Phenanthrene 菲

CAS 85-01-8 MFCD00001168

化学结构图

85-01-8
SMILES: C1CCC2C(C1)CCC1CCCCC12

化学属性

Mol. FormulaC14H10
Mol. Weight178.23
Density1.063
Boiling Point337.4°C at 760 mmHg
Melting Point98-100°C
Flash Point171°(339°F)
TSCAYes
SolubilitySoluble in alcohol, benzene, toluene, and glacial acetic acid
Appearance platelets (fine)
Refractive index1.5943
Stability对光敏感

别名和识别编码

Chemical NamePhenanthrene
Synonym Phenanthrene {LY} Phenanthrene {} {LY} Phenanthrene {} {} {LY} Phenanthrene {} {} {} {LY} Phenanthrene {} {} {} {} {LY} Phenanthrene {} {} {} {} {} {LY} Phenanthrene {} {} {} {} {} {} {LY} Phenanthrene {} {} {} {} {} {} {} {LY} Phenanthrene {} {} {} {} {} {} {} {} {LY} Phenanthrene {} {} {} {} {} {} {} {} {} {LY} Phenanthrene {} {} {} {} {} {} {} {} {} {} {LY} Phenanthrene {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {LY} Phenanthrene {} {} {} {} {} {} {} {} {} {} {} {} {LY} Phenanthrene {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Phenanthrene {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Phenanthrene {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Phenanthrene {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Phenanthrene {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Phenanthrene
CAS Number85-01-8
EC Number201-581-5
Beilstein Registry Number1905428
MDL NumberMFCD00001168
PubChem Substance ID995
Merck Number7212
Reaxys-RN1905428
Chemical Name Translation
Wiswesser Line NotationL B666J
LabNetwork Molecule IDLN00196250
Canonical SMILESC12=CC=CC=C1C=CC3=CC=CC=C23
InChIInChI=1S/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H
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分类

  • {SNA} Charge Transport and Photosensitizing Materials, Light-Emitting Dopants and Fluorescent Dyes, Materials Science, OLED and PLED Materials, Organic and Printed Electronics, Photoluminescent Materials, Photonic and Optical Materials, Sublimed Materials
  • {SNA} Bioactive Small Molecu
  • {SNA} All PAH Standards, Analytical Standards, Analytical/Chromatography, CRMs, Certified Reference Mate
  • {SNA} Arenes, Building Blocks, Chemical Synthesis, Organic Building Blocks
  • {SNA} Bioactive Small Molecules, Light-Emitting Dopants and Fluorescent Dyes, Materials Science, Organic and Printed Electronics, P, Photoluminescent Materials, Photonic and Optical Materials, 细胞生

产品应用

  • 可用于合成树脂、植物生长激素、还原染料、鞣料等方面, 菲经氢化制得全氢菲可用于生产喷气飞机的燃料。

相关文献及参考

  • Short: II/27C
  • Short: II/27B
  • Ozonolysis, followed by work-up with OH-, leads to the aldehydo-acid: Org. Synth. Coll., 5, 493 (1973). The dialdehyde can be obtained by reduction of the ozonide with NaI: Org. Synth. Coll., 5, 489 (1973).
  • Has been used as a hydrogen-acceptor in the direct metallation of imines and alkynes by Li metal, as an alternative to the use of LDA: Synthesis, 947 (1984).
  • Merck: 14,7212
  • Merck: 14,7212 Beilstein: 5,IV,2297

安全信息

Signal word Danger Warning
GHS Symbol
WGK Germany2
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;
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
  • S25 Avoid contact with eyes 避免眼睛接触;
  • 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;
  • S29 Do not empty into drains 不要排入下水道;
  • 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;
  • 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;
  • S57 Use appropriate containment to avoid environmental contamination 使用适当容器避免环境污染;
  • 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;
  • S62 If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label where possible 吞食后不要催吐:立即求医并出示该容器或标签;
  • S7 Keep container tightly closed 保存在严格密闭容器中;
  • S9 Keep container in a well-ventilated place 保持容器在通风良好的场所;
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
  • R50 Very toxic to aquatic organisms 对水生生物极毒
  • R50/53
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。
  • 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。
  • P272 Contaminated work clothing should not be allowed out of the workplace. 污染的工作服不得带出工作场所。
  • 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。
  • P301+P310
  • P301+P312
  • P301+P312+P330
  • P301+P317
  • P302+P352
  • P302+P352+P333+P313+P362+P364
  • P304+P340
  • P305+P351+P338
  • 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。
  • 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
  • P333+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
  • P362+P364
  • P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
  • P391 Collect spillage. Hazardous to the aquatic environment 收集对水环境有危害的泄漏物。
  • P403+P233
  • 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
  • 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
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H336 May cause drowsiness or dizziness 肯能导致嗜睡或头晕
  • H400 Verytoxictoaquaticlife 对水生生物毒性非常大。
  • H410 Verytoxictoaquaticlifewithlonglastingeffects 对水生生物毒性非常大并具有长期影响。
Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter dust mask type N95 (US), Eyeshields, Gloves
RTECSSF7175000
Packing GroupIII
UN Number 3077 UN 3077 9/PG 3 UN3077
Hazard Codes 9
Storage condition Store at room temperature {LY} Store at room temperature Under Inert Atmosphere {} {LY} Store at room temperature {} {} {LY} Store at room temperature {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {}
Hazard Class9
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 71 mg/kg
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Skin and Appendages - tumors
   Tumorigenic - tumors at site of application
REFERENCE :
   JNCIAM Journal of the National Cancer Institute.  (Washington, DC)  V.1-60,
   1940-78.  For publisher information, see JJIND8.  Volume(issue)/page/year:
   50,1717,1973

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 22 gm/kg/10W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Skin and Appendages - tumors
REFERENCE :
   BJCAAI British Journal of Cancer.  (Macmillan Press Ltd., Houndmills,
   Basingstoke, Hants. RG21 2XS, UK)  V.1-    1947-  Volume(issue)/page/year:
   10,363,1956

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 56 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems
   Laboratory, NIOSH Exchange Chemicals.  (Aberdeen Proving Ground, MD 21010)
   Volume(issue)/page/year: NX#00190

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 700 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JJIND8 JNCI, Journal of the National Cancer Institute.  (Washington, DC)
   V.61-79, 1978-87. For publisher information, see JNCIEQ.
   Volume(issue)/page/year: 62,911,1979

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 700 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   HYSAAV Hygiene and Sanitation (USSR).  English translation of GISAAA.
   (Springfield, VA)  1964-71. Discontinued.  Volume(issue)/page/year:
   29(6),19,1964

TYPE OF TEST            : Phage inhibition capacity
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 25 ug/well
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 260,349,1991

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Rodent - rat Liver
DOSE/DURATION           : 3 mmol/L
REFERENCE :
   SinJF# Personal Communication from J.F. Sina, Merck Institute for
   Therapeutic Research, West Point, PA 19486, Oct. 26, 1982
   Volume(issue)/page/year: 26OCT1982

TYPE OF TEST            : Specific locus test

TYPE OF TEST            : Morphological transformation
TEST SYSTEM             : Rodent - rat Embryo
DOSE/DURATION           : 10 mg/L
REFERENCE :
   JNCIAM Journal of the National Cancer Institute.  (Washington, DC)  V.1-60,
   1940-78.  For publisher information, see JJIND8.  Volume(issue)/page/year:
   51,799,1973

TYPE OF TEST            : DNA adduct
TEST SYSTEM             : Fish - salmon Testis
DOSE/DURATION           : 5 ug/1H (Continuous)
REFERENCE :
   BIJOAK Biochemical Journal.  (Biochemical Soc. Book Depot, POB 32, Commerce
   Way, Colchester, Essex CO2 8HP, UK)

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Rodent - hamster Fibroblast
DOSE/DURATION           : 5 mg/L/24H
REFERENCE :
   BCPCA6 Biochemical Pharmacology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.1-    1958-  Volume(issue)/page/year:
   20,1297,1971

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Rodent - hamster Lung
DOSE/DURATION           : 40 mg/L/27H
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 66,277,1979

TYPE OF TEST

其他信息

  • 多环芳烃(PAHs)单组分标准液
  • 图谱信息:菲(85-01-8)核磁图( 13 CNMR) 菲(85-01-8)
  • 菲价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 K7747001 菲 25g 743元 2011/08/23 xp400108 菲 1g 168元 2011/04/16 P1310 菲 Phenanthrene 25G 216元
  • MOL 文件:85-01-8.mol
  • Alfa Aesar:菲,98% Phenan
  • 图谱信息:菲(85-01-8)核磁图( 13
  • Acros Organics:菲 Phenanthrene, 97%(85-01-8)
  • 检测方法:H
  • 能升华。不溶于水,稍溶于乙醇,能溶于乙醚、冰醋酸、苯、四氯化碳和二硫化碳等。溶液具有蓝色荧光。
  • F:8
  • color:brown
  • 分子结构:菲的分子结构与蒽相似,分子中所有原子在同一平面上,但不在同一直线上,是一个闭合的共轭体系,具有芳香性。分子中1,2,3,4,10位和5,6,7,8,9位相对应,但5个位置活性有差别,其中9与10位活性较高,取代、氧化、加成反应首先在9与10位进行: 菲醌是一种农药,用做杀菌拌种剂,可以防止小麦赤霉病、坚黑穗病和红薯黑斑病。 工业上菲是从蒸馏煤焦油所得的蒽油馏分中提取。很多天然产物 (如甾醇) 分子中含有这个环系。菲主要用于制造染料、药物、高效低毒农药,并可用做闪烁剂、无烟火药的稳定剂等。许多菲的衍生物具有致癌的生理作用。如: 2-甲基-3,4-苯并菲和1,2,3,4-二苯并菲的分子结构式
  • 用途四:可用于合成树脂、植物生长激素、还原染料、鞣料等方面, 菲经氢化制得全氢菲可用于生产喷气飞机的燃料。
  • 用途一:用于分子量的测定及有机化合物的合成
  • 非直线式稠环芳烃:菲是最简单的非直线式稠环芳烃,具有三个苯环结构,为蒽的同分异构体。1872年E.Ostermayer等在煤焦油的蒽油馏分中发现了菲,是煤焦油加工产品之一。在高温煤焦油中菲的含量仅次于萘,约为4~6%,主要集中在一蒽油馏分中。菲的化学活性强于萘,但比蒽弱,9,10位也可发生氧化、加成等反应。菲是带光泽的无色晶体,从乙醇中析出的菲为无色单斜晶系片状结晶,升华得到的菲为叶片状结晶,相对密度1.179(25/4℃),折射率为1.6450,熔点101℃,沸点340℃,能升华,不溶于水,微溶于乙醇,溶于乙醚、苯、冰醋酸、三氯甲烷、四氯化碳和二硫化碳,溶液发蓝色荧光。分子中1, 4,5,8-位相同称为α-位;2,3,6,7-位相同称为β-位;9,10-位相同称为γ-位。化学性质介于萘和蒽之间。它也可以在 9,10-位起加成反应,但没有蒽那样容易。氧化也发生在9,10-位,氧化得菲醌。也可发生取代反应。可由煤焦油的蒽油馏分中分离而得菲。菲可用于制造农药和染料等,也用作高效低毒农药及无烟火药等炸药的稳定剂。 菲转化加工后可用于生产染料、药物和树脂等。菲的氧化产物菲醌可用作染料、杀菌剂和聚合抑制剂等;9,10-联苯二甲酸则用于制取聚酯和醇酸树脂;9,10-二氢-9-菲甲酸是一种植物生长刺激素;菲经氢化制得的全氢菲,可用于生产喷气机燃料;磺化所得菲磺酸,可用作粘结剂和鞣料。在用溶剂法制取精蒽时得到的含菲洗涤母液,经回收
  • 用途三:菲经氧化制得菲醌,用来代替有机汞剂农药西力生、赛力散,经氧化得到的联苯酸可用于制取醇酸树脂,菲氧化还可得到苯酐、环己酮、苯酚。菲氯化产品可用来制造不易燃的电气绝缘体和浸渍剂。菲磺化得到的菲磺酸可制粘结剂、鞣料等。但实际上这些应用领域大部分还有待发展。在造纸工业上,菲可作纸浆防雾剂;还可用于硝化甘油炸药和硝化纤维稳定剂及制造烟幕弹;菲的固体氧化物可制耐焰性好的电气绝缘材料和填充剂。在医药上,菲可合成生物碱——吗啡和咖啡因、二甲基吗啡和许多生殖器官具有特殊生理作用的医药。在染料工业上,菲可制取2-氨基菲醌,苯绕蒽酮,硫化还原染料(蓝BO,黑BB及棕色)等。此外,塑料工业上合成鞣剂以及菲在高温高压下加氢可得过氢菲,是高级喷气式飞机的燃料。
  • 上游原料:焦油 --> 焦油 --> 蒽 --> 咔唑 --> 重苯 --> 一蒽油

系列性分类


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