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707-61-9

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707-61-9 Usage

Chemical Properties

white to yellow adhering crystals

Uses

3-Methyl-1-phenyl-2-phospholene 1-oxide is used as a catalyst for intramolecular aza-wittig cyclization reactions and polymerization reactions. It is a reactant used for the preparation of phospha sugars and their radical bromination derivatives as anticancer agents.

Application

Catalyst for:Intramolecular aza-Wittig cyclization reactionsPolymerization reactionsReactant for preparation of:Phospha sugars and their radical bromination derivatives as anticancer agents

Check Digit Verification of cas no

The CAS Registry Mumber 707-61-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,0 and 7 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 707-61:
(5*7)+(4*0)+(3*7)+(2*6)+(1*1)=69
69 % 10 = 9
So 707-61-9 is a valid CAS Registry Number.
InChI:InChI=1/C11H13OP/c1-10-7-8-13(12,9-10)11-5-3-2-4-6-11/h2-6,9H,7-8H2,1H3/t13-/m0/s1

707-61-9 Well-known Company Product Price

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  • Alfa Aesar

  • (44726)  3-Methyl-1-phenyl-2-phospholene 1-oxide, 97%   

  • 707-61-9

  • 5g

  • 821.0CNY

  • Detail
  • Alfa Aesar

  • (44726)  3-Methyl-1-phenyl-2-phospholene 1-oxide, 97%   

  • 707-61-9

  • 25g

  • 3288.0CNY

  • Detail
  • Alfa Aesar

  • (44726)  3-Methyl-1-phenyl-2-phospholene 1-oxide, 97%   

  • 707-61-9

  • 100g

  • 10233.0CNY

  • Detail
  • Alfa Aesar

  • (A11792)  3-Methyl-1-phenyl-2-phospholene 1-oxide, 94%   

  • 707-61-9

  • 5g

  • 412.0CNY

  • Detail
  • Alfa Aesar

  • (A11792)  3-Methyl-1-phenyl-2-phospholene 1-oxide, 94%   

  • 707-61-9

  • 25g

  • 1441.0CNY

  • Detail
  • Alfa Aesar

  • (A11792)  3-Methyl-1-phenyl-2-phospholene 1-oxide, 94%   

  • 707-61-9

  • 100g

  • 5065.0CNY

  • Detail
  • Aldrich

  • (191744)  3-Methyl-1-phenyl-2-phospholene1-oxide  85%, technical grade

  • 707-61-9

  • 191744-10G

  • 800.28CNY

  • Detail

707-61-9SDS

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-Methyl-1-phenyl-2-phospholene 1-Oxide

1.2 Other means of identification

Product number -
Other names 3-methyl-1-phenyl-2-phospholene-1-oxide

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:707-61-9 SDS

707-61-9Synthetic route

Dichlorophenylphosphine
644-97-3

Dichlorophenylphosphine

isoprene
78-79-5

isoprene

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol In chloroform at 65℃; for 24h; Inert atmosphere; Sealed tube; Large scale;99.1%
McCormack reaction;68%
With 2,6-di-tert-butyl-4-methyl-phenol In toluene at 59 - 86℃; for 24h; Temperature; Inert atmosphere;5.204 g
2,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide
7564-51-4

2,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
With methanesulfonic acid at 50℃; for 60h; Reagent/catalyst; Temperature;81%
Multi-step reaction with 3 steps
1: oxalyl dichloride / dichloromethane / 0.25 h / 0 °C / Schlenk technique; Inert atmosphere
2: 72 h / 26 °C / Inert atmosphere; Schlenk technique
3: water / 24 h / 26 °C
View Scheme
With methanesulfonic acid at 50℃; for 60h;
Multi-step reaction with 3 steps
1: oxalyl dichloride / dichloromethane / 0.5 h / 0 °C
2: dichloromethane / 48 h / 50 °C / Sealed tube
3: water
View Scheme
Multi-step reaction with 3 steps
1: oxalyl dichloride / dichloromethane / 0.25 h / 0 °C / Inert atmosphere; Sealed tube
2: chloroform / 48 h / 80 °C
3: water / chloroform / 0.5 h / 0 °C
View Scheme
P,P-dichlorophenylphosphine oxide
824-72-6

P,P-dichlorophenylphosphine oxide

isoprene
78-79-5

isoprene

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
at 20℃; for 504000h;79%
for 168h; Ambient temperature;56%
1-chloro-3-methyl-1-phenyl-2-phospholenium salt
17154-12-0

1-chloro-3-methyl-1-phenyl-2-phospholenium salt

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
With water at 26℃; for 24h;71%
With water In chloroform64 g
phenylmagnesium bromide

phenylmagnesium bromide

1-chloro-3-methyl-2-phospholene 1-oxide
823-14-3

1-chloro-3-methyl-2-phospholene 1-oxide

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 6h;60%
Dichlorophenylphosphine
644-97-3

Dichlorophenylphosphine

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
46%
Multi-step reaction with 2 steps
1: 336 h / 20 °C
2: water / chloroform
View Scheme
3-methyl-1-phenylphosphole
30540-42-2

3-methyl-1-phenylphosphole

A

2,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide
7564-51-4

2,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide

B

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
With hydrogenchloride; water 1.) CD2Cl2, 2 days, 0 deg C, 2.) CD2Cl2, 30 min; Multistep reaction. Title compound not separated from byproducts;
1-methoxy-3-methyl-2-phospholene 1-oxide
695-60-3

1-methoxy-3-methyl-2-phospholene 1-oxide

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / 24 h / 20 °C
2: 60 percent / tetrahydrofuran / 6 h / 20 °C
View Scheme
1-chloro-3-methyl-1-phenyl-3-phospholenium chloride
104629-24-5

1-chloro-3-methyl-1-phenyl-3-phospholenium chloride

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
With water In chloroform at 0℃;
Multi-step reaction with 2 steps
1: chloroform / 48 h / 80 °C
2: water / chloroform / 0.5 h / 0 °C
View Scheme
isoprene
78-79-5

isoprene

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 336 h / 20 °C
2: water / chloroform
View Scheme
2-Methyl-1-butene
563-46-2

2-Methyl-1-butene

Dichlorophenylphosphine
644-97-3

Dichlorophenylphosphine

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
With water
1-chloro-3-methyl-1-phenyl-3-phospholenium chloride

1-chloro-3-methyl-1-phenyl-3-phospholenium chloride

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
With sodium hydroxide In water at 0℃; pH=6.5;
Multi-step reaction with 2 steps
1: 72 h / 26 °C / Inert atmosphere; Schlenk technique
2: water / 24 h / 26 °C
View Scheme
C11H13ClP*ClH

C11H13ClP*ClH

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane / 48 h / 50 °C / Sealed tube
2: water
View Scheme
C11H13ClP*ClH

C11H13ClP*ClH

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
With water
1-chloro-4-methyl-1-phenyl-2,3-dihydro-1H-phosphol-1-ium chloride
17786-49-1

1-chloro-4-methyl-1-phenyl-2,3-dihydro-1H-phosphol-1-ium chloride

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
With water In chloroform at 0℃; for 0.5h;
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-phosphole-1-oxide
34868-22-9

3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-phosphole-1-oxide

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 15001.5 Torr;100%
With hydrogen; palladium 10% on activated carbon In methanol at 20℃; under 15001.5 Torr;100%
With palladium 10% on activated carbon; hydrogen In methanol at 25℃; under 15001.5 Torr;99%
3CF3O3S(1-)*C15H21N6P2(3+)

3CF3O3S(1-)*C15H21N6P2(3+)

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

A

2CF3O3S(1-)*C10H14N4O4P4(2+)

2CF3O3S(1-)*C10H14N4O4P4(2+)

B

CF3O3S(1-)*C16H20N2P(1+)
1353778-65-0

CF3O3S(1-)*C16H20N2P(1+)

Conditions
ConditionsYield
In dichloromethane at 20℃; for 20h; Inert atmosphere;A 100%
B 100%
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide
1050329-20-8

2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide

Conditions
ConditionsYield
With manganese(II) bromide; bromine In dichloromethane at 20℃; for 1h;96%
With bromine; copper(ll) bromide In chloroform at 20℃; for 1h;90%
With manganese(IV) oxide; bromine In dichloromethane for 12h; Inert atmosphere;78%
With manganese(IV) oxide; bromine In dichloromethane at 20℃; for 12h;78%
With manganese(IV) oxide; bromine In dichloromethane at 20℃; for 12h;56%
dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

4-methyl-1-phenyl-2,3-dihydro-1H-phosphol-1-ane borane
179989-93-6

4-methyl-1-phenyl-2,3-dihydro-1H-phosphol-1-ane borane

Conditions
ConditionsYield
With trichlorosilane In dichloromethane N2-atmosphere; addn. of slight excess Me3SiH to oxide at 0°C, stirring for 6 h, removal of volatiles (vac.), addn. of equimolar amt. of borane at 0°C, stirring for 6 h; filtration, evapn.;95%
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

4-methyl-1-phenyl-2,3-dihydro-1H-phosphole
1445-83-6, 64822-29-3, 149443-46-9

4-methyl-1-phenyl-2,3-dihydro-1H-phosphole

Conditions
ConditionsYield
With hexylsilane; trifluorormethanesulfonic acid In toluene at 100℃; for 6h; Catalytic behavior; Temperature; Inert atmosphere; Sealed tube; chemoselective reaction;91%
Stage #1: 3-Methyl-1-phenyl-2-phospholene 1-oxide With trifluorormethanesulfonic acid In toluene at 20℃; for 0.0833333h;
Stage #2: With hexylsilane In toluene at 100℃; for 6h; Inert atmosphere;
91%
With methylpolysiloxane at 250℃;
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

(1S,2R,3S)-3-Methyl-1-oxo-1-phenyl-1λ5-phospholane-2,3-diol

(1S,2R,3S)-3-Methyl-1-oxo-1-phenyl-1λ5-phospholane-2,3-diol

cis-2,3-dihydroxy-3-methyl-1-phenylphospholane

cis-2,3-dihydroxy-3-methyl-1-phenylphospholane

Conditions
ConditionsYield
With osmium(VIII) oxide; potassium chlorate In tetrahydrofuran; water at 45 - 50℃; for 18h;A n/a
B 91%
ethylene glycol
107-21-1

ethylene glycol

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

2-bromo-3-(2-hydroxyethoxy)-3-methyl-1-phenylphospholane 1-oxide

2-bromo-3-(2-hydroxyethoxy)-3-methyl-1-phenylphospholane 1-oxide

Conditions
ConditionsYield
With bromine In chloroform at 20℃; for 48h;88%
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

3-hydroxy-2-(4,5-diethoxycarbonyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

3-hydroxy-2-(4,5-diethoxycarbonyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 16h; Heating;84%
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

1-(3'-nitrophenyl)-3-methyl-2-phospholene 1-oxide
91207-34-0

1-(3'-nitrophenyl)-3-methyl-2-phospholene 1-oxide

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 0 - 20℃; for 24h;80%
With sulfuric acid; nitric acid at 0 - 20℃; for 24h;80%
With sulfuric acid; nitric acid regioselective reaction;68%
With nitric acid In tetrachloromethane at 3 - 5℃;63%
dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

3-hydroxy-2-(4,5-dimethoxycarbonyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

3-hydroxy-2-(4,5-dimethoxycarbonyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 12h; Heating;79%
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

Acetylenedicarboxylic acid
142-45-0

Acetylenedicarboxylic acid

3-hydroxy-2-(4,5-dicarboxyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

3-hydroxy-2-(4,5-dicarboxyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 24h; Heating;79%
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

4-methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-sulfide
36044-21-0

4-methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-sulfide

Conditions
ConditionsYield
With tetraphosphorus decasulfide In benzene for 20h; Heating;75%
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

3-hydroxy-2-(4,5-dihydroxymethyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

3-hydroxy-2-(4,5-dihydroxymethyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 75h; Heating;68%
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

4-bromo-3-methyl-1-phenyl-2-phospholene 1-oxide
174078-54-7

4-bromo-3-methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chloroform for 6h; Reflux; Inert atmosphere;65%
Stage #1: 3-Methyl-1-phenyl-2-phospholene 1-oxide With N-Bromosuccinimide In chloroform at 50℃; Inert atmosphere;
Stage #2: With 2,2'-azobis(isobutyronitrile) In chloroform for 6h; Reflux; Inert atmosphere;
65%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 70℃; for 24h;65%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile)
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

diethylene glycol
111-46-6

diethylene glycol

2-bromo-3-(2-(2-hydroxyethoxy)ethoxy)-3-methyl-1-phenylphospholane 1-oxide
1438418-19-9

2-bromo-3-(2-(2-hydroxyethoxy)ethoxy)-3-methyl-1-phenylphospholane 1-oxide

Conditions
ConditionsYield
With bromine In chloroform at 20℃; for 48h;58%
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

(1R,2S,3R)-3-hydroxy-3-methyl-1-phenyl-2-(4'-trimethylsilyl-1'H-1',2',3'-triazo-1'-yl)-phospholane 1-oxide

(1R,2S,3R)-3-hydroxy-3-methyl-1-phenyl-2-(4'-trimethylsilyl-1'H-1',2',3'-triazo-1'-yl)-phospholane 1-oxide

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 24h; Heating;57%
1,4-epoxy-1,4-dihydronaphthalene
573-57-9

1,4-epoxy-1,4-dihydronaphthalene

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

C21H19OP

C21H19OP

Conditions
ConditionsYield
With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; silver(I) acetate In 1,2-dichloro-ethane at 130℃; for 12h; Sealed tube; Inert atmosphere;56%
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

2-Bromo-3-hydroxy-3-methyl-1-phenylphospholane 1-oxide
42408-51-5

2-Bromo-3-hydroxy-3-methyl-1-phenylphospholane 1-oxide

Conditions
ConditionsYield
With bromine; sodium hydroxide In chloroform; water at 20℃; for 72h;55%
With N-bromoacetamide In tetrahydrofuran; water for 36h; Ambient temperature;46%
With N-bromoacetamide In water
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

3-hydroxy-2-(4-t-butyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

3-hydroxy-2-(4-t-butyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

3-hydroxy-2-(5-t-butyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

3-hydroxy-2-(5-t-butyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 36h; Heating;A 55%
B 21%
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

methyl iodide
74-88-4

methyl iodide

3-ethyl-1-phenyl-2-phospholene 1-oxide
848484-65-1

3-ethyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
Stage #1: methyl iodide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;
Stage #2: 3-Methyl-1-phenyl-2-phospholene 1-oxide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
50%
propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

3-hydroxy-2-(4-methoxycarbonyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

3-hydroxy-2-(4-methoxycarbonyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

3-hydroxy-2-(5-methoxycarbonyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

3-hydroxy-2-(5-methoxycarbonyl-1H-1,2,3-triazol-1-yl)-3-methyl-1-phenylphospholane-1-oxide

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 12h; Heating;A 49%
B 37%
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

methyl iodide
74-88-4

methyl iodide

A

3-ethyl-1-phenyl-2-phospholene 1-oxide
848484-65-1

3-ethyl-1-phenyl-2-phospholene 1-oxide

2,3-dimethyl-1-phenyl-3-phospholene 1-oxide

2,3-dimethyl-1-phenyl-3-phospholene 1-oxide

Conditions
ConditionsYield
Stage #1: 3-Methyl-1-phenyl-2-phospholene 1-oxide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h;
Stage #2: methyl iodide In tetrahydrofuran at -78℃; for 0.5h;
A 6%
B 49%
methanol
67-56-1

methanol

3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

(+/-)-threo-1-phenyl-2-bromo-3-methoxy-3-methylphospholane 1-oxide

(+/-)-threo-1-phenyl-2-bromo-3-methoxy-3-methylphospholane 1-oxide

(+/-)-erythro-1-phenyl-2-bromo-3-methoxy-3-methylphospholane 1-oxide

(+/-)-erythro-1-phenyl-2-bromo-3-methoxy-3-methylphospholane 1-oxide

(1S,2S,3S)-3-Bromo-2-methoxy-3-methyl-1-phenyl-phospholane 1-oxide

(1S,2S,3S)-3-Bromo-2-methoxy-3-methyl-1-phenyl-phospholane 1-oxide

(1S,2R,3R)-3-Bromo-2-methoxy-3-methyl-1-phenyl-phospholane 1-oxide

(1S,2R,3R)-3-Bromo-2-methoxy-3-methyl-1-phenyl-phospholane 1-oxide

Conditions
ConditionsYield
With bromine In chloroform at 20℃; for 72h;A 47%
B 45%
C n/a
D n/a
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

(+/-)-threo 2-bromo-3-hydroxy-3-methyl-1-phenylphospholane 1-oxide

(+/-)-threo 2-bromo-3-hydroxy-3-methyl-1-phenylphospholane 1-oxide

(+/-)-erythro 2-bromo-3-hydroxy-3-methyl-1-phenylphospholane 1-oxide

(+/-)-erythro 2-bromo-3-hydroxy-3-methyl-1-phenylphospholane 1-oxide

Conditions
ConditionsYield
With bromine In chloroform; water at 20℃; for 72h; Addition;A 46%
B n/a
With water; bromine In chloroform at 20℃; for 48h;
3-Methyl-1-phenyl-2-phospholene 1-oxide
707-61-9

3-Methyl-1-phenyl-2-phospholene 1-oxide

threo-2-bromo-3-hydroxy-3-methyl-1-phenyl-2-phospholene 1-oxide

threo-2-bromo-3-hydroxy-3-methyl-1-phenyl-2-phospholene 1-oxide

Conditions
ConditionsYield
With water; bromine In chloroform at 20℃; for 72h;46%

707-61-9Relevant articles and documents

Synthesis of novel deoxy λ5 phospha sugar nucleosides: 1,3-dipolar cycloaddition of an azidophospholane with alkynes

Yamashita, Mitsuji,Mallikarjuna Reddy, Putta,Kato, Yukihiro,Krishna Reddy, Valluru,Suzuki, Kazumitsu,Oshikawa, Tatsuo

, p. 257 - 270 (2001)

Several novel phospha sugar nucleosides, analogs of normal sugar nucleosides, were synthesized from a phospholene 1-oxide derivative. Bromination of a phospholene precursor in aqueous organic medium gave regio diastereomers, the threo and erythro bromohydrins 3 (1-bromo-1,3,4-trideoxy-1,4-C-[(R,S)-phenylphosphinylidene]-glycero- tetrofuranose). Further substitution of the threo isomer 3a with sodium azide led to its corresponding azidophospholane 4 (1-azido-1,3,4-trideoxy-2-methyl-1,4-C-[(R)-phenylphosphinylidene]-β-D- glycero-tetrofuranose). 1,3-Dipolar cycloaddition of 4 with various electron-deficient and electron-rich alkynes afforded triazole derivatives that are nucleoside analogues. The strong electron-withdrawing phosphoryl group in the hemiacetal ring exerted no effect over reaction regioselectivity of the 1,3-dipolar cycloaddition, but steric effects of the alkynes played a vital role on the selectivity, since the regioisomer ratios and the rates and yields of cycloadducts changed as the bulkiness of the substituents on the acetylene changes. Structures of all compounds were unequivocally confirmed by 1H, 13C, and 31P NMR and mass spectral studies. Single crystal X-ray crystallographic analysis of some derivatives allowed determination of configuration of the phospha sugar nucleosides.

Isomerization and application of phospholene oxides

Herbay, Réka,Péczka, Nikolett,Gy?rke, Gábor,Bagi, Péter,Fogassy, Elemér,Keglevich, Gy?rgy

, p. 610 - 613 (2019/01/05)

In this research, an investigation of the isomerization and the applications of 3-phospholene oxides were elaborated. The isomerization of 3-phospholene oxides to 2-phospholene oxides was investigated under thermal condition. The application of bases and acids was also tested in this reaction. Moreover, the isomerization was also elaborated via the formation of halophosphonium salt intermediates. The 3-phospholene oxides were deoxygenated and transformed to the corresponding palladium complexes.

A novel preparation of chlorophospholenium chlorides and their application in the synthesis of phospholene boranes

Herbay, Réka,Bagi, Péter,Mucsi, Zoltán,Mátrav?lgyi, Béla,Drahos, László,Fogassy, Elemér,Keglevich, Gy?rgy

, p. 458 - 461 (2017/01/11)

A novel preparation of 1-chloro-3-methyl-3-phospholenium chlorides was developed by reacting 1-substituted-3-methyl-3-phospholene 1-oxides with oxalyl chloride. The obtained cyclic chlorophosphonium salts were reacted with LiBH4to afford the corresponding 1-substituted-3-methyl-3-phospholene boranes. The latter protocol involves a silane-free deoxygenation, and borane complex formation. In one instance, a 2-phospholene borane and the corresponding P-oxide were synthesized via rearrangement of the double bond in the cyclic chlorophosphonium salt. This double bond migration was investigated by quantum chemical calculations.

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