30825-34-4

Basic information

• Product Name: 3-AMINO-5-(TRIFLUOROMETHYL)BENZONITRILE
• Synonyms: CIS (+) HYDROXY LACTAM;3-amino-5-(trifluoromethyl)benzonitrile;3-AMino-5-cyanobenzotrifluoride;trans-2,3-Dihydro-3-hydroxy-2-(4-Methoxyphenyl)-1,5-benzothiazepin-4(5H)-one;(2R,3S)-3-Hydroxy-2-(4-Methoxyphenyl)-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one;Moxifloxacin Impurity V
• CAS NO: 30825-34-4
• Molecular Formula: C₁₆H₁₅NO₃S
• Molecular Weight: 186.13
• Mol File: 30825-34-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 279.316 °C at 760 mmHg
• Flash Point: 122.726 °C
• Appearance: /
• Density: 1.371 g/cm³
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 12.37±0.40(Predicted)
• CAS DataBase Reference: 3-AMINO-5-(TRIFLUOROMETHYL)BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-5-(TRIFLUOROMETHYL)BENZONITRILE(30825-34-4)
• EPA Substance Registry System: 3-AMINO-5-(TRIFLUOROMETHYL)BENZONITRILE(30825-34-4)

Safety Data

• Hazardous Substances Data: 30825-34-4(Hazardous Substances Data)

Usage

Description

3-AMINO-5-(TRIFLUOROMETHYL)BENZONITRILE is an organic compound with the molecular formula C8H5F3N2. It is characterized by its trifluoromethyl group and nitrile functional group, which contribute to its unique chemical properties and reactivity.

Uses

Used in Organic Synthesis:
3-AMINO-5-(TRIFLUOROMETHYL)BENZONITRILE is used as a research reagent for organic synthesis. Its unique structure allows it to be a valuable building block in the development of various organic compounds, particularly those with pharmaceutical or chemical applications.
Used in Chemical Processes:
In addition to its role in organic synthesis, 3-AMINO-5-(TRIFLUOROMETHYL)BENZONITRILE is also utilized in other chemical processes. Its reactivity and functional groups make it a versatile compound for use in the development of new materials, catalysts, and other chemical products.

InChI:InChI=1/C8H5F3N2/c9-8(10,11)6-1-5(4-12)2-7(13)3-6/h1-3H,13H2

Upstream product

• 30193-57-8 (+/-)-(R*,R*)-β-<(2-aminophenyl)thio>-α-hydroxy-4-methoxybenzenepropanoic acid 
• 30193-56-7 (+/-)-(R*,R*)-β-[(2-aminophenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid, methyl ester 
• 137-07-5 2-amino-benzenethiol 
• 96125-49-4 methyl trans-3-(4-methoxyphenyl)glycidate 
• 30193-56-7 (2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4''-methoxyphenyl)-propionic acid methyl ester 
• 42245-42-1 methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate 
• 30193-57-8 erythro-(-)-3-((2-aminophenyl)thio)-2-hydroxy-3-(4-methoxyphenyl)propionic acid 
• 30193-57-8 erythro-(+)-3-((2-aminophenyl)thio)-2-hydroxy-3-(4-methoxyphenyl)propionic acid 
• 30067-00-6 (2RS,3SR)-2-hydroxy-3-(4-methoxy-phenyl)-3-(2-nitro-phenylsulfanyl)-propionic acid methyl ester 
• 154076-93-4 ethyl (Z)-2-(2-methoxyethoxy)methoxy-3-(4-methoxyphenyl)-2-propenoate 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 128488-33-5 (2R,3R)-2-Benzyl-5-(2-dimethylamino-ethyl)-3-hydroxy-2-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 128488-20-0 Acetic acid (2R,3S)-2-benzyl-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester 
• 128488-20-0 Acetic acid (2R,3R)-2-benzyl-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester 
• 128488-11-9 (2R,3R)-2-Benzyl-4-ethoxy-2-(4-methoxy-phenyl)-2,3-dihydro-benzo[b][1,4]thiazepin-3-ol 
• 128488-11-9 (2R,3S)-2-Benzyl-4-ethoxy-2-(4-methoxy-phenyl)-2,3-dihydro-benzo[b][1,4]thiazepin-3-ol 
• 128488-31-3 (2R,3R)-5-(2-Dimethylamino-ethyl)-2-ethyl-3-hydroxy-2-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 128488-32-4 (2R,3R)-2-Allyl-5-(2-dimethylamino-ethyl)-3-hydroxy-2-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 128488-19-7 Acetic acid (2R,3S)-2-allyl-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester 
• 128488-19-7 Acetic acid (2R,3R)-2-allyl-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester 
• 128488-30-2 (2RS,3RS)-5-<2-(dimethylamino)ethyl>-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-2-methyl-1,5-benzothiazepin-4(5H)-one 
• 128488-13-1 (2S,3S)-2-Benzyl-3-hydroxy-2-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 128488-13-1 (2S,3R)-2-Benzyl-3-hydroxy-2-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 128488-18-6 Acetic acid (2R,3S)-2-ethyl-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester 
• 128488-18-6 Acetic acid (2R,3R)-2-ethyl-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester 

Relevant articles and documents

Optical resolution of a 1,5-benzothiazepine derivative, a synthetic intermediate of diltiazem, by preferential crystallization and diastereomeric salt formation

Practical preparation methods of an optically active intermediate of diltiazem, (+)-(2S,3S)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2- (4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one [(+)-7], have been developed by the use of physicochemical and chemical resolutions. 1) The salt of (+)-7 with 3-amino-4-hydroxy-benzenesulfonic acid (AHS), was found to exist as a conglomerate and could be reproducibly resolved into (+)-7·AHS and (-)- 7·AHS of 94-98% ee by a preferential crystallization procedure. 2) (+)- (1R)-3-Bromocamphor-9-sulfonic acid [(+)-BCS] was found to be an efficient resolving agent for (±)-7 and the diastereomeric resolution provided (+)- 7·(+)-BCS·2H2O salt in >43% yield and >97% ee by fractional crystallization. It is presumed that the crystal water of (+)-7·(+)- BCS·2H2O plays an important role in the selective crystallization during this efficient resolution.

Enantiomer associations in the crystal structures of racemic and (2S,3R)-(-)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)- one

The crystal structures of racemic and (2S,3R)-(-)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)- one (C16H15NO3S) have been determined in order to compare the interactions between molecules of the same and opposite chirality. The enantiomeric associations observed in these two crystal structures are analysed, relating the differences to those found in the equivalent diastereomers, (2R, 3R) and/or (2S, 3S). Single-crystal X-ray diffraction data were collected at low temperature with Cu Kα radiation (λ = 1.54184 A). Optically active: monoclinic, space group C2, with a = 24.726(3), b = 5.2426(5), c =12.0726(12) A, β - 112.979(9)°, V = 1440.8(5) A3, Z = 4, Dx= 1.389 g cm-3, μ = 20.35 cm-1, the refinement on 2918 observed reflections gave R=0.0271. Racemic: monoclinic, space group P21/n, with a = 13.308(3), b = 4.8474(8), c = 22.130(4) A, β = 91.782(14), V= 1426.9(5) A3, Z=4, Dx= 1.403 g cm-3, μ= 20.54 cm-1, refined to R = 0.0318 for 2753 observed reflections. An intramolecular hydrogen bond between the hydroxy and carbonyl groups appears to stabilize the benzothiazepinone ring in the (P,2S,3R) boat conformation with the hydroxy and methoxyphenyl substituents in equatorial positions. In both crystal structures two N-H...O hydrogen bonds connect the molecules into dimers. In the optically active compound the two molecules are related by a twofold axis, in the racemate by an inversion centre. The racemate contains an additional hydrogen bond which is reflected by its higher melting enthalpy compared with the optically active compound. The difference in the chiral discrimination in the solutions of the cis-and trans-diastereomers does not appear to have its origin in the strong (O-H...O, N-H...O) hydrogen bonds, but rather in the weak (C-H...O) interactions. Acta Chemica Scandinavica 1996.

Stereoselective addition of 2-aminothiophenol to α-alkoxycinnamic acid derivatives - Alternative synthesis of (±)-diltiazem

A stereocontrolled synthesis of (±)-diltiazem by applying nucleophilic addition of 2-aminothiophenol to α-alkoxycinnamic acid derivatives is described.