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

Description

Valeryl chloride, also known as pentanoyl chloride, is an organic compound with the chemical formula C5H9ClO. It is a colorless liquid with a pungent odor and is used as an intermediate in the synthesis of various chemicals.

Uses

Valeryl chloride is used as an intermediate in the production of pharmaceuticals, agrochemicals, surfactants, fragrances, and electronic chemicals. It is particularly useful in the synthesis of various organic compounds due to its reactive nature and ability to form esters, amides, and other functional groups.
Used in Pharmaceutical Industry:
Valeryl chloride is used as a key intermediate in the synthesis of various pharmaceutical compounds, including antibiotics, anti-inflammatory drugs, and analgesics. Its reactivity allows for the formation of esters and amides, which are essential building blocks in the development of these medications.
Used in Agrochemical Industry:
In the agrochemical industry, valeryl chloride is used as an intermediate in the production of pesticides, herbicides, and insecticides. Its ability to form esters and amides makes it a valuable component in the synthesis of these compounds, which are used to protect crops and control pests.
Used in Surfactant Industry:
Valeryl chloride is used as a raw material in the production of surfactants, which are compounds that reduce the surface tension of liquids. These surfactants are used in a variety of applications, including detergents, soaps, and personal care products, due to their ability to create foam and emulsify oils.
Used in Fragrance Industry:
In the fragrance industry, valeryl chloride is used as a building block for the synthesis of various scent compounds. Its reactivity allows for the formation of esters, which are often used to create complex and unique fragrances.
Used in Electronic Chemical Industry:
Valeryl chloride is also used in the electronic chemical industry, where it serves as an intermediate in the production of various electronic materials, such as semiconductors and electronic displays. Its ability to form esters and amides makes it a valuable component in the synthesis of these materials, which are essential for the functioning of electronic devices.

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

• 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 
• 107-27-7 ethylmercury(II) chloride 
• 814-68-6 acryloyl chloride 
• 109-52-4 valeric acid 
• 75-44-5 phosgene 
• 98-88-4 benzoyl chloride 

Downstream Products

• 20261-68-1 1-chlorohexan-2-one 
• 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 
• 5873-43-8 vinyl valerate 
• 20031-96-3 4-hydroxy-3-valeryl-benzoic acid 
• 2963-75-9 pentanoylcholine iodide 
• 7295-44-5 4'-bromovalerophenone 
• 1956-07-6 p-nitrophenyl valerate 

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