5205-39-0

Basic information

• Product Name: ETHYL GLUTARYL CHLORIDE
• Synonyms: ETHYL GLUTARYL CHLORIDE;ETHYL 4-(CHLOROFORMYL)BUTYRATE;GLUTARIC ACID MONOETHYL ESTER CHLORIDE;ethyl 5-chloro-5-oxovalerate;Ethyl glutarylchloride(Eethyl 4-chloro-oxovalerate);Ethyl 4-(chloroformyl)butyrate, Ethyl 5-chloro-5-oxovalerate, Ethyl glutaryl chloride;5-Chloro-5-oxopentanoic acid ethyl ester;5-Chloro-5-oxovaleric acid ethyl ester
• CAS NO: 5205-39-0
• Molecular Formula: C₇H₁₁ClO₃
• Molecular Weight: 178.61
• EINECS: 226-000-2
• Product Categories: Halogen compounds;Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 5205-39-0.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 68-70 °C0.07 mm Hg(lit.)
• Flash Point: 82 °C
• Appearance: /Liquid
• Density: 1.139 g/mL at 20 °C
• Vapor Pressure: 0.0674mmHg at 25°C
• Refractive Index: n20/D 1.443
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in water.
• BRN: 1099817
• CAS DataBase Reference: ETHYL GLUTARYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL GLUTARYL CHLORIDE(5205-39-0)
• EPA Substance Registry System: ETHYL GLUTARYL CHLORIDE(5205-39-0)

Safety Data

• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 9
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 5205-39-0(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow liquid

Uses

Different sources of media describe the Uses of 5205-39-0 differently. You can refer to the following data:
1. Ethyl glutaryl chloride is a main cationic monomer, it can bring quaternary ammonium salt
2. Glutaric acid monoethyl ester chloride may be used as a reagent during the multi-step synthesis of lipidic aminoalcohol and diamine derivatives.

General Description

Glutaric acid monoethyl ester chloride (ethyl glutaryl chloride) is a higher acyl chloride homolog. Its reaction with calix[4]arene to form ester group-containing calix[4]arenes has been reported.

InChI:InChI=1/C7H11ClO3/c1-2-11-7(10)5-3-4-6(8)9/h2-5H2,1H3

Synthetic route

thionyl chloride (7719-09-7) + 5-ethoxy-5-oxopentanoic acid (1070-62-8) → ethyl glutaroyl chloride (5205-39-0)

Conditions	Yield
	68%

glutaric anhydride, (108-55-4) + ethanol (64-17-5) → ethyl glutaroyl chloride (5205-39-0)

Conditions	Yield
(i), (ii) SOCl2; Multistep reaction;
Stage #1: glutaric anhydride,; ethanol Heating; Stage #2: With thionyl chloride

5-ethoxy-5-oxopentanoic acid (1070-62-8) → ethyl glutaroyl chloride (5205-39-0)

Conditions	Yield
With thionyl chloride
With thionyl chloride for 72h;
With phosphorus pentachloride In diethyl ether for 1h; Ambient temperature;

monoethyl glutarate → ethyl glutaroyl chloride (5205-39-0)

Conditions	Yield
With thionyl chloride; diethyl ether

potassium salt of monoethyl glutarate → ethyl glutaroyl chloride (5205-39-0)

Conditions	Yield
With thionyl chloride; diethyl ether

ethyl glutaroyl chloride (5205-39-0) + {5-chloro-2-[(2,2-dimethylpropyl)amino]phenyl}(2-chlorophenyl)methanol (152906-79-1) → ethyl 5-[{4-chloro-2-[(2-chlorophenyl)(hydroxy)methyl]-phenyl}(2,2-dimethylpropyl)amino]-5-oxopentanoate (1292849-83-2)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane at 20℃; for 2h; Cooling with ice;	100%

ethyl glutaroyl chloride (5205-39-0) + (S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride (101403-24-1) → (S)-ethyl 5-((5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)(propyl)amino)-5-oxopentanoate (1403822-88-7)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	99%

ethyl glutaroyl chloride (5205-39-0) + 2-Naphthalenethiol (91-60-1) → 4-<(Naphthalen-2-ylthio)carbonyl>butylcarboxylic acid ethyl ester

Conditions	Yield
With pyridine In benzene at 90℃; for 0.5h;	98%

ethyl glutaroyl chloride (5205-39-0) + 1-hexynylzinc chloride (65960-05-6) → 5-oxo-undec-6-ynoic acid ethyl ester (473611-24-4)

Conditions	Yield
In tetrahydrofuran at -78 - 0℃; for 1h;	98%

ethyl glutaroyl chloride (5205-39-0) + 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (14812-60-3) → 5-Oxo-5-(4,4,5,5-tetramethyl-2-oxo-2λ5-[1,3,2]dioxaphospholan-2-yl)-pentanoic acid ethyl ester (108429-31-8)

Conditions	Yield
at 20 - 35℃;	97%

ethyl glutaroyl chloride (5205-39-0) + amino-2 bis(ethoxycarbonylamino)-4,4' biphenyle (71857-96-0) → glutaramate d'ethyle (129138-92-7)

Conditions	Yield
In chlorobenzene Heating;	96%

ethyl glutaroyl chloride (5205-39-0) + 4,4,5,5-tetramethyl<1,3,2>dioxaphospholane-2-oxide (16352-18-4) + 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (14812-60-3) → 5-Hydroxy-5,5-bis-(4,4,5,5-tetramethyl-2-oxo-2λ5-[1,3,2]dioxaphospholan-2-yl)-pentanoic acid ethyl ester (108429-12-5)

Conditions	Yield
at 80℃; for 6h;	96%

ethyl glutaroyl chloride (5205-39-0) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 4-(2-Benzoyl-phenylcarbamoyl)-butyric acid ethyl ester (144076-42-6)

Conditions	Yield
With pyridine In dichloromethane Ambient temperature;	95%

ethyl glutaroyl chloride (5205-39-0) + 1'-(3-aza-spiro[5.5]undecane-9-carbonyl)-[4,4']bipiperidinyl-1-carboxylic acid benzyl ester → 1'-[3-(4-ethoxycarbonyl-butyryl)-3-aza-spiro[5.5]undecane-9-carbonyl]-[4,4']bipiperidinyl-1-carboxylic acid benzyl ester (352348-34-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane	92%

ethyl glutaroyl chloride (5205-39-0) + 4-(1-oxo-2,8-diazaspiro[4.5]dec-2-yl)benzonitrile (685544-34-7) → 5-[2-(4-cyanophenyl)-1-oxo-2,8-diazaspiro[4.5]dec-8-yl]-5-oxopentanoic acid ethyl ester (685544-38-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h;	92%

ethyl glutaroyl chloride (5205-39-0) + 2-phenylaniline (90-41-5) → N-(biphenylyl-2) glutaramate d'ethyle (127563-33-1)

Conditions	Yield
In diethyl ether at 25℃;	90%

ethyl glutaroyl chloride (5205-39-0) + butyl magnesium bromide (693-04-9) → Ethyl 5-oxononanoate (24071-99-6)

Conditions	Yield
Stage #1: butyl magnesium bromide With tributylphosphine In tetrahydrofuran at 20℃; Stage #2: ethyl glutaroyl chloride In tetrahydrofuran at -40℃; for 0.333333h;	90%

ethyl glutaroyl chloride (5205-39-0) + [13C]methyl iodide (4227-95-6) → Ethyl (6-13C)-5-oxohexanoate (128428-65-9)

Conditions	Yield
With copper(l) iodide; lithium In diethyl ether	90%

ethyl glutaroyl chloride (5205-39-0) + N-methoxylamine hydrochloride (593-56-6) → 4-Methoxycarbamoyl-butyric acid ethyl ester

Conditions	Yield
With potassium carbonate In water; ethyl acetate at 0℃; for 2h;	89%

ethyl glutaroyl chloride (5205-39-0) + BuMnCl (88626-90-8) → Ethyl 5-oxononanoate (24071-99-6)

Conditions	Yield
In tetrahydrofuran at -10 - 20℃; for 1.5h;	88%

ethyl glutaroyl chloride (5205-39-0) + 2-Benzenesulfonylmethyl-cyclohex-2-enol (107473-12-1) → C20H26O6S (1309773-34-9)

Conditions	Yield
With pyridine In dichloromethane	88%

ethyl glutaroyl chloride (5205-39-0) + 4,4'-dinitro-2-biphenylamine (51787-75-8) → (dinitro-4,4' biphenylyl-2)glutaramate d'ethyle (129138-80-3)

Conditions	Yield
In chlorobenzene Heating;	87%

ethyl glutaroyl chloride (5205-39-0) + (trimethylsilyl)methylmagnesium chloride (13170-43-9) → ethyl 5-oxo-6-trimethylsilylhexanoate (136578-43-3)

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at -40℃; for 1.5h;	86%

ethyl glutaroyl chloride (5205-39-0) + 3β-hydroxy-28-lupanal (911140-88-0) → 3β-3-(mono-ethylglutaryloxy)-lupan-28-al

Conditions	Yield
With pyridine; dmap at 20℃; for 48h;	86%

ethyl glutaroyl chloride (5205-39-0) + 3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole (2199-44-2) → ethyl 5-<5-(ethoxycarbonyl)-2,4-dimethylpyrrol-3-yl>-5-oxopentanoate (68500-90-3)

Conditions	Yield
With tin(IV) chloride In dichloromethane at 0℃;	84%
With tin(ll) chloride In dichloromethane at 0℃; for 1.5h;	84.1%

ethyl glutaroyl chloride (5205-39-0) + glycine ethyl ester hydrochloride (623-33-6) → ethyl N-(ethoxyglutaryl)glycinate (88889-09-2)

Conditions	Yield
With triethylamine In dichloromethane 1.) 2h; 2.) reflux, 2 h;	83%

ethyl glutaroyl chloride (5205-39-0) + (phenylethynyl)zinc chloride (13984-49-1) → ethyl 5-oxo-7-phenylhept-6-ynoate (473611-23-3)

Conditions	Yield
In tetrahydrofuran at -78 - 0℃; for 1h;	82%

ethyl glutaroyl chloride (5205-39-0) + (E)-1-(4-hydroxyphenyl)-2-nitroethene (22568-49-6) → ethyl 4-<(E)-2-nitroethenyl>phenyl glutarate (142728-07-2)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane for 6.5h; Ambient temperature;	80%

ethyl glutaroyl chloride (5205-39-0) + methylmagnesium bromide (75-16-1) → ethyl 5-oxohexanoate (13984-57-1)

Conditions	Yield
Stage #1: methylmagnesium bromide With tributylphosphine In tetrahydrofuran at 20℃; Stage #2: ethyl glutaroyl chloride In tetrahydrofuran at -40℃; for 0.333333h;	80%
With copper(l) iodide In tetrahydrofuran at -78 - 20℃; Inert atmosphere;

ethyl glutaroyl chloride (5205-39-0) + 2-(1H-indol-5-yl)-N-{phenyl[2-(piperidin-1-yl)phenyl]methyl}acetamide → ethyl 5-oxo-5-{5-[({phenyl[2-(piperidin-1-yl)phenyl]methyl}carbamoyl)methyl]-1H-indol-3-yl}pentanoate

Conditions	Yield
Stage #1: ethyl glutaroyl chloride With aluminum (III) chloride In dichloromethane at 0℃; for 0.5h; Stage #2: 2-(1H-indol-5-yl)-N-{phenyl[2-(piperidin-1-yl)phenyl]methyl}acetamide In dichloromethane at 0 - 20℃; for 53h;	80%

ethyl glutaroyl chloride (5205-39-0) + (3-methylbutyl)magnesium bromide (4548-78-1) → ethyl 8-methyl-5-oxononanoate

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at -78 - 20℃; Schlenk technique;	78%

ethyl glutaroyl chloride (5205-39-0) + 2-chloro-7-ethoxy-3-(3-(4-iodophenyl)-4,5-dihydro-1H-pyrazol-5-yl)quinoline → ethyl 5-(5-(2-chloro-7-ethoxyquinolin-3-yl)-3-(4-iodophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-5-oxopentanoate

Conditions	Yield
Stage #1: 2-chloro-7-ethoxy-3-(3-(4-iodophenyl)-4,5-dihydro-1H-pyrazol-5-yl)quinoline With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.25h; Stage #2: ethyl glutaroyl chloride In dichloromethane at 20℃; for 12h;	78%
Stage #1: 2-chloro-7-ethoxy-3-(3-(4-iodophenyl)-4,5-dihydro-1H-pyrazol-5-yl)quinoline With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.25h; Stage #2: ethyl glutaroyl chloride In dichloromethane at 20℃; for 12h;	78%

ethyl glutaroyl chloride (5205-39-0) + 2-(phenylsulfonylmethyl)phenol (1309773-29-2) → C20H22O6S (1309773-43-0)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃;	73%

ethyl glutaroyl chloride (5205-39-0) + 2,4,4'-trihydroxy deoxybenzoin (17720-60-4) → 2-[3-(Ethoxycarbonyl)propyl]-7,4'-dihydroxyisoflavone

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In acetone for 25h; Cyclization; Heating;	71%

Upstream product

• 108-55-4 glutaric anhydride, 
• 64-17-5 ethanol 
• 7719-09-7 thionyl chloride 
• 1070-62-8 5-ethoxy-5-oxopentanoic acid 

Downstream Products

• 66035-85-6 ethyl 5-oxo-5-(piperidin-1-yl)pentanoate 
• 101448-65-1 7-(1-methyl-2,6-dioxo-cyclohexyl)-5-oxo-heptanoic acid ethyl ester 
• 7508-13-6 5-(3,4-dimethyl-phenyl)-5-oxo-valeric acid 
• 854859-01-1 5-(4-methylsulfanyl-phenyl)-5-oxo-valeric acid ethyl ester 
• 858814-74-1 5-(4-cyclopentyl-phenyl)-5-oxo-valeric acid ethyl ester 
• 16093-16-6 5-(2,3,4-trimethoxy-phenyl)-5-oxo-pentanoic acid 
• 22668-36-6 ethyl 5-oxopentanoate 
• 101577-33-7 ethyl 5-(4-(tert-butyl)phenyl)-5-oxopentanoate 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 100379-51-9 4-(amino-anilino-[1,3,5]triazin-2-yl)-butyric acid 
• 100950-64-9 4-(amino-anilino-[1,3,5]triazin-2-yl)-butyric acid ethyl ester 
• 93044-03-2 2-methyl-3-oxo-heptanedioic acid diethyl ester 
• 102020-84-8 4-<4-Cyclohexyl-benzoyl>-buttersaeure-aethylester 
• 5205-40-3 5-Oxo-octansaeure-ethylester 

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