1779-49-3

Basic information

• Product Name: Methyltriphenylphosphonium bromide
• Synonyms: TRIPHENYLMETHYLPHOSPHONIUM BROMIDE;METHYLTRIPHENYLPHOSPHONIUM BROMIDE;Bromo(methyl)triphenylphosphorane;methyltriphenyl-phosphoniubromide;Phosphonium, methyltriphenyl-, bromide;Phosphonium,methyltriphenyl-,bromide;MethyltriphenylphosphoniumBromide>98%;METHYL TRIPHENYL PHOSPHONIUM BROMIDE LOW WATER
• CAS NO: 1779-49-3
• Molecular Formula: Br*C₁₉H₁₈P
• Molecular Weight: 357.22
• EINECS: 217-218-9
• Product Categories: Phosphonium Compounds;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;Wittig Reaction;C-C Bond Formation;Olefination;Wittig Reagents;organophosphorus compound
• Mol File: 1779-49-3.mol
• Article Data: 30

Chemical Properties

• Melting Point: 230-234 °C(lit.)
• Flash Point: >240°C
• Appearance: White/Powder
• Vapor Pressure: 0.0000002 hPa
• Storage Temp.: 2-8°C
• Solubility: H2O: 0.1 g/mL, clear
• Water Solubility: 400 g/L (25 ºC)
• Sensitive: Hygroscopic
• BRN: 3599467
• CAS DataBase Reference: Methyltriphenylphosphonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Methyltriphenylphosphonium bromide(1779-49-3)
• EPA Substance Registry System: Methyltriphenylphosphonium bromide(1779-49-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36/37-36-26
• RIDADR: UN 1390 4.3/PG 2
• WGK Germany: 3
• TSCA: T
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1779-49-3(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 1779-49-3 differently. You can refer to the following data:
1. PTC catalyst
2. Methyltriphenylphosphonium Bromide is a lipophilic molecule with a cation allowing for it to be used to deliver molecules to specific cell components. Also considered an antineoplastic agent.
3. Methyltriphenylphosphonium bromide is used for methylenation through the Wittig reaction. It is utilized in the synthesis of an enyne and 9-isopropenyl -phenanthrene by using sodium amide as reagent. It is a lipophilic molecule and used to deliver molecules to specific cell components. Further, it acts as an antineoplastic agent.

General Description

Methyltriphenylphosphoniumbromide is an organophosphorus compound, with potential use as a precursor and a solvent in organic synthesis.Mettler-Toledo calibration substance ME 30130598, methyltriphenylphosphoniumbromide is ideal for use in the regular calibration of Mettler-Toledo melting point instrument. Its value is a mean of 6 to 12 iterations with a Mettler-Toledo MP70 Excellence instrument that is calibrated against primary standards. The melting point is validated by Capillary method according to European Pharmacopeia (2.2.14.)

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.]

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

Synthetic route

benzaldehyde dimethyl acetal (1125-88-8) + triphenylphosphine hydrobromide (6399-81-1) → Methyltriphenylphosphonium bromide (1779-49-3)

Conditions	Yield
	100%

methanol (67-56-1) + triphenylphosphine (603-35-0) → Methyltriphenylphosphonium bromide (1779-49-3)

Conditions	Yield
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) + triphenylphosphine (603-35-0) → Methyltriphenylphosphonium bromide (1779-49-3)

Conditions	Yield
In benzene at 20℃; for 4h;	99%
In benzene for 48h; Ambient temperature;	95%
In acetonitrile

methyl bromide (74-83-9) + diphenylphosphane (829-85-6) → Methyltriphenylphosphonium bromide (1779-49-3)

Conditions	Yield
In benzene	99%

triphenylphosphine hydrobromide (6399-81-1) + trimethyl orthoformate (149-73-5) → Methyltriphenylphosphonium bromide (1779-49-3)

Conditions	Yield
at 75℃; for 0.75h; Inert atmosphere; neat (no solvent);	99%
at 70℃;	70%

methyl N-acetyl-α-triphenylphosphoniumglycinate bromide (1314805-21-4) → (N-Acetylamino)methyltriphenylphosphonium bromide (1314805-28-1) + Methyltriphenylphosphonium bromide (1779-49-3)

Conditions	Yield
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) + trimethyl orthoformate (149-73-5) → Methyltriphenylphosphonium bromide (1779-49-3)

Conditions	Yield
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 → C20H18N2O6 (498572-96-6) + Methyltriphenylphosphonium bromide (1779-49-3) + α-(N-benzoylamino)methyltriphenylphosphonium bromide (28387-29-3)

Conditions	Yield
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-)*C24H27NOP(1+) (1314805-30-5) + Methyltriphenylphosphonium bromide (1779-49-3)

Conditions	Yield
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) + triphenylphosphine (603-35-0) → Triphenylphosphine selenide (3878-44-2) + 2-(methylselanyl)-1-phenylethan-1-one (19859-29-1) + Methyltriphenylphosphonium bromide (1779-49-3) + triphenylphenacylphosphonium bromide (6048-29-9)

Conditions	Yield
In benzene for 6h; Heating; Further byproducts given;	A 7.3% B n/a C 13% D 73%

Se-phenacyldimethylselenonium bromide (19320-74-2) + triphenylphosphine (603-35-0) → Triphenylphosphine selenide (3878-44-2) + 2-(methylselanyl)-1-phenylethan-1-one (19859-29-1) + Methyltriphenylphosphonium bromide (1779-49-3) + triphenylphenacylphosphonium bromide (6048-29-9) + acetophenone (98-86-2)

Conditions	Yield
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 → Methyltriphenylphosphonium bromide (1779-49-3) + α-(N-benzoylamino)methyltriphenylphosphonium bromide (28387-29-3)

Conditions	Yield
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) + /PBFRI043-1235/ → Methyltriphenylphosphonium bromide (1779-49-3)

Conditions	Yield
With oct-1-ene; nickel dibromide In tetrahydrofuran Heating;	56%

methyl N-acetyl-α-triphenylphosphoniumglycinate bromide (1314805-21-4) → C10H14N2O6 + (N-Acetylamino)methyltriphenylphosphonium bromide (1314805-28-1) + Methyltriphenylphosphonium bromide (1779-49-3)

Conditions	Yield
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) → (chloromethyl)triphenylphosphonium bromide (111441-95-3) + Methyltriphenylphosphonium bromide (1779-49-3) + Dichlormethyl-triphenyl-phosphonium-bromid (1826-86-4)

Conditions	Yield
With 1,1-difluorotetrachloroethane In diethyl ether at -78℃; for 0.5h;	A 40% B 35% C 15%

Methylenetriphenylphosphorane (19493-09-5) → Methyltriphenylphosphonium bromide (1779-49-3) + iodomethyl triphenylphosphonium bromide (98822-67-4) + Diiodomethyl-triphenyl-phosphonium; bromide (117747-27-0)

Conditions	Yield
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) → C16H26N2O6 (498572-95-5) + Br(1-)*C24H27NOP(1+) (1314805-30-5) + Methyltriphenylphosphonium bromide (1779-49-3)

Conditions	Yield
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) → (bromomethyl)triphenyl phosphonium bromide (1034-49-7) + Methyltriphenylphosphonium bromide (1779-49-3) + tribromomethyltriphenylphosphonium bromide (56506-89-9) + (dibromomethyl)(triphenyl)phosphonium bromide (56506-90-2)

Conditions	Yield
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) + triphenylphosphine (603-35-0) → methyl bromide (74-83-9) + Methyltriphenylphosphonium bromide (1779-49-3) + 2,5-dihydro-2-oxo-3-phenyl-5-triphenylphosphoniumfuran-4-olate (100074-79-1)

Conditions	Yield
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

diazomethane (186581-53-3, 908094-01-9) + (2-Isobutyryl-vinyl)-triphenylphosphoniumbromid → Methyltriphenylphosphonium bromide (1779-49-3)

Conditions	Yield
In methanol

triphenylphosphine hydrobromide (6399-81-1) + methoxybenzene (100-66-3) → Methyltriphenylphosphonium bromide (1779-49-3)

Conditions	Yield
at 160 - 170℃;

4-bromo-1,1-dimethoxypentane (89940-00-1) + triphenylphosphine (603-35-0) → Methyltriphenylphosphonium bromide (1779-49-3)

2-methyl-1,2-epoxypropane (558-30-5) + triphenylphosphine (603-35-0) → Methyltriphenylphosphonium bromide (1779-49-3) + (2-Methyl-propenyl)-triphenyl-phosphonium; bromide (53101-88-5)

Conditions	Yield
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) + triphenylphosphine (603-35-0) → Methyltriphenylphosphonium bromide (1779-49-3)

Conditions	Yield
With hydrogen bromide; phenol 1.) 100 deg C, 24 h; Yield given. Multistep reaction;

cis-24-bromotetracos-12-enal ethylene acetal (84451-53-6) + triphenylphosphine (603-35-0) → Methyltriphenylphosphonium bromide (1779-49-3) + cis-23-(dioxolan-2-yl)tricos-12-enyltriphenylphosphonium bromide (113309-15-2)

Conditions	Yield
With trimethyl orthoformate

cis-24-bromotetracos-12-enal ethylene acetal (113309-14-1) + triphenylphosphine (603-35-0) → Methyltriphenylphosphonium bromide (1779-49-3) + trans-23-(dioxolan-2-yl)tricos-12-enyltriphenylphosphonium bromide (113309-16-3)

Conditions	Yield
With trimethyl orthoformate

triphenylphosphine (603-35-0) + methyloxirane (75-56-9, 16033-71-9) → Methyltriphenylphosphonium bromide (1779-49-3) + (2-hydroxypropyl)triphenylphosphonium bromide (3020-30-2) + (E)-prop-1-en-1-yl-triphenylphosphonium bromide (28691-76-1)

Conditions	Yield
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) + 1,2-Epoxyoctane (2984-50-1) → Methyltriphenylphosphonium bromide (1779-49-3) + ((E)-Oct-1-enyl)-triphenyl-phosphonium; bromide + ((E)-Oct-2-enyl)-triphenyl-phosphonium; bromide (56318-76-4, 88518-02-9)

Conditions	Yield
With hydrogen bromide; phenol 1.) 100 deg C, 24 h; Yield given. Multistep reaction. Yields of byproduct given;

benzophenone (119-61-9) + Methyltriphenylphosphonium bromide (1779-49-3) → 1,1-Diphenylethylene (530-48-3)

Conditions	Yield
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) + Methyltriphenylphosphonium bromide (1779-49-3) → benzyl 4-methylene-1-piperidinecarboxylate (138163-12-9)

Conditions	Yield
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) + (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) → (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)

Conditions	Yield
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) → Methylenetriphenylphosphorane (19493-09-5)

Conditions	Yield
With ammonia; sodium amide	100%
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) → diphenyl(methyl)phosphine oxide (2129-89-7)

Conditions	Yield
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) + salicylaldehyde (90-02-8) → 2-allylphenol (695-84-1)

Conditions	Yield
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) + ortho-bromobenzaldehyde (6630-33-7) → 2-bromostyrene (2039-88-5)

Conditions	Yield
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 tetrahydrofuran	99%
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) + 1-naphthaldehyde (66-77-3) → 1-vinylnaphthalene (826-74-4)

Conditions	Yield
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) + Methyltriphenylphosphonium bromide (1779-49-3) → (E)-1-Phenyl-1,3-butadiene (16939-57-4)

Conditions	Yield
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) + Methyltriphenylphosphonium bromide (1779-49-3) → 8-methylene-1,4-dioxaspiro[4.5]decane (51656-90-7)

Conditions	Yield
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 sulfoxide	90%

Methyltriphenylphosphonium bromide (1779-49-3) + 4-chloronicotinaldehyde (114077-82-6) → 4-chloro-3-vinylpyridine (223573-95-3)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran	100%
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) + (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal (289666-94-0) → (+)-(4S,5R,6R,7R)-6-benzyloxy-8-tert-butyldiphenylsilyloxy-3,3-dimethyl-4-methoxy-5,7-methylenedioxyoctyl-1-ene (289667-02-3)

Conditions	Yield
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) + Methyltriphenylphosphonium bromide (1779-49-3) → pseudo-gem-divinyl<2.2>paracyclophane (111870-60-1)

Conditions	Yield
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) + 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)-3,7,11,15-tetramethylheptadec-16-enyl]-sn-glycerol (307949-95-7)

Conditions	Yield
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) + Methyltriphenylphosphonium bromide (1779-49-3) → 4-isopropyl-5-methyl-hex-5-enenitrile (365978-53-6)

Conditions	Yield
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) + ((R)-3,4-Dihydroxy-2,2,3-trimethyl-cyclopentyl)-acetaldehyde → (S)-4-Allyl-1,5,5-trimethyl-cyclopentane-1,2-diol (383196-60-9)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran for 0.5h; Wittig olefination;	100%

Methyltriphenylphosphonium bromide (1779-49-3) + (6R)-(t-butyldimethylsilanyloxymethyl)-(2R)-ethynyl-(3R)-(triisopropylsilanyloxy)-tetrahydropyran-4-one (310398-06-2) → (6R)-(t-butyldimethylsilanyloxymethyl)-(2R)-ethynyl-4-methylene-(3S)-(triisopropylsilanoxy)-tetrahydropyran (310398-07-3)

Conditions	Yield
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) + C13H18O → C14H20

Conditions	Yield
With sodium hydride In dimethyl sulfoxide for 72h;	100%

1H-indol-2-ylcarboxaldehyde (19005-93-7) + Methyltriphenylphosphonium bromide (1779-49-3) → 2-vinyl-1H-indole (53654-35-6)

Conditions	Yield
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) + 2-isopropoxybiphenyl-3-carbaldehyde (478942-83-5) → 2-isopropoxy-3-vinyl-1,1'-biphenyl (478942-85-7)

Conditions	Yield
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) + 3-formyl-1H-indole-2-carboxylic acid (but-3-enyl)amide (519033-40-0) → 3-vinyl-1H-indole-2-carboxylic acid (but-3-enyl)amide (519033-41-1)

Conditions	Yield
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) + (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-5-(methylene)decahydronaphthalene (481656-15-9)

Conditions	Yield
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) + C91H108O17 → C92H110O16

Conditions	Yield
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) + 2-isopropoxy-4-methoxybenzene-1-carboaldehyde (107811-48-3) → 1-methoxy-5-isopropoxy-4-vinylbenzene

Conditions	Yield
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) + 2-isopropoxy-5-methoxybenzaldehyde → 2-isopropoxy-5-methoxy-1-vinylbenzene (623902-72-7)

Conditions	Yield
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) + (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

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran Wittig reaction;	100%

Methyltriphenylphosphonium bromide (1779-49-3) + (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)

Conditions	Yield
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) + (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) → (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)

Conditions	Yield
With n-butyllithium at -78℃; for 2h; Wittig methylenation;	100%

2,2'-diformyl-5,5',6,6'-tetramethoxybiphenyl (31477-10-8) + Methyltriphenylphosphonium bromide (1779-49-3) → 2,2'-divinyl-5,5',6,6'-tetramethoxybiphenyl (790220-94-9)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 24h; Wittig reaction;	100%

Methyltriphenylphosphonium bromide (1779-49-3) + (2R,3R,4S,5R)-2,3-O-isopropylidene-2,3-dihydroxy-4,5-epoxycyclopentanone (247191-04-4) → (2S,3S,4S,5R)-1-methylene-2,3-O-isopropylidene-2,3-dihydroxy-4,5-epoxycyclopentane (247191-05-5)

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

Upstream product

• 558-30-5 2-methyl-1,2-epoxypropane 
• 603-35-0 triphenylphosphine 
• 98560-25-9 epoxy-1,2 propyl-2 pentane 
• 67-56-1 methanol 
• 89940-00-1 4-bromo-1,1-dimethoxypentane 
• 6399-81-1 triphenylphosphine hydrobromide 
• 100-66-3 methoxybenzene 
• 186581-53-3 diazomethane 
• 74-83-9 methyl bromide 
• 75-16-1 methylmagnesium bromide 
• 19171-57-4 dichlorotriphenyl-λ⁴-phosphane 
• 1314805-22-5 Br^(1-)*C₂₆H₂₉NO₃P⁽¹⁺⁾ 
• 1314805-21-4 methyl N-acetyl-α-triphenylphosphoniumglycinate bromide 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 34219-91-5 1-(1-Cyclohexanecarbonyl-cyclohexyl)-2-(triphenyl-λ⁵-phosphanylidene)-ethanone 
• 22629-24-9 1-[3-(2-Methyl-[1,3]dioxolan-2-yl)-propyl]-2-methylene-cyclohexanecarboxylic acid ethyl ester 
• 24452-96-8 1-Methylen-3-tert.-butyl-cyclohexan 
• 39980-57-9 Triphenyl(pentamethyldisilanylmethylen)phosphoran 
• 4747-13-1 α-methoxystyrene 
• 5655-58-3 (1S,4R)-1,7,7-Trimethyl-2-methylene-bicyclo[2.2.1]heptane 
• 3101-50-6 1-methyl-3-methylene-cyclohexane 
• 6252-18-2 1-(1-methylethenyl)cyclohexene 
• 67883-18-5 (3-Hydroxy-3-methylbutyl)triphenylphosphoniumbromid 
• 87729-00-8 1'-phenyl-1,2-divinylbenzene 
• 112122-42-6 1-(1-Methylindol-3-yl)-1-phenyl-ethen 
• 3452-02-6 2,2,6,6-tetradeuterio-1-methylenecyclohexane 
• 5161-29-5 styrene-2,3,4,5,6-d⁵ 
• 62162-25-8 4-(phenylthio)-1-pentene 

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