6000-00-6

Basic information

• Product Name: METHYL 4-BROMOCROTONATE
• Synonyms: (E)-4-Bromo-but-2-enoicacidmethylester;TRANS-METHYL 4-BROMO-2-BUTENOATE, STAB.;trans-Methyl-4-bromocrotonate, 97 %;(E)-4-Bromo-2-butenoic acid methyl ester;Methyl (E)-4-bromo-2-butenoate;Methyl trans-4-bromocrotonate 97%;Methyl (2E)-4-bromobut-2-enoate;(2E)-4-Bromo-2-butenoic acid methyl ester
• CAS NO: 6000-00-6
• Molecular Formula: C₅H₇BrO₂
• Molecular Weight: 179.01
• EINECS: 214-251-0
• Mol File: 6000-00-6.mol
• Article Data: 18

Chemical Properties

• Melting Point: 83-85℃
• Boiling Point: 83-85 °C13 mm Hg(lit.)
• Flash Point: 197 °F
• Appearance: /
• Density: 1.522 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.501
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• BRN: 1745755
• CAS DataBase Reference: METHYL 4-BROMOCROTONATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-BROMOCROTONATE(6000-00-6)
• EPA Substance Registry System: METHYL 4-BROMOCROTONATE(6000-00-6)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41-36/37/38
• Safety Statements: 26-39
• WGK Germany: 3
• RTECS: GQ3120000
• F: 8-9
• Hazardous Substances Data: 6000-00-6(Hazardous Substances Data)

Usage

Description

METHYL 4-BROMOCROTONATE, also known as Methyl trans-4-bromo-2-butenoate, is a light yellow liquid with significant applications in the field of organic chemistry. It is primarily utilized as a key intermediate in the synthesis of various organic compounds, including benzoxepines, benzopyrans, and L-α-amino [4,5-3H]adipic acid.

Uses

Used in Pharmaceutical Industry:
METHYL 4-BROMOCROTONATE is used as a synthetic intermediate for the production of highly substituted benzoxepines and benzopyrans, which are important compounds in the development of pharmaceuticals. These compounds have potential applications in the treatment of various medical conditions due to their unique chemical structures and properties.
Used in Chemical Synthesis:
METHYL 4-BROMOCROTONATE is used as a reagent in the synthesis of several organic compounds, such as dimethoxy ketals and ketones. It plays a crucial role in the electrochemical oxidative decarboxylation of malonic acids, a process that is essential for the production of various chemicals with diverse applications.
Used in Research and Development:
METHYL 4-BROMOCROTONATE is also used in research and development laboratories for the synthesis of novel compounds and the exploration of new chemical reactions. Its unique properties make it a valuable tool for scientists working in the fields of organic chemistry and materials science.

Upstream product

• 67-56-1 methanol 
• 60-29-7 diethyl ether 
• 99848-36-9 Methyl 2-methoxycyclopropanecarboxylate 
• 124-41-4 sodium methylate 
• 56-23-5 tetrachloromethane 
• 623-43-8 crotonic acid methyl ester 
• 3699-18-1 N-bromoglutarimide 
• 623-43-8 methyl crotonate 
• 5837-73-0 methyl 2-hydroxybut-3-enoate 
• 71-43-2 benzene 
• 7789-60-8 phosphorus tribromide 
• 13991-36-1 4-bromocrotonic acid 
• 3724-65-0 2-butenoic acid 
• 29576-13-4 methyl 4-hydroxy-2-butenoate 

Downstream Products

• 90035-36-2 4-[oxy-(4-dimethylamino-phenyl)-imino]-trans-crotonic acid ethyl ester 
• 101723-21-1 (E)-methyl 5,5-diphenylpenta-2,4-dienoate 
• 24196-43-8 5t-mesityl-penta-2t,4-dienoic acid methyl ester 
• 37836-28-5 (2E,4E,6E)-5-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienoic acid 
• 108715-27-1 5t-(2,4,5-trimethoxy-phenyl)-penta-2t,4-dienoic acid methyl ester 
• 7478-68-4 4-(1,2,3,4-tetrahydro-[1]phenanthryl)-butyric acid 
• 91058-69-4 4-(2,3,4,6-tetraiodo-phenoxy)-trans-crotonic acid methyl ester 
• 100976-73-6 5t-(3-acetoxy-4-methoxy-phenyl)-penta-2t,4-dienoic acid methyl ester 
• 121642-65-7 4-(1-hydroxy-2-methyl-cyclohexyl)-trans-crotonic acid methyl ester 
• 54238-27-6 methyl (E)-4-(1,3-dioxoisoindolin-2-yl)but-2-enoate 
• 13991-36-1 4-bromocrotonic acid 
• 2367-25-1 4-fluoro-trans-crotonic acid methyl ester 
• 38651-67-1 4-(1-hydroxy-cyclohexyl)-crotonic acid methyl ester 
• 56949-94-1 2-(α-hydroxy-benzyl)-but-3-enoic acid methyl ester 

Relevant articles and documents

Ruthenium-catalyzed enantioselective C-H functionalization: A practical access to optically active indoline derivatives

Ru(II)-catalyzed enantioselective C-H activation/hydroarylation has been developed for the first time, allowing for highly enantioselective synthesis of indoline derivatives via catalytic C-H activation. Commercially available Ru(II) arene complexes and chiral α-methylamines were employed as highly enantioselective catalysts. Based on a sterically rigidified chiral transient directing group, multisubstituted indolines were produced in up to 92% yield with 96% ee. Further transformation of the resulting 4-formylindoline enables access to an optically active tricyclic compound that is of potential biological and pharmaceutical interest.

Pyrazolopyrimidine derivative, preparation method, pharmaceutical composition and application

The invention discloses a pyrazolopyrimidine derivative, a preparation method, a pharmaceutical composition and application. The invention provides the pyrazolopyrimidine derivative as shown in a formula I and stereoisomer or solvate or pharmaceutically acceptable salts or active metabolite or prodrug thereof. The pyrazolopyrimidine derivative as shown in the formula I has good inhibitory activity on Bruton's tyrosine kinase (Btk) and particularly has good in vitro and in vivo inhibitory activity on growth of tumor cells, and a good marketization prospect is achieved. Please see the formula I in the description.

Tethered aminohydroxylation: Synthesis of the β-amino acid of microsclerodermins A and B

The utility of the tethered aminohydroxylation (TA) has been demonstrated by synthesis of the complex β-amino acid residue of microsclerodermins A and B. The TA provided a regio- and stereoselective functionalization of a complex homoallylic alcohol. The route includes late-stage introduction of the aliphatic side chain via a cuprate addition and cross metathesis, a tactic designed to render the synthesis applicable to other microsclerodermins.