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METHYL 2-BROMO-4-NITROBENZOATE, with the molecular formula C8H6BrNO4, is a yellow solid chemical compound used extensively in organic synthesis and chemical research. It is recognized for its strong nitro flavor and serves as a versatile intermediate in the production of pharmaceuticals, agrochemicals, and dyes, as well as a building block for synthesizing various other organic compounds.

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  • 100959-22-6 Structure
  • Basic information

    1. Product Name: METHYL 2-BROMO-4-NITROBENZOATE
    2. Synonyms: METHYL 2-BROMO-4-NITROBENZOATE;2-BroMo-4-nitrobenzoic acid Methyl ester;3-Bromo-4-(methoxycarbonyl)nitrobenzene;4-nitro-2-broMobenzoic acid Methyl ester;Methyl 2-bromo-4-nitrobenzoate 97%;2-Bromo-4-nitro-benzoic acid methyleste
    3. CAS NO:100959-22-6
    4. Molecular Formula: C8H6BrNO4
    5. Molecular Weight: 260.04
    6. EINECS: N/A
    7. Product Categories: blocks;Bromides;Carboxes;NitroCompounds
    8. Mol File: 100959-22-6.mol
  • Chemical Properties

    1. Melting Point: 82.0 to 86.0 °C
    2. Boiling Point: 339.199 °C at 760 mmHg
    3. Flash Point: 158.942 °C
    4. Appearance: /
    5. Density: 1.674 g/cm3
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 1.588
    8. Storage Temp.: Sealed in dry,Room Temperature
    9. Solubility: N/A
    10. CAS DataBase Reference: METHYL 2-BROMO-4-NITROBENZOATE(CAS DataBase Reference)
    11. NIST Chemistry Reference: METHYL 2-BROMO-4-NITROBENZOATE(100959-22-6)
    12. EPA Substance Registry System: METHYL 2-BROMO-4-NITROBENZOATE(100959-22-6)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 100959-22-6(Hazardous Substances Data)

100959-22-6 Usage

Uses

Used in Pharmaceutical Industry:
METHYL 2-BROMO-4-NITROBENZOATE is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and improving existing ones. Its unique chemical properties make it a valuable component in the creation of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, METHYL 2-BROMO-4-NITROBENZOATE is utilized as an intermediate in the production of agrochemicals, such as pesticides and herbicides. Its role in these applications aids in enhancing crop protection and increasing agricultural productivity.
Used in Dye Industry:
METHYL 2-BROMO-4-NITROBENZOATE is employed as a building block in the synthesis of dyes, playing a crucial role in the development of new colorants for various applications, including textiles, plastics, and printing inks.
Used in Organic Synthesis:
As a versatile reagent in organic reactions, METHYL 2-BROMO-4-NITROBENZOATE is used for the synthesis of a wide range of organic compounds. Its unique properties make it an essential component in various chemical processes, contributing to the advancement of organic chemistry.
It is important to handle METHYL 2-BROMO-4-NITROBENZOATE with care due to its toxic nature and potential to cause skin and eye irritation upon contact. Proper safety measures should be taken to minimize risks associated with its use.

Check Digit Verification of cas no

The CAS Registry Mumber 100959-22-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,0,9,5 and 9 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 100959-22:
(8*1)+(7*0)+(6*0)+(5*9)+(4*5)+(3*9)+(2*2)+(1*2)=106
106 % 10 = 6
So 100959-22-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H6BrNO4/c1-14-8(11)6-3-2-5(10(12)13)4-7(6)9/h2-4H,1H3

100959-22-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl 2-Bromo-4-Nitrobenzoate

1.2 Other means of identification

Product number -
Other names Methyl 2-BroMo-4-nitrobenzoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:100959-22-6 SDS

100959-22-6Relevant articles and documents

Synthesis of a coronene analogue containing an amide bond by Pd-mediated intramolecular C[sbnd]C bond formation of 2-halogenated 4-(alkylamino)benzoic acid cyclic trimer

Yokoyama, Akihiro,Ishii, Arisa,Ohishi, Tomoyuki,Kikkawa, Shoko,Azumaya, Isao

, (2021)

A coronene analogue containing amide linkage was synthesized from a halogenated cyclic triamide by palladium-mediated intramolecular C[sbnd]C bond formation. The cyclic triamide was formed from the condensation of 2-chloro-4-(isobutylamino)benzoic acid in

In vitro and in vivo antimalarial activity of peptidomimetic protein farnesyltransferase inhibitors with improved membrane permeability

Carrico, Dora,Ohkanda, Junko,Kendrick, Howard,Yokoyama, Kohei,Blaskovich, Michelle A.,Bucher, Cynthia J.,Buckner, Frederick S.,Van Voorhis, Wesley C.,Chakrabarti, Debopam,Croft, Simon L.,Gelb, Michael H.,Sebti, Sa?d M.,Hamilton, Andrew D.

, p. 6517 - 6526 (2004)

A series of ester derivatives of 17 with increased lipophilicity were synthesized and tested against P. falciparum in red blood cells, where the benzyl ester derivative 16 exhibited the best inhibition activity (ED 50 = 150 nM). Compound 16 sho

An Activatable Lanthanide Luminescent Probe for Time-Gated Detection of Nitroreductase in Live Bacteria

Brennecke, Benjamin,Hu, Hai-Yu,Nazaré, Marc,Wang, Qinghua,Zhang, Qingyang

supporting information, p. 8512 - 8516 (2020/04/24)

Herein we report the development of a turn-on lanthanide luminescent probe for time-gated detection of nitroreductases (NTRs) in live bacteria. The probe is activated through NTR-induced formation of the sensitizing carbostyril antenna and resulting energ

Scope and mechanism of a true organocatalytic beckmann rearrangement with a boronic acid/perfluoropinacol system under ambient conditions

Mo, Xiaobin,Morgan, Timothy D. R.,Ang, Hwee Ting,Hall, Dennis G.

, p. 5264 - 5271 (2018/04/24)

Catalytic activation of hydroxyl functionalities is of great interest for the production of pharmaceuticals and commodity chemicals. Here, 2-alkoxycarbonyl- and 2-phenoxycarbonyl-phenylboronic acid were identified as efficient catalysts for the direct and chemoselective activation of oxime N-OH bonds in the Beckmann rearrangement. This classical organic reaction provides a unique approach to prepare functionalized amide products that may be difficult to access using traditional amide coupling between carboxylic acids and amines. Using only 5 mol % of boronic acid catalyst and perfluoropinacol as an additive in a polar solvent mixture, the operationally simple protocol features mild conditions, a broad substrate scope, and a high functional group tolerance. A wide variety of diaryl, aryl-alkyl, heteroaryl-alkyl, and dialkyl oximes react under ambient conditions to afford high yields of amide products. Free alcohols, amides, carboxyesters, and many other functionalities are compatible with the reaction conditions. Investigations of the catalytic cycle revealed a novel boron-induced oxime transesterification providing an acyl oxime intermediate involved in a fully catalytic nonself-propagating Beckmann rearrangement mechanism. The acyl oxime intermediate was prepared independently and was subjected to the reaction conditions. It was found to be self-sufficient; it reacts rapidly, unimolecularly without the need for free oxime. A series of control experiments and 18O labeling studies support a true catalytic pathway involving an ionic transition structure with an active and essential role for the boronyl moiety in both steps of transesterification and rearrangement. According to 11B NMR spectroscopic studies, the additive perfluoropinacol provides a transient, electrophilic boronic ester that is thought to serve as an internal Lewis acid to activate the ortho-carboxyester and accelerate the initial, rate-limiting step of transesterification between the precatalyst and the oxime substrate.

Explicit treatment of active-site waters enhances quantum mechanical/implicit solvent scoring: Inhibition of CDK2 by new pyrazolo[1,5-a]pyrimidines

Hylsová, Michaela,Carbain, Benoit,Fanfrlík, Jind?ich,Musilová, Lenka,Haldar, Susanta,K?prülüo?lu, Cemal,Ajani, Haresh,Brahmkshatriya, Pathik S.,Jorda, Radek,Kry?tof, Vladimír,Hobza, Pavel,Echalier, Aude,Paruch, Kamil,Lep?ík, Martin

, p. 1118 - 1128 (2017/01/03)

We present comprehensive testing of solvent representation in quantum mechanics (QM)-based scoring of protein-ligand affinities. To this aim, we prepared 21 new inhibitors of cyclin-dependent kinase 2 (CDK2) with the pyrazolo[1,5-a]pyrimidine core, whose

NOVEL COMPOUNDS AS CHLORIDE CHANNEL BLOCKING AGENT

-

Paragraph 0167; 0168; 0169; 0170; 0171; 0172; 0173-0175, (2015/06/03)

Disclosed is a novel compound to function as a calcium-dependent chloride channel blocking agent.

AMPHIPATHIC AND OTHER DOUBLE-SIDED ALPHA-HELIX MIMETICS BASED ON A 1,2-DIPHENYLACETYLENE SCAFFOLD

-

Page/Page column, (2014/09/29)

Small-molecule scaffolds based on 1,2-diphenylacetylene that accurately replicate the spatial and angular projections of several side chains on both faces of an α-helix, specifically the i and i+7 side chains on one face, and the i and i+2 side chains on the other. The amphipathic α-helix mimetic can be used to disrupt disease-promoting protein-protein interactions that are mediated by α-helices.

Novel pyrrolobenzoxaboroles: Design, synthesis, and biological evaluation against Trypanosoma brucei

Wu, Puhua,Zhang, Jiong,Meng, Qingqing,Nare, Bakela,Jacobs, Robert T.,Zhou, Huchen

, p. 59 - 75 (2014/06/09)

Human African trypanosomiasis is a fatal parasitic infection caused by the protozoan Trypanosoma brucei. The development of novel antitrypanosomal agents is urgently needed. Here we report the synthesis and structure-activity relationship of a new class of benzoxaboroles as antitrypanosomal agents. These compounds showed antiparasitic IC50 values ranging from 4.02 to 0.03 μg/mL and satisfactory cytotoxicity profile. Three of the lead compounds were demonstrated to cure the parasitic infection in a murine acute infection model. The structure-activity relationship of the pyrrolobenzoxaboroles are also discussed.

Amphipathic α-helix mimetics based on a 1,2-diphenylacetylene scaffold

Jung, Kwan-Young,Vanommeslaeghe, Kenno,Lanning, Maryanna E.,Yap, Jeremy L.,Gordon, Caryn,Wilder, Paul T.,Mackerell, Alexander D.,Fletcher, Steven

supporting information, p. 3234 - 3237 (2013/07/26)

In order to mimic amphipathic α-helices, a novel scaffold based on a 1,2-diphenylacetylene was designed. NMR and computational modeling confirmed that an intramolecular hydrogen bond favors conformations of the 1,2-diphenylacetylene that allow for accurat

Monna, a potent and selective blocker for transmembrane protein with unknown function 16/anoctamin-1

Oh, Soo-Jin,Hwang, Seok Jin,Jung, Jonghoon,Yu, Kuai,Kim, Jeongyeon,Choi, Jung Yoon,Hartzell, H. Criss,Roh, Eun Joo,Justin Lee

, p. 726 - 735 (2013/11/06)

Transmembrane protein with unknown function 16/anoctamin-1 (ANO1) is a protein widely expressed in mammalian tissues, and it has the properties of the classic calcium-activated chloride channel (CaCC). This protein has been implicated in numerous major physiological functions. However, the lack of effective and selective blockers has hindered a detailed study of the physiological functions of this channel. In this study, we have developed a potent and selective blocker for endogenous ANO1 in Xenopus laevis oocytes (xANO1) using a drug screening method we previously established (Oh et al., 2008). We have synthesized a number of anthranilic acid derivatives and have determined the correlation between biological activity and the nature and position of substituents in these derived compounds. A structure-activity relationship revealed novel chemical classes of xANO1 blockers. The derivatives contain a-NO2 group on position 5 of a naphthyl group-substituted anthranilic acid, and they fully blocked xANO1 chloride currents with an IC 5050 of 0.08 μM for xANO1. Selectivity tests revealed that other chloride channels such as bestrophin-1, chloride channel protein 2, and cystic fibrosis transmembrane conductance regulator were not appreciably blocked by 10~30 μM MONNA. The potent and selective blockers for ANO1 identified here should permit pharmacological dissection of ANO1/CaCC function and serve as potential candidates for drug therapy of related diseases such as hypertension, cystic fibrosis, bronchitis, asthma, and hyperalgesia.

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