CAS: 79-16-3; N-Methylacetamide

该化合物是一种极地蛋白溶剂,配有化学配方C3H7NO,其特点是其高电常量,热稳定性和溶解多种有机和无机化合物的能力.NMA因其有利的溶解特性,通常用于制药合成,聚合物研究,并作为有机化学的反应媒介.NMA的低挥发性和非腐蚀性性质使它适合高温应用.此外,NMA是研究生物化学中的基联和分子相互作用的模范化合物.该化合物在标准实验室条件下处理,由于它的湿质性质,注意适当的储存和处理.

⚠️《化妆品禁用原料目录》
英文名称N-Methylacetamide
中文名称N-甲基乙酰胺
IUPAC名称N-methylacetamide
其它别名N-Methylacetamide, Purum, >=98.0% (Gc); X 44; Ch3Conhch3; Acetamide, Methyl-; N-Methyl Acetamide; Acetamide, N-Methyl-; N-Methylacetamide(Nma); Acetylmethylamine; Nsc
CAS编号79-16-3
MFCD编号:MFCD00008683
EINECS号:201-182-6
FDA UNII编号:V0T777481M
分子式:C3H7NO
分子量:73.09
产品CID: 1785972
产品分类有机原料 → 氨基化合物 → 酰胺类化合物

相似结构搜索
产品信息参考;
InChIKey: OHLUUHNLEMFGTQ-UHFFFAOYSA-N
InChI=1S/C3H7NO/c1-3(5)4-2/h1-2H3,(H,4,5)…
计算化学: 氢键受体数1.0氢键供体数1.0可旋转键数0.0

物理性质

熔点26-28 °C(文献)
沸点125.0±23.0 °C at 760 mmHg
闪点46.2±11.9 °C
密度0.9±0.1 g/cm3
PH:7 (H2O)
pKa:16.61±0.46(预测)
PSA:29.1
LogP:-0.09
折射率1.410
蒸汽压5.8±0.5 mmHg at 25°C
溶解性Miscible With Ethanol, Ether, Acetone, Water, Chloroform, Benzene
敏感性1. 化学性质：与氯化氢作用能生成两种形式的盐，即CH3CONHCH3·HCl(熔点67.2～69.4°C)和(CH3CONHCH3)2·HCl。与金属钠在室温下几乎不发生反应。与亚硝酸反应生成亚硝基化合物。与乙酸酐回流煮沸生成N-甲基二乙酰胺。受酸或碱的作用，N-甲基乙酰胺都能发生水解。2. 存在于烟气中。
外观形态无色固体
储存条件惰性气氛,室温
产品应用该品为农药,医药等有机合成的中间体.
性质描述白色针状结晶.熔点30.55°C(28°C),沸点206°C,140.5°C(12kPa),相对密度0.9571(25/4°C),折光率1.4301,闪点108°C.溶于水,乙醇,苯,醚,氯仿,不溶于石油醚.

欧盟法规

统一分类与标签REACH注册ECHA物质工作场所安全标识要求食品接触材料-禁用CMR物质化妆品禁用物质清单ECHA物质C&L通报REACH预注册欧盟候选物质清单废弃物危险特性清单

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合成工艺路线路线简述

合成目标产物 N-Methylacetamide 主要起始原料 Trimethyl Orthoacetate And Methylamine Hydrochloride
38100-40-2 = 79-16-3
反应条件:1.1 Reagents: Potassium Carbonate,1,4-Cyclohexadiene Catalysts: Eosin Solvents: Acetone; 16 H,Rt
标题:Visible-Light-Mediated Synthesis Of Amidyl Radicals: Transition-Metal-Free Hydroamination And N-Arylation Reactions
作者:Davies,Jacob; Svejstrup,Thomas D.; Fernandez Reina,Daniel; Sheikh,Nadeem S.; Leonori,Daniele
参考文献:Journal Of The American Chemical Society 日期:2016 卷标:138(26) 页码:8092-8095]

1445-45-0 + 593-51-1 = 79-16-3
反应条件:1.1 Solvents: Methanol; 15 Min,Rt -> 135 °C
标题:Direct Preparation Of Amides From Amine Hydrochloride Salts And Orthoesters: A Synthetic And Mechanistic Perspective
作者:Di Grandi,Martin J.; Bennett,Caitlin; Cagino,Kristen; Muccini,Arnold; Suraci,Corey; Et Al
参考文献:Synthetic Communications 日期:2015 卷标:45(22) 页码:2601-2607]

108-22-5 = 79-16-3
反应条件:1.1 3 H,60 °C
标题:Isopropenyl Acetate,A Remarkable,Cheap And Acylating Agent Of Amines Under Solvent- And Catalyst-Free Conditions: A Systematic Investigation
作者:Pelagalli,Romina; Chiarotto,Isabella; Feroci,Marta; Vecchio,Stefano
参考文献:Green Chemistry 日期:2012 卷标:14(8) 页码:2251-2255]

127-06-0 = 79-16-3
反应条件:1.1 Catalysts: Phosphorus Pentoxide,Trifluoromethanesulfonic Acid Solvents: Dimethylformamide
标题:Homogeneous Liquid-Phase Beckmann Rearrangement Of Oximes Catalyzed By Phosphorous Pentoxide And Accelerated By A Fluorine-Containing Strong Acid
作者:Sato,H.; Yoshioka,H.; Izumi,Y.
参考文献:Journal Of Molecular Catalysis A: Chemical 日期:1999 卷标:149(1-2) 页码:25-32]

127-06-0 = 79-16-3
反应条件:1.1 Catalysts: P-Toluenesulfonic Acid1.2 Solvents: Diethyl Ether1.3 Reagents: Sodium Bicarbonate Solvents: Water
标题:Facile Ptsh-Catalyzed Beckmann Rearrangement Of Ketoximes In Solid State
作者:Ponnusamy,S.; Pitchumani,K.
参考文献:Indian Journal Of Chemistry 日期:1999 卷标:(7) 页码:861-864]

127-06-0 = 79-16-3
反应条件:1.1 Catalysts: Phosphorus Pentoxide,Trifluoromethanesulfonic Acid Solvents: Dimethylformamide
标题:Process For Producing Amides By Liquid-Phase Rearrangement Of Oximes Catalyzed By Phosphorus Pentoxide And Dialkyl Amides Or Sulfoxides
参考文献:European Patent Organization]

= 79-16-3
反应条件:1.1 Catalysts: Basic Alumina; 25 Min,70 °C
标题:Nano Rod-Shaped And Reusable Basic Al2O3 Catalyst For N-Formylation Of Amines Under Solvent-Free Conditions: A Novel,Practical And Convenient Nose' Approach
作者:Das,Vijay Kumar; Devi,Rashmi Rekha; Raul,Prasanta Kumar; Thakur,Ashim Jyoti
参考文献:Green Chemistry 日期:2012 卷标:14(3) 页码:847-854]

127-06-0 = 79-16-3
反应条件:1.1 Catalysts: Silica,Sulfuric Acid Solvents: 1,4-Dioxane; 24 H,Rt
标题:A Novel Method For Beckmann Rearrangement Of Oximes With Silica Sulfuric Acid Under Mild Condition
作者:Xiao,Lin Fei; Peng,Jia Jian; Xia,Chun Gu
参考文献:Chinese Chemical Letters 日期:2006 卷标:17(5) 页码:617-620]

127-06-0 = 79-16-3
反应条件:1.1 Catalysts: Zinc Chloride; 2 H,130 °C
标题:High-Yield And High-Efficiency Conversion Of Cyclohexanone Oxime To ε-Caprolactam In A Green And Facile Reaction Process Over Deep Eutectic Solvents
作者:Sun,Shiqin; Liu,Shiwei; Yu,Fengli; Zhang,Jian; Xing,Weiguo; Et Al
参考文献:Chemical Engineering Science 日期:2022 卷标:253]

127-06-0 = 79-16-3
反应条件:1.1 Catalysts: 2255309-71-6; 2 H,100 °C
标题:Reusable Deep Eutectic Solvents For Clean ε-Caprolactam Synthesis Under Mild Conditions
作者:Sun,Shiqin; Liu,Shiwei; Yu,Fengli; Zhang,Jian; Xing,Weiguo; Et Al
参考文献:Acs Sustainable Chemistry & Engineering 日期:2022 卷标:10(4) 页码:1675-1688]

38100-40-2 = 79-16-3
反应条件:1.1 Reagents: Potassium Carbonate,1,4-Cyclohexadiene Solvents: Acetone; 1.5 H,Rt
标题:Regioselective Intramolecular Allene Amidation Enabled By An Eda Complex
作者:Liu,Lu; Ward,Robert M.; Schomaker,Jennifer M.
参考文献:Chemistry - A European Journal 日期:2020 卷标:26(61) 页码:13783-13787]

13115-24-7 + 87-87-6 = 79-16-3 + 877-13-4 + 87-88-7 + 118-75-2
反应条件:1.1 Solvents: Water; 1 H,Ph 7.4,37 °C
标题:An Unexpected New Pathway For Nitroxide Radical Production Via More Reactive Nitrogen-Centered Amidyl Radical Intermediate During Detoxification Of The Carcinogenic Halogenated Quinones By N-Alkyl Hydroxamic Acids
作者:Zhu,Ben-Zhan; Et Al
参考文献:Free Radical Biology & Medicine 日期:2020 卷标:146 页码:150-159]

593-77-1 = 79-16-3 + 877-13-4 + 87-88-7 + 118-75-2
反应条件:1.1 Reagents: Sodium Carbonate Solvents: Methanol; 0 °C; 30 Min,0 °C2.1 Solvents: Water; 1 H,Ph 7.4,37 °C
标题:An Unexpected New Pathway For Nitroxide Radical Production Via More Reactive Nitrogen-Centered Amidyl Radical Intermediate During Detoxification Of The Carcinogenic Halogenated Quinones By N-Alkyl Hydroxamic Acids
作者:Zhu,Ben-Zhan; Et Al
参考文献:Free Radical Biology & Medicine 日期:2020 卷标:146 页码:150-159]

53376-60-6 = 79-16-3
反应条件:1.1 Reagents: Water Catalysts: 1,3-Bis(Diphenylphosphino)Propane,Palladium Trifluoroacetate Solvents: Acetonitrile; 10 Min,Rt1.2 20 H,80 °C
标题:Hydrolytic Deallylation Of N-Allyl Amides Catalyzed By Pdii Complexes
作者:Ohmura,Naoya; Nakamura,Asami; Hamasaki,Akiyuki; Tokunaga,Makoto
参考文献:European Journal Of Organic Chemistry 日期:2008 卷标:(30) 页码:5042-5045]

= 79-16-3
反应条件:1.1 Catalysts: Magnesium Oxide; 60 Min,70 °C
标题:Recyclable,Highly Efficient And Low Cost Nano-Mgo For Amide Synthesis Under Sfrc: A Convenient And Greener Nose' Approach
作者:Das,Vijay Kumar; Devi,Rashmi Rekha; Thakur,Ashim Jyoti
参考文献:Applied Catalysis 日期:2013 卷标:456 页码:118-125]

53376-60-6 = 79-16-3
反应条件:1.1 Reagents: Potassium Periodate Catalysts: Dichloro[(1,2,3,6,7,10,11,12-η)-2,6,10-Dodecatriene-1,12-Diyl]Ruthenium Solvents: Water; 3 H,100 °C
标题:Efficient Tandem Process For The Catalytic Deprotection Of N-Allyl Amides And Lactams In Aqueous Media: A Novel Application Of The Bis(Allyl)-Ruthenium(Iv) Catalysts [ru(η3:η2:η3-C12H18)Cl2] And [{ru(η3:η3-C10H16)(μ-Cl)Cl}2]
作者:Cadierno,Victorio; Gimeno,Jose; Nebra,Noel
参考文献:Chemistry - A European Journal 日期:2007 卷标:13(23) 页码:6590-6594]

= 79-16-3
反应条件:1.1 Catalysts: 1-(4-Sulfobutyl)-3-Methylimidazolium Trifluoromethanesulfonate; 7 H,Reflux
标题:Synthesis Of Diverse Libraries Of Carboxamides Via Chemoselective N-Acylation Of Amines By Carboxylic Acids Employing Bronsted Acidic Il [bmim(So3H)][otf]
作者:Savanur,Hemantkumar M.; Malunavar,Shruti S.; Prabhala,Pavankumar; Sutar,Suraj M.; Kalkhambkar,Rajesh G.; Et Al
参考文献:Tetrahedron Letters 日期:2019 卷标:60(42)]

127-06-0 = 79-16-3
反应条件:1.1 Catalysts: Methanol,1,1,1-Trifluoro-,1-(Hydrogen Sulfate),Indium(3+) Salt (3:1) Solvents: Acetonitrile
标题:Indium Trifluoromethanesulfonate (In(Otf)3)-A New Catalyst For Beckmann Rearrangement Of Ketoximes And Facile Dehydration Of Aldoximes
作者:Barman,Dhiren C.; Gohain,Mukut; Prajapati,Dipak; Sandhu,Jagir S.
参考文献:Indian Journal Of Chemistry 日期:2002 卷标:(1) 页码:154-156]

127-06-0 = 79-16-3
反应条件:1.1 Catalysts: Bismuth Trichloride
标题:Microwave Induced Bismuth Trichloride Catalysed Beckmann Rearrangement Of Oximes
作者:Thakur,Ashim J.; Boruah,Anima; Prajapati,Dipak; Sandhu,Jagir S.
参考文献:Synthetic Communications 日期:2000 卷标:30(12) 页码:2105-2111

丙酮肟置于氯磺酸体系中,用甲苯作为反应溶剂,化学反应 0.5H,以43%的收率获得产物n-甲基乙酰胺
参考文献:高效的贝克曼重排和肟脱水
标题:高效的贝克曼重排和肟脱水
摘要:在温和的条件下,使用甲苯作作为反应溶剂,在氯磺酸存在下,多种酮肟的贝克曼重排反应可以进行,并具有出色的转化率和选择性.该方法也可用于醛肟的脱水以获得相应的腈.
DOI:10.1016/j.Tetlet.2004.11.116

海关参考信息

2912110000-甲醛
2912120000-乙醛
2924199090-其他无环酰胺
2921199090-其他无环单胺
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专利信息

专利号:US-7589170-B1
优先权日:1998-09-25
标题 :Synthesis of cyclic peptides
发明人：SMYTHE MARK LESLIE; MEUTERMANS WIM DENIS FRANS; BOURNE GREGORY THOMAS; MCGEARY ROSS PETER
权利人:UNIV QUEENSLAND
摘要:This invention relates to methods for preparing cyclic peptides and peptidomimetic compounds in solution and bound to solid supports, and to cyclic peptide or peptidomimetic libraries for use in drug screening programs. In particular, the invention relates to a generic strategy for synthesis of cyclic peptides or peptidomimetics that enables the efficient synthesis under mild conditions of a wide variety of desired compounds. Two approaches were evaluated for their improvements in solution and solid phase synthesis of small cyclic peptides: positioning reversible N-amide substituents in the sequence; and applying native ligation chemistry in an intramolecular sense. Systematic investigation of the effects of preorganising peptides prior to cyclisation by using peptide cyclisation auxiliaries, and developing new linkers and peptide cyclisation auxiliaries to aid cyclic peptide synthesis gives surprising improvements in both yields and purity of products compared to the prior art methods. The combination of these technologies provides a powerful generic approach for the solution and solid phase synthesis of small cyclic peptides. The ring contraction and N-amide substitution technology of the invention provide improved methods for the synthesis of cyclic peptides and peptidomimetics. When used in conjunction with linker strategies, this combination provides solid-phase avenues to cyclic peptides and peptidomimetics.

专利号:US-11548898-B2
优先权日:2017-07-06
标题 :Synthesis of halichondrins
发明人：KISHI YOSHITO; AI YANRAN; YE NING; WANG QIAOYI; YAHATA KENZO; ISO Kentaro; NAINI SANTHOSH REDDY; YAMASHITA SHUJI; LEE JIHOON; OHASHI ISAO; FUKUYAMA TAKASHI
权利人:HARVARD COLLEGE; EISAI R&D MAN CO LTD
摘要:The present invention provides methods for the synthesis of ketones involving a Ni/Zr-mediated coupling reaction. The Ni/Zr-mediated ketolization reactions can be used in the synthesis of halichondrins (e.g., halichondrin A, B, C; homohalichondrin A, B, C; norhalichondrin A, B, C), and analogs thereof. Therefore, the present invention also provides synthetic methods useful for the synthesis of halichondrins, and analogs thereof. Also provided herein are compounds (i.e., intermediates) useful in the synthesis of halichondrins, and analogs thereof. In particular, the present invention provides methods and compounds useful in the synthesis of compound of Formula (H3-A).

专利号:US-2008287649-A1
优先权日:2006-12-29
标题 :Methods for the synthesis of cyclic peptides
发明人：CHEN LIN; HAN YEUN-KWEI; ROBERTS CHRISTOPHER R
权利人:CHEN LIN; HAN YEUN-KWEI; ROBERTS CHRISTOPHER R
摘要:Methods for the synthesis of cyclic peptides are provided, as well as novel dipeptide compounds. The methods include the solid phase synthesis of a dipeptide, which is the coupled to a second peptide in a solid phase reaction. The peptide is then cyclized following the coupling reaction. The methods and dipeptides are particularly useful for the synthesis of MC-4 receptor agonist peptides.

专利号:US-2004242897-A1
优先权日:2002-07-31
标题 :Universal support media for synthesis of oligomeric compounds
发明人：GUZAEV ANDREI P; MANOHARAN MUTHIAH
摘要:Compounds for the synthesis of oligomeric compounds, particularly oligonucleotides and oligonucleotide mimetics, are provided. In addition, methods for functionalizing a support medium with a first monomeric subunit and methods for the synthesis of oligomeric compounds utilizing the novel compounds bound to support media are provided.

专利号:US-6770436-B1
优先权日:1996-11-14
标题:Chemical amplification for the synthesis of patterned arrays
发明人：BEECHER JODY E; GOLDBERG MARTIN J; MCGALL GLENN H
权利人:AFFYMETRIX INC
摘要:Radiation-activated catalysts (RACs), autocatalytic reactions, and protective groups are employed to achieve a highly sensitive, high resolution, radiation directed combinatorial synthesis of pattern arrays of diverse polymers. When irradiated, RACs produce catalysts that can react with enhancers, such as those involved in autocatalytic reactions. The autocatalytic reactions produce at least one product that removes protecting groups from synthesis intermediates. This invention has a wide variety of applications and is particularly useful for the solid phase combinatorial synthesis of polymers.

专利号:US-8829157-B2
优先权日:2004-06-14
标题:Process for the synthesis of cyclic heptapeptide
发明人：SAKSENA DIVYA LAL; MURALIDHARAN CHANDRAKESAN; LOBO LESTER; PAWAR DIGAMBER SHRIPATI; MOHE NIKHIL UMESH; TARUR RADHAKISHNAN VENKATASUBRAMANIAN
权利人:SAKSENA DIVYA LAL; MURALIDHARAN CHANDRAKESAN; LOBO LESTER; PAWAR DIGAMBER SHRIPATI; MOHE NIKHIL UMESH; TARUR RADHAKISHNAN VENKATASUBRAMANIAN; USV LTD
摘要:The present invention relates to an improved process for the large scale synthesis of cyclic heptapeptide using Fmoc solid phase synthesis technique. The described process assembles the peptide on a solid support resin by coupling to one another by peptide bonds to obtain a peptide wherein the coupling of cysteine to the resin employs a combination of solvents to reduce cysteine racemization. The process described relates to the use of C1-C4 alcohols as total substitute to organic nitriles thus making the process cost effective, non-toxic and eco-friendly.

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合成参考文献

参考文献:10.1364/boe.2.001781
摘要:Pham H, Ding H, Sobh N, Do M, Patel S, Popescu G. Off-axis quantitative phase imaging processing using CUDA: toward real-time applications. Biomed Opt Express. 2011 Jul 01;2(7):1781–93.
参考文献:10.1007/s00894-011-1166-5
摘要:Xiao X, Tan Y, Zhu L, Guo Y, Wen Z, Li M, Pu X, Tian A. Effects of the position and manner of hydration on the stability of solvated N-methylacetamides and the strength of binding between N-methylacetamide and water clusters: a computational study. Journal of Molecular Modeling. 2011 Jul 15;18(4):1389–99. doi: 10.1007/s00894-011-1166-5.
参考文献:10.4061/2011/158105
摘要:Nambu M, Ishihara M, Kishimoto S, Yanagibayashi S, Yamamoto N, Azuma R, Kanatani Y, Kiyosawa T, Mizuno H. Stimulatory Effect of Autologous Adipose Tissue-Derived Stromal Cells in an Atelocollagen Matrix on Wound Healing in Diabetic db/db Mice. Journal of Tissue Engineering. 2011 Sep 09;(). doi: 10.4061/2011/158105.

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CAS: 79-16-3; N-Methylacetamide

物理性质

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上下游产品

合成工艺路线路线简述

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