1,3-Dioxolane-4-ethanol,2,2-dimethyl- supplier

Name
4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE
EINECS
CAS No. 5754-34-7
Article Data64
CAS DataBase
Density 1.29g/cm³
Solubility
Melting Point
Formula C₇H₁₄O₃
Boiling Point 614.9°Cat760mmHg
Molecular Weight 146.186
Flash Point 325.7°C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-(2,2-Dimethyl-1,3-dioxolan-4-yl)ethanol;2,2-Dimethyl-1,3-dioxolan-4-ethanol;4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane;dl-1,2-Isopropylidene-1,2,4-butanetriol;Acetone cyclic(2-hydroxyethyl)ethylene acetal;
PSA 38.69000
LogP 0.52030

Synthetic route

: 3068-00-6
D,L-1,2,4-butanetriol

: 67-64-1
acetone

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; for 4h;	98%
With toluene-4-sulfonic acid at 20℃; for 20h;	97%
With toluene-4-sulfonic acid	86%

: 167629-45-0
4-[2-(4-methoxy-benzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolane

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water	90%

: 3068-00-6
D,L-1,2,4-butanetriol

: 77-76-9
2,2-dimethoxy-propane

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions

Conditions	Yield
With camphor-10-sulfonic acid	85%
With camphor-10-sulfonic acid In acetonitrile at 20℃;	80%
Stage #1: D,L-1,2,4-butanetriol; 2,2-dimethoxy-propane With pyridinium p-toluenesulfonate In acetone at 20℃; for 4h; Reflux; Stage #2: In methanol at 0℃; for 12h;	74%

methylene chloride (CH2 Cl2): methylene chloride (CH2 Cl2)

para-toluene sulfonic acid (p-TsOH): para-toluene sulfonic acid (p-TsOH)

: 3068-00-6
D,L-1,2,4-butanetriol

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions

Conditions	Yield
With magnesium sulfate In methanol; water; acetone	75%

...Expand

: tert-butyl-[2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-dimethyl-silane

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions

Conditions	Yield
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane at 20℃; for 0.25h;	72%

: 3068-00-6
D,L-1,2,4-butanetriol

: 116-11-0
2-Methoxypropene

A: 56476-33-6
(2,2-dimethyl-[1,3]dioxan-4-yl)-methanol

B: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

C: 2-(2,2-dimethyl-1,3-dioxolan-4-ylethoxy)-2-methoxypropane

D: 2-(2,2-dimethyl-1,3-dioxan-4-ylmethoxy)-2-methoxypropane

E: 2,2-bis(2,2-dimethyl-1,3-dioxolan-4-ylethoxy)propane

Conditions

Conditions	Yield
With butyltin(IV) chloride dihydroxide for 90h; Product distribution; Ambient temperature; var. of reagent, ratio, time, further with 2,2-dimethoxypropane;	A 3.0 g B 13.3 g C n/a D n/a E 0.4 g

...Expand

: 83141-42-8
2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions

Conditions	Yield
reduction;

: 3068-00-6
D,L-1,2,4-butanetriol

: 77-76-9
2,2-dimethoxy-propane

: 67-64-1
acetone

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions

Conditions	Yield
With toluene-4-sulfonic acid

...Expand

: 3068-00-6
D,L-1,2,4-butanetriol

: 67-64-1
acetone

A: 56476-33-6
(2,2-dimethyl-[1,3]dioxan-4-yl)-methanol

B: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions

Conditions	Yield
toluene-4-sulfonic acid Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With toluene-4-sulfonic acid Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 3068-00-6
D,L-1,2,4-butanetriol

: 77-76-9
2,2-dimethoxy-propane

A: 56476-33-6
(2,2-dimethyl-[1,3]dioxan-4-yl)-methanol

B: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In acetone at 20℃; for 0.5h;

...Expand

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 124-63-0
methanesulfonyl chloride

: 76099-47-3
2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl methanesulfonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h;	100%
With triethylamine In toluene at 20℃; for 4h; mesylation;	94%
With triethylamine In dichloromethane at 0℃; for 1.5h;	91%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 98-59-9
p-toluenesulfonyl chloride

: 55559-75-6
2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane 1) 0-5 deg C, 3.5 h; 2) rt, 6 h;	99%
With pyridine 1.) 0 deg C, 2 h, 2.) -20 deg C, overnight;	87%
With pyridine at 0 - 20℃; for 24h;	81%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 106-95-6
allyl bromide

: (±)-4-(2-(allyloxy)ethyl)-2,2-dimethyl-1,3-dioxolane

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h;	98%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 83141-42-8
2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde

Conditions

Conditions	Yield
With pyridinium chlorochromate In dichloromethane Ambient temperature;	93%
With aluminum oxide; pyridinium chlorochromate In dichloromethane at 0 - 20℃;	75%
With camphor-10-sulfonic acid; pyridinium chlorochromate In dichloromethane for 3h;	74%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 100-39-0
benzyl bromide

: 94426-71-8
(+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	91%
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide for 3h; Ambient temperature;	71%
With sodium hydride 1.) DMF, RT, 0.5 h, 2.) 30 deg C, 1.5 h; Yield given. Multistep reaction;

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 167629-45-0
4-[2-(4-methoxy-benzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolane

Conditions

Conditions	Yield
With camphor-10-sulfonic acid In dichloromethane	91%
With camphor-10-sulfonic acid In dichloromethane at 20℃; for 12h;	91%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 107-05-1
3-chloroprop-1-ene

: (±)-4-(2-(allyloxy)ethyl)-2,2-dimethyl-1,3-dioxolane

Conditions

Conditions	Yield
With sodium hydroxide In toluene at 30℃; for 6h;	90%
With sodium hydroxide at 30℃; for 2h;

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: oleoyl chloride

: (Z)-Octadec-10-enoic acid 2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester

Conditions

Conditions	Yield
With dmap; TEA for 6h; Ambient temperature;	88%

: 1191-99-7
2,3-dihydro-2H-furan

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 2,2-dimethyl-4-[2-(tetrahydro-furan-2-yloxy)-ethyl]-[1,3]dioxolane

Conditions

Conditions	Yield
With indium(III) chloride; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 3h;	87%
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 12h;	75%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 19715-49-2
4-(dimethylamino)benzenesulfonyl chloride

: rac-O-isopropylidene-3,4-dihydroxybutyl p-dimethylaminobenzenesulfonate

Conditions

Conditions	Yield
With pyridine at 4℃; for 72h; Tosylation;	86%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 124-63-0
methanesulfonyl chloride

: 4-(2-methanesulfonylethyl)-2,2-dimethyl-1,3-dioxolane

Conditions

Conditions	Yield
With triethylamine In dichloromethane at -5℃; for 2.5h; Inert atmosphere;	84.1%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 124-63-0
methanesulfonyl chloride

: 76099-47-3
2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl methanesulfonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at -5℃; for 2.5h; Inert atmosphere;	84.1%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 96754-03-9
2-(phenylsulfonyl)tetrahydro-2H-pyran

: 120346-89-6
2-[2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tetrahydro-pyran

Conditions

Conditions	Yield
With sodium hydrogencarbonate; magnesium bromide In tetrahydrofuran Ambient temperature; overnight (15-24 hrs);	78%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 4330-20-5
N-3-benzoylthymine

: 471256-49-2
(RS)-1-[2-(2,2-dimethyl-[1,3]dioxolan-4-yl)ethyl]thymine

Conditions

Conditions	Yield
With polystyrene-triphenylphosphine; di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu condensation;	67%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 422-56-0
3,3-dichloro-1,1,1,2,2-pentafluoropropane

: 507-55-1
1,3-dichloro-1,1,2,2,3-pentafluoropropane

: 2641-34-1
perfluoro-2,5-dimethyl-3,6-dioxanonanoyl fluoride

: C16H13O6F17

Conditions

Conditions	Yield
With sodium fluoride at 20℃; for 20h;	67%

...Expand

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 59886-90-7
4-chloro-2,3-dimethylpyridine-N-oxide

: 1020733-19-0
4-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy]-2,3-dimethylpyridine 1-oxide

Conditions

Conditions	Yield
Stage #1: 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane With sodium hydride In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 4-chloro-2,3-dimethylpyridine-N-oxide In dimethyl sulfoxide at 60℃; for 2h;	63.8%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 35717-98-7
bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate

: 918795-56-9
[2-(2,2-dimethyl[1,3]dioxolan-4-yl)ethoxymethyl]-phosphonic acid diisopropyl ester

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 16h;	59%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 765962-75-2
3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline

: 1084333-27-6
3-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy]-5-fluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline

Conditions

Conditions	Yield
Stage #1: 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane With sodium hydride In tetrahydrofuran for 0.166667h; Stage #2: 3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline In tetrahydrofuran for 0.5h;	59%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 920-46-7
Methacryloyl chloride

: 2-(2,2-dimethyl-1,3-dioxolane-4-yl)ethyl methacrylate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 15h; Inert atmosphere;	58.4%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 70-34-8
2,4-Dinitrofluorobenzene

: 40742-25-4
(+/-)-1,2-O-isopropylydene-4-(2,4-dinitrophenyloxy)-1,2-butanediol

Conditions

Conditions	Yield
With triethylamine at 25℃; for 6h;	58%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 98095-37-5
4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane

Conditions

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine at 0 - 20℃; Darkness;	49%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.666667h; Sealed tube; Inert atmosphere;	44%
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 2: NaI; K2CO3 View Scheme

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 89942-18-7
isopropylidene ketal of rac-3,4-dihydroxybutyl bromide

Conditions

Conditions	Yield
With bromine; triphenylphosphine In N,N-dimethyl-formamide for 1h; Ambient temperature;	48%
With Bromoform; triethylamine; triphenylphosphine In dichloromethane at 0℃; for 20h;	47.8%
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2.5 h / -5 °C / Inert atmosphere 2: magnesium bromide ethyl etherate / diethyl ether / Inert atmosphere View Scheme

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: piperidinophosphoramidic dichloride

: [2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl] piperidinophosphoramidate

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran	43%

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 29632-74-4
2-fluro-4-iodoaniline

: 96606-37-0
2,4,6-trifluorobenzonitrile

: 1084333-29-8
2-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy]-4-fluoro-6-[(2-fluoro-4-iodophenyl)amino]benzonitrile

Conditions

Conditions	Yield
Stage #1: 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane; 2,4,6-trifluorobenzonitrile With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: 2-fluro-4-iodoaniline With potassium tert-butylate at 20℃; for 3h;	32%

...Expand

1,3-Dioxolane-4-ethanol,2,2-dimethyl- Specification

The 1,3-Dioxolane-4-ethanol,2,2-dimethyl-, with CAS registry number 5754-34-7, has the systematic name of 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol. Besides this, it is also called 4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane. And the chemical formula of this chemical is C₇H₁₄O₃.

Physical properties of 1,3-Dioxolane-4-ethanol,2,2-dimethyl-: (1)ACD/LogP: -0.05; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 18; (6)ACD/KOC (pH 7.4): 18; (7)#H bond acceptors: 3; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 38.69 Å²; (11)Index of Refraction: 1.429; (12)Molar Refractivity: 37.229 cm³; (13)Molar Volume: 144.295 cm³; (14)Polarizability: 14.759×10^-24cm³; (15)Surface Tension: 35.919 dyne/cm; (16)Density: 1.013 g/cm³; (17)Flash Point: 92.192 °C; (18)Enthalpy of Vaporization: 50.886 kJ/mol; (19)Boiling Point: 201.157 °C at 760 mmHg; (20)Vapour Pressure: 0.077 mmHg at 25°C.

Preparation: this chemical can be prepared by propan-2-one and butane-1,2,4-triol. This reaction will need reagents CuSO₄, cc. H₂SO₄. The reaction time is 2 hour(s). The yield is about 68%.

Uses of 1,3-Dioxolane-4-ethanol,2,2-dimethyl-: it can be used to produce (2,2-dimethyl-[1,3]dioxolan-4-yl)-acetaldehyde. This reaction will need reagents PCC, camphorsulfonic acid and solvent CH₂Cl₂. The reaction time is 3 hour(s). The yield is about 74%.

You can still convert the following datas into molecular structure:
(1)SMILES: OCC[C@@H]1OC(OC1)(C)C
(2)InChI: InChI=1/C7H14O3/c1-7(2)9-5-6(10-7)3-4-8/h6,8H,3-5H2,1-2H3/t6-/m0/s1
(3)InChIKey: YYEZYENJAMOWHW-LURJTMIEBC
(4)Std. InChI: InChI=1S/C7H14O3/c1-7(2)9-5-6(10-7)3-4-8/h6,8H,3-5H2,1-2H3/t6-/m0/s1
(5)Std. InChIKey: YYEZYENJAMOWHW-LURJTMIESA-N

Product Name

4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE

Synthetic route

1,3-Dioxolane-4-ethanol,2,2-dimethyl- Specification

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