2,4-Pentanedione 乙酰丙酮

CAS 123-54-6 MFCD00008787

化学结构图

123-54-6
SMILES: CC(=O)CC(C)=O

化学属性

Mol. FormulaC5H8O2
Mol. Weight100
Refractive index1.4500 to 1.4540
Boiling Point133-135
Density0.975
Melting Point-23
Flash Point34°C(lit.)
TSCAYes
Autoignition Point662 °F
Vapor Density3.5 (vs air)
Vapor Pressure6 mmHg ( 20 °C)
SolubilitySoluble in water (160 g/L) at 20 °C, ether, acetone, glacial acetic acid, and miscible in benzene,ethanol, diethyl ether, chloroform, toluene and carbon disulfide, Insoluble in Glycerin.
Stability对光敏感

别名和识别编码

Chemical Name2,4-Pentanedione
Synonym 2,4-戊二酮 ACETYLPROPIONYL 乙基丙酮 METHYL ETHYL DIKETONE 乙酰丙酮,戊间二酮 2,4-Dioxopentane Pentanedione-2,4 DIACETYLMETHANE 2,4-Diketopentane 2,4-PENTADIONE 4-戊二酮 二乙酰基甲烷 pentane-2,4-dione 二乙酰基甲烷;2,4-戊二酮 2,4-PENTANEDIONE Acetone, acetyl- 2,4-戊烷二酮 ACAC 2,4-Pentadione 2-Propanone, acetyl- 乙酰丙酮 2,4-Pentandione 乙酰丙铜 乙醯丙酮 2,4-戊二酮 AcAc AcAc
CAS Number123-54-6
PubChem Substance ID87574324
EC Number204-634-0
Beilstein Registry Number741937
MDL NumberMFCD00008787
Reaxys-RN741937
Merck Number81
Chemical Name Translation乙酰丙酮
Wiswesser Line Notation1V1V1
LabNetwork Molecule IDLN00195358
InChIInChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3
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分类

  • A-AM, A-B, Puriss p.a., Amber Glass Bottles, Analytical Reagents, Analytical Reagents for General Use, Analytical/Chromatography, Bioactive Small Molecules, Cell Biology, Puriss p.a., Solvent Bottles, Solvent Packaging Options, Solvents
  • {SNA} A-AM,

产品应用

  • An indicator for the complexometric titration of Fe(III)

相关文献及参考

  • 3. H.F. Gilbert, M.H. O'Leary Biochim. Biophys. Acta 483 , 79, (1977) 摘要
  • Merck: 14,81
  • 4. H. Blakeotwell et al. Biochim. Biophys. Acta 568 , 297, (1979) 摘要
  • A simple procedure for the synthesis of methyl ketones involves alkylation at the 3-position with an alkyl halide using K2CO3 in EtOH, with in situ acetyl cleavage: Org. Synth. Coll., 5, 767 (1973). Knoevenagel condensation with aldehydes in THF in the presence of K2CO3 also occurs with acetyl cleavage, providing a simple route to alkenyl ketones: Chem. Lett., 1325 (1978). With K2CO3 and TBAB, selective one-pot monoalkylation or dialkylation with different alkyl groups can be achieved: Synthesis, 688 (1989). 3-Arylation with aryl bromides takes place in the presence of Cu(I) or Cu(II) salts in DMF: Chem. Lett., 597 (1982); Org. Synth. Coll., 6, 36 (1988).
  • Strong bases, e.g. NaNH2, form the dianion which reacts with electrophiles, e.g. alkyl halides, esters, acyl halides, Michael acceptors, etc., at the less-stabilized terminal carbon: J. Org. Chem., 26, 1716 (1961); Tetrahedron Lett., 357 (1970); J. Org. Chem., 39, 2289 (1974); Org. Synth. Coll., 5, 848 (1973). For arylation at the 1-position, see Diphenyl­iodonium chloride, A15149. For reviews of dimetallation, see: Org. React., 17, 155 (1969); Synthesis, 509 (1977).
  • {uni
  • Merck: 14,81 Beilstein:1,777
  • Merck 14 ,81

安全信息

GHS Symbol
WGK Germany1
Hazard Codes
Hazard statements
  • H226 Flammable liquid and vapour 易燃液体和蒸气
  • H331 Toxic if inhaled 吸入中毒
  • H302 Harmful if swallowed 吞食有害
  • H311 Toxic in contact with skin 皮肤接触中毒
Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
RTECSSA1925000
Precautionary statements
  • 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。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P307+P311
  • P304+P340+P312
  • 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。
  • 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。
  • P302+P352+P312
  • P403+P233
  • P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
  • P301+P312+P330
  • P241+P242+P243
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P303+P361+P353
  • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
  • P370+P378
  • P301+P312
  • 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。
  • P241 Use explosion-proof electrical/ventilating/lighting/…/equipment. 使用防爆电气/通风/照明/ .../设备。
  • 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。
  • P304+P340+P311
  • P273 Avoid release to the environment. 避免释放到环境中。
  • P308+P311
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;
  • S21 When using do not smoke 使用时,禁止吸烟;
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
  • 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;
  • 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;
Risk Statements
  • R10 Flammable 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
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R22 Harmful if swallowed 吞咽有害
  • R11 Highly flammable 非常易燃
UN Number
Packing GroupIII
Hazard Class3/6.1
Storage condition 密封阴凉避光保存。 2-8°C
Warnings 危化品目录(2015)
TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - guinea pig
DOSE/DURATION           : 20 mL/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: OTS0533573

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 810 uL/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   DCTODJ Drug and Chemical Toxicology.  (Marcel Dekker, 270 Madison Ave., New
   York, NY 10016) V.1-    1977/78-  Volume(issue)/page/year: 9,133,1986

TYPE OF TEST            : LD50 - Le

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 55 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - rigidity (including catalepsy)
REFERENCE :
   GISAAA Gigiena i Sanitariya.  For English translation, see HYSAAV.  (V/O
   Mezhdunarodnaya Kniga, 113095 Moscow, USSR)  V.1-    1936-
   Volume(issue)/page/year: 52(10),88,19

TYPE OF TEST            : LCLo - Lowest published lethal concentration
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1000 ppm/4H
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JIHTAB Journal of Industrial Hygiene and Toxicology.  (Cambridge, MA)
   V.18-31, 1936-49.  For publisher information, see AEHLAU.
   Volume(issue)/page/year: 31,343,1949

TYPE OF TEST            : Dominant lethal test
ROUTE OF EXPOSURE       : Inhalation
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 694 ppm/6h/5D
REFERENCE :
   TIHEEC Toxicology and Industrial Health.  (Princeton Scientific Pub. Co.,
   POB 2155, Princeton, NJ 08540)  V.1-    1985-  Volume(issue)/page/year:
   5,463,1989

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 80 mg/L
REFERENCE :
   EPASR* United States Environmental Protection Agency, Office of Pesticides
   and Toxic Substances. (U.S. Environmental Protection Agency, 401 M St., SW,
   Washington, DC 20460)  History unknown.  Volume(issue)/page/year:
   8EHQ-0386-0595

TYPE OF TEST            : TCLo - Lowest published toxic concentration
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 398 ppm/6H
SEX/DURATION            : female 6-15 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
REFERENCE :
   TIHEEC Toxicology and Industrial Health.  (Princeton Scientific Pub. Co.,
   POB 2155, Princeton, NJ 08540)  V.1-    1985-  Volume(issue)/page/year:
   6,461,1990

Restrict 危险品

其他信息

  • 用途二:用作分析试剂及钨、钼中铝的萃取剂
  • 有机合成中间体:乙酰丙酮是一种重要有机合成中间体,广泛用于制药、香料、农药等工业。 乙酰丙酮是制药工业的重要原料,如合成4,6-二甲基嘧啶衍生物等。还用作醋酸纤维素的溶剂,油漆和清漆等的干燥剂,也是重要的分析试剂。
  • 下游产品:1,7-双(4-羟基-3-甲氧基苯基)庚烷-3,5-二酮 --> 2-羟基-4-甲氧甲基-6-甲基
  • 方法一:其制备方法是由乙酸裂解生成的乙酰
  • 有机合成中间体:乙酰丙酮是一种重要有机合成中间体,广泛用于制药、香料、农药等工业。 乙酰丙酮是制药工业的重要原料,如合成4,6-二甲基嘧啶衍生物等。还用作醋酸纤维素的溶剂,油漆和清漆等的干燥剂,也是重要的分析试剂。 由于烯醇式的存在,乙酰丙酮能与金属钴(Ⅱ)、钴(Ⅲ)、铍、铝、铬、铁(Ⅱ)、铜、镍、钯、锌、铟、锡、锆、镁、锰、钪和钍等多种金属离子生成螯合物,可用作燃料油的添加剂和润滑油的添加剂。 利用其与金属的螯合作用,可用作
  • 用途一:用作制药的原料及有机中间体,也可作溶剂
  • 方法二:可采用不同的工艺路线:丙酮与乙烯酮反应或乙酐与丙酮缩合或丙酮与乙酸乙酯缩合。丙酮与乙烯酮的反应的过程,实际上是以丙酮为原料,经乙烯酮、乙酸异丙烯酯,再经转化而得乙酰丙酮;工艺过程如下:将含有1/1000二硫化碳的丙酮气化后引入780-800℃的裂化炉,使之生成乙烯酮(或冰醋酸经气化磷酸三乙酯催化剂存在下,以氨为稳定剂,经700℃裂化炉裂解为乙烯酮),乙烯酮用丙酮吸收,在硫酸或乙酰磺酰存在下,于61-71℃使之与乙酸反应生成乙酸异丙烯酯,经分馏提纯后,乙酸异丙稀酯纯度可达93-95%以上。再将乙酸异丙烯酯气化,引入预热至560-570℃转化炉,经分子重排生成乙酰丙酮,经冷凝,分馏提纯得成品。每吨产品消耗丙酮约2700kg。丙酮与乙酸乙酯缩合的过程是在金属钠存在下进行的。操作示例1在冷却的烧杯中加入120ml精制的乙酸乙酯和32ml氨气。在氨基钠加完后,在冰水中不停振摇24h后,在室温下放置过夜。次日加入100g冰,继而加入同量的冰水,取其水层,加入稀硫酸使呈酸性。在此溶液中加入饱和乙酸铜溶液(将40g粉末状乙酸铜加一定量的热水溶解而成),使乙酰丙酮形成铜盐析出。如反应液为碱性,可加入少量乙酸。过2-3h后,将青灰色乙酰丙酮抽滤,用水洗涤两次,直接移入分液漏斗中,加乙醚不断振摇,同时加入50ml4N硫酸使其分解。取乙醚溶液,再用乙醚萃取酸层中的乙酰丙酮,合并两次乙醚溶液,用
  • 有愉快的气味。受光作用会变棕色成树脂状物。能与乙醇、苯、氯仿、乙醚、丙酮、冰乙酸混溶,1份约溶于8份水中。与许多金属生成能溶于有机溶剂和和有挥发性的盐。易燃。低毒,半数致死量(大鼠,经口)1000mg/kg。
  • 急性毒性:口服- 大鼠 LD50: 55 毫克/ 公斤; 口服- 小鼠 LD50: 951 毫克/ 公斤
  • 用途五:有机合成,色层分析用试剂,过渡金属螯合剂。比色法测定铁和氟,在二硫化碳存在时测定铊。
  • 用途三:戊二酮又称乙酰丙酮,是杀菌剂甲基嘧菌胺、嘧菌胺和除草剂嘧磺隆的中间体。
  • F:9-23
  • Alfa Aesar:2,4-戊烷二酮,99% 2,4-Pentanedione, 99%(123-54-6)
  • 下游产品:1,7-双(4-羟基-3-甲氧基苯基)庚烷-3,5-二酮 --> 2-羟基-4-甲氧甲基-6-甲基-5-硝基烟腈 --> 5-羟基-4-甲氧甲基-6-甲基-3-吡啶甲醇 --> 4,6-二甲基-2-羟基嘧啶盐酸盐 --> 2-(羧基甲基硫代)-4,6-二甲基嘧啶 一水合物 --> 水合茚三酮 --> 5-溴-2-氯-4,6-二甲基尼古丁腈 --> 17-乙炔基-17-羟基-18-甲基雌甾-5(10),9(11)-二烯-3-酮-3-乙二醇缩酮 --> 2-氨基-4,6-二甲基-3-吡啶甲酰胺 --> 1,4,6-三甲基-3-氨基吡唑并[3,4-B]吡啶 --> 4,6-二甲基
  • 常规方法:用铁桶内衬塑料袋或塑料桶包装;每桶250kg。防火、防潮,贮存于危险品库内。按危险化学品规定贮运。
  • 毒性分级:中毒
  • {Chemica
  • Ac

系列性分类