Conditions | Yield |
---|---|
In tetrahydrofuran 1.) -30 deg C, 1 h, 2.) 0 deg C, 1 h; | 91% |
Conditions | Yield |
---|---|
copper(l) iodide In tetrahydrofuran at 0℃; for 0.25h; | 80% |
Conditions | Yield |
---|---|
Stage #1: 2-methyl-2-butylchloride With magnesium In tetrahydrofuran; toluene at 50 - 90℃; for 2h; Stage #2: carbon dioxide In tetrahydrofuran; toluene at 35 - 45℃; for 1h; Stage #3: With hydrogenchloride In tetrahydrofuran; water; toluene for 4h; Reflux; | 72% |
(i) Mg, THF, (ii) /BRN= 1900390/; Multistep reaction; |
Conditions | Yield |
---|---|
With Ph4(CO)12; sulfuric acid at 20℃; under 760.051 Torr; for 1h; Carbonylation; | 68% |
With sulfuric acid; water at 20℃; under 760.051 Torr; Product distribution; Carbonylation; hydrolysis; | 70 % Chromat. |
Conditions | Yield |
---|---|
With sulfuric acid; pentane anschliessend mit Eiswasser; |
2,2-dimethyl-but-3-enoic acid
2,2-dimethylbutyric acid
Conditions | Yield |
---|---|
With ethyl acetate; platinum Hydrogenation; |
Conditions | Yield |
---|---|
With chromium(III) oxide; sulfuric acid | |
Multi-step reaction with 2 steps 1: copper / 250 - 300 °C View Scheme |
2,2-dimethylbutanenitrile
2,2-dimethylbutyric acid
Conditions | Yield |
---|---|
With hydrogenchloride at 100 - 120℃; | |
(i) H2SO4, (ii) aq. NaNO2; Multistep reaction; |
2,2-dimethyl-n-butyramide
2,2-dimethylbutyric acid
Conditions | Yield |
---|---|
With nitrosylsulfuric acid; sulfuric acid |
4,4-dimethyl-hexan-3-one
2,2-dimethylbutyric acid
Conditions | Yield |
---|---|
With potassium dichromate; sulfuric acid | |
With alkaline KMNO4 |
Conditions | Yield |
---|---|
With hydrogen bromide at 180℃; |
4,4-dimethyl-2-oxo-pentanoic acid
2,2-dimethylbutyric acid
Conditions | Yield |
---|---|
With sulfuric acid; dichromate anion |
4-t-amylphenol
A
2,2-dimethylbutyric acid
B
4,4-dimethyl-2-oxo-pentanoic acid
Conditions | Yield |
---|---|
With potassium permanganate |
1,1-dimethylpropylmagnesium chloride
methylammonium carbonate
2,2-dimethylbutyric acid
Conditions | Yield |
---|---|
With diethyl ether |
Conditions | Yield |
---|---|
With di-tert-butyl peroxide at 170℃; under 44130.5 Torr; | |
With oxygen; 1,2-di(benzylidene)hydrazine at 250℃; under 625182 - 720798 Torr; |
ethene
isobutyric Acid
benzaldehyde benzylidenehydrazone
A
2,2-dimethylbutyric acid
B
2,2-dimethylhexanoic acid
Conditions | Yield |
---|---|
at 250 - 275℃; under 147102 - 698732 Torr; |
Conditions | Yield |
---|---|
With sulfuric acid; pentane anschliessend mit Eiswasser; |
Conditions | Yield |
---|---|
With boron trifluoride; water; propionic acid under 76000 Torr; | |
With water; silver trifluoromethanesulfonate In hexane at 150℃; under 37503 Torr; for 18h; Koch carbonylation; | 10 % Chromat. |
Conditions | Yield |
---|---|
With sodium amide at 150 - 250℃; |
Conditions | Yield |
---|---|
With phosphoric acid |
1-Heptene
carbon monoxide
A
2,2-dimethylbutyric acid
B
2-methyl-2-ethylpentanoic acid
C
2,2-dimethyl-n-valeric acid
D
2,2-dimethylhexanoic acid
E
Trimethylacetic acid
Conditions | Yield |
---|---|
With sulfuric acid; silver(l) oxide at 30℃; under 760 Torr; for 4h; Product distribution; other catalyst; | A 4 % Turnov. B 25 % Turnov. C 4 % Turnov. D 66 % Turnov. E 1 % Turnov. |
3-methylbutyric acid
carbon monoxide
A
2,2-dimethylbutyric acid
B
4-Methylpentanoic acid
Conditions | Yield |
---|---|
With hydrogen; ruthenium(IV) oxide; methyl iodide at 220℃; under 205200 Torr; Yield given. Yields of byproduct given; |
1-hexene
carbon monoxide
A
2-methyl-2-ethylbutanoic acid
B
2,2-dimethylbutyric acid
C
2-ethylvaleric acid
D
2,2-dimethyl-n-valeric acid
E
Trimethylacetic acid
Conditions | Yield |
---|---|
With sulfuric acid; silver(l) oxide at 30℃; under 760 Torr; for 4h; Product distribution; other catalyst; | A 23 % Turnov. B 21 % Turnov. C 7 % Turnov. D 44 % Turnov. E 5 % Turnov. |
Conditions | Yield |
---|---|
With sulfuric acid 1.) acetic acid, 5 deg C, 3 min, 2.) 5 deg C, 3.0 h; Yield given. Multistep reaction; |
n-hexan-2-ol
carbon monoxide
A
2-methyl-2-ethylbutanoic acid
B
2,2-dimethylbutyric acid
C
2-ethylvaleric acid
D
2-methylhexanoic acid
E
2,2-dimethyl-n-valeric acid
F
Trimethylacetic acid
Conditions | Yield |
---|---|
With sulfuric acid; silver(l) oxide at 30℃; under 760 Torr; for 4h; Product distribution; | A 34 % Turnov. B 5 % Turnov. C 9 % Turnov. D 8 % Turnov. E 43 % Turnov. F 1 % Turnov. |
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
1-penten
carbon monoxide
A
2-Ethylbutanoic acid
B
2,2-dimethylbutyric acid
C
Trimethylacetic acid
Conditions | Yield |
---|---|
With sulfuric acid; silver(l) oxide at 30℃; under 760 Torr; for 4h; Product distribution; | A 9 % Turnov. B 74 % Turnov. C 7 % Turnov. |
(1,3-dimethylbutyl)benzene
A
2,2-dimethylbutyric acid
B
1,3,3-trimethylindane
C
benzene
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; carbon monoxide; 2-Methyl-1-butene In tetrachloromethane under 79800.1 Torr; for 3h; Ambient temperature; Title compound not separated from byproducts; | A 5 % Chromat. B 27 % Chromat. C 29 % Chromat. |
2,2-dimethylbutyric acid
tert-butylisonitrile
3-nitro-benzaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethylbutyric acid; 3-nitro-benzaldehyde With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; magnesium sulfate In chloroform at -20℃; for 0.166667h; Passerini Condensation; Inert atmosphere; Schlenk technique; Stage #2: tert-butylisonitrile In chloroform at -20℃; for 36h; Passerini Condensation; Inert atmosphere; Schlenk technique; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
In toluene at 110℃; for 16h; Schlenk technique; Inert atmosphere; | 99% |
n-butyllithium
2,2-dimethylbutyric acid
Conditions | Yield |
---|---|
Stage #1: n-butyllithium; 2,2-dimethylbutyric acid In hexane at -80℃; Schlenk technique; Inert atmosphere; Stage #2: In hexane at 20℃; for 2h; Schlenk technique; Inert atmosphere; | 99% |
2,2-dimethylbutyric acid
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethylbutyric acid With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.5h; Stage #2: 6 (R)-[2-(8'(S)-hydroxy-2'(S),6'(R)-dimethyl-1',2',6',7',8',8'a (R)-hexahydronaphthyl-1'(S))ethyl]-4 (R)-(dimethyl-tert-butylsilyloxy)-3,4,5,6-tetrahydro-2H-pyran-2-on With C24H27O2P; N,N-dimethyl-aniline at 0 - 20℃; for 10h; | 97% |
2,2-dimethylbutyric acid
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethylbutyric acid With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 0.5h; Stage #2: 6 (R)-[2-(8'(S)-hydroxy-2'(S),6'(R)-dimethyl-l',2',6',7',8',8a'(R)-hexahydronaphthyl-1' (S)) ethyl]-4 (R)-(dimethyl-tert-butylsilyloxy)-3,4,5,6-tetrahydro-2H-pyran-2-on at 0 - 20℃; for 10h; | 97% |
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; 1,1,1,3',3',3'-hexafluoro-propanol; N-[2-(phenylsulfanyl)ethyl]acetamide; HO4P(2-)*Na(1+)*7H2O; silver carbonate at 120℃; for 12h; Reagent/catalyst; | 96% |
Conditions | Yield |
---|---|
With sulfuric acid In benzene for 3h; Reflux; | 96% |
Conditions | Yield |
---|---|
mercury(II) diacetate; mercury dichloride In toluene La was suspended in toluene, 2,2-dimethylbutyric acid was added, soln. was heated at reflux for 30 min, HgCl2 and Hg(OAc)2 were added, soln. washeated to reflux and stirred for 3 h; ppt. was filtered off, washed with hexane, heated for 30 min at 175°C, and dried at 5E-4 Torr at 120°C; elem. anal.; | 94% |
1,3-Benzothiazole
2,2-dimethylbutyric acid
2-(tert-pentyl)benzo[d]thiazole
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; silver nitrate In dichloromethane; water at 20℃; for 8h; | 93% |
With ammonium peroxydisulfate; anthocyanin In dichloromethane; water at 20℃; Minisci Aromatic Substitution; Irradiation; Green chemistry; | 89% |
With sodium phosphate dibasic dodecahydrate; 9-(2-mesityl)-10-methylacridinium perchlorate In water; acetonitrile at 20℃; for 36h; Irradiation; | 80% |
2,2-dimethylbutyric acid
{(2S,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-[2-(4-methoxy-phenoxy)-ethyl]-3-propyl-tetrahydro-pyran-4-yl}-methanol
2,2-Dimethyl-butyric acid (2S,3S,4S,5R,6S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-[2-(4-methoxy-phenoxy)-ethyl]-3-propyl-tetrahydro-pyran-4-ylmethyl ester
Conditions | Yield |
---|---|
With dmap; methanesulfonyl chloride; triethylamine In dichloromethane | 92% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; | 92% |
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 0.5h; | 78% |
With dmap; diisopropyl-carbodiimide In dichloromethane |
Conditions | Yield |
---|---|
In toluene mixt. 2,2-dimethylbutanoic acid (6 equiv.) and zinc oxide (4 equiv.) and toluene heated with stirring for 3 h (water removed); product filtered, solvent removed from filtrate, purified by recrystn.;elem. anal.; | 91% |
2,2-dimethylbutyric acid
phenylpropyolic acid
3,3-Dimethyl-1-phenylpent-1-in
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; copper; silver nitrate In water; acetonitrile at 110℃; for 12h; | 91% |
2,2-dimethylbutyric acid
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; palladium diacetate at 40℃; for 2h; regioselective reaction; | 91% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; copper; silver nitrate In water; acetonitrile at 90℃; for 12h; | 89% |
Conditions | Yield |
---|---|
mercury(II) diacetate; mercury dichloride In toluene Nd was suspended in toluene, 2,2-dimethylbutyric acid was added, soln. was heated at reflux for 30 min, HgCl2 and Hg(OAc)2 were added, soln. washeated to reflux and stirred for 3 h; ppt. was filtered off, washed with hexane, heated for 30 min at 175°C, and dried at 5E-4 Torr at 120°C; elem. anal.; | 88% |
2,2-dimethylbutyric acid
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; palladium diacetate at 40℃; for 2h; regioselective reaction; | 87% |
5-methyl-6-cyano-7-hydrazino-2-oxo-2H-pyrano[2,3-b]pyridine-3-carboxylic acid
2,2-dimethylbutyric acid
C17H16N4O4
Conditions | Yield |
---|---|
Heating; | 85% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; silver nitrate In dichloromethane; water at 20℃; for 8h; | 85% |
Conditions | Yield |
---|---|
In dichloromethane; acetonitrile byproducts: acetic acid; soln. Mn complex in MeCN was treated with soln. EtMe2CCOOH in CH2Cl2 andstirred overnight; solvent was removed in vacuo, residue was dissolved in toluene and evapd. to dryness (repeated 3 times), residue was dissolved in CH2Cl2, filtered, MeNO2 was added, 4°C for 4 days, ppt. was filtered, washed with MeNO2, dried in vacuo; elem. anal.; | 83% |
2,2-dimethylbutyric acid
6-nitrobenzo[d]thiazole
6-nitro-2-(tert-pentyl)benzo[d]thiazole
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; silver nitrate In dichloromethane; water at 20℃; for 8h; | 83% |
2,2-dimethylbutyric acid
N,O-dimethylhydroxylamine*hydrochloride
lithium phenylacetylide
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethylbutyric acid With oxalyl dichloride Stage #2: N,O-dimethylhydroxylamine*hydrochloride With pyridine Stage #3: lithium phenylacetylide | 82% |
2,2-dimethylbutyric acid
Conditions | Yield |
---|---|
at 200℃; for 50h; Inert atmosphere; | 81% |
Conditions | Yield |
---|---|
With bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation; Schlenk technique; | 81% |
IUPAC Name: 2,2-dimethylbutanoic acid
Empirical Formula: C6H12O2
Molecular Weight: 116.1583
Canonical SMILES: CCC(C)(C)C(=O)O
InChI: InChI=1S/C6H12O2/c1-4-6(2,3)5(7)8/h4H2,1-3H3,(H,7,8)
InChIKey: VUAXHMVRKOTJKP-UHFFFAOYSA-N
Melting Point: -14 °C
Decomposition: 176-178 ºC
EINECS: 209-865-0
Index of Refraction: 1.426
Molar Refractivity: 31.37 cm3
Molar Volume: 122.2 cm3
Surface Tension: 30.6 dyne/cm
Density: 0.95 g/cm3
Flash Point: 80.6 °C
Enthalpy of Vaporization: 46.69 kJ/mol
Boiling Point: 187.3 °C at 760 mmHg
Vapour Pressure: 0.286 mmHg at 25 °C
Product Categories of 2,2-Dimethylbutyric acid (CAS NO.595-37-9): Organic acids; C6; Carbonyl Compounds; Carboxylic Acids
2,2-Dimethylbutyric acid is mainly used in medicine intermediate ,pesticide intermediate,and lubricant, etc.
Hazard Codes:Xi
Risk Statements:
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements:
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37: Wear suitable protective clothing and gloves
S36: Wear suitable protective clothing
2,2-Dimethylbutyric acid (CAS NO.595-37-9), its Synonyms are Butanoic acid, 2,2-dimethyl- ;.alpha., .alpha.-Dimethylbutyric acid ;.alpha.,.alpha.-Dimethylbutanoic acid .
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