1117-71-1

Basic information

• Product Name: Methyl 4-bromocrotonate
• Synonyms: methylbromocrotonate;METHYL 4-BROMOCROTONATE, TECH., 85%;Methyl 4-bromocrotonate, pract., 85%;2-Butenoic acid, 4-bromo-, methyl ester;methyl 4-bromocrotonate (4-bromocrotonic acid methyl ester);Methyl-4-bromocrotonate(min.85%trans);Methyl-4-bromocrotonate, 95 % (min. 90 % trans);Methyl-4-bromocrotonate, 96 % (min. 97 % trans)
• CAS NO: 1117-71-1
• Molecular Formula: C₅H₇BrO₂
• Molecular Weight: 179.01
• EINECS: 214-251-0
• Product Categories: C2 to C5;Carbonyl Compounds;Esters
• Mol File: 1117-71-1.mol

Chemical Properties

• Boiling Point: 83-85 °C13 mm Hg(lit.)
• Flash Point: 197 °F
• Appearance: Clear yellow/Liquid
• Density: 1.522 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.358mmHg at 25°C
• Refractive Index: n20/D 1.501
• Storage Temp.: 2-8°C
• Water Solubility: Slightly soluble in water.
• BRN: 1745755
• CAS DataBase Reference: Methyl 4-bromocrotonate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-bromocrotonate(1117-71-1)
• EPA Substance Registry System: Methyl 4-bromocrotonate(1117-71-1)

Safety Data

• Hazard Codes: Xi,C
• Statements: 37/38-41-34-20/21/22
• Safety Statements: 26-39-45-36/37/39
• RIDADR: 3265
• WGK Germany: 3
• RTECS: GQ3120000
• F: 8-9
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1117-71-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 4-bromocrotonate is used as a synthetic intermediate for the development of irreversible inhibitors of EGFR and HER-2 tyrosine kinases. These inhibitors possess enhanced antitumor activities, making them essential in the creation of novel therapeutic agents for the treatment of various cancers.
Used in Chemical Synthesis:
As a synthetic intermediate, Methyl 4-bromocrotonate is employed in the synthesis of a wide range of chemical compounds. Its versatility in chemical reactions allows researchers and chemists to explore its potential in creating new molecules with specific applications across different industries.

InChI:InChI=1/C5H7BrO2/c1-8-5(7)3-2-4-6/h2-3H,4H2,1H3/b3-2-

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 
• 7789-60-8 phosphorus tribromide 
• 13991-36-1 4-bromocrotonic acid 
• 29576-13-4 methyl 4-hydroxy-2-butenoate 
• 3724-65-0 2-butenoic acid 
• 100038-62-8 methyl 4-(phenylseleno)-2(E)-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

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.

Electrochemical Conjugate Additions of the Allyl Groups in Substituted Allyl Halides to α,β-Unsaturated Esters

Electrolysis of allyl halides and diethyl fumarate (2) in N,N-dimethylformamide containing 0.2 M tetraethylammonium tosylate gave a conjugate addition product, ethyl 3-(ethoxycarbonyl)-5-hexenoate, in a moderate yield.The electrochemical reaction of 1-chloro-3-methyl-2-butene (4) with 2, that of allyl chloride 4 with methyl crotonate (6), and that of methyl 4-halo-2-butenoate with 2 likewise gave the corresponding conjugate addition products, ethyl 3-(ethoxycarbonyl)-6-methyl-5-heptenoate, methyl 3,4,4-trimethyl-5-hexenoate, and ethyl 3-(ethoxycarbonyl)-4-(methoxycarbonyl)-5-hexenoate, respectively.The addition reaction of 4 to 2 takes place at the α-carbon terminus of 4 exclusively, whereas the addition of 4 to 6 at the γ-carbon terminus of 4 .These regioselectivities of the additions and pathways of the reactions are discussed.

The total synthesis of the oxopolyene macrolide RK-397

It works both ways: The convergent total synthesis of the oxopolyene macrolide RK-397 utilizes remote asymmetric induction and a two-directional chain synthesis to prepare the polyol portion of the molecule, as well as a cross-metathesis reaction of a trienal with a terminal alkene to append the polyene to the polyol. (Chemical Equation Presented).

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.

Chlorobenzene-pyridine compounds and application thereof

The invention relates to chlorobenzene-pyridine compounds and an application thereof. The compounds can be used for preparing a Smoothened protein inhibitor and a drug for resisting adenocarcinoma andesophagus cancer and have the structure in the general formula (I) shown in the description, wherein X is selected from the structure shown in the description, R1 is selected from H or the structureshown in the description, and R2 is selected from the structure shown in the description.

QUINAZOLINE DERIVATIVE, PREPARATION METHOD THEREFOR, AND PHARMACEUTICAL COMPOSITION AND APPLICATION THEREOF

Disclosed are a quinazoline derivative, a preparation method therefor, and a pharmaceutical composition and an application thereof. The present invention provides a compound represented by general formula I, a stereoisomer thereof and a pharmaceutical acceptable salt or a solvate thereof. The quinazoline derivative of the present invention has a unique chemical structure, is characterized by irreversibly inhibiting EGFR tyrosine kinase, has high biological activity, apparently improves the inhibiting effect on the EGFR tyrosine kinase, has quite strong tumor inhibiting effect on tumor cells and a transplantation tumor pathological model of animal tumors, and has good market developing prospects.

Oxoindole spiro-compound based on allyl sulfide ylide serving as C3 synthon and synthesis method thereof

The invention relates to an oxoindole spiro-compound based on allyl sulfide ylide serving as a C3 synthon. The general chemical molecular formula is CHO, wherein m, n and x are respectively an integer of 1-10; the molecule has a structure as shown below in the specification; R is methyl, ethyl, acetyl, methylethyl ether, benzyl or di-tert-butyl dicarbonate; R is hydroxyl, methoxyl or ethoxyl; and R is 5-F, 5-Br, 5-Cl, 5-CH3, 5-OCH3, 6-Cl, 6-Br, 6-OCH3, 7-CH3, 7-Cl or 7-Br. The invention has the following advantages: through the characteristics of a tandem reaction, the method achieves the purpose of synthesizing the target product through one step, obviously improves the reaction efficiency, saves the reaction time and simplifies the reaction step, thereby providing a brand new method and idea for a trisubstituted five-element oxide spiro-compound, and providing a certain reference value for synthesis of similar compounds.

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.

Geminal silicon/zinc reagent as an equivalent of difluoromethylene bis-carbanion

A new difluorinated reagent, [difluoro(trimethylsilyl)methyl]zinc bromide, bearing C-Zn and C-Si bonds is described. The reagent is conveniently prepared by cobalt-catalyzed halogen/zinc exchange. It can be coupled with two different C-electrophiles in a stepwise manner (with allylic halides for C-Zn bond and aldehydes for C-Si bond) affording products containing a difluoromethylene fragment.

Synthesis and herbicidal activity of diphenyl ether derivatives containing unsaturated carboxylates

A series of novel diphenyl ether derivatives containing unsaturated carboxylates were designed and synthesized. Their structures were identified by 1H nuclear magnetic resonance and elemental analyses. The bioassays indicated that the compounds 5b and 5c exhibited good herbicidal activities against velvetleaf at a concentration of 30-40 g/hm2. The relationship between structure and herbicidal activity was also discussed. Among unsaturated carboxylates group, butenoate is the most promising one. Amonst them, 4-ethoxy-4-oxobutenyl 5-(2-chloro-4-(trifluoromethyl)phenoxy)-2- nitrobenzoate 5b was identified as the most promising candidate due to its high protoporphyrinogen IX oxidase inhibition effect (pI50 = 6.64) and good herbicidal activity against broadleaf weeds with selectivity to soybean and low toxicity to mammals.