75-84-3

Basic information

• Product Name: 2,2-Dimethyl-1-propanol
• Synonyms: 2,2,2-Trimethylethanol;2,2-Dimethyl-1-propanol;2,2-Dimethylpropyl alcohol;Neoamyl alcohol;Neopentanol;Neopentyl alcohol;tert-Butylcarbinol;a,a-Dimethylpropanol
• CAS NO: 75-84-3
• Molecular Formula: C₅H₁₂O
• Molecular Weight: 88.14818
• EINECS: 200-907-3
• Mol File: 75-84-3.mol
• Article Data: 106

Chemical Properties

• Melting Point: 52-53℃
• Boiling Point: 113.1 °C at 760 mmHg
• Flash Point: 36.7 °C
• Appearance: colorless waxy crystalline solid
• Density: 0.811 g/cm³
• Vapor Pressure: 10.8mmHg at 25°C
• Refractive Index: 1.406
• PKA: 15.24±0.10(Predicted)
• Water Solubility: 3.5 g/100 mL at 25℃
• CAS DataBase Reference: 2,2-Dimethyl-1-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethyl-1-propanol(75-84-3)
• EPA Substance Registry System: 2,2-Dimethyl-1-propanol(75-84-3)

Safety Data

• Hazard Codes: F:Flammable
• Statements: R11:
• Safety Statements: S16:; S33:; S7/9:
• Hazardous Substances Data: 75-84-3(Hazardous Substances Data)

Usage

General Description

2,2-Dimethyl-1-propanol, also known as pinacolyl alcohol, is a colorless liquid with a characteristic odor. It is used as a solvent and an intermediate in the production of various chemicals. It is also used as a flotation agent in mineral processing, as a preservative in very low concentrations, and as a reagent for the conversion of carboxylic acids to their corresponding acid chlorides. It is considered to have low acute toxicity, but prolonged exposure to high levels may cause irritation to the eyes, skin, and respiratory tract. It is important to handle this chemical with care and ensure proper ventilation when working with it.

InChI:InChI=1/C5H12O/c1-5(2,3)4-6/h6H,4H2,1-3H3

Synthetic route

titanium isopropoxide (872802-13-6) → 2,2-dimethyl-propanol-1 (75-84-3) + titanium(IV) oxide + tert-butyl alcohol (75-65-0)

Conditions	Yield
In gas byproducts: (CH3)2CCHCH3, CH3CH2C(CH3)CH2; decomposition at a pressure of ca. 0.01 mm of Hg at 550°C; further compound: H2 was obtained with a yield of <0.5%; dineopentane, neopentane and/or 1,1-dimethylcyclopropane were not obtained; org. compounds collected in a liquid-N2 trap; NMR; GC; mass spectra;	A 100% B n/a C <1

pivalaldehyde (630-19-3) → 2,2-dimethyl-propanol-1 (75-84-3)

Conditions	Yield
With isopropyl alcohol; zirconium(IV) oxide for 4h; Rate constant; Heating;	99%
With isopropyl alcohol; zirconium(IV) oxide for 4h; Heating;	99%
With air; H2[Y5(μ4-O)(μ3-O)4(μ-η2-Ph2acac)4(η2-Ph2acac)6] In dichloromethane for 12h;	71%

4,4,5,5-tetramethyl-2-(neopentyloxy)-1,3,2-dioxaborolane → 2,2-dimethyl-propanol-1 (75-84-3)

Conditions	Yield
With silica gel In methanol at 50℃; for 3h;	93%
With methanol; silica gel at 50℃; for 3h;	90%
With methanol; silica gel at 50℃; for 1.91667h;	92 %Spectr.
With water; silica gel In hexane; ethyl acetate

Methyl pivalate (598-98-1) → 2,2-dimethyl-propanol-1 (75-84-3)

Conditions	Yield
With lithium borohydride In methanol; diethyl ether for 0.25h; Heating;	92%
With zinc(II) tetrahydroborate In tetrahydrofuran at 67℃; for 6h;	77%
With sodium tetrahydroborate In methanol; tert-butyl alcohol Heating;	76 % Chromat.

pivaloyl chloride (3282-30-2) → 2,2-dimethyl-propanol-1 (75-84-3)

Conditions	Yield
With zinc(II) tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In diethyl ether at 25℃; for 2h;	88%
With lithium aluminium tetrahydride; diethyl ether
With diethyl ether; tert-butylmagnesium chloride

RETINOL (68-26-8) + pivalaldehyde (630-19-3) → 2,2-dimethyl-propanol-1 (75-84-3) + all-trans-Retinal (116-31-4)

Conditions	Yield
With aluminum isopropoxide In water	A n/a B 87%
With aluminum isopropoxide In water

Methyl pivalate (598-98-1) + allyl-trimethyl-silane (762-72-1) → 2,2-dimethyl-propanol-1 (75-84-3) + 2,2-dimethyl-5-hexen-3-ol (19550-89-1)

Conditions	Yield
With indium (III) iodide; Dimethylphenylsilane In dichloromethane at 20℃; for 1.66667h; Inert atmosphere; chemoselective reaction;	A 29 %Spectr. B 30%

vinylmagnesium chloride (3536-96-7) + isovaleraldehyde (590-86-3) → 4,4-dimethylpent-1-en-3-ol (60041-31-8, 61348-36-5, 24580-44-7) + 2,2-dimethyl-propanol-1 (75-84-3)

Conditions	Yield
	A 16% B 4.5%

tert.-butylhydroperoxide (75-91-2) + bromobis(neopentyloxy)aluminum → 2,2-dimethyl-propanol-1 (75-84-3) + neopentyl pivalate (5340-26-1) + pivalaldehyde (630-19-3) + tert-butyl alcohol (75-65-0) + Trimethylacetic acid (75-98-9) + Al(OH)3

Conditions	Yield
With sulfuric acid; diethylamine Product distribution; Mechanism;	A 1% B n/a C n/a D n/a E n/a F n/a

2,4,4-trimethyl-1-pentene (107-39-1) → 2,2-dimethyl-propanol-1 (75-84-3)

Conditions	Yield
With sulfuric acid; dihydrogen peroxide

formaldehyd (50-00-0) + tert-butylmagnesium bromide (2259-30-5) → 2,2-dimethyl-propanol-1 (75-84-3)

Conditions	Yield
With diethyl ether

formaldehyd (50-00-0) + tert-butylmagnesium chloride (677-22-5) → 2,2-dimethyl-propanol-1 (75-84-3)

3-bromo-2,2-dimethyl-propan-1-ol (40894-00-6) → 2,2-dimethyl-propanol-1 (75-84-3)

Conditions	Yield
With sodium
With methanol; sodium amalgam; water

Methyl formate (107-31-3) + tert-butylmagnesium chloride (677-22-5) → 2,2-dimethyl-propanol-1 (75-84-3) + pivalaldehyde (630-19-3)

Conditions	Yield
With diethyl ether at -15 - -10℃;

2,2-dimethylpropionamide (754-10-9) → 2,2-dimethylpropylamine (5813-64-9) + 2,2-dimethyl-propanol-1 (75-84-3)

Conditions	Yield
With ethanol; sodium
With sec.octyl alcohol; sodium
With dodecacarbonyl-triangulo-triruthenium; hydrogen; molybdenum hexacarbonyl In 1,2-dimethoxyethane at 160℃; under 75007.5 Torr; for 16h; Inert atmosphere;

2,2-dimethylpropionamide (754-10-9) → 2,2-dimethyl-propanol-1 (75-84-3)

Conditions	Yield
With ethanol; sodium
With water; hydrogen at 59.84℃; under 60006 Torr; for 48h;
With C24H20ClN2OPRu; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 10640.7 Torr; for 36h; Inert atmosphere; Schlenk technique;	42 %Chromat.

neopentyloxycarboximidoylmercapto-acetic acid ; hydrobromide → 2,4-thiazolidinedion (2295-31-0) + 2,2-dimethyl-propanol-1 (75-84-3)

Conditions	Yield
at 150℃;

n-butyl magnesium bromide (693-03-8) + diethyl ether (60-29-7) + pivaloyl chloride (3282-30-2) → 2,2-dimethyl-heptan-3-ol (19549-70-3) + 2,2-dimethyl-propanol-1 (75-84-3)

diethyl ether (60-29-7) + isobutylmagnesium bromide (926-62-5) + pivaloyl chloride (3282-30-2) → tertbutylisobutylcarbinol (3970-60-3) + 2,2-dimethyl-propanol-1 (75-84-3)

diethyl ether (60-29-7) + isobutylmagnesium iodide (27720-98-5) + pivaloyl chloride (3282-30-2) → tertbutylisobutylcarbinol (3970-60-3) + 2,2-dimethyl-propanol-1 (75-84-3)

diethyl ether (60-29-7) + 1,1-dimethylpropylmagnesium chloride (28276-08-6) + pivaloyl chloride (3282-30-2) → 2,2-dimethyl-propanol-1 (75-84-3)

2,2-dimethyl-propanol-1 + diphenyldisulfane (882-33-7) → neopentyl phenyl sulphide (7210-80-2)

Conditions	Yield
With tributylphosphine In tetrahydrofuran at 62℃; under 7500600 Torr; for 3h; other pressures and times; var. prim. and sec. alcohols;	100%
With tributylphosphine In tetrahydrofuran at 62℃; under 7500600 Torr; for 3h;	100%

2,2-dimethyl-propanol-1 (75-84-3) + 4-Bromobenzoic acid (586-76-5) → 4-Bromo-benzoic acid 2,2-dimethyl-propyl ester (104110-51-2)

Conditions	Yield
With sulfuric acid In toluene	100%

2,2-dimethyl-propanol-1 (75-84-3) + 4-methoxybenzoic acid (100-09-4) → neopentyl 4-methoxybenzoate (3581-72-4)

Conditions	Yield
With sulfuric acid In toluene	100%

2,2-dimethyl-propanol-1 (75-84-3) + (2S,3S,4R,5R)-2-Acetoxy-3,4,5-tris-benzyloxy-piperidine-1-carboxylic acid benzyl ester → neopentyl 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinopyranoside (161418-75-3)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane at 0℃; for 1.08333h; Substitution;	100%

2,2-dimethyl-propanol-1 (75-84-3) + 4,4'-Dimethoxybenzhydrol (728-87-0) → 4,4'-dianisylmethane (726-18-1) + pivalaldehyde (630-19-3)

Conditions	Yield
With o-benzenedisulfonimide at 80℃; for 8h;	A 100% B n/a

2,2-dimethyl-propanol-1 (75-84-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 2,2-dimethyl-1-trimethylsiloxypropane (18246-63-4)

Conditions	Yield
With Nafion SAC-13 at 20℃; for 0.0666667h;	98%
With aluminum potassium sulfate dodecahydrate In acetonitrile at 20℃; for 0.333333h;	88%
With melamine-N2,N4,N6-trisulfonic acid at 20℃; for 0.25h; neat (no solvent); chemoselective reaction;	87%

2,2-dimethyl-propanol-1 (75-84-3) + 4-bromobenzenesulfonyl chloride (98-58-8) → 4-bromo-benzenesulfonic acid 2,2-dimethylpropyl ester (14248-15-8)

Conditions	Yield
With pyridine In chloroform at -5 - 20℃; for 1h;	98%
With pyridine; dmap In dichloromethane at 20℃; for 21h; Inert atmosphere;	95%
Stage #1: 2,2-dimethyl-propanol-1; 4-bromobenzenesulfonyl chloride In pyridine at 20℃; Stage #2: With sodium hydrogencarbonate In pyridine; water	85%

2,2-dimethyl-propanol-1 (75-84-3) + p-tolylsulfonyl isothiocyanate (1424-52-8) → neopentyl N-toluenesulfonyl thioxocarbamate (175725-45-8)

Conditions	Yield
In benzene for 4h; Heating;	98%

(1-[2-(benzyloxy)-2-oxoethoxy]-8-(methoxycarbonyl)-11-oxo-dibenzo[b,f][1,4]oxazepine-10(11H)-yl)-acetic acid + 2,2-dimethyl-propanol-1 (75-84-3) → 1-(2-benzyloxy-2-oxoethoxy)-10-(2-(2',2'-dimethylpropoxy)-2-oxoethyl)-11-oxo-10,11-dihydro-dibenzo[b,f][1,4]oxazepine-8-carboxylic acid methyl ester

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;	98%

2-bromo-1,3-di-mesityl-2,3-dihydro-1H-1,3,2-diazaphosphole + 2,2-dimethyl-propanol-1 (75-84-3) → 1,3-dimesityl-2-(neopentyloxy)-2,3-dihydro-1H-1,3,2-diazaphosphole

Conditions	Yield
With triethylamine In dichloromethane for 4h; Inert atmosphere; Schlenk technique;	98%

2,2-dimethyl-propanol-1 (75-84-3) + 2,4,4,5,5-pentamethyl-1,3,2-dioxaphospholane → 2-(2,2-Dimethyl-propoxy)-2,4,4,5,5-pentamethyl-2λ5-[1,3,2]dioxaphospholane

Conditions	Yield
In benzene	97%

2,2-dimethyl-propanol-1 (75-84-3) + N-(1-methylpyrazole-4-sulfonyl)-L-(5,5-dimethyl)thiaprolyl-L-4-(N,N-dimethylcarbamyloxy)phenylalanine isopropyl ester (220545-48-2) → N-(1-methylpyrazole-4-sulfonyl)-L-(5,5-dimethyl)thiaprolyl-L-4-(N,N-dimethylcarbamyloxy)phenylalanine 2,2-dimethylpropyl ester

Conditions	Yield
With titanium(IV) isopropylate at 100℃; for 48h;	97%
With titanium(IV) isopropylate

2,2-dimethyl-propanol-1 (75-84-3) + α-bromopropionyl bromide (563-76-8) → 2,2-dimethylpropyl 2-bromopropanoate (5441-01-0)

Conditions	Yield
With pyridine In dichloromethane	97%

2,2-dimethyl-propanol-1 (75-84-3) + C17H16Cl3NOS → C20H26OS (1082828-86-1)

Conditions	Yield
With (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene at 20℃; for 12h; Inert atmosphere;	97%

2,2-dimethyl-propanol-1 (75-84-3) + di-tert-butylisobutylsilyl trifluoromethanesulfonate (1314639-86-5) → di-tert-butylisobutyl(neopentyloxy)silane (1314639-97-8)

Conditions	Yield
With dmap; triethylamine In 1,4-dioxane at 20 - 65℃; for 48h; Inert atmosphere;	96%

2,2-dimethyl-propanol-1 (75-84-3) + 2,4,6-triisopropylbenzoic acid (49623-71-4) → neopentyl 2,4,6-triisopropylbenzoate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere;	96%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;	93%

2,2-dimethyl-propanol-1 (75-84-3) + 4-chloro-aniline (106-47-8) → N-(4-chlorophenyl)-2,2-dimethylpropionamide (65854-91-3)

Conditions	Yield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2,2-Trifluoroacetophenone; cesium acetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tetrahydrofuran at 80℃; for 24h;	96%

2,2-dimethyl-propanol-1 (75-84-3) + 4-methoxybenzonitrile (874-90-8) → 4-(neopentyloxy)benzonitrile (79615-68-2)

Conditions	Yield
With phosphazene base-P4-tert-butyl In tetrahydrofuran; hexane at 50℃; for 18h; Reagent/catalyst; Solvent; Temperature; Molecular sieve; Sealed tube; Inert atmosphere; chemoselective reaction;	96%

2,2-dimethyl-propanol-1 (75-84-3) → neopentyl chlorosulfite (35505-36-3)

Conditions	Yield
With thionyl chloride at 0 - 70℃; for 48h;	95%
With thionyl chloride In dichloromethane for 0.5h; Ambient temperature;	81%
With thionyl chloride; diethyl ether anfangs bei -15grad,zuletzt bei 70grad;
Multi-step reaction with 2 steps 1: diethyl ether; pyridine / -15 °C 2: diethyl ether; thionyl chloride / anfangs bei -15grad,zuletzt bei 70grad View Scheme

2,2-dimethyl-propanol-1 (75-84-3) → pivalaldehyde (630-19-3)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; bisacetoxybromate(I) resin In dichloromethane at 20℃; for 3.5h;	95%
In neat (no solvent) at 20℃; for 0.0666667h; Microwave irradiation;	90%
With quinolinium monofluorochromate(VI) In hexane at 20℃; for 2h;	79%

Upstream product

• 107-39-1 2,4,4-trimethyl-1-pentene 
• 75-98-9 Trimethylacetic acid 
• 558-30-5 2-methyl-1,2-epoxypropane 
• 74-88-4 methyl iodide 
• 106-88-7 ethyloxirane 
• 87585-89-5 3(5)-<1,1-dimethylethyl>-5(3)-<(S)-1-methylpropyl>-pyrazole 
• 99493-25-1 diisopropyl (R,R)-2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate 
• 630-19-3 pivalaldehyde 
• 121335-11-3 2,2-Dimethyl-propionic acid 6-nitro-benzotriazol-1-yl ester 
• 3282-30-2 pivaloyl chloride 
• 60-29-7 diethyl ether 
• 110-54-3 hexane 
• 115-11-7 isobutene 
• 108-88-3 toluene 

Downstream Products

• 6291-08-3 sulfurous acid bis-(2,2-dimethyl-propyl) ester 
• 56377-78-7 (bis(neopentyloxy)methyl)benzene 
• 5441-01-0 2,2-dimethylpropyl 2-bromopropanoate 
• 4513-36-4 2,2-dimethylpropyl acrylate 
• 2397-76-4 methacrylic acid neopentyl ester 
• 15501-33-4 neopentyl iodide 
• 1007-26-7 (2,2-dimethyl-1-propyl)benzene 
• 2049-95-8 tery-amylbenzene 
• 13146-08-2 Toluol-4-sulfinsaeure-neopentylester 
• 96294-84-7 <1-Phenyl-ethyl>-<2,2-dimethyl-propyl>-ether 
• 66085-08-3 Neopentyloxy-triphenyl-phosphonium-chlorid 
• 93032-01-0 O,O-di(2,2-dimethylpropoxy) di(4-methoxyphenyl)thiodiphosphonate 
• 75391-24-1 2,2-dimethylpropyl ethenesulfonate 
• 117264-58-1 neopentyl 2-(3,5-dinitrobenzoyloxy)ethanesulfonate 

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