Product Name

  • Name

    3-Hydroxy-2,2-dimethylpropanal

  • EINECS 209-895-4
  • CAS No. 597-31-9
  • Article Data81
  • CAS DataBase
  • Density 0.964g/cm3
  • Solubility
  • Melting Point 30-33 °C
  • Formula C5H10 O2
  • Boiling Point 204.4°Cat760mmHg
  • Molecular Weight 102.133
  • Flash Point 60.3°C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 597-31-9 (3-Hydroxy-2,2-dimethylpropanal)
  • Hazard Symbols
  • Synonyms Hydracrylaldehyde,2,2-dimethyl- (6CI,7CI,8CI); 2,2-Dimethyl-3-hydroxypropanal;2,2-Dimethyl-3-hydroxypropionaldehyde; 2-(Hydroxymethyl)-2-methylpropanal;2-(Hydroxymethyl)isobutyraldehyde; 3-Hydroxy-2,2-dimethylpropanal;3-Hydroxy-2,2-dimethylpropionaldehyde; 3-Hydroxypivalaldehyde;Hydroxypivalaldehyde; Hydroxypivaldehyde; Pentaaldol; Pentaldol; a,a-Dimethyl-b-hydroxypropionaldehyde
  • PSA 37.30000
  • LogP 0.20380

Synthetic route

formaldehyd
50-00-0

formaldehyd

isobutyraldehyde
78-84-2

isobutyraldehyde

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Conditions
ConditionsYield
With water; potassium carbonate at 25℃; Aldol Condensation; Cooling with ice;92%
With triethylamine In water for 3h; Heating;91%
With sodium hydroxide at 80℃; for 0.516667h; Temperature; Aldol Condensation;91.14%
2-methyl-1,2-epoxypropane
558-30-5

2-methyl-1,2-epoxypropane

carbon monoxide
201230-82-2

carbon monoxide

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Conditions
ConditionsYield
Stage #1: 2-methyl-1,2-epoxypropane With rhodium (II) octanoate dimer; boron trifluoride at 50℃; for 0.5h; Inert atmosphere;
Stage #2: carbon monoxide With hydrogen at 90℃; under 75007.5 Torr; Reagent/catalyst; Temperature; Pressure;
90.3%
formaldehyd
50-00-0

formaldehyd

trimethylsilyl propenyl ether
19879-97-1

trimethylsilyl propenyl ether

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at 50℃;85%
formaline

formaline

isobutyraldehyde
78-84-2

isobutyraldehyde

A

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

B

2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate
1115-20-4

2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate

C

2,2-dimethyl-3-hydroxypropyl 2-methylpropionate
5919-84-6

2,2-dimethyl-3-hydroxypropyl 2-methylpropionate

D

2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

Conditions
ConditionsYield
With triethylamine at 65 - 90℃; for 0.666667h; Nitrogen atmosphere;A 62.4%
B 2%
C 0.26%
D 0.64%
2-(1,1-dimethyl-2-hydroxyethyl)-1,3-dithiane
219606-56-1

2-(1,1-dimethyl-2-hydroxyethyl)-1,3-dithiane

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Conditions
ConditionsYield
With acetic acid at 35℃; for 8h;42%
3-acetoxymethoxy-2,2-dimethyl-propionaldehyde

3-acetoxymethoxy-2,2-dimethyl-propionaldehyde

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Conditions
ConditionsYield
With sulfuric acid
potassium cyanide
151-50-8

potassium cyanide

A

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

B

2,4-dihydroxy-3,3-dimethyl-butyraldehyde
13199-26-3

2,4-dihydroxy-3,3-dimethyl-butyraldehyde

C

3-Deoxy-3,3-di-C-methyl-DL-glycero-tetrose hydrate

3-Deoxy-3,3-di-C-methyl-DL-glycero-tetrose hydrate

3-Deoxy-3,3-di-C-methyl-α-DL-glycero-tetrose
103203-99-2, 133094-80-1, 133094-96-9, 134932-06-2, 134932-07-3

3-Deoxy-3,3-di-C-methyl-α-DL-glycero-tetrose

Conditions
ConditionsYield
With hydrogen; Pd-BaSO4 1) water, 15 min, pH 7.7 2) pH 1.7; Multistep reaction. Title compound not separated from byproducts;
2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Conditions
ConditionsYield
With cyclohexanone; bis(cyclopentadienyl)dihydrozirconium at 150℃; for 8h;66 % Chromat.
With sodium nitrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; silver nitrate In water for 7h; Irradiation; regioselective reaction;
2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

A

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

B

2,2-dimethylmalonaldehyde
1185-34-8

2,2-dimethylmalonaldehyde

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethylsulfoxide-d6 at 23℃; Product distribution; product ratio was determined by 1H NMR;
formaldehyd
50-00-0

formaldehyd

isobutyraldehyde
78-84-2

isobutyraldehyde

potassium carbonate

potassium carbonate

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

4-hydroxy-5.5-dimethyl-2-<2-hydroxy-1.1-dimethyl-ethyl>-1.3-dioxane

4-hydroxy-5.5-dimethyl-2-<2-hydroxy-1.1-dimethyl-ethyl>-1.3-dioxane

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Conditions
ConditionsYield
under 14 Torr;
hydrogenchloride
7647-01-0

hydrogenchloride

bis-(3-hydroxy-2,2-dimethyl-propylidene)-hydrazine
59676-94-7

bis-(3-hydroxy-2,2-dimethyl-propylidene)-hydrazine

A

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

B

hydrazine salt

hydrazine salt

bis-(3-hydroxy-2,2-dimethyl-propylidene)-hydrazine
59676-94-7

bis-(3-hydroxy-2,2-dimethyl-propylidene)-hydrazine

sulfuric acid
7664-93-9

sulfuric acid

A

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

B

hydrazine salt

hydrazine salt

5,5-dimethyl-2-(1',1'-dimethyl-2'-hydroxyethyl)-4-hydroxy-1,3-dioxane
46329-82-2, 67081-75-8, 67081-77-0, 87194-52-3

5,5-dimethyl-2-(1',1'-dimethyl-2'-hydroxyethyl)-4-hydroxy-1,3-dioxane

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Conditions
ConditionsYield
In tetrahydrofuran at 65℃; for 3h;
at 26℃; for 28h; pH=2.5; aq. phosphate buffer;
In acetonitrile at 65℃; for 3h; Inert atmosphere;
calcium (R)-pantothenate
137-08-6

calcium (R)-pantothenate

A

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

B

carbon dioxide
124-38-9

carbon dioxide

C

calcium beta-alaninate
36321-40-1

calcium beta-alaninate

Conditions
ConditionsYield
With sodium hydroxide; potassium permanganate; sodium perchlorate In water at 25℃; for 8h; Kinetics; Further Variations:; Reagents; Temperatures;
3-hydroxy-4,4-dimethyltetrahydrofuran
15833-82-6

3-hydroxy-4,4-dimethyltetrahydrofuran

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: benzene
2: aq. H2SO4
View Scheme
formaldehyd
50-00-0

formaldehyd

isobutyraldehyde
78-84-2

isobutyraldehyde

A

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

B

2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate
1115-20-4

2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate

C

2,2-dimethyl-3-hydroxypropyl 2-methylpropionate
5919-84-6

2,2-dimethyl-3-hydroxypropyl 2-methylpropionate

D

2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

Conditions
ConditionsYield
triethylamine at 40 - 90℃; for 0.666667h; Aldol Condensation;
formaldehyd
50-00-0

formaldehyd

isobutyraldehyde
78-84-2

isobutyraldehyde

A

formic acid
64-18-6

formic acid

B

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

C

2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate
1115-20-4

2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate

D

2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

Conditions
ConditionsYield
triethylamine In water Product distribution / selectivity; Aldol Condensation;
formaldehyd
50-00-0

formaldehyd

isobutyraldehyde
78-84-2

isobutyraldehyde

A

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

B

2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate
1115-20-4

2,2-dimethyl-3-hydroxy-propyl 2,2-dimethyl-3-hydroxypropionate

C

2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

Conditions
ConditionsYield
With triethylamine In water at 40 - 90℃; for 0.666667h;
With triethylamine In water at 40 - 90℃; for 0.666667h;
formaldehyd
50-00-0

formaldehyd

isobutyraldehyde
78-84-2

isobutyraldehyde

A

5,5-dimethyl-2-(1',1'-dimethyl-2'-hydroxyethyl)-4-hydroxy-1,3-dioxane
46329-82-2, 67081-75-8, 67081-77-0, 87194-52-3

5,5-dimethyl-2-(1',1'-dimethyl-2'-hydroxyethyl)-4-hydroxy-1,3-dioxane

B

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Conditions
ConditionsYield
With potassium carbonate In water at 0 - 20℃;
formaldehyd
50-00-0

formaldehyd

isobutyraldehyde
78-84-2

isobutyraldehyde

A

methanol
67-56-1

methanol

B

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Conditions
ConditionsYield
With triethylamine
formaldehyd
50-00-0

formaldehyd

isovaleraldehyde
590-86-3

isovaleraldehyde

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Conditions
ConditionsYield
Aldol condensation;
methanol
67-56-1

methanol

2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

A

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

B

3-Hydroxy-2,2-dimethylpropanoic acid
4835-90-9

3-Hydroxy-2,2-dimethylpropanoic acid

C

Methyl 2,2-dimethyl-3-hydroxypropionate
14002-80-3

Methyl 2,2-dimethyl-3-hydroxypropionate

Conditions
ConditionsYield
With 1% Au-Pd/TiO2; oxygen; sodium hydroxide at 80℃; under 2250.23 Torr; for 4h;
formaldehyd
50-00-0

formaldehyd

2,2'-iminobis[ethanol]
111-42-2

2,2'-iminobis[ethanol]

isovaleraldehyde
590-86-3

isovaleraldehyde

A

2-(oxazolidin-3-yl)ethanol
20073-50-1

2-(oxazolidin-3-yl)ethanol

B

N-(2-hydroxyethyl)-2-isopropyloxazolidine
28770-01-6

N-(2-hydroxyethyl)-2-isopropyloxazolidine

C

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

D

3-(N,N-bis(2-hydroxyethyl)amino)-2,2-dimethylpropanal
1122612-55-8

3-(N,N-bis(2-hydroxyethyl)amino)-2,2-dimethylpropanal

Conditions
ConditionsYield
In water at 80℃; for 2h; Inert atmosphere; Cooling;
(2S*,4S*)-5,5-dimethyl-4-hydroxy-2-(1',1'-dimethyl-2'-hydroxyethyl)-1,3-dioxane

(2S*,4S*)-5,5-dimethyl-4-hydroxy-2-(1',1'-dimethyl-2'-hydroxyethyl)-1,3-dioxane

benzaldehyde
100-52-7

benzaldehyde

A

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

(2S*,4S*)-5,5-dimethyl-4-hydroxy-2-phenyl-1,3-dioxane

(2S*,4S*)-5,5-dimethyl-4-hydroxy-2-phenyl-1,3-dioxane

(2S*,4R*)-5,5-dimethyl-4-hydroxy-2-phenyl-1,3-dioxane

(2S*,4R*)-5,5-dimethyl-4-hydroxy-2-phenyl-1,3-dioxane

Conditions
ConditionsYield
With triethylamine at 0 - 65℃; for 6h; Inert atmosphere; Reflux; Optical yield = 16 %de; diastereoselective reaction;A 51 %Spectr.
B n/a
C n/a
(2S*,4S*)-5,5-dimethyl-4-hydroxy-2-(1',1'-dimethyl-2'-hydroxyethyl)-1,3-dioxane

(2S*,4S*)-5,5-dimethyl-4-hydroxy-2-(1',1'-dimethyl-2'-hydroxyethyl)-1,3-dioxane

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Conditions
ConditionsYield
With triethylamine; crotonaldehyde at 0 - 65℃; for 6h; Inert atmosphere; Reflux;62 %Spectr.
formaldehyd
50-00-0

formaldehyd

isobutyraldehyde
78-84-2

isobutyraldehyde

A

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

B

2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

Conditions
ConditionsYield
With tri-n-propylamine
methanol
67-56-1

methanol

isobutyraldehyde
78-84-2

isobutyraldehyde

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Conditions
ConditionsYield
With formaldehyd; triethylamine at 40 - 94℃;
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

2-butyl-2-ethylpropane-1,3-diol
115-84-4

2-butyl-2-ethylpropane-1,3-diol

2-(5-butyl-5-ethyl[1,3]dioxane-2-yl)-2-methylpropane-1-ol

2-(5-butyl-5-ethyl[1,3]dioxane-2-yl)-2-methylpropane-1-ol

Conditions
ConditionsYield
With nafion NR-50 In benzene Dean-Stark;99%
sodium cyanide
773837-37-9

sodium cyanide

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

pantolactone
79-50-5

pantolactone

Conditions
ConditionsYield
With sulfuric acid for 3h; pH=9.5; Reflux;98.9%
With sulfuric acid In water at 100℃; for 1h;86.9%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

1,2,3,4-tetrahydronaphthalen-2-one
530-93-8

1,2,3,4-tetrahydronaphthalen-2-one

2,3-dihydro-2,2-dimethyl-1H-benzo[f]chromene
1011489-51-2

2,3-dihydro-2,2-dimethyl-1H-benzo[f]chromene

Conditions
ConditionsYield
With hydrogenchloride In formic acid at 5 - 10℃; for 1h;96.4%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

β-naphthol
135-19-3

β-naphthol

3,3-dimethyl-4-(2-hydroxy-1-naphthyl)benzo[f]chroman

3,3-dimethyl-4-(2-hydroxy-1-naphthyl)benzo[f]chroman

Conditions
ConditionsYield
With hydrogenchloride; acetic acid at 50 - 60℃; for 4h;95%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

hydrogen cyanide
74-90-8

hydrogen cyanide

pantolactone
79-50-5

pantolactone

Conditions
ConditionsYield
Stage #1: 2,2-dimethyl-3-hydroxypropionaldehyde; hydrogen cyanide In water at 0 - 10℃; for 0.25h;
Stage #2: With sulfuric acid for 1h; Reflux;
93.1%
Verseifung des Reaktionsprodukts mit Salzsaeure;
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

3-Hydroxy-2,2-dimethylpropanoic acid
4835-90-9

3-Hydroxy-2,2-dimethylpropanoic acid

Conditions
ConditionsYield
Stage #1: 2,2-dimethyl-3-hydroxypropionaldehyde With sodium hydroxide at 85 - 95℃; for 2h;
Stage #2: With ammonium hydroxide; H1044 at 60℃; for 8h; pH=7 - 9;
91%
With phosphotungstic acid; dihydrogen peroxide In water at 55℃; for 2h; Temperature; Reagent/catalyst; Time;85%
With sodium hydroxide; oxygen; palladium/alumina at 39.85℃; under 760 Torr; Kinetics; Further Variations:; Temperatures;
Multi-step reaction with 2 steps
1: water; aluminium amalgam
2: potassium permanganate
View Scheme
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran90%
With aluminium amalgam; water
With sodium amalgam; water
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Pentaerythritol
115-77-5

Pentaerythritol

3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane
1455-42-1

3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane

Conditions
ConditionsYield
Stage #1: 2,2-dimethyl-3-hydroxypropionaldehyde; Pentaerythritol; sulfuric acid In water; xylene at 60℃; for 14h;
Stage #2: With sodium hydroxide Conversion of starting material;
89%
Stage #1: 2,2-dimethyl-3-hydroxypropionaldehyde; Pentaerythritol; hydrogenchloride In water at 70℃; for 8h;
Stage #2: With sodium hydroxide at 40℃; pH=6.5; Conversion of starting material;
83%
sulfuric acid In water at 60℃; for 6h; Conversion of starting material;80%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

2,3-dimethyl-2,3-diaminobutane
20485-44-3

2,3-dimethyl-2,3-diaminobutane

2-(4',4',5',5'-tetramethylimidazolidine-2'-yl)-2-methylpropanol
1309974-80-8

2-(4',4',5',5'-tetramethylimidazolidine-2'-yl)-2-methylpropanol

Conditions
ConditionsYield
In chloroform for 24h; Molecular sieve; Reflux;87%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

methyl 2-(bromomethyl)propenoate
4224-69-5

methyl 2-(bromomethyl)propenoate

4,6-Dihydroxy-5,5-dimethyl-2-methylene-hexanoic acid methyl ester
138832-37-8

4,6-Dihydroxy-5,5-dimethyl-2-methylene-hexanoic acid methyl ester

Conditions
ConditionsYield
With indium In water for 5h; Ambient temperature;85%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

allyl bromide
106-95-6

allyl bromide

2,2-dimethyl-5-hexen-1,3-diol
138832-34-5

2,2-dimethyl-5-hexen-1,3-diol

Conditions
ConditionsYield
With indium In water for 3h; Ambient temperature;85%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

1,1,1-tri(hydroxymethyl)propane
77-99-6

1,1,1-tri(hydroxymethyl)propane

trans-2-(5-ethyl-5-hydroxymethyl-1,3-dioxane-2-yl)-2-methylpropane-1-ol

trans-2-(5-ethyl-5-hydroxymethyl-1,3-dioxane-2-yl)-2-methylpropane-1-ol

Conditions
ConditionsYield
hydrogenchloride In water at 60℃; for 5h; Product distribution / selectivity;84%
toluene-4-sulfonic acid In water at 55 - 70℃; for 1 - 3h; pH=1.3; Product distribution / selectivity;30%
hydrogenchloride In water at 60℃; for 5h; Product distribution / selectivity;
3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

isocyanoacetic acid methyl ester
39687-95-1

isocyanoacetic acid methyl ester

C18H25N5O3

C18H25N5O3

Conditions
ConditionsYield
Stage #1: 3-phenyl-propionaldehyde; 2,2-dimethyl-3-hydroxypropionaldehyde With ammonium hydroxide In toluene for 2h; Sonication;
Stage #2: isocyanoacetic acid methyl ester With trimethylsilylazide In toluene Sonication; diastereoselective reaction;
83%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

2,2-dimethyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-propanal
52113-84-5

2,2-dimethyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-propanal

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; Addition;80%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

(methoxymethyl)triphenylphosphonium chloride
4009-98-7

(methoxymethyl)triphenylphosphonium chloride

(E)-4-Methoxy-2,2-dimethyl-but-3-en-1-ol

(E)-4-Methoxy-2,2-dimethyl-but-3-en-1-ol

Conditions
ConditionsYield
Stage #1: (methoxymethyl)triphenylphosphonium chloride With potassium tert-butylate In diethyl ether for 1.5h; Metallation;
Stage #2: 2,2-dimethyl-3-hydroxypropionaldehyde In diethyl ether at 20℃; for 10h; olefination;
80%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

ethyl trans-4,4-dimethyl-5-hydroxypent-2-enoate
158045-09-1

ethyl trans-4,4-dimethyl-5-hydroxypent-2-enoate

Conditions
ConditionsYield
In benzene at 80℃;78%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

pivalaldehyde
630-19-3

pivalaldehyde

Conditions
ConditionsYield
With triethyl borane; trifluorormethanesulfonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane a) -30 deg C, 30 min, b) room temperature, 6 h;74%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

malononitrile
109-77-3

malononitrile

6-amino-3,3-dimethyl-2,4-dihydropyran-5-carbonitrile
337310-91-5

6-amino-3,3-dimethyl-2,4-dihydropyran-5-carbonitrile

Conditions
ConditionsYield
With sodium tetrahydroborate In isopropyl alcohol at 0 - 20℃; for 4h;74%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

2,7-Dihydroxynaphthalene
582-17-2

2,7-Dihydroxynaphthalene

1,12-dihydroxy-14-(2-hydroxymethylprop-2-yl)-14H-dibenzo[a,j]xanthene

1,12-dihydroxy-14-(2-hydroxymethylprop-2-yl)-14H-dibenzo[a,j]xanthene

Conditions
ConditionsYield
With hydrogenchloride; acetic acid at 50 - 60℃; for 4h;72%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

3-hydroxy-2,2-dimethylpropionaldoxime
36559-87-2

3-hydroxy-2,2-dimethylpropionaldoxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; water; potassium carbonate In ethanol at 70℃; for 48h; Cooling with ice;71%
With hydroxylamine
With hydroxylamine hydrochloride
1.3-propanedithiol
109-80-8

1.3-propanedithiol

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

2-(1,1-dimethyl-2-hydroxyethyl)-1,3-dithiane
219606-56-1

2-(1,1-dimethyl-2-hydroxyethyl)-1,3-dithiane

Conditions
ConditionsYield
With boron trifluoride diethyl etherate thioacetalization;70%
With boron trifluoride diethyl etherate at 20℃;
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

C5H11(2)HO2
344948-08-9

C5H11(2)HO2

Conditions
ConditionsYield
With lithium aluminium deuteride In tetrahydrofuran at 65℃; for 1.5h;70%
methanol
67-56-1

methanol

2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

Methyl 2,2-dimethyl-3-hydroxypropionate
14002-80-3

Methyl 2,2-dimethyl-3-hydroxypropionate

Conditions
ConditionsYield
With sodium methylate; potassium iodide at 17℃; electrooxidation;68%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

aniline
62-53-3

aniline

N-phenyl-2-(hydroxymethyl)-2-methylpropylamine
94844-02-7

N-phenyl-2-(hydroxymethyl)-2-methylpropylamine

Conditions
ConditionsYield
With sodium cyanoborohydride; zinc(II) chloride In methanol for 36h; Ambient temperature;66%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

N-cyclohexyl-hydroxylamine
2211-64-5

N-cyclohexyl-hydroxylamine

3-(cyclohexylimino)-2,2-dimethylpropanol N-oxide

3-(cyclohexylimino)-2,2-dimethylpropanol N-oxide

Conditions
ConditionsYield
In benzene for 5h; Heating;66%
2,2-dimethyl-3-hydroxypropionaldehyde
597-31-9

2,2-dimethyl-3-hydroxypropionaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

3-Hydroxy-2,2-dimethylpropanal dimethyl acetal
87395-22-0

3-Hydroxy-2,2-dimethylpropanal dimethyl acetal

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol for 24h;66%

3-Hydroxy-2,2-dimethylpropanal Chemical Properties

Molecular Structure of 3-Hydroxy-2,2-dimethylpropanal (CAS NO.597-31-9):

IUPAC Name: 3-Hydroxy-2,2-dimethylpropanal 
Molecular Formula: C5H10O2
Molecular Weight: 102.13
EINECS: 209-895-4 
XLogP3-AA: -0.1
H-Bond Donor: 1
H-Bond Acceptor: 2 
Index of Refraction: 1.421
Molar Refractivity: 26.9 cm3
Molar Volume: 105.9 cm3
Surface Tension: 31.9 dyne/cm
Density: 0.964 g/cm3
Flash Point: 60.3 °C
Enthalpy of Vaporization: 51.26 kJ/mol
Boiling Point: 204.4 °C at 760 mmHg
Vapour Pressure: 0.0632 mmHg at 25 °C
Canonical SMILES: CC(C)(CO)C=O
InChI: InChI=1S/C5H10O2/c1-5(2,3-6)4-7/h3,7H,4H2,1-2H3
InChIKey: JJMOMMLADQPZNY-UHFFFAOYSA-N

3-Hydroxy-2,2-dimethylpropanal Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1600mg/kg (1600mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. OTS0533626,
mouse LD50 oral 3200mg/kg (3200mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. OTS0533626,
rat LD50 intraperitoneal 800mg/kg (800mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. OTS0533626,
rat LD50 oral 3200mg/kg (3200mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. OTS0533626,

3-Hydroxy-2,2-dimethylpropanal Specification

 3-Hydroxy-2,2-dimethylpropanal (CAS NO.597-31-9), its Synonyms are 2,2-Dimethyl-3-hydroxypropanal ; 2,2-Dimethyl-beta-hydroxypropionaldehyde ; 2-(Hyroxymethyl)-2-methylpropanal ; 3-Hydroxypivalaldehyde ; Hydracrylaldehyde, 2,2-dimethyl- ; Hydroxypivalaldehyde ; Hydroxypivaldehyde ; Pentaaldol ; Pentaldol ; Propanal, 3-hydroxy-2,2-dimethyl- ; Propionaldehyde, 3-hydroxy-2,2-dimethyl- ; alpha,alpha-Dimethyl-beta-hydroxypropionaldehyde ; Hydracrylaldehyde, 2,2-dimethyl- (6CI,7CI,8CI) ; Propanal, 2,2-dimethyl-3-hydroxy- .

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