Skin absorption LD50 guinea pig: no evidence at 1.0 g/kg.
irritation, guinea pig: Moderate.
pig: Moderate exacerbation.
sensitize any animals tested.
Company) Carcinogenicity:
p-Toluenesulfonic acid anhydrous - Not listed by ACGIH, IARC, or NTP.
p-Toluenesulfonic acid monohydrate - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

---

Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: Fathead Minnow: > 100 mg/l; 96 hr; LC50

---

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

---

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: ARYLSULPHONIC ACIDS, SOLID
Hazard Class: 8
UN Number: 2585
Packing Group: III
IMO
Shipping Name: ARYLSULPHONIC ACIDS, SOLID
Hazard Class: 8
UN Number: 2585
Packing Group: III
RID/ADR
Shipping Name: ARYLSULPHONIC ACIDS, SOLID
Hazard Class: 8
UN Number: 2585
Packing group: III

---

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 Wear suitable gloves.
WGK (Water Danger/Protection)
CAS# 104-15-4: 1
CAS# 6192-52-5: 1
Canada
CAS# 104-15-4 is listed on Canada's DSL List.
CAS# 104-15-4 is not listed on Canada's Ingredient Disclosure List.
CAS# 6192-52-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 104-15-4 is listed on the TSCA inventory.
CAS# 6192-52-5 is not on the TSCA Inventory because it is a hydrate.
It is considered to be listed if the CAS number for the anhydrous form
is on the inventory (40CFR720.3(u)(2)).

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

概述

对甲苯磺酸（分子结构式：p-CH₃C₆H₄SO₃H，也写作TsOH，英文P-Toluene Sulfonic acid），简称PTS，是一个不具氧化性的有机强酸。它为白色针状或粉末状结晶，可溶于水、醇、醚和其他极性溶剂。对甲苯磺酸极易潮解，易使木材和棉织物脱水而碳化，难溶于苯和甲苯；在碱熔时会生成对甲酚。

用途

对甲苯磺酸广泛应用于医药合成、农药制造、聚合反应的稳定剂以及有机合成（如酯类等）的催化剂。它还是涂料中间体和树脂固化剂。对甲苯磺酸是常用的有机酸催化剂，用于制备对甲苯磺酸钠，并进一步与五氯化磷作用生成对甲苯磺酰氯，后者在亲核取代反应中发挥作用。

制备

工业上通过使用浓硫酸对甲苯进行磺化来制取对甲基苯磺酸。制得的对甲苯磺酸中可能含有少量苯磺酸和硫酸杂质，可通过将不纯样品置于浓盐酸中重结晶并共沸干燥以得到纯净产品。

参考质量标准

项目/指标	工业级	医药级	精制级	试剂级（化学纯）
含量（以C₇H₈O₃S·H₂O计，%）≥	90-93.0	96.0	97.0	98.0
游离酸（H₂SO₄，%）≤	3.0	0.7	0.5	0.1
水分（不包括结晶水，%）≤	4.0	3.5	2.5	1.5
铁（以Fe²⁺计，ppm）≤	50	30	30	10
灼烧残渣（%，/）		0.2	0.2	0.02
熔点（℃，/）				102-105
乙醇溶解试验	/	合格	合格	合格
水溶解试验	/	合格	合格	合格

化学性质

对甲苯磺酸为无色单斜片状或柱状晶体，易溶于乙醇和乙醚，稍溶于水和热苯。

用途

对甲苯磺酸用作化学试剂、染料及有机合成的中间体。它还用于洗涤剂、塑料、涂料等方面，并广泛应用于医药（如强力霉素）、农药（如三氯杀螨醇）等领域。

生产方法

对甲苯磺酸由对甲苯磺酰氯水解而得，也可通过甲苯为原料经硫酸磺化制备。

类别与特性

• 类别：腐蚀物品
• 毒性分级：低毒
• 急性毒性：口服-大鼠 LD₅₀: 2480 毫克/公斤
• 可燃性危险特性：可燃，火中放出有毒氧化硫气体
• 储运特性：库房通风低温干燥；与碱分开存放
• 灭火剂：雾状水、二氧化碳、泡沫

反应信息

• 作为反应物：
  描述：

  对甲苯磺酸 在 三苯基膦 作用下， 生成 4-甲苯硫酚
  参考文献：
  名称：

  在钛-Salan 催化剂上用 H2O2 催化对映选择性氧化大块烷基芳基硫醚

  摘要：

  报道了一种用过氧化氢以良好至高产率和对映选择性（高达 98.5% ee）氧化大体积（优选芳基苄基取代）硫醚的简单有效的催化程序。在串联立体会聚对映选择性氧化和动力学拆分过程中实现了高光学产率。通过改变浓度和温度可以找到亚砜产率和对映选择性之间的合理平衡。报道了用于制备更具立体选择性的催化剂的钛-salan 催化剂的改进合成。

  DOI：

  10.1002/ejoc.201100557
• 作为产物：
  描述：

  对甲苯磺酸甲酯 在 邻苯二甲酸二甲酯 、 水 作用下， 反应 3.0h， 生成 对甲苯磺酸
  参考文献：
  名称：

  Removal of alkyl alkanesulfonate esters from alkanesulfonic acids and other organic media

  摘要：

  提供了从水性或无水性组合物中去除烷基烷磺酸酯的方法。该发明提供了将化学式为RSO3R′的烷基烷磺酸酯转化为化学式为RSO3H的相应酸的方法。烷基烷磺酸酯存在于有机介质中，该介质可能含有大量水，也可能是无水或基本无水的。在某些实施例中，该发明提供了通过去除烷基烷磺酸酯来净化水性或无水烷磺酸的方法。

  公开号：

  US20060030725A1
• 作为试剂：
  描述：

  2-氨基吡啶 在 碘苯二乙酸 、 lanthanide(III)chloride heptahydrate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.08h， 生成 2-(cyclohexylamino)-2-oxo-1-(m-tolyl)ethyl diethyl phosphate
  参考文献：
  名称：

  基于TMV-CP的抗植物病毒α-酰胺磷酸衍生物的合理设计与发现

  摘要：

  烟草花叶病毒外壳蛋白（TMV-CP）对于病毒的复制、运动和传播以及宿主植物的免疫系统识别它是不可或缺的。它构成病毒颗粒的最外层，是病毒结构的重要组成部分。 TMV-CP 对于启动和延长病毒组装至关重要，在烟草花叶病毒 (TMV) 的自组装过程中发挥着至关重要的作用。该研究采用 TMV-CP 作为虚拟筛选的主要目标，从中获取了包含 43,417 种化合物的库，并被选为先导化合物。因此，设计并合成了一系列α-酰胺磷酸衍生物，表现出显着的抗TMV功效。发现合成的化合物有利于治疗 TMV，其疗效略优于宁南霉素 (NNM) (EC = 304.54 µg/mL)，EC 为 291.9 µg/mL。此外，其灭活活性 (EC = 63.2 µg/mL) 与 NNM (EC = 67.5 µg/mL) 相当，且具有与 NNM (EC = 219.7 µg/mL) 类似的保护活性 (EC = 228.9 µg/mL)。微量热分析表明

  DOI：

  10.1016/j.bioorg.2024.107415

文献信息

• [EN] BENZAMIDE OR BENZAMINE COMPOUNDS USEFUL AS ANTICANCER AGENTS FOR THE TREATMENT OF HUMAN CANCERS<br/>[FR] COMPOSÉS BENZAMIDE OU BENZAMINE À UTILISER EN TANT QU'ANTICANCÉREUX POUR LE TRAITEMENT DE CANCERS HUMAINS
  申请人：UNIV TEXAS

  公开号：WO2017007634A1

  公开（公告）日：2017-01-12

  The described invention provides small molecule anti-cancer compounds for treating tumors that respond to cholesterol biosynthesis inhibition. The compounds selectively inhibit the cholesterol biosynthetic pathway in tumor-derived cancer cells, but do not affect normally dividing cells.

  所描述的发明提供了用于治疗对胆固醇生物合成抑制作出反应的肿瘤的小分子抗癌化合物。这些化合物选择性地抑制肿瘤来源的癌细胞中的胆固醇生物合成途径，但不影响正常分裂的细胞。
• BENZOTHIOPHENE INHIBITORS OF RHO KINASE
  申请人：Kahraman Mehmet

  公开号：US20080021026A1

  公开（公告）日：2008-01-24

  The present invention relates to compounds and methods which may be useful as inhibitors of Rho kinase for the treatment or prevention of disease.

  本发明涉及化合物和方法，这些化合物和方法可能作为Rho激酶的抑制剂在治疗或预防疾病方面有用。
• SYNTHESIS OF CYCLIC AMIDINES
  申请人：Lentzen George

  公开号：US20110178292A1

  公开（公告）日：2011-07-21

  The invention relates to an innovative method for synthesis of cyclic amidines. The synthesis starts from a β-, γ- or δ-lactone which is twofold brominated. After esterification of the carboxyl function, the bromine atoms are nucleophilically substituted and the corresponding diamino compound is obtained. The ring closure to the cyclic amidine is accomplished subsequently by reaction with orthoester, imidate or thioimidate. Owing to interposing additional steps for recovery of the diamino compound in enantiomerically pure form, the enantiomers of the cyclic amidines can be stereoselectively synthesized.

  该发明涉及一种合成环氨基甲酸盐的创新方法。合成从β-、γ-或δ-内酯开始，该内酯经过双溴化。在羧基酯化后，溴原子被亲核取代，得到相应的二氨基化合物。随后通过与正酯、亚胺酯或硫代亚胺的反应实现环氨基甲酸盐的环闭合。由于插入额外步骤以以对映纯形式回收二氨基化合物，因此可以立体选择性地合成环氨基甲酸盐的对映体。
• N-type calcium channel blockers
  申请人：Pajouhesh Hassan

  公开号：US20050165065A1

  公开（公告）日：2005-07-28

  The invention relates to novel 3-amino pyrrolidine derivatives, as well as methods for modulating calcium channel activity and for treating conditions associated with calcium channel function. In particular, the compounds generally contain at least one benzhydril moiety, and are useful in treating conditions which benefit from blocking calcium ion channels.

  这项发明涉及新型3-氨基吡咯烷衍生物，以及调节钙通道活性和治疗与钙通道功能相关疾病的方法。具体来说，这些化合物通常至少含有一个苯基甲酰基团，可用于治疗受益于阻断钙离子通道的疾病。
• [EN] ACC INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'ACC ET UTILISATIONS ASSOCIÉES
  申请人：GILEAD APOLLO LLC

  公开号：WO2017075056A1

  公开（公告）日：2017-05-04

  The present invention provides compounds I and II useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.

  本发明提供了化合物I和II，这些化合物可用作乙酰辅酶A羧化酶（ACC）的抑制剂，以及它们的组合物和使用方法。

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