17345-77-6

Basic information

• Product Name: 4-BROMOCATECHOL
• Synonyms: 4-Bromo-1,2-benzenediol;4-BROMO-1,2-DIHYDROXYBENZENE;4-BROMOCATECHOL;4-bromopyrocatechol;1,2-Benzenediol, 4-broMo-;4-broMobenzene-1,2-diol
• CAS NO: 17345-77-6
• Molecular Formula: C₆H₅BrO₂
• Molecular Weight: 189.01
• EINECS: 241-370-5
• Mol File: 17345-77-6.mol
• Article Data: 49

Chemical Properties

• Melting Point: 87 °C
• Boiling Point: 280.5 °C at 760 mmHg
• Flash Point: 123.5 °C
• Appearance: /
• Density: 1.844 g/cm³
• Vapor Pressure: 0.00222mmHg at 25°C
• Refractive Index: 1.657
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO
• PKA: 8.84±0.10(Predicted)
• CAS DataBase Reference: 4-BROMOCATECHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMOCATECHOL(17345-77-6)
• EPA Substance Registry System: 4-BROMOCATECHOL(17345-77-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25
• Hazardous Substances Data: 17345-77-6(Hazardous Substances Data)

Usage

Chemical Properties

Grey powder

Uses

A type of human dopamine sulfotransferase, belonging to the catechol family of molecules.

InChI:InChI=1/C6H5BrO2/c7-4-1-2-5(8)6(9)3-4/h1-3,8-9H

Upstream product

• 73790-19-9 5-bromo-2,2-dimethyl-1,3-benzodioxole 
• 120-80-9 benzene-1,2-diol 
• 2859-78-1 4-Bromoveratrole 
• 106-41-2 4-bromo-phenol 
• 91-22-5 quinoline 
• 7664-93-9 sulfuric acid 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 56-23-5 tetrachloromethane 
• 7722-84-1 dihydrogen peroxide 
• 1761-61-1 5-bromosalicyclaldehyde 
• 91-16-7 1,2-dimethoxybenzene 
• 7368-78-7 4-bromoguaiacol 
• 37942-01-1 5-bromo-2-methoxyphenol 

Downstream Products

• 683234-38-0 4-bromo-1,2-dibutoxybenzene 
• 291753-67-8 4-bromine-1,2-bis(octyloxy)benzene 
• 200959-51-9 4-bromo-1,2-bis(hexyloxy)benzene 
• 233661-07-9 1-bromo-3,4-bis(decyloxy)benzene 
• 210834-64-3 1-bromo-3,4-bis(dodecyloxy)benzene 
• 16047-57-7 (((4-bromo-1,2-phenylene)bis(oxy))bis(methylene))dibenzene 
• 193554-93-7 2,6-dichloro-2-oxo-4-phenylbenzo[e]-1,2λ⁵-oxaphosphorin-3-ene 
• 193554-97-1 6-chloro-2-hydroxy-4-phenylbenzo[e][1,2λ⁵]oxaphosphinine 2-oxide 
• 193554-95-9 2,6-dichloro-2-oxo-4-(4-bromophenyl)benzo[e]-1,2λ⁵-oxaphosphorin-3-ene 
• 332346-65-3 7-bromo-2,6-dichloro-2-oxo-4-phenylbenzo[e]-1,2λ⁵-oxaphosphorin-3-ene 
• 73790-19-9 5-bromo-2,2-dimethyl-1,3-benzodioxole 

Relevant articles and documents

Extended triphenylenes: Synthesis, mesomorphic properties and molecularly resolved scanning tunneling microscopy images of hexakis(dialkoxyphenyl)triphenylenes and dodeca(alkoxy) tris(triphenylenylene)s

Palladium-catalyzed cross-coupling between 3,4-dialkoxyphenylboronic acids (1a-d) and 2,3,6,7,10,11-hexabromotriphenylene (2) provided 2,3,6,7,10,11-hexakis[3,4-bis(alkoxy)phenyl]triphenylenes, C18H6[C6H3(OC(n)H(2n + 1)2]6 where n = 6, 8, 10, and 12 (3a-d). Cyclodehydrogenation of the aryl-substituted triphenylenes 3a-d using ferric chloride oxidation followed by methanol reduction produced 6,6',6'',7,7',7'',10,10',10'',11,11',11''-dodecaalkoxy-2,3':3,2':2',3''- tris(triphenylenylene)s, C54H18(OC(n)H(2n + 1))12 where n = 6, 8, 10, and 12 (4a-d). The mesomorphic properties of the compounds 3a-d and 4a-d were investigated by differential scanning calorimetry (DSC) measurements, polarizing microscopy, and wide angle X-ray diffraction (WAXD). The triphenylenes 3a-d exhibited a columnar mesophase in the range of 111-126, 85-104, 74-103, and 47-101 °C, respectively. Upon oxidation of the moiety, the columnar mesophases shift to higher temperatures and exist in a much broader range of temperatures: for the tris(triphenylenylene)s 4a-d, they have been observed in the range of 180-430, 150-370, 120-322, and 104-306 °C, respectively. Finally, the self-assembly at the interface between a solution of 4c and a graphite substrate has been studied by scanning tunneling microscopy. Molecularly resolved imaging revealed a highly ordered monolayer exhibiting a two-dimensional hexagonal lattice.

Liquid-crystalline TADF materials based on substituted carbazoles and terephthalonitrile

By functionalising 2,5-di(N,N′-carbazolyl)terephthalonitrile or 2,3,5,6-tetra(N,N′-carbazolyl)terephthalonitrile with alkoxy chains located on the carbazole moiety, a family of materials is realised, all of which show a TADF response and two of which are also liquid crystalline. This journal is

Regioselective bromination of arenes mediated by triphosgene-oxidized bromide

This article first time describes triphosgene (BTC) as an oxidant while the non-toxic and easy-to-handle potassium bromide (KBr) as the source of bromine to the bromination reaction of aromatic substrates. The novel brominating protocol gives excellent para-regioselectivity of the alkoxyl/hydroxyl arenes and high yield, offering good potential of commercial scale applications. The mechanism of “Triphosgene oxidize bromide” was proposed.

Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide-Dimethyl Sulfoxide

Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o -hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.