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2453-03-4

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2453-03-4 Usage

General Description

1,3-Dioxan-2-one, also referred to as β-Propiolactone, is an organic compound with the formula CH2C(O)CH2C2O. It is a colorless liquid with a slightly sweet odor, highly soluble in water and miscible with alcohol, acetone, and benzene. The substance is known for its use as a sterilizing and sporicidal agent, specifically for blood plasma, vaccines, tissue grafts, surgical instruments, enzymes, and more. However, β-Propiolactone has been classified as a carcinogen because it has the potential to cause irritation to the eyes, skin, and respiratory tract, as well as cause harm to human genetic material. It is commonly handled and stored in tightly closed containers in a cool, dry, well-ventilated area due to its highly reactive nature and flammability.

Check Digit Verification of cas no

The CAS Registry Mumber 2453-03-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,4,5 and 3 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 2453-03:
(6*2)+(5*4)+(4*5)+(3*3)+(2*0)+(1*3)=64
64 % 10 = 4
So 2453-03-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O3/c5-4-6-2-1-3-7-4/h1-3H2

2453-03-4 Well-known Company Product Price

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  • TCI America

  • (D3821)  1,3-Dioxan-2-one  >98.0%(GC)

  • 2453-03-4

  • 5g

  • 1,450.00CNY

  • Detail
  • TCI America

  • (D3821)  1,3-Dioxan-2-one  >98.0%(GC)

  • 2453-03-4

  • 25g

  • 4,900.00CNY

  • Detail

2453-03-4SDS

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 1,3-Dioxan-2-one

1.2 Other means of identification

Product number -
Other names 2-oxo-1,3-dioxane

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:2453-03-4 SDS

2453-03-4Synthetic route

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%
4-(trifluoromethoxy)benzonitrile
332-25-2

4-(trifluoromethoxy)benzonitrile

trimethyleneglycol
504-63-2

trimethyleneglycol

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
With 3,7-di([1,1′-biphenyl]-4-yl)-10-(naphthalen-1-yl)-10H-phenoxazine; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Reagent/catalyst; Inert atmosphere; Irradiation; Sealed tube;99%
carbon dioxide
124-38-9

carbon dioxide

1-chloro-3-hydroxypropane
627-30-5

1-chloro-3-hydroxypropane

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 40℃; under 760.051 Torr; for 15h; Reagent/catalyst; Temperature; Inert atmosphere; Glovebox; Green chemistry;95%
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; caesium carbonate In N,N-dimethyl-formamide at 40℃; under 760.051 Torr; for 15h; Concentration; Temperature; Glovebox; Inert atmosphere;95 %Spectr.
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 20℃;
tetrahydrofuran
109-99-9

tetrahydrofuran

carbon dioxide
124-38-9

carbon dioxide

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
With tetrabutylammomium bromide; C14H8O5(2-)*Co(2+)*0.5C24H30N4 at 20℃; under 11251.1 Torr; for 30h; High pressure;90%
urea
57-13-6

urea

trimethyleneglycol
504-63-2

trimethyleneglycol

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
With ZnLa2O4 In neat liquid at 150℃; under 15.0015 Torr; Catalytic behavior; Reagent/catalyst; Time;80.5%
With 1-hexadecyl-3-methylimidazolium chloride; zinc(II) chloride In neat (no solvent) at 160℃; under 112.511 Torr; for 3h; Green chemistry;72.3%
With zinc(II) chloride In 1,1,2,2-tetrachloroethane at 146℃; for 24h; Temperature; Solvent; Inert atmosphere;12 %Chromat.
Dibutyl carbonate
542-52-9

Dibutyl carbonate

trimethyleneglycol
504-63-2

trimethyleneglycol

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
With sodium butanolate Reagent/catalyst;80%
carbon dioxide
124-38-9

carbon dioxide

trimethyleneglycol
504-63-2

trimethyleneglycol

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
With 2-Cyanopyridine; cerium(IV) oxide at 129.84℃; under 37503.8 Torr; for 12h; Autoclave;79%
With 2-Cyanopyridine; cerium(IV) oxide at 140℃; under 60006 Torr; for 1h; Autoclave;
With 2-Cyanopyridine; cerium(IV) oxide at 140℃; under 60006 Torr; for 1h; Autoclave;
carbon monoxide
201230-82-2

carbon monoxide

trimethyleneglycol
504-63-2

trimethyleneglycol

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
With air; potassium iodide; palladium(II) iodide In ISOPROPYLAMIDE at 100℃; under 15201 Torr; for 15h; Autoclave;74%
With oxygen; potassium iodide; palladium(II) iodide In N,N-dimethyl acetamide at 100℃; under 15201 Torr; for 15h;74%
With (neocuproine)Pd(OAc)2; sode de l'acide trichloroisocyanurique In acetonitrile at 35℃; under 1794.37 Torr; for 18h;38%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

trimethyleneglycol
504-63-2

trimethyleneglycol

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran70%
Stage #1: chloroformic acid ethyl ester; trimethyleneglycol In tetrahydrofuran for 1h; Cooling with ice;
Stage #2: With triethylamine In tetrahydrofuran at 20℃; for 2h;
43%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h;21%
Dipropyl carbonate
623-96-1

Dipropyl carbonate

trimethyleneglycol
504-63-2

trimethyleneglycol

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
With sodium n-propoxide Reagent/catalyst;68%
potassium carbonate
584-08-7

potassium carbonate

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

1,3-dibromo-propane

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
tributyltin chloride In N,N-dimethyl-formamide at 60℃; for 8h;66%
Diethyl carbonate
105-58-8

Diethyl carbonate

trimethyleneglycol
504-63-2

trimethyleneglycol

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
With sodium ethanolate Reagent/catalyst;62%
With sodium methylate at 100 - 170℃;30%
With sodium at 170℃; Entfernen des entstehenden Aethanols;
With sodium methylate at 160℃; Entfernen des entstehenden Aethanols;
With stannous octoate at 160℃; for 8h;
2-ethoxy-1,3-dioxane
76508-46-8

2-ethoxy-1,3-dioxane

Bromoform
75-25-2

Bromoform

A

trimethylene carbonate
2453-03-4

trimethylene carbonate

B

ethyl bromide
74-96-4

ethyl bromide

C

3-Brompropylformiat
53452-10-1

3-Brompropylformiat

D

acetaldehyde
75-07-0

acetaldehyde

E

3-bromopropyl ethyl carbonate

3-bromopropyl ethyl carbonate

F

1,1-dibromomethane
74-95-3

1,1-dibromomethane

Conditions
ConditionsYield
dibenzoyl peroxide at 100℃; for 2h; Rate constant; Product distribution; other temperature;A n/a
B n/a
C n/a
D n/a
E 60%
F n/a
Bromoform
75-25-2

Bromoform

2-(hexyloxy)-m-dioxane

2-(hexyloxy)-m-dioxane

A

trimethylene carbonate
2453-03-4

trimethylene carbonate

B

1-bromo-hexane
111-25-1

1-bromo-hexane

C

3-Brompropylformiat
53452-10-1

3-Brompropylformiat

D

hexanal
66-25-1

hexanal

E

3-bromopropyl hexyl carbonate

3-bromopropyl hexyl carbonate

F

1,1-dibromomethane
74-95-3

1,1-dibromomethane

Conditions
ConditionsYield
dibenzoyl peroxide at 100℃; for 2h; Rate constant; Product distribution; other temperature;A n/a
B n/a
C n/a
D n/a
E 56%
F n/a
1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

trimethyleneglycol
504-63-2

trimethyleneglycol

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
Stage #1: 1,1'-carbonyldiimidazole; trimethyleneglycol at 20℃;
Stage #2: With acetic acid Reflux;
53%
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

trimethyleneglycol
504-63-2

trimethyleneglycol

A

trimethylene carbonate
2453-03-4

trimethylene carbonate

B

propane-1,3-diyl dimethyl dicarbonate
179902-20-6

propane-1,3-diyl dimethyl dicarbonate

C

3-(methoxycarbonyloxy)propan-1-ol

3-(methoxycarbonyloxy)propan-1-ol

Conditions
ConditionsYield
at 120℃; for 1h; Molecular sieve;A 7.6%
B 46%
C 46.3%
With Novozym435 at 60℃; for 7h; Kinetics; Time; Molecular sieve; Enzymatic reaction;
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

trimethyleneglycol
504-63-2

trimethyleneglycol

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
Stage #1: carbonic acid dimethyl ester; trimethyleneglycol With Novozym435 at 60℃; for 7h; Molecular sieve; Enzymatic reaction;
Stage #2: at 90℃; for 40h; chemoselective reaction;
43.2%
With sodium at 79.84 - 169.84℃;
bis-2-propyl carbonate
6482-34-4

bis-2-propyl carbonate

trimethyleneglycol
504-63-2

trimethyleneglycol

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
With sodium isopropylate Reagent/catalyst;25%
trimethylene oxide
503-30-0

trimethylene oxide

carbon dioxide
124-38-9

carbon dioxide

A

trimethylene carbonate
2453-03-4

trimethylene carbonate

B

polymer, 21.5% ether linkages; monomer(s): oxetane; carbon dioxide

polymer, 21.5% ether linkages; monomer(s): oxetane; carbon dioxide

Conditions
ConditionsYield
tricyclohexylphosphine In toluene at 110℃; under 26252.6 Torr; for 24h;A 21.1%
B 79 % Spectr.
trimethylene oxide
503-30-0

trimethylene oxide

carbon dioxide
124-38-9

carbon dioxide

A

trimethylene carbonate
2453-03-4

trimethylene carbonate

B

polymer, 7.2% ether linkages; monomer(s): oxetane; carbon dioxide

polymer, 7.2% ether linkages; monomer(s): oxetane; carbon dioxide

Conditions
ConditionsYield
tetrabutylammomium bromide In toluene at 110℃; under 26252.6 Torr; for 24h;A 11.7%
B 88.2 % Spectr.
trimethylene oxide
503-30-0

trimethylene oxide

carbon dioxide
124-38-9

carbon dioxide

A

trimethylene carbonate
2453-03-4

trimethylene carbonate

B

polymer, 3.6% ether linkages; monomer(s): oxetane; carbon dioxide

polymer, 3.6% ether linkages; monomer(s): oxetane; carbon dioxide

Conditions
ConditionsYield
(Ph3P)2NCl In toluene at 110℃; under 26252.6 Torr; for 24h;A 5.9%
B 94 % Spectr.
trimethylene oxide
503-30-0

trimethylene oxide

carbon dioxide
124-38-9

carbon dioxide

A

trimethylene carbonate
2453-03-4

trimethylene carbonate

B

polymer, 1.4% ether linkages; monomer(s): oxetane; carbon dioxide

polymer, 1.4% ether linkages; monomer(s): oxetane; carbon dioxide

Conditions
ConditionsYield
(salen)Cr(III)Cl; (Ph3P)2NN3 In toluene at 110℃; under 26252.6 Torr; for 24h;A 2.3%
B 97.6 % Spectr.
2,2-diphenoxy-1,3-dioxane
105014-07-1

2,2-diphenoxy-1,3-dioxane

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
With hydrogenchloride In [D3]acetonitrile; water-d2
1,3-Bis(1,3-dioxan-2-yloxy)propane
81381-75-1

1,3-Bis(1,3-dioxan-2-yloxy)propane

A

trimethylene carbonate
2453-03-4

trimethylene carbonate

B

propyl methanoate
110-74-7

propyl methanoate

C

2-propoxy-1,3-dioxane
85533-20-6

2-propoxy-1,3-dioxane

D

3-([1,3]Dioxan-2-yloxy)-propionaldehyde
85533-24-0

3-([1,3]Dioxan-2-yloxy)-propionaldehyde

E

propyl 3-(1,3-dioxan-2-yloxy)propyl carbonate
85533-23-9

propyl 3-(1,3-dioxan-2-yloxy)propyl carbonate

Conditions
ConditionsYield
With di-tert-butyl peroxide at 130℃; for 0.5h; Product distribution;A 0.02 mol
B 0.01 mol
C 0.02 mol
D 0.01 mol
E 0.06 mol
2,2-Dimethoxy-1,3-dioxan
95104-50-0

2,2-Dimethoxy-1,3-dioxan

A

trimethylene carbonate
2453-03-4

trimethylene carbonate

B

3-(methoxycarbonyloxy)propan-1-ol

3-(methoxycarbonyloxy)propan-1-ol

Conditions
ConditionsYield
With hydrogenchloride In [D3]acetonitrile; water-d2
2-propoxy-1,3-dioxane
85533-20-6

2-propoxy-1,3-dioxane

A

trimethylene carbonate
2453-03-4

trimethylene carbonate

B

propane
74-98-6

propane

C

propyl methanoate
110-74-7

propyl methanoate

D

Dipropyl carbonate
623-96-1

Dipropyl carbonate

E

propionaldehyde
123-38-6

propionaldehyde

Conditions
ConditionsYield
With di-tert-butyl peroxide In chlorobenzene at 130℃; Product distribution; Rate constant; Mechanism;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

trimethyleneglycol
504-63-2

trimethyleneglycol

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; cyclocondensation;88 % Spectr.
phosgene
75-44-5

phosgene

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

trimethyleneglycol
504-63-2

trimethyleneglycol

trimethylene carbonate
2453-03-4

trimethylene carbonate

phosgene
75-44-5

phosgene

trimethyleneglycol
504-63-2

trimethyleneglycol

trimethylene carbonate
2453-03-4

trimethylene carbonate

Conditions
ConditionsYield
In 1,2-dichloro-ethane
trimethylene carbonate
2453-03-4

trimethylene carbonate

polymer, ring-opening polymerisation, Mw/Mn: 1.75; monomer(s): trimethylene carbonate

polymer, ring-opening polymerisation, Mw/Mn: 1.75; monomer(s): trimethylene carbonate

Conditions
ConditionsYield
With [Sm{Ph2NC(NCy)2}3]*2C7H8 In toluene at 60℃; for 0.5h;100%
trimethylene carbonate
2453-03-4

trimethylene carbonate

hydrazinecarboxylic acid 3-hyroxypropyl ester
4341-19-9

hydrazinecarboxylic acid 3-hyroxypropyl ester

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 18h; Heating;99%
trimethylene carbonate
2453-03-4

trimethylene carbonate

trimethyleneglycol
504-63-2

trimethyleneglycol

Conditions
ConditionsYield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen In tetrahydrofuran at 140℃; under 38002.6 Torr; for 2h; Pressure; Autoclave;99%
With zinc bis(2,4-pentanedionate) monohydrate In benzene at 70℃; for 3h; Inert atmosphere;
trimethylene carbonate
2453-03-4

trimethylene carbonate

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

4,4,5,5,4',4',5',5'-octamethyl-2,2'-propane-1,3-diyldioxy-bis-[1,3,2]dioxaborolane
97594-98-4

4,4,5,5,4',4',5',5'-octamethyl-2,2'-propane-1,3-diyldioxy-bis-[1,3,2]dioxaborolane

Conditions
ConditionsYield
With manganese(II) triflate bis-acetonitrile solvate; potassium tert-butylate In benzene-d6 at 20℃; for 3h; Inert atmosphere; Glovebox;99%
With C42H50Mg2N4 for 6h;98 %Spectr.
With dibutylmagnesium In n-heptane; (2)H8-toluene at 85℃; for 6h;> 95 %Spectr.
With tris(bis(trimethylsilyl)amido)lanthanum(III) In neat (no solvent) at 25℃; for 0.333333h; chemoselective reaction;99 %Spectr.
In tetrahydrofuran at 25℃; for 2h; Inert atmosphere;
trimethylene carbonate
2453-03-4

trimethylene carbonate

Butane-1,4-diol
110-63-4

Butane-1,4-diol

poly(trimethylene carbonate), PDI = 1.58; monomer(s): trimethylene carbonate; 1,4-butanediol

poly(trimethylene carbonate), PDI = 1.58; monomer(s): trimethylene carbonate; 1,4-butanediol

Conditions
ConditionsYield
With tin(II) octanoate for 4h; Heating;95%
trimethylene carbonate
2453-03-4

trimethylene carbonate

N-butylamine
109-73-9

N-butylamine

C8H17NO3

C8H17NO3

Conditions
ConditionsYield
at 60℃; for 12h;95%
trimethylene carbonate
2453-03-4

trimethylene carbonate

polymer, ring-opening polymerisation, Mw/Mn: 1.56; monomer(s): trimethylene carbonate

polymer, ring-opening polymerisation, Mw/Mn: 1.56; monomer(s): trimethylene carbonate

Conditions
ConditionsYield
With [Yb{Ph2NC(NCy)2}3]*2C7H8 In toluene at 60℃; for 0.5h;94.4%
trimethylene carbonate
2453-03-4

trimethylene carbonate

methylated poly(ethylene glycol)

methylated poly(ethylene glycol)

D,L-lactide
95-96-5

D,L-lactide

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 28.8:71.2, Mw/Mn = 1.13

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 28.8:71.2, Mw/Mn = 1.13

Conditions
ConditionsYield
With stannous octoate at 160℃; for 24h;94.1%
trimethylene carbonate
2453-03-4

trimethylene carbonate

methylated poly(ethylene glycol)

methylated poly(ethylene glycol)

D,L-lactide
95-96-5

D,L-lactide

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 13.2:86.8, Mw/Mn = 1.12

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 13.2:86.8, Mw/Mn = 1.12

Conditions
ConditionsYield
With stannous octoate at 160℃; for 24h;93.8%
hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

trimethylene carbonate
2453-03-4

trimethylene carbonate

Tetraethylene glycol
112-60-7

Tetraethylene glycol

L,L-dilactide
4511-42-6

L,L-dilactide

polymer, A-B-A triblock copolymer, Mn 22000 Da, Mw 27000 Da by SEC, Mn 18000 Da by NMR, inherent viscosity at 20 deg C in CH2Cl2 (2g/l) 0.260 dl/g; monomer(s): ε-caprolactone; trimethylene carbonate; tetra(ethylene glycol); L-lactide

polymer, A-B-A triblock copolymer, Mn 22000 Da, Mw 27000 Da by SEC, Mn 18000 Da by NMR, inherent viscosity at 20 deg C in CH2Cl2 (2g/l) 0.260 dl/g; monomer(s): ε-caprolactone; trimethylene carbonate; tetra(ethylene glycol); L-lactide

Conditions
ConditionsYield
Stage #1: hexahydro-2H-oxepin-2-one; trimethylene carbonate; Tetraethylene glycol With bismuth(III) n-hexanoate In chlorobenzene at 120℃; for 24h;
Stage #2: L,L-dilactide In chlorobenzene at 120℃; for 24h; Further stages.;
92%
hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

trimethylene carbonate
2453-03-4

trimethylene carbonate

Tetraethylene glycol
112-60-7

Tetraethylene glycol

L,L-dilactide
4511-42-6

L,L-dilactide

polymer, A-B-A triblock copolymer, Mn 13000 Da, Mw 15000 Da by SEC, Mn 9800 Da by NMR, inherent viscosity at 20 deg C in CH2Cl2 (2g/l) 0.180 dl/g; monomer(s): ε-caprolactone; trimethylene carbonate; tetra(ethylene glycol); L-lactide

polymer, A-B-A triblock copolymer, Mn 13000 Da, Mw 15000 Da by SEC, Mn 9800 Da by NMR, inherent viscosity at 20 deg C in CH2Cl2 (2g/l) 0.180 dl/g; monomer(s): ε-caprolactone; trimethylene carbonate; tetra(ethylene glycol); L-lactide

Conditions
ConditionsYield
Stage #1: hexahydro-2H-oxepin-2-one; trimethylene carbonate; Tetraethylene glycol With bismuth(III) n-hexanoate In chlorobenzene at 120℃; for 24h;
Stage #2: L,L-dilactide In chlorobenzene at 120℃; for 24h; Further stages.;
91%
trimethylene carbonate
2453-03-4

trimethylene carbonate

methylated poly(ethylene glycol)

methylated poly(ethylene glycol)

D,L-lactide
95-96-5

D,L-lactide

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 29.1:70.9, Mw/Mn = 1.03

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 29.1:70.9, Mw/Mn = 1.03

Conditions
ConditionsYield
With stannous octoate at 160℃; for 24h;89.7%
trimethylene carbonate
2453-03-4

trimethylene carbonate

methylated poly(ethylene glycol)

methylated poly(ethylene glycol)

D,L-lactide
95-96-5

D,L-lactide

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 33.2:66.8, Mw/Mn = 1.15

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 33.2:66.8, Mw/Mn = 1.15

Conditions
ConditionsYield
With stannous octoate at 160℃; for 24h;89.7%
trimethylene carbonate
2453-03-4

trimethylene carbonate

methylated poly(ethylene glycol)

methylated poly(ethylene glycol)

D,L-lactide
95-96-5

D,L-lactide

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 33.3:66.7, Mw/Mn = 1.20

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 33.3:66.7, Mw/Mn = 1.20

Conditions
ConditionsYield
With stannous octoate at 160℃; for 24h;89.7%
hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

trimethylene carbonate
2453-03-4

trimethylene carbonate

Tetraethylene glycol
112-60-7

Tetraethylene glycol

L,L-dilactide
4511-42-6

L,L-dilactide

polymer, A-B-A triblock copolymer, Mn 21000 Da, Mw 26000 Da by SEC, Mn 15800 Da by NMR, inherent viscosity at 20 deg C in CH2Cl2 (2g/l) 0.255 dl/g; monomer(s): ε-caprolactone; trimethylene carbonate; tetra(ethylene glycol); L-lactide

polymer, A-B-A triblock copolymer, Mn 21000 Da, Mw 26000 Da by SEC, Mn 15800 Da by NMR, inherent viscosity at 20 deg C in CH2Cl2 (2g/l) 0.255 dl/g; monomer(s): ε-caprolactone; trimethylene carbonate; tetra(ethylene glycol); L-lactide

Conditions
ConditionsYield
Stage #1: hexahydro-2H-oxepin-2-one; trimethylene carbonate; Tetraethylene glycol With bismuth(III) n-hexanoate In chlorobenzene at 120℃; for 24h;
Stage #2: L,L-dilactide In chlorobenzene at 120℃; for 24h; Further stages.;
89%
trimethylene carbonate
2453-03-4

trimethylene carbonate

phenol
108-95-2

phenol

3-phenoxypropanol
6180-61-6

3-phenoxypropanol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 180℃; for 6h; Inert atmosphere; Schlenk technique;88%
trimethylene carbonate
2453-03-4

trimethylene carbonate

methylated poly(ethylene glycol)

methylated poly(ethylene glycol)

D,L-lactide
95-96-5

D,L-lactide

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 82.1:17.9, Mw/Mn = 1.16

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 82.1:17.9, Mw/Mn = 1.16

Conditions
ConditionsYield
With stannous octoate at 160℃; for 24h;87.8%
trimethylene carbonate
2453-03-4

trimethylene carbonate

methylated poly(ethylene glycol)

methylated poly(ethylene glycol)

D,L-lactide
95-96-5

D,L-lactide

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 58.6:41.4, Mw/Mn = 1.19

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 58.6:41.4, Mw/Mn = 1.19

Conditions
ConditionsYield
With stannous octoate at 160℃; for 24h;86.5%
trimethylene carbonate
2453-03-4

trimethylene carbonate

polymer, ring-opening polymerisation, Mw/Mn: 1.66; monomer(s): trimethylene carbonate

polymer, ring-opening polymerisation, Mw/Mn: 1.66; monomer(s): trimethylene carbonate

Conditions
ConditionsYield
With [Nd{Ph2NC(NCy)2}3]*2C7H8 In toluene at 40℃; for 0.5h;85.65%
trimethylene carbonate
2453-03-4

trimethylene carbonate

methylated poly(ethylene glycol)

methylated poly(ethylene glycol)

D,L-lactide
95-96-5

D,L-lactide

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 35.1:64.9, Mw/Mn = 1.05

poly(D,L-lactide-co-trimethylene carbonate)-methylated poly(ethylene glycol) (MW: 2000 g/ml), molar ratio of D,L-lactide:trimethyl carbonate 35.1:64.9, Mw/Mn = 1.05

Conditions
ConditionsYield
With stannous octoate at 160℃; for 24h;85.5%
hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

trimethylene carbonate
2453-03-4

trimethylene carbonate

Tetraethylene glycol
112-60-7

Tetraethylene glycol

L,L-dilactide
4511-42-6

L,L-dilactide

polymer, A-B-A triblock copolymer, Mn 13000 Da, Mw 16000 Da by SEC, Mn 11000 Da by NMR, inherent viscosity at 20 deg C in CH2Cl2 (2g/l) 0.205 dl/g; monomer(s): ε-caprolactone; trimethylene carbonate; tetra(ethylene glycol); L-lactide

polymer, A-B-A triblock copolymer, Mn 13000 Da, Mw 16000 Da by SEC, Mn 11000 Da by NMR, inherent viscosity at 20 deg C in CH2Cl2 (2g/l) 0.205 dl/g; monomer(s): ε-caprolactone; trimethylene carbonate; tetra(ethylene glycol); L-lactide

Conditions
ConditionsYield
Stage #1: hexahydro-2H-oxepin-2-one; trimethylene carbonate; Tetraethylene glycol With bismuth(III) n-hexanoate In chlorobenzene at 120℃; for 24h;
Stage #2: L,L-dilactide In chlorobenzene at 120℃; for 24h; Further stages.;
82%
hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

trimethylene carbonate
2453-03-4

trimethylene carbonate

poly(ε-caprolactone-ran-trimethylene carbonate), Mn 3.98E4 by GPC, PDI 1.98; monomer(s): ε-caprolactone; trimethylene carbonate

poly(ε-caprolactone-ran-trimethylene carbonate), Mn 3.98E4 by GPC, PDI 1.98; monomer(s): ε-caprolactone; trimethylene carbonate

Conditions
ConditionsYield
With scandium tris(2,6-di-tert-butyl-4-methylphenolate) In toluene at 100℃; for 8h;80.1%
hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

trimethylene carbonate
2453-03-4

trimethylene carbonate

poly(ε-caprolactone-ran-trimethylene carbonate), Mn 2.72E4 by GPC, PDI 2.06, 59.2 percent diads of caprolactone-caprolactone, 23.8 percent diads of trimethylene carbonate-trimethylene carbonate; monomer(s): ε-caprolactone; trimethylene carbonate

poly(ε-caprolactone-ran-trimethylene carbonate), Mn 2.72E4 by GPC, PDI 2.06, 59.2 percent diads of caprolactone-caprolactone, 23.8 percent diads of trimethylene carbonate-trimethylene carbonate; monomer(s): ε-caprolactone; trimethylene carbonate

Conditions
ConditionsYield
With scandium tris(2,6-di-tert-butyl-4-methylphenolate) In toluene at 0℃; for 12h;80%
trimethylene carbonate
2453-03-4

trimethylene carbonate

A

methanol
67-56-1

methanol

B

trimethyleneglycol
504-63-2

trimethyleneglycol

Conditions
ConditionsYield
With (bis[(2-diisopropylphosphino)ethyl]amine)Mn(CO)2Br; hydrogen; sodium t-butanolate In tetrahydrofuran at 120℃; under 22502.3 Torr; for 26h; Schlenk technique; Glovebox; Autoclave;A 75%
B 80%
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen In tetrahydrofuran at 140℃; for 2h; Autoclave;A 99 %Chromat.
B 99 %Chromat.
With hydrogen In tetrahydrofuran at 159.84℃; under 45004.5 Torr; for 10h;

2453-03-4Relevant articles and documents

Mechanochemical synthesis of poly(trimethylene carbonate)s: An example of rate acceleration

Park, Sora,Kim, Jeung Gon

, p. 963 - 970 (2019)

Mechanochemical polymerization is a rapidly growing area and a number of polymeric materials can now be obtained through green mechanochemical synthesis. In addition to the general merits of mechanochemistry, such as being solvent-free and resulting in high conversions, we herein explore rate acceleration under ball-milling conditions while the conventional solution-state synthesis suffer from low reactivity. The solvent-free mechanochemical polymerization of trimethylene carbonate using the organocatalysts 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) are examined herein. The polymerizations under ball-milling conditions exhibited significant rate enhancements compared to polymerizations in solution. A number of milling parameters were evaluated for the ball-milling polymerization. Temperature increases due to ball collisions and exothermic energy output did not affect the polymerization rate significantly and the initial mixing speed was important for chain-length control. Liquid-assisted grinding was applied for the synthesis of high molecular weight polymers, but it failed to protect the polymer chain from mechanical degradation.

Experimental Evidence for the Stereoelectronically Controlled Hydrolysis of Orthocarbonates

Li, Shigui,Deslongchamps, Pierre

, p. 5641 - 5644 (1994)

The acid hydrolysis of cyclic and acyclic orthoesters 1-6 is reported.The results obtained are explained by taking into account the principle of stereoelectronic control.

Preparation and characterization of polyester- and poly(ester-carbonate)- paclitaxel conjugates

Sobczak, Marcin,Korzeniowska, Agnieszka,Go?, Piotr,Kolodziejski, Waclaw L.

, p. 3047 - 3051 (2011)

The polyester- and poly(ester-carbonate)-paclitaxel conjugates with low molecular weight were synthesized using dicyclohexylcarbodiimide (DCC) and dimethylaminopyridine (DMAP) as catalysts. Polymeric matrices were obtained by ring-opening polymerization of ε-caprolactone (CL), rac-lactide (rac-LA), l-lactide (LLA) and trimethylene carbonate (TMC). The macromolecular conjugates were characterized by using spectroscopic techniques, such as 1H, 13C NMR and FTIR. The degree of degradation of polyester- and poly(ester-carbonate)-paclitaxel conjugates was tested in vitro under different conditions. The preliminary results of drug release were discussed.

CYCLOADDITION OF OXETANE AND CARBON DIOXIDE CATALYZED BY TETRAPHENYLSTIBONIUM IODIDE

Baba, Akio,Kashiwagi, Hiroki,Matsuda, Haruo

, p. 1323 - 1324 (1985)

Trimethylene carbonate was readily obtained in the reaction of oxetane and carbon dioxide in the presence of tetraphenylstibonium iodide.

Selective formation of trimethylene carbonate (TMC): Atmospheric pressure Carbon dioxide utilization

Buckley, Benjamin R.,Patel, Anish P.,Wijayantha, K.G. Upul

, p. 474 - 478 (2015)

Carbon dioxide utilisation (CDU) is currently gaining increased interest due to the abundance of CO2 and its possible application as a C1 building block. We herein report the first example of atmospheric pressure carbon dioxide incorporation into oxetane to selectively form trimethylene carbonate (TMC), which is a significant challenge as TMC is thermodynamically less favoured than its corresponding co-polymer.

Ultrasound-assisted synthesis of a stable Co(II) coordination polymer as heterogeneous catalyst for CO2 transformation

Liu, Ce,Liu, Lin,Han, Zheng-Bo

, (2021)

A stable benzimidazole-containing Co(II) coordination polymer namely [Co(L)0.5(oba)]n (1) (H2oba = 4,4′-oxybis(benzoate), L = 1,6-bis(5,6-dimethylbenzimidazolyl) hexane) was successfully synthesized by ultrasonic technique under mild conditions. In especial, the effects of initial reagent concentration, irradiation time and ultrasonic power on the morphology and size of micron scale 1 were discussed in detail. Micron scale 1 appeared exceptional solvent and pH stabilities. Further, as a heterogeneous Lewis catalyst, 1 exhibited a highly activity and recyclability for CO2 transformation by cycloaddition with epoxide under room temperature.

PROCESS FOR THE SYNTHESIS OF ISOCYANATE-FREE OMEGA-HYDROXY-URETHANES, ALPHA-OMEGA-DIURETHANES AND OLIGO (POLY)URETHANES

-

Page/Page column 6-7, (2021/11/26)

The synthesis of omega-hydroxyalkyl-urethanes, and of alfa-omega-diurethanes is reported which includes the reaction of diols with urea in presence of catalysts based on Ce at temperatures between 125 and 170°C over 4-8 h reaction time. A process for the production of oligomers of omega-hydroxyalkyl-urethanes is also reported based on the reaction of urea with diols in presence of Ce or Zr catalysts or Ce mixed oxides at 125-170°C over 4-20 h.

Rational Design of Cobalt Complexes Based on the trans Effect of Hybrid Ligands and Evaluation of their Catalytic Activity in the Cycloaddition of Carbon Dioxide with Epoxide

Bu, Qingqing,Dai, Bin,Liu, Ning,Liu, Qiuli,Song, Wen-Yue,Wei, Donghui

, p. 3546 - 3561 (2020/11/02)

A series of cobalt complexes are presented as effective catalysts for the synthesis of cyclic carbonates from epoxides and CO2. The catalytic potentials of the cobalt complexes, in combination with tetrabutylammonium bromide, have been demonstrated to solve some challenges in the synthesis of cyclic carbonates, including the room-temperature conversion of terminal epoxides and activation-challenging substrates such as internal epoxides and fatty acid derived epoxides. A key factor in the success of the strategy is the use of cobalt complexes that are prepared on the basis of the trans effect of hybrid ligands. The trans effect between N-heterocyclic carbenes and acetylacetone has been proved by a number of spectroscopic measurements, including UV-vis, ESI-MS, EPR, and in situ FT-IR and by DFT calculations; these support the notion that acetylacetone prefers to dissociate from the cobalt center, which will result in one coordination site for the activation of a substrate molecule at the cobalt atom and thus give rise to high reactivity.

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