2,2-Dimethylbutyryl chloride supplier

Name
2,2-Dimethylbutyryl chloride
EINECS 227-478-5
CAS No. 5856-77-9
Article Data45
CAS DataBase
Density 0.988 g/cm³
Solubility Reacts with water. Soluble in chloroform and ethyl acetate.
Melting Point
Formula C₆H₁₁ClO
Boiling Point 131.8 °C at 760 mmHg
Molecular Weight 134.606
Flash Point 30.2 °C
Transport Information
Appearance clear to yellowish liquid
Safety 26-36/37/39-45
Risk Codes 10-34
Molecular Structure
Hazard Symbols C
Synonyms Butyrylchloride, 2,2-dimethyl- (6CI,8CI);2,2-Dimethylbutanoyl chloride;2,2-Dimethylbutyric acid chloride;
PSA 17.07000
LogP 2.18800

Synthetic route

: 595-37-9
2,2-dimethylbutyric acid

: 5856-77-9
2,2-dimethylbutanoyl chloride

Conditions

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

: 1070-83-3
tert-Butylacetic acid

: 5856-77-9
2,2-dimethylbutanoyl chloride

Conditions

Conditions	Yield
With thionyl chloride

: 1070-83-3
tert-Butylacetic acid

: 98-88-4
benzoyl chloride

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 813-67-2
2,2-dimethyl-butanoic acid methyl ester

: 5856-77-9
2,2-dimethylbutanoyl chloride

Conditions

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

: 809273-56-1
3-amino-4-[(cyclohexylmethyl)amino]-benzonitrile

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 809273-57-2
1-(cyclohexylmethyl)-2-(1,1-dimethylpropyl)-1H-benzimidazole-5-carbonitrile

Conditions

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

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 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

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

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 95837-11-9
5-amino-2,3-dihydrofuro<3,2-b>pyridine

: 1029128-34-4
N-(2,3-dihydrofuro[3,2-b]pyridin-5-yl)-2,2-dimethylbutyramide

Conditions

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

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 18531-99-2
(S)-[1,1']-binaphthalenyl-2,2'-diol

: (S)-2-(2,2-dimethylbutyryl)oxy-2'-hydroxy-1,1'-binaphthyl

Conditions

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

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 3,3',4,4'-tetraaminobiphenyl tetrahydrochloride dihydrate

: 1184267-88-6
3,3',4,4'-tetra(2,2-dimethylbutyrylamido)biphenyl

Conditions

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%

: 2935-90-2
Methyl 3-mercaptopropionate

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 938063-63-9
methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate

Conditions

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

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 127655-56-5
2-(2,4-dichlorophenyl)-1-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-3-one

: 6-(2,4-dichlorophenyl)-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl 2,2-dimethylbutanoate

Conditions

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%

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 5407-87-4
2-Amino-4,6-dimethylpyridine

: 1029127-97-6
N-(4,6-dimethylpyridin-2-yl)-2,2-dimethylbutanamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane	95%

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 60-24-2
2-hydroxyethanethiol

: C8H16O2S

Conditions

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

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 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

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%

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 102299-03-6
(+)-ethyl (1S,2S,4aR,6S,8S,8aS)-6-(carboxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-8-hydroxy-2-methylnaphthalene-1-carboxylate

: 143633-58-3
(+)-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

Conditions

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

: 5856-77-9
2,2-dimethylbutanoyl chloride

: ((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

Conditions	Yield
With dmap In pyridine	92%

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 1029128-03-7
4-(Morpholinomethyl)quinolin-2-amine

: 1029126-67-7
2,2-dimethyl-N-(4-(morpholinomethyl)quinolin-2-yl)butanamide

Conditions

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

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 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

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

: 272456-96-9
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

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 272456-97-0
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

Conditions

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

: 578-66-5
8-amino quinoline

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 1215018-75-9
2,2-dimethyl-N-(quinolin-8-yl)butanamide

Conditions

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℃;

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 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

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%

: 5856-77-9
2,2-dimethylbutanoyl chloride

: ((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

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

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 3-(2,4-dimethyloxazol-5-yl)-3-hydroxy-2-(2-(2-bromophenyl)thiazol-4-yl)acrylonitrile

: C23H22BrN3O3S

Conditions

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

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 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

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%

: 209219-79-4
2-oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 2-oxo-3-tert-butoxycarbonylamino-5-(2,2-dimethylbutanoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Conditions

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

2,2-Dimethylbutyryl chloride Specification

The 2,2-Dimethylbutyryl chloride is an organic compound with the formula C₆H₁₁ClO. The IUPAC name of this chemical is 2,2-dimethylbutanoyl chloride. With the CAS registry number 5856-77-9, it is also named as butanoyl chloride, 2,2-dimethyl-. Besides, it should be stored in a dark cool and dry place. It is used as a pharmaceutical intermediate.

Physical properties about 2,2-Dimethylbutyryl chloride are: (1)ACD/LogP: 2.22; (2)ACD/LogD (pH 5.5): 2.22; (3)ACD/LogD (pH 7.4): 2.22; (4)ACD/BCF (pH 5.5): 28.5; (5)ACD/BCF (pH 7.4): 28.5; (6)ACD/KOC (pH 5.5): 382.79; (7)ACD/KOC (pH 7.4): 382.79; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 17.07 Å²; (11)Index of Refraction: 1.423; (12)Molar Refractivity: 34.69 cm³; (13)Molar Volume: 136.1 cm³; (14)Polarizability: 13.75×10^-24cm³; (15)Surface Tension: 26.7 dyne/cm; (16)Density: 0.988 g/cm³; (17)Flash Point: 30.2 °C; (18)Enthalpy of Vaporization: 36.94 kJ/mol; (19)Boiling Point: 131.8 °C at 760 mmHg; (20)Vapour Pressure: 9.14 mmHg at 25°C.

Preparation: this chemical can be prepared by 2,2-dimethyl-butyric acid. This reaction will need reagent oxalyl chloride, DMF and solvent CH₂Cl₂ by heating.

Uses of 2,2-Dimethylbutyryl chloride: it can be used to produce 3,3-dimethyl-5-tetradecyn-4-one at temperature of 80 °C. It will need reagent CuI, triethylamine and solvent toluene with reaction time of 6 hours. The yield is about 50%.

When you are using this chemical, please be cautious about it as the following:
It is flammable. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is can cause burns. When you are using it, wear suitable gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: ClC(=O)C(C)(C)CC
(2)InChI: InChI=1/C6H11ClO/c1-4-6(2,3)5(7)8/h4H2,1-3H3
(3)InChIKey: LDJUYMIFFNTKOI-UHFFFAOYAU
(4)Std. InChI: InChI=1S/C6H11ClO/c1-4-6(2,3)5(7)8/h4H2,1-3H3
(5)Std. InChIKey: LDJUYMIFFNTKOI-UHFFFAOYSA-N

Product Name

2,2-Dimethylbutyryl chloride

Synthetic route

2,2-Dimethylbutyryl chloride Specification

Related Products

Hot Products