79-30-1

Basic information

• Product Name: Isobutyryl chloride
• Synonyms: 2-methyl-propanoylchlorid;chloroisopropylketone;dimethylacetylchloride;Isobutyric acid chloride;isobutyricacidchloride;isobutyryl;Propanoyl chloride, 2-methyl-;ISOBUTANOYLCHLORIDE
• CAS NO: 79-30-1
• Molecular Formula: C₄H₇ClO
• Molecular Weight: 106.55
• EINECS: 201-194-1
• Product Categories: Organics;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Protecting Agents for Hydroxyl and Amino Groups;Protecting Agents, Phosphorylating Agents & Condensing Agents;Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 79-30-1.mol
• Article Data: 71

Chemical Properties

• Melting Point: -90 °C
• Boiling Point: 91-93 °C(lit.)
• Flash Point: 34 °F
• Appearance: Clear/Liquid
• Density: 1.017 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.07 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.407(lit.)
• Storage Temp.: Store at RT.
• Solubility: Miscible with chloroform, glacial acetic acid, ether, toluene, m
• Explosive Limit: 2.1-8.2%(V)
• Water Solubility: Reacts
• Sensitive: Moisture Sensitive
• BRN: 605393
• CAS DataBase Reference: Isobutyryl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Isobutyryl chloride(79-30-1)
• EPA Substance Registry System: Isobutyryl chloride(79-30-1)

Safety Data

• Hazard Codes: F,C,T
• Statements: 11-35-23
• Safety Statements: 16-23-26-36-45-36/37/39-28A
• RIDADR: UN 2395 3/PG 2
• WGK Germany: 1
• RTECS: UC3944000
• F: 13
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 79-30-1(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid.Soluble in ether; reacts with water and alcohol.

Uses

Different sources of media describe the Uses of 79-30-1 differently. You can refer to the following data:
1. Usually used in the synthesis of fully isobutyramide terminated hyperbranched polyethylenimines,the separation and identification of shikonin and its ester derivatives in the root epidermis of Echium italicum.
2. Isobutyryl chloride is used in the preparation of fully isobutyramide terminated hyperbranched polyethylenimines. It plays an important role in the separation and identification of shikonin and its ester derivatives in the root epidermis of Echium italicum L. It acts as an acylating agent for the ketimine derivatives of alfa-amino esters, nucleosides and pyrroles. Further, it is used in the preparation of organic peroxides. In addition to this, it is used as an intermediate for dyes, textile auxiliaries and peroxide compounds.

General Description

A colorless liquid. Flash point near 50°F. Irritates skin, eyes and mucous membranes. Toxic by ingestion, inhalation and skin absorption. Used to make other chemicals.

Air & Water Reactions

Highly flammable. Produces corrosive toxic fumes containing HCl on contact with moist air. Decomposes in water.

Reactivity Profile

Isobutyryl chloride is water reactive. Incompatible with strong oxidizing agents, alcohols, bases (including amines). 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].

Hazard

Low toxicity by inhalation. A severe eye irritant.

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

Highlyflammable

InChI:InChI=1/C4H7ClO/c1-3(2)4(5)6/h3H,1-2H3

Synthetic route

isobutyric Acid (79-31-2) → isobutyryl chloride (79-30-1)

Conditions	Yield
With phosphorus trichloride at 45 - 55℃; for 6h;	99.6%
With trichloroacetonitrile; triphenylphosphine In dichloromethane at 30℃; Temperature; Inert atmosphere;	99.76%
Stage #1: isobutyric Acid With phosphorus trichloride at 60℃; for 2h; Stage #2: With hydrogenchloride for 0.3h; Temperature;	97.5%

2-(5-amino-2-ethoxyphenyl)-pyrido[3,2-d]pyrimidin-4(3H)-one (155879-72-4) → 2-(5-Isobutyrylamino-2-ethoxyphenyl)pyrido[3,2-d]pyrimidin-4(3H)-one + isobutyryl chloride (79-30-1)

Conditions	Yield
	A 80% B n/a

trimethylsilyl isobutyrate (16883-61-7) + chlorosulfonate de trimethylsilyle (4353-77-9) → 2-Methyl-2-(trimethylsiloxysulfonyl)-propansaeure-trimethylsilylester (89056-04-2) + isobutyryl chloride (79-30-1)

Conditions	Yield
In 1,2-dichloro-ethane for 12h; Heating;	A 61% B n/a

4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine (383865-57-4) → N-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isobutyramide + isobutyryl chloride (79-30-1)

Conditions	Yield
	A 8% B n/a

benzoyl chloride (98-88-4) + isobutyric Acid (79-31-2) → isobutyryl chloride (79-30-1)

Conditions	Yield
durch Destillation;

isobutyric acid hydrazide (3619-17-8) → isobutyryl chloride (79-30-1)

Conditions	Yield
With hydrogenchloride; dichloromethane; chlorine

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

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

isobutyryl radical (35586-36-8) → isobutyryl chloride (79-30-1)

Conditions	Yield
With tetrachloromethane In hexane at 22.9℃; Rate constant;

dichloromethane (75-09-2) + chlorine (7782-50-5) + isobutyric acid hydrazide (3619-17-8) → isobutyryl chloride (79-30-1)

isobutyrate sodium → isobutyryl chloride (79-30-1)

Conditions	Yield
With trichlorophosphate

2-methyl-4,5-dihydro-1,3-oxazole (1120-64-5) + acetyl chloride (75-36-5) → isobutyryl chloride (79-30-1) + 1-(4,5-dihydrooxazol-2-yl)propan-2-one (13670-39-8)

Conditions	Yield
With n-butyllithium In tetrahydrofuran

C3Cl2(C3H7)2 (69151-13-9) + isobutyric Acid (79-31-2) → 2,3-diisopropylcyclopropenone (877675-72-4) + isobutyryl chloride (79-30-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere;	A 66.9 mg B n/a

isobutyraldehyde (78-84-2) → isobutyryl chloride (79-30-1)

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

(trichloromethyl)mesitylene (707-74-4) + isobutyric Acid (79-31-2) → isobutyryl chloride (79-30-1) + mesitylene-2-carboxylic acid chloride (938-18-1)

Conditions	Yield
With iron(III) chloride at 100℃; for 3h; Inert atmosphere;	A 6.7 kg B 11.5 kg

anthranilic acid (118-92-3) + isobutyryl chloride (79-30-1) → 2-isobutyramidobenzoic acid (17840-96-9)

Conditions	Yield
In N,N-dimethyl acetamide at 0℃; for 4h;	100%
With benzene

Isopropylbenzene (98-82-8) + isobutyryl chloride (79-30-1) → 1-(4-isopropylphenyl)-2-methyl-1-propanone (72846-62-9)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 20℃; for 2.5h; Inert atmosphere;	100%
With aluminium trichloride at 25℃; Product distribution;
With carbon disulfide; aluminium trichloride
Friedel-Crafts Acylation;
With aluminum (III) chloride In dichloromethane at 0℃; for 2h; Friedel-Crafts Acylation; Sealed tube; Inert atmosphere;

biphenyl (92-52-4) + isobutyryl chloride (79-30-1) → 1-([1,1′-biphenyl]-4-yl)-2-methylpropan-1-one (6976-20-1)

Conditions	Yield
With aluminium trichloride In dichloromethane at 0 - 20℃; for 14.5h;	100%
With aluminium trichloride In carbon disulfide Friedel-Crafts acylation; Heating;	54%
With carbon disulfide; aluminium trichloride
With aluminium trichloride In carbon disulfide
With aluminum (III) chloride In 1,2-dichloro-ethane at 5 - 10℃; for 5h; Solvent; Temperature;

isobutyryl chloride (79-30-1) + recorcinol (108-46-3) → 1-(2,4-dihydroxyphenyl)-2-methyl-1-propanone (29048-54-2)

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃;	100%
at 90℃;
With aluminium trichloride; nitrobenzene at 40 - 50℃;

monohydroxymethyl-alpha-terthiophene (13059-93-3) + isobutyryl chloride (79-30-1) → 5-isobutyryloxymethyl-[2,2';5',2'']terthiophene (26905-75-9)

Conditions	Yield
With pyridine In dichloromethane	100%

isobutyryl chloride (79-30-1) + methyl 2,6-anhydro-3-C-methyl-2-thio-β-L-mannopyranoside (151929-68-9) → methyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-2-thio-β-L-mannopyranoside (151929-69-0)

Conditions	Yield
With pyridine; dmap at 25℃; for 1.5h;	100%
With pyridine; dmap at 25℃; for 1.5h;	100%

N-[2-(6-amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide hydrochloride (1000334-09-7) + isobutyryl chloride (79-30-1) → N-(3-(2-(acetylamino)ethyl)-4-hydroxy-2,3-dihydro-1H-inden-5-yl)-2-methylpropanamide (1000334-12-2)

Conditions	Yield
With pyridine at 0℃; for 3h;	100%

6-chloroindole (17422-33-2) + isobutyryl chloride (79-30-1) → 1-(6-chloro-1H-indol-3-yl)-2-methyl-1-propanone (1002095-56-8)

Conditions	Yield
Stage #1: 6-chloroindole With methylmagnesium bromide In diethyl ether for 0.333333h; Stage #2: With zinc(II) chloride In diethyl ether for 0.5h; Stage #3: isobutyryl chloride In diethyl ether Further stages.;	100%
Stage #1: 6-chloroindole; methylmagnesium bromide In diethyl ether for 0.25h; Stage #2: With zinc(II) chloride In diethyl ether for 0.5h; Stage #3: isobutyryl chloride With ammonium chloride more than 3 stages;

3-Hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione (15297-98-0, 41019-52-7, 41135-46-0) + isobutyryl chloride (79-30-1) → C19H20O5

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 18h;	100%

(S)-3-[(biphenyl-2-ylmethyl)-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester (892388-55-5) + isobutyryl chloride (79-30-1) → tert-butyl (3S)-3-[(biphenyl-2-ylmethyl)(isobutyryl)amino]pyrrolidine-1-carboxylate (892388-56-6)

Conditions	Yield
With triethylamine In 1,4-dioxane at 70℃; for 2h;	100%
With triethylamine In 1,4-dioxane at 70℃; for 2h;
With triethylamine In 1,4-dioxane at 20℃;

2-fluorophenol (367-12-4) + isobutyryl chloride (79-30-1) → 2-fluorophenyl 2-methylpropionate (879339-58-9)

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 2h;	100%

4-(N-hydroxycarbamimidoyl)piperidine-1-carboxylic acid tert-butyl ester (280110-63-6, 782493-60-1) + isobutyryl chloride (79-30-1) → C15H27N3O4

Conditions	Yield
With triethylamine; dmap In dichloromethane at 5 - 20℃; for 18.25h;	100%

4-amino-1-benzylpiperidine (50541-93-0) + isobutyryl chloride (79-30-1) → N-(1-benzylpiperidin-4-yl)isobutyramide (312924-69-9)

Conditions	Yield
With sodium carbonate In dichloromethane at 20℃; for 2h;	100%
With sodium hydroxide In diethyl ether at 20℃;	96%
With triethylamine In dichloromethane at 20℃; for 1h;	60%
With triethylamine In dichloromethane at 0℃; Inert atmosphere;
With sodium hydroxide In diethyl ether; water at 0 - 20℃; for 18.25h;

1-(2-chloro-4-nitro-phenyl)piperazine (114878-60-3) + isobutyryl chloride (79-30-1) → 1-(4-(2-chloro-4-nitrophenyl)piperazin-1-yl)-2-methylpropan-1-one (354124-99-5)

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

isobutyryl chloride (79-30-1) + dibenzylamine (103-49-1) → 2-methyl-N,N-bis(phenylmethyl)-propionamide (6284-09-9)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 14h; Inert atmosphere;	100%
With triethylamine In diethyl ether at 0 - 20℃;	92%

(S)-N'-hydroxy-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzamidine (1092113-85-3) + isobutyryl chloride (79-30-1) → (S)-5-[3-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (1092113-86-4)

Conditions	Yield
With pyridine at 90℃;	100%

methyl 2-phenoxyacetate (2065-23-8) + isobutyryl chloride (79-30-1) → methyl 4-(2,2-dimethylacetyl)phenoxyacetate

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0℃; Friedel Crafts Acylation; Inert atmosphere;	100%

(2S,4R)-4-[2-amino-6-(2-nitrophenoxy)-purin-9-yl]-2-(tert-butoxycarbonylmethoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (876954-00-6) + isobutyryl chloride (79-30-1) → (2S,4R)-2-(tert-butoxycarbonylmethoxymethyl)-4-[2-isobutyrylamino-6-(2-nitrophenoxy)-purin-9-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (876954-02-8)

Conditions	Yield
With pyridine at 20℃; Cooling with ice;	100%

racemic 3-(3-N,N'-diisopropylamino-1-phenyl-propyl)-4-hydroxy-benzoic acid (1076199-77-3) + isobutyryl chloride (79-30-1) → 2-(3-N,N-diisopropylamine-1-phenylpropyl)-4-carboxyphenol isobutyrate (1262778-55-1)

Conditions	Yield
With triethylamine In dichloromethane at 25 - 30℃;	100%
With triethylamine In dichloromethane at 25 - 30℃;

(4-(2-chloropyrimidin-4-yl)aniline) (1292318-07-0) + isobutyryl chloride (79-30-1) → N-[4-(2-chloropyrimidin-4-yl)phenyl]-2-methyl-propanamide (1292318-08-1)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	100%
With triethylamine In dichloromethane at 20℃; for 0.5h;	100%

[8-(4-fluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]-[di-(tert-butoxycarbonyl)]-amine (1319068-06-8) + isobutyryl chloride (79-30-1) → [8-(4-fluoro-phenyl)-7-isobutyryl-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]-[di-(tert-butoxycarbonyl)]-amine (1319068-09-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 50℃; for 16h;	100%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 50℃; for 16h;	100%

Upstream product

• 98-88-4 benzoyl chloride 
• 79-31-2 isobutyric Acid 
• 16883-61-7 trimethylsilyl isobutyrate 
• 4353-77-9 chlorosulfonate de trimethylsilyle 
• 75-09-2 dichloromethane 
• 7782-50-5 chlorine 
• 3619-17-8 isobutyric acid hydrazide 
• 1120-64-5 2-methyl-4,5-dihydro-1,3-oxazole 
• 75-36-5 acetyl chloride 
• 69151-13-9 C₃Cl₂(C₃H₇)2 
• 707-74-4 (trichloromethyl)mesitylene 
• 78-84-2 isobutyraldehyde 
• 155879-72-4 2-(5-amino-2-ethoxyphenyl)-pyrido[3,2-d]pyrimidin-4(3H)-one 
• 383865-57-4 4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine 

Downstream Products

• 17687-63-7 1-chloro-3-methylbutan-2-one 
• 4208-53-1 2-methyl-1-(2-furyl)-1-propanone 
• 36448-60-9 2-methyl-1-thiophen-2-yl-propan-1-one 
• 6269-65-4 N-(4-amino-2-methyl-[6]quinolyl)-isobutyramide 
• 5461-08-5 3,4-methylenedioxybenzyl isobutanoate 
• 79322-87-5 ethyl 3-oxo-2-acetyl-4-methylpentanoate 
• 6876-49-9 N-(4-methylphenyl)-2,2-dimethylacetamide 
• 97806-75-2 N-[2-(3,4-dimethoxyphenyl)ethyl]-2-methylpropanamide 
• 2772-54-5 N-Ethyl-isobutyramid 
• 69737-54-8 N,N-diphenyl-2-methylpropanamide 
• 933-52-8 2,2,4,4-tetramethyl-1,3-cyclobutanedione 
• 33931-44-1 N,N-diethylisobutyramide 
• 15727-77-2 Prop-2-enyl 2-methylpropionate 
• 52220-93-6 N-acetyl-2-methylpropanamide 

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