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685-87-0

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685-87-0 Usage

Chemical Properties

CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID

Uses

Different sources of media describe the Uses of 685-87-0 differently. You can refer to the following data:
1. Diethyl Bromomalonate is a chemical constituent of the asymmetric cyclopropanation of chalcones. Also used in the preparation of nanaplatforms for NIR imaging-guided photodynamic therapy of cancer cel ls.
2. Diethyl bromomalonate is used in perfumes. It is also used to synthesize other compounds such as barbiturates, artificial flavorings, vitamin B1, and vitamin B6.

Purification Methods

Purify the ester by fractional distillation in a vacuum. IR: max 1800 and 1700cm-1 [Abramovitch Can J Chem 37 1146 1959, Bretschneider & Karpitschka Monatsh Chem 84 1091 1053]. [Beilstein 2 IV 1904.]

Check Digit Verification of cas no

The CAS Registry Mumber 685-87-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,8 and 5 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 685-87:
(5*6)+(4*8)+(3*5)+(2*8)+(1*7)=100
100 % 10 = 0
So 685-87-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H11BrO4/c1-3-11-6(9)5(8)7(10)12-4-2/h5H,3-4H2,1-2H3

685-87-0 Well-known Company Product Price

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  • Alfa Aesar

  • (A10965)  Diethyl bromomalonate, 90+%   

  • 685-87-0

  • 25g

  • 237.0CNY

  • Detail
  • Alfa Aesar

  • (A10965)  Diethyl bromomalonate, 90+%   

  • 685-87-0

  • 50g

  • 365.0CNY

  • Detail
  • Alfa Aesar

  • (A10965)  Diethyl bromomalonate, 90+%   

  • 685-87-0

  • 250g

  • 942.0CNY

  • Detail

685-87-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name DIETHYL BROMOMALONATE

1.2 Other means of identification

Product number -
Other names Propanedioic acid, bromo-, diethyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:685-87-0 SDS

685-87-0Synthetic route

diethyl malonate
105-53-3

diethyl malonate

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

Conditions
ConditionsYield
With bromine In tetrachloromethane for 1h; Heating; Irradiation;100%
Stage #1: diethyl malonate With sodium hydride In dimethyl sulfoxide at 40℃; for 2.5h;
Stage #2: With copper(ll) bromide In dimethyl sulfoxide at 40℃; for 1.5h;
99%
With Cl(CF2)4SO2Br at 10℃; for 10h;98%
diethyl dibromomalonate
631-22-1

diethyl dibromomalonate

EtTe(CH2)3OH
189247-71-0

EtTe(CH2)3OH

A

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

B

2-Bromo-2-ethyl-2λ4-[1,2]oxatellurolane

2-Bromo-2-ethyl-2λ4-[1,2]oxatellurolane

Conditions
ConditionsYield
In dichloromethane for 2h; Ambient temperature;A 95%
B 71%
diethyl dibromomalonate
631-22-1

diethyl dibromomalonate

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 28℃; for 18h; Irradiation; Inert atmosphere;91%
With stannous fluoride In methanol
diethyl malonate
105-53-3

diethyl malonate

A

diethyl dibromomalonate
631-22-1

diethyl dibromomalonate

B

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

Conditions
ConditionsYield
With bromine at 20 - 25℃; for 3h;A 4%
B 87%
diethyl dibromomalonate
631-22-1

diethyl dibromomalonate

A

ethyl tribromoacetate
599-99-5

ethyl tribromoacetate

B

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

Conditions
ConditionsYield
With sodium methylate In tetrahydrofuranA 75%
B n/a
(E)-1-methyl-4-(2-nitroprop-1-en-1-yl)benzene
52287-56-6

(E)-1-methyl-4-(2-nitroprop-1-en-1-yl)benzene

A

1,1,2,2-tetracarboethoxy-ethylene
6174-95-4

1,1,2,2-tetracarboethoxy-ethylene

B

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran for 10h; Ambient temperature;A 40%
B 50%
bromocyane
506-68-3

bromocyane

triethylamine
121-44-8

triethylamine

diethyl malonate
105-53-3

diethyl malonate

A

Diethylcyanamide
617-83-4

Diethylcyanamide

B

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

Conditions
ConditionsYield
In acetone at 20℃;A n/a
B 38%
In acetone at 20℃; von Braun Amine Degradation;
bromocyane
506-68-3

bromocyane

diethyl malonate
105-53-3

diethyl malonate

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

Conditions
ConditionsYield
at 100 - 110℃;
at 100 - 110℃;
ethyl methyl malonate
6186-89-6

ethyl methyl malonate

A

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

B

ethyl methyl bromomalonate
93612-48-7

ethyl methyl bromomalonate

C

dimethyl 2-bromomalonate
868-26-8

dimethyl 2-bromomalonate

Conditions
ConditionsYield
With bromine In tetrachloromethane for 0.5h; Heating;A n/a
B 12.1 g
C n/a
diethyl malonate
105-53-3

diethyl malonate

1(or 3)-bromo-5,5-dimethyl-imidazolidine-2,4-dione

1(or 3)-bromo-5,5-dimethyl-imidazolidine-2,4-dione

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

Conditions
ConditionsYield
With tetrachloromethane; dibenzoyl peroxide
bromine
7726-95-6

bromine

diethyl malonate
105-53-3

diethyl malonate

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

malonic acid diethyl ester (1 mol)

malonic acid diethyl ester (1 mol)

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

Conditions
ConditionsYield
With bromine
diethyl dibromomalonate
631-22-1

diethyl dibromomalonate

A

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

B

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
With iron pentacarbonyl; water In benzene at 80℃;A 40 % Chromat.
B 14 % Chromat.
1,1,3,3-tetramethyl-2-thiourea
2782-91-4

1,1,3,3-tetramethyl-2-thiourea

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

2-(1,3-diethoxy-1,3-dioxopropan-2-yl)-1,1,3,3-tetramethylthiouronium bromide

2-(1,3-diethoxy-1,3-dioxopropan-2-yl)-1,1,3,3-tetramethylthiouronium bromide

Conditions
ConditionsYield
at 20℃; for 12h;100%
In dichloromethane
potassium phthalimide-15N
53510-88-6

potassium phthalimide-15N

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

diethyl <15N>phthalimidomalonate
5680-62-6

diethyl <15N>phthalimidomalonate

Conditions
ConditionsYield
cetyltributylphosphonium bromide In toluene for 20h;100%
Ethyl 5-Thioxopyrrolidine-2-carboxylate
84911-17-1

Ethyl 5-Thioxopyrrolidine-2-carboxylate

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

Diethyl 2-<2-(Ethoxycarbonyl)-5-pyrrolidinylidene>malonate
84911-19-3

Diethyl 2-<2-(Ethoxycarbonyl)-5-pyrrolidinylidene>malonate

Conditions
ConditionsYield
With sodium hydrogencarbonate Eschenmoser coupling reaction;100%
With sodium hydrogencarbonate In dichloromethane for 24h; Heating;42%
Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

1-[[(Z)-6-ethoxy-4-methylene-5-hexenyl]oxy]-4-methoxybenzene
226903-40-8

1-[[(Z)-6-ethoxy-4-methylene-5-hexenyl]oxy]-4-methoxybenzene

diethyl 6-ethoxy-3,6-dihydro-4-[3-(p-methoxyphenoxy)propyl]-2H-thiopyran-2,2-dicarboxylate
226903-45-3

diethyl 6-ethoxy-3,6-dihydro-4-[3-(p-methoxyphenoxy)propyl]-2H-thiopyran-2,2-dicarboxylate

Conditions
ConditionsYield
With sulfur; triethylamine In acetonitrile at 20℃; for 27h; Cycloaddition;100%
Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

ethyl (2S)-5-thioxo-3,4-dihydro-5H-pyrrole-2-carboxylate
80442-95-1

ethyl (2S)-5-thioxo-3,4-dihydro-5H-pyrrole-2-carboxylate

(S)-5-(bis(ethoxycarbonyl)methylidene)pyrrolidine-2-carboxylic acid ethyl ester
675588-09-7

(S)-5-(bis(ethoxycarbonyl)methylidene)pyrrolidine-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane for 48h; Eschenmoser contraction; Heating;100%
With sodium carbonate In dichloromethane for 2.5h; Eschenmoser Sulfide Contraction; Sonication;73%
C25H36O3

C25H36O3

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

diethyl 2-(4-(3-(4-(2-ethyl-2-hydroxybutoxy)-3-methylphenyl)pentan-3-yl)-2-methylphenoxy)malonate

diethyl 2-(4-(3-(4-(2-ethyl-2-hydroxybutoxy)-3-methylphenyl)pentan-3-yl)-2-methylphenoxy)malonate

Conditions
ConditionsYield
With hydrogenchloride; potassium carbonate In water; N,N-dimethyl-formamide for 22h;100%
N-Methylpyrrole
96-54-8

N-Methylpyrrole

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

diethyl 2-(1-methyl-1H-pyrrol-2-yl)malonate

diethyl 2-(1-methyl-1H-pyrrol-2-yl)malonate

Conditions
ConditionsYield
With C18H13NOS; N-ethyl-N,N-diisopropylamine In acetonitrile for 1.66667h; Irradiation;100%
With 2,6-dimethylpyridine for 24h; Irradiation; Inert atmosphere;87%
With N,N-diphenylaminobenzene; 5,5'-bis((2-(trifluoromethyl)phenyl)ethynyl)-2,2'-bithiophene In N,N-dimethyl-formamide at 20℃; for 0.666667h; Irradiation;40 mg
Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

diethyl 2-chloromalonate
14064-10-9

diethyl 2-chloromalonate

Conditions
ConditionsYield
With N-chloro-succinimide In dimethyl sulfoxide at 20℃; for 24h;99.4%
Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

diethyl 2-(2'-nitrophenoxy)malonate
32539-24-5

diethyl 2-(2'-nitrophenoxy)malonate

Conditions
ConditionsYield
Stage #1: 2-hydroxynitrobenzene With potassium hydroxide In ethanol for 0.5h;
Stage #2: Diethyl 2-bromomalonate In N,N-dimethyl-formamide for 16h; Inert atmosphere;
99%
With potassium fluoride In N,N-dimethyl-formamide at 60℃; for 6h; Substitution;70%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

diethyl 2-[(2-nitro-3-pyridyl)oxy]malonate
499787-33-6

diethyl 2-[(2-nitro-3-pyridyl)oxy]malonate

Conditions
ConditionsYield
Stage #1: 3-hydroxy-2-nitropyridine With potassium fluoride In N,N-dimethyl-formamide at 0℃; for 0.5h; Kikelj reaction;
Stage #2: Diethyl 2-bromomalonate In N,N-dimethyl-formamide at 20℃; for 24h;
99%
Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

diethyl bromochloromalonate
81289-78-3

diethyl bromochloromalonate

Conditions
ConditionsYield
With sodium hypochlorite In acetic acid; acetone at 0℃; for 1h;99%
With sodium hypochlorite; acetic acid In acetone at 0℃;98%
Multi-step reaction with 2 steps
1: N-chloro-succinimide / dimethyl sulfoxide / 24 h / 20 °C
2: acetic acid; sodium hypobromide / acetone / 12 h / 0 - 20 °C
View Scheme
2-nitro-4-fluorophenol
394-33-2

2-nitro-4-fluorophenol

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

C13H14FNO7
1225014-16-3

C13H14FNO7

Conditions
ConditionsYield
Stage #1: 2-nitro-4-fluorophenol With potassium hydroxide In ethanol for 1h;
Stage #2: Diethyl 2-bromomalonate In N,N-dimethyl-formamide for 24h; Inert atmosphere;
99%
2-chloro-6-nitrophenol
603-86-1

2-chloro-6-nitrophenol

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

C13H14ClNO7
1225014-20-9

C13H14ClNO7

Conditions
ConditionsYield
Stage #1: 2-chloro-6-nitrophenol With potassium hydroxide In ethanol for 1h;
Stage #2: Diethyl 2-bromomalonate In N,N-dimethyl-formamide for 24h; Inert atmosphere;
99%
(5-chloro-2-hydroxyphenyl)phenylmethanone
85-19-8

(5-chloro-2-hydroxyphenyl)phenylmethanone

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

ethyl 5-chloro-3-phenyl-1-benzofuran-2-carboxylate
27006-00-4

ethyl 5-chloro-3-phenyl-1-benzofuran-2-carboxylate

Conditions
ConditionsYield
Stage #1: (5-chloro-2-hydroxyphenyl)phenylmethanone With potassium carbonate In acetone for 0.5h; Inert atmosphere;
Stage #2: Diethyl 2-bromomalonate In acetone Inert atmosphere; Reflux;
99%
SL 81.0196
61785-35-1

SL 81.0196

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

ethyl 5-chloro-3-(2-chlorophenyl)-1-benzofuran-2-carboxylate
1263152-60-8

ethyl 5-chloro-3-(2-chlorophenyl)-1-benzofuran-2-carboxylate

Conditions
ConditionsYield
Stage #1: SL 81.0196 With potassium carbonate In acetone for 0.5h; Inert atmosphere;
Stage #2: Diethyl 2-bromomalonate In acetone Inert atmosphere; Reflux;
99%
5-Hexen-1-ol
821-41-0

5-Hexen-1-ol

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

diethyl 2-(2-bromo-6-hydroxyhexyl)malonate
1277180-98-9

diethyl 2-(2-bromo-6-hydroxyhexyl)malonate

Conditions
ConditionsYield
With Ir[(dF(CF3)ppy)2(dtbbpy)]PF6; lithium bromide In water; N,N-dimethyl-formamide for 24h; Visible-light irradiation; Inert atmosphere;99%
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; lithium bromide In water; N,N-dimethyl-formamide Inert atmosphere; Irradiation;99%
With 2,6-dimethylpyridine; 4-methoxy-benzaldehyde In acetonitrile at 25℃; for 26h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;99%
ethyl 6-heptenoate
25118-23-4

ethyl 6-heptenoate

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

triethyl 3-bromoheptane-1,1,7-tricarboxylate
1277181-03-9

triethyl 3-bromoheptane-1,1,7-tricarboxylate

Conditions
ConditionsYield
With Ir[(dF(CF3)ppy)2(dtbbpy)]PF6; lithium bromide In water; N,N-dimethyl-formamide for 24h; Visible-light irradiation; Inert atmosphere;99%
N-tert-butoxycarbonylprop-2-en-1-amine
78888-18-3

N-tert-butoxycarbonylprop-2-en-1-amine

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

diethyl 2-(2-bromo-3-((tert-butoxycarbonyl)amino)propyl)malonate
1277180-97-8

diethyl 2-(2-bromo-3-((tert-butoxycarbonyl)amino)propyl)malonate

Conditions
ConditionsYield
With Ir[(dF(CF3)ppy)2(dtbbpy)]PF6; lithium bromide In water; N,N-dimethyl-formamide for 24h; Visible-light irradiation; Inert atmosphere;99%
With C30H26N6Ru(2+)*2Cl(1-); lithium bromide In dimethyl sulfoxide for 24h; Inert atmosphere; Irradiation;99%
With C44H29CuN4O3P(1+)*BF4(1-); lithium bromide In water; N,N-dimethyl-formamide at 20℃; for 20h; Kinetics; Reagent/catalyst; UV-irradiation;89%
ethanol
64-17-5

ethanol

C16H23NO2
1362048-93-8

C16H23NO2

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

diethyl 2-(1-(benzyloxycarbonylamino)-1-ethoxyoctan-2-yl)malonate

diethyl 2-(1-(benzyloxycarbonylamino)-1-ethoxyoctan-2-yl)malonate

Conditions
ConditionsYield
With [Ir(ppy)2(dtbbpy)]PF6; triethylamine In dichloromethane at 20℃; under 760.051 Torr; Inert atmosphere; Irradiation;99%
ethanol
64-17-5

ethanol

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

benzyl N-[(1E)-prop-1-en-1-yl]-carbamate
260967-14-4

benzyl N-[(1E)-prop-1-en-1-yl]-carbamate

diethyl 2-(1-(benzyloxycarbonylamino)-1-ethoxypropan-2-yl)malonate

diethyl 2-(1-(benzyloxycarbonylamino)-1-ethoxypropan-2-yl)malonate

Conditions
ConditionsYield
With [Ir(ppy)2(dtbbpy)]PF6; triethylamine In dichloromethane at 20℃; under 760.051 Torr; for 1h; Inert atmosphere; sunlight; optical yield given as %de;99%
N-tosyl-4-nitrobenzaldimine
13707-46-5

N-tosyl-4-nitrobenzaldimine

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

diethyl 3-(4-nitrophenyl)-1-tosylaziridine-2,2-dicarboxylate
1342891-82-0

diethyl 3-(4-nitrophenyl)-1-tosylaziridine-2,2-dicarboxylate

Conditions
ConditionsYield
With sodium hydride In acetonitrile; mineral oil at 0 - 20℃; Inert atmosphere;99%
With sodium hydride In acetonitrile for 0.283333h; Inert atmosphere;84%
With sodium hydride In acetonitrile; mineral oil at 0 - 20℃; Inert atmosphere;
Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

N-(4-cyanobenzylidene)-p-toluenesulfonamide
143206-01-3

N-(4-cyanobenzylidene)-p-toluenesulfonamide

diethyl 3-(4-cyanophenyl)-1-tosylaziridine-2,2-dicarboxylate
1132667-73-2

diethyl 3-(4-cyanophenyl)-1-tosylaziridine-2,2-dicarboxylate

Conditions
ConditionsYield
With sodium hydride In acetonitrile; mineral oil at 0 - 20℃; Inert atmosphere;99%
With sodium hydride In acetonitrile for 0.233333h; Inert atmosphere;90%
Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

4-methyl-N-[propylidene]benzene-1-sulfonamide
163926-77-0

4-methyl-N-[propylidene]benzene-1-sulfonamide

diethyl 3-ethyl-1-tosylaziridine-2,2-dicarboxylate
1373511-46-6

diethyl 3-ethyl-1-tosylaziridine-2,2-dicarboxylate

Conditions
ConditionsYield
With sodium hydride In acetonitrile; mineral oil at 0 - 20℃; Inert atmosphere;99%
4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

diethyl 2-((4-methoxybenzyl)amino)malonate

diethyl 2-((4-methoxybenzyl)amino)malonate

Conditions
ConditionsYield
Stage #1: 4-methoxy-benzylamine With potassium carbonate In acetonitrile at 20℃; for 2h; Reflux;
Stage #2: Diethyl 2-bromomalonate In acetonitrile at 20℃;
99%
With triethylamine In chloroform Reflux;20%
3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

(R)-diethyl 2-(1-oxo-3-phenylpropan-2-yl)malonate
1085512-00-0

(R)-diethyl 2-(1-oxo-3-phenylpropan-2-yl)malonate

Conditions
ConditionsYield
With 2,6-dimethylpyridine; C21H22N2O2S In N,N-dimethyl-formamide at 15℃; for 18h; Catalytic behavior; Quantum yield; Reagent/catalyst; Solvent; Irradiation; enantioselective reaction;99%
With 2,6-dimethylpyridine; C11H12ClNOPtS2; C14H20N2O In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Irradiation; enantioselective reaction;91%
With 2,6-dimethylpyridine; (2R,5S)-2-tert-butyl-3,5-dimethylimidazolidin-4-one hydrogen chloride; bismuth(III) oxide In N,N-dimethyl-formamide at 20℃; for 1h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Sealed tube; Irradiation; enantioselective reaction;86%
With 2,6-dimethylpyridine; (2R,5S)-2-tert-butyl-3,5-dimethylimidazolidin-4-one trifluoromethanesulfonate In N,N-dimethyl-formamide for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Irradiation; Sealed tube; enantioselective reaction;83%
With 2,6-dimethylpyridine; (2R,5S)-2-tert-butyl-3,5-dimethylimidazolidin-4-one trifluoromethanesulfonate; [Fe(bpy)3]Br2 In N,N-dimethyl-formamide at 25℃; for 16h; Irradiation; enantioselective reaction;78%
Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

2-cinnamoyl-1-methyl-1H-imidazole
99802-91-2

2-cinnamoyl-1-methyl-1H-imidazole

(2R,3S)-diethyl 2-(1-methyl-1H-imidazole-2-carbonyl)-3-phenylcyclopropane-1,1-dicarboxylate

(2R,3S)-diethyl 2-(1-methyl-1H-imidazole-2-carbonyl)-3-phenylcyclopropane-1,1-dicarboxylate

Conditions
ConditionsYield
Stage #1: 2-cinnamoyl-1-methyl-1H-imidazole With C38H38N4O2Rh(1+)*BF4(1-) In chloroform at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: Diethyl 2-bromomalonate With triethylamine In chloroform at 20℃; for 3h; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere; enantioselective reaction;
99%
C18H14N2O

C18H14N2O

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

(2S,3R)-diethyl 2-phenyl-3-(1-phenyl-1H-imidazole-2-carbonyl)cyclopropane-1,1-dicarboxylate

(2S,3R)-diethyl 2-phenyl-3-(1-phenyl-1H-imidazole-2-carbonyl)cyclopropane-1,1-dicarboxylate

Conditions
ConditionsYield
Stage #1: C18H14N2O With C38H38N4O2Rh(1+)*BF4(1-) In chloroform at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: Diethyl 2-bromomalonate With triethylamine In chloroform at 20℃; for 10h; Schlenk technique; Inert atmosphere; enantioselective reaction;
99%
C14H14N2O

C14H14N2O

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

(2R,3S)-diethyl 2-(1-methyl-1H-imidazole-2-carbonyl)-3-(m-tolyl)cyclopropane-1,1-dicarboxylate

(2R,3S)-diethyl 2-(1-methyl-1H-imidazole-2-carbonyl)-3-(m-tolyl)cyclopropane-1,1-dicarboxylate

Conditions
ConditionsYield
Stage #1: C14H14N2O With C38H38N4O2Rh(1+)*BF4(1-) In chloroform at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: Diethyl 2-bromomalonate With triethylamine In chloroform at 20℃; for 10h; Schlenk technique; Inert atmosphere; enantioselective reaction;
99%
C14H14N2O2

C14H14N2O2

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

(2S,3R)-diethyl 2-(4-methoxyphenyl)-3-(1-methyl-1H-imidazole-2-carbonyl)cyclopropane-1,1-dicarboxylate

(2S,3R)-diethyl 2-(4-methoxyphenyl)-3-(1-methyl-1H-imidazole-2-carbonyl)cyclopropane-1,1-dicarboxylate

Conditions
ConditionsYield
Stage #1: C14H14N2O2 With C38H38N4O2Rh(1+)*BF4(1-) In chloroform at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: Diethyl 2-bromomalonate With triethylamine In chloroform at 20℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;
99%

685-87-0Relevant articles and documents

Orienting effect of the cage addends: The case of nucleophilic cyclopropanation of C2-C70(CF3)8

Apenova, Marina G.,Semivrazhskaya, Olesya O.,Borkovskaya, Eugenia V.,Belov, Nikita M.,Ioffe, Ilya N.,Markov, Vitaliy Yu.,Troyanov, Sergey I.,Lukonina, Natalia S.,Sidorov, Lev N.,Goryunkov, Alexey A.

, p. 1370 - 1378 (2015)

C2-C70(CF3)8 was found to be a very promising substrate in the Bingel and the Bingel-Hirsch reactions combining perfect regioselectivity with much higher reactivity compared to its analogs. The reactions with diethyl malonate yield a single isomer of the monoadduct C70(CF3)8[C(CO2Et)2] and a single C2-symmetrical bisadduct C70(CF3)8[C(CO2Et)2]2. The Bingel-Hirsch variation is particularly interesting in that it additionally affords, in a similar regioselective manner, the unexpected alkylated derivatives C70(CF3)8[CH(CO2Et)2]H and C70(CF3)8[C(CO2Et)2][CH(CO2Et)2]H. The novel compounds have been isolated and structurally characterized by means of 1H and 19F NMR spectroscopy as well as single-crystal X-ray diffraction. The mechanistic and regiochemical aspects of the reaction are explained with the aid of DFT calculations. Conventional vs. unconventional: Acceptor-derivatized fullerene substrates can exhibit an enhanced reactivity and regioselectivity in important organic reactions. Bingel and Bingel-Hirsch functionalization of C2-C70(CF3)8 are reported, which affords rapid and LUMO-directed regioselective formation of both conventional cyclopropanated and unusual alkylated products. The mechanistic and regiochemical aspects of the reaction are explained with the aid of the DFT calculations.

Phenyl pyrimidinamine anti-tumor compound as well as preparation method and application thereof

-

Paragraph 0045-0047, (2021/06/06)

The invention belongs to the technical field of medicines, relates to a compound with anti-tumor activity and a specific chemical structure, and particularly relates to a phenyl pyrimidinamine compound as well as a preparation method and application thereof. The structural general formula of the phenyl pyrimidinamine compound is shown in the specification, wherein an R group is a hydrogen atom, a 2-position monosubstituted fluorine atom, or 3-position and 4-position monosubstituted methyl, a fluorine atom, a chlorine atom and a bromine atom. Experimental research shows that the prepared phenyl pyrimidinamine compound shows a good result in an in-vitro anti-tumor activity test, can be used for preparing anti-tumor drugs, and opens up a new way for developing the anti-tumor drugs with an endothelin receptor as a new target. The preparation method provided by the invention is simple and feasible, higher in yield and easy for large-scale production.

Novel Allosteric Inhibitors of Deoxyhypusine Synthase against Malignant Melanoma: Design, Synthesis, and Biological Evaluation

Li, Shuai,Li, Xin-Yang,Li, Yu-Heng,Lin, Qi-Qi,Liu, Kai-Li,Meng, Fan-Hao,Qian, Xin-Hua,Wang, De-Pu,Xue, Wen-Han

, p. 13356 - 13372 (2021/09/20)

Based on the novel allosteric site of deoxyhypusine synthase (DHPS), two series of 30 novel 5-(2-methoxyphenoxy)-2-phenylpyrimidin-4-amine derivatives as DHPS inhibitors were designed and synthesized. Among them, compound8m, with the best DHPS inhibitory potency (IC50= 0.014 μM), exhibited excellent inhibition against melanoma cells, which was superior to that of GC7. Besides, molecular docking and molecular dynamics (MD) simulations further proved that compound8mwas tightly bound to the allosteric site of DHPS. Flow cytometric analysis and enzyme-linked immunosorbent assay (ELISA) showed that compound8mcould inhibit the intracellular reactive oxygen species (ROS) level. Furthermore, by western blot analysis, compound8meffectively activated caspase 3 and decreased the expressions of GP-100, tyrosinase, eIF5A2, MMP2, and MMP9. Moreover, both Transwell analysis and wound healing analysis showed that compound8mcould inhibit the invasion and migration of melanoma cells. In thein vivostudy, the tumor xenograft model showed that compound8meffectively inhibited melanoma development with low toxicity.

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