4920-77-8

Basic information

• Product Name: 3-Methyl-2-nitrophenol
• Synonyms: 3-Methyl-2-nitrophenole;m-Cresol, 2-nitro-;Phenol, 3-methyl-2-nitro-;3-HYDROXY-2-NITROTOLUENE;3-METHYL-2-NITROPHENOL;2-HYDROXY-6-METHYL-NITROBENZENE;2-NITRO-M-CRESOL;2-NITRO-3-HYDROXYTOLUENE
• CAS NO: 4920-77-8
• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 153.14
• EINECS: 225-546-9
• Product Categories: Aromatic Phenols;Phenoles and thiophenoles;Aromatics Compounds;Aromatics
• Mol File: 4920-77-8.mol

Chemical Properties

• Melting Point: 35-39 °C(lit.)
• Boiling Point: 106-108 °C9.5 mm Hg(lit.)
• Flash Point: 225 °F
• Appearance: Yellow solid
• Density: 1.2744 (estimate)
• Vapor Pressure: 0.043mmHg at 25°C
• Refractive Index: 1.5744 (estimate)
• Storage Temp.: 0-10°C
• Solubility: Chloroform (Slightly), Dichloromethane, Methanol (Slightly)
• PKA: 7.00±0.10(Predicted)
• Stability: Volatile
• BRN: 2047479
• CAS DataBase Reference: 3-Methyl-2-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-2-nitrophenol(4920-77-8)
• EPA Substance Registry System: 3-Methyl-2-nitrophenol(4920-77-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37-37/39-36
• RIDADR: UN 2446 6.1/PG 3
• WGK Germany: 3
• F: 10
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 4920-77-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Methyl-2-nitrophenol is used as an antitumor agent for its potential in cancer treatment. It has demonstrated effectiveness against various types of cancer, making it a valuable compound in the development of novel therapeutic strategies.
Used in Environmental Research:
3-Methyl-2-nitrophenol is utilized in the investigation of nitrous acid (HONO) formation in the gas phase. This research is conducted using a flow tube photoreactor upon irradiation of ortho-nitrophenols, contributing to the understanding of atmospheric chemistry and pollution control.

InChI:InChI=1/C7H7NO3/c1-5-3-2-4-6(9)7(5)8(10)11/h2-4,9H,1H3/p-1

Upstream product

• 858853-65-3 5-hydroxy-6-nitro-toluene-2,4-disulfonyl chloride 
• 861304-52-1 5-methoxy-6-nitro-toluene-2,4-disulfonyl chloride 
• 108-39-4 3-methyl-phenol 
• 21889-89-4 2,3-epoxy-3-methylcyclohexanone 
• 5345-42-6 1-methoxy-3-methyl-2-nitro-benzene 
• 7664-93-9 sulfuric acid 
• 7446-11-9 sulfur trioxide 
• 7697-37-2 nitric acid 
• 71-43-2 benzene 
• 7732-18-5 water 
• 64-19-7 acetic acid 
• 63815-25-8 3-methylbenzene diazonium 
• 108-44-1 1-amino-3-methylbenzene 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 2835-97-4 2-amino-3-methylphenol 
• 5345-39-1 acetic acid-(3-methyl-2-nitro-phenyl ester) 
• 5345-42-6 1-methoxy-3-methyl-2-nitro-benzene 
• 127396-65-0 3-methyl-2-nitro-4,6-bis(pyrrolidin-1'-ylmethyl)phenol 
• 149353-18-4 3-<3-(5-methyl-4-phenyl-1H-imidazol-1-yl)propoxy>-2-nitrotoluene 
• 700-38-9 2-nitro-5-methylphenol 
• 141816-23-1 3-(3-chloropropoxy)-2-nitrotoluene 
• 67823-49-8 2-(3-Methyl-2-nitro-phenoxymethyl)-oxirane 
• 1817-66-9 3-methyl-2,4-dinitrophenol 
• 1027543-79-8 3-(3-Methyl-2-nitro-phenoxy)-propionic acid 
• 222625-18-5 dimethyl 2-methyl-2-(3-methyl-2-nitrophenoxy)malonate 
• 488-17-5 3-methylbenzene-1,2-diol 
• 848589-66-2 1-(3-bromopropoxy)-3-methyl-2-nitrobenzene 
• 78258-80-7 4-methyl-3H-benzooxazol-2-one 

Relevant articles and documents

Microwave assisted synthesis of nitro phenols from the reaction of phenols with urea nitrate under acid-free conditions

Urea nitrate was found to be an inexpensive, acid-free, and safe nitrating agent that provides mononitration of phenols and substituted phenols in excellent yields with exclusive ortho-selectivity under microwave irradiation. Microwave assisted reactions reduced the reaction times substantially and enhanced the product yields from good to excellent within shorter reaction times.

Cyclodextrin-based artificial oxidases with high rate accelerations and selectivity

Three cyclodextrin derivatives with one to four 2-O-formylmethyl groups attached to the secondary rim were prepared and investigated as catalysts for the oxidation of aminophenols in buffered dilute hydrogen peroxide. The derivatives were found to be Michaelis-Menten catalysts and to give rate accelerations of up to 20,000 for the oxidation of 2-aminophenol to 2-amino-phenoxazin-3-one, and 12,000 for the oxidation of 2-amino-p-cresol to 2-nitro-p-cresol. While a range of differently substituted substrates was oxidized the success of the reaction was highly dependent on the substituent pattern. The ability of one of the new artificial enzymes to oxidize selectively one aminophenol from a mixture of two was investigated giving substrate selectivities of up to 16:1.

Design, synthesis and anticancer activity evaluation of diazepinomicin derivatives

A series of diazepinomicin derivatives were synthesized and evaluated in vitro for their growth inhibitory activity against the human carcinoma cell lines. The results indicated the anticancer selectivity of this kind of compounds. Based on the results, preliminary structure-activity relationships were discussed.

Non-steroidal dissociated glucocorticoid agonists: Indoles as A-ring mimetics and function-regulating pharmacophores

We report a SAR of non-steroidal glucocorticoid mimetics that utilize indoles as A-ring mimetics. Detailed SAR is discussed with a focus on improving PR and MR selectivity, GR agonism, and in vitro dissociation profile. SAR analysis led to compound (R)-33 which showed high PR and MR selectivity, potent agonist activity, and reduced transactivation activity in the MMTV and aromatase assays. The compound is equipotent to prednisolone in the LPS-TNF model of inflammation. In mouse CIA, at 30 mg/kg compound (R)-33 inhibited disease progression with an efficacy similar to the 3 mg/kg dose of prednisolone.

Gas-phase reaction of hydroxyl radicals with m-, o- and p-cresol

The gas-phase reaction of oxygenated aromatic compounds m-cresol,o-cresol. and p-cresol with hydroxyl radicals has been studied by GC-MS. Experiments have been performed in a large-volume photoreactor (8000 L) at 294 ± 2 K and atmospheric pressure. The relative kinetic method was used to determine the rate constants for these reactions, with 1,3,5-trimethylbenzene as a reference compound. The rate constants obtained are kOH(m-cresol) = (5.88 ± 0.92) × 10-11 cm3 molecule-1 s-1, kOH(o-cresol) = (4.32 ± 0.52) × 10 -11 cm3 molecule-1 s-1, and k OH(p-cresol) = (4.96 ± 0.75) × 10-11 cm 3 molecule-1 s-1. The degradation products observed and their respective molar yields were methyl-1,4-benzoquinone 12.4 ± 1.2%, 5-methyl-2-nitrophenol 1.5 ± 0.3%, and 3-methyl-2-nitrophenol 1.4 ± 0.3% from m-cresol, methyl-1,4-benzoquinone 5.6 ± 0.9%, and 6-methyl-2-nitrophenol 4.7 ± 0.8% from o-cresol. and 4-methyl-2-nitrophenol 17.2 ± 2.5% from p-cresol. This kinetic and product data are compared with the literature, and the reaction mechanisms are discussed. Our results are in accordance with the previous studies (Atkinson, J Phys Chem Ref Data 1989, Monograph (1), 1-246; Atkinson and Aschmann. Int J Chem Kinet 1990, 22, 59-67; Atkinson et al., Environ Sci Technol 1992, 26, 1397-1403; Atkinson et al., J Phys Chem 1978, 82, 2759-2805; Olariu et al., Atoms Environ 2002, 36, 3685-3697; Semadeni et al., Int J Chem Kinet 1995, 27, 287-304) and confirm the methyl-1,4-benzoquinone yields determined by a different experimental technique (long-path Fourier transform infrared FT-IR (Olariu et al., 2002)).

Nitration of phenolic compounds by metal-modified montmorillonite KSF

The nitration of phenolic compounds with 60% nitric acid (1.2 equiv) has been carried out in the presence of metal-modified montmorillonite KSF, prepared from different metals (V, Mo, W; Sc, La, Yb, Eu, In, Bi, Ti, Zr, Hf) and KSF or nitric acid treated HKSF, as catalysts. These catalysts showed good stabilities and high catalytic activities in nitration process. In addition, these catalysts can be recovered easily and reused for many times in nitration. This process is an eco-safer and environment-benign way for clean synthesis of nitrated phenolic compounds.

Nitrophenol derivatives oxidized by cerium(IV) ammonium nitrate (CAN) and their cytotoxicity

Oxidation of a series of phenols with cerium(IV) ammonium nitrate (CAN) in acetonitrile undermild conditions yields the mixture of corresponding nitrophenols. In the cases of methylphenols and hydroxy-carboxylic acids, the steric effect may reduce the nitration reaction. Compounds 3 a and 4b showed selective activities to Hep 3B and Hep G2 cancer cell lines, respectively. Compound 2c showed selective activities to Hep G2 and MDA-MB-231 cancer cell lines. Further more, com pound 10b showed selective activities to Hep G2, Hep 3B, MCF-7 and MDA-MB-231 cancer cell lines.

Supramolecular oxidation of anilines using hydrogen peroxide as stoichiometric oxidant

6A,6D-Di-O-(propan-2-on-1,3-diyl) α-cyclodextrin-6A,6D-dicarboxylate (2α) and 6A,6D-di-O-(propan-2-on-1,3-diyl) β-cyclodextrin-6A,6D-dicarboxylate (2β) were found to catalyze the oxidation of aromatic amines in the presence of hydrogen peroxide. The products were the corresponding nitro compounds or in some cases azo-, azoxy-, or other dimerization products. The catalysis was found to follow enzyme kinetics giving a rate increase (kcat/kuncat) of up to 1100 in the best case. Copyright

Enantioselective synthesis of the aminoimidazole segment of dragmacidin D

A facile enantioselective synthesis of the 2-aminoimidazole side-chain of dragmacidin D has been developed, which involved the regio- and stereoselective opening of the chiral epoxide 9 by a diindolylcuprate reagent, followed by further steps to give 5-substituted N-(1H-imidazol-2-yl)acetamide 2.

Regioselectivity of the nitration of phenol by acetyl nitrate adsorbed on silica gel

The reaction of phenol with acetyl nitrate in chloroform gives nitrophenol with an ortho/para ratio of 1.8. This ratio increase to 13.3 when the reaction was carried out with acetyl nitrate pre-adsorbed on dry silica gel. Silica may be acting as a template to bring phenol close to acetyl nitrate by hydrogen bonds forming a ternary complex, which undergoes a six- center rearrangement to o-nitrophenol. The formation of this ternary complex is evaluated by ab initio molecular orbital calculation.