18108-22-0

Basic information

• Product Name: (1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID
• Synonyms: ALPHA-AMINOBENZYLPHOSPHONIC ACID;(1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID;(1-AMINO-1-PHENYLMETHYL)PHOSPHONIC ACID;(alpha-aminobenzyl)-phosphonicaci;(aminophenylmethyl)-phosphonicaci;(aminophenylmethyl)phosphonicacid;(a-Aminobenzyl)phosphonic acid.;(1-AMINO-1-PHENYLMETHYL)PHOSPHONIC ACID 97%
• CAS NO: 18108-22-0
• Molecular Formula: C₇H₁₀NO₃P
• Molecular Weight: 187.13
• EINECS: 226-260-7
• Mol File: 18108-22-0.mol
• Article Data: 29

Chemical Properties

• Melting Point: 254-257 °C
• Boiling Point: 407.9°Cat760mmHg
• Flash Point: 200.5°C
• Appearance: White/Powder or Cyrstals
• Density: 1.446g/cm³
• Vapor Pressure: 2.19E-07mmHg at 25°C
• CAS DataBase Reference: (1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID(18108-22-0)
• EPA Substance Registry System: (1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID(18108-22-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• Hazardous Substances Data: 18108-22-0(Hazardous Substances Data)

Usage

Description

(1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID, also known as a member of the phosphonic acid class, is a compound characterized by the presence of an amino(phenyl)methyl group attached to the phosphorus atom. It is typically found in the form of white crystals or powder and exhibits unique chemical properties that make it suitable for various applications across different industries.

Uses

Used in Chemical Synthesis:
(1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID is used as a synthetic building block for the development of new compounds and materials. Its unique structure allows for the creation of novel molecules with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Industry:
(1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID is used as a key intermediate in the synthesis of pharmaceutical compounds. Its versatile structure enables the development of new drugs with improved efficacy and reduced side effects, addressing unmet medical needs.
Used in Agrochemical Industry:
(1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID is used as a starting material for the synthesis of agrochemicals, such as pesticides and herbicides. Its unique properties contribute to the development of more effective and environmentally friendly products for agricultural applications.
Used in Materials Science:
(1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID is used as a component in the development of advanced materials with specific properties, such as improved mechanical strength, thermal stability, or chemical resistance. These materials can be utilized in various applications, including aerospace, automotive, and electronics industries.
Used in Research and Development:
(1-AMINO-1-CYCLOHEXYL)PHOSPHONIC ACID is used as a research tool for studying the properties and behavior of phosphonic acids and their derivatives. Its unique structure provides valuable insights into the fundamental chemistry of these compounds, leading to the discovery of new applications and improvements in existing technologies.

InChI:InChI=1/C7H10NO3P/c8-7(12(9,10)11)6-4-2-1-3-5-6/h1-5,7H,8H2,(H2,9,10,11)/p-1/t7-/m1/s1

Upstream product

• 62506-88-1 N-benzylidenediphenylmethanamine 
• 868-85-9 Dimethyl phosphite 
• 780-25-6 N-benzylidene benzylamine 
• 106787-37-5 Diphenyl α-(diethoxyphosphinylamino)-benzylphosphonate 
• 82684-76-2 1-(N-acetylamino)-1-phenylmethyl-phosphonic acid 
• 6907-68-2 N-[phenyl(acetylamino)methyl]acetamide 
• 16814-08-7 diethyl 1-aminophenylmethylphosphonate 
• 100-47-0 benzonitrile 
• 100-52-7 benzaldehyde 
• 18108-19-5 Fluorsulfonylaminophenylmethanphosphonsaeurediethylester 
• 31641-78-8 ethyl 2-diethoxyphosphoryl-2-phenylacetate 
• 52111-18-9 (Carbamoyl-phenyl-methyl)-phosphonic acid diethyl ester 
• 25881-35-0 (R,S)-<α-(Benzylamino)benzyl>phosphonsaeure 
• 122183-98-6 diethyl 2-(p-nitrophenyl)benzohydrazonoyl>phosphonate 

Downstream Products

• 71864-34-1 (tert-Butoxycarbonylamino-phenyl-methyl)-phosphonic acid 
• 53558-70-6 α-(N-benzyloxycarbonyl)amino-benzylphosphonic acid 
• 53044-42-1 Tri-N,O,O-(trimethylsilyl)-aminobenzylphosphonsaeure 
• 866605-69-8 [(2,2-Dimethyl-propionylamino)-phenyl-methyl]-phosphonic acid 
• 18108-22-0 D-1-Amino-1-phenylmethylphosphonic acid 
• 18108-22-0 L-1-Amino-1-phenylmethylphosphonic acid 
• 104513-37-3 D-1-(N-Phenylacetylamino)-1-phenylmethylphosphonic acid 
• 104513-37-3 1-(N-Phenylacetylamino)-1-phenylmethylphosphonic acid 
• 100-52-7 benzaldehyde 
• 100-47-0 benzonitrile 
• 100-51-6 benzyl alcohol 
• 36992-14-0 L-Phenylalanine phosphonate 
• 37714-06-0 (S)-amino(phenyl)methylphosphonic acid 
• 37714-05-9 (R)-1-amino-1-phenylmethylphosphonic acid 

Relevant articles and documents

Extremely short H?H distances and intermolecular hydrogen-bonding patterns of dialkyl α-aryl-α-(diphenylmethylamino)methanephosphonates

Single crystal X-ray diffraction studies of four N-benzhydryl protected diethyl α-amino-α-arylmethanephosphonates (aryl = phenyl, 1-naphthyl, 1-anthryl, and 1-pyrenyl) reveal several distinct types of hydrogen bonding, leading to the formation of (a) dime

1-(Acylamino)alkylphosphonic acids—alkaline deacylation

The alkaline deacylation of a representative series of 1-(acylamino)alkylphosphonic acids [(AC)-AAP: (AC) = Ac, TFA, Bz; AAP = GlyP, AlaP, ValP, PglP and PheP] in an aqueous solution of KOH (2M) was investigated. The results suggested a two-stage reaction mechanism with a quick interaction of the hydroxyl ion on the carbonyl function of the amide R-C(O)-N(H)- group in the first stage, which leads to instant formation of the intermediary acyl-hydroxyl adducts of R-C(O?)2-N(H)-, visible in the 31P NMR spectra. In the second stage, these intermediates decompose slowly by splitting of the RC(O?)2-N(H)- function with the subsequent formation of 1-aminoalkylphosphonate and carboxylate ions.

A Methylidene Group in the Phosphonic Acid Analogue of Phenylalanine Reverses the Enantiopreference of Binding to Phenylalanine Ammonia-Lyases

Aromatic amino acid ammonia-lyases and aromatic amino acid 2,3-aminomutases contain the post-translationally formed prosthetic 3,5-dihydro-4-methylidene-5H-imidazol-5-one (MIO) group. MIO enzymes catalyze the stereoselective synthesis of α- or β-amino acid enantiomers, making these chemical processes environmentally friendly and affordable. Characterization of novel inhibitors enables structural understanding of enzyme mechanism and recognizes promising herbicide candidates as well. The present study found that both enantiomers of the aminophosphonic acid analogue of the natural substrate phenylalanine and a novel derivative bearing a methylidene at the β-position inhibited phenylalanine ammonia-lyases (PAL), representing MIO enzymes. X-ray methods unambiguously determined the absolute configuration of all tested enantiomers during their synthesis. Enzyme kinetic measurements revealed the enantiomer of the methylidene-substituted substrate analogue as being a mirror image relation to the natural l-phenylalanine as the strongest inhibitor. Isothermal titration calorimetry (ITC) confirmed the binding constants and provided a detailed analysis of the thermodynamic driving forces of ligand binding. Molecular docking suggested that binding of the (R)- and (S)-enantiomers is possible by a mirror image packing. (Figure presented.).