Dicyclopentadiene 二聚环戊二烯

CAS 77-73-6 MFCD00078246

化学结构图

77-73-6
SMILES: C1=CC2C3C=CC(C3)C2C1

化学属性

Mol. FormulaC10H12
Mol. Weight132
Density0.986
Boiling Point170
Melting Point33
Refractive indexn20/D 1.511
Flash Point44°C(lit.)
TSCAYes
Solubility不溶于水,溶于乙醇、乙醚。
Stability对热敏感

别名和识别编码

Chemical NameDicyclopentadiene
Synonym 1,3-cyclopentadiene dimer 3,4,7,7-Tetrahydro-4,7-methano-1H-indene 3A,4,7,7A-TETRAHYDRO-4,7-METHANO-1H-INDENE 3A,4,7,7A-TETRAHYDRO-4,7-METHANOINDENE 3a,4,7,7a-tetrahydro-4,7-methano-1H-indene 3a,4,7,7a-tetrahydro-4,7-methanoindene 3a,4,7,7a-tetrahydro-7-methanoindene 4,7-Methylen-4,7,8,9-tetrahydroinden 4,7-methano-1H-indene,3a,4,7,7a-tetrahydro- 4,7-亚甲基-3a,4,7,7a-四氢茚 4,7-亚甲基-4,7,8,9-四氢茚 Bicyclopentadiene Biscyclopentadiene CYCLOPENTADIENE DIMER Cyclopentadiene dimer DCPD DICYCLOPENTADIENE Tricyclo[5.2.1.02,6]deca-3,8-diene alpha-dicyclopentadiene(endoform) dicyclopentadiene 倍環戊二烯 联环戊二烯
CAS Number77-73-6
EC Number201-052-9
Beilstein Registry Number1904092
MDL NumberMFCD00078246
PubChem Substance ID6492
Merck Number14,2739
Reaxys-RN1904092
Chemical Name Translation二聚环戊二烯
InChIKeyHECLRDQVFMWTQS-UHFFFAOYSA-N
Wiswesser Line NotationL C555 A DU IUTJ
LabNetwork Molecule IDLN00198686
InChIInChI=1S/C10H12/c1-2-9-7-4-5-8(6-7)10(9)3-1/h1-2,4-5,7-10H,3,6H2
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分类

  • {SNA} Alkenes, Building Blocks, Chemical Synthesis, Cyclic, Materials Science, Monomers, Norbornene Monomers, Organic Building Blocks, Polymer Science, Vinyl Halides, Amines, Amides, and Other Vinyl Monomers
  • {SNA} Alphabetical Index of Analytical Standards, All alphabetically sorted, Analytical Standards, Analytical/Chromatography, Chromatography,
  • {SA} Alkenes, Building Blocks, Chemical Synthesis, Cyclic, Materials Science, Monomers, Organic Building Blocks, Polymer Science, Vinyl Halides, Amines, Amides, and Other Vinyl Monomers
  • {uni_hamburg} no charge; carbocycle; alicycle; large ring; fused rings; 5ring; 6ring; 8ring; 9ring; 1fragment
  • {SNA} Alkenes,
  • {SNA

产品应用

  • 环戊二烯二聚体(或环戊二烯)的主要用途有:(1)用作乙烯-丙烯二元共聚物(EPDM)的第三组份;(2)用作合成乙叉降冰片烯(ENB)的原料;(3)与顺丁烯二酸酐反应得到降冰片烯二酸酐,用作环氧树脂固化剂、聚酯树脂、醇酸树脂、杀虫剂的原料;(4)环戊二烯的六氯化物——六氯环戊二烯,与顺酐反应得到的六氯化内亚甲基的氢化邻苯二甲酸酐,用作合成树脂的阻燃剂;(5)二聚环戊二烯用于桐油、亚麻仁油、大豆油、鱼油等的改性,可加快干燥性,提高耐水、耐碱性;(6)二聚环戊二烯树脂可用作橡胶粘合剂、压敏粘接剂、热溶粘合剂、油墨、涂料等;(7)二聚环戊二烯氧化物可用作注射成型和层压成型树脂;(8)环戊二烯部分加氢得到的环戊烯,再聚合制得1,5-反式聚环戊烯;(9)环戊二烯是生产艾氏剂、荻氏剂类杀虫剂原料;(10)环戊二烯还用于药物合成。例如胃长乐的中间体α-环戊二烯基扁桃酸甲酯,由苯乙酮酸甲酯与环戊二烯加成而得;(11)加氢后用作高能燃料。

相关文献及参考

  • Beilstein: 5,II,391
  • Short: III/38A
  • The cyclopentadienyl anion reacts with carbonyl compounds with the formation of fulvenes. For example using KOH and 18-crown-6, see: Synthesis, 799 (1980).
  • Source, on heating, of monomeric cyclopentadiene. For details, see: Org. Synth. Coll., 7, 339 (1990).
  • Short: III/38B
  • Diels-Alder reaction with 1,4-benzoquinones and subsequent retro Diels-Alder with elimination of cyclopentadiene have been used in synthesis of 2-cyclohexene-1,4-diones: J. Chem. Soc. (C), 124 (1969); Org. Synth. Coll., 9, 186 (1998). For an enantioselective, catalytic Diels-Alder reaction, see: Org. Synth. Coll., 9, 67 (1998).
  • Readily deprotonated by strong bases to give the 6πAlpha/Delectron cyclopentadienyl anion, which forms stable complexes with many transition metals. Conversion to ferrocene by two alternative procedures: Org. Synth. Coll., 4, 473 (1963), or using crown-ether catalysis: Angew. Chem. Int. Ed., 18, 792 (1979). Preparation of ruthenocene: Org. Synth. Coll., 5, 1001 (1973).
  • For a review of methods for the synthesis of a wide variety of 1,3-bifunctionalized cyclopentanes and cyclopentenes from cyclopentadiene, see: Angew. Chem. Int. Ed., 21, 480 (1982).
  • Short: IV/18B

安全信息

Signal word Danger
GHS Symbol
WGK Germany2
Safety Statements
  • 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;
  • 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;
  • 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);
  • 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;
Risk Statements
  • R10 Flammable 易燃
  • R11 Highly flammable 非常易燃
  • 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
  • R23 Toxic by inhalation 吸入有毒
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R51/53
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前,切勿操作。
  • 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。
  • P233 Keep container tightly closed. ?保持容器密闭。
  • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
  • P241 Use explosion-proof electrical/ventilating/lighting/…/equipment. 使用防爆电气/通风/照明/ .../设备。
  • P242 Use only non-sparking tools. 只能使用无火花工具。
  • P243 Take precautionary measures against static discharge. 采取预防措施,防止静电放电。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • 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。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P273 Avoid release to the environment. 避免释放到环境中。
  • 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。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P284 Wear respiratory protection.? 佩戴呼吸保护装置。
  • P301+P310
  • P301+P310+P331+P330
  • P301+P312
  • P302+P350
  • P302+P352
  • P302+P352+P332+P313+P362+P364
  • P303+P361+P353
  • P304+P312
  • P304+P340
  • P304+P340+P310
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P307+P311
  • P308+P311
  • P308+P313
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
  • P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适,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
  • P320 Specific treatment is urgent (see … on this label). 紧急具体治疗(见本标签上的)。
  • P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
  • P330 Rinse mouth. 漱口
  • P331 Do NOT induce vomiting.. 不要催吐。
  • P332+P313
  • P337+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
  • P370+P378
  • P391 Collect spillage. Hazardous to the aquatic environment 收集对水环境有危害的泄漏物。
  • P403+P233
  • P403+P235
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
  • H226 Flammable liquid and vapour 易燃液体和蒸气
  • H228 Flammable solid 易燃固体
  • H302 Harmful if swallowed 吞食有害
  • H304 May be fatal if swallowed and enters airways 吞食和进入呼吸道可能致命
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H330 Fatal if inhaled 吸入致命
  • H331 Toxic if inhaled 吸入中毒
  • H332 Harmful if inhaled 吸入有害
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害
  • H400 Verytoxictoaquaticlife 对水生生物毒性非常大。
  • H411 Toxictoaquaticlifewithlonglastingeffects 对水生生物有毒性并具有长期影响。
Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
RTECSPC1050000
Packing GroupIII
UN Number 2048
Hazard Codes 3 T,N
Hazard Class3
Storage condition Flammables area
Warnings 危化品目录(2015)
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Bird - domestic
DOSE/DURATION           : 1010 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: AD-A087-257

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 190 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   40QBA3 "Proceedings of the International Congress on Toxicology, Toxicology
   as a Predictive Science, 1st, Toronto, 1977," Plaa, G.L., and W.A. Duncan,
   eds., New York, Academic Press, Inc., 1978  Volume(issue)/page/year:
   -,448,1978

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 200 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NCIUS* Progress Report for Contract No. PH-43-64-886, Submitted to the
   National Cancer Institute by The Institute of Chemical Biology, University
   of San Francisco.  (San Francisco, CA 94117)  Volume(issue)/page/year:
   PH43-64-886

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 200 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NCIUS* Progress Report for Contract No.

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       :

Restrict 剧毒

其他信息

  • 上游原料:茂 --> 焦油 --> 轻苯
  • Acros Organic
  • 用途三:环戊二烯二聚体(或环戊二烯)的主要用途有:(1)用作乙烯-丙烯二元共聚物(EPDM)的第三组份;(2)用作合成乙叉降冰片烯(ENB)的原料;(3)与顺丁烯二酸酐反应得到降冰片烯二酸酐,用作环氧树脂固化剂、聚酯树脂、醇酸树脂、杀虫剂的原料;(4)环戊二烯的六氯化物――六氯环戊
  • Acros Organics:二环戊二烯 Dicyclopentadiene, stabilized, 95%(
  • 储运特性:库房通风低温干燥; 与氧化剂分开存放; 不宜久储, 以防聚合
  • 下游产品:茂 --> 环戊烯 --> 1,1'-双(二苯基膦)二茂铁 --> 3-环戊烯-1-醇 --> 盐酸金刚烷胺 --> 甲基纳
  • TCI Shanghai
  • 下游产品:茂 --> 环戊烯 --> 1,1'-双(二苯基膦)二茂铁 -
  • Sigma
  • MOL 文件:77-73-6.mol
  • 用途二:环戊二烯二聚体(或环戊二烯)的主要用途有:(1)用作乙烯-丙烯二元共聚物(EPDM)的第三组份;(2)用作合成乙叉降冰片烯(ENB)的原料;(3)与顺丁烯二酸酐反应得到降冰片烯二酸酐,用作环氧树脂固化剂、聚酯树脂、醇酸树脂、杀虫剂的原料;(4)环戊二烯的六氯化物——六氯环戊二烯,与顺酐反应得到的六氯化内亚甲基的氢化邻苯二甲酸酐,用作合成树脂的阻燃剂;(5)二聚环戊二烯用于桐油、亚麻仁油、大豆油、鱼油等的改性,可加快干燥性,提高耐水、耐碱性;(6)二聚环戊二烯树脂可用作橡胶粘合剂、压敏粘接剂、热溶粘合剂、油墨、涂料等;(7)二聚环戊二烯氧化物可用作注射成型和层压成型树脂;(8)环戊二烯部分加氢得到的环戊烯,再聚合制得1,5-反式聚环戊烯;(9)环戊二烯是生产艾氏剂、荻氏剂类杀虫剂原料;(10)环戊二烯还用于药物合成。例如胃长乐的中间体α-环戊二烯基扁桃酸甲酯,由
  • 用途一:用于制造金属有机化合物、二茂铁、杀虫剂、味精和石油树脂等
  • Alfa Aesar:二聚环戊二烯,一般为95%,BHT作稳定剂 Dicyclopentadiene, typic
  • 用途三:环戊二烯二聚体(或环戊
  • 凝固点:31.5℃
  • 方法一:将煤焦油的轻苯馏分蒸馏,切取<70
  • 灭火剂:干粉、干砂、二氧化碳、泡沫、1211灭火剂
  • 爆炸物危险特性:与空气混合可爆
  • 二聚环戊二烯价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 TD044301 环戊二烯二聚体 500ml 260元 2011/04/16 D0443 二聚环戊二烯(含稳定剂BHT)[环戊二烯的前驱体] Dicyclopentadiene (stabilized with BHT) [precursor to Cyclopentadiene] 500ML 265元 2011/04/16 D0443 二聚环戊二烯(含稳定剂BHT)[环戊二烯的前驱体] Dicyclopentadiene (stabilized with BHT) [precursor to Cyclopentadiene] 25ML 150元
  • {Ch
  • 图谱信息:
  • 外观性质:无色晶体。
  • 有类似樟脑气味。溶于醇、醚和四氯化碳,不溶于水。本品有α和β两种异构体,α异构体凝固点33℃,β异构体凝固点19.5℃。双环戊二烯中主要含的是α异构体。本品因含有双键,故易于进行加成反应和自聚反应。
  • 防护措施:本品有毒,具有麻痹性及局部刺激作用,急性中毒能引起昏迷。大鼠经口LD50为820mg/kg体重,兔经皮肤吸收L
  • 类别:易燃液体
  • Acros Organics:二环戊二烯 Dicyclopentadiene, stabilized, 95%(77-73-6)
  • 海关编码:29021990

系列性分类