58304-65-7

Basic information

• Product Name: 1-Chloroisobutyl propionate
• Synonyms: 1-chloroisobutyl propionate;PROPIONIC ACID-1-CHLOROISOBUTYL;1-CHLOROISOBUTYL PROPIONATE,85+%;1-Chloro-2-Methylpropyl Propanoate;1-Chloroisobutyl propionate (Technical Grade)
• CAS NO: 58304-65-7
• Molecular Formula: C₇H₁₃ClO₂
• Molecular Weight: 164.63
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 58304-65-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 166.7°C
• Flash Point: 56°C
• Appearance: /
• Density: 1.030
• Vapor Pressure: 1.77mmHg at 25°C
• Refractive Index: 1.427
• Storage Temp.: 2-8°C
• Solubility: Chloroform
• CAS DataBase Reference: 1-Chloroisobutyl propionate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloroisobutyl propionate(58304-65-7)
• EPA Substance Registry System: 1-Chloroisobutyl propionate(58304-65-7)

Safety Data

• Hazardous Substances Data: 58304-65-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 58304-65-7 differently. You can refer to the following data:
1. Intermediate in the preparation of Fosinopril
2. Intermediate in the preparation of Fosinopril (F727800) derivatives.

InChI:InChI=1/C7H13ClO2/c1-4-6(9)10-7(8)5(2)3/h5,7H,4H2,1-3H3

Synthetic route

propionyl chloride (79-03-8) + isobutyraldehyde (78-84-2) → propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7)

Conditions	Yield
at 0 - 5℃; for 4h;	38%
at 0 - 5℃; for 4h; Inert atmosphere;	38%
With zinc(II) chloride at -20 - 20℃; for 18h;	2.7%

vemurafenib + propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) → 1-(5-(4-chlorophenyl)-3-(2,6-difluoro-3-(propylsulfonamido)benzoyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)-2-methylpropyl propionate (1567346-91-1)

Conditions	Yield
With tetrabutylammomium bromide; potassium hydroxide In N,N-dimethyl-formamide at 10℃; for 3.5h;	45%
Stage #1: vemurafenib With potassium hydroxide In N,N-dimethyl-formamide at 10℃; for 0.166667h; Stage #2: propanoic acid,1-chloro-2-methylpropyl ester With tetrabutylammomium bromide In N,N-dimethyl-formamide at 10℃; for 3h;	45%

propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) + (S)-3-(((tert-butoxycarbonyl)amino)methyl)-5-methylhexanoic acid (649748-09-4) → (S)-3-(tert-butoxycarbonylamino-methy)-5-methyl-hexanoic acid 2-methyl-1-propionyloxy-propyl ester (1026789-39-8)

Conditions	Yield
Stage #1: (S)-3-(((tert-butoxycarbonyl)amino)methyl)-5-methylhexanoic acid With caesium carbonate In methanol at 20℃; for 4h; Stage #2: propanoic acid,1-chloro-2-methylpropyl ester In N,N-dimethyl-formamide at 50℃; for 5h;	40%
Stage #1: (S)-3-(((tert-butoxycarbonyl)amino)methyl)-5-methylhexanoic acid With caesium carbonate In methanol at 20℃; for 4h; Stage #2: propanoic acid,1-chloro-2-methylpropyl ester In N,N-dimethyl-formamide at 50℃; for 5h;	40%

(2-(((4-(1,3-Dihydro-1-oxo-2H-isoindol-2-yl)butyl)-hydroxyphosphinyl)methyl)-4-phenylbutanoyl)-L-leucine N-phenylamide + Å molecular sieves + propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) + tetrahexylammonium iodide (2138-24-1) → (2-(((4-(1,3-Dihydro-1-oxo-2H-isoindol-2-yl)butyl)(2-methyl-1-(1-oxopropoxy) propoxy)phosphinyl)methyl)-4-phenylbutanoyl)-L-leucine N-phenylamide

Conditions	Yield
	32%

propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) + [3-[acetyl(phenylmethoxy)amino]propyl]phosphonic acid (581106-29-8) → [3-[acetyl(phenylmethoxy)amino]propyl]-phosphonic acid bis[2-methyl-1-(1-oxopropoxy)propyl] ester (581106-36-7)

Conditions	Yield
With triethylamine; sodium iodide In various solvent(s) at 60℃; for 6h;	10%
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; triethylamine; sodium iodide at 60℃; for 6h;

propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) + 2-Butyl-6-ethoxy-3-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]oxy]quinoxaline-5-carboxylic acid (150368-48-2) → 2-methyl-1-(1-oxopropoxy)propyl-2-butyl-6-ethoxy-3-<<2'-1H-tetrazol-5-yl<1,1'-biphenyl>-4-yl>oxy>-5-quinoxalinecarboxylate (150368-49-3)

Conditions	Yield
With 4 A molecular sieve; silver(l) oxide 1.) THF, RT, 5 min, 2.) THF, 65 deg C, 18 h; Yield given. Multistep reaction;

propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) + ethyl N-[2-(phosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionate (147923-09-9) → Ethyl N-{2-[di-(α-propionyloxyisobutyl)-phosphonomethylamino]-3-(4-biphenylyl)-propionyl}-3-aminopropionate (147861-87-8)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; 1,8-diazabicyclo-[5,4,0]-undecane; sodium iodide In acetonitrile at 75℃; for 2h;

propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) → 2-ethyl-4,4-dimethyl-1,3-dioxolanium hexachloroantimonate

Conditions	Yield
With antimonypentachloride Yield given;
With antimonypentachloride In dichloromethane at -15℃; for 0.166667h; Yield given;

propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) + C18H30O6PS(3-)*3Ag(1+) → Potassium; (5E,9E)-1-[bis-(2-methyl-1-propionyloxy-propoxy)-phosphoryl]-6,10,14-trimethyl-pentadeca-5,9,13-triene-1-sulfonate

Conditions	Yield
With 2,4,6-trimethyl-pyridine; potassium hydrogencarbonate In dichloromethane

propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) + C16H16O7PS(3-)*3Ag(1+) → Potassium; 1-[bis-(2-methyl-1-propionyloxy-propoxy)-phosphoryl]-4-(3-phenoxy-phenyl)-butane-1-sulfonate

Conditions	Yield
With 2,4,6-trimethyl-pyridine In dichloromethane

6-(Butoxy)-2-butyl-3-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]oxy]quinoxaline-5-carboxylic acid (150368-60-8) + propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) + sodium hydrogencarbonate (144-55-8) → 2-Butyl-6-(butyloxy)-3-[[2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]oxy]-5-quinoxalinecarboxylic acid, 2-methyl-1-(1-oxopropoxy)propyl ester

Conditions	Yield
With sodium bicarbonate; silica gel In tetrahydrofuran; methanol

propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) + [Hydroxy-(4-phenylbutyl)phosphinyl]acetic acid,phenylmethyl ester (87460-09-1) → [[2-Methyl-1-(1-oxopropoxy)propoxy](4-phenylbutyl)phosphinyl]acetic acid

Conditions	Yield
With 4-methyl-morpholine; sodium hydrogencarbonate; palladium In (methyl)isobutyl ketone; water; toluene

BOC-glycine (4530-20-5) + propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) → C14H25NO6 (1616274-54-4)

Conditions	Yield
Stage #1: BOC-glycine With triethylamine In ethyl acetate at 20℃; for 0.166667h; Stage #2: propanoic acid,1-chloro-2-methylpropyl ester With sodium iodide In ethyl acetate Reflux;

propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) → 2-(2-methyl-1-(propionyloxy)propoxy)-2-oxoethanaminium trifluoroacetate salt (1616274-56-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / ethyl acetate / 0.17 h / 20 °C 1.2: Reflux 2.1: dichloromethane / 2 h / 0 - 20 °C View Scheme

propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) → 1-(2-((1-ethylcarbonyloxyisobutoxycarbonyl)methylcarbamoyl)-3-phenylpropyldisulfanylmethyl)-3-methylsulfanylpropyl ammonium trifluoroacetate (1098011-64-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine / ethyl acetate / 0.17 h / 20 °C 1.2: Reflux 2.1: dichloromethane / 2 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.33 h / 20 °C 4.1: formic acid / 1 h / 20 °C View Scheme

propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) → C29H46N2O7S3 (1616274-74-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / ethyl acetate / 0.17 h / 20 °C 1.2: Reflux 2.1: dichloromethane / 2 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.33 h / 20 °C View Scheme

propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) → (S)-3-aminomethyl-5-methylhexanoic acid 2-methyl-1-propionyloxypropyl ester trifluoroacetate (1026789-31-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: caesium carbonate / methanol / 4 h / 20 °C 1.2: 5 h / 50 °C 2.1: dichloromethane / 20 °C / Cooling with ice View Scheme

propanoic acid,1-chloro-2-methylpropyl ester (58304-65-7) + 3-((4-carbamoyl-2,6-difluorophenoxy)methyl)-4-chlorobenzo[b]thiophene-2-carboxylic acid → 2-methyl-1-(propionyloxy)propyl 3-((4-carbamoyl-2,6-difluorophenoxy)methyl)-4-chlorobenzo[b]thiophene-2-carboxylate

Conditions	Yield
With caesium carbonate; sodium iodide In N,N-dimethyl-formamide at 60℃;

Upstream product

• 79-03-8 propionyl chloride 
• 78-84-2 isobutyraldehyde 

Downstream Products

• 1616274-74-8 C₂₉H₄₆N₂O₇S₃ 
• 1098011-64-3 1-(2-((1-ethylcarbonyloxyisobutoxycarbonyl)methylcarbamoyl)-3-phenylpropyldisulfanylmethyl)-3-methylsulfanylpropyl ammonium trifluoroacetate 
• 1567346-91-1 1-(5-(4-chlorophenyl)-3-(2,6-difluoro-3-(propylsulfonamido)benzoyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)-2-methylpropyl propionate 
• 123599-78-0 [[2-Methyl-1-(1-oxopropoxy)propoxy](4-phenylbutyl)phosphinyl]acetic acid 
• 581106-36-7 [3-[acetyl(phenylmethoxy)amino]propyl]-phosphonic acid bis[2-methyl-1-(1-oxopropoxy)propyl] ester 
• 150368-49-3 2-methyl-1-(1-oxopropoxy)propyl-2-butyl-6-ethoxy-3-<<2'-1H-tetrazol-5-yl<1,1'-biphenyl>-4-yl>oxy>-5-quinoxalinecarboxylate 

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