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707-61-9

Basic Information
CAS No.: 707-61-9
Name: 1H-Phosphole,2,3-dihydro-4-methyl-1-phenyl-, 1-oxide
Molecular Structure:
Molecular Structure of 707-61-9 (1H-Phosphole,2,3-dihydro-4-methyl-1-phenyl-, 1-oxide)
Formula: C11H13 O P
Molecular Weight: 192.21
Synonyms: 2-Phospholene,3-methyl-1-phenyl-, 1-oxide (7CI,8CI);1-Oxo-1-phenyl-3-methyl-2-phospholene;1-Oxo-3-methyl-1-phenyl-2-phospholene;1-Phenyl-3-methyl-2-phospholene 1-oxide;2,3-Dihydro-4-methyl-1-phenyl-1H-phosphole 1-oxide;3-Methyl-1-phenyl-2-phospholene 1-oxide;NSC 107634;4 ,5-Dihydro-3-methyl-1-phenylphosphole 1-oxide;
EINECS: 211-901-5
Density: 1.11 g/cm3
Melting Point: 58-62ºC
Boiling Point: 150 ºC.15 mm Hg(lit.)
Flash Point: 113 ºC
Solubility:
Appearance:
Hazard Symbols:
Risk Codes: R20/21/22;R36/37/38;R40   
Safety: Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic vapors of POx.
Transport Information:
PSA: 26.88000
LogP: 2.98250
Synthetic route
644-97-3

Dichlorophenylphosphine

78-79-5

isoprene

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
7564-51-4

2,5-dihydro-3-methyl-1-phenyl-1H-phosphole 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
824-72-6

P,P-dichlorophenylphosphine oxide

78-79-5

isoprene

707-61-9

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

Conditions
ConditionsYield
at 20℃; for 504000h;79%
for 168h; Ambient temperature;56%
17154-12-0

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

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

823-14-3

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

707-61-9

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

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

Dichlorophenylphosphine

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
30540-42-2

3-methyl-1-phenylphosphole

A

7564-51-4

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

B

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;
695-60-3

1-methoxy-3-methyl-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
104629-24-5

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

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
78-79-5

isoprene

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
563-46-2

2-Methyl-1-butene

644-97-3

Dichlorophenylphosphine

707-61-9

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

Conditions
ConditionsYield
With water

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

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

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

707-61-9

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

Conditions
ConditionsYield
With water
17786-49-1

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

707-61-9

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

Conditions
ConditionsYield
With water In chloroform at 0℃; for 0.5h;
707-61-9

3-Methyl-1-phenyl-2-phospholene 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+)

707-61-9

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

A

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

B

1353778-65-0

CF3O3S(1-)*C16H20N2P(1+)

Conditions
ConditionsYield
In dichloromethane at 20℃; for 20h; Inert atmosphere;A 100%
B 100%
707-61-9

3-Methyl-1-phenyl-2-phospholene 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%
13292-87-0

dimethylsulfide borane complex

707-61-9

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

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%
707-61-9

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

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℃;
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

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%
107-21-1

ethylene glycol

707-61-9

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

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

Conditions
ConditionsYield
With bromine In chloroform at 20℃; for 48h;88%
707-61-9

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

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

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 16h; Heating;84%
707-61-9

3-Methyl-1-phenyl-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%
762-42-5

dimethyl acetylenedicarboxylate

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

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 12h; Heating;79%
707-61-9

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

142-45-0

Acetylenedicarboxylic acid

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%
707-61-9

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

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%
110-65-6

1,4-dihydroxybut-2-yne

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

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 75h; Heating;68%
707-61-9

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)
707-61-9

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

111-46-6

diethylene glycol

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%
707-61-9

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

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

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

1,4-epoxy-1,4-dihydronaphthalene

707-61-9

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

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%
707-61-9

3-Methyl-1-phenyl-2-phospholene 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
917-92-0

2,2-dimethyl-3-butyne

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-(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%
707-61-9

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

74-88-4

methyl iodide

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%
922-67-8

propynoic acid methyl ester

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-(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%
707-61-9

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

74-88-4

methyl iodide

A

848484-65-1

3-ethyl-1-phenyl-2-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%
67-56-1

methanol

707-61-9

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

(+/-)-threo-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,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
707-61-9

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

(+/-)-threo 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;
707-61-9

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%
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    707-61-9 1H-Phosphole,2,3-dihydro-4-methyl-1-phenyl-, 1-oxide

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    3-Methyl-1-phenyl-4,5-dihydro-1H-phosphole 1-oxide

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    3-Methyl-1-phe3-Methyl-1-phenyl-2-phospholene 1-oxide, 94%

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    3-METHYL-1-PHENYL-2-PHOSPHOLENE 1-OXIDE Basic information Product Name: 3-METHYL-1-PHENYL-2-PHOSPHOLENE 1-OXIDE Synonyms: 1H-Phosphole, 2,3-dihydro-4-methyl-1-phenyl-, 1-oxide;1H-Phospho

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    1H-Phosphole,2,3-dihydro-4-methyl-1-phenyl-, 1-oxide 707-61-9

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Chemistry

Molecular Structure of 3-Methyl-1-phenyl-2-phospholene 1-oxide (707-61-9):

EINECS: 211-901-5
IUPAC Name: 3-Methyl-1-phenyl-1λ5-phosphacyclopent-2-ene 1-oxide  
Molecular Formula: C11H13OP
Molecular Weight: 192.194081 g/mol
XLogP3-AA: 1.3
H-Bond Donor: 0
H-Bond Acceptor: 1
Canonical SMILES: CC1=CP(=O)(CC1)C2=CC=CC=C2
InChI: InChI=1S/C11H13OP/c1-10-7-8-13(12,9-10)11-5-3-2-4-6-11/h2-6,9H,7-8H2,1H3
InChIKey: YMKWWHFRGALXLE-UHFFFAOYSA-N
Index of Refraction: 1.541
Molar Refractivity: 54.28 cm3
Molar Volume: 172.6 cm3
Surface Tension: 38.3 dyne/cm
Density: 1.11 g/cm3
Flash Point: 176.5 °C
Enthalpy of Vaporization: 59.06 kJ/mol
Boiling Point: 368.2 °C at 760 mmHg
Vapour Pressure: 2.75E-05 mmHg at 25 °C
Melting Point: 58-62 °C
Water Solubility: mg/L at 25 °C
Refractive Index: n20/D 1.5707(lit.)
Sensitive: Hygroscopic
BRN: 0609223

Toxicity Data With Reference

1.    

ipr-mus LD50:840 mg/kg

    DANKAS    Doklady Akademii Nauk S.S.S.R. 160 (1965),826.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Safety Information of 3-Methyl-1-phenyl-2-phospholene 1-oxide (707-61-9):
Hazard Codes: Xn
Risk Statements: 20/21/22-36/37/38-40
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
40: Limited evidence of a carcinogenic effect
Safety Statements: 26-28-36/37/39-45
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
28: After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
WGK Germany: 3
RTECS: SZ6105100
Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic vapors of POx.

Specification

  3-Methyl-1-phenyl-2-phospholene 1-oxide (707-61-9) is also known as 2,3-Dihydro-4-methyl-1-phenyl-1H-phosphole, 1-oxide ; 2-Phospholene, 3-methyl-1-phenyl-, 1-oxide ; NSC 107634 ; 1H-Phosphole, 2,3-dihydro-4-methyl-1-phenyl-, 1-oxide ; 2,3-Dihydro-4-methyl-1-phenyl-1H-phosphole 1-oxide with appearance of white to yellow crystals. It is incompatible with strong oxidizing agents. When heated to decomposition, it yields Carbon monoxide , oxides of phosphorus , Carbon dioxide .