99-55-8

Basic information

• Product Name: 2-Methyl-5-nitroaniline
• Synonyms: SCARLET G BASE;P-NITRO-P-TOLUIDINE;PNOT;TIMTEC-BB SBB007597;1-amino-2-methyl-5-nitrobenzene;2-amino-4-nitrotoluene[qr];2-methyl-5-nitroaniline[qr];2-methyl-5-nitro-benzenamin
• CAS NO: 99-55-8
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.15
• EINECS: 202-765-8
• Product Categories: Dyes and Pigments;Anilines, Aromatic Amines and Nitro Compounds
• Mol File: 99-55-8.mol
• Article Data: 32

Chemical Properties

• Melting Point: 103-106 °C(lit.)
• Boiling Point: 294.61°C (rough estimate)
• Flash Point: 153 °C
• Appearance: Ochre to yellow-orange/Crystalline Powder
• Density: 1.2333 (estimate)
• Refractive Index: 1.6276 (estimate)
• Storage Temp.: 2-8°C
• PKA: 2.34±0.10(Predicted)
• Water Solubility: <0.1 g/100 mL at 19℃
• Stability: Stable. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides, acids, chloroformates.
• BRN: 879021
• CAS DataBase Reference: 2-Methyl-5-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-5-nitroaniline(99-55-8)
• EPA Substance Registry System: 2-Methyl-5-nitroaniline(99-55-8)

Safety Data

• Hazard Codes: T,Xi
• Statements: 23/24/25-40-52/53
• Safety Statements: 36/37-45-61
• RIDADR: UN 2660 6.1/PG 3
• WGK Germany: 3
• RTECS: XU8225000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 99-55-8(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 99-55-8 differently. You can refer to the following data:
1. yellow powder
2. 5-Nitro-o-toluidine is a yellow, crystalline solid.

Uses

Different sources of media describe the Uses of 99-55-8 differently. You can refer to the following data:
1. 5-Nitro-o-toluidine is used in the synthesis of numerous dyes.
2. 2-Methyl-5-nitroaniline may be employed as analytical standard for the surfactant mediated transformations (?254nm) of 2,4-dinitrotoluene.

Preparation

2-Methyl-5-nitrobenzenamine?in concentrated sulfuric acid nitration.

Definition

ChEBI: A C-nitro compound in which the nitro compound is meta to the amino group and para to the methyl group of o-toluidine.

Air & Water Reactions

Insoluble in water. 2-Methyl-5-nitroaniline is sensitive to moisture, light, or prolonged exposure to air.

Reactivity Profile

2-Methyl-5-nitroaniline is incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides and chloroformates.

Fire Hazard

Flash point data for 2-Methyl-5-nitroaniline are not available; however, 2-Methyl-5-nitroaniline is probably combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic data. Moderately toxic by ingestion. Mutation data reported. Decomposes exothermically when heated to 150℃. When heated to decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.

Carcinogenicity

There are no data available for evaluating carcinogenic risk to humans. When 5-nitro-o-toluidine was administered in a dietary feeding study to F344 rats (50 or 100 ppm) and B6C3F1 mice (1200 or 2300 ppm) of both sexes, hepatocellular carcinomas were produced in mice but not in rats.

Shipping

UN2660 Nitrotoluidines (mono), Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Acetylate the aniline, and the acetyl derivative is crystallised to constant melting point; then hydrolyse it with 70% H2SO4 and the free base is regenerated by treatment with NH3 [Bevan et al. J Chem Soc 4284 1956]. [Beilstein 12 H 844. 12 IV 1807.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, acid chlorides; acid anhydrides; chloroformates.

InChI:InChI=1/C7H8N2O2/c1-5-2-3-6(9(10)11)4-7(5)8/h2-4H,8H2,1H3

Upstream product

• 121-14-2 2,4-dinitrotoluene 
• 95-80-7 4-methylbenzene-1,3-diamine 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 7745-93-9 2-bromo-4-nitrotoluene 
• 7745-92-8 2-iodo-1-methyl-4-nitrobenzene 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 2464-33-7 N-(2-methylphenyl)phthalimide 
• 7664-41-7 ammonia 
• 36192-16-2 N'-(2-methyl-5-nitrophenyl)-N,N-dimethylformamidine 
• 95-53-4 o-toluidine 
• 136833-45-9 2-nitro-4-amino-5-methylobenzoic acid 

Downstream Products

• 21460-74-2 2,2'-(5-Nitro-o-tolylimino)diethanol 
• 33238-32-3 2-(2-methyl-5-nitrophenyl)isoindoline-1,3-dione 
• 2879-79-0 N-(2-methyl-5-nitrophenyl)acetamide 
• 56288-98-3 N-benzyl-2-methyl-5-nitro-aniline 
• 854732-80-2 1-(2-methyl-5-nitro-anilino)-cyclopentanecarbonitrile 
• 121-77-7 benzenesulfonic acid-(2-methyl-5-nitro-anilide) 
• 19871-37-5 4-methyl-N-(2-methyl-5-nitrophenyl)benzenesulfonamide 
• 13471-68-6 2-methyl-5-nitrophenyl isocyanate 
• 96616-16-9 N,N'-bis(2-methyl-5-nitrophenyl)urea 
• 86317-36-4 2-isothiocyanato-1-methyl-4-nitro-benzene 
• 4836-84-4 (2-methyl-5-nitro-phenyl)-carbamic acid-(4-chloro-but-2-ynyl ester) 
• 1627-61-8 3-methyl-isoxazole-4,5-dione 4-[(2-methyl-5-nitro-phenyl)-hydrazone] 
• 16939-25-6 3-Nitro-benzolsulfon-N-(5-nitro-2-tolyl)-amid 
• 99871-35-9 Methandisulfonsaeure-bis-(5-nitro-2-methyl-anilid) 

Relevant articles and documents

Synthesis, spectroscopic characterization, structural studies, thermal analysis and molecular docking of N-(2-methyl-5-nitrophenyl)-4-(pyridin-2-yl)pyrimidin-2-amine, a precursor for drug design against chronic myeloid leukemia

The synthesis, crystal structure and spectroscopic and electronic properties of N-(2-methyl-5-nitrophenyl)-4-(pyridin-2-yl)pyrimidin-2-amine (NPPA), C16H13-N5O2, a potential template for drug design against chronic myelogenous leukemia (CML), is reported. The design and construction of the target molecule were carried out starting from the guanidinium nitrate salt (previously synthesized) and the corresponding enaminone. X-ray diffraction analysis and a study of the Hirshfeld surfaces revealed important interactions between the nitro-group O atoms and the H atoms of the pyridine and pyrimidine rings. A crystalline ordering in layers, by the stacking of rings through interactions of the π-π type, was observed and confirmed by a study of the shape-index surfaces and dispersion energy calculations. Quantitative electrostatic potential studies revealed the most positive value of the molecule on regions close to the N-H groups (34.8 kcal mol-1); nevertheless, steric impediments and the planarity of the molecule do not allow the formation of hydrogen bonds from this group. This interaction is however activated when the molecule takes on a new extended conformation in the active pocket of the enzyme kinase (PDB ID 2hyy), interacting with protein residues that are fundamental in the inhibition process of CML. The most negative values of the molecule are seen in regions close to the nitro group (-35.4 and -34.0 kcal mol-1). A molecular docking study revealed an energy affinity of ΔG = -10.3 kcal mol-1for NPPA which, despite not having a more negative value than the control molecule (Imatinib; ΔG = -12.8 kcal mol-1), shows great potential to be used as a template for new drugs against CML.

A polyamine dendritic polymer-copper complex: A reusable catalyst for the additive-free amination of aryl bromides, and iodides

A porphyrin-initiated amine-functionalized polyepichlorohydrin dendritic polymer (PPECH-Amine) was effectively synthesized, and its water-soluble copper complex (PPECH-Amine-Cu) was developed by treating it with copper acetate. PPECH-Amine and PPECH-Amine-Cu were characterised by different spectroscopic and microscopic techniques. PPECH-Amine-Cu was identified as a reusable catalyst for the amination of bromo- and iodo-benzene derivatives in aqueous media. Due to the presence of residual amino groups in the PPECH-Amine-Cu catalyst, the protocol does not need any additional base additive, as ammonia itself acts as a base and a coupling partner. Due to the good water-soluble nature of this catalyst, it can be easily separated and reused up to six reaction cycles without any loss in its activity.

RAF-DEGRADING CONJUGATE COMPOUNDS

The present disclosure provides, inter alia, RAF-Degrading Conjugate Compounds that are useful in the treatment of cancer and other RAF related diseases. Also provided are, pharmaceutical compositions, methods of treatment, and kits comprising a RAF- Degrading Conjugate Compound.