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503-30-0 Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Trimethylene oxide useful for the synthesis of 3-substituted propanols by reaction with Grignards or organolithiums in the presence of CuBr.

Definition

ChEBI: A saturated organic heteromonocyclic parent that is a four-membered ring comprising of three carbon atoms and an oxygen atom.

General Description

Clear, colorless liquid with an agreeable aromatic odor.

Air & Water Reactions

Highly flammable. Water soluble.

Reactivity Profile

TRIMETHYLENE OXIDE reacts with Grignard reagents and organolithium compounds. TRIMETHYLENE OXIDE is also incompatible with oxidizing agents and strong acids. . An explosion occurred when propylene oxide was added to epoxy resin. Polymerization was catalyzed by amine accelerator in the resin [Bretherick 1995]. Propylene oxide and sodium hydroxide base-catalyzed the polymerization of the former, causing ignition and explosion of a drum of the crude product. [Combust Sci. Technol., 1983].

Fire Hazard

TRIMETHYLENE OXIDE is flammable.

Safety Profile

Moderately toxic by subcutaneous route. May be narcotic in high concentrations. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes

Purification Methods

Distil oxetane twice from sodium metal and then fractionate it through a small column at atmospheric pressure, b 47.0-47.2o. It can also be purified by preparative gas chromatography using a 2m silica gel column. Alternatively, add KOH pellets (50g for 100g of oxetane) and distil it through an efficient column or a column packed with 1/4in Berl Saddles with the main portion boiling at 45-50o being collected and redistilled over fused KOH. [Noller Org Synth Coll Vol III 835 1955, Dittmer et al. J Am Chem Soc 79 4431 1957, Beilstein 17 H 6, 17 I 3, 17 II 12, 17 III/IV 13, 17/1 V 11.]

Check Digit Verification of cas no

The CAS Registry Mumber 503-30-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 3 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 503-30:
(5*5)+(4*0)+(3*3)+(2*3)+(1*0)=40
40 % 10 = 0
So 503-30-0 is a valid CAS Registry Number.
InChI:InChI=1/C3H6O/c1-2-4-3-1/h1-3H2

503-30-0 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A14452)  Trimethylene oxide, 97%   

  • 503-30-0

  • 5g

  • 693.0CNY

  • Detail
  • Alfa Aesar

  • (A14452)  Trimethylene oxide, 97%   

  • 503-30-0

  • 25g

  • 3086.0CNY

  • Detail
  • Alfa Aesar

  • (A14452)  Trimethylene oxide, 97%   

  • 503-30-0

  • 100g

  • 10513.0CNY

  • Detail
  • Aldrich

  • (T76201)  Trimethyleneoxide  97%

  • 503-30-0

  • T76201-5G

  • 1,157.13CNY

  • Detail
  • Aldrich

  • (T76201)  Trimethyleneoxide  97%

  • 503-30-0

  • T76201-10G

  • 1,999.53CNY

  • Detail

503-30-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name oxetane

1.2 Other means of identification

Product number -
Other names 1,3-Epoxypropane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:503-30-0 SDS

503-30-0Synthetic route

(CH3CH2CH2CH2)3SnOCH2CH2CH2Br
40894-08-4

(CH3CH2CH2CH2)3SnOCH2CH2CH2Br

A

trimethylene oxide
503-30-0

trimethylene oxide

B

tributyltin bromide
1461-23-0

tributyltin bromide

Conditions
ConditionsYield
decompn. at 210°C (1 h);A 64%
B n/a
decompn. at 210°C (1 h);A 64%
B n/a
3-Chloropropyl acetate
628-09-1

3-Chloropropyl acetate

trimethylene oxide
503-30-0

trimethylene oxide

Conditions
ConditionsYield
With potassium hydroxide In water Heating;40%
With potassium hydroxide; water at 150℃;
1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

diethyl malonate
105-53-3

diethyl malonate

A

trimethylene oxide
503-30-0

trimethylene oxide

B

diethyl cyclobutane-1,1-dicarboxylate
3779-29-1

diethyl cyclobutane-1,1-dicarboxylate

C

trimethyleneglycol
504-63-2

trimethyleneglycol

Conditions
ConditionsYield
With tetraethylammonium perchlorate In N,N-dimethyl-formamide electrolysis;A n/a
B 35%
C n/a
ethyl acetoacetate
141-97-9

ethyl acetoacetate

1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

A

trimethylene oxide
503-30-0

trimethylene oxide

B

ethyl 1-acetylcyclobutanecarboxylate
126290-87-7

ethyl 1-acetylcyclobutanecarboxylate

C

trimethyleneglycol
504-63-2

trimethyleneglycol

Conditions
ConditionsYield
With tetraethylammonium perchlorate In N,N-dimethyl-formamide electrolysis;A n/a
B 30%
C n/a
1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

A

trimethylene oxide
503-30-0

trimethylene oxide

B

dimethyl cyclobutane-1,1-dicarboxylate
10224-72-3

dimethyl cyclobutane-1,1-dicarboxylate

C

trimethyleneglycol
504-63-2

trimethyleneglycol

Conditions
ConditionsYield
With tetraethylammonium perchlorate In N,N-dimethyl-formamide electrolysis;A n/a
B 25%
C n/a
oct-1-ene
111-66-0

oct-1-ene

trimethylene oxide
503-30-0

trimethylene oxide

Conditions
ConditionsYield
With benzophenone; tri-n-butyl phosphite In benzene Product distribution; Irradiation; different sovents and reaction conditions;5%
(3-chloropropoxy)trimethylsilane
18171-15-8

(3-chloropropoxy)trimethylsilane

trimethylene oxide
503-30-0

trimethylene oxide

Conditions
ConditionsYield
With potassium hydroxide; water
3-bromopropyl acetate
592-33-6

3-bromopropyl acetate

trimethylene oxide
503-30-0

trimethylene oxide

Conditions
ConditionsYield
With potassium hydroxide; water
Phenyl glycidyl ether
122-60-1

Phenyl glycidyl ether

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

trimethylene oxide
503-30-0

trimethylene oxide

Conditions
ConditionsYield
With N-ethylpyridinium iodide
1-chloro-3-hydroxypropane
627-30-5

1-chloro-3-hydroxypropane

trimethylene oxide
503-30-0

trimethylene oxide

Conditions
ConditionsYield
With potassium carbonate
tetrahydrofuran
109-99-9

tetrahydrofuran

A

trimethylene oxide
503-30-0

trimethylene oxide

B

methoxypropanol
1589-49-7

methoxypropanol

Conditions
ConditionsYield
With methane; water; oxygen Irradiation;
4-Chloro-phenol; compound with oxetane

4-Chloro-phenol; compound with oxetane

A

trimethylene oxide
503-30-0

trimethylene oxide

B

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
In cyclohexane at 20℃; Equilibrium constant;
(S)-propyleneoxide
287-25-2

(S)-propyleneoxide

trimethylene oxide
503-30-0

trimethylene oxide

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal at 0℃;
diethoxyltriphenylphosphorane
86852-11-1, 18509-25-6

diethoxyltriphenylphosphorane

trimethyleneglycol
504-63-2

trimethyleneglycol

A

trimethylene oxide
503-30-0

trimethylene oxide

B

3-ethoxy-1-propanol
111-35-3

3-ethoxy-1-propanol

Conditions
ConditionsYield
In dichloromethane at 45℃; Yield given. Yields of byproduct given;
In dichloromethane Heating;A 3 % Spectr.
B 97 % Spectr.
trimethyleneglycol
504-63-2

trimethyleneglycol

A

trimethylene oxide
503-30-0

trimethylene oxide

B

3-ethoxy-1-propanol
111-35-3

3-ethoxy-1-propanol

Conditions
ConditionsYield
With diethoxyltriphenylphosphorane In dichloromethane Heating;A 3 % Spectr.
B 97 % Spectr.
1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

trimethylene oxide
503-30-0

trimethylene oxide

Conditions
ConditionsYield
With Ph4SbOMe In 1,2-dichloro-ethane at 80℃; for 24h; sealed ampule;59 % Chromat.
1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

A

trimethylene oxide
503-30-0

trimethylene oxide

B

trimethyleneglycol
504-63-2

trimethyleneglycol

Conditions
ConditionsYield
With water; triethylamine In ethanol at 124.9℃; Kinetics; further temperatures, further solvent, activation enthalpy and entropy;
n-propyl nitrite
543-67-9

n-propyl nitrite

Methyl formate
107-31-3

Methyl formate

2,2-dimethyl-[1,3,2]dioxasilinane
14879-83-5

2,2-dimethyl-[1,3,2]dioxasilinane

A

trimethylene oxide
503-30-0

trimethylene oxide

B

C5H13O2Si(1-)

C5H13O2Si(1-)

C

C3H9O2Si(1-)
125518-33-4

C3H9O2Si(1-)

Conditions
ConditionsYield
products detemination by I.c.r. method;;
3,5-Dichloro-phenol; compound with oxetane

3,5-Dichloro-phenol; compound with oxetane

A

trimethylene oxide
503-30-0

trimethylene oxide

B

3,5-dichlorophenol
591-35-5

3,5-dichlorophenol

Conditions
ConditionsYield
In cyclohexane at 24.9℃; Equilibrium constant;
3,5-Dichloro-phenol; compound with oxetane

3,5-Dichloro-phenol; compound with oxetane

A

trimethylene oxide
503-30-0

trimethylene oxide

B

3,5-dichlorophenol
591-35-5

3,5-dichlorophenol

Conditions
ConditionsYield
In cyclohexane at 24.9℃; Equilibrium constant;
<γ-chloro-propyl>-acetate

<γ-chloro-propyl>-acetate

trimethylene oxide
503-30-0

trimethylene oxide

Conditions
ConditionsYield
With potassium hydroxide; water at 100 - 120℃;
1,4-dioxane
123-91-1

1,4-dioxane

A

trimethylene oxide
503-30-0

trimethylene oxide

B

formaldehyd
50-00-0

formaldehyd

C

ethene
74-85-1

ethene

D

2-hydroxyethyl vinyl ether
764-48-7

2-hydroxyethyl vinyl ether

E

H2

H2

Conditions
ConditionsYield
Mechanism; Product distribution; Quantum yield; Irradiation; 185 nm vacuum-ultraviolet photolysis;
1-chloro-3-hydroxypropane
627-30-5

1-chloro-3-hydroxypropane

KOH

KOH

trimethylene oxide
503-30-0

trimethylene oxide

3-Chloropropyl acetate
628-09-1

3-Chloropropyl acetate

water
7732-18-5

water

KOH

KOH

trimethylene oxide
503-30-0

trimethylene oxide

Conditions
ConditionsYield
at 100 - 120℃;
3-bromopropyl acetate
592-33-6

3-bromopropyl acetate

water
7732-18-5

water

potassium hydroxide

potassium hydroxide

trimethylene oxide
503-30-0

trimethylene oxide

Conditions
ConditionsYield
at 170℃;
propane
74-98-6

propane

A

trimethylene oxide
503-30-0

trimethylene oxide

B

hydroxy-2-propanone
116-09-6

hydroxy-2-propanone

C

acrolein
107-02-8

acrolein

Conditions
ConditionsYield
With oxygen at 613 - 725℃; under 760.051 Torr;
trimethylene oxide
503-30-0

trimethylene oxide

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

4-<(trimethylsilyl)oxy>butyronitrile
72049-81-1

4-<(trimethylsilyl)oxy>butyronitrile

Conditions
ConditionsYield
With diethylaluminium chloride for 18h; Ambient temperature;100%
trimethylene oxide
503-30-0

trimethylene oxide

carbon dioxide
124-38-9

carbon dioxide

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
With bis(acetylacetonate)oxovanadium; tetrabutylammomium bromide In toluene at 60℃; under 26252.6 Torr; for 8h; Autoclave; Cooling with ice; chemoselective reaction;100%
tetraphenyl stibonium iodide at 100℃; under 36775.4 Torr; for 4h; Product distribution; Var. catalysts, solvents, time and temp.;96%
tetraphenyl stibonium iodide at 100℃; under 36775.4 Torr; for 4h; Var. catalysts, solvents, time and temp.;96%
trimethylene oxide
503-30-0

trimethylene oxide

p-Tolylisocyanate
622-58-2

p-Tolylisocyanate

3-(p-tolyl)-1,3-oxazinan-2-one
61308-51-8

3-(p-tolyl)-1,3-oxazinan-2-one

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; diphenyltin diiodide at 80℃; for 1h; sealed tube;100%
With dibutyl tin diiodide; Triphenylphosphine oxide 1.) room temp; 30 min; 2.) 40 deg C, 3 h; Yield given. Multistep reaction;
With tetraphenyl stibonium iodide In benzene at 40℃; for 4h;80 % Chromat.
trimethylene oxide
503-30-0

trimethylene oxide

1-amino-2-propene
107-11-9

1-amino-2-propene

3-(prop-2-enylamino)propan-1-ol
44768-46-9

3-(prop-2-enylamino)propan-1-ol

Conditions
ConditionsYield
With C49H74AlNO4; tetrabutylammomium bromide In butanone at 75℃; for 18h;100%
trimethylene oxide
503-30-0

trimethylene oxide

N-methylaniline
100-61-8

N-methylaniline

N-Methyl,N-{(3-hydroxy)-1-propyl}aniline
34579-44-7

N-Methyl,N-{(3-hydroxy)-1-propyl}aniline

Conditions
ConditionsYield
With ytterbium(III) triflate In dichloromethane for 4h; Ambient temperature;99%
With lithium tetrafluoroborate In acetonitrile for 68h; Ambient temperature;88%
With ytterbium(III) triflate In dichloromethane for 4h; Product distribution; aminolysis in the presence of various lanthanide(III) salts;
trimethylene oxide
503-30-0

trimethylene oxide

deca-B-methyl-1,12-dicarba-closo-dodecaborane(12)
168098-42-8

deca-B-methyl-1,12-dicarba-closo-dodecaborane(12)

1-(deca-B-methyl-1,12-dicarba-closo-dodecaboran-1-yl)-3-hydroxypropane
220436-33-9

1-(deca-B-methyl-1,12-dicarba-closo-dodecaboran-1-yl)-3-hydroxypropane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran Ar atm.; to a stirred soln. of carborane in THF was added butyllithium in hexane at -5°C, the mixt. was stirred for 0.5 h, allowed to warm to room temp., stirred for 1 h, cooled to -5°C, (CH2)3O was added, stirred at room temp. overnight; satd. aq. NaHCO3 was added, extd. with diethyl ether, dried over MgSO4, filtered, concd. under vac., flashed through a short pad of silica gel with hexane followed by hexane/ethyl acetate (3:1), concd. under vac.;99%
trimethylene oxide
503-30-0

trimethylene oxide

phenylacetylene
536-74-3

phenylacetylene

5-phenylpent-4-yn-1-ol
24595-58-2

5-phenylpent-4-yn-1-ol

Conditions
ConditionsYield
Stage #1: phenylacetylene With n-butyllithium
Stage #2: trimethylene oxide With boron trifluoride diethyl etherate
98%
With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃;84%
With n-butyllithium; boron trifluoride diethyl etherate 1.) 20 min, -78 deg C, THF/n-hexane; 2.) 30 min, -78 deg C, THF; Yield given. Multistep reaction;
Stage #1: phenylacetylene With n-butyllithium Metallation;
Stage #2: trimethylene oxide Alkylation;
trimethylene oxide
503-30-0

trimethylene oxide

carbon oxide sulfide
463-58-1

carbon oxide sulfide

trimethylene monothiocarbonate

trimethylene monothiocarbonate

Conditions
ConditionsYield
With bentonite-supported ionic liquid catalyst at 60℃; under 22502.3 Torr; for 6h; Temperature; Pressure; Autoclave;97.4%
trimethylene oxide
503-30-0

trimethylene oxide

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

2,3-dihydro-2H-furan

3-(4,5-dihydrofuran-2-yl)propan-1-ol
30483-85-3

3-(4,5-dihydrofuran-2-yl)propan-1-ol

Conditions
ConditionsYield
Stage #1: 2,3-dihydro-2H-furan With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - 0℃; for 0.5h; Inert atmosphere;
Stage #2: trimethylene oxide With boron trifluoride diethyl etherate In tetrahydrofuran; pentane at -78℃; for 0.25h;
Stage #3: With triethylamine In tetrahydrofuran; pentane at -78 - 20℃;
97%
Stage #1: 2,3-dihydro-2H-furan With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - 0℃; for 0.5h; Inert atmosphere;
Stage #2: trimethylene oxide With boron trifluoride diethyl etherate In tetrahydrofuran; pentane at -78℃; for 0.25h; Inert atmosphere;
Stage #3: With triethylamine In tetrahydrofuran; pentane at -78 - 20℃; Inert atmosphere;
97%
trimethylene oxide
503-30-0

trimethylene oxide

phenyllithium
591-51-5

phenyllithium

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 0.166667h;96%
With diethyl ether; benzene
trimethylene oxide
503-30-0

trimethylene oxide

isoselenocyanatotrimethylsilane
16966-40-8

isoselenocyanatotrimethylsilane

3-Trimethylsiloxypropyl selenocyanate
128256-12-2

3-Trimethylsiloxypropyl selenocyanate

Conditions
ConditionsYield
potassium selenocyanate In hexane at 40℃; for 24h;96%
trimethylene oxide
503-30-0

trimethylene oxide

trichloromethyl lithium
2146-66-9

trichloromethyl lithium

4,4,4-trichlorobutan-1-ol
64536-07-8

4,4,4-trichlorobutan-1-ol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -95 - -65℃;96%
With boron trifluoride diethyl etherate at -60℃; for 1h;1.7 g
trimethylene oxide
503-30-0

trimethylene oxide

1-(tetrahydropyranyloxy)-4-pentyn
62992-46-5

1-(tetrahydropyranyloxy)-4-pentyn

8-<(2-Oxacyclohexyl)oxy>oct-4-yn-1-ol
73200-26-7

8-<(2-Oxacyclohexyl)oxy>oct-4-yn-1-ol

Conditions
ConditionsYield
With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran at -78 - -50℃;96%
trimethylene oxide
503-30-0

trimethylene oxide

chloroform
67-66-3

chloroform

4,4,4-trichlorobutan-1-ol
64536-07-8

4,4,4-trichlorobutan-1-ol

Conditions
ConditionsYield
With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran at -94℃;96%
trimethylene oxide
503-30-0

trimethylene oxide

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

(3-chloropropyl)dimethylchlorosilane
10605-40-0

(3-chloropropyl)dimethylchlorosilane

Conditions
ConditionsYield
for 2.5h; Heating;95.2%
trimethylene oxide
503-30-0

trimethylene oxide

tert-butylamine
75-64-9

tert-butylamine

3-(tert-butylamino)-1-propanol
18366-44-4

3-(tert-butylamino)-1-propanol

Conditions
ConditionsYield
With lithium tetrafluoroborate In acetonitrile for 42h; Ambient temperature;95%
trimethylene oxide
503-30-0

trimethylene oxide

diethylamine
109-89-7

diethylamine

3-diethylamino-propan-1-ol
622-93-5

3-diethylamino-propan-1-ol

Conditions
ConditionsYield
With lithium perchlorate In acetonitrile at 80℃; for 13h;95%
With lithium tetrafluoroborate In acetonitrile for 42h; Ambient temperature;92%
trimethylene oxide
503-30-0

trimethylene oxide

acryloyl chloride
814-68-6

acryloyl chloride

acrylic acid 3-chloropropyl
5888-79-9

acrylic acid 3-chloropropyl

Conditions
ConditionsYield
pentabutyl propyl guanidinium chloride; silica gel at 45℃; for 2h;95%
With nitroxypropylpyridinol; zinc dibromide In toluene at 45℃; for 9h; Solvent; Reagent/catalyst; Temperature; Reflux;93.7%
trimethylene oxide
503-30-0

trimethylene oxide

xanthene
92-83-1

xanthene

3-(9H-xanthen-9-yl)-propan-1-ol
648928-44-3

3-(9H-xanthen-9-yl)-propan-1-ol

Conditions
ConditionsYield
Stage #1: xanthene With n-butyllithium at 20℃; for 1h;
Stage #2: trimethylene oxide
95%
trimethylene oxide
503-30-0

trimethylene oxide

L-Cysteine
52-90-4

L-Cysteine

Fudosteine

Fudosteine

Conditions
ConditionsYield
Stage #1: L-Cysteine With sodium hydroxide In water at 0 - 10℃; for 1h;
Stage #2: trimethylene oxide In water at 40 - 50℃; for 6h; Reagent/catalyst; Temperature;
94.6%
trimethylene oxide
503-30-0

trimethylene oxide

thiethane 1,1-dioxide
5687-92-3

thiethane 1,1-dioxide

Conditions
ConditionsYield
Stage #1: trimethylene oxide With Pt/Al2O3; hydrogen sulfide at 420℃; for 3.2h; Molecular sieve;
Stage #2: With ozone In acetone at 70℃; under 4500.45 Torr; for 2h; Temperature; Pressure; Autoclave; Molecular sieve; Inert atmosphere;
94.4%
trimethylene oxide
503-30-0

trimethylene oxide

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

3-trimethylsiloxy-1-phenylpropyl isocyanide
98748-92-6

3-trimethylsiloxy-1-phenylpropyl isocyanide

Conditions
ConditionsYield
With zinc(II) iodide In dichloromethane for 12h; Heating;94%
With zinc(II) iodide In dichloromethane Heating; Yield given;
trimethylene oxide
503-30-0

trimethylene oxide

1,7-dicarba-closo-dodecaborane(12)
16986-24-6

1,7-dicarba-closo-dodecaborane(12)

1,7-bis(propan-1-ol)-1,7-closo-carborane
159227-71-1

1,7-bis(propan-1-ol)-1,7-closo-carborane

Conditions
ConditionsYield
Stage #1: 1,7-dicarba-closo-dodecaborane(12) With n-butyllithium In tetrahydrofuran; hexane at -78 - -20℃; for 3.5h; Inert atmosphere;
Stage #2: trimethylene oxide In tetrahydrofuran; hexane at -78 - 20℃; for 15h; Inert atmosphere;
94%
With CH3(CH2)3Li In tetrahydrofuran; hexane (under Ar, Schlenk); soln. of CH3(CH2)3Li in hexane added slowly to THF soln. of B-compound at 0°C, stirred at room temp. for 30 min, oxacyclobutane in THF added dropwise at 0°C, stirred at room temp. for 20 h, HCl added, stirred for 1 h; extd. with Et2O, organic layer concd., residue chromd. on silica gel column with ethyl acetate in hexane;78%
With hydrogenchloride; n-butyllithium In tetrahydrofuran (N2); using Schlenk techniques; stirring of soln. of 1,7-carborane in THF at -78°C; addn. dropwise soln. of n-BuLi in THF over 10 min; stirring for 48 h; slow warming to room temp., addn. of oxetane, reflux for 4 h; quenching by 2 M HCl; extn. of aq. layer with EtOAc, combining of org. layers, washing with H2O, drying over anhyd. MgSO4; removal of solvent in vac., flash chromy. on SiO2 (67% EtOAc in n-hexane); elem. anal.;62%
trimethylene oxide
503-30-0

trimethylene oxide

1,12-dicarbora-closo-dodecaborane
20644-12-6

1,12-dicarbora-closo-dodecaborane

1,12-bis(propan-1-ol)-1,12-closo-carborane
159227-72-2

1,12-bis(propan-1-ol)-1,12-closo-carborane

Conditions
ConditionsYield
Stage #1: 1,12-dicarbora-closo-dodecaborane With n-butyllithium In tetrahydrofuran; hexane at -78 - -20℃; for 3.5h; Inert atmosphere;
Stage #2: trimethylene oxide In tetrahydrofuran; hexane at -78 - 20℃; for 15.5h; Inert atmosphere;
94%
With n-butyllithium In tetrahydrofuran 1.) 2 equiv. n-BuLi, 2.) trimethylene oxide; react. was quenched with 1 M HCl, crystn. from CHCl3;92%
trimethylene oxide
503-30-0

trimethylene oxide

5-phenyl-1-pentyne
1823-14-9

5-phenyl-1-pentyne

8-phenyl-oct-4-yn-1-ol

8-phenyl-oct-4-yn-1-ol

Conditions
ConditionsYield
Stage #1: 5-phenyl-1-pentyne With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: trimethylene oxide With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78 - 20℃; for 4h; Inert atmosphere;
94%
trimethylene oxide
503-30-0

trimethylene oxide

piperidine
110-89-4

piperidine

3-piperidinopropan-1-ol
104-58-5

3-piperidinopropan-1-ol

Conditions
ConditionsYield
With lithium tetrafluoroborate In acetonitrile for 23h; Ambient temperature;93%
With water at 145℃;
trimethylene oxide
503-30-0

trimethylene oxide

benzoyl chloride
98-88-4

benzoyl chloride

3-chloropropyl benzoate
942-95-0

3-chloropropyl benzoate

Conditions
ConditionsYield
With zinc(II) oxide In neat (no solvent) at 0 - 20℃; for 0.5h; Green chemistry;93%
pentabutyl propyl guanidinium chloride; silica gel at 65℃; for 2h;90%
With molybdenum(V) chloride In 1,2-dichloro-ethane at 20℃; for 3h;78%
trimethylene oxide
503-30-0

trimethylene oxide

aniline
62-53-3

aniline

3-hydroxy-N-phenylpropylamine
31121-11-6

3-hydroxy-N-phenylpropylamine

Conditions
ConditionsYield
With lithium tetrafluoroborate In acetonitrile for 64h; Ambient temperature;93%
trimethylene oxide
503-30-0

trimethylene oxide

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

2-(phenylimino)-3-phenyl-1,3-oxazine
24066-67-9

2-(phenylimino)-3-phenyl-1,3-oxazine

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; diphenyltin diiodide at 40℃; for 1h; sealed tube;93%
With tetraphenyl stibonium iodide In benzene at 40℃; for 10h;99 % Chromat.
trimethylene oxide
503-30-0

trimethylene oxide

Methacryloyl chloride
920-46-7

Methacryloyl chloride

3-chloropropyl methacrylate
44903-02-8

3-chloropropyl methacrylate

Conditions
ConditionsYield
With 4-methoxy-phenol; zinc(II) chloride In cyclohexane at 50℃; for 8h; Reflux;92.1%

503-30-0Relevant articles and documents

RADICAL CATIONS OF VARIOUS ETHENE, ETHINE AND CYCLIC ETHERS

Symons, Martyn C. R.,Wren, Brendon W.

, p. 2315 - 2318 (1983)

We have prepared the cations .(1+), .(1+) and .(1+) by the action of ionizing radiation on dilute solutions of neutral precursors in freon at 77 K, and used e.s.r. spectroscopy to study their structures.We have also studied the cations of oxirane, oxetane and methoxyethine for comparative purposes.

-

Allen,Hibbert

, p. 1398,1399 (1934)

-

Method for the preparation of 1-deoxy baccatin III, 1-deoxy taxol and 1-deoxy taxol analogs

-

, (2008/06/13)

1-Deoxybaccatin III, 1-deoxytaxol and 1-deoxy taxol analogs and method for the preparation thereof.

Spiro-cyclic beta-amino acid derivatives as inhibitors of matrix metalloproteases and TNF-alpha converting enzyme (TACE)

-

, (2008/06/13)

The present application describes novel spiro-cyclic β-amino acid derivatives of formula I: or pharmaceutically acceptable salt forms thereof, wherein ring B is a 3-13 membered carbocycle or heterocycle, ring C forms a 3-11 membered spiro-carbocycle or spiro-heterocycleon ring B, and the other variables are defined in the present specification, which are useful as as matrix metalloproteinases (MMP), TNF-α converting enzyme (TACE), and/or aggrecanase inhibitors.

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