Diethyl bromomalonate supplier

Name
DIETHYL BROMOMALONATE
EINECS 211-683-1
CAS No. 685-87-0
Article Data49
CAS DataBase
Density 1.452 g/cm³
Solubility Does not mix well with water.
Melting Point -54°C
Formula C₇H₁₁BrO₄
Boiling Point 233.999 °C at 760 mmHg
Molecular Weight 239.066
Flash Point 89.603 °C
Transport Information UN 3265 8/PG 2
Appearance Clear colourless to slightly yellow liquid
Safety 26-36/37/39-45
Risk Codes 34
Molecular Structure
Hazard Symbols C
Synonyms Malonicacid, bromo-, diethyl ester (6CI,7CI,8CI);Propanedioic acid, bromo-, diethylester (9CI);2-Bromomalonic acid diethyl ester;Bromomalonic acid diethylester;Diethyl 2-bromo-1,3-propanedioate;Diethyl 2-bromomalonate;Diethyl2-bromopropanedioate;Diethyl bromomalonate;Diethyl a-bromomalonate;Ethylbromomalonate;NSC 1985;a-Bromomalonic ester;
PSA 52.60000
LogP 0.87610

Synthetic route

: 105-53-3
diethyl malonate

: 685-87-0
Diethyl 2-bromomalonate

Conditions

Conditions	Yield
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%

: 631-22-1
diethyl dibromomalonate

: 189247-71-0
EtTe(CH2)3OH

A: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	A 95% B 71%

...Expand

: 631-22-1
diethyl dibromomalonate

: 685-87-0
Diethyl 2-bromomalonate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 28℃; for 18h; Irradiation; Inert atmosphere;	91%
With stannous fluoride In methanol

: 105-53-3
diethyl malonate

A: 631-22-1
diethyl dibromomalonate

B: 685-87-0
Diethyl 2-bromomalonate

Conditions

Conditions	Yield
With bromine at 20 - 25℃; for 3h;	A 4% B 87%

: 631-22-1
diethyl dibromomalonate

A: 599-99-5
ethyl tribromoacetate

B: 685-87-0
Diethyl 2-bromomalonate

Conditions

Conditions	Yield
With sodium methylate In tetrahydrofuran	A 75% B n/a

: 52287-56-6
(E)-1-methyl-4-(2-nitroprop-1-en-1-yl)benzene

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

B: 685-87-0
Diethyl 2-bromomalonate

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 10h; Ambient temperature;	A 40% B 50%

: 506-68-3
bromocyane

: 121-44-8
triethylamine

: 105-53-3
diethyl malonate

A: 617-83-4
Diethylcyanamide

B: 685-87-0
Diethyl 2-bromomalonate

Conditions

Conditions	Yield
In acetone at 20℃;	A n/a B 38%
In acetone at 20℃; von Braun Amine Degradation;

...Expand

: 506-68-3
bromocyane

: 105-53-3
diethyl malonate

: 685-87-0
Diethyl 2-bromomalonate

Conditions

Conditions	Yield
at 100 - 110℃;
at 100 - 110℃;

: 6186-89-6
ethyl methyl malonate

A: 685-87-0
Diethyl 2-bromomalonate

B: 93612-48-7
ethyl methyl bromomalonate

C: 868-26-8
dimethyl 2-bromomalonate

Conditions

Conditions	Yield
With bromine In tetrachloromethane for 0.5h; Heating;	A n/a B 12.1 g C n/a

...Expand

: 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

: 685-87-0
Diethyl 2-bromomalonate

Conditions

Conditions	Yield
With tetrachloromethane; dibenzoyl peroxide

: 7726-95-6
bromine

: 105-53-3
diethyl malonate

: 685-87-0
Diethyl 2-bromomalonate

malonic acid diethyl ester (1 mol): malonic acid diethyl ester (1 mol)

: 685-87-0
Diethyl 2-bromomalonate

Conditions

Conditions	Yield
With bromine

: 631-22-1
diethyl dibromomalonate

A: 685-87-0
Diethyl 2-bromomalonate

B: 105-53-3
diethyl malonate

Conditions

Conditions	Yield
With iron pentacarbonyl; water In benzene at 80℃;	A 40 % Chromat. B 14 % Chromat.

: 2782-91-4
1,1,3,3-tetramethyl-2-thiourea

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
at 20℃; for 12h;	100%
In dichloromethane

: 53510-88-6
potassium phthalimide-15N

: 685-87-0
Diethyl 2-bromomalonate

: 5680-62-6
diethyl <15N>phthalimidomalonate

Conditions

Conditions	Yield
cetyltributylphosphonium bromide In toluene for 20h;	100%

: 84911-17-1
Ethyl 5-Thioxopyrrolidine-2-carboxylate

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
With sodium hydrogencarbonate Eschenmoser coupling reaction;	100%
With sodium hydrogencarbonate In dichloromethane for 24h; Heating;	42%

: 685-87-0
Diethyl 2-bromomalonate

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

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

Conditions

Conditions	Yield
With sulfur; triethylamine In acetonitrile at 20℃; for 27h; Cycloaddition;	100%

: 685-87-0
Diethyl 2-bromomalonate

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

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

Conditions

Conditions	Yield
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

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
With hydrogenchloride; potassium carbonate In water; N,N-dimethyl-formamide for 22h;	100%

: 96-54-8
N-Methylpyrrole

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
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

: 685-87-0
Diethyl 2-bromomalonate

: 14064-10-9
diethyl 2-chloromalonate

Conditions

Conditions	Yield
With N-chloro-succinimide In dimethyl sulfoxide at 20℃; for 24h;	99.4%

: 685-87-0
Diethyl 2-bromomalonate

: 88-75-5
2-hydroxynitrobenzene

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

Conditions

Conditions	Yield
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%

: 15128-82-2
3-hydroxy-2-nitropyridine

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
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%

: 685-87-0
Diethyl 2-bromomalonate

: 81289-78-3
diethyl bromochloromalonate

Conditions

Conditions	Yield
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

: 394-33-2
2-nitro-4-fluorophenol

: 685-87-0
Diethyl 2-bromomalonate

: 1225014-16-3
C13H14FNO7

Conditions

Conditions	Yield
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%

: 603-86-1
2-chloro-6-nitrophenol

: 685-87-0
Diethyl 2-bromomalonate

: 1225014-20-9
C13H14ClNO7

Conditions

Conditions	Yield
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%

: 85-19-8
(5-chloro-2-hydroxyphenyl)phenylmethanone

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
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%

: 61785-35-1
SL 81.0196

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
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%

: 821-41-0
5-Hexen-1-ol

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
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%

: 25118-23-4
ethyl 6-heptenoate

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
With Ir[(dF(CF3)ppy)2(dtbbpy)]PF6; lithium bromide In water; N,N-dimethyl-formamide for 24h; Visible-light irradiation; Inert atmosphere;	99%

: 78888-18-3
N-tert-butoxycarbonylprop-2-en-1-amine

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
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%

: 64-17-5
ethanol

: 1362048-93-8
C16H23NO2

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
With [Ir(ppy)2(dtbbpy)]PF6; triethylamine In dichloromethane at 20℃; under 760.051 Torr; Inert atmosphere; Irradiation;	99%

...Expand

: 64-17-5
ethanol

: 685-87-0
Diethyl 2-bromomalonate

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

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

Conditions

Conditions	Yield
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%

...Expand

: 13707-46-5
N-tosyl-4-nitrobenzaldimine

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
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;

: 685-87-0
Diethyl 2-bromomalonate

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

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

Conditions

Conditions	Yield
With sodium hydride In acetonitrile; mineral oil at 0 - 20℃; Inert atmosphere;	99%
With sodium hydride In acetonitrile for 0.233333h; Inert atmosphere;	90%

: 685-87-0
Diethyl 2-bromomalonate

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

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

Conditions

Conditions	Yield
With sodium hydride In acetonitrile; mineral oil at 0 - 20℃; Inert atmosphere;	99%

: 2393-23-9
4-methoxy-benzylamine

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
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%

: 104-53-0
3-phenyl-propionaldehyde

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
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%

: 685-87-0
Diethyl 2-bromomalonate

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

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

Conditions

Conditions	Yield
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

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
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

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
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

: 685-87-0
Diethyl 2-bromomalonate

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

Conditions

Conditions	Yield
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%

Diethyl bromomalonate Chemical Properties

Molecule structure of Diethyl bromomalonate (CAS NO.685-87-0):

IUPAC Name: Diethyl 2-bromopropanedioate
Molecular Weight: 239.06384 [g/mol]
Molecular Formula: C₇H₁₁BrO₄
Index of Refraction: 1.467
Molar Refractivity: 45.71 cm³
Molar Volume: 164.6 cm³
Surface Tension: 38.3 dyne/cm
Density: 1.452 g/cm³
Flash Point: 89.6 °C
Enthalpy of Vaporization: 47.07 kJ/mol
Boiling Point: 234 °C at 760 mmHg
Vapour Pressure: 0.0542 mmHg at 25 °C
Sensitive: lachrymatory
XLogP3-AA: 1.8
H-Bond Acceptor: 4
Rotatable Bond Count: 6
Exact Mass: 237.984071
MonoIsotopic Mass: 237.984071
Topological Polar Surface Area: 52.6
Heavy Atom Count: 12
Canonical SMILES: CCOC(=O)C(C(=O)OCC)Br
InChI: InChI=1S/C7H11BrO4/c1-3-11-6(9)5(8)7(10)12-4-2/h5H,3-4H2,1-2H3
InChIKey: FNJVDWXUKLTFFL-UHFFFAOYSA-N
EINECS: 211-683-1
Product Categories: C6 to C7; Carbonyl Compounds; Esters

Diethyl bromomalonate Safety Profile

Hazard Codes: Corrosive C
Risk Statements: 34
R34:Causes burns.
Safety Statements: 26-36/37/39-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 3265 8/PG 2
WGK Germany: 3
F: 19
Hazard Note: Corrosive/Lachrymator
HazardClass: 8
PackingGroup: III

Diethyl bromomalonate Specification

Diethyl bromomalonate (CAS NO.685-87-0) is also named as AI3-01376 ; Bromomalonic acid diethyl ester ; Diethyl 2-bromomalonate ; Ethyl bromomalonate ; Malonic acid, bromo-, diethyl ester ; NSC 1985 ; alpha-Bromomalonic ester ; Propanedioic acid, 2-bromo-, 1,3-diethyl ester ; Propanedioic acid, bromo-, diethyl ester . Diethyl bromomalonate (CAS NO.685-87-0) is clear colourless to slightly yellow liquid.

Product Name

DIETHYL BROMOMALONATE

Synthetic route

Diethyl bromomalonate Chemical Properties

Diethyl bromomalonate Safety Profile

Diethyl bromomalonate Specification

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