3143-02-0

Basic information

• Product Name: 3-Methyl-3-oxetanemethanol
• Synonyms: 3-METHYL-3-OXETANEMETHANOL;3-METHYL-3-OXETHANEMETHANOL;3-HYDROXYMETHYL-3-METHYLOXETANE;2-HYDROXYMETHYL-2-METHYL-1,3-EPOXYPROPANE;RARECHEM AK ML 0581;TIMTEC-BB SBB009078;(3-Methyl-3-oxetanyl)methanol;OXetane, 3-hydroxymethyl-3-methyl
• CAS NO: 3143-02-0
• Molecular Formula: C₅H₁₀O₂
• Molecular Weight: 102.13
• EINECS: -0
• Product Categories: Oxetanes;Simple 4-Membered Ring Compounds;Thiophenes
• Mol File: 3143-02-0.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 80 °C40 mm Hg(lit.)
• Flash Point: 210 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.024 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.32mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• Storage Temp.: 2-8°C
• Solubility: Soluble in chloroform, methanol.
• PKA: 14.58±0.10(Predicted)
• BRN: 102773
• CAS DataBase Reference: 3-Methyl-3-oxetanemethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-3-oxetanemethanol(3143-02-0)
• EPA Substance Registry System: 3-Methyl-3-oxetanemethanol(3143-02-0)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 23-24/25-36/37
• WGK Germany: 3
• Hazardous Substances Data: 3143-02-0(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to pale yellow liquid

Uses

3-Methyl-3-oxetanemethanol has been used in the preparation of star-shaped copolymer consisting of a hyperbranched poly(3-methyl-3-oxetanemethanol) core and polytetrahydrofuran arms, pyridyl disulfide-functionalized cyclic carbonate monomer, required for the synthesis of of functional poly(ε-caprolactone) containing pendant pyridyl disulphide groups and δ-lactams. It is used to synthesize octahydroindole alkaloids and γ-butenolides.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 5571, 1983 DOI: 10.1016/S0040-4039(00)94143-1

Purification Methods

Purify the oxetane by fractionation through a glass column [Pattison J Am Chem Soc 79 3455 1957, Corey et al. J Am Chem Soc 106 2736 1984]. [Beilstein 17 III/IV 1128.]

InChI:InChI=1/C5H10O2/c1-5(2-6)3-7-4-5/h6H,2-4H2,1H3

Synthetic route

tert-butyl[(3-methyloxetan-3-yl)methoxy]diphenylsilane (1620017-21-1) → 3-hydroxymethyl-3-methyloxethane (3143-02-0)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h;	84%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h;	84%

2-(hydroxymethyl)-2-methylpropane-1,3-diol (77-85-0) → 3-hydroxymethyl-3-methyloxethane (3143-02-0)

Conditions	Yield
With potassium hydroxide; Diethyl carbonate at 115℃; for 1h;	83.7%
With potassium hydroxide; Diethyl carbonate In ethanol for 2h; Heating;	81%
Stage #1: 2-(hydroxymethyl)-2-methylpropane-1,3-diol With potassium hydroxide; carbonic acid dimethyl ester In methanol under 760.051 Torr; Heating; Stage #2: at 130 - 140℃; under 110 - 120 Torr;	77%

1,1,1-Trimethylolethane dinitrate (84051-79-6) → 3-hydroxymethyl-3-methyloxethane (3143-02-0) + 2-(hydroxymethyl)-2-methylpropane-1,3-diol (77-85-0) + ethyl nitrate (625-58-1) + 1,1,1-Trimethylolethane mononitrate (84051-80-9) + 3-methyl-3-(nitroxymethyl)oxetane (84051-81-0) + NO2- (5.2percent), NO3-

Conditions	Yield
With sodium hydroxide In ethanol; water at 55℃; for 3.10833h; Product distribution; Rate constant; var. NaOH conc.;	A 13% B 0.7% C n/a D 24% E 66% F n/a

trimethylolethane trinitrate (3032-55-1) → 3-hydroxymethyl-3-methyloxethane (3143-02-0) + 2-(hydroxymethyl)-2-methylpropane-1,3-diol (77-85-0) + 1,1,1-Trimethylolethane mononitrate (84051-80-9) + 1,1,1-Trimethylolethane dinitrate (84051-79-6) + 3-methyl-3-(nitroxymethyl)oxetane (84051-81-0)

Conditions	Yield
With sodium hydroxide In methanol; water at 55℃; for 86.1667h; Product distribution; Rate constant; Thermodynamic data; var. NaOH conc., var. solv., solv. effect, ΔH(excit.), ΔF(excit.), ΔS(excit.);	A 45.5% B 2.3% C 31.8% D 1.5% E 16.5%

2-(bromomethyl)-2-methylpropane-1,3-diol (2210-03-9) → 3-hydroxymethyl-3-methyloxethane (3143-02-0)

Conditions	Yield
With Ph4SbOMe In 1,2-dichloro-ethane at 60℃; for 24h; sealed ampule;	82 % Chromat.

2-(hydroxymethyl)-2-methylpropane-1,3-diol (77-85-0) + Diethyl carbonate (105-58-8) + ethanolic KOH-solution → 3-hydroxymethyl-3-methyloxethane (3143-02-0)

Conditions	Yield
Erhitzen des Reaktionsprodukts unter vermindertem Druck bis auf 200grad;

1,1,1-Trimethylolethane mononitrate (84051-80-9) → 3-hydroxymethyl-3-methyloxethane (3143-02-0) + ethyl nitrate (625-58-1) + NO2-, NO3-

Conditions	Yield
With sodium hydroxide In ethanol; water at 55℃; for 21.9033h; Product distribution; Rate constant; var. NaOH conc.;

3-methyl-3-(nitroxymethyl)oxetane (84051-81-0) → 3-hydroxymethyl-3-methyloxethane (3143-02-0) + ethyl nitrate (625-58-1) + NO2-, NO3-

Conditions	Yield
With sodium hydroxide In ethanol; water at 55℃; for 11.38h; Product distribution; Rate constant; var. NaOH conc.;

2-(hydroxymethyl)-2-methylpropane-1,3-diol (77-85-0) + Diethyl carbonate (105-58-8) → 3-hydroxymethyl-3-methyloxethane (3143-02-0)

Conditions	Yield
With potassium hydroxide In ethanol

N-hexyl-3-methyloxetane-3-carboxamide (1256651-65-6) → 3-hydroxymethyl-3-methyloxethane (3143-02-0) + hexan-1-amine (111-26-2)

Conditions	Yield
With [RuH(CO)(BPy-tPNN*)]; hydrogen In tetrahydrofuran at 110℃; under 7600.51 Torr; for 48h; Fischer-Porter tube;	A 74 %Chromat. B 74 %Chromat.

2-(hydroxymethyl)-2-methylpropanedioic acid diethyl ester (72999-08-7) → 3-hydroxymethyl-3-methyloxethane (3143-02-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2.1: lithium borohydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 °C 3.2: 1 h / Cooling with ice 3.3: 4.17 h / 0 - 60 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2.1: lithium borohydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 °C 3.2: Cooling with ice 3.3: 4.17 h / 60 °C / Cooling with ice 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

diethyl 2-[(tert-butyldiphenylsilyloxy)methyl]-2-methylmalonate (1620017-20-0) → 3-hydroxymethyl-3-methyloxethane (3143-02-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium borohydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 1 h / Cooling with ice 2.3: 4.17 h / 0 - 60 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: lithium borohydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: Cooling with ice 2.3: 4.17 h / 60 °C / Cooling with ice 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

2-((tert-butyl-diphenyl-silanyloxy)methyl)-2-methyl-propane-1,3-diol → 3-hydroxymethyl-3-methyloxethane (3143-02-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 °C 1.2: 1 h / Cooling with ice 1.3: 4.17 h / 0 - 60 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 °C 1.2: Cooling with ice 1.3: 4.17 h / 60 °C / Cooling with ice 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

3-hydroxymethyl-3-methyloxethane (3143-02-0) + 4-nitro-benzoyl chloride (122-04-3) → (3-methyloxetan-3-yl)methyl 4-nitrobenzoate (140635-77-4)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 0.333333h;	100%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + p-toluenesulfonyl chloride (98-59-9) → (3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate (99314-44-0)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	100%
With pyridine for 1.5h; Inert atmosphere; Cooling with ice;	96%
With 1-methyl-1H-imidazole; triethylamine In dichloromethane at 25℃; for 2h;	95%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + N-carbobenzyloxy-L-tryptophane (7432-21-5) → N-(benzyloxycarbonyl)-L-tryptophane (3-methyl-3-oxetanyl)methyl ester (127130-93-2)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;	100%
With dmap; dicyclohexyl-carbodiimide In diethyl ether at 25℃; for 0.25h;	84%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + 2-amino-6-chloropyrazine (33332-28-4) → 6-((3-methyloxetan-3-yl)methoxy)pyrazin-2-amine (1431654-81-7)

Conditions	Yield
Stage #1: 3-hydroxymethyl-3-methyloxethane With sodium hydride In 1,4-dioxane; mineral oil at 20℃; for 2h; Stage #2: 2-amino-6-chloropyrazine for 16h; Reflux;	100%
Stage #1: 3-hydroxymethyl-3-methyloxethane With sodium hydride In 1,4-dioxane; mineral oil at 20℃; for 2h; Stage #2: 2-amino-6-chloropyrazine In 1,4-dioxane; mineral oil for 16h; Reflux;	100%

3-hydroxymethyl-3-methyloxethane (3143-02-0) → 3-methyl-3-oxetane carboxylic acid

Conditions	Yield
With dipyridinium dichromate In N,N-dimethyl-formamide at 20℃;	100%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In water; acetonitrile at 20℃;	14 g
In water; acetonitrile at 20℃; Cooling with ice;	14 g

3-hydroxymethyl-3-methyloxethane (3143-02-0) + 3-[4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene-3-yl]propionic acid → 5,5-difluoro-7,9-dimethyl-3-(3-((3-methyloxetan-3-yl)methoxy)-3-oxopropyl)-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;	100%

3-hydroxymethyl-3-methyloxethane (3143-02-0) → 3-bromomethyl-3-methyloxetane (78385-26-9)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane for 0.333333h; Ambient temperature;	99%
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.333333h; Product distribution / selectivity;	95%
With triphenyl phosphite; N-Bromosuccinimide In dichloromethane Ambient temperature;	74%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + butyryl chloride (141-75-3) → butyric acid 3-methyloxetan-3-ylmethyl ester (173729-55-0)

Conditions	Yield
With pyridine In dichloromethane	99%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + 4-Chlorobutanoyl chloride (4635-59-0) → 3-methyl-3-oxetanylmethyl 4-chlorobutanoate (137265-74-8)

Conditions	Yield
With triethylamine In diethyl ether for 1h; Ambient temperature;	98%
With pyridine In dichloromethane at 0℃; for 48h;	92%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + Lithocholic acid (434-13-9) → (R)-(3-methyloxetan-3-yl)methyl 4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;	98%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + 7-bromoheptanoyl chloride (50733-91-0) → 1-methyl-3-oxacyclobutanecarbinyl 7-bromoheptanoate (129884-26-0)

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 1.5h;	97%
With pyridine In tetrahydrofuran at 5℃; for 1.5h;	89%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + acetyl chloride (75-36-5) → (3-Methyloxetan-3-yl)methyl acetate (117471-37-1)

Conditions	Yield
With pyridine In dichloromethane	97%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + 5-bromo-2,3-dimethoxybenzoic acid chloride (107188-91-0) → 3-methyloxetane-3-methyl 2,3-dimethoxy-5-bromobenzoate (259814-04-5)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃;	97%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + hex-5-ynoic acid (53293-00-8) → (3-methyloxyethan-3-yl)methyl-5-hexynoate (89276-33-5)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 1h; Cooling with ice;	97%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 0.75h;

3-hydroxymethyl-3-methyloxethane (3143-02-0) + phenyldimethylsilyl chloride (768-33-2) → 3-methyl-3-[(phenyldimethylsilyl)oxymethyl]oxetane (1269424-51-2)

Conditions	Yield
Stage #1: 3-hydroxymethyl-3-methyloxethane With sodium hydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: phenyldimethylsilyl chloride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;	97%

3-hydroxymethyl-3-methyloxethane (3143-02-0) → 2-(bromomethyl)-2-methylpropane-1,3-diol (2210-03-9)

Conditions	Yield
With hydrogen bromide In tetrahydrofuran; water at 20℃; for 17.5h; Inert atmosphere; Cooling with ice;	96.1%
With hydrogen bromide In tetrahydrofuran at 0 - 20℃; for 5h;	96%
With hydrogen bromide In tetrahydrofuran at 0℃; for 4h;	93.7%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + 5-ketohexanoic acid (3128-06-1) → 3-methyloxetan-3-yl-carbinyl 5-oxohexanoate (264601-56-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 12h;	96%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyldimethyl((3-methyloxetan-3-yl)methoxy)silane

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 6h;	96%
With 1H-imidazole In N,N-dimethyl-formamide at 20 - 25℃; for 12h;	84%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + 2-bromobenzoic acid chloride (7154-66-7) → (3-methyloxetan-3-yl)methyl 2-bromobenzoate

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;	96%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + tert-butyl 2-(4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl)acetate → tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-methyloxetan-3-yl)prop-2-enoate

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.25h;	96%

1,4-dioxane (123-91-1) + 3-hydroxymethyl-3-methyloxethane (3143-02-0) + hydrogen bromide (10035-10-6, 12258-64-9) → 2-(bromomethyl)-2-methylpropane-1,3-diol (2210-03-9)

Conditions	Yield
In water for 3.5h; Inert atmosphere; Schlenk technique; Reflux;	96%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + benzoic acid (65-85-0) → (3-Methyloxetan-3-yl)methyl benzoate (173729-57-2)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;	96%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + 4-(N-((1-(((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)carbonyl)piperidin-4-yl)methyl)sulfamoyl)benzoic acid → 1,1,1,3,3,3-hexafluoropropan-2-yl 4-((4-(((3-methyloxetan-3 yl)methoxy)carbonyl) phenylsulfonamido) methyl)piperidine-1-carboxylate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 0.25h; Inert atmosphere;	96%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + benzyloxyacetic acid (30379-55-6) → (3-methyloxetan-3-yl)methyl 2-(benzyloxy)acetate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; for 18h; Inert atmosphere;	96%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;	94%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + 4-(N-tert-butoxycarbonyl)aminobenzoic acid (66493-39-8) → (3-methyloxetan-3-yl)methyl 4-((tert-butoxycarbonyl)amino)benzoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;	96%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + (Z)-3-iodoprop-2-enoic acid (6214-35-3) → (3-methyl-3-oxetanyl)methyl (Z)-3-iodo-2-propenoate (339177-46-7)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	95%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h;	95%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + 3-[(2,4,6-triisopropylphenyl)sulfenyl]propionic acid (246862-22-6) → (3-methyl-3-oxethanyl)methyl 3-[(2,4,6-triisopropylphenyl)sulfenyl]propionate (246862-23-7)

Conditions	Yield
With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 36h;	95%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + (S)-3-((tert-butyldimethylsilyl)oxy)-4,4-dimethyl-5-oxoheptanoic acid (187283-45-0) → (-)-(3S)-3-(tert-butyldimethylsilyloxy)-4,4-dimethyl-5-oxoheptanoic acid 3-methyloxetan-3-ylmethyl ester (823789-77-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h;	95%

3-hydroxymethyl-3-methyloxethane (3143-02-0) → 3-methyl-3-(nitroxymethyl)oxetane (84051-81-0)

Conditions	Yield
With carbon dioxide; dinitrogen pentoxide at 0℃; under 45004.5 - 60006 Torr; for 0.5h; Autoclave;	95%

3-hydroxymethyl-3-methyloxethane (3143-02-0) + diethyl malonate (105-53-3) → ethyl ((3-methyloxetan-3-yl)methyl)propanedioate

Conditions	Yield
at 150℃; for 48h;	95%
at 150℃; for 48h;	95%

Upstream product

• 77-85-0 2-(hydroxymethyl)-2-methylpropane-1,3-diol 
• 3032-55-1 trimethylolethane trinitrate 
• 2210-03-9 2-(bromomethyl)-2-methylpropane-1,3-diol 
• 105-58-8 Diethyl carbonate 
• 84051-80-9 1,1,1-Trimethylolethane mononitrate 
• 84051-79-6 1,1,1-Trimethylolethane dinitrate 
• 84051-81-0 3-methyl-3-(nitroxymethyl)oxetane 
• 1620017-21-1 tert-butyl[(3-methyloxetan-3-yl)methoxy]diphenylsilane 
• 1620017-20-0 diethyl 2-[(tert-butyldiphenylsilyloxy)methyl]-2-methylmalonate 
• 72999-08-7 2-(hydroxymethyl)-2-methylpropanedioic acid diethyl ester 
• 1256651-65-6 N-hexyl-3-methyloxetane-3-carboxamide 

Downstream Products

• 127130-93-2 N-(benzyloxycarbonyl)-L-tryptophane (3-methyl-3-oxetanyl)methyl ester 
• 173729-57-2 (3-Methyloxetan-3-yl)methyl benzoate 
• 246862-23-7 (3-methyl-3-oxethanyl)methyl 3-[(2,4,6-triisopropylphenyl)sulfenyl]propionate 
• 497870-32-3 3-methyloxetan-3-ylmethyl 4-vinylbenzoic acid 
• 497870-40-3 3-methyloxetan-3-ylmethyl N-phenylbenzimidate 
• 140635-77-4 3-methyl-3-(4-nitrobenzoyloxymethyl)oxetane 
• 622407-53-8 [4-(3-methyl-oxetan-3-ylmethoxycarbonylmethyl)-phenyl]-acetic acid 3-methyl-oxetan-3-ylmethyl ester 
• 886981-71-1 3-(4,5-dichloro-2-nitro-phenoxymethyl)-3-methyl-oxetane 
• 78385-26-9 3-bromomethyl-3-methyloxetane 
• 153209-97-3 (3-methyloxetan-3-yl)methanamine 
• 1160064-80-1 (2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidine-1-carboxylic acid 3-methyl-oxetan-3-ylmethyl ester 
• 779329-94-1 [4-(trifluoromethyl)phenoxy]-acetic acid, (3-methyl-3-oxetanyl)methyl ester 
• 1224874-69-4 (2-anisyl)-(4-anisyl)methyl (3-methyloxetan-3-yl)methyl ether 
• 1224874-60-5 bis(4-anisyl)methyl (3-methyloxetan-3-yl)methyl ether 

Relevant articles and documents

Kinetics and Mechanism for the Alkaline Homogeneous Hydrolysis of 1,1,1-Trimethylolethane Trinitrate

The kinetics for the alkaline homogeneous hydrolysis of 1,1,1-trimethylolethane trinitrate (MTN) in 95percent ethanol-water with sodium hydroxide concentrations between 0.25 and 2.1 M and temperatures between 50.0 and 60.0 degC have been investigated.One mole of MTN was found to react with 3 mol of base and to hydrolize by a series of consecutive and competitive bimolecular and internal cyclization reactions involving three nitrate ester intermediates to form the cyclic alcohol ether 3-methyl-3-oxetanemethanol (AE) as the final major product with only trace amounts of the expected trialcohol 1,1,1-tris(hydroxymethyl)ethane (TA).MTN and its intermediates showed good second-order rate constants for the expression -d(MTN)/dt = k1(MTN) = k2(B-)(MTN), where k1 is the first-order rate constant with excess base, B-.Relative k2 values in 95percent ethanol-water, 95percent methanol-water, and water were found to be 1.0, 0.1, and 0.01, respectively.Hydrolysis kinetics and product formation for each nitrate ester intermediate have been determined, and an overall hydrolysis mechanism for MTN is presented.

A new and versatile synthesis of 3-substituted oxetan-3-yl methyl alcohols

We have developed a novel route for the efficient synthesis of pharmaceutically significant 3-substituted oxetan-3-yl methyl alcohols starting from readily available malonates. The synthesis harnesses the diversity of malonate chemistry and allows access to a range of oxetanes, which exemplifies the versatility of this procedure.

Synthesis and polymerization of alkyl halide-functional cyclic carbonates

To increase the diversity in functional aliphatic polycarbonates, a series of novel chloro- and bromo-functional six-membered cyclic carbonate monomers were synthesized. Despite asymmetry in the monomer functionalities, homopolymerization of the monomers afforded semicrystalline polycarbonates with a high tendency to crystallize from the melt and/or on precipitation from a THF solution. Melting points were found in the 90-105 °C or 120-155 °C range for polymers comprising methyl or ethyl moieties, respectively, in the backbone. The monomers were further copolymerized with trimethylene carbonate to form random copolymers. Even among some of these random copolymers elements of semicrystallinity were found as confirmed by melting endotherms in DSC. The results clearly show that the incorporation of alkyl halide functionalities in aliphatic polycarbonates may lead to materials with a high ability to form crystallites, even in random copolymers, likely driven by polar interactions due to the presence of the halide functionalities.