31438-22-9

Basic information

• Product Name: 9H-Carbazole, 1-nitro-
• Synonyms: 9H-Carbazole, 1-nitro-
• CAS NO: 31438-22-9
• Molecular Formula: C₁₂H₈N₂O₂
• Molecular Weight: 212.2
• EINECS: 200-258-5
• Mol File: 31438-22-9.mol

Chemical Properties

• Melting Point: 195℃ (ethanol )
• Boiling Point: 448.6°Cat760mmHg
• Flash Point: 225.1°C
• Appearance: /
• Density: 1.435±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 8.12E-08mmHg at 25°C
• Refractive Index: 1.795
• Storage Temp.: 2-8°C(protect from light)
• PKA: 14.66±0.30(Predicted)
• CAS DataBase Reference: 9H-Carbazole, 1-nitro-(CAS DataBase Reference)
• NIST Chemistry Reference: 9H-Carbazole, 1-nitro-(31438-22-9)
• EPA Substance Registry System: 9H-Carbazole, 1-nitro-(31438-22-9)

Safety Data

• Hazardous Substances Data: 31438-22-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
9H-Carbazole, 1-nitrois used as an intermediate in the synthesis of pharmaceuticals for its unique chemical properties and structure. It plays a crucial role in the development of new drugs and medicinal compounds.
Used in Agrochemical Industry:
9H-Carbazole, 1-nitrois also used as an intermediate in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural chemicals.
Used in Organic Chemistry Research:
Due to its unique chemical properties and structure, 9H-Carbazole, 1-nitrois used in organic chemistry research to explore new reactions and syntheses, potentially leading to the discovery of novel compounds and materials.
Used in Material Science:
9H-Carbazole, 1-nitromay have potential applications in the field of material science, where its unique properties could be utilized in the development of new materials with specific characteristics.
It is important to handle and store 9H-Carbazole, 1-nitrowith caution, as it may pose health and environmental hazards if not properly managed.

InChI:InChI=1/C12H8N2O2/c15-14(16)11-7-3-5-9-8-4-1-2-6-10(8)13-12(9)11/h1-7,13H

Upstream product

• 86-74-8 9H-carbazole 
• 574-39-0 9-acetylcarbazole 
• 2788-23-0 9-nitroso-9H-carbazole 
• 40310-53-0 3-nitrosocarbazole 
• 31438-20-7 9-nitro-9H-carbazole 
• 2229-36-9 1-(2-nitrophenyl)-1H-benzo[d][1,2,3]triazole 
• 3165-71-7 9-tosyl-9H-carbazole 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 855179-34-9 1-nitro-9-phenyl-carbazole 
• 101936-31-6 1-nitro-9-p-tolyl-carbazole 
• 102554-79-0 4-(1-nitro-carbazol-9-yl)-benzoic acid methyl ester 
• 66243-81-0 9-methyl-1-nitro-9H-carbazole 
• 18992-86-4 1-aminocarbazole 
• 5416-22-8 3,6-dibromo-1-nitrocarbazole 
• 1426925-62-3 C₆₀H₄₄N₄Si₂ 
• 408329-44-2 N-(p-toluenesulfonyl)-1-nitrocarbazole 
• 1454710-49-6 C₁₈H₁₁FN₂O₂ 
• 1454710-48-5 N-(p-oxymethylphenyl)-1-nitrocarbazole 
• 1454710-47-4 N-(p-benzhydrylphenyl)-1-nitrocarbazole 
• 1454710-46-3 N-benzhydryl-1-nitrocarbazole 
• 1454710-73-6 C₃₇H₃₂N₂O₄S₃ 
• 1454710-72-5 C₃₆H₂₉FN₂O₂S₂ 

Relevant articles and documents

Carbazole N-substituent effect upon DTMA: Stabilizing and photochromic modulating

Dithienylmaleimide derivatives 7-27 were synthesized by introducing N-substituted carbazole for photo-stabilizing purpose, and the structures were fully confirmed. The photochromism and photo-stability were recorded via UV-vis spectra. Only ortho compounds 8-17 with N-substituents on carbazole moiety showed escalated photochromic change, while compound 7 and the para counterparts 18-27 showed no appreciable photochromism. Additionally, compounds 8-18 exhibited good photo-stability except 17 under 254 nm irradiation. The unstability of 17 may probably due to overrunning hindrance. These photochromic patterns indicated that hindrance and electronic effect mutually paid a decisive influence on the photochromism and photo-stability, which potentially exploited a new way to construct novel photochromic materials with regulable and conceivable performance.

Preparation and study of 1,8-di(pyrid-2′-yl)carbazoles

(Figure Presented) A series of three derivatives of 1,8-di(pyrid-2′- yl)carbazole were prepared by Stille-type coupling of 2-(tri-n-butylstannyl) pyridine with the appropriate 1,8-dibromocarbazole. The carbazoles were prepared by appropriate substitution methodologies on the parent carbazole or by palladium-catalyzed cyclization of di-(p-tolyl)amine to provide the carbazole ring system. An X-ray structure of the di-tert-butyl derivative confirmed that both pyridyl groups were oriented for favorable intramolecular H-bonding to the central N-H. Two orientations of the molecule were found in the unit cell and this observation was corroborated by two N-H stretching bands in the solid state IR. Substitution of N-H by N-D led to increased emission intensity through diminished intramolecular deactivation of the excited state. The di-tert-butyl derivative formed a tridentate complex with Pd(II), which showed a red-shifted band attributed to an intraligand charge transfer state.

Lithiation of pivaloylamino derivatives of dibenzofuran and 9-methylcarbazole

2-, 3- and 4-Pivaloylamino derivatives of dibenzofuran [compounds (5), (4) and (6), respectively] and analogous 3-, 2- and 1-substituted derivatives of 9-methylcarbazole [compounds (8), (7) and (9), respectively] were subjected to lithiation at 0°C and subsequent reaction with dimethylformamide. Aldehyde formation took place at positions α to δ to the heteroatom as follows: α for (4) and (7); δ for (5); δ and β (3 : 1) for (8); and α′ (6). No formylation occurred with (9).

Synthesis and isolation of nitro-β-carbolines obtained by nitration of commercial β-carboline alkaloids

Nitration of commercial full aromatic β-carboline alkaloids nor-harmane (1), harmane (2), harmine (3), harmol (4), and the 7-acetylated derivative of harmol (5) is described. Advantages and disadvantages of different nitration reagents which involve acidic conditions (HNO3/H+) and neutral conditions (Cu(NO3)2; ceric ammonium nitrate) are discussed. A complete 1H and 13C-nmr characterization including ms and also uv absorption spectra in neutral and acid media is presented. A detailed ei-ms and ld-tof-ms study is enclosed because the nitro-β-carbolines constitute a new family of β-carboline-like chromophores with potential use as matrix in uv-maldi-tof-ms.

A new method of nitration of carbazoles using ceric ammonium nitrate (CAN)

A convenient procedure for the mononitration of carbazole and 9-alkylcarbazoles using CAN in CH3CN in presence of SiO2 is reported. The results with 9-acetyl, 9-benzoyl and 9- benzenesulphonylcarbazoles are also discussed.

FLASH-VACUUM PYROLYSIS OF NITROARYLBENZOTRIAZOLES. A TANDEM MASS SPECTROMETRY STUDY

Tandem mass spectrometry (MS/MS) has been applied to investigate the behaviour of 1-(2-nitrophenyl)benzotriazole upon flash-vacuum pyrolysis (FVP) conditions.Above 500 deg C, is pyrolyzed to give a mixture of 1-nitrocarbazole , 1-hydroxycarbazole and carbazole .Under similar conditions, 2-(2-nitrophenyl)benzotriazole appears to be more stable; it is however partially isomerized into 8 at high temperatures.Aza analogs of 8, like 1-(2-nitro-4-pyridyl)benzotriazole also loose nitrogen above 500 deg C to give a mixture of 1-nitro-3-azacarbazole , 1-hydroxy-3-azacarbazole and 3-azacarbazole .

Nitration of the Acetanilide-type Compounds

Some aromatic compounds containing the imino group (NH) were nitrated in acetic acid or anhydride, and the ortho/para ratios were measured.N-Methyl derivatives of the aforementioned compounds are much less reactive when nitrated under comparable conditions and give significantly lower o/p ratios.These results along with the literature data support the hypothesis that the acetanilide-type compounds are nitrated via N-nitro intermediates.

Photolysis of N-Nitrosodiphenylamines and N-Nitrosocarbazole

N-Nitrosodiphenylamine, N-nitroso-2-nitrodiphenylamine and N-nitrosocarbazole on irradiation in benzene give products resulting from nitroso group migration.

Nitration in the Carbazole Series, II

9-Nitrocarbazole (1) was prepared and rearranged to give a mixture of 1-nitro- (2) and 3-nitrocarbazole (3) in the same ratio as observed in the case of the carbazole nitration.The evidence for the formation of 1 during the nitration of carbazole in acetic acid is given.The formation of C-nitro compounds during methylation of the 1,3,6,8-tetrachlorocarbazole/1,3,6,8-tetrachloro-9-nitrocarbazole complex can be explained by an alkali-catalysed nitramine rearrangement.The mechanism of this rearrangement is discussed.