141-75-3

Basic information

• Product Name: Butyryl chloride
• Synonyms: AKOS BBS-00003913;BUTYRIC ACID CHLORIDE;BUTYROYL CHLORIDE;BUTYRYL CHLORIDE;BUTANOYL CHLORIDE;N-BUTYRIC ACID CHLORIDE;N-BUTYROYL CHLORIDE;N-BUTYRYL CHLORIDE
• CAS NO: 141-75-3
• Molecular Formula: C₄H₇ClO
• Molecular Weight: 106.55
• EINECS: 205-498-5
• Product Categories: Pharmaceutical Intermediates;Organics;Acid Halides;Carbonyl Compounds;Organic Building Blocks;pharmaceutical, pesticide intermediate
• Mol File: 141-75-3.mol
• Article Data: 125

Chemical Properties

• Melting Point: −89 °C(lit.)
• Boiling Point: 102 °C(lit.)
• Flash Point: 71 °F
• Appearance: Clear slightly yellow/Liquid
• Density: 1.026 g/mL at 25 °C(lit.)
• Vapor Density: 3.7 (vs air)
• Vapor Pressure: 32.9mmHg at 25°C
• Refractive Index: n20/D 1.412(lit.)
• Storage Temp.: Flammables area
• Solubility: Miscible with ether.
• Explosive Limit: 2.5-7.3%(V)
• Water Solubility: decomposes
• Sensitive: Moisture Sensitive
• Merck: 14,1598
• BRN: 605395
• CAS DataBase Reference: Butyryl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Butyryl chloride(141-75-3)
• EPA Substance Registry System: Butyryl chloride(141-75-3)

Safety Data

• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 16-23-26-36-45
• RIDADR: UN 2353 3/PG 2
• WGK Germany: 1
• RTECS: EM0595000
• F: 13
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 141-75-3(Hazardous Substances Data)

Usage

Chemical Properties

Butyryl chloride is a colorless to light yellow liquid with a strong pungent odor. It undergoes vigorous hydrolysis with water; decomposes in water; soluble in almost aprotic organic solvents. It is used as an intermediate for organic synthesis for the preparation of pharmaceuticals, agrochemicals, dyes, cellulose esters, and peroxide compounds.

Uses

Different sources of media describe the Uses of 141-75-3 differently. You can refer to the following data:
1. Butyryl chloride is used as an intermediate for the synthesis of active pharmaceutical ingredients benzoyl peroxide, t-butyl perbenzoate, and benzophenone. It is also used as an acylation reagent. Further, it is used in the preparation of peroxides such as benzoyl peroxide, benzophenone and t-butyl perbenzoate. In addition to this, it is involved in the preparation of chromones and antiproliferative agents. Butyryl chloride has been used to esterify wood meal dissolved in the ionic liquid, 1-butyl-3-methylimidazolium chloride.
2. Butyryl chloride has been used to esterify wood meal dissolved in the ionic liquid, 1-butyl-3-methylimidazolium chloride.

General Description

A clear colorless liquid with a sharp odor. Slightly denser than water. Flash point near 20°F. Severely irritates skin, eyes, and mucous membranes. Used to make other chemicals.

Air & Water Reactions

Highly flammable. Fumes in air. Decomposes exothermically in water to give corrosive hydrochloric acid.

Reactivity Profile

Butyryl chloride slowly dissolves in water with decomposition and formation of a weakly acidic solution. 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

Extremely destructive to the mucous membranes, upper respiratory tract, eyes, and skin. Inhalation may cause death as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting.

Fire Hazard

Special Hazards of Combustion Products: Emits toxic fumes of chlorine gas

Flammability and Explosibility

Flammable

Purification Methods

Check IR to see if there is a significant peak at 3000-3500 cm-1 (br) for OH. If OH is present then reflux with less than one mole equivalent of SOCl2 for 1hour and distil directly. The fraction boiling between 85-100o is then refractionated at atmospheric pressure. Keep all apparatus free from moisture and store the product in sealed glass ampoules under N2. LACHRYMATORY; handle in a good fume hood. [Hefferich & Schaeffer Org Synth Coll Vol I 147 1941, Beilstein 2 IV 803.]

InChI:InChI=1/C4H7ClO/c1-2-3-4(5)6/h2-3H2,1H3

Synthetic route

butyric acid (107-92-6) → butyryl chloride (141-75-3)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In toluene at 100 - 102℃; for 9h;	92%
With thionyl chloride In N,N-dimethyl-formamide Reflux;	90.9%
With thionyl chloride for 0.5h; Heating;	86%

butyric acid (107-92-6) → butanoic acid anhydride (106-31-0) + butyryl chloride (141-75-3)

Conditions	Yield
With phosphorus trichloride at 40 - 50℃; 4-5h;	A n/a B 67%
With phosphorus trichloride at 40 - 50℃; 4-5h;	A 10.54% B 49.3%

trimethylsilyl butyrate (16844-99-8) + chlorosulfonate de trimethylsilyle (4353-77-9) → 2-(Trimethylsiloxysulfonyl)-butansaeure-trimethylsilylester (89056-03-1) + butyryl chloride (141-75-3)

Conditions	Yield
In 1,2-dichloro-ethane for 12h; Heating;	A 62% B n/a

acryloyl chloride (814-68-6) + methylhydridomercury(II) (51176-12-6) → butyryl chloride (141-75-3)

Conditions	Yield
	56%

benzoyl chloride (98-88-4) + butyric acid (107-92-6) → butyryl chloride (141-75-3)

Conditions	Yield
durch Destillation;

tetrachloromethane (56-23-5) + butyraldehyde (123-72-8) → hexachloroethane (67-72-1) + 2-ethylhexenal (645-62-5) + butyryl chloride (141-75-3)

Conditions	Yield
bei der Einwirkung von γ-Strahlen;

Benzotrichlorid (98-07-7) + butyric acid (107-92-6) → butyryl chloride (141-75-3)

Conditions	Yield
With zinc(II) chloride at 70 - 80℃;

Phthaloyl dichloride (88-95-9) + butyric acid (107-92-6) → butyryl chloride (141-75-3)

Conditions	Yield
durch Destillation;

1,1-dichloroethyl ethyl ether (50966-31-9) + butyric acid (107-92-6) → butyryl chloride (141-75-3)

isobutyryl chloride (79-30-1) → butyryl chloride (141-75-3)

Conditions	Yield
aluminium trichloride; Pd(Ph3)3(Cl)(COCH3)+AlCl3 In chloroform-d1 at 50℃; for 168h; Product distribution; variation of calyst;

benzoyl chloride (98-88-4) + butyric acid (107-92-6) → benzoic acid anhydride (93-97-0) + butyryl chloride (141-75-3)

Conditions	Yield
With pyridine N-oxide In dichloromethane; water Mechanism; var. pH, temp., var. concentration PNO;

butyric acid (2 mol ) → butyryl chloride (141-75-3)

Conditions	Yield
With phosphorus trichloride Erhitzen im kochenden Wasserbade und Abdestillieren des gebildeten Butyrylchlorids aus dem Oelbade;
With phosphorus trichloride Erhitzen im kochenden Wasserbade und Abdestillieren des gebildeten Butyrylchlorids im Vakuum;

butyric acid (96 parts ) → butyryl chloride (141-75-3)

Conditions	Yield
With phosphorus trichloride destillieren;

<1-chloro-ethyl>-butyrate → acetaldehyde (75-07-0) + butyryl chloride (141-75-3)

Conditions	Yield
With zinc(II) chloride

butyric acid 1-chloroethyl ester (80195-91-1) + ZnCl2 → acetaldehyde (75-07-0) + butyryl chloride (141-75-3) + paracetaldehyde (123-63-7)

butyraldehyde (123-72-8) → butyryl chloride (141-75-3)

Conditions	Yield
With trichloroisocyanuric acid In dichloromethane at 20℃; for 120h; Inert atmosphere;

oxalyl dichloride (79-37-8) + butyric acid (107-92-6) → butyryl chloride (141-75-3)

Conditions	Yield
In dichloromethane at 20℃; for 3h; Inert atmosphere;

phenethylamine (64-04-0) + butyryl chloride (141-75-3) → N-(2-phenylethyl)butanamide (6283-13-2)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 30℃; for 12h;	100%
In dichloromethane at 20℃; for 1h; Inert atmosphere;	100%
With pyridine
In benzene for 1h; Heating;
With triethylamine In dichloromethane at 0 - 20℃;

4-nitro-aniline (100-01-6) + butyryl chloride (141-75-3) → N-(4'-nitrophenyl)butyramide (54191-12-7)

Conditions	Yield
With NMM In dichloromethane	100%
With triethylamine In dichloromethane at 20℃;	71%
With sodium hydroxide; acetone

diethylamine (109-89-7) + butyryl chloride (141-75-3) → N,N-diethyl-butyramide (1114-76-7)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%
With benzene
With diethyl ether
In benzene
With sodium carbonate In benzene at 0 - 5℃;

butyryl chloride (141-75-3) + 4-bromo-aniline (106-40-1) → N-(4-bromophenyl)butanamide (119199-11-0)

Conditions	Yield
With triethylamine In dichloromethane at 5 - 20℃;	100%
With triethylamine In chloroform at 20℃; for 0.0222222h; Flow reactor;	82%

butyryl chloride (141-75-3) + β-naphthol (135-19-3) → β-naphthyl butyrate (5856-33-7)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%

CYANAMID (420-04-2) + butyryl chloride (141-75-3) → n-butyrylcyanamide (5634-65-1)

Conditions	Yield
With sodium hydroxide In acetone	100%
With triethylamine In benzene

butyryl chloride (141-75-3) + Propargylamine (2450-71-7) → N-(prop-2-yn-1-yl)butyramide (2978-28-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;	100%
With pyridine In diethyl ether	97%
With triethylamine In dichloromethane at 0 - 20℃; for 3h; Huisgen Cycloaddition;	82%

1,8-dihydroxy-9,10-anthracenedione (117-10-2) + butyryl chloride (141-75-3) → Butyric acid 8-butyryloxy-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester

Conditions	Yield
In pyridine for 3h; Ambient temperature;	100%

butyryl chloride (141-75-3) + (R)-N-(1S,2R)-<3-<2-<<(1,1-dimethylethyl)amino>carbonyl>phenyl>-2-hydroxy-1-(phenylmethyl)propyl>-2-amino-4-oxo-4-(benzyloxy)butanamide (159142-00-4) → (R)-N-(1S,2R)-<3-<2-<<(1,1-dimethylethyl)amino>carbonyl>phenyl>-2-hydroxy-1-(phenylmethyl)propyl>-2-<(n-propylcarbonyl)amino>-4-oxo-4-(benzyloxy)butanamide

Conditions	Yield
With triethylamine In dichloromethane for 0.25h; Ambient temperature;	100%

1,2,3,4-tetrahydroisoquinoline (91-21-4) + butyryl chloride (141-75-3) → N-butyryl-1,2,3,4-tetrahydroisoquinoline

Conditions	Yield
With triethylamine In dichloromethane	100%

(R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2, 90719-32-7, 120574-96-1, 102029-44-7) + butyryl chloride (141-75-3) → (R)-3-(1-butyryl)-4-benzyloxazolidine-2-one (111292-87-6, 112459-79-7, 143097-11-4)

Conditions	Yield
Stage #1: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: butyryl chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere;	100%
Stage #1: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: butyryl chloride In tetrahydrofuran at -78 - 20℃; for 0.5h; Inert atmosphere;	100%
Stage #1: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: butyryl chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	99%

2-Phenoxyethanol (122-99-6) + butyryl chloride (141-75-3) → 2-phenoxyethyl butyrate (23511-70-8)

Conditions	Yield
With pyridine	100%

2-mercaptothiazoline (96-53-7) + butyryl chloride (141-75-3) → 1-(2-thioxothiazolidin-3-yl)butan-1-one (75594-82-0)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	100%

butyryl chloride (141-75-3) + 4-hydroxy-2H-1,4-benzoxazin-3-one (771-26-6) → 4-butanoyloxy-(2H)-1,4-benzoxazin-3(4H)-one

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

butyryl chloride (141-75-3) + 4-hydroxy-6-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (69884-06-6) → 4-butanoyloxy-6-methoxy-(2H)-1,4-benzoxazin-3(4H)-one

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

butyryl chloride (141-75-3) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl hexa-2,3-dienoate (131431-64-6, 113644-17-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	100%
Stage #1: ethyl (triphenylphosphoranylidene)acetate With triethylamine In dichloromethane for 0.166667h; Stage #2: butyryl chloride In dichloromethane at -20 - 0℃; for 0.166667h;	97%

tert-butyl 2-[1-(3-aminophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]hydrazinecarboxylate (650628-27-6) + butyryl chloride (141-75-3) → N-[3-(4-tert-butylhydrazino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl]butanamide

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 1h;	100%

Ro 0329774 (663198-02-5) + butyryl chloride (141-75-3) → N-[3-(4-methoxyphenyl)-2-oxo-1-phenyl(1,3,4-trihydropyrimidino[4,5-d]pyrimidin-7-yl)]-N-phenylbutanamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h;	100%

3-bromo-5-methoxyaminobenzene (16618-68-1) + butyryl chloride (141-75-3) → C11H14BrNO2 (1056894-18-8)

Conditions	Yield
With triethylamine In dichloromethane at 5 - 20℃; for 1h;	100%

4-((1R,2R)-1-(5-(4-aminophenyl)-1,3,4-oxadiazol-2-yl)-2-(tert-butyldimethylsilyloxy)propylamino)-2-chloro-3-methylbenzonitrile (1182369-02-3) + butyryl chloride (141-75-3) → N-(4-(5-((1R,2R)-2-(tert-butyldimethylsilyloxy)-1-(3-chloro-4-cyano-2-methylphenylamino)propyl)-1,3,4-oxadiazol-2-yl)phenyl)butyramide (1182369-07-8)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 90h;	100%

4-[(tert-butyldimethylsilyl)oxy]aniline (111359-74-1) + butyryl chloride (141-75-3) → 4'-tert-butyldimethylsilyloxybutyrylanilide (1318981-71-3)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 15h;	100%
With triethylamine In dichloromethane

4-hydroxy-benzaldehyde (123-08-0) + butyryl chloride (141-75-3) → 4-ethylacetoxy benzaldehyde (50262-49-2)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	100%

2-nitro-6-(pyrrolidin-3-ylmethoxy)benzonitrile hydrochloride (1093205-46-9) + butyryl chloride (141-75-3) → 2-nitro-6-((1-butyrylpyrrolidin-3-yl)methoxy)benzonitrile (1093205-49-2)

Conditions	Yield
	100%

m-Anisidine (536-90-3) + butyryl chloride (141-75-3) → N-(3-methoxyphenyl)butanamide (132118-40-2)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 18h; Inert atmosphere;	100%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;	82%
In dichloromethane
Stage #1: m-Anisidine With triethylamine In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: butyryl chloride In tetrahydrofuran at 20℃; for 13h;
Stage #1: m-Anisidine With triethylamine In tetrahydrofuran at 25℃; for 0.166667h; Stage #2: butyryl chloride In tetrahydrofuran at 25℃; for 3h; Sealed tube;

butyryl chloride (141-75-3) + 3-Iodoaniline (626-01-7) → N-(3-iodophenyl)butyramide (1011615-39-6)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 18h; Inert atmosphere;	100%

ethyl benzimidate hydrochloride (5333-86-8) + butyryl chloride (141-75-3) → N-butyryl-benzimidic acid ethyl ester (33243-87-7)

Conditions	Yield
Stage #1: ethyl benzimidate hydrochloride With triethylamine In toluene at 20℃; for 0.166667h; Stage #2: butyryl chloride In toluene at 20℃; for 24h;	100%

ethyl naphthalene-2-carboximidate hydrochloride (4278-14-2) + butyryl chloride (141-75-3) → C17H19NO2 (1415127-32-0)

Conditions	Yield
Stage #1: ethyl naphthalene-2-carboximidate hydrochloride With triethylamine In toluene at 20℃; for 0.166667h; Stage #2: butyryl chloride In toluene at 20℃; for 41.5h;	100%
Stage #1: ethyl naphthalene-2-carboximidate hydrochloride With triethylamine In toluene at 20℃; for 0.166667h; Stage #2: butyryl chloride In toluene at 20℃; for 41.5h;	100%

butyryl chloride (141-75-3) + 3-benzyl-4-ethyl-7-hydroxy-2H-chromen-2-one → 3-benzyl-4-ethyl-2-oxo-2H-chromen-7-yl butyrate (1428238-84-9)

Conditions	Yield
Stage #1: 3-benzyl-4-ethyl-7-hydroxy-2H-chromen-2-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: butyryl chloride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	100%

C23H23N7O4S (1429324-16-2) + butyryl chloride (141-75-3) → C27H29N7O5S (1429324-21-9)

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

piperidine (110-89-4) + butyryl chloride (141-75-3) → 1-(piperidin-1-yl)butan-1-one (4637-70-1)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%
With triethylamine In chloroform at 20℃; for 0.0222222h; Reagent/catalyst; Flow reactor;	99.9%
With triethylamine In dichloromethane at 0 - 20℃; for 14h; Inert atmosphere;	99%

Upstream product

• 7719-12-2 Phosphorus trichloride 
• 7719-09-7 Thionyl chloride 

Downstream Products

• 119313-12-1 2-Benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone 
• 60456-26-0 (R)-Glycidyl butyrate 
• 66230-04-4 Esfenvalerate 
• 495-40-9 Butyrophenone 
• 31904-29-7 Butylferrocene 
• 106-31-0 Butanoic acid,1,1'-anhydride 
• 152628-00-7 7-METHYL-2-PROPYL-1H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID METHYL ESTER 
• 6640-25-1 4-Chlorophenyl cyclopropyl ketone 
• 1866-16-6 S-BUTYRYLTHIOCHOLINE IODIDE 
• 51630-58-1 Fenvalerate 
• 10004-44-1 Hymexazol 
• 152628-03-0 4-Methyl-2-n-propyl-1H-benzimidazole-6-carboxylic acid 
• 58-54-8 Ethacrynic acid 
• 94050-52-9 FLUCYCLOXURON 
• 106-29-6 Butanoic acid,(2E)-3,7-dimethyl-2,6-octadien-1-yl ester 
• 1274-08-4 1,1'-DI-N-BUTYLFERROCENE 
• 529-34-0 1-Tetralone 
• 78-36-4 LINALYL BUTYRATE 
• 76694-37-6 2-chloro-2-trichloroethyl-3，3-dimethyl cyclobutenone 
• 99434-58-9 cycloxydim 
• 2350-46-1 1-(2,3-DICHLORO-4-HYDROXYPHENYL)BUTAN-1-ONE 
• 2777-51-7 Ethyl(4-butyry-2,3-dichloro)phenoxyacetate 
• 52918-63-5 Deltamethrin 
• 52712-76-2 Bunazosin hydrochloride 
• 74051-80-2 Sethoxydim 
• 63765-76-4 ETHYL 2-ACETYL-3-OXO-HEXANOATE 
• 3378-01-6 Diethyl butyrylmalonate 

Recommend Products

• 99176-14-4  1-methyl-3-piperidinyl butyrate 
• 3554-74-3  3-Hydroxy-1-methylpiperidine 
• 4208-57-5  1-(furan-2-yl)butan-1-one 
• 110-00-9  furan 
• 5333-83-5  2-butyrylthiophene 
• 188290-36-0  thiophene 
• 32972-39-7  retinyl butyrate 
• 110-86-1  pyridine 
• 68-26-8  RETINOL 
• 876472-49-0  1-ethynyl-5-isopropyl-2-methyl-cyclohexanol 
• 723755-49-5  butyric acid-(2,4-dimethyl-phenyl ester) 
• 105-67-9  2,4-Xylenol 
• 79852-26-9  1-(5-methylthiophen-2-yl)butan-1-one 
• 554-14-3  2-Methylthiophene 

Related news

A conformational study of Butyryl chloride (cas 141-75-3) using chirped pulse Fourier transform microwave spectroscopy and quantum chemical calculations09/29/2019

The pure rotational spectrum of butyryl chloride has been recorded between 8 and 16GHz using a chirped pulse, Fourier transform microwave spectrometer. The transitions recorded were assigned to two different conformers which have previously been designated syn-gauche and syn-anti. Quantum chemic...detailed