100-58-3

Basic information

• Product Name: PHENYLMAGNESIUM BROMIDE
• Synonyms: bromophenylmagnesium;PHENYLMAGNESIUM BROMIDE, 3.0M SOLUTION I N DIETHYL ETHER;PHENYLMAGNESIUM BROMIDE SOLUTION, ~1 M I N THF;PHENYLMAGNESIUM BROMIDE SOL., ~3 M IN DI ETHYL ETHER;PHENYLMAGNESIUM BROMIDE, 1.0M SOLUTION I N TETRAHYDROFURAN;Phenylmagnesium Bromide 1.0 M In Tetrahydrofuran;Phenylmagnesium Bromide 3.0 M In Diethyl Ether;Phenylmagnesium bromide, 1M solution in THF
• CAS NO: 100-58-3
• Molecular Formula: Br*C₆H₅*Mg
• Molecular Weight: 181.31
• EINECS: 202-867-2
• Product Categories: Organometallics;GRIGNARD REAGENTS;Classes of Metal Compounds;Grignard Reagents & Alkyl Metals;Mg (Magnesium) Compounds;Synthetic Organic Chemistry;Typical Metal Compounds;Aryl;Grignard Reagents;Organometallic Reagents;grignard reagent;Chemical Synthesis;Organometallic Reagents;WB;Imidazoles ,Benzimidazoles
• Mol File: 100-58-3.mol
• Article Data: 57

Chemical Properties

• Melting Point: 153-154 °C
• Boiling Point: 78.8oC at 760 mmHg
• Flash Point: −40 °F
• Appearance: Yellow to brown/Liquid
• Density: 1.134 g/mL at 25 °C
• Storage Temp.: water-free area
• Solubility: Miscible with tetrahydrofuran.
• Water Solubility: reacts
• Sensitive: Air & Moisture Sensitive
• BRN: 3588849
• CAS DataBase Reference: PHENYLMAGNESIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLMAGNESIUM BROMIDE(100-58-3)
• EPA Substance Registry System: PHENYLMAGNESIUM BROMIDE(100-58-3)

Safety Data

• Hazard Codes: F+,C,F
• Statements: 12-14-22-34-19-11-67-40-37
• Safety Statements: 16-26-36/37/39-45-33-29-7/8-6A-43B
• RIDADR: UN 3399 4.3/PG 1
• WGK Germany: 1
• F: 1-3-10
• TSCA: Yes
• HazardClass: 4.3
• PackingGroup: II
• Hazardous Substances Data: 100-58-3(Hazardous Substances Data)

Usage

Reduction agent for preparation of metal carbonyl compound

In 1890, L.Mond found that when carbon monoxide was burned after being put through the active metal nickel powder, it emitted green light flame. After the resulting gas was cooled, he could obtain colorless liquid (melting point 298K, the boiling point of 316K); if this gas is flowed through a heated glass tube, then it can be seen that the metallic nickel was deposited on the wall. This gas is tetracarbonyl nickel Ni(CO)4. Since the 1960s, people have synthesized a hundreds kinds of such carbonyl compounds and their derivatives. Almost all of the transition metal can form such compounds. This kind of special complex formed through transition metal with carbon monoxide ligands is called metal carbonyls, otherwise known as carbonyl complexes. Metal carbonyl occupies an important position in both theoretical research and practical application in modern inorganic chemistry. Preparation of metal carbonyl compound can usually via the following methods: 1. Direct synthesis. Most metal carbonyl complexes are prepared by direct combination between metal and carbon monoxide. However, the metal must be new reduction products, and is in a very activated state. 2. Reduction carbonylation effect at high pressure. Apply reducing agent under high pressure to enable the carbonylation reaction between the metal and carbonyl group with the major reducing agents mainly including hydrogen, active metals, phenylmagnesium bromide (C6H5MgBr) and so on. 3. With thermal decomposition or UV irradiation decomposition, we can obtain certain polynuclear carbonyl compounds. 4. Two different kinds of metal carbonyl compounds can interact with each other to give hetero-nuclear carbonyl compound.

Related chemical reaction

1. Phenylmagnesium bromide can react with ferric chloride to give the coupling product. Cyclopentadienyl magnesium bromide can react with ferric chloride to give ferrocene. 2. It can react with chromium trichloride in diethyl ether solution to generate dibenzenechromium. 3. Hexaphenyldilead can be used as the antioxidant of polyphenylene ether lubricant that can be produced from the reaction of lead chloride with phenyl lithium or phenyl magnesium bromide. 4. Take tetrahydrofuran as the solvent, have phenylmagnesium bromide reacted with germanium tetrachloride to obtain tetraphenyl germane. 5. It can be obtained through the low-temperature reaction between lead chloride and phenylmagnesium bromide (Or phenyllithium) in the presence of iodobenzene to derive tetraphenyl lead. 6. Sodium tetraphenylborate is mainly used for the determination of potassium ion, ammonium ion, rubidium ion and cesium ion. It can be obtained with the following process: phenylmagnesium bromide is interacted with boron trifluoride/diethyl ether to generate Tetraphenylboron magnesium bromide first. Evaporate the diethyl ether; add water and then used the calculated amount of sodium carbonate for treatment to obtain it.

Chemical Properties

Clear light brown to brown solution when properly

Uses

Phenylmagnesium Bromide is a reagent used in the preparation of arylcarbonimidic dichlorides via dichloroiodobenzene-mediated gem-dichlorination of aryl isonitriles.

Uses

Grignard reagent in greener solvent, 2-methyltetrahydrofuran (2-MeTHF)2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry

InChI:InChI=1/C6H5.BrH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1/rC6H5BrMg/c7-8-6-4-2-1-3-5-6/h1-5H

Synthetic route

bromobenzene (108-86-1) → phenylmagnesium bromide (100-58-3)

Conditions	Yield
With magnesium In tetrahydrofuran at 40℃; for 0.25h; Inert atmosphere; Flow reactor;	100%
With magnesium In tetrahydrofuran
With magnesium In diethyl ether at 19.9℃; Rate constant; various concentrations of aryl halide;

2-amino-5-chlorobenzonitrile (5922-60-1) → (2-amino-5-chlorophenyl)-phenyl-methane-imine (5606-39-3) + phenylmagnesium bromide (100-58-3)

Conditions	Yield
	A 92% B n/a

bromobenzene (108-86-1) → 1-phenyltetrafluoro-2-propenylacetate + phenylmagnesium bromide (100-58-3)

Conditions	Yield
With magnesium In tetrahydrofuran	A 24% B n/a

1,3,5-trisbromobenzene (626-39-1) + dichlorobis(triphenylphosphine)palladium[II] + Diisobutylaluminium hydride(1 M solution in tetrahydrofuran, 4.9 mL, 4.9 mmol) → phenylmagnesium bromide (100-58-3)

Conditions	Yield
In tetrahydrofuran; toluene

bromobenzene (108-86-1) + N-Z-(S)-serine methyl ester → phenylmagnesium bromide (100-58-3)

Conditions	Yield
With hydrogenchloride In diethyl ether

bromobenzene (108-86-1) + (S)-Carbomethoxy oxazolidinone → phenylmagnesium bromide (100-58-3)

Conditions	Yield
In tetrahydrofuran

ethyl 2-cyanoacetate (105-56-6) → phenylmagnesium bromide (100-58-3)

Conditions	Yield
With ammonium chloride

[NitriphosCl]PF6 + 1,2-dichloro-benzene (95-50-1) → phenylmagnesium bromide (100-58-3)

Conditions	Yield
With biphenyl; ethylmagnesium bromide; phenylmagnesium bromide In o-xylene

1-phenyl-2-bromoethane (103-63-9) + ethyl 2-cyanoacetate (105-56-6) → phenylmagnesium bromide (100-58-3)

Conditions	Yield
With hydrogenchloride; iodine In magnesium

bromobenzene (108-86-1) + ethyl 2-cyanoacetate (105-56-6) → phenylmagnesium bromide (100-58-3)

Conditions	Yield
With magnesium

bromobenzene (108-86-1) + 1-methyl-3-fluoro-5,7-dichloro-2,3-dihydro-1H-1,4-benzodiazepin-2-one (60628-69-5) → 3-fluorodiazepam + phenylmagnesium bromide (100-58-3)

Conditions	Yield
With HF In tetrahydrofuran

bromobenzene (108-86-1) + dimethyl-2,3-O-cyclohexylidene-L-tartrate → (-)-2,3-O-cyclohexylidene-1,1,4,4-tetra-phenyl-L-threitol + phenylmagnesium bromide (100-58-3)

Conditions	Yield
With magnesium In diethyl ether	A 17 g (34%) B n/a

bromobenzene (108-86-1) + magnesium (7439-95-4) → phenylmagnesium bromide (100-58-3)

Conditions	Yield
In tetrahydrofuran
In tetrahydrofuran for 1.5h; Inert atmosphere; Reflux;
With iodine In tetrahydrofuran for 2h; Inert atmosphere; Reflux;
With iodine In tetrahydrofuran for 1h; Grignard Reaction; Heating / reflux;

bromobenzene (108-86-1) + magnesium → phenylmagnesium bromide (100-58-3)

Conditions	Yield
With diethyl ether

bromobenzene (108-86-1) → phenylmagnesium bromide (100-58-3)

Conditions	Yield
With diethyl ether untersucht wurde die Geschwindigkeit;

phenylmagnesium bromide (100-58-3) → biphenyl (92-52-4)

Conditions	Yield
With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone at -20℃; Product distribution / selectivity;	100%
With iron(III) chloride; 1,2-dichloro-ethane In tetrahydrofuran at 0℃; for 0.0833333h; Ionic liquid; Inert atmosphere;	100%
With 1,2-bisperfluorotolyl-3,3,4,4,5,5-hexafluorocyclopentene In tetrahydrofuran at 25℃; for 1h; Reagent/catalyst; Inert atmosphere;	99%

chlorobenzene (108-90-7) + phenylmagnesium bromide (100-58-3) → biphenyl (92-52-4)

Conditions	Yield
nickel(II) In tetrahydrofuran for 18h; Product distribution; other catalyst, other solvents; other Grignard compounds and alkyl or vinyl halides;	100%
With CpNi[1-(ethoxycarbonyl)methyl-3-(3,5-dimethylbenzyl)benzimidazolin-2-ylidene]Br In tetrahydrofuran at 25℃; for 3h; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique;	97%
With Pd/Al(OH)3 In toluene at 140℃; for 36h; Kumada Cross-Coupling; Inert atmosphere;	94%

phenylmagnesium bromide (100-58-3) + 5,6,7,8-tetrachloro-3,4-dihydro-1,4-ethanonaphthalen-2(1H)-one → 5,6,7,8-tetrachloro-1,4-dihydro-9-hydroxy-9-phenyl-1,4-ethanonaphthalene

Conditions	Yield
In diethyl ether for 4h; Ambient temperature;	100%

phenylmagnesium bromide (100-58-3) + 5,6,7,8-tetrachloro-3,4-dihydro-1,4-ethanonaphthalen-2(1H)-one → 5,6,7,8-tetrachloro-1,4-dihydro-9-endo-hydroxy-9-phenyl-1,4-ethanonaphthalene

Conditions	Yield
In diethyl ether for 4h; Ambient temperature;	100%

benzoyl chloride (98-88-4) + phenylmagnesium bromide (100-58-3) → benzophenone (119-61-9)

Conditions	Yield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 0℃;	100%
Stage #1: benzoyl chloride With 1-methyl-pyrrolidin-2-one In toluene at 0℃; for 0.5h; Stage #2: phenylmagnesium bromide In tetrahydrofuran; toluene at -10 - 0℃; for 4.25h; chemoselective reaction;	89%
In 2-methyltetrahydrofuran at 25℃; for 1h; Solvent; Concentration; Flow reactor; Green chemistry;	85%

3-phenylbutanoyl chloride (51552-98-8) + phenylmagnesium bromide (100-58-3) → 1,3-diphenylbutane-1-one (1533-20-6)

Conditions	Yield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 0℃;	100%

phenylmagnesium bromide (100-58-3) + methyl 1-benzylpyrazole-3-carboxylate (7188-98-9) → (1-Benzyl-1H-pyrazol-3-yl)-diphenyl-methanol

Conditions	Yield
In tetrahydrofuran	100%

methyl 3,3-dimethylglutarate (19184-67-9) + phenylmagnesium bromide (100-58-3) → 3,3-dimethy-5,5-diphenyl-5-hydroxypentanoic acid lactone (53392-28-2)

Conditions	Yield
In tetrahydrofuran 2 h; reflux, 2,5 h;	100%

phenylmagnesium bromide (100-58-3) + methyl (S)-N-(tert-butoxycarbonyl)indoline-2-carboxylate (197460-36-9) → (S)-tert-butyl 2-(hydroxydiphenylmethyl)indoline-1-carboxylate (197460-37-0)

Conditions	Yield
In diethyl ether at 0℃; Inert atmosphere; Reflux;	100%
In tetrahydrofuran; diethyl ether at 0 - 20℃; for 7h;	25%
In diethyl ether at 0℃;

phenylmagnesium bromide (100-58-3) + (4-Methoxy-phenyl)-(4-phenyl-phthalazin-1-yl)-methanone (204520-35-4) → (4-Methoxy-phenyl)-phenyl-(4-phenyl-phthalazin-1-yl)-methanol (204520-30-9)

Conditions	Yield
In tetrahydrofuran for 1h; Ambient temperature;	100%

phenylmagnesium bromide (100-58-3) + (2R,9S)-2,9-diphenyl-1-aza-4-oxabicyclo[4.3.0]nonane (205526-47-2) → (2S,6R,1'R)-N-2'-hydroxy-1'-phenylethyl-2,6-diphenylpiperidine (205526-49-4)

Conditions	Yield
In tetrahydrofuran at 0℃; for 72h;	100%

para-bromotoluene (106-38-7) + phenylmagnesium bromide (100-58-3) → 4-Methylbiphenyl (644-08-6)

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)-imidazolium][Ni(PPh3)Cl3] In tetrahydrofuran at 30℃; for 1h; Kumada Cross-Coupling; Schlenk technique; Inert atmosphere;	100%
With C70H40Cl2F68N2O6Pd2 In tetrahydrofuran at 100℃; for 0.0166667h; Kumada coupling reaction; Microwave irradiation;	96%
With C17H36ClN6NiP2(1+)*Cl(1-) In tetrahydrofuran for 6h; Reagent/catalyst; Kumada Cross-Coupling; Inert atmosphere;	96%

3-(3-bromophenyl)-N-methoxy-N-methylpropanamide (937375-28-5) + phenylmagnesium bromide (100-58-3) → 3-(3-bromophenyl)-1-phenyl-propan-1-one (65565-12-0)

Conditions	Yield
In tetrahydrofuran at -78 - 0℃; for 2h;	100%

(R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (884510-86-5) + phenylmagnesium bromide (100-58-3) → (R)-tert-butyl 3-benzoylpiperidine-1-carboxylate (884510-87-6)

Conditions	Yield
Stage #1: (R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate; phenylmagnesium bromide In tetrahydrofuran at -10 - 20℃; for 1.25h; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 0.333333h; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water	100%
Stage #1: (R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate; phenylmagnesium bromide In tetrahydrofuran at -10 - 20℃; for 1.25h; Stage #2: With hydrogenchloride; water In tetrahydrofuran for 0.333333h;	100%
Stage #1: (R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate; phenylmagnesium bromide In tetrahydrofuran at -10 - 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water

3-cyanobromobenzene (6952-59-6) + phenylmagnesium bromide (100-58-3) → C13H10BrN

Conditions	Yield
Stage #1: 3-cyanobromobenzene; phenylmagnesium bromide In tetrahydrofuran at 20 - 60℃; for 4h; Stage #2: With methanol In tetrahydrofuran at 0℃;	100%
Stage #1: 3-cyanobromobenzene; phenylmagnesium bromide In tetrahydrofuran at 20 - 60℃; for 4h; Stage #2: With methanol In tetrahydrofuran at 0℃;

4-butanolide (96-48-0) + phenylmagnesium bromide (100-58-3) → 1,1-diphenylbutan-1,4-diol (1023-94-5)

Conditions	Yield
With hydrogenchloride; ammonium chloride In tetrahydrofuran	100%
Stage #1: 4-butanolide; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at -78 - 20℃; Inert atmosphere; Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether at 10℃; Cooling with ice;
In tetrahydrofuran Grignard reaction; Reflux;

3-Ethoxycyclohex-2-en-1-one (5323-87-5) + phenylmagnesium bromide (100-58-3) → 3-phenylcyclohex-2-enone (10345-87-6)

Conditions	Yield
Stage #1: 3-Ethoxycyclohex-2-en-1-one; phenylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: With hydrogenchloride; water In tetrahydrofuran	100%
Stage #1: 3-Ethoxycyclohex-2-en-1-one; phenylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: With hydrogenchloride; water In tetrahydrofuran	100%
Stage #1: 3-Ethoxycyclohex-2-en-1-one; phenylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃;	100%

2-fluoropyridine (372-48-5) + phenylmagnesium bromide (100-58-3) → 2-phenylpyridine (1008-89-5)

Conditions	Yield
Stage #1: 2-fluoropyridine; phenylmagnesium bromide; bis(acetylacetonate)nickel(II); ((2-hydroxymethyl)phenyl)diphenylphosphine In diethyl ether for 0.5h; Stage #2: With methanol In diethyl ether Product distribution / selectivity;	100%
Stage #1: 2-fluoropyridine; phenylmagnesium bromide; 1-[2-(diphenylphosphino)phenyl]ethanol; bis(acetylacetonate)nickel(II) In diethyl ether for 2h; Stage #2: With methanol In diethyl ether Product distribution / selectivity;	96%

2-bromo-3,5-bis(methoxymethoxy)-6-phenylbenzaldehyde (860155-48-2) + phenylmagnesium bromide (100-58-3) → 1-[2-bromo-3,5-bis(methoxymethoxy)-6-phenylphenyl]-1-phenylmethanol (860155-59-5)

Conditions	Yield
In tetrahydrofuran; diethyl ether at 0℃; for 2h;	100%

N-(2-Diethylaminoethyl)-4'-(1-oxo-2-phenylbutyl)methanesulfonanilide (58233-95-7) + phenylmagnesium bromide (100-58-3) → N-(2-Diethylaminoethyl)-4'-(1-hydroxy-1,2-diphenylbutyl)methanesulfonanilide (58233-96-8)

Conditions	Yield
With hydrogenchloride; ammonium chloride In diethyl ether; water	100%

N-carbethoxytropinone (32499-64-2) + phenylmagnesium bromide (100-58-3) → C16H21NO3 (861853-58-9)

Conditions	Yield
In tetrahydrofuran at 20℃; for 5h;	100%

(Et2C2B4H4)(Cp)TaCl2 (162476-46-2) + phenylmagnesium bromide (100-58-3) → (Et2C2B4H4)(Cp)TaPh2

Conditions	Yield
In diethyl ether; toluene Ar-atmosphere; stirring (1 h); filtering, evapn. (vac.), extg. (CH2Cl2), filtering, evapn., washing (pentane);	100%
In tetrahydrofuran

phenylmagnesium bromide (100-58-3) + (Z)-3-Trimethylstannanyl-hept-2-enal (180070-95-5, 180070-96-6) → 1-phenyl-3-trimethylstannyl-hept-2-ene-1-al (180071-40-3, 180071-39-0)

Conditions	Yield
In diethyl ether Ar-atmosphere; slight excess PhMgBr, refluxing for 12 h; addn. of satd. aq. NH4Cl, extn. of aq. layer (Et2O), drying (MgSO4), solvent removal; isomer mixt. not sepd., detd. by (119)Sn-NMR spectroscopy;	100%

1-(4-fluorophenyl)-1H-indazole-5-carbaldehyde (917494-83-8) + phenylmagnesium bromide (100-58-3) → (1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanol (1025762-60-0)

Conditions	Yield
Stage #1: 1-(4-fluorophenyl)-1H-indazol-5-carboxaldehyde; phenylmagnesium bromide In tetrahydrofuran at 0℃; for 1h; Stage #2: With water; ammonium chloride In tetrahydrofuran	100%
Stage #1: 1-(4-fluorophenyl)-1H-indazol-5-carboxaldehyde; phenylmagnesium bromide In tetrahydrofuran at 0℃; for 1h; Stage #2: With water; ammonium chloride In tetrahydrofuran	100%

5-formyl-N,N-dimethyl-1H-indole-1-carboxamide (1025763-25-0) + phenylmagnesium bromide (100-58-3) → 5-(hydroxy(phenyl)methyl)-N,N-dimethyl-1H-indole-1-carboxamide (1025763-27-2)

Conditions	Yield
Stage #1: 5-formyl-N,N-dimethyl-1H-indole-1-carboxamide; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at -78 - 20℃; for 2h; Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether	100%
In tetrahydrofuran	100%

trifluoromethanesulfonic acid 1-bromonaphthalen-2-yl ester (126613-08-9) + phenylmagnesium bromide (100-58-3) → 1-bromo-2-phenylnaphthalene (22082-93-5)

Conditions	Yield
Stage #1: trifluoromethanesulfonic acid 1-bromonaphthalen-2-yl ester With 1,3-bis-(diphenylphosphino)propane; lithium bromide; tris-(dibenzylideneacetone)dipalladium(0) In diethyl ether at 20℃; for 0.0833333h; Stage #2: phenylmagnesium bromide In diethyl ether at 0 - 20℃; for 7h;	100%
With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); lithium bromide In diethyl ether at 0℃; for 18h; Inert atmosphere;
With bis(diphenylphosphino)propanepalladium(II) dichloride; lithium bromide In diethyl ether for 1h; Inert atmosphere; Cooling with ice;	17 g

(3E,4aR,10aR)-3-benzylidene-4a-ethyl-7-hydroxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one (645396-79-8) + phenylmagnesium bromide (100-58-3) → (2S,3E,4aR,10aR)-3-benzylidene-4a-ethyl-2-phenyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-2,7-diol (645396-80-1)

Conditions	Yield
Stage #1: phenylmagnesium bromide With cerium(III) chloride In tetrahydrofuran at -78℃; for 1.5h; Stage #2: (3E,4aR,10aR)-3-benzylidene-4a-ethyl-7-hydroxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one In tetrahydrofuran at -40℃; for 2h; Stage #3: With water; acetic acid In tetrahydrofuran	100%
Stage #1: phenylmagnesium bromide With cerium(III) chloride In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: (3E,4aR,10aR)-3-benzylidene-4a-ethyl-7-hydroxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-one In tetrahydrofuran at -70 - -40℃; for 2.5h; Inert atmosphere;	96%

phenylmagnesium bromide (100-58-3) + (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide (537030-19-6) → (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-1-hydroxy-5-phenylpyrrolidine (1000612-60-1)

Conditions	Yield
In tetrahydrofuran at 0℃; for 3h;	100%

3,6-di(piperidin-1-yl)-9H-xanthen-9-one (1023903-94-7) + phenylmagnesium bromide (100-58-3) → C29H31N2O(1+)*Cl(1-) (1174713-22-4, 1079889-38-5)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃;	100%

Upstream product

• 10058-23-8 potassium hydrogenperoxomonosulphate 
• 10058-20-5 Succinic acid bis[2-(hexyloxy)ethyl] ester 
• 100581-95-1 (E)-4-(hexadecylamino)-4-oxo-2-butenoic acid 
• 10058-19-2 6-O-ALPHA-D-GLUCOSYL-ALPHA-CYCLODEXTRIN MONO 
• 100581-42-8 ETH 500 
• 10058-11-4 1-(4-methoxyphenyl)-1H-imidazolium chloride 
• 10058-07-8 nicotinic acid, compound with 3,7-dihydro-1,3-dimethyl-7-[2-[(3-pyridylmethyl)amino]ethyl]-1H-purine-2,6-dione (1:1) 
• 1005788-25-9 6-IODO-IMIDAZO[1,2-B]PYRIDAZINE-2-METHANOL 
• 1005787-84-7 tert-butyl N-{6-iodoiMidazo[1,2-b]pyridazin-2- yl}carbaMate 
• 1005786-10-6 6-IODOIMIDAZO[1,2-B]PYRIDAZINE-2-CARBOXYLIC ACID ETHYL ESTER 
• 1005786-00-4 4-(1-((Tert-Butyldimethylsilyl)Oxy)-2-Methylpropan-2-Yl)Benzoic Acid 
• 1005785-87-4 6-(trifluoromethyl)H-imidazo[1,2-a]pyridin-2-amine 
• 1005785-85-2 5-terbutylpieolinic acid 
• 1005785-80-7 6-(pyridin-3-yl)imidazo[1,2-b]pyridazin-2-amine 

Downstream Products

• 756520-78-2 2-(Methanesulfonylamino)phenylboronic acid 
• 55135-66-5 9-Bromo-9-phenylfluorene 
• 612-96-4 2-Phenylquinoline 
• 524-95-8 (2-AMINOETHOXY)DIPHENYLBORANE 
• 112068-01-6 (S)-(?)-α,α-Diphenyl-2-pyrrolidinemethanol 
• 112022-81-8 (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole 
• 1013-88-3 Benzophenone imine 
• 5570-19-4 2-Nitrophenylboronic acid 

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• 584-12-3  2-bromofuran 
• 13679-41-9  3-phenylfuran 
• 22037-28-1  3-bromofurane 
• 92-52-4  biphenyl 
• 1118-66-7  4-Aminopent-3-en-2-one 
• 26567-78-2  (Z)-4-(phenylamino)-3-penten-2-one