Malononitrile 丙二腈

CAS 109-77-3 MFCD00001883

化学结构图

109-77-3
SMILES: N#CCC#N

化学属性

Mol. FormulaC3H2N2
Mol. Weight66
Density1.049
Boiling Point220
Melting Point30-34
Refractive index1.4146
Flash Point112°(233°F)
Solubility溶于水、醇、苯,微溶于氯仿、乙酸。
TSCAYes
Stability对热、光、空气敏感

别名和识别编码

Chemical NameMalononitrile
Synonym CH2(CN)2 CYANOACETONITRILE Cyanoaceticnitrile Cyanoacetonitrile DICYANOMETHANE Dicyanmethan Dicyanomethane MALONODINITRILE MALONONITRILE METHYLENE CYANIDE METHYLENE DICYANIDE Malodinitril Malononitrile (form 1) Methane, dicyano- Methylene cyanide Propandinitril RCRA waste number U149 USAF KF-19 Usaf a-4600 cyanoacetonitrile fumaronitrile malonic dinitrile malonicdinitrile malononitrile propanedinitrile {} {} { 丙二腈 丙二酸二腈 二氰基甲 二氰基甲烷(丙二腈) 氰化次甲基 氰化次甲基,二氰代甲烷,氰基乙腈,缩苹果腈 氰基乙腈 缩苹果腈
CAS Number109-77-3
EC Number203-703-2
Beilstein Registry Number773697
MDL NumberMFCD00001883
PubChem Substance ID87572150
Reaxys-RN773697
Merck Number5711
Chemical Name Translation丙二腈
Wiswesser Line NotationNC1CN
LabNetwork Molecule IDLN00222908
InChIInChI=1S/C3H2N2/c4-2-1-3-5/h1H2
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分类

  • Building Blocks, C1 to C5, Chemical Synthesis, Cyanides/Nitriles, Nitrogen Compounds, Organic Building Blocks
  • {uni_hamburg} no charge; 1fragment
  • {SNA} Building Blocks, C1 to C5, Chemical Synthesis, Cyanides/Nitriles, Nitrogen Compounds, Organic Building Blocks
  • {Chemicalbook} 农药中间体: 除草剂中间体: 磺酰

产品应用

  • 有机合成原料。医药方面,用于合成维生素B1、氨蝶呤、氨苯蝶啶等一系列重要药物。染料方面、农药方面及其他方面都有重要的用途。也可用作金的萃取剂。中国现主要用于生产氨苯蝶啶、苄嘧黄隆、1,4,5,8-萘四甲酸、嘧啶系列产品。

相关文献及参考

  • Reviews of the chemistry of malononitrile: Chem. Rev., 69, 591 (1969); Synthesis, 165, 241 (1978); 925 (1981); Synlett, 2247 (2004).
  • Ternary condensation with an aromatic aldehyde and a cycloalkanone in the presence of ammonium acetate can give a variety of products. With cyclohexanone, the 2-amino-4-aryl-5,6,7,8-tetrahydroquinoline-3-carbonitriles are the major products: J. Chem. Res. (Synop.), 146 (1995).
  • Short: II/19b
  • Short: II/14a
  • Merck:14,5711 Beilstein:2,589
  • Merck:14,5711
  • The Na derivative can be arylated by reaction with aryl halides with a Pd catalyst: J. Chem. Soc., Chem. Commun., 932 (1984). In the presence of butadiene, an additional 4-carbon unit is introduced: J. Chem. Soc., Perkin 1, 647 (1990):

安全信息

GHS Symbol
WGK Germany3
Hazard statements
  • H300 Fatal if swallowed 吞食致命
  • H300+H330
  • H301 Toxic if swallowed 吞食有毒
  • H311 Toxic in contact with skin 皮肤接触中毒
  • H331 Toxic if inhaled 吸入中毒
  • H410 Verytoxictoaquaticlifewithlonglastingeffects 对水生生物毒性非常大并具有长期影响。
Personal Protective Equipment Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes 6.1 T,N
RTECSOO3150000
Precautionary statements
  • 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。
  • 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。
  • P284 Wear respiratory protection.? 佩戴呼吸保护装置。
  • P301+P310
  • P301+P310+P330
  • P302+P350
  • P302+P352+P312+P361+P364
  • P304+P340+P310
  • P305+P351+P338
  • P305+P351+P338+P310
  • P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
  • 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.....
Signal word Danger
Safety Statements
  • 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;
  • S27 Take off immediately all contaminated clothing 立即脱掉全部污染的衣服;
  • 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);
  • 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;
Risk Statements
  • R23/24/25 Toxic by inhalation, in contact with skin and if swallowed 吸入,皮肤接触及吞食都有毒
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R50/53
UN Number 2647 UN 2647 6.1/PG 2
Storage condition 0-10 0-10°C 2-8°C 储存温度2-8℃,充氩保存 密封保存。
Packing GroupII
Hazard Class6.1
Warnings 危化品目录(2015)
TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 13 mg/kg
TOXIC EFFECTS :
   Behavioral - general anesthetic
   Behavioral - convulsions or effect on seizure threshold
   Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
   NATUAS Nature.  (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736)
   V.1-    1869-  Volume(issue)/page/year: 228,1315,1970

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 32 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#07576

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 10043 ug/kg
TOXIC EFFECTS :
   Blood - other changes
REFERENCE :
   TOXID9 Toxicologist.  (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway,
   Akron, OH 44311) V.1-    1981-  Volume(issue)/page/year: 3,64,1983

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 20550 ug/kg
TOXIC EFFECTS :
   Behavioral - convulsions or effect on seizure threshold
   Behavioral - excitement
REFERENCE :
   MEPAAX Medycyna Pracy.  Industrial Medicine.  (Ars-Polona, POB 1001, 00-068
   Warsaw 1, Poland) V.1-    1950-  Volume(issue)/page/year: 27,1,1976

Restrict 危险品

其他信息

  • 图谱信息:丙二腈(109-77-3)质谱(MS) 丙二腈(109
  • 检测方法:GC
  • MOL 文件:109-77-3.mol
  • 职业标准:TWA 3 PPM
  • 用途二:丙二腈是制备2-氨基-4,6-二甲氧基嘧啶和2-氯-4,6-二甲氧基嘧啶的原料,可用以生产磺酰脲类除草剂如苄嘧磺隆、吡嘧磺隆等,又可用以制造除草剂双草醚,在医药上用以制造利尿药物。
  • 下游产品:5-氰基-4-氨基异噁唑 --> 4-氨基-5-氨基甲基嘧啶 --> 1,4,5,8-萘四甲酸 --> 2-氨基-4-氯-3-氰基-5-甲酰基噻吩 --> 4-氨基嘧啶-5-羧酰胺 --> 2-氨基-5,6-二氢-环戊烷并噻吩-3-羰酰胺 --> 5-氨基-1-(4-氯苯基)-4-氰基-1H-吡唑 --> 2,4,6-三氨基嘧啶 --> 四唑嘧磺隆 --> 4,6-二氨基-2-甲基巯基嘧啶 --> 2-氨基-3-氰基吡啶 --> 2-氨基-6-甲基-4,5,6,7-四氢-1-苯并噻吩-3-腈 --> 3,5-二氰基-3-氨基吡啶 --> 2,4-氨基嘧啶-5-羧酸 --> 2-氨基-5,6-二氢-4H-环戊烯并噻吩-3-甲腈 --> 2-氨基-3-腈基-4,5-二甲基噻吩 --> 4-氨基-6-甲基嘧啶-5-甲腈 --> 2-氨基-3-氰基-4-甲基-5-甲氧甲酰基噻吩 --> 2,4-二氨基嘧啶-5-腈 --> 2-氨基-3-腈基-4,5,6,7--四氢苯并[B]噻吩 --> 2-氨基烟酸 --> 左西孟旦 --> 4-氨基-1,2,5-噁二唑-3-甲腈 --> 3-环-4,5,6,7-四氧-6-甲基三丁酚 --> 5-氨基-1-苯基吡唑-4-腈 --> 4-甲基-2-氨基喹啉-3-腈 --> 分散艳蓝 S-FR --> 4,6-二甲基-2-羟基吡啶 --> 4,6-二氨基-2-巰基嘧啶 --> 3,5-二氟苯乙酸 --> 4-氨基嘧啶-5-甲腈 --> 4-氨基-2-(甲基硫代)嘧啶-5-腈 --> 2-氨基-6-氯-3,5-二氰基吡啶 --> 溶剂红 197 --> 2-氯-4,6-二甲氧基嘧啶
  • 类别:有毒物品
  • 毒性分级:剧毒
  • 方法二:1.实验室由氰乙酰胺与三氯氧磷进行消除反应制得。将1260g(15mol)氰乙酰胺、1kg食盐和5L二氯乙烷搅拌混合15min后,加入800ml(8.75mol)三氯氧磷。随后,加热回流8h。再冷至室温,过滤。用50ml二氯乙烷洗涤滤饼。合并滤、洗液,蒸出溶剂得粗品丙二腈。将粗品减压蒸馏,收率113-118℃(3.3kPa)馏分得产
  • 急性毒性:腹腔-大鼠 20.55 毫克/公斤;口服-小鼠 LD50:13 毫克/公斤
  • 方法二:1.实验室由氰乙酰胺与三氯氧磷进行消除反应制得。将1260g(15mol)氰乙酰胺、1kg食盐和5L二氯乙烷搅拌混合15min后,加入800ml(8.75mol)三氯氧磷。随后,加热回
  • 上游原料:三氯氧磷 --> 氯化钠 --> 氰乙酸乙酯 --> 二氯乙烷
  • Alfa Aesar:丙二腈,99% Malononitrile, 99%(109-77-3)
  • {C
  • 丙二腈价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 80076526 丙二腈;氰化亚甲基;二氰甲烷;氰基乙腈;缩苹果腈 100ml 131元 2011/04/16 M0033 丙二腈 Malononitrile 25G 160元 2011/04/16 M0033 丙二腈 Malononitrile 500G 1550元
  • 储运特性:库房通风低温干燥; 与氧化剂、酸类、食品添加剂分开存放
  • 用途一:用于制药,是药物氨苯蝶啶中间体
  • Acros Organics:马来
  • TCI Shanghai:丙二腈 Malononitrile,>;98.0%(GC)(T)(109-77-3)
  • 方法一:其制备方法是由氰乙酸乙酯与氨作用,在20℃以下反应,在冰浴中冷却2
  • Alfa Aesar:丙二腈,9

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