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Methyltriphenylphosphonium bromide is an organophosphorus compound, characterized by its white powder appearance. It is a lipophilic molecule with a cation, which allows it to be used for delivering molecules to specific cell components. This property, along with its potential as an antineoplastic agent, makes it a versatile compound in various applications.

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  • (2S,4R)-N-[(1S,2R)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)-2-oxanyl]propyl]-1-methyl-4-propyl-2-pyrrolidinecarboxamide hydrochloride

    Cas No: 1779-49-3

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  • 1779-49-3 Structure
  • Basic information

    1. Product Name: Methyltriphenylphosphonium bromide
    2. Synonyms: TRIPHENYLMETHYLPHOSPHONIUM BROMIDE;METHYLTRIPHENYLPHOSPHONIUM BROMIDE;Bromo(methyl)triphenylphosphorane;methyltriphenyl-phosphoniubromide;Phosphonium, methyltriphenyl-, bromide;Phosphonium,methyltriphenyl-,bromide;MethyltriphenylphosphoniumBromide>98%;METHYL TRIPHENYL PHOSPHONIUM BROMIDE LOW WATER
    3. CAS NO:1779-49-3
    4. Molecular Formula: Br*C19H18P
    5. Molecular Weight: 357.22
    6. EINECS: 217-218-9
    7. Product Categories: Phosphonium Compounds;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;Wittig Reaction;C-C Bond Formation;Olefination;Wittig Reagents;organophosphorus compound
    8. Mol File: 1779-49-3.mol
  • Chemical Properties

    1. Melting Point: 230-234 °C(lit.)
    2. Boiling Point: N/A
    3. Flash Point: >240°C
    4. Appearance: White/Powder
    5. Density: N/A
    6. Vapor Pressure: 0.0000002 hPa
    7. Refractive Index: N/A
    8. Storage Temp.: 2-8°C
    9. Solubility: H2O: 0.1 g/mL, clear
    10. Water Solubility: 400 g/L (25 ºC)
    11. Sensitive: Hygroscopic
    12. BRN: 3599467
    13. CAS DataBase Reference: Methyltriphenylphosphonium bromide(CAS DataBase Reference)
    14. NIST Chemistry Reference: Methyltriphenylphosphonium bromide(1779-49-3)
    15. EPA Substance Registry System: Methyltriphenylphosphonium bromide(1779-49-3)
  • Safety Data

    1. Hazard Codes: Xn,Xi
    2. Statements: 20/21/22-36/37/38
    3. Safety Statements: 36/37-36-26
    4. RIDADR: UN 1390 4.3/PG 2
    5. WGK Germany: 3
    6. RTECS:
    7. TSCA: T
    8. HazardClass: 6.1
    9. PackingGroup: III
    10. Hazardous Substances Data: 1779-49-3(Hazardous Substances Data)

1779-49-3 Usage

Uses

Used in Pharmaceutical Industry:
Methyltriphenylphosphonium bromide is used as a PTC (Phase Transfer Catalyst) for facilitating chemical reactions in both aqueous and non-aqueous phases, which is crucial in the synthesis of various pharmaceutical compounds.
Used in Organic Synthesis:
Methyltriphenylphosphonium bromide is used as a reagent in the Wittig reaction for methylenation, a key step in the synthesis of complex organic molecules such as enynes and 9-isopropenyl-phenanthrenes. Its lipophilic nature aids in delivering molecules to specific cell components, making it a valuable tool in organic synthesis.
Used in Antineoplastic Applications:
Methyltriphenylphosphonium bromide is used as an antineoplastic agent, potentially contributing to the development of novel cancer treatments by targeting and delivering therapeutic molecules to cancer cells.
Used in Calibration of Melting Point Instruments:
Methyltriphenylphosphonium bromide serves as a calibration substance (ME 30130598) for the regular calibration of Mettler-Toledo melting point instruments, ensuring accurate and reliable measurements in various scientific and industrial applications.

Purification Methods

If the solid is sticky, wash it with *C6H6 and dry it in a vacuum over P2O5. [Marvel & Gall J Org Chem 24 1494 1959, Chem Ber 87 1318 1954, Milas & Priesing J Am Chem Soc 79 6295 1957, Wittig & Sch.llkopf Org Synth 40 66 1960.] The iodide, on recrystallisation from H2O, has m 187.5-188.5o [Mann et al. J Chem Soc 1130 1953, Wittig & Geissler Justus Liebigs Ann Chem 580 44 1953]. [Beilstein 16 IV 981.]

Check Digit Verification of cas no

The CAS Registry Mumber 1779-49-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,7,7 and 9 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1779-49:
(6*1)+(5*7)+(4*7)+(3*9)+(2*4)+(1*9)=113
113 % 10 = 3
So 1779-49-3 is a valid CAS Registry Number.
InChI:InChI=1/C18H15P.CH3Br/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-2/h1-15H;1H3/p+1

1779-49-3 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (M0779)  Methyltriphenylphosphonium Bromide  >98.0%(HPLC)(T)

  • 1779-49-3

  • 25g

  • 205.00CNY

  • Detail
  • TCI America

  • (M0779)  Methyltriphenylphosphonium Bromide  >98.0%(HPLC)(T)

  • 1779-49-3

  • 100g

  • 490.00CNY

  • Detail
  • TCI America

  • (M0779)  Methyltriphenylphosphonium Bromide  >98.0%(HPLC)(T)

  • 1779-49-3

  • 500g

  • 1,700.00CNY

  • Detail
  • Alfa Aesar

  • (A15878)  Methyltriphenylphosphonium bromide, 98+%   

  • 1779-49-3

  • 50g

  • 185.0CNY

  • Detail
  • Alfa Aesar

  • (A15878)  Methyltriphenylphosphonium bromide, 98+%   

  • 1779-49-3

  • 250g

  • 612.0CNY

  • Detail
  • Alfa Aesar

  • (A15878)  Methyltriphenylphosphonium bromide, 98+%   

  • 1779-49-3

  • 1000g

  • 2405.0CNY

  • Detail
  • Sigma-Aldrich

  • (94993)  Mettler-Toledo Calibration substance ME 30130598, Methyltriphenylphosphoniumbromide  tracable to primary standards (LGC)

  • 1779-49-3

  • 94993-5G

  • 1,207.44CNY

  • Detail
  • Aldrich

  • (130079)  Methyltriphenylphosphoniumbromide  98%

  • 1779-49-3

  • 130079-25G

  • 184.86CNY

  • Detail
  • Aldrich

  • (130079)  Methyltriphenylphosphoniumbromide  98%

  • 1779-49-3

  • 130079-100G

  • 555.75CNY

  • Detail
  • Aldrich

  • (130079)  Methyltriphenylphosphoniumbromide  98%

  • 1779-49-3

  • 130079-500G

  • 1,806.48CNY

  • Detail

1779-49-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyltriphenylphosphonium bromide

1.2 Other means of identification

Product number -
Other names Methyltriphenylphosphanium bromide

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:1779-49-3 SDS

1779-49-3Synthetic route

benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

triphenylphosphine hydrobromide
6399-81-1

triphenylphosphine hydrobromide

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Conditions
ConditionsYield
100%
methanol
67-56-1

methanol

triphenylphosphine
603-35-0

triphenylphosphine

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Conditions
ConditionsYield
With hydrogen bromide at 110℃; for 8h;99.2%
With hydrogen bromide at 110℃; for 15h;97%
With hydrogen bromide In water at 120℃; for 22.5h;97%
methyl bromide
74-83-9

methyl bromide

triphenylphosphine
603-35-0

triphenylphosphine

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Conditions
ConditionsYield
In benzene at 20℃; for 4h;99%
In benzene for 48h; Ambient temperature;95%
In acetonitrile
methyl bromide
74-83-9

methyl bromide

diphenylphosphane
829-85-6

diphenylphosphane

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Conditions
ConditionsYield
In benzene99%
triphenylphosphine hydrobromide
6399-81-1

triphenylphosphine hydrobromide

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Conditions
ConditionsYield
at 75℃; for 0.75h; Inert atmosphere; neat (no solvent);99%
at 70℃;70%
methyl N-acetyl-α-triphenylphosphoniumglycinate bromide
1314805-21-4

methyl N-acetyl-α-triphenylphosphoniumglycinate bromide

A

(N-Acetylamino)methyltriphenylphosphonium bromide
1314805-28-1

(N-Acetylamino)methyltriphenylphosphonium bromide

B

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Conditions
ConditionsYield
Stage #1: methyl N-acetyl-α-triphenylphosphoniumglycinate bromide at 25℃; under 1 - 2 Torr; for 1h;
Stage #2: With triphenylphosphine hydrobromide; triphenylphosphine at 100 - 115℃; for 1h;
A 98.6%
B 87%
triphenylphosphine
603-35-0

triphenylphosphine

trimethyl orthoformate
149-73-5

trimethyl orthoformate

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Conditions
ConditionsYield
With ammonium bromide at 110℃; for 4h; Sealed tube;96%
With ammonium bromide at 110℃; for 12h;96%
With cis,trans-24-bromotetracos-12-enal ethylene acetal
methyl N-benzoyl-α-triphenylphosphonioglycinate bromide

methyl N-benzoyl-α-triphenylphosphonioglycinate bromide

A

C20H18N2O6
498572-96-6

C20H18N2O6

B

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

C

α-(N-benzoylamino)methyltriphenylphosphonium bromide
28387-29-3

α-(N-benzoylamino)methyltriphenylphosphonium bromide

Conditions
ConditionsYield
Stage #1: methyl N-benzoyl-α-triphenylphosphonioglycinate bromide at 25℃; under 1 - 2 Torr; for 1h;
Stage #2: With triphenylphosphine hydrobromide; triphenylphosphine at 110 - 120℃; for 1h;
A 6.2%
B 81%
C 89.1%
Br(1-)*C26H29NO3P(1+)
1314805-22-5

Br(1-)*C26H29NO3P(1+)

A

Br(1-)*C24H27NOP(1+)
1314805-30-5

Br(1-)*C24H27NOP(1+)

B

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Conditions
ConditionsYield
Stage #1: Br(1-)*C26H29NO3P(1+) at 25℃; under 1 - 2 Torr; for 1h;
Stage #2: With triphenylphosphine hydrobromide; triphenylphosphine at 120℃; for 1.5h;
A 78.7%
B 44.5%
Se-phenacyldimethylselenonium bromide
19320-74-2

Se-phenacyldimethylselenonium bromide

triphenylphosphine
603-35-0

triphenylphosphine

A

Triphenylphosphine selenide
3878-44-2

Triphenylphosphine selenide

B

2-(methylselanyl)-1-phenylethan-1-one
19859-29-1

2-(methylselanyl)-1-phenylethan-1-one

C

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

D

triphenylphenacylphosphonium bromide
6048-29-9

triphenylphenacylphosphonium bromide

Conditions
ConditionsYield
In benzene for 6h; Heating; Further byproducts given;A 7.3%
B n/a
C 13%
D 73%
Se-phenacyldimethylselenonium bromide
19320-74-2

Se-phenacyldimethylselenonium bromide

triphenylphosphine
603-35-0

triphenylphosphine

A

Triphenylphosphine selenide
3878-44-2

Triphenylphosphine selenide

B

2-(methylselanyl)-1-phenylethan-1-one
19859-29-1

2-(methylselanyl)-1-phenylethan-1-one

C

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

D

triphenylphenacylphosphonium bromide
6048-29-9

triphenylphenacylphosphonium bromide

E

acetophenone
98-86-2

acetophenone

Conditions
ConditionsYield
In benzene for 6h; Product distribution; Mechanism; Heating;A 7.3%
B n/a
C 13%
D 73%
E n/a
methyl N-benzoyl-α-triphenylphosphonioglycinate bromide

methyl N-benzoyl-α-triphenylphosphonioglycinate bromide

A

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

B

α-(N-benzoylamino)methyltriphenylphosphonium bromide
28387-29-3

α-(N-benzoylamino)methyltriphenylphosphonium bromide

Conditions
ConditionsYield
With triphenylphosphine hydrobromide; triphenylphosphine at 115℃; under 1 - 2 Torr; for 1.5h;A n/a
B 71.5%
Stage #1: methyl N-benzoyl-α-triphenylphosphonioglycinate bromide at 25℃; under 1 - 2 Torr; for 1h;
Stage #2: at 155℃; for 0.5h;
A 55.4%
B 27%
bromobenzene
108-86-1

bromobenzene

/PBFRI043-1235/

/PBFRI043-1235/

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Conditions
ConditionsYield
With oct-1-ene; nickel dibromide In tetrahydrofuran Heating;56%
methyl N-acetyl-α-triphenylphosphoniumglycinate bromide
1314805-21-4

methyl N-acetyl-α-triphenylphosphoniumglycinate bromide

A

C10H14N2O6

C10H14N2O6

B

(N-Acetylamino)methyltriphenylphosphonium bromide
1314805-28-1

(N-Acetylamino)methyltriphenylphosphonium bromide

C

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Conditions
ConditionsYield
Stage #1: methyl N-acetyl-α-triphenylphosphoniumglycinate bromide at 25℃; under 1 - 2 Torr; for 1h;
Stage #2: at 140 - 150℃; for 0.5h;
A 19.4%
B 49.5%
C 37.2%
Methylenetriphenylphosphorane
19493-09-5

Methylenetriphenylphosphorane

A

(chloromethyl)triphenylphosphonium bromide
111441-95-3

(chloromethyl)triphenylphosphonium bromide

B

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

C

Dichlormethyl-triphenyl-phosphonium-bromid
1826-86-4

Dichlormethyl-triphenyl-phosphonium-bromid

Conditions
ConditionsYield
With 1,1-difluorotetrachloroethane In diethyl ether at -78℃; for 0.5h;A 40%
B 35%
C 15%
Methylenetriphenylphosphorane
19493-09-5

Methylenetriphenylphosphorane

A

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

B

iodomethyl triphenylphosphonium bromide
98822-67-4

iodomethyl triphenylphosphonium bromide

C

Diiodomethyl-triphenyl-phosphonium; bromide
117747-27-0

Diiodomethyl-triphenyl-phosphonium; bromide

Conditions
ConditionsYield
With 1-chloro-1,1,2,2-tetrafluoro-2-iodo-ethane In diethyl ether at -78℃; for 0.5h;A 31%
B 40%
C 5 % Spectr.
Br(1-)*C26H29NO3P(1+)
1314805-22-5

Br(1-)*C26H29NO3P(1+)

A

C16H26N2O6
498572-95-5

C16H26N2O6

B

Br(1-)*C24H27NOP(1+)
1314805-30-5

Br(1-)*C24H27NOP(1+)

C

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Conditions
ConditionsYield
Stage #1: Br(1-)*C26H29NO3P(1+) at 25℃; under 1 - 2 Torr; for 1h;
Stage #2: at 120℃; for 0.5h;
A 22.9%
B 34.5%
C 21.8%
Methylenetriphenylphosphorane
19493-09-5

Methylenetriphenylphosphorane

A

(bromomethyl)triphenyl phosphonium bromide
1034-49-7

(bromomethyl)triphenyl phosphonium bromide

B

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

C

tribromomethyltriphenylphosphonium bromide
56506-89-9

tribromomethyltriphenylphosphonium bromide

D

(dibromomethyl)(triphenyl)phosphonium bromide
56506-90-2

(dibromomethyl)(triphenyl)phosphonium bromide

Conditions
ConditionsYield
With 1,2-dibromo-1,1,2,2-tetrafluoroethane In diethyl ether at -78℃; for 0.5h;A 18%
B 35 % Spectr.
C 24 % Spectr.
D 13 % Spectr.
5-bromo-4-methoxy-3-phenylfuran-2(5H)-one
100074-67-7

5-bromo-4-methoxy-3-phenylfuran-2(5H)-one

triphenylphosphine
603-35-0

triphenylphosphine

A

methyl bromide
74-83-9

methyl bromide

B

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

C

2,5-dihydro-2-oxo-3-phenyl-5-triphenylphosphoniumfuran-4-olate
100074-79-1

2,5-dihydro-2-oxo-3-phenyl-5-triphenylphosphoniumfuran-4-olate

Conditions
ConditionsYield
In benzene for 2h; Product distribution; Mechanism; Heating;A n/a
B 8%
C 65.3 g
In benzene for 2h; Heating;A n/a
B 8%
C 65.3 g
(2-Isobutyryl-vinyl)-triphenylphosphoniumbromid

(2-Isobutyryl-vinyl)-triphenylphosphoniumbromid

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Conditions
ConditionsYield
In methanol
triphenylphosphine hydrobromide
6399-81-1

triphenylphosphine hydrobromide

methoxybenzene
100-66-3

methoxybenzene

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Conditions
ConditionsYield
at 160 - 170℃;
4-bromo-1,1-dimethoxypentane
89940-00-1

4-bromo-1,1-dimethoxypentane

triphenylphosphine
603-35-0

triphenylphosphine

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

2-methyl-1,2-epoxypropane
558-30-5

2-methyl-1,2-epoxypropane

triphenylphosphine
603-35-0

triphenylphosphine

A

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

B

(2-Methyl-propenyl)-triphenyl-phosphonium; bromide
53101-88-5

(2-Methyl-propenyl)-triphenyl-phosphonium; bromide

Conditions
ConditionsYield
With hydrogen bromide; phenol 1.) 100 deg C, 24 h; Yield given. Multistep reaction. Yields of byproduct given;
epoxy-1,2 propyl-2 pentane
98560-25-9

epoxy-1,2 propyl-2 pentane

triphenylphosphine
603-35-0

triphenylphosphine

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Conditions
ConditionsYield
With hydrogen bromide; phenol 1.) 100 deg C, 24 h; Yield given. Multistep reaction;
cis-24-bromotetracos-12-enal ethylene acetal
84451-53-6

cis-24-bromotetracos-12-enal ethylene acetal

triphenylphosphine
603-35-0

triphenylphosphine

A

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

B

cis-23-(dioxolan-2-yl)tricos-12-enyltriphenylphosphonium bromide
113309-15-2

cis-23-(dioxolan-2-yl)tricos-12-enyltriphenylphosphonium bromide

Conditions
ConditionsYield
With trimethyl orthoformate
cis-24-bromotetracos-12-enal ethylene acetal
113309-14-1

cis-24-bromotetracos-12-enal ethylene acetal

triphenylphosphine
603-35-0

triphenylphosphine

A

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

B

trans-23-(dioxolan-2-yl)tricos-12-enyltriphenylphosphonium bromide
113309-16-3

trans-23-(dioxolan-2-yl)tricos-12-enyltriphenylphosphonium bromide

Conditions
ConditionsYield
With trimethyl orthoformate
triphenylphosphine
603-35-0

triphenylphosphine

methyloxirane
75-56-9, 16033-71-9

methyloxirane

A

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

B

(2-hydroxypropyl)triphenylphosphonium bromide
3020-30-2

(2-hydroxypropyl)triphenylphosphonium bromide

C

(E)-prop-1-en-1-yl-triphenylphosphonium bromide
28691-76-1

(E)-prop-1-en-1-yl-triphenylphosphonium bromide

Conditions
ConditionsYield
Product distribution; multistep reaction; variation of temperature and reaction time;
With hydrogen bromide; phenol 1.) 100 deg C, 24 h; Yield given. Multistep reaction. Yields of byproduct given;
triphenylphosphine
603-35-0

triphenylphosphine

1,2-Epoxyoctane
2984-50-1

1,2-Epoxyoctane

A

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

B

((E)-Oct-1-enyl)-triphenyl-phosphonium; bromide

((E)-Oct-1-enyl)-triphenyl-phosphonium; bromide

C

((E)-Oct-2-enyl)-triphenyl-phosphonium; bromide
56318-76-4, 88518-02-9

((E)-Oct-2-enyl)-triphenyl-phosphonium; bromide

Conditions
ConditionsYield
With hydrogen bromide; phenol 1.) 100 deg C, 24 h; Yield given. Multistep reaction. Yields of byproduct given;
benzophenone
119-61-9

benzophenone

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran
Stage #2: benzophenone In tetrahydrofuran at 20℃; for 6h; Wittig reaction;
100%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #2: benzophenone In tetrahydrofuran at 20℃; Inert atmosphere;
94%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In diethyl ether at 20℃; for 0.25h; Inert atmosphere;
Stage #2: benzophenone In diethyl ether at 0℃; for 15h; Inert atmosphere;
87%
benzyl 4-oxo-1-piperidinecarboxylate
19099-93-5

benzyl 4-oxo-1-piperidinecarboxylate

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

benzyl 4-methylene-1-piperidinecarboxylate
138163-12-9

benzyl 4-methylene-1-piperidinecarboxylate

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 1h;
Stage #2: benzyl 4-oxo-1-piperidinecarboxylate In tetrahydrofuran at 0 - 20℃;
100%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 2h; Wittig Reaction; Inert atmosphere;
Stage #2: benzyl 4-oxo-1-piperidinecarboxylate In tetrahydrofuran at 0 - 20℃; for 4h; Wittig Reaction; Inert atmosphere;
92%
Stage #1: Methyltriphenylphosphonium bromide With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h;
Stage #2: benzyl 4-oxo-1-piperidinecarboxylate In tetrahydrofuran for 2h;
81%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

(1R,4aS,8aS)-(-)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-1-naphthaleneacetonitrile
91547-83-0

(1R,4aS,8aS)-(-)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-1-naphthaleneacetonitrile

(1S,4aS,8aS)-(+)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetonitrile
124462-80-2

(1S,4aS,8aS)-(+)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetonitrile

Conditions
ConditionsYield
With sodium amide In tetrahydrofuran at 20℃; for 3.5h; Wittig reaction;100%
With n-butyllithium 1. DME, n-hexane, 0 deg C, 1.5 h 2. DME, 2 h, room temperature; Yield given. Multistep reaction;
With sodium hydride 1.) DMSO, 15 min, 2.) DMSO, 75 deg C, 5 h; Yield given. Multistep reaction;
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

Methylenetriphenylphosphorane
19493-09-5

Methylenetriphenylphosphorane

Conditions
ConditionsYield
With ammonia; sodium amide100%
With sodium hexamethyldisilazane In diethyl ether Glovebox; Inert atmosphere;98%
With phenyllithium In dibutyl ether at 0 - 20℃; for 3.5h; Inert atmosphere; Glovebox; Schlenk technique;87%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

diphenyl(methyl)phosphine oxide
2129-89-7

diphenyl(methyl)phosphine oxide

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With water for 0.5h; Reflux;
Stage #2: With sodium hydroxide for 2h; Reflux;
100%
With sodium hydroxide for 1h; Heating;95%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

salicylaldehyde
90-02-8

salicylaldehyde

2-allylphenol
695-84-1

2-allylphenol

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h; Wittig Olefination;
Stage #2: salicylaldehyde In tetrahydrofuran at -78 - 30℃; Wittig Olefination;
100%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h;
Stage #2: salicylaldehyde In tetrahydrofuran at -78 - 20℃;
100%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 23℃; for 2h;
Stage #2: salicylaldehyde In tetrahydrofuran at -78 - 23℃; for 20h;
98%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-bromostyrene
2039-88-5

2-bromostyrene

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h; Wittig Olefination;
Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran at 0 - 20℃; for 12h; Wittig Olefination;
100%
With n-butyllithium In tetrahydrofuran99%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In diethyl ether at 20℃; for 0.25h; Inert atmosphere;
Stage #2: ortho-bromobenzaldehyde In diethyl ether at 0℃; for 15h; Inert atmosphere;
93%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

1-naphthaldehyde
66-77-3

1-naphthaldehyde

1-vinylnaphthalene
826-74-4

1-vinylnaphthalene

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In toluene at 0 - 20℃; for 4.5h;
Stage #2: 1-naphthaldehyde In toluene at 0 - 20℃;
100%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In toluene at 0 - 20℃; for 4.5h;
Stage #2: 1-naphthaldehyde In toluene at 0 - 20℃;
100%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In toluene at 0 - 20℃; for 4.5h;
Stage #2: 1-naphthaldehyde In toluene at 0 - 20℃;
100%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

(E)-1-Phenyl-1,3-butadiene
16939-57-4

(E)-1-Phenyl-1,3-butadiene

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: (E)-3-phenylpropenal In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;
100%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; cyclohexane at 0℃; for 0.25h;
Stage #2: (E)-3-phenylpropenal In tetrahydrofuran; cyclohexane at 0 - 20℃; for 2h; Wittig olefination;
96%
Stage #1: Methyltriphenylphosphonium bromide In tetrahydrofuran; hexane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: (E)-3-phenylpropenal In tetrahydrofuran; hexane at 0 - 20℃; for 10h; Inert atmosphere;
96%
cyclohexanedione monoethylene ketal
4746-97-8

cyclohexanedione monoethylene ketal

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

8-methylene-1,4-dioxaspiro[4.5]decane
51656-90-7

8-methylene-1,4-dioxaspiro[4.5]decane

Conditions
ConditionsYield
With potassium tert-butylate In benzene at 25℃; for 1h;100%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.666667h;
Stage #2: cyclohexanedione monoethylene ketal In tetrahydrofuran; hexane at 20℃;
92%
With sodium hydride In dimethyl sulfoxide90%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

4-chloronicotinaldehyde
114077-82-6

4-chloronicotinaldehyde

4-chloro-3-vinylpyridine
223573-95-3

4-chloro-3-vinylpyridine

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran100%
With tert.-butyl lithium In diethyl ether; pentane at -78 - 20℃; Wittig Olefination; Inert atmosphere;50%
With n-butyllithium In tetrahydrofuran
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

(+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal
289666-94-0

(+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal

(+)-(4S,5R,6R,7R)-6-benzyloxy-8-tert-butyldiphenylsilyloxy-3,3-dimethyl-4-methoxy-5,7-methylenedioxyoctyl-1-ene
289667-02-3

(+)-(4S,5R,6R,7R)-6-benzyloxy-8-tert-butyldiphenylsilyloxy-3,3-dimethyl-4-methoxy-5,7-methylenedioxyoctyl-1-ene

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 65℃; for 0.25h;
Stage #2: (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal In tetrahydrofuran; hexane at 0℃; for 0.333333h; Wittig reaction;
100%
With n-butyllithium at 0 - 20℃; Wittig reaction;100%
4,15-diformyl[2.2]paracyclophane
288156-11-6

4,15-diformyl[2.2]paracyclophane

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

pseudo-gem-divinyl<2.2>paracyclophane
111870-60-1

pseudo-gem-divinyl<2.2>paracyclophane

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; Wittig reaction; Inert atmosphere;
Stage #2: 4,15-diformyl[2.2]paracyclophane In tetrahydrofuran Wittig reaction; Inert atmosphere; Cooling with ice;
100%
With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 18h; Wittig reaction;85%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

1-O-Benzyl-2-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-3-O-[(3R,7R,11S,15S)-15-formyl-3,7,11,15-tetramethylpentadecanyl]-sn-glycerol
307949-94-6

1-O-Benzyl-2-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-3-O-[(3R,7R,11S,15S)-15-formyl-3,7,11,15-tetramethylpentadecanyl]-sn-glycerol

1-O-Benzyl-2-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-3-O-[(3R,7R,11S,15S)-3,7,11,15-tetramethylheptadec-16-enyl]-sn-glycerol
307949-95-7

1-O-Benzyl-2-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-3-O-[(3R,7R,11S,15S)-3,7,11,15-tetramethylheptadec-16-enyl]-sn-glycerol

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In hexane at -78 - 20℃; for 0.666667h; Dehydrobromination;
Stage #2: 1-O-Benzyl-2-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-3-O-[(3R,7R,11S,15S)-15-formyl-3,7,11,15-tetramethylpentadecanyl]-sn-glycerol In tetrahydrofuran; hexane at -78 - -25℃; for 1.25h; Condensation; Wittig reaction; Further stages.;
100%
4-isopropyl-5-oxo-hexanenitrile
34041-01-5

4-isopropyl-5-oxo-hexanenitrile

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

4-isopropyl-5-methyl-hex-5-enenitrile
365978-53-6

4-isopropyl-5-methyl-hex-5-enenitrile

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In dimethyl sulfoxide at 25℃;
Stage #2: 4-isopropyl-5-oxo-hexanenitrile In dimethyl sulfoxide for 1h;
100%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

((R)-3,4-Dihydroxy-2,2,3-trimethyl-cyclopentyl)-acetaldehyde

((R)-3,4-Dihydroxy-2,2,3-trimethyl-cyclopentyl)-acetaldehyde

(S)-4-Allyl-1,5,5-trimethyl-cyclopentane-1,2-diol
383196-60-9

(S)-4-Allyl-1,5,5-trimethyl-cyclopentane-1,2-diol

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran for 0.5h; Wittig olefination;100%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

(6R)-(t-butyldimethylsilanyloxymethyl)-(2R)-ethynyl-(3R)-(triisopropylsilanyloxy)-tetrahydropyran-4-one
310398-06-2

(6R)-(t-butyldimethylsilanyloxymethyl)-(2R)-ethynyl-(3R)-(triisopropylsilanyloxy)-tetrahydropyran-4-one

(6R)-(t-butyldimethylsilanyloxymethyl)-(2R)-ethynyl-4-methylene-(3S)-(triisopropylsilanoxy)-tetrahydropyran
310398-07-3

(6R)-(t-butyldimethylsilanyloxymethyl)-(2R)-ethynyl-4-methylene-(3S)-(triisopropylsilanoxy)-tetrahydropyran

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1.5h;
Stage #2: (6R)-(t-butyldimethylsilanyloxymethyl)-(2R)-ethynyl-(3R)-(triisopropylsilanyloxy)-tetrahydropyran-4-one In tetrahydrofuran; hexane at 20℃; for 2.5h; Further stages.;
100%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

C13H18O

C13H18O

C14H20

C14H20

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide for 72h;100%
1H-indol-2-ylcarboxaldehyde
19005-93-7

1H-indol-2-ylcarboxaldehyde

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

2-vinyl-1H-indole
53654-35-6

2-vinyl-1H-indole

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium hexamethylsilazane In tetrahydrofuran; toluene at 20℃; for 0.5h;
Stage #2: 1H-indol-2-ylcarboxaldehyde In tetrahydrofuran; toluene at 20℃; for 2h; Wittig reaction;
100%
Stage #1: Methyltriphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #2: 1H-indol-2-ylcarboxaldehyde In tetrahydrofuran at 20℃; for 14h; Inert atmosphere;
92%
With potassium hexamethylsilazane In tetrahydrofuran; toluene at 23℃; for 3h;90%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

2-isopropoxybiphenyl-3-carbaldehyde
478942-83-5

2-isopropoxybiphenyl-3-carbaldehyde

2-isopropoxy-3-vinyl-1,1'-biphenyl
478942-85-7

2-isopropoxy-3-vinyl-1,1'-biphenyl

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 22℃; for 2h;
Stage #2: 2-isopropoxybiphenyl-3-carbaldehyde In tetrahydrofuran at -78 - 22℃; Wittig olefination;
100%
Stage #1: Methyltriphenylphosphonium bromide With sodium t-butanolate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #2: 2-isopropoxybiphenyl-3-carbaldehyde In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
99%
With potassium tert-butylate In diethyl ether at 0℃; Wittig olefination;88%
Stage #1: Methyltriphenylphosphonium bromide With sodium t-butanolate In diethyl ether at 20℃; for 0.5h; Wittig Olefination; Inert atmosphere;
Stage #2: 2-isopropoxybiphenyl-3-carbaldehyde In diethyl ether at 20℃; for 0.5h; Wittig Olefination; Inert atmosphere;
55%
With potassium tert-butylate In diethyl ether at 0℃; for 0.166667h; Wittig reaction;
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

3-formyl-1H-indole-2-carboxylic acid (but-3-enyl)amide
519033-40-0

3-formyl-1H-indole-2-carboxylic acid (but-3-enyl)amide

3-vinyl-1H-indole-2-carboxylic acid (but-3-enyl)amide
519033-41-1

3-vinyl-1H-indole-2-carboxylic acid (but-3-enyl)amide

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 3h;
Stage #2: 3-formyl-1H-indole-2-carboxylic acid (but-3-enyl)amide In tetrahydrofuran; hexane at 20℃; for 2h;
100%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one
481656-25-1

(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one

(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-5-(methylene)decahydronaphthalene
481656-15-9

(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-5-(methylene)decahydronaphthalene

Conditions
ConditionsYield
With potassium tert-butylate In benzene Heating;100%
With potassium tert-butylate In benzene for 12h; Wittig reaction; Heating;100%
With potassium tert-butylate In benzene for 12h; Wittig reaction; heating;100%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In benzene for 2h; Wittig methylenation; Inert atmosphere; Reflux;
Stage #2: (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one In benzene for 12h; Wittig methylenation; Inert atmosphere; Reflux;
100%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

C91H108O17

C91H108O17

C92H110O16

C92H110O16

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide; C91H108O17 With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h; Wittig reaction;
Stage #2: Methyltriphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5h; Wittig reaction; Further stages.;
100%
Stage #1: Methyltriphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.333333h;
Stage #2: C91H108O17 In tetrahydrofuran at 0℃; for 0.5h;
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

2-isopropoxy-4-methoxybenzene-1-carboaldehyde
107811-48-3

2-isopropoxy-4-methoxybenzene-1-carboaldehyde

1-methoxy-5-isopropoxy-4-vinylbenzene

1-methoxy-5-isopropoxy-4-vinylbenzene

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 22℃; for 2h;
Stage #2: 2-isopropoxy-4-methoxybenzene-1-carboaldehyde In tetrahydrofuran at -78 - 22℃; Wittig olefination;
100%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

2-isopropoxy-5-methoxybenzaldehyde

2-isopropoxy-5-methoxybenzaldehyde

2-isopropoxy-5-methoxy-1-vinylbenzene
623902-72-7

2-isopropoxy-5-methoxy-1-vinylbenzene

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 22℃; for 2h;
Stage #2: 2-isopropoxy-5-methoxybenzaldehyde In tetrahydrofuran at -78 - 22℃; Wittig olefination;
100%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

(3aR,5R,6S,8aR,9R,9aS)-5-Hydroxy-5-isopropenyl-9-isopropyl-2,2,6,8a-tetramethyl-3a,5,6,7,8,8a,9,9a-octahydro-1,3-dioxa-cyclopenta[a]azulene-6-carbaldehyde

(3aR,5R,6S,8aR,9R,9aS)-5-Hydroxy-5-isopropenyl-9-isopropyl-2,2,6,8a-tetramethyl-3a,5,6,7,8,8a,9,9a-octahydro-1,3-dioxa-cyclopenta[a]azulene-6-carbaldehyde

(3aR,5R,6R,8aR,9R,9aS)-5-Isopropenyl-9-isopropyl-2,2,6,8a-tetramethyl-6-vinyl-3a,5,6,7,8,8a,9,9a-octahydro-1,3-dioxa-cyclopenta[a]azulen-5-ol

(3aR,5R,6R,8aR,9R,9aS)-5-Isopropenyl-9-isopropyl-2,2,6,8a-tetramethyl-6-vinyl-3a,5,6,7,8,8a,9,9a-octahydro-1,3-dioxa-cyclopenta[a]azulen-5-ol

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran Wittig reaction;100%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

(3aS,4S,7aR)-4-Benzyloxymethyl-2,3,3a,4,5,7a-hexahydro-benzofuran-2-ol

(3aS,4S,7aR)-4-Benzyloxymethyl-2,3,3a,4,5,7a-hexahydro-benzofuran-2-ol

(1R,5S,6S)-5-benzyloxymethyl-6-(2-propenyl)-2-cyclohex-1-ol
654680-31-6

(1R,5S,6S)-5-benzyloxymethyl-6-(2-propenyl)-2-cyclohex-1-ol

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran for 0.25h;
Stage #2: (3aS,4S,7aR)-4-Benzyloxymethyl-2,3,3a,4,5,7a-hexahydro-benzofuran-2-ol In tetrahydrofuran at -78℃; for 0.333333h; Wittig reaction;
Stage #3: In tetrahydrofuran for 2h; Wittig reaction; Heating;
100%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

(E)-3-[(Z)-(2R,8S,9R)-8-(tert-Butyl-diphenyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-2-methyl-propenal
749924-32-1

(E)-3-[(Z)-(2R,8S,9R)-8-(tert-Butyl-diphenyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-2-methyl-propenal

(Z)-(2R,3S,9R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-9-((E)-2-methyl-buta-1,3-dienyl)-2,3,4,7,8,9-hexahydro-oxonine
749924-33-2

(Z)-(2R,3S,9R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-9-((E)-2-methyl-buta-1,3-dienyl)-2,3,4,7,8,9-hexahydro-oxonine

Conditions
ConditionsYield
With n-butyllithium at -78℃; for 2h; Wittig methylenation;100%
2,2'-diformyl-5,5',6,6'-tetramethoxybiphenyl
31477-10-8

2,2'-diformyl-5,5',6,6'-tetramethoxybiphenyl

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

2,2'-divinyl-5,5',6,6'-tetramethoxybiphenyl
790220-94-9

2,2'-divinyl-5,5',6,6'-tetramethoxybiphenyl

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 24h; Wittig reaction;100%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

(2R,3R,4S,5R)-2,3-O-isopropylidene-2,3-dihydroxy-4,5-epoxycyclopentanone
247191-04-4

(2R,3R,4S,5R)-2,3-O-isopropylidene-2,3-dihydroxy-4,5-epoxycyclopentanone

(2S,3S,4S,5R)-1-methylene-2,3-O-isopropylidene-2,3-dihydroxy-4,5-epoxycyclopentane
247191-05-5

(2S,3S,4S,5R)-1-methylene-2,3-O-isopropylidene-2,3-dihydroxy-4,5-epoxycyclopentane

Conditions
ConditionsYield
With sodium amide In tetrahydrofuran at 25℃; for 1h;100%

1779-49-3Relevant articles and documents

Synthesis of a polymerizable benzocyclobutene that undergoes ring-opening isomerization at reduced temperature

Pugh, Coleen,Baker, James S.,Storms, William K.

, p. 148 - 152 (2014)

1-Ethoxyvinylbenzocyclobutene is a substituted benzocyclobutene that undergoes radical polymerization to produce polymers that can be crosslinked at 100-150 °C. The 4- and 5-vinyl isomers are synthesized in a 1:4 ratio via a halogenated benzyne intermediate produced from anthranilic acid, followed by cycloaddition with ethyl vinyl ether and replacement of the halogen atom with a vinyl group. Georg Thieme Verlag Stuttgart · New York.

Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters

?arek, Jan,Benická, Sandra,D?ubák, Petr,Frydrych, Ivo,Gurská, Soňa,Hajdúch, Marián,Kotulová, Jana,Li?ková, Barbora,Olejníková, Denisa,Pokorny, Jan,Urban, Milan

, (2021/07/28)

A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle analysis revealed an increase in the number of apoptotic cells at 5 × IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both 4.22 and 4.39 led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 × IC50 and almost complete inhibition at 5 × IC50. Interestingly, compound 4.39 at 5 × IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations. Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds 4.22 and 4.39 trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacological parameters of derivative 4.22 were superior to 4.39, therefore 4.22 was the finally selected candidate for the development of anticancer drug.

Practical synthesis of phosphonium salts with orthoformates and their application as flame retardants in polycarbonate

Jiang, Pingkai,Li, Tao,Xu, Chencong,Zhang, Yong Jian

, (2020/03/23)

An efficient and practical approach to phosphonium salts has been developed. By the reaction of phosphines and different acid sources with orthoformates in one-step operation, the process allowed rapid access to phosphonium salts with diverse counterions in high yield after the purification by recrystallization. The flame retardant performance in PC has also been examined by blending several phosphonium salts to PC respectively. Phosphonium phosphates showed excellent flame retardancy in PC with only 2 phr blending.

Quaternary phosphonium salt flame retardant and synthesis method and application thereof

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Paragraph 0215-0219, (2020/06/20)

The invention provides a quaternary phosphonium salt flame retardant and a synthesis method and application thereof, and the method comprises the following steps: by taking an acidic compound, ortho-formic acid trisubstituted ester and an organic phosphine compound III or IV as raw materials, carrying out a one-step reaction process to prepare the quaternary phosphonium salt flame retardant I or II. The flame retardant disclosed by the invention has good thermal stability and has an excellent flame-retardant effect when being applied to various polymers. The method is simple and convenient insynthesis operation, low in raw material price, mild in synthesis condition and high in yield. According to the synthesis method, introduction of halogen ions is avoided, and dozens of anions are successfully introduced. By adding a small amount of the flame retardant, the obtained PC flame-retardant composite material UL-94 can reach the V-0 grade.

Visible Light Induced Cyclization to Spirobi[indene] Skeletons from Functionalized Alkylidienecyclopropanes

Li, Quanzhe,Liu, Jiaxin,Shi, Min,Wei, Yin

supporting information, (2020/03/26)

In this paper, we revealed a metal-free and visible light photoinduced method for the rapid construction of spirobi[indene] skeletons, providing a simple and efficient way for easy access to spirobi[indene] scaffolds under mild conditions along with a broad substrate scope and good functional group tolerance.

Organic phosphine salt and optical physical property regulation and control method and application thereof (by machine translation)

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Paragraph 0045-0053, (2020/05/30)

The invention discloses an organic phosphine salt and an optical physical property regulation and control method and application, of the compound, with different alkyl chain lengths through an ion exchange reaction; to obtain the organic phosphine salt, with different alkyl chain lengths through the ion exchange reaction to control the photophysical property (Cl, Br, I), of the compound by using alkyl, chain length and heavy atom, after, ultraviolet irradiation to achieve information, encryption application 300 nm. (by machine translation)

Exploring an Umpolung strategy for quaternization of phosphorus

Vetter, Anna C.,Nikitin, Kirill,Gilheany, Declan G.

, p. 339 - 342 (2019/03/07)

We propose a new, potentially widely-applicable, Umpolung approach for the synthesis of quaternary phosphonium salts R3PR1 X (X = Cl, Br) from phosphine oxides R3PO. The new organic group R1 is introduced via nucleophilic attack on an intermediate halophosphonium salt using a Grignard reagent R1MgX and replaces the traditional phosphine quaternization approach. Consequently, the new method does not suffer from the limited availability of many parent phosphines and is much faster than standard quaternization.

Simplified Structural Mimetics of AIPS as Quorum Sensing Inhibitors

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Paragraph 0317, (2018/07/05)

Compounds that regulate quorum sensing in Staphylococcal bacteria and in particular in Staphylococcus aureus are provided. Compounds are described in formulas I, II, III, IV, V and VI herein. One or more compounds herein can be employed to inhibit QS and to thus inhibit virulence in Staphylococcus bacteria and in particular in Staphylococcus aureus. Compounds herein and pharmaceutical compositions containing one or more of these compounds are useful, for example, in treating infections of Staphylococcus bacteria and in particular of Staphylococcus aureus. Methods for treating such bacterial infections are provided.

Synthesis method of resveratrol

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Paragraph 0041; 0042, (2018/05/03)

The invention provides a synthesis method of resveratrol, and belongs to the technical field of natural product synthesis. The synthesis method comprises the following steps: with 3,5-dimethoxy benzoic acid as a raw material, generating 3,5-dimethoxy benzoyl chloride (12) through an acylating chlorination reaction; generating 3,5-dimethoxy benzamide (13) through an amidation reaction of the (12);generating 3,5-dimethoxyaniline (14) through a Hofmann degradation reaction of the (13); generating 3,5-dimethoxy iodobenzene (15) through a Sandmeyer reaction on the (14); generating 3,5,4'-trimethoxy diphenylethene (31) through a reaction between the (15) and p-methoxystyrene (23), and performing demethylation of the (31) to finally obtain resveratrol (1), wherein total yield is 23.3%. Accordingto the method, the adopted reagent is cheap and easily available, aftertreatment is simple, and two expensive intermediates for Heck reaction are synthesized by adopting cheap raw materials. A new synthesis method is provided for synthesizing resveratrol.

Iron-Nickel Dual-Catalysis: A New Engine for Olefin Functionalization and the Formation of Quaternary Centers

Green, Samantha A.,Vásquez-Céspedes, Suhelen,Shenvi, Ryan A.

supporting information, p. 11317 - 11324 (2018/09/18)

Alkene hydroarylation forms carbon-carbon bonds between two foundational building blocks of organic chemistry: olefins and aromatic rings. In the absence of electronic bias or directing groups, only the Friedel-Crafts reaction allows arenes to engage alkenes with Markovnikov selectivity to generate quaternary carbons. However, the intermediacy of carbocations precludes the use of electron-deficient arenes, including Lewis basic heterocycles. Here we report a highly Markovnikov-selective, dual-catalytic olefin hydroarylation that tolerates arenes and heteroarenes of any electronic character. Hydrogen atom transfer controls the formation of branched products and arene halogenation specifies attachment points on the aromatic ring. Mono-, di-, tri-, and tetra-substituted alkenes yield Markovnikov products including quaternary carbons within nonstrained rings.

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