5707-04-0

Basic information

• Product Name: PHENYLSELENENYL CHLORIDE
• Synonyms: PHENYLSELENENYL CHLORIDE;PHENYLSELENIUM CHLORIDE;PHENYLSELENYL CHLORIDE;chloroselenobenzene;Phenylselenenylchloride,98%;Phenylselenyl chloride, 97+%;Benzeneselenenyl chloride, Benzeneselenyl chloride;Benzeneselenenic acid chloride
• CAS NO: 5707-04-0
• Molecular Formula: C₆H₅ClSe
• Molecular Weight: 191.52
• EINECS: 227-196-2
• Product Categories: Classes of Metal Compounds;Se (Selenium) Compounds;Semimetal Compounds;organoselenides
• Mol File: 5707-04-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 59-62 °C(lit.)
• Boiling Point: 120 °C20 mm Hg(lit.)
• Flash Point: 120°C/20mm
• Appearance: red/crystal
• Vapor Pressure: 0.0722mmHg at 25°C
• Storage Temp.: Store below +30°C.
• Solubility: Soluble in methanol.
• Sensitive: Moisture Sensitive
• Stability: Stable, but may be air or moisture sensitive. Incompatible with strong bases, strong oxidizing agents.
• BRN: 1237091
• CAS DataBase Reference: PHENYLSELENENYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLSELENENYL CHLORIDE(5707-04-0)
• EPA Substance Registry System: PHENYLSELENENYL CHLORIDE(5707-04-0)

Safety Data

• Hazard Codes: T,N
• Statements: 23/25-33-50/53
• Safety Statements: 20/21-28-45-60-61
• RIDADR: UN 2928 6.1/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 5707-04-0(Hazardous Substances Data)

Usage

Chemical Properties

crystalline solid

Uses

Phenylselenenyl chloride is used in the preparation of (cyclobut-1-enylselanyl)benzene. It is an important versatile reagent used in organic synthesis. Further, it serves as a useful synthon for 2-amino alcohols.

General Description

Phenylselenyl chloride is a synthon for 2-amino alcohols. It is a versatile reagent in organic synthesis.

Purification Methods

Purify it by distillation in a vacuum, and recrystallisation (orange needles) from hexane [Foster J Am Chem Soc 55 822 1933, Foster et al. Recl Trav Chim, Pays-Bas 53 405, 408 1934, Behaghel & Seibert Chem Ber 66 714 1933]. [Beilstein 6 III 1110.] HIGHLY TOXIC.

InChI:InChI=1/C6H5ClSe/c7-8-6-4-2-1-3-5-6/h1-5H

Synthetic route

diphenyl diselenide (1666-13-3) + phenylselenium trichloride (42572-42-9) → Phenylselenyl chloride (5707-04-0)

Conditions	Yield
In tetrachloromethane at 20℃; for 2h;	100%

diphenyl diselenide (1666-13-3) → Phenylselenyl chloride (5707-04-0)

Conditions	Yield
Stage #1: diphenyl diselenide With thionyl chloride In tetrachloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: In tetrachloromethane at -20℃; for 2h; Inert atmosphere;	94%
With (Dichloroiodo)benzene In hexane at 20℃; for 0.333333h; Darkness;	82%
With (Dichloroiodo)benzene In hexane at 20℃; for 0.333333h;	82%

chloroform (67-66-3) + diphenyl diselenide (1666-13-3) → Phenylselenyl chloride (5707-04-0)

phenylselenium trichloride (42572-42-9) → Phenylselenyl chloride (5707-04-0)

Conditions	Yield
at 170℃; unter vermindertem Druck;

ethyl-dichloro-phenyl-λ4-selane → Phenylselenyl chloride (5707-04-0) + chloroethane (75-00-3)

Conditions	Yield
at 80℃;

N-phenyldichloroselenobenzeneseleninimidoyl chloride (78489-00-6) → Phenylselenyl chloride (5707-04-0) + phenylselenium trichloride (42572-42-9)

Conditions	Yield
at 20℃; for 24h; Product distribution;	A 75 % Turnov. B 70 % Turnov.

C12H10Cl2N2SSe2 (1352563-37-1) → Phenylselenyl chloride (5707-04-0)

Conditions	Yield
at 70℃;

Benzeneselenol (645-96-5) → Phenylselenyl chloride (5707-04-0)

Conditions	Yield
With N-chloro-succinimide In nitromethane at 20℃; for 0.5h; Sealed tube;

methanol (67-56-1) + Phenylselenyl chloride (5707-04-0) + (Z)-Cyclooctene (931-88-4, 931-87-3) → trans-1-phenylseleno-2-methoxycyclooctane (73090-30-9)

Conditions	Yield
at 25℃;	100%

norborn-2-ene (498-66-8) + Phenylselenyl chloride (5707-04-0) → endo-3-chloro-exo-2-phenylselenobicyclo<2.2.1>heptane (70303-01-4)

Conditions	Yield
In dichloromethane	100%
In water; acetonitrile for 24h; Ambient temperature;	84%
In dichloromethane at 25℃;	100 % Spectr.

5-Hexen-1-ol (821-41-0) + Phenylselenyl chloride (5707-04-0) → (2-(phenylselanylmethyl)oxane) (75526-73-7)

Conditions	Yield
With pyridine In dichloromethane at 20℃;	100%
With zinc(II) chloride In dichloromethane at 20℃;	100%
With silver(l) oxide In dichloromethane at 20℃;	100%

Phenylselenyl chloride (5707-04-0) + (Z)-Cyclooctene (931-88-4, 931-87-3) → (+/-)-rel-((1RS,2SR)-2-chlorocyclooctyl)phenylselenide

Conditions	Yield
In dichloromethane at 25℃;	100%
In dichloromethane at 0 - 20℃; Inert atmosphere;

Phenylselenyl chloride (5707-04-0) + n-Pent-4-enyl alcohol (821-09-0) → 2-(phenylselanylmethyl)oxolane (65539-72-2)

Conditions	Yield
With pyridine In dichloromethane at 20℃;	100%
With silver(l) oxide In dichloromethane at 20℃;	99%
at 20℃; for 0.116667h; Ionic liquid;	95%

Phenylselenyl chloride (5707-04-0) + 4-cycloheptene-1-carboxylic acid (1614-73-9) → (1α,4α,5α)-4-(phenylseleno)-6-oxabicyclo<3.2.2>nonan-7-one (63048-50-0)

Conditions	Yield
With base In dichloromethane at -78 - 25℃; Product distribution; Mechanism; phenylselenolactonizations of unsaturated substrates (SN2 reactions);	100%
With base In dichloromethane at -78 - 25℃;	100%

Phenylselenyl chloride (5707-04-0) + 4-methyl-4-penten-1-ol (22508-64-1) → 2-Methyl-2-phenylselanylmethyl-tetrahydro-furan (114524-28-6)

Conditions	Yield
With silver(l) oxide In dichloromethane at 20℃;	100%
In dichloromethane at -78℃; for 2h;	93%

Phenylselenyl chloride (5707-04-0) + 2,6-dimethyl-hept-6-en-2-ol (32779-58-1) → 2,6,6-trimethyl-2-(phenylselenomethyl)tetrahydropyran (114524-35-5)

Conditions	Yield
With pyridine In dichloromethane at 20℃;	100%
With silver(l) oxide In dichloromethane at 20℃;	96%
In dichloromethane at -78℃; for 2h;	73%

Phenylselenyl chloride (5707-04-0) + 2-diazo-1-(4-methylphenyl)ethanone (17263-64-8) → α-chloro-α-phenylselenomethyl p-tolyl ketone (75608-70-7)

Conditions	Yield
In dichloromethane for 0.5h; Ambient temperature;	100%
In dichloromethane Ambient temperature; Yield given;

Phenylselenyl chloride (5707-04-0) + 1-diazo-3-phenyl-2-propanone (4250-02-6) → benzyl α-chloro-α-phenylselenomethyl ketone (75608-71-8)

Conditions	Yield
In dichloromethane for 0.5h; Ambient temperature;	100%
In dichloromethane Ambient temperature;

Phenylselenyl chloride (5707-04-0) + (S)-1-phenyl-ethylamine (2627-86-3) → N-<(S)-1-Phenylethyl>benzeneselenamide (101685-17-0)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; for 2h;	100%

Phenylselenyl chloride (5707-04-0) + (S)-1-(1-Naphthyl)ethylamine (10420-89-0) → N-<(S)-1-(1-Naphthyl)-ethyl>benzeneselenamide (101685-18-1)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; for 2h;	100%

Phenylselenyl chloride (5707-04-0) + N,N,N'-tris(trimethylsilyl)benzamidine (24261-90-3) → diphenyl diselenide (1666-13-3) + C26H20N4Se2 (127666-88-0, 136276-66-9)

Conditions	Yield
In dichloromethane at 23℃; for 3h;	A 100% B 55%

Phenylselenyl chloride (5707-04-0) + potassium trinitromethanide (14268-23-6) → phenyl trinitromethyl selenide (78743-52-9)

Conditions	Yield
In dichloromethane at 0℃; for 1.5h;	100%

Phenylselenyl chloride (5707-04-0) + 2-(1,1-dimethylbut-3-enyl)oxazoline (104515-33-5) → 1-(2-Chloro-ethyl)-3,3-dimethyl-5-phenylselanylmethyl-pyrrolidin-2-one (107515-52-6)

Conditions	Yield
In acetonitrile for 12h; Ambient temperature;	100%

Phenylselenyl chloride (5707-04-0) + 2,3,6-trimethyl-7-octen-3-ol (118989-21-2) → 6-isopropyl-3,6-dimethyl-2-(phenylselenomethyl)tetrahydropyran (118989-25-6)

Conditions	Yield
With pyridine In dichloromethane at 20℃;	100%
With silver(l) oxide In dichloromethane at 20℃;	97%
In dichloromethane at -78℃; for 2h;	66%

Phenylselenyl chloride (5707-04-0) + (2aR,5aR,8aR,8bR)-3-(2-Hydroxy-ethoxy)-6,6,8b-trimethyl-2a,5,5a,6,7,8,8a,8b-octahydro-naphtho[1,8-bc]furan-2-one → C22H28O4Se

Conditions	Yield
With N,N-diethyl-N-isopropylamine In dichloromethane at 25℃; for 0.5h;	100%

Phenylselenyl chloride (5707-04-0) + 1-((1S,5S,10S,13R)-10,13-Dimethyl-17-octyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl)-2-methyl-isourea → 1-((1R,2S,3S,5S,10S,13R)-3-Hydroxy-10,13-dimethyl-17-octyl-2-phenylselanyl-hexadecahydro-cyclopenta[a]phenanthren-1-yl)-2-methyl-isourea

Conditions	Yield
With silica gel In chloroform at 25℃; for 16h;	100%

Phenylselenyl chloride (5707-04-0) + 1,4-Dichloro-2-butyne (821-10-3) → (E)-2-(Phenylseleno)-1,3,4-trichlorobut-2-ene (85972-08-3)

Conditions	Yield
In acetonitrile at 25℃; for 20h;	100%

Phenylselenyl chloride (5707-04-0) + ethyl (2S)-pyrrolidine-2-carboxylate (5817-26-5) → N-Benzeneselenenyl-(S)-proline ethyl ester (101685-19-2)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; for 2h;	100%

Phenylselenyl chloride (5707-04-0) + methyl 2-oxocyclopentane-1-carboxylate (10472-24-9) → methyl 2-oxo-1-(phenylselanyl)cyclopentane-1-carboxylate (105405-22-9)

Conditions	Yield
With pyridine In dichloromethane 1.) 0 deg C, 90 min, 2.) up to RT;	100%
With pyridine In dichloromethane	10.1 g
With pyridine In dichloromethane at 0℃;

Phenylselenyl chloride (5707-04-0) + 3-methyl-2-buten-1-ol (556-82-1) → 3-methyl-2-(phenylselenyl)-1,3-butanediol (99018-46-9)

Conditions	Yield
With water In acetonitrile at 20℃; for 24h;	100%
In water; acetonitrile for 2h; Ambient temperature;	86%

Phenylselenyl chloride (5707-04-0) + 2-methyl-3-buten-2-ol (115-18-4) → 3-methyl-2-(phenylselenyl)-1,3-butanediol (99018-46-9)

Conditions	Yield
In water; acetonitrile for 2h; Ambient temperature;	100%
With water In acetonitrile at 20℃; for 24h;	86%

Phenylselenyl chloride (5707-04-0) + Thallous Phenyl Selenide (72017-00-6) → diphenyl diselenide (1666-13-3) + thallous chloride

Conditions	Yield
In diethyl ether for 0.00833333h; Ambient temperature;	A 100% B n/a

Phenylselenyl chloride (5707-04-0) + (5R)-1-Benzoyl-5-benzyl-3-[(4E,6S,8E,10E,12E)-4,6,12-trimethyl-1-oxotetradecatetra-4,8,10,12-enyl]pyrrolidin-2-one (129056-32-2) → (5R)-1-Benzoyl-5-benzyl-3-phenylseleno-3-[(4E,6S,8E,10E,12E)-4,6,12-trimethyl-1-oxotetradecatetra-4,8,10,12-enyl]pyrrolidin-2-one (259136-36-2)

Conditions	Yield
Stage #1: (5R)-1-Benzoyl-5-benzyl-3-[(4E,6S,8E,10E,12E)-4,6,12-trimethyl-1-oxotetradecatetra-4,8,10,12-enyl]pyrrolidin-2-one With lithium hexamethyldisilazane In tetrahydrofuran; hexane at -70℃; for 1h; Metallation; Stage #2: Phenylselenyl chloride In tetrahydrofuran; hexane at -70℃; for 2h; Phenylselenenylation;	100%

Phenylselenyl chloride (5707-04-0) + 1-(2-(methylthio)phenyl)-2-phenylacetylene (312612-67-2) → 2-phenyl-3-(phenylselanyl)benzo[b]thiophene

Conditions	Yield
In dichloromethane at 20℃; for 0.166667h;	100%
In dichloromethane at 25℃; for 0.166667h;	100%

Phenylselenyl chloride (5707-04-0) + trimethyl{[2-(methylsulfanyl)phenyl]ethynyl}silane (415680-02-3) → 3-(phenylselenenyl)-2-trimethylsilylbenzo[b]thiophene

Conditions	Yield
In dichloromethane at 25℃; for 0.166667h;	100%
In dichloromethane at 20℃; Inert atmosphere;	100%
In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;	100%

Phenylselenyl chloride (5707-04-0) + 6-methylhept-6-en-2-ol (32779-60-5) → 2,6-Dimethyl-2-phenylselanylmethyl-tetrahydro-pyran (114524-34-4)

Conditions	Yield
With pyridine In dichloromethane at 20℃;	100%
With silver(l) oxide In dichloromethane at 20℃;	100%

Phenylselenyl chloride (5707-04-0) + terpineol (98-55-5) → 1,3,3-trimethyl-6-(phenylseleno)-2-oxabicyclo[2.2.2]octane (92691-96-8)

Conditions	Yield
With pyridine In dichloromethane at 20℃;	100%
With triethylamine In dichloromethane Reagent/catalyst;	100%
With pyridine at 20℃; for 2h; Ionic liquid;	71%

Upstream product

• 1666-13-3 diphenyl diselenide 
• 42572-42-9 phenylselenium trichloride 
• 645-96-5 Benzeneselenol 
• 1352563-37-1 C₁₂H₁₀Cl₂N₂SSe₂ 
• 78489-00-6 N-phenyldichloroselenobenzeneseleninimidoyl chloride 
• 67-66-3 chloroform 

Downstream Products

• 61759-13-5 1-(phenylselanyl)propan-2-one 
• 50630-26-7 2-Chlor-2-methyl-propyl-1-benzolselenid 
• 19324-75-5 2-chloro-1-methylcylohexanol 
• 64371-64-8 (+/-)-2t-chloro-2c-methyl-cyclohexan-r-ol 
• 78488-61-6 N-(phenyldichloroseleno)morpholine 
• 100068-32-4 3-Phenylselanyl-cyclohex-1-enecarboxylic acid methyl ester 
• 93426-68-7 4-(Phenylseleno)-5-methyl-7-ethyl-6,8-dioxabicyclo<3.2.1>octane 
• 67140-46-9 (3aR,7aS)-3a-Phenylselanyl-octahydro-benzo[b]thiophene 
• 126641-76-7 4-chloro-6-methoxy-2H-pyran-3(6H)-one 
• 131262-63-0 4-Benzeneselenenyl-6-methoxy-2,3-dihydro-6H-pyran-3-one 
• 71404-67-6 4-(phenylseleno)-6-oxabicyclo<3.2.1>octan-7-one 
• 85738-68-7 2,4-dimethyl-2-selenophenyl-8-oxabicyclo<3.2.1>oct-6-en-3-one 
• 59853-64-4 2-Phenylselanyl-cyclopentadecanone 
• 91914-36-2 11α-phenylseleno-7,8αH-eudesm-4-en-12,8-olide 

Relevant articles and documents

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