2-硝基噻吩 | 609-40-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-硝基噻吩
• 中文别名: 2-硝噻吩
• 英文名称: 2-nitrothiophene
• CAS: 609-40-5
• 化学式: C₄H₃NO₂S
• mdl: MFCD00005425
• 分子量: 129.139
• InChiKey: JIZRGGUCOQKGQD-UHFFFAOYSA-N

物化性质

• 熔点：
  43-45 °C (lit.)
• 沸点：
  224-225 °C (lit.)
• 密度：
  1,364 g/cm3
• 闪点：
  201 °F
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• LogP：
  1.55
• 稳定性/保质期：
  一、基本性质：能随水蒸气挥发。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• TSCA：
  T
• 危险品标志：
  Xn
• 安全说明：
  S24/25
• 危险类别码：
  R68
• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险品运输编号：
  OTH
• RTECS号：
  XN0030000
• 危险性防范说明：
  P501,P261,P270,P202,P201,P271,P264,P280,P308+P313,P362+P364,P301+P312+P330,P302+P352+P312,P304+P340+P312,P405
• 危险性描述：
  H302+H312+H332,H341
• 储存条件：
  贮存： 将密器密封后，储存在密封的主要容器中，并放置在阴凉、干燥的地方。

SDS

Name:	2-Nitrothiophene tech. 85% Material Safety Data Sheet
Synonym:	None
CAS:	609-40-5

Section 1 - Chemical Product MSDS Name:2-Nitrothiophene tech. 85% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
609-40-5	2-Nitrothiophene	85	210-190-9

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Light sensitive.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. 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. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate 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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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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. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Store protected from light.
Storage:
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances. Dark room.
Store protected from light.

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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# 609-40-5: 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 protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
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: Crystals
Color: yellow to beige-brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 224 - 225 deg C @ 760.00mmHg
Freezing/Melting Point: 43.00 - 45.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C4H3NO2S
Molecular Weight: 129.13

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures. May discolor on exposure to light.
Conditions to Avoid:
Incompatible materials, light, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents, strong bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 609-40-5: XN0030000 LD50/LC50:
Not available.
Carcinogenicity:
2-Nitrothiophene - 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.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 609-40-5: No information available.
Canada
CAS# 609-40-5 is listed on Canada's NDSL List.
CAS# 609-40-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 609-40-5 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
淡黄色结晶状物质，熔点为41℃，沸点在224-225℃之间，并能随水蒸气挥发。

用途
主要用于有机合成领域。

生产方法
将噻吩溶解于乙酐中，再将发烟硝酸溶于冰乙酸。两种溶液在约10℃时混合反应，生成的硝化物倾倒入碎冰中析出2-硝基噻吩，收率约为80%。

反应信息

• 作为反应物：
  描述：

  2-硝基噻吩 在 盐酸 、 tin 作用下， 生成 2-亚氨基-2,3-二氢-噻吩
  参考文献：
  名称：

  Stadler, Chemische Berichte, 1885, vol. 18, p. 1491,2316

  摘要：

  DOI：
• 作为产物：
  描述：

  2-噻吩基锂 在 dinitrogen tetraoxide 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到2-硝基噻吩
  参考文献：
  名称：

  Nitration of Organolithiums and Grignards with Dinitrogen Tetroxide:  Success at Melting Interfaces

  摘要：

  DOI：

  10.1021/ja963658e
• 作为试剂：
  描述：

  甘油 、 alkaline earth salt of/the/ methylsulfuric acid 在 2-硝基噻吩 、 硫酸 作用下， 生成 噻吩并[2,3-b]吡啶
  参考文献：
  名称：

  Steinkopf; Luetzkendorf, Justus Liebigs Annalen der Chemie, 1914, vol. 403, p. 48

  摘要：

  DOI：

文献信息

• Palladium-catalyzed four-component carbonylative synthesis of 2,3-disubstituted quinazolin-4(3H)-ones: Convenient methaqualone preparation
  作者：Jin-Bao Peng、Hui-Qing Geng、Wei Wang、Xinxin Qi、Jun Ying、Xiao-Feng Wu

  DOI：10.1016/j.jcat.2018.06.007

  日期：2018.9

  A palladium-catalyzed four-component carbonylative cyclization reaction for the synthesis of 2,3-disubstituted quinazolin-4(3H)-ones has been developed. A range of different 2,3-disubstituted quinazolin-4(3H)-one derivatives were prepared in moderate to good yields employing simple and readily accessible 2-iodoanilines, nitro compounds and acid anhydrides as the synthetic precursors. Mo(CO)6 acted

  已经开发了钯催化的四组分羰基环化反应，用于合成2,3-二取代的喹唑啉-4（3H）-one。使用简单且易于获得的2-碘苯胺，硝基化合物和酸酐作为合成前体，以中等至良好的产率制备了一系列不同的2,3-二取代的喹唑啉-4（3H）-one衍生物。Mo（CO）6既充当固体CO源又充当还原剂。值得注意的是，在我们的条件下，甲喹酮作为镇静剂和催眠药也可以很容易地制备，收率为68％（4b）。
• Pd-Catalyzed Silicon Hydride Reductions of Aromatic and Aliphatic Nitro Groups
  作者：Ronald J. Rahaim、Robert E. Maleczka

  DOI：10.1021/ol052120n

  日期：2005.10.1

  [reaction: see text] Room-temperature reduction of aromatic nitro groups to amines can be accomplished in high yield, with wide functional group tolerance and short reaction times (30 min) using a combination of palladium(II) acetate, aqueous potassium fluoride, and polymethylhydrosiloxane (PMHS). Replacing PMHS/KF with triethylsilane allows aliphatic nitro groups to be reduced to their hydroxylamines.

  [反应：参见正文]使用乙酸钯（II），氟化钾水溶液，和聚甲基氢硅氧烷（PMHS）。用三乙基硅烷代替PMHS / KF可使脂肪族硝基还原为羟胺。
• Vicarious nucleophilic substitution of hydrogen in nitroderivatives of five-membered heteroaromatic compounds
  作者：Mieczyslaw Makosza、Ewa Kwast

  DOI：10.1016/0040-4020(95)00445-e

  日期：1995.7

  Nitro derivatives of thiophene, furan and pyrrole react with carbanions containing leaving groups giving products of replacement of hydrogen with functionalized alkyl substituents. Many specific features of this reaction are discussed.

  噻吩，呋喃和吡咯的硝基衍生物与含有离去基团的碳负离子反应，生成被官能化的烷基取代基取代氢的产物。讨论了该反应的许多具体特征。
• Ultrasonically Assisted Rate Enhancements in Trichloroisocyanuric Acid/DMF/NaNO₂Triggered Nitration of Aromatic Compounds and Decarboxylative Nitration of<font>α</font>,<font>β</font>-Unsaturated Acids
  作者：Mukka Satish Kumar、Kamatala Chinna Rajanna、Marri Venkateswarlu、Purugula Venkanna、Pondichery Kuppuswamy Saiprakash

  DOI：10.1080/00397911.2015.1075044

  日期：2015.10.2

  Abstract An efficient and safe method for nitration of aromatic compounds and decarboxylative nitration of α,β-unsaturated acids was developed using trichloroisocyanuric acid (TCICA)/dimethylformamide (DMF) in the presence of NaNO2. The reaction times of conventional protocol reduced from 8–10 h to 1.0–1.5 h (60–90 min) under sonication, even though the yields are comparable under both the conditions

  摘要 采用三氯异氰脲酸(TCICA)/二甲基甲酰胺(DMF)，在NaNO2 存在下，开发了一种高效、安全的芳香族化合物硝化和α,β-不饱和酸脱羧硝化方法。传统方案的反应时间在超声处理下从 8-10 小时减少到 1.0-1.5 小时（60-90 分钟），尽管两种条件下的产量相当。图形概要
• Novel approach to synthesis of substituted 3-aminoquinolines from nitroarenes and protected ethyl aminocrotonate
  作者：Robert Bujok、Andrzej Kwast、Piotr Cmoch、Zbigniew Wróbel

  DOI：10.1016/j.tet.2009.11.060

  日期：2010.1

  The addition of mono- and dianions of ethyl N-pivaloyl-3-aminocrotonate to substituted nitroarenes, followed by action of silylating or acylating agent, leads to 3-aminoquinoline carboxylic acid derivatives. Hydrolysis and decarboxylation of the latter, carried out efficiently under relatively mild conditions, afford 3-aminoquinolines diversely substituted in the benzo-fused ring.

  将N-新戊酰基-3-氨基巴豆酸乙酯的单和二价阴离子加到取代的硝基芳烃上，然后甲硅烷基化或酰化剂作用，产生3-氨基喹啉羧酸衍生物。在相对温和的条件下有效地进行后者的水解和脱羧，得到在苯并稠合的环中被不同取代的3-氨基喹啉。

表征谱图