1765-40-8

Basic information

• Product Name: PENTAFLUOROBENZYL BROMIDE
• Synonyms: 1-(Bromomethyl)-2,3,4,5,6-pentafluorobenzene;1-Bromomethylpentafluorobenzene;Toluene, alpha-bromo-2,3,4,5,6-pentafluoro-;PFBBR;PENTAFLUOROBENZYL BROMIDE;PENTAFLUOROBROMOMETHYL BENZENE;(BROMOMETHYL)PENTAFLUOROBENZENE;2,3,4,5,6-PENTAFLUOROBENZYL BROMIDE
• CAS NO: 1765-40-8
• Molecular Formula: C₇H₂BrF₅
• Molecular Weight: 260.99
• EINECS: 217-182-4
• Product Categories: Aromatic Halides (substituted);Analytical Chemistry;Boronic Acid, etc. (GC Derivatizing Reagents);GC Derivatizing Reagents;organofluorine compounds;Alkylation Reagent
• Mol File: 1765-40-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 19-20 °C(lit.)
• Boiling Point: 174-175 °C(lit.)
• Flash Point: 181 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.728 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.71mmHg at 25°C
• Refractive Index: n20/D 1.471(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: Hydrolyzes in water.
• Sensitive: Lachrymatory
• BRN: 647808
• CAS DataBase Reference: PENTAFLUOROBENZYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PENTAFLUOROBENZYL BROMIDE(1765-40-8)
• EPA Substance Registry System: PENTAFLUOROBENZYL BROMIDE(1765-40-8)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37/38-36/37-22
• Safety Statements: 26-36/37/39-45-23-27
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 19
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1765-40-8(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS TO YELLOWISH LIQUID

Uses

Different sources of media describe the Uses of 1765-40-8 differently. You can refer to the following data:
1. Pentafluorobenzyl bromide (PFB-Br) is an alkylating reagent which can be used to modify hydroxyl groups, carboxyl groups, sulfhydryl groups, and amines.PFB-Br can also be used to measure nitrite and peroxynitrite.It is a versatile reagent.
2. 2,3,4,5,6-Pentafluorobenzyl bromide is used as a reagent for derivatization of alcohols, carboxylic acids, sulfonamides for GC and polyfunctional thiols. It is used for the preparation of pentafluorobenzyl esters of organic acids for determination by capillary and GC. It is also used to derivatize N-7-substituted guanine adducts of DNA for determination by GC-electron capture-MS.
3. Learn more in the Product Information

General Description

Pentafluorobenzyl bromide (PFB-Br) is a derivatization reagent. Excess reagent may be removed by reaction with an aminophenol. It is an alkylation reagent suitable for electron capture detector (ECD) detection. It is also a lachrymator.

InChI:InChI=1/C7H2BrF5/c8-1-2-3(9)5(11)7(13)6(12)4(2)10/h1H2

Synthetic route

(2,3,4,5,6-pentafluorophenyl)methanol (440-60-8) → (bromomethyl)pentafluorobenzene (1765-40-8)

Conditions	Yield
With N-Bromosuccinimide; potassium hexamethylsilazane; (1,3,4)-triphenyl-4,5-dihydro-1H-1,2,4-triazol-5-ylidene In dichloromethane at 20℃; for 6h; Appel Halogenation; Inert atmosphere;	53%
With sulfuric acid; hydrogen bromide
With hydrogen bromide

2,3,4,5,6-pentafluorobenzyl(dimethyl)sulphonium bromide (118096-88-1) → 3,4,5,6-tetrafluoro-2-methylthiomethylbenzyl bromide (118096-90-5) + (E)-1-pentafluorophenyl-2-(3,4,5,6-tetrafluoro-2-methylthiomethyl)phenylethene (118096-91-6) + 1,2-bis(3,4,5,6-tetrafluoro-2-methylthiomethylphenyl)ethene (118096-92-7) + (bromomethyl)pentafluorobenzene (1765-40-8)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -70 - 20℃; for 19h; Mechanism; Product distribution;	A 2.5% B 5% C 11% D 32%

2,3,4,5,6-pentafluorotoluene (771-56-2) → (bromomethyl)pentafluorobenzene (1765-40-8)

Conditions	Yield
With bromine In tetrachloromethane
With bromine Irradiation;
Multi-step reaction with 3 steps 1: Cl2 / Irradiation 2: aq. K2CO3 / Heating 3: aq. HBr, H2SO4 View Scheme
With bromine at 36℃; for 18h; Irradiation; neat (no solvent);
With N-Bromosuccinimide at 36℃; for 18.3333h; Reactivity; Time; Irradiation; neat (no solvent);

bromopentafluorobenzene (344-04-7) → (bromomethyl)pentafluorobenzene (1765-40-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) Mg, (ii) /BRN= 636496/ 2: LiAlH4 3: aq. HBr, H2SO4 View Scheme

perfluorobenzaldehyde (653-37-2) → (bromomethyl)pentafluorobenzene (1765-40-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 2: aq. HBr, H2SO4 View Scheme

1,2,3,4,5-pentafluoro-6-iodobenzene (827-15-6) → (bromomethyl)pentafluorobenzene (1765-40-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) Mg, (ii) /BRN= 906769/ 2: LiAlH4 3: aq. HBr, H2SO4 View Scheme

2,3,4,5,6-pentafluorobenzyl chloride (653-35-0) → (bromomethyl)pentafluorobenzene (1765-40-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. K2CO3 / Heating 2: aq. HBr, H2SO4 View Scheme

2,3,4,5,6-pentafluorotoluene (771-56-2) → C7HBr2F5 (887266-89-9) + (bromomethyl)pentafluorobenzene (1765-40-8)

Conditions	Yield
With N-Bromosuccinimide at 36℃; for 18h; Irradiation; neat (no solvent);

triphenylphosphine (603-35-0) + (bromomethyl)pentafluorobenzene (1765-40-8) → (2,3,4,5,6-pentafluorobenzyl)triphenylphosphonium bromide (13509-91-6)

Conditions	Yield
In xylene at 115℃; for 18h;	100%
In toluene Reflux;	74%
In toluene for 1.5h; Heating;	61%

(bromomethyl)pentafluorobenzene (1765-40-8) + trimethylphosphane (594-09-2) → Trimethyl<(pentafluorphenyl)methyl>phosphoniumbromid (80431-31-8)

Conditions	Yield
In diethyl ether at 0℃; for 1h;	100%

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + (bromomethyl)pentafluorobenzene (1765-40-8) → (S)-tert-butyl 2-(diphenylmethyleneamino)-3-(perfluorophenyl)propanoate (1207604-26-9)

Conditions	Yield
With 2,7-bis[O(9)-allylhydrocinchonidinium-N-methyl]naphthalene dibromide; potassium hydroxide In chloroform; water; toluene at -20℃; for 84h; Inert atmosphere; optical yield given as %ee;	100%

α-picoline (109-06-8) + (bromomethyl)pentafluorobenzene (1765-40-8) → N-(pentafluorobenzyl)-2-methylpyridinium bromide (1229616-85-6)

Conditions	Yield
In chloroform at 20℃; for 24h;	100%

triethylamine (121-44-8) + (bromomethyl)pentafluorobenzene (1765-40-8) → triethyl(pentafluorobenzyl)ammonium bromide (149183-44-8)

Conditions	Yield
at 20℃; for 24h;	100%

C48H38O18 (1428628-97-0) + (bromomethyl)pentafluorobenzene (1765-40-8) → 2,2',2'',2''',2'''',2'''''-[[1,1':4',1'':4'',1''':4''',1'''':4'''',1'''''-sexiphenyl]-2'',2'''',3,3',3''',3'''''-sexiylhexakis(oxy)]hexakis[acetic acid] 01, 01',01'',01''',01'''',01'''''-hexa(2,3,4,5,6-pentafluorobenzyl)ester (1428628-89-0)

Conditions	Yield
Stage #1: C48H38O18 With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: (bromomethyl)pentafluorobenzene In N,N-dimethyl-formamide at 120℃; for 3h; Microwave irradiation;	100%

C16H14O6 + (bromomethyl)pentafluorobenzene (1765-40-8) → C30H16F10O6 (1428628-87-8)

Conditions	Yield
Stage #1: C16H14O6 With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: (bromomethyl)pentafluorobenzene In N,N-dimethyl-formamide at -10℃; for 1h;	100%

(bromomethyl)pentafluorobenzene (1765-40-8) + triethyl phosphite (122-52-1) → diethyl 2,3,4,5,6-pentafluorobenzylphosphonate (125138-11-6)

Conditions	Yield
at 140℃; for 12h;	100%
With triethylamine at 140℃; for 0.0833333h; Microwave irradiation;	99%
Arbuzov Reaction;

pyridine (110-86-1) + (bromomethyl)pentafluorobenzene (1765-40-8) → 1-(2,3,4,5,6-pentafluoro-benzyl)pyridinium bromide (164655-83-8)

Conditions	Yield
In neat (no solvent) at 50℃;	100%
In methanol for 12h; Inert atmosphere; Reflux;	94%
In acetonitrile at 88℃; for 12h;	92%
at 20℃;

1-phenylimidazole (7164-98-9) + (bromomethyl)pentafluorobenzene (1765-40-8) → 1-(2,3,4,5,6-pentafluorobenzyl)-3-phenylimidazolium bromide

Conditions	Yield
In dichloromethane at 20℃; for 24h;	100%

(bromomethyl)pentafluorobenzene (1765-40-8) + tert-butyl 2-{[(4-fluorophenyl)sulfonyl]amino}acetate (213015-69-1) → C19H17F6NO4S

Conditions	Yield
Stage #1: tert-butyl 2-{[(4-fluorophenyl)sulfonyl]amino}acetate With caesium carbonate In acetonitrile at 20℃; for 0.333333h; Inert atmosphere; Stage #2: (bromomethyl)pentafluorobenzene In acetonitrile at 20℃; for 16h; Inert atmosphere;	100%
Stage #1: tert-butyl 2-{[(4-fluorophenyl)sulfonyl]amino}acetate With caesium carbonate In acetonitrile Stage #2: (bromomethyl)pentafluorobenzene In acetonitrile at 20℃; for 16h;	96%

N-BOC-1,2-diaminoethane (57260-73-8) + (bromomethyl)pentafluorobenzene (1765-40-8) → tert–butyl (2-(((perfluorophenyl)methyl)amino)ethyl)carbamate (887150-20-1)

Conditions	Yield
With potassium carbonate In acetonitrile at 22℃; for 25h;	100%

bis(benzenethiolato)lead(II) (32812-89-8) + (bromomethyl)pentafluorobenzene (1765-40-8) → 1,2,4,5-Tetrafluoro-3-phenylsulfanyl-6-phenylsulfanylmethyl-benzene

Conditions	Yield
In N,N-dimethyl-formamide for 23h; Heating;	99%

(bromomethyl)pentafluorobenzene (1765-40-8) + Pb(SPh)2 → 1,2,4,5-Tetrafluoro-3-phenylsulfanyl-6-phenylsulfanylmethyl-benzene

Conditions	Yield
In N,N-dimethyl-formamide for 23h; Heating;	99%

Triphenylmethylamin (5824-40-8) + (bromomethyl)pentafluorobenzene (1765-40-8) → N-trityl-2,3,4,5,6-pentafluorobenzylamine (1161882-79-6)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	99%

(bromomethyl)pentafluorobenzene (1765-40-8) + 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-ylamino)-benzoic acid ethyl ester (214694-10-7) → ethyl 4-[N-pentafluorobenzyl-N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)amino]benzoate (1300118-25-5)

Conditions	Yield
Stage #1: 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-ylamino)-benzoic acid ethyl ester With sodium hydride In N,N-dimethyl-formamide for 0.333333h; Inert atmosphere; Stage #2: (bromomethyl)pentafluorobenzene In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	99%

(bromomethyl)pentafluorobenzene (1765-40-8) + triethyl phosphite (122-52-1) → ethylphosphonic acid diethyl ester (78-38-6) + 2,3,4,5,6-pentafluorobenzylphosphonic acid ethyl ester

Conditions	Yield
at 160℃; for 12h;	A n/a B 99%

benzyl 2-(benzyloxy)-4-(N-(4-cyclohexylbenzyl)-2-(perfluorophenylsulfonamido)acetamido)benzoate (1455006-14-0) + (bromomethyl)pentafluorobenzene (1765-40-8) → benzyl 2-(benzyloxy)-4-(N-(4-cyclohexylbenzyl)-2-(2,3,4,5,6-pentafluoro-N-((perfluorophenyl)methyl)phenylsulfonamido)acetamido)benzoate (1455006-39-9)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	99%

1-vinylimidazole (1072-63-5) + (bromomethyl)pentafluorobenzene (1765-40-8) → 3-(2,3,4,5,6-pentafluorobenzyl)-1-vinylimidazol-1-ium bromide

Conditions	Yield
In acetonitrile at 20℃; for 48h; Cooling with ice; Inert atmosphere;	99%
In acetonitrile at 88℃; for 12h;	91%

(bromomethyl)pentafluorobenzene (1765-40-8) + methyl 3-formyl-6-indolecarboxylate (133831-28-4) → methyl 3–formyl–1-((perfluorophenyl)methyl)-1H–indole–6–carboxylate

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 18h; Inert atmosphere;	99%

(η5-cyclopentadienyl)(dppe)Ru((N2)-4,5-bis(methoxycarbonyl)-1,2,3-triazolato) (561297-18-5) + (bromomethyl)pentafluorobenzene (1765-40-8) → (η5-C5H5)(1,2-bis(diphenylphosphino)ethane)ruthenium(Br)

Conditions	Yield
In dichloromethane byproducts: N3(CH2C6F5)C2(CO2Me)2; under N2; CH2Cl2 added to Ru complex and BrCH2C6F5 (molar ratio 1:5), stirred at 40°C for 48 h; at 50°C and 20-fold excess of BrCH2C6F5 react. completed in 1 d; solvent removed under vac.; cold n-pentane added; filtered; ppt. washed with n-pentane; dried under vac.; elem. anal.;	98%

phenylacetylene (536-74-3) + (bromomethyl)pentafluorobenzene (1765-40-8) → 1-((perfluorophenyl)methyl)-4-phenyl-1H-1,2,3-triazole

Conditions	Yield
With copper(l) iodide; sodium azide; diethylamine In glycerol at 20℃; for 5h; Schlenk technique; Inert atmosphere; Green chemistry;	98%
With sodium azide; C24H20N6*2I(1-)*2Cu(1+) In water at 25℃; for 12h;	33 %Chromat.

4-tert-butylpyridine (3978-81-2) + (bromomethyl)pentafluorobenzene (1765-40-8) → 4-tert-butyl-N-((pentafluorophenyl)methyl)pyridinium bromide (1609277-94-2)

Conditions	Yield
In neat (no solvent) at 50℃;	98%

(bromomethyl)pentafluorobenzene (1765-40-8) + 1-methyl-2-[(2,3,4,5,6-pentafluorobenzyl)thio]imidazole → 3-methyl-1-(2,3,4,5,6-pentafluorobenzyl)-2-[(2,3,4,5,6-pentafluorobenzyl)thio]imidazol-1-ium bromide

Conditions	Yield
In acetonitrile at 20℃; for 144h; Inert atmosphere;	98%

methyl (E)-3-(4-(prop–2–yn–1–ylamino)phenyl)acrylate + (bromomethyl)pentafluorobenzene (1765-40-8) → methyl (E)-3-(4-((((perfluorophenyl)methyl)(prop–2–yn–1–yl)amino)methyl)phenyl)acrylate

Conditions	Yield
Stage #1: methyl (E)-3-(4-(prop–2–yn–1–ylamino)phenyl)acrylate With potassium carbonate In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Stage #2: (bromomethyl)pentafluorobenzene In acetonitrile at 20℃; for 14h; Inert atmosphere;	98%

C22H28O6P2 + (bromomethyl)pentafluorobenzene (1765-40-8) → C36H30F10O6P2

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	98%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 30℃;	98%

3-{[(tert-butyl)dimethylsilyl]oxy}-5-hydroxybenzyl alcohol (641571-45-1) + (bromomethyl)pentafluorobenzene (1765-40-8) → 3-{[(tert-butyl)dimethylsilyl]oxy}-5-[(2,3,4,5,6-pentafluorobenzyl)oxy]benzyl alcohol (875051-01-7)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetone at 20℃; for 72h;	97.5%

2,6-difluorophenol (28177-48-2) + (bromomethyl)pentafluorobenzene (1765-40-8) → 1-(2,6-Difluoro-phenoxymethyl)-2,3,4,5,6-pentafluoro-benzene

Conditions	Yield
With potassium carbonate In acetone	97%

(bromomethyl)pentafluorobenzene (1765-40-8) + C15H17N3O2S2 (157460-18-9) → C22H19F5N3O2S2(1+)*Br(1-)

Conditions	Yield
In dichloromethane for 12h; Heating;	97%

(bromomethyl)pentafluorobenzene (1765-40-8) + tris(1-methylethyl)phosphine (6476-36-4) → Triisopropyl<(pentafluorphenyl)methyl>phosphoniumbromid (80438-16-0)

Conditions	Yield
In benzene for 5h; Heating;	97%

Upstream product

• 771-56-2 2,3,4,5,6-pentafluorotoluene 
• 653-35-0 2,3,4,5,6-pentafluorobenzyl chloride 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 
• 653-37-2 perfluorobenzaldehyde 
• 344-04-7 bromopentafluorobenzene 
• 440-60-8 (2,3,4,5,6-pentafluorophenyl)methanol 
• 118096-88-1 2,3,4,5,6-pentafluorobenzyl(dimethyl)sulphonium bromide 

Downstream Products

• 754-41-6 2-(fluorosulfonyl)tetrafluoropropionyl fluoride 
• 132130-94-0 1,1,1,2,3,3-Hexafluoro-3-pentafluorophenylmethoxy-propane-2-sulfonyl fluoride 
• 291545-31-8 (2,3,4,5,6-pentafluorophenyl)methyl 10-(2-aza-2-methoxy-1-methylvinyl)-11-(2-aza-2-methoxyvinyl)-14-hydroxynonadeca-4(Z),7(Z),12(E),16(Z)-tetraenoate 

Relevant articles and documents

Analysis of hydrogen bonding strengths in proteins using unnatural amino acids

-

Visible-light-promoted Wohl-Ziegler functionalization of organic molecules with N-bromosuccinimide under solvent-free reaction conditions

The visible-light-induced transformation of toluenes with N-bromosuccinimide (NBS) under solvent-free reaction conditions (SFRC) was studied. The reaction took place in spite of the very restricted molecular motion; toluenes could be regioselectively converted to benzyl bromides. Selective radical-chain reactions with NBS were carried out in liquid/liquid and in solid/solid systems; furthermore, reactions could be performed in the presence of air. The radical scavenger TEMPO (=2,2,6,6-tetramethylpiperidin-1- yloxy) completely suppressed the side-chain bromination of toluenes with NBS under SFRC. Electron-withdrawing groups decreased the reactivity of the toluenes, and the Hammett reaction constant ρ+ = -1.7 indicated involvement of polar radical intermediates with electrophilic character.

Diphenyl ether derivatives

-