6810-26-0

Basic information

• Product Name: N-HYDROXY-4-AMINOBIPHENYL
• Synonyms: N-Biphenyl-4-yl-hydroxylamine;N-Hydroxy-4-aminobiphenyl Discontinued;4-N-HYDROXYLAMINOBIPHENYL;4-N-HYDROXYAMINOBIPHENYL;4-HYDROXYLAMINOBIPHENYL;Biphenyl-4-ylhydroxyamine;N-Hydroxybiphenyl-4-amine;(1,1'-Biphenyl)-4-amine, N-hydroxy-
• CAS NO: 6810-26-0
• Molecular Formula: C₁₂H₁₁NO
• Molecular Weight: 185.22
• Product Categories: Metabolites;Mutagenesis Research Chemicals
• Mol File: 6810-26-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 319.45°C (rough estimate)
• Appearance: /
• Density: 1.0936 (rough estimate)
• Refractive Index: 1.5300 (estimate)
• Stability: Moisture and Temperature Sensitive
• CAS DataBase Reference: N-HYDROXY-4-AMINOBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: N-HYDROXY-4-AMINOBIPHENYL(6810-26-0)
• EPA Substance Registry System: N-HYDROXY-4-AMINOBIPHENYL(6810-26-0)

Safety Data

• Hazardous Substances Data: 6810-26-0(Hazardous Substances Data)

Usage

Description

N-HYDROXY-4-AMINOBIPHENYL, also known as 4-Amino-N-hydroxybiphenyl, is an organic compound with the chemical formula C12H11NO. It is a yellow solid and is primarily used in organic synthesis due to its unique chemical properties.

Uses

Used in Organic Synthesis:
N-HYDROXY-4-AMINOBIPHENYL is used as a synthetic building block for the creation of various organic compounds. Its chemical structure allows it to be a versatile intermediate in the synthesis of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-HYDROXY-4-AMINOBIPHENYL is used as a key intermediate in the development of new drugs. Its unique chemical properties enable the creation of novel drug candidates with potential therapeutic applications.
Used in Chemical Research:
N-HYDROXY-4-AMINOBIPHENYL is also utilized in chemical research as a model compound to study various reaction mechanisms and to develop new synthetic methodologies. Its reactivity and structural features make it an attractive candidate for exploring new chemical transformations and understanding fundamental organic chemistry concepts.
Used in Material Science:
In the field of material science, N-HYDROXY-4-AMINOBIPHENYL can be used as a component in the development of new materials with specific properties, such as conductivity, magnetism, or optical characteristics. Its incorporation into polymers or other materials can lead to the creation of novel materials with enhanced performance.

Safety Profile

Questionable carcinogen withexperimental carcinogenic data. Human mutation datareported. When heated to decomposition it emits highlytoxic fumes of NOx.

Upstream product

• 92-93-3 1-phenyl-4-nitrobenzene 
• 60-29-7 diethyl ether 
• 92-52-4 biphenyl 

Downstream Products

• 10125-76-5 4-nitroso-1,1′-biphenyl 
• 92-67-1 4-phenylalanine 
• 7334-12-5 1,2-di([1,1'-biphenyl]-4-yl)diazene oxide 
• 5326-53-4 1,2-di([1,1'-biphenyl]-4-yl)diazene 
• 26690-77-7 N-Hydroxy-4-biphenylbenzamide 
• 1426845-68-2 8-[acetyl(4-biphenylyl)amino]-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine 
• 861518-23-2 N-biphenyl-4-yl-N-methyl-toluene-4-sulfonamide 
• 65690-69-9 N-([1,1'-biphenyl]-4-yl)-4-methylbenzenesulfonamide 
• 7466-42-4 4-phenylazobenzene 
• 117205-56-8 2-(N'-Biphenyl-4-yl-hydrazino)-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one 

Relevant articles and documents

Glucuronide conjugates of 4-aminobiphenyl and its N-hydroxy metabolites pH stability and synthesis by human and dog liver

Glucuronide conjugates of arylamines are thought to be important in the carcinogenic process. This study investigated the pH stability and synthesis of glucuronide conjugates of 4-aminobiphenyl and its N-hydroxy metabolites by human and dog liver. Both dog and human liver slices incubated with 0.06 mM [3H]-4-aminobiphenyl produced the N-glucuronide of 4-aminobiphenyl as the major product. After 2 hr of incubation, the N-glucuronide of 4-aminobiphenyl represented 52 and 27% of the total radioactivity recovered by HPLC in dog and human, respectively. When 4-aminobiphenyl, N-hydroxy-4-aminobiphenyl, or N-hydroxy-N-acetyl-4-aminobiphenyl was added to human microsomes containing [14C]UDP-glucuronic acid, a new product peak was detected by HPLC. At 0.5 mM, the rate of glucuronidation was N-hydroxy-N-acetyl-4-aminobiphenyl > N-hydroxy-4-aminobiphenyl > 4-aminobiphenyl. The rate of formation of the N-glucuronide of 4-aminobiphenyl was similar to that observed with benzidine and N-acetylbenzidine. The glucuronides of 4-aminobiphenyl and N-hydroxy-4-aminobiphenyl were both acid labile with T1/2 values of 10.5 and 32 min, respectively, at pH 5.5. The glucuronide of N-hydroxy-N-acetyl-4-aminobiphenyl was not acid labile with T1/2 values at pH 5.5 and 7.4 of 55 and 68 min, respectively. The glucuronide of 4-aminobiphenyl was the most acid labile conjugate examined. Thus, the glucuronide of 4-aminobiphenyl is a major product of dog and human liver slice metabolism and likely to play an important role in the carcinogenic process. BIOCHEM PHARMACOL 51;12:1679-1685, 1996.

Electrochemically Tuned Oxidative [4+2] Annulation and Dioxygenation of Olefins with Hydroxamic Acids

This work represents the first [4+2] annulation of hydroxamic acids with olefins for the synthesis of benzo[c][1,2]oxazines scaffold via anode-selective electrochemical oxidation. This protocol features mild conditions, is oxidant free, shows high regioselectivity and stereoselectivity, broad substrate scope of both alkenes and hydroxamic acids, and is compatible with terpenes, peptides, and steroids. Significantly, the dioxygenation of olefins employing hydroxamic acid is also successfully achieved by switching the anode material under the same reaction conditions. The study not only reveals a new reactivity of hydroxamic acids and its first application in electrosynthesis but also provides a successful example of anode material-tuned product selectivity.

Capturing labile sulfenamide and sulfinamide serum albumin adducts of carcinogenic arylamines by chemical oxidation

Aromatic amines and heterocyclic aromatic amines (HAAs) are a class of structurally related carcinogens that are formed during the combustion of tobacco or during the high temperature cooking of meats. These procarcinogens undergo metabolic activation by