Malonic acid 丙二酸

CAS 141-82-2 MFCD00002707

化学结构图

141-82-2
SMILES: O=C(O)CC(=O)O

化学属性

Mol. FormulaC3 H4 O4
Mol. Weight104.06
Melting Point132-135°C
Density1.6
Flash Point157°(314°F)
TSCAYes
SolubilitySoluble in water, alcohol. Moderately soluble in pyridine, ether
Boiling Point140 °C at 760 mmHg

别名和识别编码

Chemical NameMalonic acid
Synonym 1,3-Propandisäure 1,3-Propanedioic acid AKOS BBS-00003780 CH2(COOH)2 Carboxyacetic acid DICARBOXYMETHANE Kyselina malonova MAAC MALONIC ACID MALONIC ACID FREE ACID Malonic Acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
Beilstein Registry Number1751370
CAS Number141-82-2
EC Number205-503-0
MDL NumberMFCD00002707
Reaxys-RN1751370
PubChem Substance ID867
Merck Number5710
Chemical Name Translation丙二酸
Wiswesser Line NotationQV1VQ
LabNetwork Molecule IDLN00191443
InChIInChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
Canonical SMILESOC(=O)CC(=O)O
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分类

  • {SNA} Aci
  • {SNA} Acids, Alternative Energy, Electronic Chemicals, Metal Organic Frameworks (MOFs), Micro/NanoElectronics, Organic Linker Molecules, 材料科学
  • {SNA} Acid, Acids and Esters, Additional Standards, Analytical Standards, Certified Reference Materials (CRMs), Flavor and Fragrance Standards, Fluka CRMs for Chromatography (neats), Food & Beverage Standards,
  • {SNA} Acids, Acids & Bases, Chemical Synthesis, Hordeum vulgare (Barley), Organic Acids, Panax ginseng, Phytochemicals by Plant (Food/Spice/Herb), Synthetic Reagents, 细胞生物学, 营养研究

产品应用

  • 测定铍、铜的络合剂。标准碱溶液的标定。生化研究。有机合成。制造巴比妥盐。气相色谱分析标准。

相关文献及参考

  • Short: II/27B
  • Merck: 14,5710 Beilstein:2,566
  • Short: III/5a
  • Knoevenagel condensation with aldehydes yields substituted acrylic (e.g. cinnamic) acids; review: Org. React., 15, 204 (1967). For an example of the Doebner modification, using pyridine as solvent/base, see: Org. Synth. Coll., 3, 425 (1955); a catalytic amount of piperidine often gives superior results; see, e.g.: Org. Synth. Coll., 4, 327 (1963).
  • Merck: 14,5710

安全信息

Precautionary statements
  • 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。
  • 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。
  • 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+
  • P304+P340
  • P304+P340+P312
  • P305+P351+P338
  • P332+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
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
GHS Symbol
Signal word Danger
Hazard statements
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H302 Harmful if swallowed 吞食有害
  • H318 Causes serious eye damage 严重伤害眼睛
WGK Germany1
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;
  • S36/37/39 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;
  • S36/39 Wear suitable protective clothing and eye/face protection 穿戴适当的防护服和眼睛/面保护;
  • S37/39 Wear suitable gloves and eye/face protection 穿戴适当的手套和眼睛/面保护;
  • 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;
Risk Statements
  • 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
  • R36/37/38 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
RTECSOO0175000
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes Xn
Storage condition +4°C Store at RT. Store at room temperature 密封保存
Packing GroupIII
UN Number 3261
TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 10 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   BIOFX* BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets.  (1810
   Frontage Rd., Northbrook, IL 60062)  Volume(issue)/page/year: 22-3/1971

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

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 300 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

TYPE OF TEST            : LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >8900 mg/m3/1H
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   BIOFX* BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets.  (1810
   Frontage Rd., Northbrook, IL 60062)  Volume(issue)/page/year: 22-3/1971

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 4 gm/kg
TOXIC EFFECTS :
   Tumorigenic - active as anti-cancer agent
REFERENCE :
   BIJOAK Biochemical Journal.  (Biochemical Soc. Book Depot, POB 32, Commerce
   Way, Colchester, Essex CO2 8HP, UK)  V.1-    1906- Volume(issue)/page/year:
   34,1196,1940

TYPE OF TEST            : LD50 - Lethal do

TYPE OF TEST            : Morphological transformation
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 10080 mg/kg/6W
REFERENCE :
   CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House,
   Southfield Road, Eynsham, Oxford OX8 1JJ, UK)  V.1-    1980-
   Volume(issue)/page/year: 9,387,1988

其他信息

  • 下游产品:3-(3-吡啶基)丙酸 --> 2-乙酰苯甲酸 --> 3-(3-氯苯基)丙酸 --> 3-(4-甲苯)丙酸 --> 3-(1-萘基)丙酸 --> 3-(3-吡啶)丙烯酸 --> 丙位癸内酯 --> 吲唑-3-乙酸 --> 2-
  • 用途三:丙二酸是杀菌剂稻瘟灵的中间体,也是植物生长调节剂吲熟酯的中间体。
  • 用途二:主要
  • 二元酸:丙二酸又称甲烷二羧酸、胡萝卜酸、缩苹果酸、甜菜酸。有3种晶型,其中两个为三斜晶系,一个为单斜晶系。从乙醇中结晶者为三斜晶系白色晶体。相对分子质量104.06。相对密度1.631(15℃)。熔点135.6℃。140℃分解为乙酸及二氧化碳。在1.067×103~1.333×103Pa真空下不分解,而直接升华。不溶于苯,溶于水 61.1(0℃)、73.5(20℃)、92.6(50℃)、乙醇 57(20℃)、乙醚5.7(20℃),微溶于吡啶。遇高锰酸钾分解为甲酸及二氧化碳。丙二酸为二元酸,具有二元酸的典型反应性,例如丙二酸的亚甲基具有活性,可进行加成、烷基化、胺化、卤化等反应;其两个羧基相距很近,可以脱水;可与醇进行酯化;加热脱羧;与羰基化合物缩合;与含有活泼双键的化合物加成。丙二酸的两个羧基中的羟基全被乙氧基取代(见取代反应)而生成的化合物丙二酸二乙酯,丙二酸二乙酯是重要的有机合成原料,用于染料和药物合成。因分子中含有活泼的亚甲基,可先与醇钠作用生成丙二酸酯钠,再与各种活泼卤代物作用生成取代的丙二酸酯,将它水解失羧可制得各种一元、二元羧酸及其他酮酸等化合物。如将取代的丙二酸酯与尿素反应可制得一种常用催眠药巴比妥。 由于丙二酸加热后生成二氧化碳和水,没有污染问题,所以可直接用作铝表面处理剂;也是生产农药杀菌剂富士一号、除草剂枯杀达的原料;医药行业使用丙二酸制备利尿药苯磺唑酮、抗炎药羟苯保泰松、镇静药溴甲辛托品等。此外,丙二酸及其酯类广泛用作医药中间体,如可以制造巴比妥类药物,维生素B1和B6等,丙二酸的酯类常用于有机合成,还用作粘接剂、香料、树脂添加剂、电镀抛光剂、焊接助熔剂等。 以上信息由Chemicalbook的晓楠编辑整理。
  • MOL 文件:141-82-2.mol
  • 用途四:丙二酸及其酯主要用于香料、粘合剂、树脂添加剂、医药中
  • 上游原料:盐酸 --> 丙酮 --> 氰化钠 --> 丙二酸二乙酯 --> 氯乙酸 --> 氯乙酸钠 --> 氰乙酸 --> 二乙酯 --> 丙二酸钠盐一水合 --> 丙二酸钙
  • Acros Organics:丙二酸 Malonic acid, 99%(141-82-2)
  • MSDS 信息:丙二酸(141-82-2).msds
  • 丙二酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 30111926 丙二酸;胡萝卜酸;甜菜酸;
  • 图谱信息:丙二酸(141-82-2)质谱(MS) 丙二酸(141-82-2)Raman光谱 丙二酸(141-82-2)红外图谱(IR1) 丙二酸(1
  • 用途一:用作络合剂,也用于巴比土盐的制备等
  • Alfa Aesar:马来酸,ReagentGrade,99.5+% Malonic acid, Reagent Grade, 99.5+%(141-82-2)
  • 制备方法:实验室采用氯乙酸为原料,用NaOH或Na2CO3中和生成氯乙酸钠盐,此钠盐与KCN(或NaCN)反应后得α-氰基乙酸钠,再经碱性水解、钙盐置换、酸化后制得丙二酸。化学反应方程式如下:
  • 海关编码:29171910
  • Sigma Aldrich:141-82-2(sigmaaldrich)
  • 下游产品:3-(3-吡啶基)丙酸 --> 2-乙酰苯甲酸 --> 3-(3-氯苯基)丙酸 --> 3-(4-甲苯)丙酸 --> 3-(1-萘基)丙酸 --> 3-(3
  • 图谱信息:丙二酸(141-82-2)质谱(MS) 丙二酸(141-82-2)Raman光谱 丙二酸(141-82-2)红外图谱(IR1) 丙二酸(141-82-2)核磁图( 1 HNMR) 丙二酸(141-82-2)红外图谱(IR2)
  • {Chemica

系列性分类