7065-46-5

Basic information

• Product Name: 3,3-Dimethylbutyryl chloride
• Synonyms: 3,3-DIMETHYL-N-BUTYRYL CHLORIDE;TERT-BUTYLACETYL CHLORIDE;T-BUTYLACETYL CHLORIDE;TBAC;Chloroacetoacetamides;tert-Butylacetyl chloride, 98+%;3,3-Dimethylbutyric acid chloride;3,3-Dimethylbutanoic acid chloride
• CAS NO: 7065-46-5
• Molecular Formula: C₆H₁₁ClO
• Molecular Weight: 134.6
• EINECS: 230-356-4
• Mol File: 7065-46-5.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 127-129 °C(lit.)
• Flash Point: 70 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.969 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.41E-15mmHg at 25°C
• Refractive Index: n20/D 1.421(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 1740421
• CAS DataBase Reference: 3,3-Dimethylbutyryl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-Dimethylbutyryl chloride(7065-46-5)
• EPA Substance Registry System: 3,3-Dimethylbutyryl chloride(7065-46-5)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 3
• F: 9-13-21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 7065-46-5(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to slightly yellow liquid

Uses

3,3-Dimethylbutyryl Chloride is a useful compound in organic synthesis.

InChI:InChI=1/C19H20ClN3O3S2/c1-2-22-9-11-23(12-10-22)19-18(21-17(26-19)16-4-3-13-27-16)28(24,25)15-7-5-14(20)6-8-15/h3-8,13H,2,9-12H2,1H3

Synthetic route

tert-Butylacetic acid (1070-83-3) → 3,3-dimethylbutanoic acid chloride (7065-46-5)

Conditions	Yield
With thionyl chloride at 25℃; for 20h;	86%
With thionyl chloride for 2.5h; Heating;	76.2%
With thionyl chloride

2-Hydrazono-3,3-dimethyl-butyric acid (217300-12-4) → 3,3-dimethylbutanoic acid chloride (7065-46-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / Heating 2: SOCl2 View Scheme

trimethylpyruvic acid (815-17-8) → 3,3-dimethylbutanoic acid chloride (7065-46-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: N2H4 / triethylene glycol 2: KOH / Heating 3: SOCl2 View Scheme

2-(tert-butyl)malonic acid (4379-33-3) → 3,3-dimethylbutanoic acid chloride (7065-46-5)

Conditions	Yield
Multi-step reaction with 2 steps 2: SOCl2 View Scheme

2,4,4-trimethyl-1-pentene (107-39-1) → 3,3-dimethylbutanoic acid chloride (7065-46-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: Cr2O3-H2SO4 2: NaOBr 3: SOCl2 View Scheme

4,4-dimethyl-pentan-2-one (590-50-1) → 3,3-dimethylbutanoic acid chloride (7065-46-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOBr 2: SOCl2 View Scheme

thionyl chloride (7719-09-7) + tert-Butylacetic acid (1070-83-3) → 3,3-dimethylbutanoic acid chloride (7065-46-5)

Conditions	Yield
In dichloromethane at 25℃; for 12h;

ethyl 5-amino-1-(2-fluorobenzyl)-1H-indole-2-carboxylate (509150-37-2) + 3,3-dimethylbutanoic acid chloride (7065-46-5) → ethyl 5-[(3,3-dimethylbutanoyl)-amino]-1-(2-fluorobenzyl)-1H-indole-2-carboxylate (509150-38-3)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%
With triethylamine In dichloromethane at 0 - 20℃;	98%

5-(2-benzyloxy-ethylamino)-benzo[b]thiophene-2-carboxylic acid methyl ester + 3,3-dimethylbutanoic acid chloride (7065-46-5) → 5-[(2-benzyloxy-ethyl)-(3,3-dimethylbutyryl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester (910791-71-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;	100%

3,3-dimethylbutanoic acid chloride (7065-46-5) + 2-methyl-4-bromo-6-chloroaniline (30273-42-8) → N-(4-Bromo-2-chloro-6-methylphenyl)-3,3-dimethyl butanamide (1009344-73-3)

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 4h;	100%

3,3-dimethylbutanoic acid chloride (7065-46-5) + 4-bromo-2,6-dimethylphenylamine (24596-19-8) → N-(4-bromo-2,6-dimethylphenyl)-3,3-dimethylbutanamide (1009344-67-5)

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 4h;	100%
With triethylamine In acetonitrile at 20℃; for 4h;	100%
Stage #1: 4-bromo-2,6-dimethylphenylamine With triethylamine In dichloromethane at 0℃; for 0.333333h; Stage #2: 3,3-dimethylbutanoic acid chloride In dichloromethane at 20℃; for 3h;	81%

1,2-dimethoxybenzene (91-16-7) + 3,3-dimethylbutanoic acid chloride (7065-46-5) → 1-(2',3'-dimethoxyphenyl)-3,3-dimethylbutan-1-one

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; Friedel-Crafts Acylation;	100%

3,3-dimethylbutanoic acid chloride (7065-46-5) + 2-amino-3-bromo-N-methylbenzamide (1022960-45-7) → 8-bromo-3-methyl-2-neopentylquinazolin-4(3H)-one

Conditions	Yield
In 1,4-dioxane at 20 - 100℃; Sealed tube;	100%

3,3-dimethylbutanoic acid chloride (7065-46-5) + 2,6-diisopropylbenzenamine (24544-04-5) → C18H29NO

Conditions	Yield
With triethylamine In ethyl acetate at 50℃; for 3h; Schlenk technique; Inert atmosphere;	99.7%

3-[2-(trifluoromethyl)-α-(2,3-dihydrobenzo[1,4]dioxin-6-yl)benzyloxy]azetidine (791118-91-7) + 3,3-dimethylbutanoic acid chloride (7065-46-5) → 1-[2-(tert-butyl)acetyl]-3-[2-(trifluoromethyl)-α-(2,3-dihydrobenzo[1,4]dioxin-6-yl)benzyloxy]azetidine

Conditions	Yield
With MP-carbonate In dichloromethane at 20℃;	99%

3,3-dimethylbutanoic acid chloride (7065-46-5) + Coarannulen (5821-51-2) → (3,3-dimethylbutan-1-on-1-yl)corannulene (1073651-82-7)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at -78 - 0℃; for 1.5h; Friedel Crafts acylation; Inert atmosphere;	99%

3,3-dimethylbutanoic acid chloride (7065-46-5) + 1,3-Dimethoxybenzene (151-10-0) → 1-(2',4'-dimethoxyphenyl)-3,3-dimethylbutan-1-one

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; Friedel-Crafts Acylation;	99%

3,3-dimethylbutanoic acid chloride (7065-46-5) + 4-(6-(3,8-diazabicyclo[3.2.1]octan-3-yl)pyridin-3-yl)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile dihydrochloride → 4-(6-(8-(3,3-dimethylbutanoyl)-3,8-diazabicyclo[3.2.1]octan-3-yl)pyridin-3-yl)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	99%

3,3-dimethylbutanoic acid chloride (7065-46-5) + phenylacetylene (536-74-3) → 5,5-Dimethyl-1-phenyl-hex-1-yn-3-one

Conditions	Yield
With triethylamine In neat (no solvent) at 40℃; for 8h; Sonogashira Cross-Coupling;	99%

3,3-dimethylbutanoic acid chloride (7065-46-5) + 1-(3,5-dimethyl-4-aminophenyl)4-(3-fluorophenyl)piperidine → N-(4-(4-(3-fluorophenyl)piperidin-1-yl)-2,6-dimethylphenyl)-3,3-dimethylbutanamide hydrochloride

Conditions	Yield
Stage #1: 3,3-dimethylbutanoic acid chloride; 1-(3,5-dimethyl-4-aminophenyl)4-(3-fluorophenyl)piperidine With triethylamine In dichloromethane at 0 - 20℃; for 1h; Stage #2: With hydrogenchloride In dichloromethane; water	99%

ethyl 5-amino-1H-indole-2-carboxylate (71086-99-2) + 3,3-dimethylbutanoic acid chloride (7065-46-5) → ethyl 5-[(3,3-dimethylbutanoyl)-amino]-1H-indole-2-carboxylate (509150-62-3)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h;	98%

3,3-dimethylbutanoic acid chloride (7065-46-5) + 1‐(hydroxymethyl)‐2,5‐bis(trimethylsilylethynyl)ferrocene → (2,5‐bis[(trimethylsilyl)ethynyl]ferrocenyl)methyl 3,3‐dimethylbutanoate

Conditions	Yield
With pyridine at 20℃; for 48h; Inert atmosphere;	98%

3,3-dimethylbutanoic acid chloride (7065-46-5) + ethyl 3-(5-(benzyloxy)-1-(4-chlorobenzyl)-1H-indol-2-yl)-2,2-dimethylpropanoate → 1-(4-chlorobenzyl)-3-(3,3-dimethylbutanoyl)-2-(3-ethoxy-2,2-dimethyl-3-oxopropyl)-1H-indol-5-yl 3,3-dimethylbutanoate

Conditions	Yield
With aluminum (III) chloride In 1,2-dichloro-ethane at -70℃; for 0.5h; Inert atmosphere;	98%

1,2,3-Benzotriazole (95-14-7) + 3,3-dimethylbutanoic acid chloride (7065-46-5) → 1-(1H-1,2,3-benzotriazol-1-yl)-3,3-dimethyl-1-butanone (55889-34-4)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h; Acylation;	97%
With triethylamine In dichloromethane for 4h; cooling;	91%
With triethylamine In dichloromethane at 0 - 20℃;

3,3-dimethylbutanoic acid chloride (7065-46-5) + (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2, 90719-32-7, 120574-96-1, 102029-44-7) → (R)-4-benzyl-3-(3,3-dimethylbutanoyl)oxazolidin-2-one

Conditions	Yield
Stage #1: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,3-dimethylbutanoic acid chloride In tetrahydrofuran; hexane at -78℃; for 2h;	97%
With dmap; triethylamine In tetrahydrofuran at 0 - 20℃; for 1h;	89%
Stage #1: (R)-4-(phenylmethyl)-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 3,3-dimethylbutanoic acid chloride In tetrahydrofuran at -78 - 20℃; for 3h; Time;

3,3-dimethylbutanoic acid chloride (7065-46-5) + 4-bromobenzoic acid hydrazide (5933-32-4) → 4-bromo-N'-(3,3-dimethylbutanoyl)benzoic hydrazide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	96.1%

3,3-dimethylbutanoic acid chloride (7065-46-5) + N-methylaniline (100-61-8) → N-methyl-N-phenyl-3,3-dimethylbutanamide (144691-18-9)

Conditions	Yield
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide at 20 - 25℃; for 1.5h; pH=11.5; Schotten-Baumann-type reaction;	96%
With triethylamine In ethyl acetate at 0℃;

3,3-dimethylbutanoic acid chloride (7065-46-5) + (3R,4S)-3-triethylsilyloxy-4-phenylazetidin-2-one (149140-54-5) → (3R,4S)-1-neopentylcarbonyl-4-phenyl-3-triethylsilyloxyazetidin-2-one (355113-95-0)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3h;	96%

diphenylether (101-84-8) + 3,3-dimethylbutanoic acid chloride (7065-46-5) → 4,4'-bis(3,3-dimethylbutanoyl)diphenyl ether (791137-05-8)

Conditions	Yield
With aluminium trichloride In dichloromethane at 0℃; for 5h;	96%

octanol (111-87-5) + 3,3-dimethylbutanoic acid chloride (7065-46-5) → 1-octyl 3,3-dimethylbutanoate

Conditions	Yield
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide at 20 - 25℃; for 1.5h; pH=11.5; Schotten-Baumann-type reaction;	96%

3,3-dimethylbutanoic acid chloride (7065-46-5) + 2-(3,4-dihydroisoquinolin-2(1H)-yl)-4,6-dimethoxypyrimidin-5-amine (1093352-31-8) → N-(2-(3,4-dihydroisoquinolin-2(1H)-yl)-4,6-dimethoxypyrimidin-5-yl)-3,3-dimethylbutanamide (1093352-19-2)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1h;	96%

3,3-dimethylbutanoic acid chloride (7065-46-5) + (1-chloroethyl)benzene (672-65-1) → 5,5-dimethyl-2-phenylhexan-3-one (40560-92-7)

Conditions	Yield
Stage #1: (1-chloroethyl)benzene With chloro-trimethyl-silane; ethylene dibromide; lithium chloride; zinc In tetrahydrofuran at 25℃; for 11h; Inert atmosphere; Stage #2: With copper(I) cyanide di(lithium chloride) In tetrahydrofuran at -25℃; for 0.25h; Stage #3: 3,3-dimethylbutanoic acid chloride In tetrahydrofuran at -60 - 25℃; Inert atmosphere;	96%

3,3-dimethylbutanoic acid chloride (7065-46-5) + diethyl aminopropanedioate hydrochloride (137684-40-3) → diethyl [(3,3-dimethylbutanoyl)amino]propanedioate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 18h;	96%

3,3-dimethylbutanoic acid chloride (7065-46-5) + 3-chloro-aniline (108-42-9) → N-(3-chlorophenyl)-3,3-dimethylbutanamide (132118-44-6)

Conditions	Yield
With triethylamine In diethyl ether at 0 - 20℃; for 2h; Inert atmosphere;	96%

3,3-dimethylbutanoic acid chloride (7065-46-5) + 1-chloro-2-methoxynaphthalene (13101-92-3) → C17H19ClO2 (1441766-88-6)

Conditions	Yield
With cetyltrimethylammonim bromide; cetyltrimethylammonium chloride In 1,2-dichloro-ethane at 70℃; for 0.0833333h; Friedel-Crafts Acylation; Microwave irradiation; Micellar solution;	96%

3,3-dimethylbutanoic acid chloride (7065-46-5) + 1-bromo-2-methoxynaphthalene (3401-47-6) → C17H19BrO2 (1441766-36-4)

Conditions	Yield
With cetyltrimethylammonim bromide; cetyltrimethylammonium chloride In 1,2-dichloro-ethane at 70℃; for 0.0833333h; Friedel-Crafts Acylation; Microwave irradiation; Micellar solution;	96%

diazomethane (186581-53-3, 908094-01-9) + 3,3-dimethylbutanoic acid chloride (7065-46-5) → 1-Diaz-4,4-dimethylpentan-2-one (76828-10-9)

Conditions	Yield
In diethyl ether	95%
In diethyl ether for 2h;
In diethyl ether at 0 - 20℃; for 1h;

Upstream product

• 1070-83-3 tert-Butylacetic acid 
• 217300-12-4 2-Hydrazono-3,3-dimethyl-butyric acid 
• 815-17-8 trimethylpyruvic acid 
• 4379-33-3 2-(tert-butyl)malonic acid 
• 107-39-1 2,4,4-trimethyl-1-pentene 
• 590-50-1 4,4-dimethyl-pentan-2-one 
• 7719-09-7 thionyl chloride 

Downstream Products

• 38965-27-4 17β-(3,3-dimethyl-butyryloxy)-androst-4-en-3-one 
• 595-56-2 21-(3,3-dimethyl-butyryloxy)-9-fluoro-11β,17-dihydroxy-pregn-4-ene-3,20-dione 
• 5340-62-5 3-ethyl-5,5-dimethylhexan-3-ol 
• 5340-30-7 5,5-dimethyl-3-hexanone 
• 82251-67-0 3,3-dimethyl-butyric acid-((1R)-menthyl ester) 
• 5129-40-8 ethyl 2,2-dimethylbutanoate 
• 1762-19-2 2,2-dimethyl-heptan-4-one 
• 40239-19-8 2,2,6-trimethyl-heptan-4-one 
• 29336-30-9 2-bromo-3,3-dimethylbutanoyl chloride 
• 7473-22-5 3,3-dimethyl-butyric acid cyclohexylamide 
• 67630-75-5 3,3-Dimethyl-butyric acid 5-(2-bromo-acetyl)-2-(3,3-dimethyl-butyryloxy)-phenyl ester 
• 67630-59-5 2-bromo-3',5'-bis(3,3-dimethylbutyryloxy)acetophenone 
• 23703-68-6 C₁₄H₁₈Cl₂N₂O₃ 
• 47306-11-6 3,3-Dimethyl-butyric acid 4-(2-tert-butylamino-acetyl)-2-hydroxy-phenyl ester 

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