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4-Methyl-3-nitrobenzoyl chloride is a benzoyl chloride derivative, which is synthesized from 4-methyl-3-nitrobenzoic acid. It is an organic compound with a molecular formula of C8H6ClNO4 and a molecular weight of 201.59 g/mol. 4-Methyl-3-nitrobenzoyl chloride is characterized by the presence of a methyl group at the 4-position and a nitro group at the 3-position on the benzene ring, with a carbonyl chloride group attached to the carbonyl carbon.

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  • 10397-30-5 Structure
  • Basic information

    1. Product Name: 4-Methyl-3-nitrobenzoyl chloride
    2. Synonyms: 3-NITRO-P-TOLUOYL CHLORIDE;3-NITRO-P-TOLUYL CHLORIDE;3-NITRO-4-METHYLBENZOYLCHLORIDE;4-METHYL-3-NITROBENZOYL CHLORIDE;TIMTEC-BB SBB007967;Benzoyl chloride, 4-methyl-3-nitro-;4-METHYL-3-NITROBENZOYL CHLORIDE / 3-NITRO-P-TOLUYL CHLORIDE;4-METHYL-3-NITROBENZOYL CHLORIDE 99%
    3. CAS NO:10397-30-5
    4. Molecular Formula: C8H6ClNO3
    5. Molecular Weight: 199.59
    6. EINECS: 233-858-1
    7. Product Categories: Intermediates of Dyes and Pigments
    8. Mol File: 10397-30-5.mol
  • Chemical Properties

    1. Melting Point: 20-21 °C(lit.)
    2. Boiling Point: 185 °C36 mm Hg(lit.)
    3. Flash Point: >230 °F
    4. Appearance: /
    5. Density: 1.37 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.0012mmHg at 25°C
    7. Refractive Index: n20/D 1.581(lit.)
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: 4-Methyl-3-nitrobenzoyl chloride(CAS DataBase Reference)
    11. NIST Chemistry Reference: 4-Methyl-3-nitrobenzoyl chloride(10397-30-5)
    12. EPA Substance Registry System: 4-Methyl-3-nitrobenzoyl chloride(10397-30-5)
  • Safety Data

    1. Hazard Codes: C
    2. Statements: 34
    3. Safety Statements: 26-27-36/37/39-45
    4. RIDADR: UN 3265 8/PG 2
    5. WGK Germany: 3
    6. RTECS:
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 10397-30-5(Hazardous Substances Data)

10397-30-5 Usage

Uses

Used in Pharmaceutical Industry:
4-Methyl-3-nitrobenzoyl chloride is used as a key intermediate in the synthesis of various pharmaceutical compounds. It plays a crucial role in the synthesis of 4-amino-1,5-naphthalenedisulphonate acid monosodium salt, which is an intermediate employed in the synthesis of modified suramin molecules. Suramin is an antiparasitic drug used to treat trypanosomiasis and onchocerciasis.
Used in Organic Synthesis:
4-Methyl-3-nitrobenzoyl chloride is used as a reagent in the synthesis of various organic compounds, including benzophenone derivatives, substituted 3-amino-4-methyl-N-phenylbenzamides, and retroamides. Its versatility as a reagent makes it valuable in the development of new chemical entities and the modification of existing ones.
Used in Research and Development:
4-Methyl-3-nitrobenzoyl chloride is also used in research and development for the exploration of new chemical reactions and the synthesis of novel compounds. Its unique structure and reactivity make it a valuable tool for chemists working in various fields, such as medicinal chemistry, materials science, and synthetic organic chemistry.

Purification Methods

Recrystallise the acid from EtOH. The S-benzylisothiuronium salt has m 167-168o (EtOH). The acid chloride [10397-30-5] has m 20-21o, b 185o/36mm, and the methyl ester [7356-11-8] crystallises as pale yellow needles from MeOH with m 51o. [Beilstein 9 H 502, 9 II 334, 9 III 2359.]

Check Digit Verification of cas no

The CAS Registry Mumber 10397-30-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,3,9 and 7 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 10397-30:
(7*1)+(6*0)+(5*3)+(4*9)+(3*7)+(2*3)+(1*0)=85
85 % 10 = 5
So 10397-30-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H6ClNO3/c1-5-2-3-6(8(9)11)4-7(5)10(12)13/h2-4H,1H3

10397-30-5 Well-known Company Product Price

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  • Aldrich

  • (428949)  4-Methyl-3-nitrobenzoylchloride  99%

  • 10397-30-5

  • 428949-10ML

  • 555.75CNY

  • Detail
  • Aldrich

  • (428949)  4-Methyl-3-nitrobenzoylchloride  99%

  • 10397-30-5

  • 428949-50ML

  • 1,857.96CNY

  • Detail

10397-30-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Methyl-3-nitrobenzoyl chloride

1.2 Other means of identification

Product number -
Other names 3-nitro-4-methylbenzoyl chloride

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:10397-30-5 SDS

10397-30-5Relevant articles and documents

Synthesis, functionalisation and post-synthetic modification of bismuth metal-organic frameworks

K?ppen,Beyer,Wuttke,Lüning,Stock

, p. 8658 - 8663 (2017)

Two new bismuth metal-organic frameworks (Bi-MOFs) were discovered using high throughput experiments employing bismuth(iii) nitrate pentahydrate and triazine-2,4,6-triyl-tribenzoic acid (H3TATB). The reaction was carried out for long reaction times (~5 d) in a water/DMF-mixture and resulted in the formation of [Bi2(O)(OH)(TATB)]·H2O (denoted as CAU-35). By switching to short reaction times and a methanol/DMF-mixture as the solvent, an analogue of CAU-7-BTB with the composition [Bi(TATB)]·DMF·6H2O (denoted as CAU-7-TATB) was obtained. The use of the amino-functionalised H3TATB linker (H3TATB-NH2) resulted in the formation of a functionalised porous Bi-MOF with the composition [Bi(TATB-NH2)]·5H2O·0.5DMF (CAU-7-TATB-NH2). The structures of CAU-35 and CAU-7-TATB were successfully solved and refined from the PXRD data. CAU-7-TATB-NH2 was post-synthetically modified using anhydrides (acetic anhydride and valeric anhydride), cyclic anhydrides (succinic anhydride and phthalic anhydride), and 1,3-propane sultone. The degree of conversion ranged from 33% to 79%.

Design and synthesis of antimicrobial active new molecular entities of N-substituted pipradol derivatives

Sri Ramudu,Ramachandran,Venkat Rao,Murali Krishna,Satya Narayana,Reddy, Kallam Naveen

, p. 2113 - 2115 (2017)

Synthesis of antimicrobial 4-(hydroxyldiphenyl methyl)piperidin-1-yl)(substituted phenyl)methanone derivatives by using conventional chemical reactions to produces feasible and entirely new chemical entities (NCE’S) which were having a great potential microbial activities equivalent to fexofenidine used as a biological standard. This invention may help full for derive more potential pipradol molecules with peptide bond linkage.

GLUCOCORTICOID RECEPTOR AGONIST AND IMMUNOCONJUGATES THEREOF

-

Paragraph 0117-0119, (2021/08/20)

Provided herein are glucocorticoid receptor agonist immunoconjugates, glucocorticoid receptor agonists, pharmaceutical compositiosn including the same, and methods of using the same.

Discovery of potent Pan-Raf inhibitors with increased solubility to overcome drug resistance

Wang, Lu,Zhang, Yanmin,Zhang, Qing,Zhu, Gaoyuan,Zhang, Zhimin,Duan, Chunqi,Lu, Tao,Tang, Weifang

supporting information, p. 243 - 255 (2018/12/11)

Despite various applications of kinase inhibitors in oncology and inflammatory diseases, the emergence of resistance still remains the major barrier to achieve long-term remission in cancer treatment. With the aim of overcoming the resistance induced by type IIB BRaf V600E selective inhibitor vemurafenib, and further ameliorating the antiproliferative activity, a novel type IIA Pan-Raf inhibitors Ia–Io based on pyrrolo[2,3-d] pyrimidine scaffold were designed and evaluated in this work. Herein, we tried to improve the cellular potency of the target compounds by increasing their solubility. Among them, Il, with the solubility of 0.107 mg/mL, demonstrated favorable cellular activity against vemurafenib-resistant carcinoma cells including BRafWT phenotypic melanoma SK-MEL-2 and BRafV600E phenotypic colorectal cancer HT-29 cell lines. Based on the well solubility, Il exhibited good metabolic stability compared to sorafenib and showed favorable pharmacokinetic profiles in rats. As for the biological mechanism research, Il had the similar P-ERK kinase inhibitory activity in A375 and SK-Mel-2 cells as our previously lead P-2. Il may become a good candidate compound to overcome the resistance associated with vemurafenib.

Design, synthesis and evaluation of derivatives based on pyrimidine scaffold as potent Pan-Raf inhibitors to overcome resistance

Wang, Lu,Zhang, Qing,Zhu, Gaoyuan,Zhang, Zhimin,Zhi, Yanle,Zhang, Li,Mao, Tianxiao,Zhou, Xiang,Chen, Yadong,Lu, Tao,Tang, Weifang

supporting information, p. 86 - 106 (2017/03/02)

Simutaneous targeting all Raf isoforms offers the prospect of enhanced efficacy as well as reduced potential for resistance. Described herein is the discovery and characterization of a series of pyrimidine scaffold with DFG-out conformation as potent Pan-Raf inhibitors. Among them, I-41 with excellent Pan-Raf potency demonstrates inhibitory activity against BRafWTphenotypic melanoma and BRafV600Ephenotypic colon cells. The western blot results for the Erk inhibition in human melanoma SK-Mel-2?cell lines showed I-41 inhibited the proliferation of SK-Mel-2?cell lines without paradoxical activation of Erk, which supported I-41 may become a good candidate compound to overcome the resistance of melanoma against the current BRafV600Einhibitor therapy. I-41 also have a favorable pharmacokinetic profile in rat. Synthesis, SAR, lead selection, and evaluation of the key compounds studies are described.

Facile Synthesis of N-(Benzyl-1H-1,2,3-Triazol-5-yl) Methyl)-4-(6-Methoxybenzo [d] Thiazol-2-yl)-2-Nitrobenzamides via Click Chemistry

Yarlagadda, Bharath,Devunuri, Nagaraj,Mandava, V. Basaveswara Rao

, p. 864 - 870 (2017/03/27)

A series of novel N-((l-benzyl-lH-l,2,3-triazol-5-yl) methyl)-4-(6-methoxy benzo[d]thiazol-2-yl)-2-nitrobenzamide derivatives were prepared from 4-(6-methoxybenzo[d]thiazol-2-yl)-2-nitro-N-(prop-2-ynyl) benzamide with benzyl azides by using click reaction (copper-catalyzed Huisgen 1,3-dipolar cycloaddition reaction) in the presence of CuSO4.5H2O and sodium ascaorbate. All the newly synthesized compounds were evaluated further in vitro antimicrobial activity against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtillis), Gram-negative bacteria (Echerichia coli and Pseudomonas aeuroginosa), and fungi (Aspergillus niger and Aspergillusfumigatus) strains. The new compounds were characterized based on spectroscopic evidence. Among them compounds 10a, 10h, and 10i were showed promising activity when compared with standard drugs Ciprofloxacin and Miconazole.

Rational design, synthesis, and biological evaluation of Pan-Raf inhibitors to overcome resistance

Wang, Lu,Zhu, Gaoyuan,Zhang, Qing,Duan, Chunqi,Zhang, Yanmin,Zhang, Zhimin,Zhou, Yujun,Lu, Tao,Tang, Weifang

supporting information, p. 3455 - 3465 (2017/04/26)

Selective BRafV600E inhibitors with DFG-in conformation have been proven effective against a subset of melanoma. However, representative inhibitor vemurafenib rapidly acquires resistance in the BRafWT cells through a CRaf or BRafWT dependent manner. Simultaneous targeting of all subtypes of Raf proteins offers the prospect of enhanced efficacy as well as reduced potential for acquired resistance. Herein, we describe the design and characterization of a series of compounds I-01-I-22, based on a pyrimidine scaffold with DFG-out conformation as Pan-Raf inhibitors. Among them, I-15 binds to all Raf protomers with IC50 values of 12.6 nM (BRafV600E), 30.1 nM (ARaf), 19.7 nM (BRafWT) and 17.5 nM (CRaf) and demonstrates cellular activity against BRafWT phenotypic melanoma and BRafV600E phenotypic colorectal cancer cells. The western blot results for the P-Erk inhibition in human melanoma SK-Mel-2 cell line showed that I-15 inhibited the proliferation of the SK-Mel-2 cell line at concentrations as low as 400 nM, without paradoxical activation of Erk as vemurafenib, which supported that I-15 may become a good candidate compound to overcome the resistance of melanoma induced by vemurafenib. I-15 also has a favorable pharmacokinetic profile in rats. Rational design, synthesis, SAR, lead selection and evaluation of the key compounds studied are described.

Design, Synthesis, and Biological Evaluation of Novel Type I1/2 p38α MAP Kinase Inhibitors with Excellent Selectivity, High Potency, and Prolonged Target Residence Time by Interfering with the R-Spine

Walter, Niklas M.,Wentsch, Heike K.,Bührmann, Mike,Bauer, Silke M.,D?ring, Eva,Mayer-Wrangowski, Svenja,Sievers-Engler, Adrian,Willemsen-Seegers, Nicole,Zaman, Guido,Buijsman, Rogier,L?mmerhofer, Michael,Rauh, Daniel,Laufer, Stefan A.

supporting information, p. 8027 - 8054 (2017/10/18)

We recently reported 1a (skepinone-L) as a type I p38α MAP kinase inhibitor with high potency and excellent selectivity in vitro and in vivo. However, as a type I inhibitor, it is entirely ATP-competitive and shows just a moderate residence time. Thus, the scope was to develop a new class of advanced compounds maintaining the structural binding features of skepinone-L scaffold like inducing a glycine flip at the hinge region and occupying both hydrophobic regions I and II. Extending this scaffold with suitable residues resulted in an interference with the kinase's R-Spine. By synthesizing 69 compounds, we could significantly prolong the target residence time with one example to 3663 s, along with an excellent selectivity score of 0.006 and an outstanding potency of 1.0 nM. This new binding mode was validated by cocrystallization, showing all binding interactions typifying type I1/2 binding. Moreover, microsomal studies showed convenient metabolic stability of the most potent, herein reported representatives.

Potent Pan-Raf and Receptor Tyrosine Kinase Inhibitors Based on a Cyclopropyl Formamide Fragment Overcome Resistance

Zhang, Yanmin,Wang, Lu,Zhang, Qing,Zhu, Gaoyuan,Zhang, Zhimin,Zhou, Xiang,Chen, Yadong,Lu, Tao,Tang, Weifang

, p. 1439 - 1452 (2017/06/30)

While selective BRafV600E inhibitors have been proven effective clinically, acquired resistance rapidly develops through reactivation of the mitogen-activated protein kinase (MAPK) pathway. Simultaneous targeting of multiple nodes in the pathway offers the prospect of enhanced efficacy as well as reduced potential for acquired resistance. Replacement pyridine group of Y-1 by a cyclopropyl formamide group afforded I-01 as a novel multitargeted kinase inhibitor template. I-01 displayed enzyme potency against Pan-Raf and receptor tyrosine kinases (RTKs). Based on the binding mode of I-01, analogues I-02-I-18 were designed and synthesized. The most promising compound I-16 potently inhibits all subtypes of Rafs with IC50 values of 3.49 (BRafV600E), 8.86 (ARaf), 5.78 (BRafWT), and 1.65 nM (CRaf), respectively. I-16 not only exhibit comparable antiproliferative activities with positive control compounds against HepG2, SW579, MV4-11, and COLO205 cell lines, but also suppress the proliferation of melanoma SK-MEL-2 harboring overexpressed BRafWT with IC50 values of 0.93 μM. The Western blot results for the ERK inhibition in human melanoma SK-MEL-2 cell lines show that I-16 inhibits the proliferation of SK-MEL-2 cell lines without paradoxical activation of ERK, which support the hypothesis that the inhibition of Pan-Raf and RTKs might be a tractable strategy to overcome the resistance of melanoma induced by the therapy with the current selective BRafV600E inhibitors.

Piperlongumine derived cyclic sulfonamides (sultams): Synthesis and in?vitro exploration for therapeutic potential against HeLa cancer cell lines

Lad, Nitin P.,Kulkarni, Sarang,Sharma, Rajiv,Mascarenhas, Malcolm,Kulkarni, Mahesh R.,Pandit, Shivaji S.

, p. 870 - 878 (2016/12/18)

A novel modification of piperlongumine is designed, bearing a cyclic sulphonamide (sultam) and its synthesis is described. For the first time herein we report the synthesis and biological evaluation of the natural product derived cyclic sulfonamides using Grubbs second generation catalyst (Grubbs II) via ring closing metathesis approach. Synthesis of a series of piperlongumine derived sultams is done in a moderate to good yield using Wittig reaction, Ring-Closing Metathesis (RCM) and, amide synthesis by using mixed anhydride, approach. All synthesized compounds were evaluated for anticancer activity and some demonstrated dose dependent reduction in HeLa cell growth. Of these 7, 10 and 14 significantly reduced the cell growth. Consequently their calculated GI50values were found to be 0.1 or 0.1?μM.

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