邻氯苯基硫脲 | 5344-82-1

• 物质功能分类: 化学试剂 - 有机试剂 - 硫脲
• 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: 邻氯苯基硫脲
• 中文别名: 1-(2-氯苯基)-2-硫脲；2-氯苯基硫脲
• 英文名称: o-chlorophenylthiourea
• 英文别名: 1-(2-chlorophenyl)-2-thiourea；1-(2-chlorophenyl)thiourea；(2-chlorophenyl)thiourea
• CAS: 5344-82-1
• 化学式: C₇H₇ClN₂S
• mdl: MFCD00004934
• 分子量: 186.665
• InChiKey: YZUKKTCDYSIWKJ-UHFFFAOYSA-N

物化性质

• 熔点：
  144-149 °C
• 沸点：
  250°C (rough estimate)
• 密度：
  1.4179 (rough estimate)
• 物理描述：
  Thiourea, (2-chlorophenyl)- appears as needles or plates. Used as an herbicide. Not registered as a pesticide in the U.S. (EPA, 1998)
• 颜色/状态：
  NEEDLES OR PLATES
• 溶解度：
  VERY SOL IN WATER; SLIGHTLY SOL IN AMMONIA
• 稳定性/保质期：
  常温常压下稳定，本品为白色或淡黄色固体，熔点143～146℃，易溶于乙醇和水。

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  1

ADMET

毒理性

• 人类毒性摘录

在橡胶制造过程中，可能会因接触过程中使用的各种酸、碱、洗涤剂和溶剂而发生刺激性接触性皮炎。过敏性接触性皮炎也并不少见，几乎总是由有机加速剂或抗氧化剂引起。尽管潜在的致敏加速剂和抗氧化剂的清单非常庞大，但常见的过敏原包括......硫脲类。/硫脲类/

In the manufacture of rubber, irritant contact dermatitis may occur from a variety of acids, alkalies, detergents, and solvents used in the process. Allergic contact dermatitis occurs not infrequently and is almost always due to an organic accelerator or antioxidant. While the list of potential sensitizing accelerators and antioxidants is enormous, common allergens include ... thioureas. /Thioureas/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

N-芳基硫脲衍生物，包括2-氯苯基硫脲，已经制备、分析和测试了它们对来自干豌豆种子（Pisum sativum）的脱氢酶的抑制效果。由Cl-取代引起的抑制效果大于甲基取代。

N-ARYLTHIOUREA DERIVATIVES, INCLUDING 2-CHLOROPHENYLTHIOUREA, WERE PREPARED, ANALYZED & TESTED FOR THEIR INHIBITORY EFFECT ON DEHYDROGENASE, ISOLATED FROM DRIED PEA SEEDS (PISUM SATIVUM). THE INHIBITORY EFFECTS CAUSED BY CL-SUBSTITUTION WAS GREATER THAN THAT OF METHYL SUBSTITUTION.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

取代的硫脲，包括2-氯苯基硫脲，以浓度依赖性的方式抑制了小球藻同步培养的生长。对于间位、对位和邻位衍生物发现了两种不同的功能。这些功能允许预测不同取代基在硫脲中的除草效果。增加这些化合物的疏水特性会增强其除草活性。

ARYLATED THIOUREAS, INCLUDING 2-CHLOROPHENYLTHIOUREA, INHIBITED THE GROWTH OF SYNCHRONIZED CULTURES OF CHLORELLA VULGARIS IN A CONCN DEPENDENT MANNER. TWO SEPARATE FUNCTIONS WERE FOUND FOR META-, PARA- & ORTHO DERIVATIVES. THE FUNCTIONS PERMIT FORECASTING THE HERBICIDAL EFFECTIVENESS OF DIFFERENT SUBSTITUENTS IN THE THIOUREAS. INCREASING THE HYDROPHOBIC CHARACTER OF THESE CMPD ENHANCES THE HERBICIDAL ACTIVITY.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1
• 危险品标志：
  T+
• 安全说明：
  S1,S28A,S45
• 危险类别码：
  R28
• 海关编码：
  2930909090
• 危险品运输编号：
  2811
• RTECS号：
  YS7100000
• 包装等级：
  II
• 危险类别：
  6.1
• 危险性防范说明：
  P264,P270,P301+P310,P330,P405,P501
• 危险性描述：
  H300
• 储存条件：
  避光，存于阴凉干燥处，并密封保存。

SDS

Name:	1-(2-Chlorophenyl)-2-thiourea 98% Material Safety Data Sheet
Synonym:
CAS:	5344-82-1

Section 1 - Chemical Product MSDS Name:1-(2-Chlorophenyl)-2-thiourea 98% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5344-82-1	1-(2-Chlorophenyl)-2-thiourea	98%	226-291-6

Hazard Symbols: T+
Risk Phrases: 28

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Very toxic if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May be fatal if swallowed. May cause irritation of the digestive tract.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

---

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. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid immediately. Wash mouth out with water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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.
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:
Vacuum or sweep up material and place into a suitable disposal container.

---

Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Poison room locked.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 5344-82-1: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white to tan
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 143 - 146 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C7H7ClN2S
Molecular Weight: 186.66

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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, strong acids, strong bases.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide, sulfur oxides (SOx), including sulfur oxide and sulfur dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5344-82-1: YS7100000 LD50/LC50:
CAS# 5344-82-1: Oral, rat: LD50 = 4600 ug/kg.
Carcinogenicity:
1-(2-Chlorophenyl)-2-thiourea - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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.

---

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: II
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: II
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: II
USA RQ: CAS# 5344-82-1: 100 lb final RQ; 45.4 kg final RQ

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T+
Risk Phrases:
R 28 Very toxic if swallowed.
Safety Phrases:
S 1 Keep locked up.
S 28A After contact with skin, wash immediately with
plenty of water.
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# 5344-82-1: No information available.
Canada
CAS# 5344-82-1 is listed on Canada's NDSL List.
CAS# 5344-82-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5344-82-1 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质
本品为白色或淡黄色固体，熔点为143～146℃，易溶于乙醇和水。

用途
邻氯苯基硫脲是除草剂草除灵的中间体。

生产方法
其制备方法是在反应锅中加入邻氯苯胺和水，再滴加硫酸，并将温度控制在50℃以下，反应约0.5小时后搅拌0.5小时。随后加入硫氰化铵并搅拌升温回流20小时。反应结束后进行过滤、干燥得产品。

反应信息

• 作为反应物：
  描述：

  邻氯苯基硫脲 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 1-(2-chlorophenyl)-4,6-dimethyl-2-(methylthio)pyrimidin-1-ium methyl sulfate
  参考文献：
  名称：

  Korohoda, Maria Jolanta; Slomska, Elzbieta; Szczurek, Halina, Polish Journal of Chemistry, 1989, vol. 63, # 1-3, p. 165 - 171

  摘要：

  DOI：
• 作为产物：
  描述：

  2-chlorophenyl dithiocarbamic acid triethylammonium 在 1,2-dipyridinium ditribromide ethane 、 氨 作用下， 以 水 、 乙腈 为溶剂， 生成 邻氯苯基硫脲
  参考文献：
  名称：

  无溴溴作为一种高效脱硫剂，用于从二硫代氨基甲酸盐制备氰胺和 2-氨基噻唑

  摘要：

  摘要 在以二硫代氨基甲酸为原料制备有机氰胺和取代噻唑的过程中，无溴溴化试剂 1,1'-(乙烷-1,2-二基)二溴化吡啶鎓 (EDPBT) 已被用作脱硫剂。盐。在这种方法中，烷基/芳基异硫氰酸酯首先通过二硫代氨基甲酸盐与 EDPBT 脱硫获得。原位生成的异硫氰酸酯与氨水反应，形成烷基或芳基硫脲，随后用 EDPBT 氧化脱硫，以良好的收率形成相应的氰胺。或者，通过原位生成的 1-芳基硫脲与由酮原位生成的 α-溴酮缩合，再次使用 EDPBT，实现了取代噻唑的高效一锅法合成。试剂 EDPBT 可以很容易地从现成的试剂中制备。对于易于溴化的底物，脱硫能力优于其溴化能力。

  DOI：

  10.1080/00397911003642658
• 作为试剂：
  描述：

  1-(4-氯苯基)-2-硝基乙烯 、 (benzoylmethylene)dimethylsulfurane 在 4-二甲氨基吡啶 、 1,1'-((1R,2R)-1,2-diphenylethane-1,2-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl)urea) 、 邻氯苯基硫脲 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 120.5h， 以80%的产率得到trans-5-benzoyl-4-(4-chlorophenyl)oxazolidin-2-one
  参考文献：
  名称：

  氢键介导的稳定硫叶立德与硝基烯烃的不对称级联反应：范围，应用和机理

  摘要：

  氢键介导的不对称[4 + 1]环化/重排的级联稳定的硫磺化物和硝基烯烃被开发出来。该反应以中等至优异的分离产率（65-96％）和优异的立体控制（高达95：5 dr和97：3 er以上）提供了一条途径，可轻松获得对映体富集的4,5-取代的恶唑烷酮。该方法已成功应用于两个生物活性分子的简明合成。已经提出了立体控制的模式和机理来解释这种立体化学的起源。

  DOI：

  10.1002/chem.201104021

文献信息

• 一种抗菌增效剂及其制法和用途
  申请人：上海医药工业研究院

  公开号：CN107629022A

  公开（公告）日：2018-01-26

  本发明涉及一种抗菌增效剂及其制法和用途。具体地，本发明公开了式(I)所示的具有抗菌增效活性的化合物或其光学异构体、顺反异构体或医药学上可接受的盐，及其制备方法。本发明还公开了包含上述化合物的医用组合物及其用途。上述化合物可有效增强多粘菌素B对鲍曼不动杆菌与肺炎克雷伯菌的抗菌活性，并可应用于对多粘菌素不敏感或抑菌活性不强的病菌的抗菌治疗。
• Substituted <i>N</i>-Phenylisothioureas:  Potent Inhibitors of Human Nitric Oxide Synthase with Neuronal Isoform Selectivity
  作者：Barry G. Shearer、Shuliang Lee、Jeffrey A. Oplinger、Lloyd W. Frick、Edward P. Garvey、Eric S. Furfine

  DOI：10.1021/jm960785c

  日期：1997.6.1

  has been found to be a potent inhibitor of both the human constitutive and inducible isoforms of nitric oxide synthase. A series of substituted N-phenylisothiourea analogues was synthesized to investigate the structure-activity relationship of this class of inhibitor. Each analogue was evaluated for human isoform selectivity. One analogue, S-ethyl N-[4-(trifluoromethyl)phenyl]isothiourea (39), exhibited

  已经发现S-乙基N-苯基异硫脲（4）是一氧化氮合酶的人组成型和诱导型同工型的有效抑制剂。合成了一系列取代的N-苯基异硫脲类似物，以研究这类抑制剂的构效关系。评价每种类似物的人同工型选择性。一种类似物S-乙基N- [4-（三氟甲基）苯基]异硫脲（39）对神经元同工型的诱导选择性和对内皮衍生的组成型同工型的选择性分别为115倍和29倍。研究表明，取代的N-苯基异硫脲39与L-精氨酸竞争性结合。
• Synthesis and biological evaluation of 3-amino-1,2,4-triazole derivatives as potential anticancer compounds
  作者：Oleksandr Grytsai、Oksana Valiashko、Manon Penco-Campillo、Maeva Dufies、Anais Hagege、Luc Demange、Sonia Martial、Gilles Pagès、Cyril Ronco、Rachid Benhida

  DOI：10.1016/j.bioorg.2020.104271

  日期：2020.11

  Two series of compounds carrying 3-amino-1,2,4-triazole scaffold were synthesized and evaluated for their anticancer activity against a panel of cancer cell lines using XTT assay. The 1,2,4-triazole synthesis was revisited for the first series of pyridyl derivatives. The biological results revealed the efficiency of the 3-amino-1,2,4-triazole core that could not be replaced and a clear beneficial effect

  合成了携带3-氨基-1,2,4-三唑支架的两个系列的化合物，并使用XTT分析评估了它们对一组癌细胞系的抗癌活性。重新讨论了第一批吡啶基衍生物的1,2,4-三唑合成。生物学结果表明，对于这两个系列，不能替代的3-氨基-1,2,4-三唑核的有效性以及在三唑的3位的3-溴苯基氨基部分具有明显的有益作用（化合物2.6和4.6）在多个测试的细胞系上。此外，我们的结果指出了这些化合物的抗血管生成活性。总体而言，5-芳基-3-苯基氨基-1,2,4-三唑结构具有有前途的双重抗癌活性。
• Synthesis of 2-aminothiazoles via rhodium-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas
  作者：Yuncan Chen、Shan Lv、Ruizhi Lai、Yingying Xu、Xin Huang、Jianglian Li、Guanghui Lv、Yong Wu

  DOI：10.1016/j.cclet.2021.02.052

  日期：2021.8

  Sulfoxonium ylides as carbene precursors couple smoothly with thioureas in the presence of 5 mol% of rhodium(II) acetate dimmer via carbenoid insertion to afford the corresponding 2-aminothiazoles with high chemoselectivity, providing a facile and efficient approach to access a variety of 2-aminothiazole derivatives with good functional groups tolerance.

  在 5 mol% 的乙酸铑（II）二聚体的存在下，作为卡宾前体的磺基叶立德通过卡宾插入提供了相应的具有高化学选择性的 2-氨基噻唑，提供了一种简单有效的方法来获得各种 2-具有良好官能团耐受性的氨基噻唑衍生物。
• Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists
  作者：Chetna Kharbanda、Mohammad Sarwar Alam、Hinna Hamid、Kalim Javed、Sameena Bano、Yakub Ali、Abhijeet Dhulap、Perwez Alam、M. A. Qadar Pasha

  DOI：10.1111/cbdd.12760

  日期：2016.9

  Piperine is an alkaloid responsible for the pungency of black pepper. In this study, piperine isolated from Piper nigrum L. was hydrolyzed under basic condition to obtain piperic acid and was used as precursor to carry out the synthesis of twenty piperine derivatives containing benzothiazole moiety. All the benzothiazole derivatives were evaluated for their antidiabetic potential by OGT test followed by

  胡椒碱是负责黑胡椒辛辣的生物碱。在这项研究中，从分离胡椒碱胡椒L.碱性条件下进行水解，得到胡椒酸和用作前体进行含有苯并噻唑部分20个胡椒碱衍生物的合成。通过OGT试验评估所有苯并噻唑衍生物的抗糖尿病潜力，然后在STZ诱导的糖尿病模型中评估活性衍生物。观察到二十种新型胡椒碱类似物中有九种（5b，6a-h）与罗格列酮（标准品）相比，具有明显更高的抗糖尿病活性。此外，评估了这些活性衍生物作为PPAR-γ激动剂的作用，证明了其作用机理。还研究了服用活性衍生物后对体重，脂质过氧化和肝毒性的影响，以进一步确立这些衍生物作为治疗糖尿病副作用较小的先导分子。

表征谱图