4,5-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide supplier

Name
3-METHYL-1-PHENYL-2-PHOSPHOLENE 1-OXIDE
EINECS 211-901-5
CAS No. 707-61-9
Article Data22
CAS DataBase
Density 1.11 g/cm³
Solubility
Melting Point 58-62ºC
Formula C11H13 O P
Boiling Point 150 ºC.15 mm Hg(lit.)
Molecular Weight 192.197
Flash Point 113 ºC
Transport Information
Appearance
Safety Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic vapors of PO_x.
Risk Codes R20/21/22;R36/37/38;R40
Molecular Structure
Hazard Symbols
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;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With water at 26℃; for 24h;	71%
With water In chloroform	64 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

Conditions	Yield
In tetrahydrofuran at 20℃; for 6h;	60%

: 644-97-3
Dichlorophenylphosphine

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

Conditions

Conditions	Yield
	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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With water

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

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

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In dichloromethane at 20℃; for 20h; Inert atmosphere;	A 100% B 100%

...Expand

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

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

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In 1,2-dimethoxyethane for 36h; Heating;	A 55% B 21%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
In 1,2-dimethoxyethane for 12h; Heating;	A 49% B 37%

...Expand

: 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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
With bromine In chloroform at 20℃; for 72h;	A 47% B 45% C n/a D n/a

...Expand

: 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

Conditions	Yield
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

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

4,5-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide Chemical Properties

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

4,5-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide Toxicity Data With Reference

ipr-mus LD50:840 mg/kg

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

4,5-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide Consensus Reports

Reported in EPA TSCA Inventory.

4,5-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide 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 PO_x.

4,5-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide 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 .

Product Name

3-METHYL-1-PHENYL-2-PHOSPHOLENE 1-OXIDE

Synthetic route

4,5-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide Chemical Properties

4,5-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide Toxicity Data With Reference

4,5-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide Consensus Reports

4,5-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide Safety Profile

4,5-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide Specification

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