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N-甲基甲酰胺

31篇引用文献 COA COA
    级别和纯度:
  • ≥99%
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有机砌块 (466) 羰基化合物 (2389) 胺 ∩ 脂链烃 (2) 脂肪链类化合物 (268) 酰胺 (351) 非杂环砌块 (8221)
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基本描述

别名 甲基甲酰胺 | N-甲酰基甲胺
英文别名 N-Formylmethylamine
规格或纯度 ≥99%
英文名称 N-Methylformamide
运输条件 常规运输
产品介绍

N-甲基甲酰胺（NMF）是一种甲酰胺衍生物，被广泛用作有机溶剂。NMF分子含有C=O和N-H基团，因此，它可以作为质子供体和受体。它在小鼠中的抗肿瘤活性已被评估。NMF的光外差检测光学Kerr效应（OHD-OKE）光谱评估已被报道。由于NMF具有重要的物理性质，如高介电常数、高溶解度、低电导率和两性性质，因此，它适合用作毛细管电泳研究的分离介质。

N-甲基甲酰胺可用于制备：

• Li2S-P2S5 固体电解质（SE）

• 质子化层状硅酸盐（麦烃硅钠石）的夹层压缩材料

• Li3PS4 固体电解质

N-Methylformamide (NMF), a formamide derivative, is widely employed as an organic solvent. NMF molecule contains C=O and N-H groups, so it can act as a proton donor and acceptor. Its antitumor activities in mice have been assessed. Optical-heterodyne-detected optical Kerr effect (OHD-OKE) spectroscopic evaluation of NMF has been reported. Due to its important physical properties such as high dielectric constant, high solubility, low conductivity and amphiprotic nature, it is suitable for use as a separation medium in capillary electrophoresis studies.

N-Methylformamide may be employed in the preparation of the following:

• Li2S-P2S5 solid electrolytes (SE) 

• interlayer-condensed materials of protonated layered silicate (magadiite) 

• Li3PS4 solid electrolyte


Application

N-Methylformamide is used to prepare methyl isocyanate. It is used as an extraction solvent for aromatic hydrocarbons and acts as a ligand in coordination chemistry. It is employed as a solvent in oil refineries and in aluminum electrolytic capacitors. Further, it is used as a reagent in organic synthesis. In addition to this, it is used as an investigational anticancer drug and an intermediate in the production of some pharmaceutical compounds.
纯度 ≥99%

关联靶点（人）

A498 (42825 活性数据)
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ACHN (49357 活性数据)
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CAKI-1 (44928 活性数据)
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CCRF-CEM (65223 活性数据)
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COLO 205 (50209 活性数据)
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DLD-1 (17511 活性数据)
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DMS-273 (14108 活性数据)
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DU-145 (51482 活性数据)
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HL-60 (67320 活性数据)
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HT-29 (80576 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
K562 (73714 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
KM12 (47707 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
M14 (47487 活性数据)
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MCF7 (126967 活性数据)
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MOLT-4 (49676 活性数据)
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OVCAR-3 (48710 活性数据)
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OVCAR-4 (44535 活性数据)
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OVCAR-5 (45555 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
OVCAR-8 (47708 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PC-3 (62116 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
RPMI-8226 (44974 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
RXF 393 (41971 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SF-295 (48000 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SK-MEL-2 (46422 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SK-MEL-28 (48833 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SK-MEL-5 (47095 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SK-OV-3 (52876 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SN12C (47755 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SNB-19 (46794 活性数据)
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SNB-78 (14240 活性数据)
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TK-10 (45540 活性数据)
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U-251 (51189 活性数据)
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UACC-257 (46019 活性数据)
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UACC-62 (47335 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
UO-31 (46270 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
XF498 (12972 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
786-0 (47912 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
A549 (127892 活性数据)
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NCI/ADR-RES (33767 活性数据)
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T47D (39041 活性数据)
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EKVX (44102 活性数据)
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NCI-H322M (45589 活性数据)
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HCC 2998 (41480 活性数据)
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HCT-116 (91556 活性数据)
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HOP-18 (11577 活性数据)
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HOP-92 (41141 活性数据)
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Hs-578T (29457 活性数据)
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NCI-H460 (60772 活性数据)
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SF-268 (49410 活性数据)
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IGROV-1 (47897 活性数据)
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关联靶点（其它种属）

Mus musculus (284745 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
P388 (20296 活性数据)
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P388/ADR (1216 活性数据)
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SARS-CoV-2 (38078 活性数据)
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作用机制

作用机制 Action Type target ID Target Name Target Type Target Organism Binding Site Name 参考文献

名称和识别符

PubChem SID 504753441
EC号 204-624-6
分子类型 小分子
IIUPAC Name N-methylformamide
INCHI 1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)
InChi Key ATHHXGZTWNVVOU-UHFFFAOYSA-N
Smiles CNC=O
Isomeric SMILES CNC=O
分子量 59.07
Beilstein号 1098352
Reaxy-Rn 1098352
Reaxys-RN link address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1098352&ln=

化学和物理性质

溶解性 Miscible with water, acetone and ethanol. Immiscible with ether.
密度 1.01
折光率 1.43
闪点(℉) 208 °F
闪点(℃) 98 °C
沸点 183°C
熔点 -5°C(lit.)
分子量 59.070 g/mol
XLogP3 -1.000
氢键供体数Hydrogen Bond Donor Count 1
氢键受体数Hydrogen Bond Acceptor Count 1
可旋转键计数Rotatable Bond Count 0
精确质量Exact Mass 59.0371 Da
单同位素质量Monoisotopic Mass 59.0371 Da
拓扑极表面积Topological Polar Surface Area 29.100 Ų
重原子数Heavy Atom Count 4
形式电荷Formal Charge 0
复杂度Complexity 20.000
同位素原子数Isotope Atom Count 0
定义的原子立体中心计数Defined Atom Stereocenter Count 0
未定义的原子立体中心计数Undefined Atom Stereocenter Count 0
定义的键立体中心计数Defined Bond Stereocenter Count 0
未定义的键立体中心计数Undefined Bond Stereocenter Count 0
所有立体化学键的总数The total count of all stereochemical bonds 0
共价键合单元计数Covalently-Bonded Unit Count 1

安全和危险性（GHS）

象形图 GHS07,   GHS08
信号词 危险
危险声明

H303: 要是吞了可能有害

H312: 皮肤接触有害

H360: 可能损害生育力或未出生的孩子
预防措施声明

P201: 使用前获取特殊说明

P202: 在阅读并理解所有安全预防措施之前，不要进行操作。

P280: 戴防护手套/穿防护服/戴防护眼罩/戴防护面具。

P321: 特殊处理（请参阅此标签上的...）。

P302+P352: 如皮肤沾染：用水充分清洗。

P362+P364: 脱掉沾污的衣服，清洗后方可重新使用。

P405: 密闭存放

P501: 将内容物/容器处理到。。。

P203: 使用前，获取、阅读并遵守所有安全说明。

P318: 如果暴露或担心，请就医。

P317: 寻求紧急医疗救助。
WGK Germany 1
RTECS LQ3000000
Merck Index 6076
个人防护装备 Eyeshields,Faceshields,full-face respirator (US),Gloves,multi-purpose combination respirator cartridge (US),type ABEK (EN14387) respirator filter

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引用文献

1. K Clagett-Carr,G Sarosy,J Plowman,D F Hoth,B Leyland-Jones.  (1988-05-01)  N-methylformamide: cytotoxic, radiosensitizer, or chemosensitizer..  Journal of clinical oncology : official journal of the American Society of Clinical Oncology,  6  ((5)): (906-918).  [PMID:3284976]
2. Zhao D, Sonawane ND, Levin MH, Yang B.  (2007)  Comparative transport efficiencies of urea analogues through urea transporter UT-B..  Biochim Biophys Acta,  1768  (7): (1815-21).  [PMID:17506977]
3. A Gescher,N W Gibson,J A Hickman,S P Langdon,D Ross,G Atassi.  (1982-06-01)  N-methylformamide: antitumour activity and metabolism in mice..  British journal of cancer,  45  ((6)): (843-850).  [PMID:7201320]
4. H Igisu,M Matsuoka.  (1999-10-30)  [N-methylformamide in urine]..  Nihon rinsho. Japanese journal of clinical medicine,  57 Suppl  (460-462).  [PMID:10543154]
5. J Mráz,J Cimlová,V Stránský,H Nohová,R Kicová,P Simek.  (2005-11-18)  N-Methylcarbamoyl-lysine adduct in globin: a new metabolic product and potential biomarker of N, N-dimethylformamide in humans..  Toxicology letters,  162  ((2-3)): (211-218).  [PMID:16289959]
6. Abdul Mutlib,Ping Jiang,Jim Atherton,Leslie Obert,Seva Kostrubsky,Steven Madore,Sidney Nelson.  (2006-10-17)  Identification of potential genomic biomarkers of hepatotoxicity caused by reactive metabolites of N-methylformamide: Application of stable isotope labeled compounds in toxicogenomic studies..  Chemical research in toxicology,  19  ((10)): (1270-1283).  [PMID:17040096]
7. Dar-Bin Shieh,Chia-Chun Chen,Tung-Sheng Shih,Huo-Mu Tai,Yau-Hui Wei,Ho-Yuan Chang.  (2007-01-27)  Mitochondrial DNA alterations in blood of the humans exposed to N,N-dimethylformamide..  Chemico-biological interactions,  165  ((3)): (211-219).  [PMID:17254560]
8. Johan Sjödahl,Peter Lindberg,Johan Roeraade.  (2007-02-23)  Separation of oligonucleotides in N-methyl-formamide-based polymer matrices by capillary electrophoresis..  Journal of separation science,  30  ((1)): (104-109).  [PMID:17313148]
9. Jakub Chalupský,Jirí Vondrásek,Vladimír Spirko.  (2008-01-08)  Quasiplanarity of the peptide bond..  The journal of physical chemistry. A,  112  ((4)): (693-699).  [PMID:18177024]
10. D O Futino,M C B Mendes,W N L Matos,R G Mondadori,C M Lucci.  (2008-11-21)  Glycerol, methyl-formamide and dimethyl-formamide in canine semen cryopreservation..  Reproduction in domestic animals = Zuchthygiene,  45  ((2)): (214-220).  [PMID:19019075]
11. Edward M Kosower,Gil Markovich,Galina Borz.  (2009-03-31)  N-methylformamide, a hyperplectic model for peptides in thin film infrared spectroscopy on planar AgX..  The journal of physical chemistry. B,  113  ((16)): (5622-5632).  [PMID:19326884]
12. Jun He,Jing-ping Zhou,Pei Wang.  (2009-04-09)  [High performance liquid chromatography for determination of N-acetyl-S-(N-methylformamide) cysteine in human urine derivative oscillopolarography for determination of urine arsenic]..  Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases,  27  ((2)): (103-104).  [PMID:19351480]
13. Diane Fournier,Jalal Hawari,Annamaria Halasz,Sheryl H Streger,Kevin R McClay,Hisako Masuda,Paul B Hatzinger.  (2009-06-23)  Aerobic biodegradation of N-nitrosodimethylamine by the propanotroph Rhodococcus ruber ENV425..  Applied and environmental microbiology,  75  ((15)): (5088-5093).  [PMID:19542346]
14. Kwame Frimpong,Joseph Wzorek,Claire Lawlor,Katharine Spencer,Thomas Mitzel.  (2009-07-29)  Use of N-methylformamide as a solvent in indium-promoted Barbier reactions en route to enediyne and epoxy diyne formation: comparison of rate and stereoselectivity in C-C bond-forming reactions with water..  The Journal of organic chemistry,  74  ((16)): (5861-5870).  [PMID:19634900]
15. Jolanta Swiergiel,Jan Jadzyn.  (2009-10-07)  Conductivity dynamics and static dielectric permittivity of highly conducting molecular liquids studied with impedance spectroscopy. Formamides..  The journal of physical chemistry. B,  113  ((43)): (14225-14228).  [PMID:19803483]
16. Ewa Kamieńska-Piotrowicz,Kamila Dziewulska,Janusz Stangret.  (2010-04-13)  An effective method for studying intermolecular interactions in binary liquids with hydrogen bonds; FTIR spectra and ab initio calculations in the N-methylformamide-methanol system..  The journal of physical chemistry. B,  114  ((17)): (5810-5818).  [PMID:20380396]
17. Xing-Guo Zhang,Hui-Xiong Dai,Masayuki Wasa,Jin-Quan Yu.  (2012-07-12)  Pd(II)-catalyzed ortho trifluoromethylation of arenes and insights into the coordination mode of acidic amide directing groups..  Journal of the American Chemical Society,  134  ((29)): (11948-11951).  [PMID:22780303]
18. A Nakazawa,I Nishii.  (2012-07-25)  Amidic and acetonic cryoprotectants improve cryopreservation of volvocine green algae..  Cryo letters,  33  ((3)): (202-213).  [PMID:22825787]
19. Rachel Crespo-Otero,Artur Mardyukov,Elsa Sanchez-Garcia,Mario Barbatti,Wolfram Sander.  (2012-10-04)  Photochemistry of N-methylformamide: matrix isolation and nonadiabatic dynamics..  Chemphyschem : a European journal of chemical physics and physical chemistry,  14  ((4)): (827-836).  [PMID:23033207]
20. P Imrat,P Suthanmapinanth,K Saikhun,S Mahasawangkul,E Sostaric,P Sombutputorn,S Jansittiwate,N Thongtip,A Pinyopummin,B Colenbrander,W V Holt,T A E Stout.  (2012-11-22)  Effect of pre-freeze semen quality, extender and cryoprotectant on the post-thaw quality of Asian elephant (Elephas maximus indicus) semen..  Cryobiology,  66  ((1)): (52-59).  [PMID:23168056]
21. Hideki Igisu,Takafumi Ezaki.  (2005-01-22)  [N-methylformamide in urine]..  Nihon rinsho. Japanese journal of clinical medicine,  62 Suppl 12  (488-490).  [PMID:15658371]
22. Shih-Min Wang,Yao-Ming Chu,Shih-Chun Candice Lung,Tung-Sheng Shih,Yue-Ching Lin,Ho-Yuan Chang.  (2007-09-15)  Combining novel strategy with kinetic approach in the determination of respective respiration and skin exposure to N,N-dimethylformamide vapor..  The Science of the total environment,  388  ((1-3)): (398-404).  [PMID:17854864]
23. Jeppe S Spicker,Søren Brunak,Klaus S Frederiksen,Henrik Toft.  (2008-01-08)  Integration of clinical chemistry, expression, and metabolite data leads to better toxicological class separation..  Toxicological sciences : an official journal of the Society of Toxicology,  102  ((2)): (444-454).  [PMID:18178960]
24. Aleksandr B Sahakyan,Aleksan G Shahkhatuni,Astghik A Shahkhatuni,Henry A Panosyan.  (2008-03-28)  Electric field effects on one-bond indirect spin-spin coupling constants and possible biomolecular perspectives..  The journal of physical chemistry. A,  112  ((16)): (3576-3586).  [PMID:18363392]
25. Merwe Albrecht,Corey A Rice,Martin A Suhm.  (2008-07-31)  Elementary peptide motifs in the gas phase: FTIR aggregation study of formamide, acetamide, N-methylformamide, and N-methylacetamide..  The journal of physical chemistry. A,  112  ((33)): (7530-7542).  [PMID:18665575]
26. Xichen Li,Wenlan Liu,Kening Sun,Yan Wang,Hongwei Tan,Guangju Chen.  (2008-10-29)  Theoretical exploration of the cooperative effect in NMF-NMF-amino acid residue hydrogen bonding system..  Physical chemistry chemical physics : PCCP,  10  ((36)): (5607-5615).  [PMID:18956096]
27. Gregory M Fahy.  (2009-06-09)  Cryoprotectant toxicity neutralization..  Cryobiology,  60  ((3 Suppl)): (S45-S53).  [PMID:19501081]
28. Walther Caminati,Juan Carlos López,Susana Blanco,Santiago Mata,Josè Luis Alonso.  (2010-07-27)  How water links to cis and trans peptidic groups: the rotational spectrum of N-methylformamide-water..  Physical chemistry chemical physics : PCCP,  12  ((35)): (10230-10234).  [PMID:20657893]
29. M Sałdyka,Z Mielke,K Mierzwicki,S Coussan,P Roubin.  (2011-07-12)  CH stretching vibration of N-methylformamide as a sensitive probe of its complexation: infrared matrix isolation and computational study..  Physical chemistry chemical physics : PCCP,  13  ((31)): (13992-14002).  [PMID:21743931]
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