13037-60-0

Basic information

• Product Name: 2-BROMOPHENYL ISOTHIOCYANATE
• Synonyms: O-BROMOPHENYL ISOTHIOCYANATE;2-BROMOPHENYL ISOTHIOCYANATE;ISOTHIOCYANIC ACID 2-BROMOPHENYL ESTER;2-Bromophenyl isothiocyanate,98%;2-BroMophenyl isothiocyanate, 98% 5GR;2-Bromophenyl isothiocyate, 99%
• CAS NO: 13037-60-0
• Molecular Formula: C₇H₄BrNS
• Molecular Weight: 214.08
• EINECS: 264-732-4
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiocyanates/Isothiocyanates;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds
• Mol File: 13037-60-0.mol

Chemical Properties

• Melting Point: 20 °C
• Boiling Point: 257 °C
• Flash Point: >110°C
• Appearance: clear light yellow liquid
• Density: 1.591 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0115mmHg at 25°C
• Refractive Index: 1.685
• Sensitive: Moisture Sensitive
• BRN: 2802536
• CAS DataBase Reference: 2-BROMOPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMOPHENYL ISOTHIOCYANATE(13037-60-0)
• EPA Substance Registry System: 2-BROMOPHENYL ISOTHIOCYANATE(13037-60-0)

Safety Data

• Hazard Codes: Xn,Xi,C
• Statements: 36/37/38-20/21/22-42
• Safety Statements: 36/37/39-26-45-36/37-22
• RIDADR: 2810
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 13037-60-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Chemical Industries:
2-Bromophenyl isothiocyanate is used as a key intermediate in the synthesis of various pharmaceutical compounds and organic molecules. Its unique structure allows it to be a versatile building block for creating new and innovative products.
Used in the Synthesis of 1,4-Dihydro-3,1-Benzoxazine-2-Thiones:
In the field of organic chemistry, 2-bromophenyl isothiocyanate is employed as a reagent for the synthesis of 4-monosubstituted and 4,4-disubstituted 1,4-dihydro-3,1-benzoxazine-2-thiones. These compounds have potential applications in various areas, including pharmaceuticals and materials science, due to their unique chemical properties and potential biological activities.

InChI:InChI=1/C7H4BrNS/c8-6-3-1-2-4-7(6)10-5-9/h1-4H

Upstream product

• 463-71-8 thiophosgene 
• 615-36-1 2-bromoaniline 
• 38435-47-1 2-bromo N-hydroxybenzimidoyl chloride 
• 333-20-0 potassium thioacyanate 
• 94718-79-3 o-bromoaniline hydrochloride 
• 34158-72-0 2-bromobenzaldehyde oxime 
• 58654-89-0 triethylammonium o-bromophenyl dithiocarbamate salt 
• 75-15-0 carbon disulfide 
• 2926-29-6 Langlois reagent 
• 102368-13-8 1,1'-Thiocarbonyldi-2(1H)-pyridone 
• 103-72-0 phenyl isothiocyanate 

Downstream Products

• 5391-30-0 1-(2-bromophenyl)thiourea 
• 52550-98-8 N,N'-bis(o-bromophenyl)thiourea 
• 135085-66-4 Indole-1-carbothioic acid (2-bromo-phenyl)-amide 
• 122834-31-5 (2-Bromo-phenyl)-[(3aS,6aS)-5,5-dioxo-hexahydro-5λ⁶-thieno[3,4-d]thiazol-(2E)-ylidene]-amine 
• 122834-28-0 C₁₁H₁₁BrN₂O₂S₂ 
• 127142-15-8 C₁₅H₁₅BrN₆S₂ 
• 23921-67-7 3-(2-bromophenyl)-4-oxo-2-thioxo-1,2,3,4-tetrahydroquinazoline 
• 56676-48-3 3-(o-bromophenyl)rhodanine 
• 223396-45-0 1-(2-bromophenyl)-(1,2-dideoxy-α-D-glucofurano)<2,1-d>imidazolidine-2-thione 
• 342006-03-5 C₁₇H₁₅BrN₆OS 

Relevant articles and documents

Thiourea type nitrogen phosphine ligand and preparation method and application thereof

The invention provides a thiourea type nitrogen phosphine ligand and a preparation method and application thereof. The thiourea-type nitrogen phosphine ligand is reacted with aromatic amine and aryl isothiocyanate to obtain aryl thiourea, and then reacted

Design, synthesis and biological evaluation of novel 2,4-disubstituted quinazoline derivatives targeting H1975 cells via EGFR-PI3K signaling pathway

In order to find new and highly effective anti-tumor drugs with targeted therapeutic effects, a series of novel 4-aminoquinazoline derivatives containing N-phenylacetamide structure were designed, synthesized and evaluated for antitumor activity against four human cancer cell lines (H1975, PC-3, MDA-MB-231 and MGC-803) using MTT assay. The results showed that the compound 19e had the most potent antiproliferative activity against H1975, PC-3, MDA-MB-231 and MGC-803 cell lines. At the same time, compound 19e could significantly inhibit the colony formation and migration of H1975 cells. Compound 19e also arrested the H1975 cell cycle in the G1 phase and mediated cell apoptosis, promoted the accumulation of ROS in H1975 cells. Furthermore, compound 19e exerted antitumor effect in vitro by reducing the expression of anti-apoptotic protein Bcl-2 and increasing the pro-apoptotic protein Bax and p53. Mechanistically, compound 19e could significantly decreased the phosphorylation of EGFR and its downstream protein PI3K in H1975 cells. Which indicated that compound 19e targeted H1975 cell via interfering with EGFR-PI3K signaling pathway. Molecular docking showed that compound 19e could bind into the active pocket of EGFR. Those work suggested that compound 19e would have remarkable implications for further design of anti-tumor agents.

Thiosemicarbazone-based lead optimization to discover high-efficiency and low-toxicity anti-gastric cancer agents

In this paper, a series of thiosemicarbazone derivatives containing different aromatic heterocyclic groups were synthesized and the tridentate donor system of the lead compound was optimized. Most of the target compounds showed improved antiproliferative activity against MGC803 cells. SAR studies revealed that compound 5d displayed significant advantages in inhibition effect with an IC50 value of 0.031 μM, and better selectivity between cancer and normal cells than 3-AP and DpC (about 15- and 5-fold improved respectively). Besides, compound 5d showed selective antiproliferative activity in not only other cancer cells but also different gastric cancer cell lines. In-depth mechanism studies showed that compound 5d could induce mitochondria-related apoptosis which might be related to the elevation of intracellular ROS level, and cause cell cycle arrest at S phase. Moreover, 5d could evidently suppress the cell migration and invasion by blocking the EMT (epithelial–mesenchymal transition) process. Consequently, our studies provided a lead optimization strategy of thiosemicarbazone derivatives which would contribute to discover high-efficiency and low-toxicity agents for the treatment of gastric cancer.

Organophosphine-free copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur

A copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur in the absence of organophosphine has been established. This approach represents a simple and efficient one-pot synthesis of isothiocyanates, and features excellent functional group tolerance and the use of a cheap, safe and odorless sulfur source. Moreover, this process could directly provide isothiocyanate analogous bioactive molecules, thiocarbonyl-containing pesticides and facile construction of benzoxazole and benzimidazole frames.

Isothiocyanate synthesized by three components and preparation method of isothiocyanate

The invention discloses isothiocyanate and a preparation method thereof. The method comprises the steps that primary amine, sodium difluorobromoacetate and elemental sulfur are taken as reactants forreaction; the reaction is carried out under the action of a copper catalyst, wherein the copper catalyst is any one of cuprous chloride, copper bromide, cuprous iodide, copper chloride and copper trifluoromethanesulfonate; an alkali is also added, wherein the alkali is any one of sodium bicarbonate, potassium carbonate, cesium carbonate, potassium phosphate, DABCO and sodium tert-butoxide; the whole reaction is carried out in a solvent, wherein the solvent is acetonitrile or dimethyl sulfoxide, the reaction temperature is 80-120 DEG C, and the reaction time is 10-14 hours. The method can directly synthesize the target product, does not need to separate intermediate products and only needs stirring and heating reaction under normal pressure to obtain the target product, and the yield can beup to 87%; a waste solution is fewer during the reaction, and the method protects the environment and ensures the health of an operator; in addition, a series of isothiocyanate derivatives can be prepared, and the method has a stronger substrate universality.

ALKYL SUBSTITUTED TRIAZOLE COMPOUNDS AS AGONISTS OF THE APJ RECEPTOR

Compounds of Formula I and Formula II, pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures: (I), (II) where the definitions of the variables are provided herein.

Isothiocyanate-Directed Ortho-Selective Halogenation of Arenes via C–H Functionalization

Abstract: Ortho-selective halogenation of arenes via C–H functionalization has been described under mild reaction conditions. In this reaction Cu(II)X2 was used as a halide source. It is a simple, general and efficient method for the synthesis of 2-halo aromatic isothiocyanates. All the reactions are carried out under optimized reaction conditions to provide their respective desired products in good to high yield. Graphical Abstract: We have developed a general, simple and efficient method for the synthesis of 2-halo arylisothiocyanates from isothiocyanates through ortho-selective halogenation under mild reaction conditions. Cu(II)X2 was used as a halide source for this methodology. All the reactions are carried out under optimized reaction conditions to provide their respective desired products in good to high yield. [Figure not available: see fulltext.].

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea against Meloidogyne incognita

Two series of novel 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea were designed and synthesized. The bioassay results showed that most of the test compounds showed good nematicidal activity against M. incognita at the concentration of 10.0?mg?L?1 in vivo. The compounds A13, A17 and B3 showed excellent nematicidal activity on the second stage juveniles of the root-knot nematode with the inhibition rate of 51.3%, 58.3% and 51.3% at the concentration of 1.0?mg?L?1 respectively. It suggested that the structure of 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea could be optimized further.

Isothiocyanation of amines using the Langlois reagent

The Langlois reagent was found to be effective for the isothiocyanation of primary amines in the presence of copper iodide and diethyl phosphonate.

Convenient synthesis of benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles with 1 mol% CuCl2·2H2O as catalyst in water

A convenient and efficient procedure for the synthesis of benzo[4,5]thiazolo [2,3-c][1,2,4]triazoles has been developed via a tandem intermolecular C-N bond and intramolecular C-S bond formation sequence from o-bromo-arylisothiocyanates and aroylhydrazides. A series of benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles were provided in excellent overall yields with 1 mol% CuCl2·2H2O/1 mol% 1,10-phenanthroline as the catalyst and water as the solvent. This journal is