Product Name

  • Name

    4-CYANO-4-(THIOBENZOYLTHIO)PENTANOIC ACID

  • EINECS
  • CAS No. 201611-92-9
  • Article Data21
  • CAS DataBase
  • Density 1.309 g/cm3
  • Solubility
  • Melting Point 94-98°C
  • Formula C13H13NO2S2
  • Boiling Point 473.01 °C at 760 mmHg
  • Molecular Weight 279.384
  • Flash Point 239.868 °C
  • Transport Information
  • Appearance
  • Safety 36/37
  • Risk Codes 43
  • Molecular Structure Molecular Structure of 201611-92-9 (4-CYANO-4-(THIOBENZOYLTHIO)PENTANOIC ACID)
  • Hazard Symbols Xi
  • Synonyms 4-(4-Cyanopentanoicacid) dithiobenzoate;4-Cyano-4-(thiobenzoylthio)pentanoic acid;4-Cyano-4-[(thiobenzoyl)sulfanyl]pentanoic acid;6-Phenyl-6-thioxo-5-thia-4-cyano-4-methylhexanoic acid;
  • PSA 118.48000
  • LogP 3.24238

Synthetic route

bis(thiobenzoyl) disulfide
5873-93-8

bis(thiobenzoyl) disulfide

4,4'-dicyano-4,4'-azo-di-valeric acid
2638-94-0

4,4'-dicyano-4,4'-azo-di-valeric acid

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
In ethyl acetate at 85℃; for 12h; Inert atmosphere;75%
In ethyl acetate for 18h; Heating;68%
In ethyl acetate Reflux;65%
4,4'-dicyano-4,4'-azo-di-valeric acid
2638-94-0

4,4'-dicyano-4,4'-azo-di-valeric acid

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
With pyrrol-N-thiocarbonyl disulfides In ethyl acetate for 20h;59%
Multi-step reaction with 3 steps
1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 20 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
3: ethyl acetate / 20 h / 80 °C / Inert atmosphere
View Scheme
polymer, obtained by reversible addition fragmentation chain-transfer; monomer(s): 4-cyanopentanoic acid dithiobenzoate

polymer, obtained by reversible addition fragmentation chain-transfer; monomer(s): 4-cyanopentanoic acid dithiobenzoate

4,4'-dicyano-4,4'-azo-di-valeric acid
2638-94-0

4,4'-dicyano-4,4'-azo-di-valeric acid

A

polymer, Mn (SEC) = 23500, PDI (SEC) = 1.05; monomer(s): 4-cyanopentanoic acid dithiobenzoate; 4,4'-azobis(4-cyanopentanoic acid)

polymer, Mn (SEC) = 23500, PDI (SEC) = 1.05; monomer(s): 4-cyanopentanoic acid dithiobenzoate; 4,4'-azobis(4-cyanopentanoic acid)

B

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
In methanol at 80℃; for 3h;A 82%
B n/a
...Expand
dithiobenzoic acid
121-68-6

dithiobenzoic acid

4,4'-dicyano-4,4'-azo-di-valeric acid
2638-94-0

4,4'-dicyano-4,4'-azo-di-valeric acid

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
Stage #1: dithiobenzoic acid With iodine; dimethyl sulfoxide In ethyl acetate for 10h;
Stage #2: 4,4'-dicyano-4,4'-azo-di-valeric acid In ethyl acetate for 18h; Heating;		44%
benzyl chloride
100-44-7

benzyl chloride

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium methylate; sulfur / methanol / 10 h / Inert atmosphere; Reflux
2.1: sodium hydroxide / water
2.2: 1 h
3.1: ethyl acetate / 18 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: sodium; sulfur / methanol / 10.25 h / 65 °C
2: iodine / dimethyl sulfoxide; ethyl acetate / 20 °C / Darkness
3: ethyl acetate / 16 h / 77 °C
View Scheme
Multi-step reaction with 3 steps
1: sulfur; sodium methylate / methanol / 10 h / Reflux; Inert atmosphere
2: potassium hexacyanoferrate (III) / 1 h
3: ethyl acetate / 18 h / Reflux
View Scheme
dithiobenzoic acid sodium salt
3682-36-8

dithiobenzoic acid sodium salt

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium ferricyanide / H2O / 1 h / 20 °C
2: ethyl acetate / 28.5 h / 70 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium hexacyanoferrate (III) / 1 h
2: ethyl acetate / 18 h / Reflux
View Scheme
benzyl chloride
100-44-7

benzyl chloride

N,N-diethyl-glycine-<4-hydroxy-anilide>

N,N-diethyl-glycine-<4-hydroxy-anilide>

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfur; MeONa / methanol / 10 h / 70 °C
2: potassium ferricyanide / H2O / 1 h / 20 °C
3: ethyl acetate / 28.5 h / 70 °C
View Scheme
dithiobenzoic acid
121-68-6

dithiobenzoic acid

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iodine; dimethyl sulfoxide / ethanol / 2 h / 20 °C
2: ethyl acetate / 20 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water
1.2: 1 h
2.1: ethyl acetate / 18 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: iodine / dimethyl sulfoxide; ethyl acetate / 20 °C / Darkness
2: ethyl acetate / 16 h / 77 °C
View Scheme
bis(thiobenzoyl) disulfide
5873-93-8

bis(thiobenzoyl) disulfide

C48H54N10O6
1268268-75-2

C48H54N10O6

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
In ethyl acetate at 80℃; for 20h; Inert atmosphere;34%
bis(dithiobenzoyl) disulfide

bis(dithiobenzoyl) disulfide

4,4'-dicyano-4,4'-azo-di-valeric acid
2638-94-0

4,4'-dicyano-4,4'-azo-di-valeric acid

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 28h; Reflux;
bromobenzene
108-86-1

bromobenzene

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: iodine; magnesium / tetrahydrofuran / 1 h
1.2: 2 h / 0 °C
2.1: iodine; dimethyl sulfoxide / ethanol / 2 h / 20 °C
3.1: ethyl acetate / 20 h / 80 °C / Inert atmosphere
View Scheme
chloride of 4,4'-azo-bis(4-cyanopentanoic) acid chloride
17170-81-9

chloride of 4,4'-azo-bis(4-cyanopentanoic) acid chloride

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
2: ethyl acetate / 20 h / 80 °C / Inert atmosphere
View Scheme
N,N-Dimethylacrylamide
2680-03-7

N,N-Dimethylacrylamide

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

poly(N,N-dimethylacrylamide), Mn 8200, Mw/Mn 1.08, product of RAFT polymerization with 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate; monomer(s): N,N-dimethylacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate

poly(N,N-dimethylacrylamide), Mn 8200, Mw/Mn 1.08, product of RAFT polymerization with 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate; monomer(s): N,N-dimethylacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate

Conditions
ConditionsYield
With hydrogenchloride; 4,4'-dicyano-4,4'-azo-di-valeric acid In acetate buffer at 80℃; for 0.333333h; pH=5;96.73%
4-pyrenylbutanol
67000-89-9

4-pyrenylbutanol

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

4-cyano-4-methyl-4-thiobenzoylsulfanyl-butyric acid 4-pyren-1-yl-butyl ester
1048735-14-3

4-cyano-4-methyl-4-thiobenzoylsulfanyl-butyric acid 4-pyren-1-yl-butyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane at 0 - 20℃;95%
4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-bromopropyl 4-((benzenethiocarbonyl)thio)-4-cyanopentanoate
1414117-60-4

3-bromopropyl 4-((benzenethiocarbonyl)thio)-4-cyanopentanoate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 18h; Inert atmosphere;93.9%
poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

triethylamine
121-44-8

triethylamine

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

polymer, molecular weight distribution = 1.12, Mn = 8200

polymer, molecular weight distribution = 1.12, Mn = 8200

Conditions
ConditionsYield
With 4,4'-dicyano-4,4'-azo-di-valeric acid In water at 75℃; for 12h;93.2%
...Expand
1-indene
95-13-6

1-indene

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

C22H21NO2S2

C22H21NO2S2

Conditions
ConditionsYield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III) In dimethyl sulfoxide at 20℃; for 36h; Inert atmosphere; Irradiation; Sealed tube;93%
acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

C17H19NO4S2

C17H19NO4S2

Conditions
ConditionsYield
With pheophorbide A In dimethyl sulfoxide at 20℃; for 20h; Sealed tube; Inert atmosphere; Irradiation;92%
bis(2-hydroxyethyl) disulfide
1892-29-1

bis(2-hydroxyethyl) disulfide

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

C30H32N2O4S6

C30H32N2O4S6

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;83.9%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;65.3%
3,3,4,4-tetrafluoro-butane sultone
1384119-19-0

3,3,4,4-tetrafluoro-butane sultone

5-phenyl-5H-dibenzo[b,d]thiophen-5-ium bromide

5-phenyl-5H-dibenzo[b,d]thiophen-5-ium bromide

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

C17H16F4NO5S3(1-)*C18H13S(1+)

C17H16F4NO5S3(1-)*C18H13S(1+)

Conditions
ConditionsYield
Stage #1: 4-cyano-4-(thiobenzoylthio)pentanoic acid With potassium hydride In tetrahydrofuran Inert atmosphere;
Stage #2: 3,3,4,4-tetrafluoro-butane sultone In tetrahydrofuran at 20℃; for 2h;
Stage #3: 5-phenyl-5H-dibenzo[b,d]thiophen-5-ium bromide In dichloromethane; water at 20℃; for 12h;		83.7%
Stage #1: 4-cyano-4-(thiobenzoylthio)pentanoic acid With potassium hydride In tetrahydrofuran for 0.0833333h; Inert atmosphere;
Stage #2: 3,3,4,4-tetrafluoro-butane sultone In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
Stage #3: 5-phenyl-5H-dibenzo[b,d]thiophen-5-ium bromide In water at 20℃; Inert atmosphere;		83.7%
...Expand
2-nitro-5-(2-propargyloxy)benzyl alcohol
1144029-01-5

2-nitro-5-(2-propargyloxy)benzyl alcohol

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

2-nitro-5-(2-propynyloxy)benzyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate
1318075-32-9

2-nitro-5-(2-propynyloxy)benzyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h;83%
2-(2-(2-(2-(pyridin-2-yldisulfanyl)ethoxy)ethoxy)ethoxy)ethan-1-ol
851961-99-4

2-(2-(2-(2-(pyridin-2-yldisulfanyl)ethoxy)ethoxy)ethoxy)ethan-1-ol

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

C26H32N2O5S4

C26H32N2O5S4

Conditions
ConditionsYield
Stage #1: 2-(2-(2-(2-(pyridin-2-yldisulfanyl)ethoxy)ethoxy)ethoxy)ethan-1-ol; 4-cyano-4-(thiobenzoylthio)pentanoic acid With dmap In dichloromethane at 0℃; for 0.5h;
Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h;		81%
4,4'-dicyano-4,4'-azo-di-valeric acid
2638-94-0

4,4'-dicyano-4,4'-azo-di-valeric acid

2'-(2''-methylacryolyloxy)ethyl-β-D-galactopyranoside
21698-14-6

2'-(2''-methylacryolyloxy)ethyl-β-D-galactopyranoside

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

poly[2-(β-D-galactosyloxy)ethyl methacrylate], Mn (SEC) 24100, PDI (SEC) 1.09; monomer(s): 2-(β-D-galactosyloxy)ethyl methacrylate; 4,4-azobis(4-cyanopentanoic acid); 4-(cyanopentanoic acid)-4-dithiobenzoate

poly[2-(β-D-galactosyloxy)ethyl methacrylate], Mn (SEC) 24100, PDI (SEC) 1.09; monomer(s): 2-(β-D-galactosyloxy)ethyl methacrylate; 4,4-azobis(4-cyanopentanoic acid); 4-(cyanopentanoic acid)-4-dithiobenzoate

Conditions
ConditionsYield
In ethanol; water at 70℃; for 3h;80%
...Expand
propargyl alcohol
107-19-7

propargyl alcohol

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

4-cyano-4-((thiobenzoyl)sulfanyl)pentanoic propargyl ester
1075252-15-1

4-cyano-4-((thiobenzoyl)sulfanyl)pentanoic propargyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; Steglich Esterification;80%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;75%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 19h;62%
2-methyl-acrylic acid 3-dimethylamino-propyl amide
5205-93-6

2-methyl-acrylic acid 3-dimethylamino-propyl amide

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

poly(N-[3-(dimethylamino)propyl]methacrylamide), terminated with 4-carboxy-2-cyanobutyl-2-yl and thiobenzoylsulfanyl units, product of RAFT polymerization; monomer(s): N-[3-(dimethylamino)propyl]methacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate

poly(N-[3-(dimethylamino)propyl]methacrylamide), terminated with 4-carboxy-2-cyanobutyl-2-yl and thiobenzoylsulfanyl units, product of RAFT polymerization; monomer(s): N-[3-(dimethylamino)propyl]methacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate

Conditions
ConditionsYield
With hydrogenchloride; 4,4'-dicyano-4,4'-azo-di-valeric acid In acetate buffer at 70℃; for 1h; pH=5;78.77%
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

pentafluorophenyl 4-cyano-4-((phenylcarbonothioyl)thio)pentanoate
1160527-68-3

pentafluorophenyl 4-cyano-4-((phenylcarbonothioyl)thio)pentanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 2h;76%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;76%
With dmap; diisopropyl-carbodiimide In dichloromethane at 0℃;30%
2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

2-(methacryloyloxy)ethyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate
1361105-67-0

2-(methacryloyloxy)ethyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In toluene at 20℃; for 12h;75%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 24h; Inert atmosphere;69.2%
4-(2-hydroxy-ethyl)-10-oxa-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
32620-90-9

4-(2-hydroxy-ethyl)-10-oxa-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

4-cyano-4-(thiobenzoylthio)pentanoic acid
201611-92-9

4-cyano-4-(thiobenzoylthio)pentanoic acid

C23H22N2O5S2

C23H22N2O5S2

Conditions
ConditionsYield
Stage #1: 4-(2-hydroxy-ethyl)-10-oxa-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione; 4-cyano-4-(thiobenzoylthio)pentanoic acid With dmap; ethyl cyanoglyoxylate-2-oxime In acetonitrile for 0.0833333h; Schlenk technique;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 0 - 20℃; for 18h; Schlenk technique;		73%

Pentanoicacid, 4-cyano-4-[(phenylthioxomethyl)thio]- Specification

The CAS register number of Pentanoicacid, 4-cyano-4-[(phenylthioxomethyl)thio]- is 201611-92-9. It also can be called as 4-Cyano-4-[(phenylcarbonothioyl)sulfanyl]pentanoic acid and the systematic name about this chemical is 4-(benzenecarbonothioylsulfanyl)-4-cyano-pentanoic acid. The molecular formula about this chemical is C13H13NO2S2 and the molecular weight is 279.3778.

Physical properties about Pentanoicacid, 4-cyano-4-[(phenylthioxomethyl)thio]- are: (1)ACD/LogP: 3.82; (2)ACD/LogD (pH 5.5): 2; (3)ACD/LogD (pH 7.4): 1; (4)ACD/BCF (pH 5.5): 17; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 103; (7)ACD/KOC (pH 7.4): 2; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 6; (11)Polar Surface Area: 118.48Å2; (12)Index of Refraction: 1.632; (13)Molar Refractivity: 76.146 cm3; (14)Molar Volume: 213.392 cm3; (15)Polarizability: 30.187x10-24cm3; (16)Surface Tension: 66.207 dyne/cm; (17)nthalpy of Vaporization: 77.542 kJ/mol; (18)Boiling Point: 473.01 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(CCC(=O)O)(C#N)SC(=S)c1ccccc1
(2)InChI: InChI=1/C13H13NO2S2/c1-13(9-14,8-7-11(15)16)18-12(17)10-5-3-2-4-6-10/h2-6H,7-8H2,1H3,(H,15,16)
(3)InChIKey: YNKQCPNHMVAWHN-UHFFFAOYAA
(4)Std. InChI: InChI=1S/C13H13NO2S2/c1-13(9-14,8-7-11(15)16)18-12(17)10-5-3-2-4-6-10/h2-6H,7-8H2,1H3,(H,15,16)
(5)Std. InChIKey: YNKQCPNHMVAWHN-UHFFFAOYSA-N

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