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40817-08-1

Basic Information
CAS No.: 40817-08-1
Name: 4-Cyano-4'-pentylbiphenyl
Article Data: 13
Molecular Structure:
Molecular Structure of 40817-08-1 (4-Cyano-4'-pentylbiphenyl)
Formula: C18H19N
Molecular Weight: 249.356
Synonyms: 4-Amyl-4'-cyanobiphenyl;4-Cyano-4'-n-pentyl-1,1'-biphenyl;4-Cyano-4'-n-pentylbiphenyl;4-Cyano-4'-n-pentyldiphenyl;4-Cyano-4'-pentyl-1,1'-biphenyl;4-Pentyl-4'-cyanobiphenyl;4-n-Amyl-4'-cyanobiphenyl;4-n-Pentyl-4'-cyanobiphenyl;4'-Amyl-4-cyanobiphenyl;4'-Cyano-4-pentylbiphenyl;4'-Pentyl-4-biphenylcarbonitrile;4'-Pentyl-4-cyanobiphenyl;4'-n-Pentyl-4-cyanobiphenyl;p'-Cyano-p-pentylbiphenyl;
EINECS: 255-093-2
Density: 1.03 g/cm3
Melting Point: 34 °C
Boiling Point: 361.634 °C at 760 mmHg
Flash Point: 193.491 °C
Solubility: insoluble in water
Appearance: white to light yellow crystal
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22-36/37/38
Safety: 23-26-28-36-36/37/39
Transport Information: UN 3276
PSA: 23.79000
LogP: 4.95798
Synthetic route
544-92-3

copper(I) cyanide

69971-79-5

4-iodoo-4'-n-pentylbiphenyl

40817-08-1

4-cyano-4'-pentyl-1,1'-biphenyl

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 6h; Heating;90.5%
63619-59-0

4-(4-pentylphenyl)bromobenzene

40817-08-1

4-cyano-4'-pentyl-1,1'-biphenyl

Conditions
ConditionsYield
Stage #1: 4-(4-pentylphenyl)bromobenzene With iodine; magnesium In tetrahydrofuran at 70℃;
Stage #2: With N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 2h;
Stage #3: With ammonia; iodine In tetrahydrofuran; water at 20℃; for 2h;
80%
623-00-7

4-bromobenzenecarbonitrile

159259-35-5

(dichloro)(ethyl)<4-(pentyl)phenyl>silane

40817-08-1

4-cyano-4'-pentyl-1,1'-biphenyl

Conditions
ConditionsYield
With potassium fluoride; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 120℃;73%
80563-32-2

4-formyl-4'-n-pentylbiphenyl oxime

40817-08-1

4-cyano-4'-pentyl-1,1'-biphenyl

Conditions
ConditionsYield
With acetic anhydride for 2h; Heating;73%
630-18-2

tert-butyl isocyanide

63619-59-0

4-(4-pentylphenyl)bromobenzene

40817-08-1

4-cyano-4'-pentyl-1,1'-biphenyl

Conditions
ConditionsYield
Stage #1: 4-(4-pentylphenyl)bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -50℃; for 0.5h; Inert atmosphere;
Stage #2: tert-butyl isocyanide In tetrahydrofuran; hexane at -50 - 20℃; for 0.5h; Inert atmosphere; Further stages;
73%
63619-59-0

4-(4-pentylphenyl)bromobenzene

68-12-2, 33513-42-7

N,N-dimethyl-formamide

40817-08-1

4-cyano-4'-pentyl-1,1'-biphenyl

Conditions
ConditionsYield
Stage #1: 4-(4-pentylphenyl)bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 2h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 2h;
Stage #3: With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; ammonia In tetrahydrofuran; water at 20℃; for 2h;
72%
5807-02-3

4-morpholinoacetonitrile

4'-pentyl-[1,1'-biphenyl]-4-yl dimethylcarbamate

40817-08-1

4-cyano-4'-pentyl-1,1'-biphenyl

Conditions
ConditionsYield
With potassium phosphate; nickel dibromide; zinc; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 150℃; for 18h; Inert atmosphere; Glovebox; Sealed tube;68%
623-00-7

4-bromobenzenecarbonitrile

121219-12-3

(4-pentylphenyl)boronic acid

40817-08-1

4-cyano-4'-pentyl-1,1'-biphenyl

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In 1,4-dioxane; water at 100℃; for 1h; Suzuki-Miyaura Coupling; Inert atmosphere;26%
92-52-4

biphenyl

40817-08-1

4-cyano-4'-pentyl-1,1'-biphenyl

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: AlCl3 / CH2Cl2 / 5 h / Ambient temperature
2: 1) hydrazine hydrate, 2) KOH / 1) diethylene glycol, 130 deg C, 1 h, 2) diethylene glycol, 130 deg C, 2 h, then 160 deg C, 3 h
3: 1) TiCl4, 2) hydroxylamine hydrochloride, pyridine / 1) CH2Cl2, 0 deg C, 30 min, 2) ethanol, reflux, 2 h
4: 73 percent / acetic anhydride / 2 h / Heating
View Scheme
42916-73-4

1-[1,1'-biphenyl]-4-yl-1-pentanone

40817-08-1

4-cyano-4'-pentyl-1,1'-biphenyl

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1) hydrazine hydrate, 2) KOH / 1) diethylene glycol, 130 deg C, 1 h, 2) diethylene glycol, 130 deg C, 2 h, then 160 deg C, 3 h
2: 1) TiCl4, 2) hydroxylamine hydrochloride, pyridine / 1) CH2Cl2, 0 deg C, 30 min, 2) ethanol, reflux, 2 h
3: 73 percent / acetic anhydride / 2 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 145.6 g / 80percent hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 3 h / 130 °C
2: 71.9 percent / 98percent H2SO4, HIO3, I2 / acetic acid; H2O; CCl4 / 10 h / 80 °C
3: 90.5 percent / dimethylformamide / 6 h / Heating
View Scheme
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Specification

The 4-Cyano-4'-N-pentylbiphenyl, with the CAS registry number 40817-08-1, is also known as 4'-Pentyl-4-biphenylcarbonitrile. It belongs to the product categories of Biphenyl & Diphenyl Ether; Biphenyls (Building Blocks for Liquid Crystals); Building Blocks for Liquid Crystals; Cyanobiphenyls & Analogs (Liquid Crystals); Functional Materials; Liquid Crystals & Related Compounds; Liquid Crystals; Nematic; Organic Electronics and Photonics. Its EINECS registry number is 255-093-2. This chemical's molecular formula is C18H19N and molecular weight is 249.35. What's more, its IUPAC name is called 4-(4-Pentylphenyl)benzonitrile. It should be stored in a cool, dry and well-ventilated place. This chemical is a commonly used as nematic liquid crystal.

Physical properties about 4-Cyano-4'-N-pentylbiphenyl are: (1)ACD/LogP: 6.094; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.09; (4)ACD/LogD (pH 7.4): 6.09; (5)ACD/BCF (pH 5.5): 25210.27; (6)ACD/BCF (pH 7.4): 25210.27; (7)ACD/KOC (pH 5.5): 49230.53; (8)ACD/KOC (pH 7.4): 49230.53; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 23.79 Å2; (13)Index of Refraction: 1.569; (14)Molar Refractivity: 79.174 cm3; (15)Molar Volume: 241.498 cm3; (16)Polarizability: 31.387×10-24 cm3; (17)Surface Tension: 44.47 dyne/cm; (18)Density: 1.033 g/cm3; (19)Flash Point: 193.491 °C; (20)Enthalpy of Vaporization: 60.749 kJ/mol; (21)Boiling Point: 361.634 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of 4-Cyano-4'-N-pentylbiphenyl: this chemical can be prepared by 4-formyl-4'-n-pentylbiphenyl oxime. The reaction occurs with reagent acetic anhydride and other condition of heating for 2 hours. The yield is 73 %.

4-Cyano-4'-N-pentylbiphenyl can be prepared by 4-formyl-4'-n-pentylbiphenyl oxime.

Uses of 4-Cyano-4'-N-pentylbiphenyl: it is used to produce other chemicals. For example, it can produce 4'-pentylbiphenyl-4-carboxylic acid. This reaction needs reagent H2SO4 and solvent acetic acid at temperature of 120 °C. The yield is 88 %.

4-Cyano-4'-N-pentylbiphenyl can produce 4'-pentylbiphenyl-4-carboxylic acid.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system. It may cause damage to health by inhalation, in contacting with skin and if swallowed. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: N#Cc2ccc(c1ccc(cc1)CCCCC)cc2
(2) InChI: InChI=1S/C18H19N/c1-2-3-4-5-15-6-10-17(11-7-15)18-12-8-16(14-19)9-13-18/h6-13H,2-5H2,1H3
(3) InChIKey: HHPCNRKYVYWYAU-UHFFFAOYSA-N

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