10397-30-5

Basic information

• Product Name: 4-Methyl-3-nitrobenzoyl chloride
• 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%
• CAS NO: 10397-30-5
• Molecular Formula: C₈H₆ClNO₃
• Molecular Weight: 199.59
• EINECS: 233-858-1
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 10397-30-5.mol
• Article Data: 31

Chemical Properties

• Melting Point: 20-21 °C(lit.)
• Boiling Point: 185 °C36 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.37 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0012mmHg at 25°C
• Refractive Index: n20/D 1.581(lit.)
• CAS DataBase Reference: 4-Methyl-3-nitrobenzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methyl-3-nitrobenzoyl chloride(10397-30-5)
• EPA Substance Registry System: 4-Methyl-3-nitrobenzoyl chloride(10397-30-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 10397-30-5(Hazardous Substances Data)

Usage

Description

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.

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.]

InChI:InChI=1/C8H6ClNO3/c1-5-2-3-6(8(9)11)4-7(5)10(12)13/h2-4H,1H3

Upstream product

• 96-98-0 4-methyl-3-nitrobenzoic acid 
• 31680-07-6 4-methyl-3-nitrobenzaldehyde 
• 19013-15-1 ethyl 4-methyl-3-nitro-benzoate 
• 104-85-8 para-methylbenzonitrile 
• 939-79-7 4-cyano-2-nitrotoluene 
• 99-94-5 p-Toluic acid 

Downstream Products

• 99973-25-8 4-methyl-3-nitro-benzoic acid thiazol-2-ylamide 
• 85366-72-9 4-methyl-3-nitro-benzoic acid-[2]pyridylamide 
• 59383-34-5 4-Methyl-3-nitro-benzoic acid 2-diethylamino-ethyl ester 
• 88858-54-2 3-(3-Amino-4-methylbenzoyl)-1-butylharnstoff 
• 92703-67-8 3-(3-Amino-4-methylbenzoyl)-1-cyclohexylharnstoff 
• 137998-03-9 Stearyl 4-methyl-3-nitrobenzoate 
• 1022918-44-0 6-(4-methyl-3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 1063722-75-7 4'-bromo-4-methyl-3-nitrobenzophenone 
• 40870-59-5 (4-Methyl-3-nitro-phenyl)-methanol 
• 59383-32-3 4-Methyl-3-nitrobenzoesaeure-n-nonylester 
• 59383-31-2 hexyl 4-methyl-3-nitrobenzoate 
• 59383-29-8 4-Methyl-3-nitrobenzoesaeure-n-butylester 
• 59383-12-9 4-Methyl-3-nitro-benzoic acid 2-bromo-ethyl ester 
• 59383-11-8 2-chloroethyl 3-nitro-p-toluate 

Relevant articles and documents

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

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%.

GLUCOCORTICOID RECEPTOR AGONIST AND IMMUNOCONJUGATES THEREOF

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

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

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.

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

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.