Thiophene 噻吩

CAS 110-02-1 MFCD00005413

化学结构图

110-02-1
SMILES: c1ccsc1

化学属性

Mol. FormulaC4H4S
Mol. Weight84
Refractive index1.5250 to 1.5300
Boiling Point84
Density1.063
Melting Point-38
Flash Point-1°C(lit.)
TSCAYes
Autoignition Point743 °F
Vapor Density2.9 (vs air)
Vapor Pressure40 mmHg ( 12.5 °C)
Solubility不溶于水,可混溶于乙醇、乙醚等多数有机溶剂。
Appearance powder
pH:A

别名和识别编码

Chemical NameThiophene
Synonym AKOS BBS-00004417 C4H4S (thiophene) CP 34 Divinylene sulfide Hopkin's lactic acid reagent Huile H50 Huile HSO THIOFURAN THIOLE THIOTETROLE Thiacyclopentadiene Thiaphene Thiofen Thiofuram Thiofuran Thiofurfuran Thiole Thiophen Thiotetrole USAF EK-1860 huilehso thio-fura 一硫二烯五环 一硫二烯五环,硫代呋喃,硫杂茂,硫茂,硫杂环戊二烯 噻吩 硫(杂)戊 硫(杂)茂 硫杂环戌二烯 硫杂茂 硫茂
Beilstein Registry Number103222
CAS Number110-02-1
PubChem Substance ID8030
EC Number203-729-4
MDL NumberMFCD00005413
Reaxys-RN103222
Merck Number9353
Chemical Name Translation噻吩
Wiswesser Line NotationT5SJ
LabNetwork Molecule IDLN00195288
InChIInChI=1S/C4H4S/c1-2-4-5-3-1/h1-4H
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分类

  • {S
  • {SNA} Alpha Sort, Analytical Standards, Analytical/Chromatography, Chromatography, Environmental Standards, T-Z, Volatiles/ Semivolatiles
  • {SNA} Building Blocks, C4 to C6, Chemical Synthesis, Heterocyclic Building Blocks, Thiophenes
  • {uni_hamburg} no charge; sulfur heterocycle; aromatic; 5ring; sulfide; 1fragment
  • {SNA} Additional Standards, Alpha Sort, Analytical Standards, Chromatography, Environmental Standards, Organic Pollutant Standards, Q-Z, T-Z, Volatile & Semivolatile Standards, Volatiles/ Semivolatiles, 分析/色谱
  • Alpha Sort, Alphabetic, Analytical Standards,

产品应用

  • 用作溶剂、色谱分析标准物质,及用于有机合成 ,制造树脂、染料和药品。

相关文献及参考

  • Metallation at the 2-position occurs readily with n-BuLi in ether (not readily in benzene). The 2,5-dilithio-derivative can be prepared in the presence of TMEDA: J. Chem. Soc., Perkin 1, 887 (1977), or with the superbasic combination of n-BuLi with KO-t-Bu: Synthesis, 316 (1988).
  • Merck:14,9353
  • Short: II/19b
  • Merck:14,9353 Beilstein:17(5)1,297

安全信息

GHS Symbol
WGK Germany3
Hazard Codes 3 F,T
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H331 Toxic if inhaled 吸入中毒
  • H302 Harmful if swallowed 吞食有害
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H318 Causes serious eye damage 严重伤害眼睛
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
  • H350 May cause cancer 可能致癌
  • H340 May cause genetic defects 可能导致遗传性缺陷
  • H373 May causes damage to organs through prolonged or repeated exposure 长期或频繁接触可能会损伤器官
Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
RTECSXM7350000
Precautionary statements
  • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
  • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P301+P312+P330
  • P302+P352+P332+P313+P362+P364
  • P303+P361+P353
  • P305+P351+P338
  • P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
  • P314 Get medical advice/attention if you feel unwell. 获取医疗咨询/就医,如果你觉得不舒服
  • P370+P378
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
UN Number 2414 UN2414
Risk Statements
  • R11 Highly flammable 非常易燃
  • R20/21/22 Harmful by inhalation, in contact with skin and if swallowed 吸入、皮肤接触和不慎吞咽有害
  • R20/22 Harmful by inhalation and if swallowed 吸入和不慎吞咽有害
  • R22 Harmful if swallowed 吞咽有害
  • R36 Irritating to eyes 刺激眼睛
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R37/38 Irritating to respiratory system and skin 对呼吸系统和皮肤有刺激性
  • R41 Risk of serious damage to eyes 有严重损伤眼睛的危险
  • R45 May cause cancer 可能致癌
  • R46 May cause inheritable genetic damage 可能引起遗传基因损害
  • R52/53
Safety Statements
  • S16 Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
  • S23 Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) 不要吸入气体/烟雾/蒸汽/喷雾;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S33 Take precautionary measures against static discharges 对静电采取预防措施;
  • S36 Wear suitable protective clothing 穿戴适当的防护服;
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S39 Wear eye/face protection 戴眼睛/面孔保护装置;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
  • S53 Avoid exposure - obtain special instructions before use 避免接触,使用前获得特别指示说明;
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置;
  • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免释放到环境中,参考特别指示/安全收据说明书;
  • S9 Keep container in a well-ventilated place 保持容器在通风良好的场所;
Packing GroupII
Hazard Class3
Storage condition 密封保存 Flammables area 储存温度2-8℃
Warnings 危化品目录(2015)
TYPE OF TEST            : LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 9500 mg/m3/2H
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   GTPZAB Gigiena Truda i Professional'nye Zabolevaniya.  Labor Hygiene and
   Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR)
   V.1-36, 1957-1992. For publisher information, see MTPEE

TYPE OF TEST            : LCLo - Lowest published lethal concentration
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 2000 ppm/6H
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   TOXID9 Toxicologist.  (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway,
   Akron, OH 44311) V.1-    1981-  Volume(issue)/page/year: 8,141,1988

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1400 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   GTPZAB Gigiena Truda i Professional'nye Zabolevaniya.  Labor Hygiene and
   Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR)
   V.1-36, 1957-1992. For publisher information, see MTPEEI
   Volume(issue)/page/year: 10(2),57,1966

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 100 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: AD277-689

Restrict 危险品

其他信息

  • 下游产品:NOCODAZOLE --> 2-噻吩甲胺 --> 4-(2-噻嗯基)丁酸 --> 5-(2-噻吩基)戊酸 --> 2-苯甲酰噻吩 --> (4-甲氧基-3-硝基苯基)-(2-噻吩)甲醛 --> 双(2-噻吩)酮 --> 2-(4-溴苯基)噻吩 --> 2-碘噻吩 --> 3-(2-噻吩甲基)丙酸 --> 2-(三氟乙酰基)噻吩 --> 2-(4-甲氧基苄氧基)噻吩 --> 2-噻吩磺酰氯 --> 2-(5-溴-2-噻酚)吡啶 --> 4-2-噻吩丁酸 --> 2-噻吩乙酸 --> 2-(正庚酰)噻吩 --> 2-(三甲基乙酰基)噻吩 --> 噻嘧啶
  • 粗苯精制产品:噻吩虽可用化学方法合成制取,但成本太高。噻吩存在于煤焦油和页岩油内。用浓硫酸洗涤煤焦油的粗苯馏分所得废酸作原料,在110~150℃水解,然后经分离提纯得到噻吩。噻吩主要存在于粗苯预精馏得到的轻苯中。当轻苯加氢精制时,噻吩遭到破坏,当轻苯酸洗精制时,大部分噻吩与不饱和化合物聚合成焦油状物质,仅有少量噻吩与硫酸作用生成便于提取的噻吩磺酸,这就大大地减少了噻吩的产量。 轻苯酸洗精制时,噻吩与硫酸反应生成噻吩磺酸溶解于废硫酸中,将废硫酸澄清,除去焦油状物质,然后进行水解蒸馏。馏出物经冷凝冷却和分离,可以得到含噻吩和苯族烃的粗馏油。粗馏油经碱中和至中性或微碱性后,用理论塔板数为30~40的精馏塔进行精馏,得到含噻吩大于90%的噻吩产品。精馏时切取的中间馏分集中后回流入粗馏油。当噻吩全部馏出后,残液还可以精馏出含间-二甲苯约95%的间-二甲苯产品。 这种从废硫酸中提取噻吩的方法,粗苯中噻吩的提取率低,且水解蒸馏设备需要使用耐腐蚀材料。为了提高噻吩的提取率,许多国家都在研究从粗苯中提取噻吩的新方法,其中比较成功的是萃取精馏提取噻吩法(ER法)。该法是向含噻吩的苯中加入适宜的萃取剂,以增大苯与噻吩之间的相对挥发度,以便精馏分离出噻吩。在许多萃取剂中,α-吡咯烷酮和N-甲基吡咯烷酮 (NMP)对噻吩的溶解能力强,虽然这种萃取剂只具有中等程度的选择性,但它的化
  • 图谱信息:噻吩(110-02-1)核磁图( 1 HNMR) 噻吩(110-02-1)质谱(MS) 噻吩(110-02-1)核磁图( 13 CNMR) 噻吩(110-02-1)红外图谱(IR1)
  • 用途一:用于合成药物先锋霉素等,也用于生产染料、合成树脂、溶剂等
  • Sigma Aldrich:110-02-1(sigmaaldrich)
  • 蒸气压:40 mm Hg ( 12.5 °C)
  • 用途四:噻吩(110-02-1)是一种重要的有机化工原料,它的用途非常广泛。主要用于染料、医药和树脂。合成新型广谱抗菌素先锋霉素,是一种重要的医药化工助剂,还可应用于彩色影片制造及特技摄影,合成一种复杂的试剂,用于铀等金属的提取分离等。
  • 杂环化合物:噻吩是含一个硫杂原子的五元杂环化合物,在煤焦油制得的粗苯中少量存在,具有类似苯芳香气味的无色液体,沸点为84℃,不溶于水,能与乙醇、乙醚、丙酮、苯、四氯化碳、庚烷、吡啶、1,4-二氧六环等混溶。易燃。耐热性强,加热至850℃而不分解。在强酸条件下不聚合,不分解,也不易被氧化。有中等程度毒性。噻吩环上的5个原子均为sp2杂化,处于同一平面,硫原子的一对未共用电子占据的p轨道与4个碳原子的p轨道平行且重叠,形成5原子6电子的闭合共轭体系,故具有芳香性,噻吩比苯容易发生亲电取代反应,取代主要发生在α-位 (2-位或5-位)。噻吩的重要衍生物是生物素,在室温下可以与浓硫酸发生磺化反应,生产溶于硫酸的2-噻吩磺酸,所以常用这种方法除去粗苯中的噻吩。 噻吩可用于生产各种染料、香料、耐急冷急热塑料、高活性溶剂、刺激素、杀虫剂、增亮剂、化妆品和生物活化物质以及维生素、麻醉剂和抗菌素等药品。也是制备广谱性驱虫药噻嘧啶、抗菌素类药物先锋霉素Ⅰ和Ⅱ的原料,还可进一步制备环丁砜等溶剂。采用化学法或电化学法可合成聚噻吩,经掺杂后,其电导率为2~10.6×103S/m,是一种有潜在应用前景的导电高分子材料。
  • Alfa Aesar:噻吩,99% Thiophene, 99%(110-02-1)
  • 上游原料:焦油 --> 粗苯 --> 固体氢氧化钠 --> 正丁烷 --> 甲基噻吩 --> 三硫化二磷
  • TCI Shanghai:噻吩 Thiophene,>;98.0%(GC)(

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