5856-77-9

Basic information

• Product Name: 2,2-Dimethylbutyryl chloride
• Synonyms: 2,2-Dimethylbutyricacidchloride;2,2-dimethylbutanoyl chloride;2,2-DIMETHYLBUTYRYL CHLORIDE;Dimethylbutyrylchloride;2,2-dimethylbutyl chloride;2,2 DiMethylbutiryl chloride;5856-77-9
• CAS NO: 5856-77-9
• Molecular Formula: C₆H₁₁ClO
• Molecular Weight: 134.6
• EINECS: 227-478-5
• Product Categories: intermediate
• Mol File: 5856-77-9.mol
• Article Data: 39

Chemical Properties

• Boiling Point: 133°C
• Flash Point: 29°C
• Appearance: /
• Density: 0,98 g/cm3
• Vapor Pressure: 9.14mmHg at 25°C
• Refractive Index: 1.4240
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Chloroform, Ethyl Acetate
• Water Solubility: Reacts with water. Soluble in chloroform and ethyl acetate.
• Sensitive: Moisture Sensitive
• BRN: 1743935
• CAS DataBase Reference: 2,2-Dimethylbutyryl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethylbutyryl chloride(5856-77-9)
• EPA Substance Registry System: 2,2-Dimethylbutyryl chloride(5856-77-9)

Safety Data

• Hazard Codes: C
• Statements: 10-34-43
• Safety Statements: 26-36/37/39-45-36/37-20
• RIDADR: 2924
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 5856-77-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

,2-Dimethylbutanoyl chloride is a reagent that is used in the synthesis of 4α,5-Dihydro Simvastatin, the drug, is sold under the trade name Zocor. A competitive inhibitor of HMG-CoA reductase. A synthetic analog of Lovastatin. Antilipemic.

InChI:InChI=1/C6H11ClO/c1-4-6(2,3)5(7)8/h4H2,1-3H3

Synthetic route

2,2-dimethylbutyric acid (595-37-9) → 2,2-dimethylbutanoyl chloride (5856-77-9)

Conditions	Yield
With thionyl chloride at 100℃; for 2h;	76%
With oxalyl dichloride In dichloromethane at 20℃; for 1h;	68.3%
With thionyl chloride

tert-Butylacetic acid (1070-83-3) → 2,2-dimethylbutanoyl chloride (5856-77-9)

Conditions	Yield
With thionyl chloride

tert-Butylacetic acid (1070-83-3) + benzoyl chloride (98-88-4) → 2,2-dimethylbutanoyl chloride (5856-77-9)

2,2-dimethyl-butanoic acid methyl ester (813-67-2) → 2,2-dimethylbutanoyl chloride (5856-77-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; water / methanol / 65 °C 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 17 h / 0 - 20 °C View Scheme

3-amino-4-[(cyclohexylmethyl)amino]-benzonitrile (809273-56-1) + 2,2-dimethylbutanoyl chloride (5856-77-9) → 1-(cyclohexylmethyl)-2-(1,1-dimethylpropyl)-1H-benzimidazole-5-carbonitrile (809273-57-2)

Conditions	Yield
Stage #1: 3-amino-4-[(cyclohexylmethyl)amino]-benzonitrile; 2,2-dimethylbutanoyl chloride With dmap In dichloromethane at 0 - 20℃; Stage #2: In dichloromethane at 190℃; for 2h; Microwave irradiation;	100%

6(R)-[2-(8'(S)-hydroxy-2'(S),6'(R)-dimethyl-1',2',6',7',8',8a'(R)-hexahydronaphtyl-1'(S))ethyl]-4(R)-(dimethyltertbutylsilyloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one + 2,2-dimethylbutanoyl chloride (5856-77-9) → 6(R)-[2-(8'(S)-2'',2''-dimethylbutyryloxy-2'(S),6'(R)-dimethyl-1',2',6',7',8',8a'(R)-hexahydronaphthyl-1'(S))ethyl]-4(R)-(dimethyltertbutylsilyloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions	Yield
With 4-methyl-morpholine; potassium iodide for 4 - 5h; Heating / reflux;	100%

2,2-dimethylbutanoyl chloride (5856-77-9) + 5-amino-2,3-dihydrofuro<3,2-b>pyridine (95837-11-9) → N-(2,3-dihydrofuro[3,2-b]pyridin-5-yl)-2,2-dimethylbutyramide (1029128-34-4)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	100%

2,2-dimethylbutanoyl chloride (5856-77-9) + (S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2) → (S)-2-(2,2-dimethylbutyryl)oxy-2'-hydroxy-1,1'-binaphthyl

Conditions	Yield
With triethylamine In dichloromethane at -10 - 20℃;	100%

2,2-dimethylbutanoyl chloride (5856-77-9) + 3,3',4,4'-tetraaminobiphenyl tetrahydrochloride dihydrate → 3,3',4,4'-tetra(2,2-dimethylbutyrylamido)biphenyl (1184267-88-6)

Conditions	Yield
Stage #1: 2,2-dimethylbutanoyl chloride; 3,3',4,4'-tetraaminobiphenyl tetrahydrochloride dihydrate In dichloromethane for 0.0833333h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at 20℃; for 18h; Inert atmosphere;	99%

Methyl 3-mercaptopropionate (2935-90-2) + 2,2-dimethylbutanoyl chloride (5856-77-9) → methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate (938063-63-9)

Conditions	Yield
Stage #1: Methyl 3-mercaptopropionate; 2,2-dimethylbutanoyl chloride In dichloromethane at 10℃; for 0.25h; Stage #2: With ammonia In dichloromethane at 0 - 65℃; for 1.8h; pH=7; Time; Solvent;	98.4%
With N-ethyl-N,N-diisopropylamine In Isopropyl acetate at 2 - 25℃; for 2.16h;	80%
at 50℃; for 18h; Temperature;	79.5 g

2,2-dimethylbutanoyl chloride (5856-77-9) + 2-(2,4-dichlorophenyl)-1-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-3-one (127655-56-5) → 6-(2,4-dichlorophenyl)-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl 2,2-dimethylbutanoate

Conditions	Yield
Stage #1: 2-(2,4-dichlorophenyl)-1-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-3-one With triethylamine In dichloromethane for 0.5h; Stage #2: 2,2-dimethylbutanoyl chloride In dichloromethane at 0 - 20℃; for 12h;	96%

2,2-dimethylbutanoyl chloride (5856-77-9) + 2-Amino-4,6-dimethylpyridine (5407-87-4) → N-(4,6-dimethylpyridin-2-yl)-2,2-dimethylbutanamide (1029127-97-6)

Conditions	Yield
With triethylamine In dichloromethane	95%

2,2-dimethylbutanoyl chloride (5856-77-9) + 2-hydroxyethanethiol (60-24-2) → C8H16O2S

Conditions	Yield
With triethylamine In dichloromethane at 0 - 25℃; for 14h; Reagent/catalyst; Inert atmosphere;	95%

2,2-dimethylbutanoyl chloride (5856-77-9) + 1-hydroxy-2-(4-methoxyphenyl)-5,6,7,7a-tetrahydro-3H-pyrrolizin-3-one → 6-(4-methoxyphenyl)-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl 2,2-dimethylbutanoate

Conditions	Yield
Stage #1: 1-hydroxy-2-(4-methoxyphenyl)-5,6,7,7a-tetrahydro-3H-pyrrolizin-3-one With triethylamine In dichloromethane for 0.5h; Stage #2: 2,2-dimethylbutanoyl chloride In dichloromethane at 0 - 20℃; for 12h;	95%

2,2-dimethylbutanoyl chloride (5856-77-9) + (+)-ethyl (1S,2S,4aR,6S,8S,8aS)-6-(carboxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-8-hydroxy-2-methylnaphthalene-1-carboxylate (102299-03-6) → (+)-ethyl (1S,2S,4aR,6S,8S,8aS)-6-(methoxycarbonyl)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2,2-dimethylbutyryl)oxy>naphthalene-1-carboxylate (143633-58-3)

Conditions	Yield
With pyridine; dmap at 90℃; for 16h;	92%

2,2-dimethylbutanoyl chloride (5856-77-9) + ((1S,6S)-2-[1,3]Dioxolan-2-yl-6-isopropyl-3,3-dimethyl-cyclohexyl)-methanol → 2,2-Dimethyl-butyric acid (1S,6S)-2-[1,3]dioxolan-2-yl-6-isopropyl-3,3-dimethyl-cyclohexylmethyl ester

Conditions	Yield
With dmap In pyridine	92%

2,2-dimethylbutanoyl chloride (5856-77-9) + 4-(Morpholinomethyl)quinolin-2-amine (1029128-03-7) → 2,2-dimethyl-N-(4-(morpholinomethyl)quinolin-2-yl)butanamide (1029126-67-7)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 16h;	92%

2,2-dimethylbutanoyl chloride (5856-77-9) + 6-methyl-4-phenyl-6H-1,3-thiazin-2-amine → 2,2-dimethyl-N-(6-methyl-4-phenyl-6H-1,3-thiazin-2-yl)butanamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1.16667h;	92%

2,2-dimethyl-6 (R)-(2-(8-(S)-hydroxy-2(S),6(R)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S))ethyl)-4(R)-(methyloxy-carbonyl)methyl-1,3-dioxane (272456-96-9) + 2,2-dimethylbutanoyl chloride (5856-77-9) → 2,2-dimethyl-6(R)-(2-(8(S)-(2,2-dimethylbutyryloxy)-2(S),6(R)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S))ethyl)-4(R)-(methyloxycarbonyl)methyl-1,3-dioxane (272456-97-0)

Conditions	Yield
With pyridine; lithium bromide In dichloromethane at 5 - 10℃; for 0.5 - 1h; Heating / reflux;	91%
With dmap; citric acid In pyridine; ethyl acetate

8-amino quinoline (578-66-5) + 2,2-dimethylbutanoyl chloride (5856-77-9) → 2,2-dimethyl-N-(quinolin-8-yl)butanamide (1215018-75-9)

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 0.5h; Inert atmosphere;	91%
With triethylamine In dichloromethane at 0 - 20℃;
With triethylamine In dichloromethane at 20℃;

2,2-dimethylbutanoyl chloride (5856-77-9) + 1-hydroxy-2-phenyl-5,6,7,7a-tetrahydro-3H-pyrrolizin-3-one → 5-oxo-6-phenyl-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl 2,2-dimethylbutanoate

Conditions	Yield
Stage #1: 1-hydroxy-2-phenyl-5,6,7,7a-tetrahydro-3H-pyrrolizin-3-one With triethylamine In dichloromethane for 0.5h; Stage #2: 2,2-dimethylbutanoyl chloride In dichloromethane at 0 - 20℃; for 12h;	91%

2,2-dimethylbutanoyl chloride (5856-77-9) + ((1R,2S,5R,6R)-6-Methoxymethoxymethyl-5-methyl-2-propyl-cyclohex-3-enyl)-methanol → 2,2-Dimethyl-butyric acid (1R,2S,5R,6R)-6-methoxymethoxymethyl-5-methyl-2-propyl-cyclohex-3-enylmethyl ester

Conditions	Yield
With dmap; triethylamine In dichloromethane for 20h; Ambient temperature;	90%

2,2-dimethylbutanoyl chloride (5856-77-9) + 3-(2,4-dimethyloxazol-5-yl)-3-hydroxy-2-(2-(2-bromophenyl)thiazol-4-yl)acrylonitrile → C23H22BrN3O3S

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 2h;	90%

2,2-dimethylbutanoyl chloride (5856-77-9) + 2-(4-fluorophenyl)-1-hydroxy-6,7,8,8a-tetrahydroindolizin-3(5H)-one → 2-(4-fluorophenyl)-3-oxo-3,5,6,7,8,8a-hexahydroindolizin-1-yl 2,2-dimethylbutanoate

Conditions	Yield
Stage #1: 2-(4-fluorophenyl)-1-hydroxy-6,7,8,8a-tetrahydroindolizin-3(5H)-one With triethylamine In dichloromethane for 0.5h; Stage #2: 2,2-dimethylbutanoyl chloride In dichloromethane at 0 - 20℃; for 12h;	90%

2-oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (209219-79-4) + 2,2-dimethylbutanoyl chloride (5856-77-9) → 2-oxo-3-tert-butoxycarbonylamino-5-(2,2-dimethylbutanoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Conditions	Yield
With pyridine In dichloromethane; 1,2-dichloro-ethane	89.8%

Upstream product

• 813-67-2 2,2-dimethyl-butanoic acid methyl ester 
• 595-37-9 2,2-dimethylbutyric acid 
• 1070-83-3 tert-Butylacetic acid 
• 98-88-4 benzoyl chloride 

Downstream Products

• 1185-33-7 2,2-Dimethyl-1-butanol 
• 66793-92-8 isopropyl-tert-pentyl-carbinol 
• 59517-40-7 2,2-Dimethyl-pentanoic acid [3-(2,2-dimethyl-butyrylamino)-phenyl]-amide 
• 1805-71-6 N-<2,2-Dimethyl-butyryl>-6-methyl-2,4-diisopentyl-anilid 
• 829-10-7 2,2-dimethyl-1-phenylbutanone 
• 52304-28-6 N-[3-(2,2-Dimethyl-butyrylamino)-phenyl]-2,2-dimethyl-butyramide 
• 595-37-9 2,2-dimethylbutyric acid 
• 122321-67-9 2,2-dimethylbutanoic acid (E)-1-[2-[2-(5,5-dimethyl-1,3-dioxan-2-yl)ethenyl]-3,5-dimethylphenyl]butyl ester 
• 122321-77-1 2,2-dimethylbutanoic acid (E)-1-[2-[2-(5,5-dimethyl-1,3-dioxan-2-yl)-ethenyl]-3,5-dimethylphenyl]phenylmethyl ester 
• 209222-11-7 1-[1-(2-toluoylmethyl)-2-oxo-5-(2,2-dimethylbutanoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea 
• 1029127-90-9 N-(5-bromo-4-methylpyridin-2-yl)-2,2-dimethylbutanamide 
• 1208117-16-1 N-(3,4-dimethyl-5-(morpholinosulfonyl)phenyl)-2,2-dimethylbutanamide 
• 1208117-21-8 C₁₈H₂₈N₂O₄S 
• 1208117-22-9 C₁₈H₂₈N₂O₄S 

Relevant articles and documents

Method for green synthesis of simvastatin side chain (by machine translation)

The method, comprises the following steps, adding :(1) dimethyl butanoic acid 2,2 - thionyl chloride, to the reaction vessel in a pot method, to carry out the esterification reaction ;(2) to obtain the product (1) dimethyl - 1 1-oxobutyl 3 -methyl propionate, through a solventless method, thereby reducing the material cost 3 - [(2,2 - without using any acid-binding agent) in the esterification step] and reducing the pollution, to the environment by a one-pot, method, at the same time without using any acid-tie-acid-acid-tie-acid-acid methyl ester, to carry out esterification reaction in a solvent concentration step, in the, esterification step by using a solventless method in a step, in the esterification reaction step, to obtain the, product (dimethyl) chloride, in the esterification step. (by machine translation)

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Insect chitinolytic β-N-acetyl-D-hexosaminidase, such as OfHex1 from Ostrinia furnacalis, is a potential target for insecticide design. Among the known OfHex1 inhibitors, Q2 is of great interest because it is the first non-carbohydrate inhibitor. In this study, we designed and synthesized a series of Q2 derivatives by replacing the thiadiazole and naphthalimide groups and changing the linker length. Compound 3m showed the best inhibitory activity with a Ki value of 0.34 μmol/L against OfHex1, which is about one-quarter that of Q2 (Ki = 1.4 μmol/L). Compound 6a showed the best inhibitory activity among the quinoline-containing derivatives (Ki = 2.3 μmol/L). Molecular docking indicated that although 3m, 6a, and Q2 binding the active pocket of OfHex1 in similar mode, compound 3m engaged better than the other compounds in intermolecular interaction with OfHex1.

2-Amino-5,6-difluorophenyl-1 H-pyrazole-Directed PdII Catalysis: Arylation of Unactivated β-C(sp3)-H Bonds

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