638-29-9

Basic information

• Product Name: Valeryl chloride
• Synonyms: N-butanecarbonylchloride;valeryl;N-VALERYL CHLORIDE;N-VALEROYL CHLORIDE;N-PENTANOYL CHLORIDE;PENTANOYL CHLORIDE;VACL;VALERYL CHLORIDE
• CAS NO: 638-29-9
• Molecular Formula: C₅H₉ClO
• Molecular Weight: 120.58
• EINECS: 211-330-1
• Product Categories: ACID CHLORIDES;Acid Halides;Carbonyl Compounds;Organic Building Blocks;Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 638-29-9.mol
• Article Data: 67

Chemical Properties

• Melting Point: -110 °C
• Boiling Point: 125-127 °C(lit.)
• Flash Point: 91 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.016 g/mL at 25 °C(lit.)
• Vapor Pressure: 10.6mmHg at 25°C
• Refractive Index: n20/D 1.42(lit.)
• Storage Temp.: Flammables area
• Water Solubility: decomposes
• Sensitive: Moisture Sensitive
• BRN: 506293
• CAS DataBase Reference: Valeryl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Valeryl chloride(638-29-9)
• EPA Substance Registry System: Valeryl chloride(638-29-9)

Safety Data

• Hazard Codes: C
• Statements: 10-20-35-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2502 8/PG 2
• WGK Germany: 3
• RTECS: YV9107500
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 638-29-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

Valeryl chloride is an intermediate for pharmaceuticals, agrochemicals, surfactants, fragrances, electronic chemicals.

General Description

A colorless fuming liquid with a pungent odor. Flash point 74°F. Fumes irritate the eyes and mucous membranes. Corrosive.

Air & Water Reactions

Highly flammable. Fumes in air. Reacts exothermically with water to generate hydrochloric and valeric acids, which are corrosive.

Reactivity Profile

Valeryl chloride is acidic. Incompatible with water, with bases, including amines, and with strong oxidizing agents and alcohols. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Health Hazard

May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Flammable

Safety Profile

A corrosive irritant to skin, eyes, and mucous membranes. When heated to decomposition it emits toxic fumes of Cl-.

InChI:InChI=1/C5H9ClO/c1-2-3-4-5(6)7/h2-4H2,1H3

Synthetic route

Hexane-1,2-diol (6920-22-5) → n-valeryl chloride (638-29-9)

Conditions	Yield
With tert-butylhypochlorite; lead acetate; dibenzoyl peroxide In toluene at 20℃; for 0.666667h;	92%

valeric acid (109-52-4) → n-valeryl chloride (638-29-9)

Conditions	Yield
With thionyl chloride	70%
With tetrachlorosilane at 50 - 55℃; for 7h;	63%
With thionyl chloride zuletzt bei 70-90grad;

valeric acid (109-52-4) → pentanoic anhydride (2082-59-9) + n-valeryl chloride (638-29-9)

Conditions	Yield
With phosphorus trichloride at 40 - 50℃; 4-5h;	A n/a B 67.5%
With phosphorus trichloride at 40 - 50℃; 4-5h;	A 14.2% B 48.7%

4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine (383865-57-4) → pentanoic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide + n-valeryl chloride (638-29-9)

Conditions	Yield
	A 48% B n/a

benzoyl chloride (98-88-4) + valeric acid (109-52-4) → n-valeryl chloride (638-29-9)

phosgene (75-44-5) + valeric acid (109-52-4) → n-valeryl chloride (638-29-9)

ethylmercury(II) chloride (107-27-7) + acryloyl chloride (814-68-6) → n-valeryl chloride (638-29-9)

Conditions	Yield
With lithium aluminium tetrahydride Yield given. Multistep reaction;

pent-2-enoic acid (626-98-2, 13991-37-2, 16666-42-5) → n-valeryl chloride (638-29-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen; palladium on activated charcoal 2: oxalyl dichloride / Inert atmosphere View Scheme

n-valeryl chloride (638-29-9) + methoxybenzene (100-66-3) → p-Methoxyvalerophenon (1671-76-7)

Conditions	Yield
With aluminium trichloride In dichloromethane for 15h; Ambient temperature;	100%
(p-MeOC6H4)2BSbCl6 In dichloromethane for 24h; Ambient temperature;	88%
With aluminium trichloride In tetrachloromethane at 0℃; for 2h;	87%

1,2,3-Benzotriazole (95-14-7) + n-valeryl chloride (638-29-9) → 1H-1,2,3-benzotriazol-1-yl(n-butyl)methanone (84298-28-2)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h; Cooling;	100%
With triethylamine In dichloromethane cooling;	91%
at 80 - 100℃; for 0.25h;	79%

n-valeryl chloride (638-29-9) + 1-(2-benzothiophenyl)cyclohexylamine (143603-26-3) → Pentanoic acid (1-benzo[b]thiophen-2-yl-cyclohexyl)-amide

Conditions	Yield
With triethylamine In tetrahydrofuran for 1h; Ambient temperature;	100%

n-valeryl chloride (638-29-9) + 2-carbomethoxyaniline (134-20-3) → methyl 2-(valerylamino)benzoate (136304-94-4)

Conditions	Yield
With triethylamine In chloroform at 0℃; for 4h;	100%
With potassium carbonate In benzene Heating;	82%

n-valeryl chloride (638-29-9) + 4-hydroxy-2H-1,4-benzoxazin-3-one (771-26-6) → 4-valeroyloxy-(2H)-1,4-benzoxazin-3(4H)-one

Conditions	Yield
With pyridine at 20℃; for 12h;	100%
With pyridine for 12h;	99%

n-valeryl chloride (638-29-9) + 4-hydroxy-6-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (69884-06-6) → 4-valeroyloxy-6-methoxy-(2H)-1,4-benzoxazin-3(4H)-one

Conditions	Yield
With pyridine at 20℃; for 12h;	100%

1-amino-1-cyanocyclopentane (49830-37-7) + n-valeryl chloride (638-29-9) → 1-cyano-1-n-pentanoylaminocyclopentane (194984-24-2)

Conditions	Yield
With triethylamine In toluene at 20 - 80℃;	100%
With triethylamine In dichloromethane
With triethylamine In dichloromethane
Stage #1: 1-amino-1-cyanocyclopentane; n-valeryl chloride With triethylamine In dichloromethane at 5 - 20℃; for 3h; Stage #2: In water

n-valeryl chloride (638-29-9) + dibenzylamine (103-49-1) → N,N-dibenzylpentanamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;	100%
With triethylamine In dichloromethane at 0 - 20℃; for 14h; Inert atmosphere;	100%

methyl 4-(4-(2-(3-(((1R,5S)-3,8-diazabicyclo[3.2.1]octan-3-yl)methyl)benzamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamido)-2,6-difluorophenethyl)benzoate + n-valeryl chloride (638-29-9) → methyl 4-(2,6-difluoro-4-(2-(3-(((1R,5S)-8-pentanoyl-3,8-diazabicyclo[3.2.1]octan-3-yl)methyl)benzamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamido)phenethyl)benzoate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 6h;	100%

methyl piperidine-2-carboxylate hydrochloride (32559-18-5) + n-valeryl chloride (638-29-9) → methyl 1-pentanoylpiperidine-2-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;	100%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + n-valeryl chloride (638-29-9) → 3-(1-oxopentyl)-4(S)-(phenylmethyl)-2-oxazolidinone (143868-89-7)

Conditions	Yield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -70 - -65℃; for 0.5h; Inert atmosphere; Stage #2: n-valeryl chloride In tetrahydrofuran at -75 - -65℃; for 1h;	99.9%
With dmap; triethylamine In dichloromethane at 0 - 10℃; for 3h; Large scale;	98%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: n-valeryl chloride In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;	95%

N-((2'-cyano[1,1'-biphenyl]-4-yl)methyl)-L-valine methyl ester hydrochloride (482577-59-3) + n-valeryl chloride (638-29-9) → methyl 2-(N-((2'-cyanobiphenyl-4-yl)methyl)pentanamido)-3-methylbutanoate (137863-90-2)

Conditions	Yield
With potassium carbonate; sodium chloride In 5,5-dimethyl-1,3-cyclohexadiene; water at 20 - 28℃; Solvent; Reagent/catalyst;	99.2%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 5℃; for 1h;
Stage #1: N-((2'-cyano[1,1'-biphenyl]-4-yl)methyl)-L-valine methyl ester hydrochloride With potassium carbonate In o-xylene; water at 25 - 35℃; for 1.33333h; Industry scale; Stage #2: n-valeryl chloride In o-xylene at 25 - 35℃; Industry scale;

1-phenyl-2-methylpropane (538-93-2) + n-valeryl chloride (638-29-9) → 1-(4-isobutylphenyl)pentan-1-one (148367-01-5)

Conditions	Yield
Stage #1: n-valeryl chloride With aluminium trichloride In dichloromethane at 0℃; for 0.5h; Stage #2: 1-phenyl-2-methylpropane In dichloromethane at 0℃; for 1h; Friedel-Crafts acylation;	99.1%
Stage #1: 1-phenyl-2-methylpropane; n-valeryl chloride In Petroleum ether at 20℃; for 0.25h; Stage #2: With trifluorormethanesulfonic acid In Petroleum ether for 10h; Reflux;	79.6%
With sodium hydrogencarbonate; aluminium chloride In dichloromethane

n-valeryl chloride (638-29-9) + aniline (62-53-3) → N-phenylpentanamide (10264-18-3)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h; Cooling with ice;	99%
With triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;	99%
With benzene

n-valeryl chloride (638-29-9) + methyl salicylate (119-36-8) → 2-hydroxy-5-valeryl-benzoic acid methyl ester

Conditions	Yield
Stage #1: n-valeryl chloride; methyl salicylate; aluminum (III) chloride In carbon disulfide at 5 - 20℃; for 20h; Stage #2: With hydrogenchloride In water at 0℃;	99%
With aluminium trichloride; nitrobenzene

4-chlorobenzenesulfonyl chloride (5202-89-1) + n-valeryl chloride (638-29-9) → methyl 5-chloro-2-valerylaminobenzoate (136285-60-4)

Conditions	Yield
With triethylamine In chloroform at 0℃; for 4h;	99%
With sodium hydrogencarbonate; triethylamine In dichloromethane; water	61%

2-amino-5-methylbenzoic acid methyl ester (18595-16-9) + n-valeryl chloride (638-29-9) → methyl 5-methyl-2-valerylaminobenzoate (136285-53-5)

Conditions	Yield
With hydrogenchloride; sodium carbonate; triethylamine In dichloromethane; water	99%
With triethylamine In chloroform at 0℃; for 4h;	62%

n-valeryl chloride (638-29-9) → 3-(1-oxopentyl)-4(S)-(phenylmethyl)-2-oxazolidinone (143868-89-7)

Conditions	Yield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: n-valeryl chloride In tetrahydrofuran; hexane at 20℃; for 15h;	99%

1-aminocyclopentane-1-carboxamide (17193-28-1) + n-valeryl chloride (638-29-9) → 1-(pentanoylamino)cyclopentanecarboxamide (177219-40-8)

Conditions	Yield
With potassium carbonate In dichloromethane; water at 0 - 20℃;	99%
With triethylamine In tetrahydrofuran at 10 - 30℃; for 1h;	87.3%
With triethylamine In dichloromethane at 0℃;

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + n-valeryl chloride (638-29-9) → (R)-3-(1-valeroyl)-4-benzyloxazolidine-2-one

Conditions	Yield
With n-butyllithium In tetrahydrofuran; ethyl acetate	99%

Methyl 3-aminothiophene-2-carboxylate (22288-78-4) + n-valeryl chloride (638-29-9) → methyl 3-pentanoylaminothiophene-2-carboxylate (150113-51-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 16h;	99%
With pyridine

6-fluoro-4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one + n-valeryl chloride (638-29-9) → 6-fluoro-4-valeroyloxy-(2H)-1,4-benzoxazin-3(4H)-one (1204325-75-6)

Conditions	Yield
With pyridine at 0 - 20℃; Inert atmosphere;	99%

6-chloro-4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one (13212-63-0) + n-valeryl chloride (638-29-9) → 6-chloro-4-valeroyloxy-(2H)-1,4-benzoxazin-3(4H)-one (1204325-77-8)

Conditions	Yield
With pyridine at 0 - 20℃; Inert atmosphere;	99%

n-valeryl chloride (638-29-9) + 8-chloro-4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one → 8-chloro-4-valeroyloxy-(2H)-1,4-benzoxazin-3(4H)-one (1204325-79-0)

Conditions	Yield
With pyridine at 0 - 20℃; Inert atmosphere;	99%

(4-phenyl-3'-trifluoromethyl-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-2′-yl)hydrazine (1254981-35-5) + n-valeryl chloride (638-29-9) → N'-[4-(4-phenylpiperidin-1-yl)-3-(trifluoromethyl)pyridin-2-yl]pentanehydrazide (1254981-36-6)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.166667h;	99%

2-amino-5-bromo-N-ethylbenzamide (1263377-68-9) + n-valeryl chloride (638-29-9) → 5-bromo-N-ethyl-2-pentanamidobenzamide

Conditions	Yield
Stage #1: 2-amino-5-bromo-N-ethylbenzamide With triethylamine In dichloromethane for 0.166667h; Inert atmosphere; Stage #2: n-valeryl chloride In dichloromethane at 0 - 20℃;	99%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	82%
Stage #1: 2-amino-5-bromo-N-ethylbenzamide With triethylamine In dichloromethane Inert atmosphere; Stage #2: n-valeryl chloride In dichloromethane at 0 - 20℃;	82%

tert-butyl N-[4-[(3-amino-6-bromo-2-chloro-4-quinolyl) amino]butyl]carbamate + n-valeryl chloride (638-29-9) → tert-butyl N-[4-[[6-bromo-2-chloro-3-(pentanoylamino)-4-quinolyl]amino]butyl]carbamate

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 25℃; for 2h;	99%
With triethylamine In tetrahydrofuran at 0 - 25℃; for 2h;	99%
With triethylamine In tetrahydrofuran at 25℃; for 2h;	99%
With triethylamine In tetrahydrofuran at 0 - 25℃; for 2h;	99%

methyl 4′-(((4-chlorophenyl)amino)methyl)[1,1′-biphenyl]-2-carboxylate + n-valeryl chloride (638-29-9) → methyl 4′-((N-(4-chlorophenyl)pentanamido)methyl)[1,1′-biphenyl]-2-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;	99%

methyl 3′-fluoro-4′-((phenylamino)methyl)[1,1′-biphenyl]-2-carboxylate + n-valeryl chloride (638-29-9) → methyl 3′-fluoro-4′-((N-phenylpentanamido)methyl)[1,1′-biphenyl]-2-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;	99%

methyl 4′-(((4-methoxyphenyl)amino)methyl)[1,1′-biphenyl]-2-carboxylate + n-valeryl chloride (638-29-9) → methyl 4′-((N-(4-methoxyphenyl)pentanamido)methyl)[1,1′-biphenyl]-2-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;	99%

Upstream product

• 75-44-5 phosgene 
• 109-52-4 valeric acid 
• 107-27-7 ethylmercury(II) chloride 
• 814-68-6 acryloyl chloride 
• 626-98-2 pent-2-enoic acid 
• 383865-57-4 4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine 
• 6920-22-5 Hexane-1,2-diol 
• 98-88-4 benzoyl chloride 

Downstream Products

• 3194-17-0 1-furan-2-yl-pentan-1-one 
• 13606-96-7 N-(pyridin-2-yl)pentanamide 
• 6335-35-9 4-methyl-7-valeryloxy-coumarin 
• 101586-41-8 1,5-dimethyl-2-phenyl-4-valeryl-1,2-dihydro-pyrazol-3-one 
• 84928-26-7 N-(4-hydroxyphenyl)pentanamide 
• 311790-83-7 valeric acid o-anisidide 
• 2525-01-1 1-(3,4-dihydroxy-phenyl)-pentan-1-one 
• 153195-50-7 1,2-bis-valeryloxy-benzene 
• 95650-75-2 Pentanoic acid (E)-5-chloro-hex-3-enyl ester 
• 63740-98-7 1-(benzo[d]-1,3-dioxol-5-yl)pentan-1-one 
• 79784-59-1 1-(p-Acetylphenyl)-1-pentanone 
• 82020-21-1 4-Methoxy-benzoic acid N'-pentanoyl-hydrazide 
• 22534-73-2 N-Valeryl-benzamid 
• 134031-12-2 Se-Benzyl pentaneselenoate 

Relevant articles and documents

A Novel Baker's Yeast Catalysed Hydride Reduction of an Epoxide Moiety

The preparation of 2--1-(p-nitrophenyl)-1,2-epoxyheptan-3-one and its subsequent reduction by baker's yeast to the 2,3-diol is described.The mechanism of the reduction of the epoxide was determined using the β-(2)H isotope shift in 13C n.m.r. and mass spectroscopy and appears to be due to a novel enzyme catalysed hydride transfer from cofactors such as NADH or NADPH.

Dihydropyrazole MurA enzyme inhibitor molecule as well as preparation method and application thereof

The invention provides a dihydropyrazole MurA enzyme inhibitor molecule as well as a preparation method and application thereof. The structural formula is shown in the specification, R is a direct-connected alkyl group with the chemical formula of CnH2n+1, and n is equal to 1-7. The preparation method comprises the following steps of by taking acetophenone substances with different substituent groups and 4-(4-methyl piperazinyl) benzaldehyde as raw materials, carrying out aldol condensation reaction under an alkaline condition to obtain an intermediate, and synthesizing a target compound with a structural formula by using the intermediate, hydrazine hydrate and an organic acid with an R-COOH structure. The dihydropyrazole MurA enzyme inhibitor molecule provided by the invention has a bacterial inhibition effect, has an MurA enzyme inhibition effect, and also has an effect of interfering synthesis of bacterial cell walls.

Novel N-Acyl-1H-imidazole-1-carbothioamides: Design, Synthesis, Biological and Computational Studies

The present study reports the convenient synthesis, spectroscopic characterization, bio-assays and computational evaluation of a novel series of N-acyl-1H-imidazole-1-carbothioamides. The screened derivatives displayed excellent antioxidant activity, moderate antibacterial and antifungal potential. The screened derivatives were found to be highly biocompatible against hRBCs. Molecular docking ascertained the mechanism and mode of action towards the molecular target delineating that ligands and complexes were stabilized at the active site by electrostatic and hydrophobic forces in accordance to the corresponding experimental results. Docking simulation provided additional information about the possibilities of inhibitory potential of the compounds against RNA. Computational evaluation predicted that N-acyl-1H-imidazole-1-carbothioamides 5c and 5g can serve as potential surrogates for hit to lead generation and design of novel antioxidant and antibacterial agents.