CAS: 79-15-2; N-Bromoacetamide

该化合物是一种溴化剂,广泛用于有机合成,用于选择性溴化反应.它精确地控制了电子生殖性溴化,特别是藻类,克酮和芳香化合物的溴化,同时尽量减少了侧反应.该化合物在环境条件下具有稳定性,易于处理,并且具有连贯性.其固态形式确保了准确的剂量,并且比液体溴化剂的挥发性更低. n-溴代二苯胺通常用于药品中间体,农用化学品和精细化学生产,其中选择性功能化至关重要.再剂与各种溶剂的兼容性和中度反应条件进一步增强了其在复杂的合成途径中的效用.

结构式图片

相似化合物

60-35-5 1449-72-5 600726-26-9

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

acetamide N,N-dibromoacetamide sodium acetylamide (10),16-diene-7,19-dioic acid 7,19-dimethyl esterent-13-Acetoxy-3-oxo-20-norgibberella-1(10),16-diene-7,19-dioic acid 7,19-dimethyl ester2-bromothiophene 2,5-dibromothiophen 1-phenyl-propan-1-one N-Bromosuccinimide

合成工艺路线路线简述

  • 合成目标产物 N-Bromoacetamide 主要起始原料 Acetamide
  • 60-35-5 = 79-15-2
    反应条件:1.1 Reagents: Potassium Hydroxide,Bromine Solvents: Water; 2 - 3 H,0 - 5 °C
    标题:K3Po4-Catalyzed Regiospecific Bromoamidation Of β,β-Dicyanostyrene Derivatives With N-Bromoacetamide (Nba)
    作者:Chen,Zhanguo; Li,Yanan; Zhou,Jimei; Wang,Dan; Ge,Miao
    参考文献:Chemical Research In Chinese Universities 日期:2014 卷标:30(2) 页码:266-271]

    60-35-5 = 79-15-2
    反应条件:1.1 Reagents: Potassium Hydroxide,Bromine Solvents: Water; 0 - 5 °C; 2 - 3 H,Cooled
    标题:One-Pot Synthesis Of 2-Oxazolines From Ethyl α-Cyanocinnamate Derivatives With N-Bromoacetamide
    作者:Chen,Zhanguo; Wen,Hua; Li,Wenli; Zhou,Jimei; Hu,Junli; Et Al
    参考文献:Journal Of Heterocyclic Chemistry 日期:2014 卷标:51(3) 页码:794-802]

    60-35-5 = 79-15-2 [标题:Reaction Conditions
    标题:Product Class 13: N-Heteroatom-Substituted Alkanamides
    作者:Blakemore,P. R.
    参考文献:Science Of Synthesis 日期:2005 卷标:21 页码:833-905]

    60-35-5 = 79-15-2 [标题:Reaction Conditions
    标题:Product Subclass 3: Sodium Halides And Sodium Cyanide
    作者:Krapcho,A. Paul
    参考文献:Science Of Synthesis 日期:2006 卷标:8 页码:925-1010]

    462-40-8 = 79-15-2 [标题:Reaction Conditions
    标题:Preparation Of C4-C5 Isoolefins
    参考文献:Ussr]

    60-35-5 = 79-15-2
    反应条件:1.1 Reagents: Potassium Hydroxide,Bromine Solvents: Water
    标题:N-Bromoacetamide
    作者:Oliveto,Eugene P.; Gerold,Corinne
    参考文献:Organic Syntheses 日期:1951 卷标:31 页码:17-18]

    60-35-5 = 79-15-2
    反应条件:1.1 Reagents: Potassium Hydroxide,Bromine; 2.5 H,0 - 5 °C
    标题:A Peptide Bromoiodinane Approach For Asymmetric Bromolactonization
    作者:Whitehead,Daniel C.; Fhaner,Matthew; Borhan,Babak
    参考文献:Tetrahedron Letters 日期:2011 卷标:52(18) 页码:2288-2291]

    60-35-5 = 79-15-2
    反应条件:1.1 Reagents: Bromine; 0 - 5 °C1.2 Reagents: Potassium Hydroxide; 0 - 5 °C; 2 - 3 H,0 - 5 °C1.3 Reagents: Sodium Chloride Solvents: Chloroform; Heated
    标题:K3Po4-Catalyzed Regiospecific Aminobromination Of β-Nitrostyrene Derivatives With N-Bromoacetamide As Aminobrominating Agent
    作者:Chen,Zhan-Guo; Wang,Yun; Wei,Jun-Fa; Zhao,Peng-Fei; Shi,Xian-Ying
    参考文献:Journal Of Organic Chemistry 日期:2010 卷标:75(6) 页码:2085-2088]

    60-35-5 = 79-15-2
    反应条件:1.1 Reagents: Potassium Hydroxide,Bromine Solvents: Water
    标题:Electronic Effects On The Regio- And Enantioselectivity Of The Asymmetric Aminohydroxylation Of O-Substituted 4-Hydroxy-2-Butenoates
    作者:Chuang,Chih-Yuan; Vassar,Victor C.; Ma,Zuping; Geney,Raphael; Ojima,Iwao
    参考文献:Chirality 日期:2002 卷标:14 页码:151-162]

    79-16-3 = 79-15-2 [标题:Reaction Conditions
    标题:Hydrogenation Of Phenylacetylene And Isoprene On Raney Nickel Catalysts In A Hexane-Water Emulsion
    作者:Muratova,V. I.; Kabiev,T. K.; Sokol'Skii,D. V.
    参考文献:Osn. Organ. Sintez I Neftekhimiya 日期:1987 卷标:(23) 页码:5-15]

    3695-29-2 = 79-15-2 [标题:Reaction Conditions
    标题:Procedure For The Preparation Of Tertiary Olefins
    参考文献:Federal Republic Of Germany]

    60-35-5 = 79-15-2
    反应条件:1.1 Reagents: Bromine Solvents: Water
    标题:Homolytic Displacement At Carbon Centers. Xii. Regiospecific Formation Of N-Allyl And N-Cyclopropylcarbinyl Sulfonamides And Of Allyl And Cyclopropyl Halides In The Reaction Of N-Halo Compounds With Organocobaloximes
    作者:Johnson,Michael D.; Lampman,Gary M.; Koops,Roger W.; Das Gupta,B.
    参考文献:Journal Of Organometallic Chemistry 日期:1987 卷标:326(2) 页码:281-8]

    15219-34-8 = 79-15-2 [标题:Reaction Conditions
    标题:Catalyst And Process For Dehydrating 2-Alcohols
    参考文献:European Patent Organization]

    60-35-5 + 128-08-5 = 79-15-2 + 123-56-8
    反应条件:1.1 Solvents: Acetone; 10 H,Rt
    标题:Synthesis Of 2-Oxazolines From Ethyl α-Cyanocinnamate Derivatives With Acetamide And N-Bromosuccinimide
    作者:Chen,Zhan-Guo; Xia,Wei; Wen,Hua; Wang,Dan; Li,Ya-Nan; Et Al
    参考文献:Chemical Research In Chinese Universities 日期:2013 卷标:29(4) 页码:699-705]

    60-35-5 + 128-08-5 = 79-15-2 + 123-56-8
    反应条件:1.1 Solvents: Acetone; 10 H,Rt
    标题:K3Po4-Catalyzed Regiospecific Aminobromination Of β-Nitrostyrene Derivatives With Acetamide And Nbs
    作者:Chen,Zhanguo; Zhou,Jimei; Wang,Yun; Li,Wenli
    参考文献:Huaxue Xuebao 日期:2011 卷标:69(23) 页码:2851-2858
Alkaline Earth Salt Of/the/ Methylsulfuric Acid置于溴体系中,化学反应生成 N-溴代乙酰胺
参考文献:Seliwanow,Chemische Berichte,1893,Vol. 26,P. 425
标题:Seliwanow,Chemische Berichte,1893,Vol. 26,P. 425

海关参考信息

专利信息


专利号:US-5668285-A
优先权日:1986-10-31
标 题 :Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates
发明人:RICE KENNER CRALLE; NEWMAN AMY HAUCK
权利人:US HEALTH
摘要:The invention involves a method of making key intermediates useful in the synthesis of many opiate narcotics and antagonists and agonists; and the non-opiate enantiomers thereof which have potent antitussive properties. The synthesis starts from either the natural or unnatural enantiomer of nordihydrocodeinone and produces 8, 14-dihydronorthebaine, the diketal of 7-bromonordihydrocodeinone, northebaine, norcodeinone diketal and 14-hydroxynorcodeinone intermediates without the necessity of leaving the N-nor structure. The syntheses have fewer steps than previous methods, and also have high yields.

专利号:US-9085538-B2
优先权日:2010-07-26
标题:Process for the preparation of key intermediates for the synthesis of statins or pharmaceutically acceptable salts thereof
发明人:CASAR ZDENKO; STERK DAMJAN; JUKIC MARKO
权利人:CASAR ZDENKO; STERK DAMJAN; JUKIC MARKO; LEK PHARMACEUTICALS
摘要:The invention relates to commercially viable process for the synthesis of key intermediates for the preparation of statins, in particular Rosuvastatin and Pitavastatin or respective pharmaceutically acceptable salts thereof. A new simple and short synthetic route for key intermediates is presented which benefits from the use of cheap and readily available starting materials, by which the conventionally most frequently used DIBAL-H as reducing agent can be avoided.

专利号:US-7888337-B2
优先权日:2007-08-31
标 题 :Synthesis of oseltamivir containing phosphonate congeners with anti-influenza activity
发明人:WONG CHI-HUEY; FANG JIM-MIN; SHIE JIUN-JIE; CHENG YIH-SHYUN EDMOND; JAN JIA-TSRONG
权利人:ACADEMIA SINICA
摘要:Novel phosphonate compounds are described. The compounds have activity as neuraminidase inhibitors against wild-type and H274Y mutant of H1N1 and H5N1 viruses. The present disclosure also provides an enantioselective synthetic route to known neuraminidase inhibitors oseltamivir and the anti-flu drug Tamiflu®, as well as novel phosphonate compounds, via D-xylose. Another efficient and flexible synthesis of Tamiflu and the highly potent neuraminidase inhibitor Tamiphosphor was also achieved in 11 steps and >20% overall yields from the readily available fermentation product (1S-cis)-3-bromo-3,5 -cyclohexadiene-1,2-diol. Most of the reaction intermediates were obtained as crystals without tedious purification procedures. The key transformations include an initial regio- and stereoselective bromoamidation of a bromoarene cis-dihydrodiol, as well as the final palladium-catalyzed carbonylation and phosphonylation.

专利号:US-3703530-A
优先权日:1970-08-24
标 题 :Alkyl - 2 - alkyl - 2,3 - dicarboxy-5-norbornene - 7-acetate intermediates for the total synthesis of elenolic acids and analogs thereof
发明人:KELLY ROBERT C
权利人:UPJOHN CO
摘要:A TOTAL SYNTHESIS OF ELENOLIC ACID, FORMULA XIV (R AND R2 ARE HYDROGEN, R1 AND R3 ARE METHYL) AND THE ANALOGS THEREOF, OF FORMULA XIV: 3-(R3-O-),4-(R-OOC-CH(-R2)-),5-(HCO-),6-R1-5,6-DIHYDRO- 4H-PYRAN WHEREIN R AND R3 ARE ALKYL OF 1 TO 8 CARBON ATOMS, INCLUSIVE, WHEREIN R1 IS ALKYL OF 1 TO 4 CARBON ATOMS, INCLUSIVE, AND WHEREIN R2 IS SELECTED FROM THE GROUP CONSISTING OF HYDROGEN AND ALKYL OF 1 TO 4 CARBON ATOMS, INCLUSIVE, IS CARRIED OUT BY A MULTI-STEP PROCESS STARTING FROM CYCLOPENTADIENE. COMPOUNDS OF FORMULA XIV HAVE VIRUCIDAL AND HYPOTENSIVE ACTIVITY AND CAN BE USED AS HYPOTENSIVE AGENTS IN MAMMALS (U.S. PAT. 3,033,877) OR AS VIRUCIDAL AGENTS TO DECONTAMINATE SURGICAL INSTRUMENTS, HOSPITAL WALLS, SWIMMING POOLS, OR CAN BE USED FOR NASAL WASHES IN MAMMALS.

专利号:US-11512062-B2
优先权日:2018-10-15
标 题:Process for the synthesis of piperazinyl-ethoxy-bromophenyl derivates and their application in the production of compounds containing them
发明人:BEAUREGARD LOUIS-PHILIPPE; BERTRAND MARTIAL; GIGUERE PASCALL; HARDOUIN CHRISTOPHE; SCHIAVI BRUNO
权利人:SERVIER LAB
摘要:Process for the industrial synthesis of the compound of formula (I):

专利号:EP-0496830-B1
优先权日:1989-10-16
标 题 :Total synthesis of northebaine, normorphine, noroxymorphone enantiomers and derivatives via n-nor intermediates
发明人:RICE KENNER CRALLE; NEWMAN AMY HAUCK
权利人:US HEALTH
摘要:Families of antagonist-agonists and opiate narcotics are produced from norhydrocodeinone. In a preferred embodiment, norhydrocodeinone is refluxed with sulfosalicyclic dimethylketal and delta-6-enol ether derivatives and is then converted entirely to the ether by the addition of dry tetrahydrofuran simultaneously with the removal of the thus produced ether. The ether is then reacted with methanesulfonic acid and N-bromoacetamide to form the hydrobromide salt of the 7-bromodimethylketal derivative. From this derivative, a variety of products can be derived, including the novel further intermediate 14 hydroxynorcodeinone. The present invention enables derivation using a starting material which, unlike the starting materials of prior art processes, is available in the natural (-) or synthetic (+) form. Thus, the method of the present invention provides the only known route for the synthesis of (+) forms of various derivatives and intermediates, such as (+)-7-bromo-dimethylketal nordihydrocodeinone.
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主要参考文献

[参考文献]: Matteson Dr, Et Al. Modification Of K Channel Inactivation By Papain And N-Bromoacetamide. Biophys J. 1988;53(4):641-645.
[参考文献]: Patlak J, Et Al. Effect Of N-Bromoacetamide On Single Sodium Channel Currents In Excised Membrane Patches. J Gen Physiol. 1982;79(3):333-351.
[参考文献]: Adam J Lesiak, Et Al. Ribotag Is A Flexible Tool For Measuring The Translational State Of Targeted Cells In Heterogeneous Cell Cultures. Biotechniques. 2015 Jun 1;58(6):308-17.
[参考文献]: Joshua A Harrill, Et Al. Media Formulation Influences Chemical Effects On Neuronal Growth And Morphology. In Vitro Cell Dev Biol Anim. 2015 Jun;51(6):612-29.
[参考文献]: Kyoung-Jin Jang, Et Al. Mitochondrial Function Provides Instructive Signals For Activation-Induced B-Cell Fates. Nat Commun. 2015 Apr 10:6:6750.

合成参考文献


摘要:Li, W.; Liu, X. H.; Feng, X. M., Science of Synthesis Knowledge Updates, (2021) 1, 34.
摘要:Pilgrim, B. S.; Tucker, M. J., Science of Synthesis Knowledge Updates, (2019) 1, 324.
摘要:Dagousset, G.; Masson, G., Science of Synthesis Knowledge Updates, (2015) 1, 422.
摘要:Yin, Q.; You, S.-L., Science of Synthesis Knowledge Updates, (2014) 2, 465.
摘要:Muñiz, K., Science of Synthesis: Stereoselective Synthesis, (2011) 1, 34.
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