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930-22-3

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930-22-3 Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

Butadiene monoxide is used as key starting material for the synthesis of (-)-bulgecinine and (+)-broussonetine G.

Reactivity Profile

BUTADIENE MONOXIDE may be sensitive to heat. BUTADIENE MONOXIDE can react with oxidizing materials. . Epoxides are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

Health Hazard

ACUTE/CHRONIC HAZARDS: BUTADIENE MONOXIDE emits acrid fumes when heated to decomposition.

Fire Hazard

BUTADIENE MONOXIDE is flammable.

Safety Profile

A poison by intraperitoneal route. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. A very dangerous fire hazard when exposed to heat or flame; can react with oxidzing materials. To fight fire, use CO2, dry chemical, water spray. When heated to decomposition it emits acrid smoke and fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 930-22-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,3 and 0 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 930-22:
(5*9)+(4*3)+(3*0)+(2*2)+(1*2)=63
63 % 10 = 3
So 930-22-3 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O/c1-2-4-3-5-4/h2,4H,1,3H2/t4-/m0/s1

930-22-3 Well-known Company Product Price

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

  • (L00238)  Butadiene monoxide, 98%   

  • 930-22-3

  • 1g

  • 448.0CNY

  • Detail
  • Alfa Aesar

  • (L00238)  Butadiene monoxide, 98%   

  • 930-22-3

  • 5g

  • 1403.0CNY

  • Detail
  • Alfa Aesar

  • (L00238)  Butadiene monoxide, 98%   

  • 930-22-3

  • 25g

  • 5501.0CNY

  • Detail
  • Aldrich

  • (127574)  3,4-Epoxy-1-butene  98%

  • 930-22-3

  • 127574-1G

  • 1,012.05CNY

  • Detail
  • Aldrich

  • (127574)  3,4-Epoxy-1-butene  98%

  • 930-22-3

  • 127574-5G

  • 3,133.26CNY

  • Detail

930-22-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3,4-Epoxy-1-butene

1.2 Other means of identification

Product number -
Other names Oxirane, ethenyl-

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:930-22-3 SDS

930-22-3Synthetic route

Conditions
ConditionsYield
Stage #1: With sodium oxalate; oxalic acid; manganese(II) acetate; N,N',N''-trimethyl-1,4,7-triazacyclononane In water
Stage #2: buta-1,3-diene With dihydrogen peroxide In water at -40 - 25℃; under 2400.24 - 3900.39 Torr; for 8.5h; Cooling with acetone-dry ice;
A n/a
B 95.5%
buta-1,3-diene
106-99-0

buta-1,3-diene

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
With [N,N'-bis(salicylidene)-1,2-ethanediaminato]Mn(III) chloride; iodosylbenzene In dichloromethane92%
With dihydrogen peroxide; teterabutylammonium In acetonitrile at 31.85℃; for 9h;91%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 45℃; for 48h;
(2-bromoethyl)oxirane
13287-42-8

(2-bromoethyl)oxirane

sodium diethylmalonate
996-82-7, 34727-00-9, 73177-21-6

sodium diethylmalonate

ethanol
64-17-5

ethanol

epoxybutene
930-22-3

epoxybutene

1-chloro-2-hydroxy-3-butene
671-56-7

1-chloro-2-hydroxy-3-butene

sodium methylate
124-41-4

sodium methylate

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
bei Raumtemperatur in 35 min;
peracetic acid
79-21-0

peracetic acid

diethyl ether
60-29-7

diethyl ether

buta-1,3-diene
106-99-0

buta-1,3-diene

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
at 17 - 18℃; Geschwindigkeit;
peracetic acid
79-21-0

peracetic acid

buta-1,3-diene
106-99-0

buta-1,3-diene

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
With ethyl acetate
With acetone
Perbenzoic acid
93-59-4

Perbenzoic acid

buta-1,3-diene
106-99-0

buta-1,3-diene

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
With chloroethane
diacetyl peroxide
110-22-5

diacetyl peroxide

buta-1,3-diene
106-99-0

buta-1,3-diene

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
With diethyl ether
1,4-dichloro-2-butene
764-41-0

1,4-dichloro-2-butene

A

epoxybutene
930-22-3

epoxybutene

B

1-chloroprene
627-22-5

1-chloroprene

D

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N-dodecyl-N,N-bis(beta-hydroxyethyl)ammonium chloride at 60 - 90℃; Product distribution; Kinetics; Thermodynamic data; further catalyst and base; E(excit.);
(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
With diethoxyltriphenylphosphorane In chloroform-d1 at 61℃; for 18h; Yield given;
(2E)-4-bromobut-2-en-1-yl acetate
33746-94-0

(2E)-4-bromobut-2-en-1-yl acetate

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
With potassium hydroxide at 60 - 80℃; for 0.333333h; Yield given;
With potassium hydroxide Yield given;
(E)-1-chloro-4-acetoxybut-2-ene
34414-28-3

(E)-1-chloro-4-acetoxybut-2-ene

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
With potassium hydroxide at 60 - 80℃; for 0.333333h; Yield given;
With potassium hydroxide
4-bromo-3-buten-1-ol

4-bromo-3-buten-1-ol

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
With sodium hydroxide at 90℃;
buta-1,3-diene
106-99-0

buta-1,3-diene

A

epoxybutene
930-22-3

epoxybutene

B

3-butenal
7319-38-2

3-butenal

C

nitrogen(II) oxide
10102-43-9

nitrogen(II) oxide

Conditions
ConditionsYield
With Nitrogen dioxide In solid matrix Mechanism; Rate constant; Irradiation; Ar matrix;
Conditions
ConditionsYield
With B single-collision conditions;
tert-amyl hydroperoxide
3425-61-4

tert-amyl hydroperoxide

buta-1,3-diene
106-99-0

buta-1,3-diene

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
With molybdenum propylene glycolate at 80℃; kinetic studies; var. conc. of peroxide and molybdenum glycolate;
buta-1,3-diene
106-99-0

buta-1,3-diene

A

epoxybutene
930-22-3

epoxybutene

B

acrolein
107-02-8

acrolein

C

(E)-4-Nitrooxy-but-2-enal

(E)-4-Nitrooxy-but-2-enal

D

(E)-4-Nitrooxy-but-2-en-1-yl-hydroperoxide

(E)-4-Nitrooxy-but-2-en-1-yl-hydroperoxide

Conditions
ConditionsYield
With Nitrogen dioxide; dinitrogen pentoxide; nitrate radical at 298℃; under 740 Torr; Product distribution; Further Variations:; Reagents; Oxidation; Nitration; Photolysis;
(+-)-1-bromo-but-3-en-2-ol

(+-)-1-bromo-but-3-en-2-ol

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
With sodium hydroxide
With potassium hydroxide
(+-)-1-chloro-but-3-en-2-ol

(+-)-1-chloro-but-3-en-2-ol

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
With sodium hydroxide
With potassium hydroxide
(+-)-3-acetoxy-tetrahydro-furan

(+-)-3-acetoxy-tetrahydro-furan

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
With hydrogen bromide Behandeln des Reaktionsprodukts mit Kaliumhydroxid;
(+-)-4-chloro-1,2-epoxy-butane

(+-)-4-chloro-1,2-epoxy-butane

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
With sodium hydroxide
<β-bromo-ethyl>-ethylene oxide

<β-bromo-ethyl>-ethylene oxide

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
With potassium hydroxide
(2-bromoethyl)oxirane
13287-42-8

(2-bromoethyl)oxirane

potassium hydroxide

potassium hydroxide

epoxybutene
930-22-3

epoxybutene

3-Acetoxy-4-bromo-1-butene
34414-26-1

3-Acetoxy-4-bromo-1-butene

alkaline solution

alkaline solution

epoxybutene
930-22-3

epoxybutene

Conditions
ConditionsYield
at 100℃;
1-chloro-2-hydroxy-3-butene
671-56-7

1-chloro-2-hydroxy-3-butene

KOH

KOH

epoxybutene
930-22-3

epoxybutene

acetic acid-(1-chloromethyl-allyl ester)
13422-63-4

acetic acid-(1-chloromethyl-allyl ester)

KOH

KOH

epoxybutene
930-22-3

epoxybutene

4-acetoxy-3-chloro-1-butene
96039-67-7

4-acetoxy-3-chloro-1-butene

potassium hydroxide

potassium hydroxide

epoxybutene
930-22-3

epoxybutene

1-chloro-2-hydroxy-3-butene
671-56-7

1-chloro-2-hydroxy-3-butene

NaHCO3

NaHCO3

A

epoxybutene
930-22-3

epoxybutene

B

3,4-butenediol
497-06-3

3,4-butenediol

C

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

buta-1,3-diene
106-99-0

buta-1,3-diene

A

epoxybutene
930-22-3

epoxybutene

B

furan
110-00-9

furan

C

carbon dioxide
124-38-9

carbon dioxide

D

crotonaldehyde
123-73-9

crotonaldehyde

Conditions
ConditionsYield
With oxygen; aluminum oxide; silver at 270℃; Product distribution; Further Variations:; butadiens: 2,3-d2; 1,1,4,4-d4; d6;
epoxybutene
930-22-3

epoxybutene

methanol
67-56-1

methanol

2-(R)-2-Methoxybut-3-en-1-ol
18231-00-0

2-(R)-2-Methoxybut-3-en-1-ol

Conditions
ConditionsYield
With aluminium(III) triflate at 100℃; for 1h; regioselective reaction;100%
Stage #1: epoxybutene; methanol at 0℃; for 0.5h;
Stage #2: With sulfuric acid at 0 - 20℃; for 3h;
25%
With boron trifluoride diethyl etherate
epoxybutene
930-22-3

epoxybutene

piperidine-2,6-dione
1121-89-7

piperidine-2,6-dione

1-[(1R)-1-(hydroxymethyl)-2-propenyl]-2,6-piperidinedinone
1182277-91-3

1-[(1R)-1-(hydroxymethyl)-2-propenyl]-2,6-piperidinedinone

Conditions
ConditionsYield
Stage #1: piperidine-2,6-dione With bis(η3-allyl-μ-chloropalladium(II)); N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; sodium carbonate In dichloromethane at 20℃; for 1.16667h; Inert atmosphere;
Stage #2: epoxybutene In dichloromethane at 20℃; for 14h; Inert atmosphere; optical yield given as %ee; regioselective reaction;
100%
epoxybutene
930-22-3

epoxybutene

4-(mercaptomethyl)-4-methyloxazolidin-2-one

4-(mercaptomethyl)-4-methyloxazolidin-2-one

4-((2-hydroxybut-3-enyl)thiomethyl)-4-methyloxazolidin-2-one
1373434-39-9

4-((2-hydroxybut-3-enyl)thiomethyl)-4-methyloxazolidin-2-one

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 14h;100%
epoxybutene
930-22-3

epoxybutene

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

1-amino-2-propene

N-allyl-N-(2-hydroxy-but-3-enyl)-carbamic acid tert-butyl ester
224779-26-4

N-allyl-N-(2-hydroxy-but-3-enyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: epoxybutene; 1-amino-2-propene In water at 80℃; for 6h;
Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In 1,4-dioxane; water at 20℃;
100%
Stage #1: epoxybutene; 1-amino-2-propene In water at 100℃; for 6h;
Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In 1,4-dioxane; water at 20℃; for 12h;
56%
epoxybutene
930-22-3

epoxybutene

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-methylallylamin
2878-14-0

2-methylallylamin

tert-butyl (2-hydroxybut-3-en-1-yl)(2-methylallyl)carbamate

tert-butyl (2-hydroxybut-3-en-1-yl)(2-methylallyl)carbamate

Conditions
ConditionsYield
Stage #1: epoxybutene; 2-methylallylamin In water at 80℃; for 6h;
Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In 1,4-dioxane; water at 20℃;
100%
epoxybutene
930-22-3

epoxybutene

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

(1-Chloromethyl-allyloxy)-trimethyl-silane
80717-11-9

(1-Chloromethyl-allyloxy)-trimethyl-silane

Conditions
ConditionsYield
triphenylphosphine In chloroform at -50℃; for 0.25h;99%
epoxybutene
930-22-3

epoxybutene

N-(4-methylbenzylidene)-p-toluenesulfonamide
75159-10-3

N-(4-methylbenzylidene)-p-toluenesulfonamide

2-(4-methylphenyl)-N-tosyl-4-vinyloxazolidine

2-(4-methylphenyl)-N-tosyl-4-vinyloxazolidine

Conditions
ConditionsYield
With 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran for 4h; Ambient temperature;99%
epoxybutene
930-22-3

epoxybutene

(E)-N-4-methylbenzylidene-4-toluenesulfonamide
75159-10-3

(E)-N-4-methylbenzylidene-4-toluenesulfonamide

2-(4-methylphenyl)-N-tosyl-4-vinyloxazolidine

2-(4-methylphenyl)-N-tosyl-4-vinyloxazolidine

Conditions
ConditionsYield
With 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 4h; Cycloaddition;99%
epoxybutene
930-22-3

epoxybutene

benzyl chloroformate
501-53-1

benzyl chloroformate

((E)-4-hydroxy-but-2-enyl)-carbamic acid benzyl ester
1075689-58-5

((E)-4-hydroxy-but-2-enyl)-carbamic acid benzyl ester

Conditions
ConditionsYield
Stage #1: epoxybutene In benzene-d6 at 23℃;
Stage #2: benzyl chloroformate With potassium carbonate In tetrahydrofuran; benzene-d6 at 23℃; for 12h; Further stages.;
99%
epoxybutene
930-22-3

epoxybutene

poly(3,4-epoxy-1-butene)

poly(3,4-epoxy-1-butene)

Conditions
ConditionsYield
C64H74Cl2Co2N4O4; bis(triphenylphosphoranylidene)-ammonium acetate In toluene at 0℃; for 21h;99%
epoxybutene
930-22-3

epoxybutene

phthalimide
136918-14-4

phthalimide

(+)-2-[(1R)-(hydroxymethyl)prop-2-enyl]-1H-isoindole-1,3-(2H)-dione
174810-06-1

(+)-2-[(1R)-(hydroxymethyl)prop-2-enyl]-1H-isoindole-1,3-(2H)-dione

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; sodium carbonate optical yield given as %ee;99%
With bis(η3-allyl-μ-chloropalladium(II)); N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; sodium carbonate optical yield given as %ee; enantioselective reaction;99%
Stage #1: phthalimide With bis(η3-allyl-μ-chloropalladium(II)); N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; sodium carbonate In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: epoxybutene In dichloromethane at 20℃; for 14h; Inert atmosphere;
99%
Stage #1: phthalimide With bis(η3-allyl-μ-chloropalladium(II)); N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; sodium carbonate In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: epoxybutene In dichloromethane at 20℃; for 12h; Inert atmosphere;
97%
With bis(η3-allyl-μ-chloropalladium(II)); N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; sodium carbonate In dichloromethane at 20℃; Inert atmosphere; enantioselective reaction;92%
epoxybutene
930-22-3

epoxybutene

tert-butyl N-(trifluoroacetyl)glycinate
63959-88-6

tert-butyl N-(trifluoroacetyl)glycinate

C13H20F3NO4

C13H20F3NO4

Conditions
ConditionsYield
Stage #1: tert-butyl N-(trifluoroacetyl)glycinate With zinc(II) chloride; lithium hexamethyldisilazane Inert atmosphere;
Stage #2: epoxybutene With bis(η3-allyl-μ-chloropalladium(II)); triphenylphosphine In tetrahydrofuran at -78 - 20℃; for 16h; Inert atmosphere;
99%
epoxybutene
930-22-3

epoxybutene

1-benzylisatin
1217-89-6

1-benzylisatin

dimethyl-1'-methyl-2'-oxo-5-((E)-styryl)-4,5-dihydro-3H-spiro[furan-2,3'-indoline]-3,3-dicarboxylate

dimethyl-1'-methyl-2'-oxo-5-((E)-styryl)-4,5-dihydro-3H-spiro[furan-2,3'-indoline]-3,3-dicarboxylate

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); (4R,5R)-2-((S)-1-(2-(dibutylphosphino)naphthalen-1-yl)naphthalen-2-yl)-4,5-diphenyl-1-tosyl-4,5-dihydro-1H-imidazole In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; Schlenk technique;99%
epoxybutene
930-22-3

epoxybutene

(E)-1-phenyl-2-buten-1-one
35660-91-4, 35845-66-0, 495-41-0

(E)-1-phenyl-2-buten-1-one

(2-methyl-4-vinyltetrahydrofuran-3-yl)(phenyl)methanone

(2-methyl-4-vinyltetrahydrofuran-3-yl)(phenyl)methanone

Conditions
ConditionsYield
With 5,5’-bis(diphenylphosphino)-2,2,2’,2’-tetrafluoro-4,4’-bi-1,3-benzodioxole; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In 1,4-dioxane at 15℃; for 120h; Inert atmosphere; Sealed tube; stereoselective reaction;99%
epoxybutene
930-22-3

epoxybutene

trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

Conditions
ConditionsYield
With lithium phosphate In hexane at 310℃; Isomerization;98.9%
epoxybutene
930-22-3

epoxybutene

3-Methyl-2-butenyl-trimethylstannane
17314-40-8

3-Methyl-2-butenyl-trimethylstannane

3,3-Dimethyl-2-vinyl-pent-4-en-1-ol
81812-73-9

3,3-Dimethyl-2-vinyl-pent-4-en-1-ol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at -78℃; for 0.5h;98%
epoxybutene
930-22-3

epoxybutene

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

N-phenyl-3-phenyl-4-vinyl-1,3-oxazolidin-2-imine
121485-54-9

N-phenyl-3-phenyl-4-vinyl-1,3-oxazolidin-2-imine

Conditions
ConditionsYield
With triphenylphosphine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 15h; Ambient temperature;98%
tetraphenyl stibonium iodide In benzene at 40℃; for 29h;62%
With (R)-C1-TunePhos; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran at 20℃; Product distribution; Further Variations:; Reagents;
epoxybutene
930-22-3

epoxybutene

phthalimide
136918-14-4

phthalimide

(-)-2-[(1S)-(hydroxymethyl)prop-2-enyl]-1H-isoindole-1,3-(2H)-dione
174810-05-0

(-)-2-[(1S)-(hydroxymethyl)prop-2-enyl]-1H-isoindole-1,3-(2H)-dione

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); R,R-C52H44N2O2P2 chiral ligand; sodium carbonate In dichloromethane for 14h; Ambient temperature;98%
With sodium carbonate; (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl); bis(η3-allyl-μ-chloropalladium(II)) In dichloromethane at 20℃; for 14h; ring cleavage;98%
With bis(η3-allyl-μ-chloropalladium(II)); sodium carbonate; (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl) In dichloromethane at 20℃; for 22h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;98%
epoxybutene
930-22-3

epoxybutene

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

3-(4-chlorophenyl)-4-vinyloxazolidin-2-one
115148-33-9

3-(4-chlorophenyl)-4-vinyloxazolidin-2-one

Conditions
ConditionsYield
With triphenylphosphine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 15h; Ambient temperature;98%
epoxybutene
930-22-3

epoxybutene

2,5-dihydrofuran
1708-29-8

2,5-dihydrofuran

Conditions
ConditionsYield
at 130 - 140℃; under 760.051 Torr;98%
at 120 - 140℃; under 760.051 Torr;98%
at 130℃; under 760.051 Torr;98%
epoxybutene
930-22-3

epoxybutene

dimethyl allylmalonate
40637-56-7

dimethyl allylmalonate

dimethyl allyl(4-hydroxy-2E-butenyl)malonate
158627-63-5

dimethyl allyl(4-hydroxy-2E-butenyl)malonate

Conditions
ConditionsYield
With Pd2(dba)4; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 20℃; for 3h;98%
epoxybutene
930-22-3

epoxybutene

1-hydroxy-2-iodo-3-butene
127201-32-5

1-hydroxy-2-iodo-3-butene

Conditions
ConditionsYield
With water; hydrogen iodide at 0℃; for 0.166667h; Darkness;98%
epoxybutene
930-22-3

epoxybutene

bis(phenylsulfonyl)methane
3406-02-8

bis(phenylsulfonyl)methane

C17H18O5S2

C17H18O5S2

Conditions
ConditionsYield
With 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 20℃; for 5h;98%
epoxybutene
930-22-3

epoxybutene

ethyl 2-benzylidene acetoacetate
620-80-4

ethyl 2-benzylidene acetoacetate

C17H20O4
1338338-58-1

C17H20O4

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); (E)-N-cyclohexyl-1-(2-(diphenylphosphanyl)phenyl)methanimine In toluene at 30℃; for 24h;98%
epoxybutene
930-22-3

epoxybutene

carbon dioxide
124-38-9

carbon dioxide

4-vinyl-1,3-dioxolan-2-one
4427-96-7

4-vinyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
With 1-methyl-3-(3-phenylthioureido)pyridinium iodide; tetra-(n-butyl)ammonium iodide at 60℃; Sealed tube;97%
With dmap; C40H49AlN4O4S2 at 20 - 120℃; under 750.075 Torr; for 8h; Catalytic behavior; Autoclave;97%
With calcium iodide In neat (no solvent) at 25℃; under 7500.75 Torr; for 24h;95%
epoxybutene
930-22-3

epoxybutene

phenylmercury(II) chloride
100-56-1

phenylmercury(II) chloride

4-phenyl-2-buten-1-ol
42238-15-3

4-phenyl-2-buten-1-ol

Conditions
ConditionsYield
With lithium chloride; copper dichloride; palladium dichloride In tetrahydrofuran; water 0 deg C, 10-12 h then 25 deg C, 2-3 h;97%
epoxybutene
930-22-3

epoxybutene

benzaldehyde
100-52-7

benzaldehyde

(2E)-5-phenylpent-2-ene-1,5-diol
104683-49-0

(2E)-5-phenylpent-2-ene-1,5-diol

Conditions
ConditionsYield
With carbon monoxide; tetrabutylammomium bromide; water; triethylamine; dodecacarbonyl-triangulo-triruthenium In 1,4-dioxane at 75℃; under 2068.65 Torr; for 20h; Product distribution / selectivity; Autoclave;97%
With rhodium(III) chloride hydrate; carbon monoxide; tetrabutyl-ammonium chloride; water; triethylamine In 1,4-dioxane at 75℃; under 2068.65 Torr; for 24h; Reagent/catalyst; Inert atmosphere; diastereoselective reaction;88%
epoxybutene
930-22-3

epoxybutene

1-phenylethenylmagnesium bromide
67300-99-6

1-phenylethenylmagnesium bromide

(E)-5-phenyl-hexa-2,5-dien-1-ol
1609173-14-9

(E)-5-phenyl-hexa-2,5-dien-1-ol

Conditions
ConditionsYield
With copper(l) cyanide In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere;97%
epoxybutene
930-22-3

epoxybutene

N-methyl-α-phenylnitrone
3376-23-6

N-methyl-α-phenylnitrone

2-methyl-3-phenyl-6-vinyl-1,4,2-dioxazinane

2-methyl-3-phenyl-6-vinyl-1,4,2-dioxazinane

Conditions
ConditionsYield
With aluminum (III) chloride In acetonitrile at 40℃; for 7h; Inert atmosphere; diastereoselective reaction;97%
epoxybutene
930-22-3

epoxybutene

C8H9NO3S

C8H9NO3S

9-methyl-3-vinyl-3,10b-dihydro-2H-benzo[e]oxazolo[3,2-c][1,2,3]oxathiazine5,5-dioxide

9-methyl-3-vinyl-3,10b-dihydro-2H-benzo[e]oxazolo[3,2-c][1,2,3]oxathiazine5,5-dioxide

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tetrabutylammomium bromide; bis[2-(diphenylphosphino)phenyl] ether In dichloromethane at 20℃; for 6h; Inert atmosphere; Schlenk technique; diastereoselective reaction;97%

930-22-3Relevant articles and documents

An Amphiphilic (salen)Co Complex – Utilizing Hydrophobic Interactions to Enhance the Efficiency of a Cooperative Catalyst

Solís-Mu?ana, Pablo,Salam, Joanne,Ren, Chloe Z.-J.,Carr, Bronte,Whitten, Andrew E.,Warr, Gregory G.,Chen, Jack L.-Y.

supporting information, p. 3207 - 3213 (2021/06/01)

An amphiphilic (salen)Co(III) complex is presented that accelerates the hydrolytic kinetic resolution (HKR) of epoxides almost 10 times faster than catalysts from commercially available sources. This was achieved by introducing hydrophobic chains that increase the rate of reaction in one of two ways – by enhancing cooperativity under homogeneous conditions, and increasing the interfacial area under biphasic reaction conditions. While numerous strategies have been employed to increase the efficiency of cooperative catalysts, the utilization of hydrophobic interactions is scarce. With the recent upsurge in green chemistry methods that conduct reactions ‘on water’ and at the oil-water interface, the introduction of hydrophobic interactions has potential to become a general strategy for enhancing the catalytic efficiency of cooperative catalytic systems. (Figure presented.).

Enantioselective Radical-Polar Crossover Reactions of Indanonecarboxamides with Alkenes

Cao, Weidi,Feng, Xiaoming,Liu, Xiaohua,Wu, Wangbin,Xu, Xi,Yu, Han,Zhang, Xiying

supporting information, p. 4846 - 4850 (2020/02/11)

Highly efficient asymmetric intermolecular radical-polar crossover reactions were realized by combining a chiral N,N′-dioxide/NiII complex catalyst with Ag2O under mild reaction conditions. Various terminal alkenes and indanonecarboxamides/esters underwent radical addition/cyclization reactions to afford spiro-iminolactones and spirolactones with good to excellent yields (up to 99 %) and enantioselectivities (up to 97 % ee). Furthermore, a range of different radical-mediated oxidation/elimination or epoxide ring-opening products were obtained under mild reaction conditions. The Lewis acid catalysts exhibited excellent performance and precluded the strong background reaction.

Precursor effect on the property and catalytic behavior of Fe-TS-1 in butadiene epoxidation

Wu, Mei,Zhao, Huahua,Yang, Jian,Zhao, Jun,Song, Huanling,Chou, Lingjun

, p. 2103 - 2109 (2017/10/06)

The effect of iron precursor on the property and catalytic behavior of iron modified titanium silicalite molecular sieve (Fe-TS-1) catalysts in butadiene selective epoxidation has been studied. Three Fe-TS-1 catalysts were prepared, using iron nitrate, iron chloride and iron sulfate as precursors, which played an important role in adjusting the textural properties and chemical states of TS-1. Of the prepared Fe-TS-1 catalysts, those modified by iron nitrate (FN-TS-1) exhibited a significant enhanced performance in butadiene selective epoxidation compared to those derived from iron sulfate (FS-TS-1) or iron chloride (FC-TS-1) precursors. To obtain a deep understanding of their structure-performance relationship, X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), Temperature programmed desorption of NH3 (NH3-TPD), Diffuse reflectance UV–Vis spectra (DR UV–Vis), Fourier transformed infrared spectra (FT-IR) and thermal gravimetric analysis (TGA) were conducted to characterize Fe-TS-1 catalysts. Experimental results indicated that textural structures and acid sites of modified catalysts as well as the type of Fe species influenced by the precursors were all responsible for the activity and product distribution.

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