Product Name

  • Name

    4-BROMO-3,5-DIMETHYL-BENZONITRILE

  • EINECS 676-077-5
  • CAS No. 75344-77-3
  • Article Data5
  • CAS DataBase
  • Density 1.446 g/cm3
  • Solubility
  • Melting Point 135-137ºC
  • Formula C9H8BrN
  • Boiling Point 291.049 °C at 760 mmHg
  • Molecular Weight 210.073
  • Flash Point 129.822 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 75344-77-3 (4-BROMO-3,5-DIMETHYL-BENZONITRILE)
  • Hazard Symbols
  • Synonyms 4-Bromo-3,5-dimethylbenzonitrile;4-Bromo-3,5-dimethyl-benzonitrile;
  • PSA 23.79000
  • LogP 2.93758

Synthetic route

4-bromo-3,5-dimethylbenzaldehyde oxime
400822-49-3

4-bromo-3,5-dimethylbenzaldehyde oxime

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

Conditions
ConditionsYield
With carbon disulfide; sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In toluene at 20℃; for 20h;75%
2-bromo-5-(bromomethyl)-1,3-dimethylbenzene
35510-00-0

2-bromo-5-(bromomethyl)-1,3-dimethylbenzene

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

Conditions
ConditionsYield
With ammonium hydroxide; iodine In acetonitrile at 60℃; for 4h; Solvent; Temperature; Inert atmosphere;73.5%
4-bromo-3,5-dimethylbenzaldehyde
400822-47-1

4-bromo-3,5-dimethylbenzaldehyde

A

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

B

4-bromo-3,5-dimethylbenzaldehyde oxime
400822-49-3

4-bromo-3,5-dimethylbenzaldehyde oxime

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In toluene for 2h; Heating;A 39%
B 56%
4-bromo-3,5-dimethylbenzamide
864825-81-0

4-bromo-3,5-dimethylbenzamide

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

Conditions
ConditionsYield
With phosphorus pentachloride
1,4-dibromo-2,6-dimethylbenzene
100189-84-2

1,4-dibromo-2,6-dimethylbenzene

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: nBuLi / diethyl ether; hexane / 0.75 h / -78 °C
1.2: 79 percent / diethyl ether; hexane / -78 - 20 °C
2.1: 39 percent / hydroxylamine hydrochloride; pyridine / toluene / 2 h / Heating
View Scheme
Multi-step reaction with 3 steps
1.1: nBuLi / diethyl ether; hexane / 0.75 h / -78 °C
1.2: 79 percent / diethyl ether; hexane / -78 - 20 °C
2.1: 56 percent / hydroxylamine hydrochloride; pyridine / toluene / 2 h / Heating
3.1: 75 percent / CS2; aq. NaOH; (nBu)4NHSO4 / toluene / 20 h / 20 °C
View Scheme
4-bromo-3,5-dimethylbenzaldehyde
400822-47-1

4-bromo-3,5-dimethylbenzaldehyde

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 56 percent / hydroxylamine hydrochloride; pyridine / toluene / 2 h / Heating
2: 75 percent / CS2; aq. NaOH; (nBu)4NHSO4 / toluene / 20 h / 20 °C
View Scheme
4-bromo-3,5-dimethylbenzoic acid
7697-32-7

4-bromo-3,5-dimethylbenzoic acid

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / Behandeln des erhaltenen Saeurechlorids mit wss. Ammoniak
2: phosphorus (V)-chloride
View Scheme
zinc(II) cyanide
557-21-1

zinc(II) cyanide

4-bromo-3,5-dimethylphenyl trifluoromethanesulfonate
864825-79-6

4-bromo-3,5-dimethylphenyl trifluoromethanesulfonate

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

Conditions
ConditionsYield
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl acetamide; acetonitrile at 50 - 88℃;
2,4,6-trimethylphenyl bromide
576-83-0

2,4,6-trimethylphenyl bromide

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide; dibenzoyl peroxide / 1,2-dichloro-ethane / 2 h / 85 °C
2: ammonium hydroxide; iodine / acetonitrile / 4 h / 60 °C / Inert atmosphere
View Scheme
zinc(II) cyanide
557-21-1

zinc(II) cyanide

2-Bromo-m-xylene
576-22-7

2-Bromo-m-xylene

A

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

B

3-bromo-2,4-dimethylbenzonitrile

3-bromo-2,4-dimethylbenzonitrile

Conditions
ConditionsYield
With 3-(trifluoromethyl)quinoline; palladium diacetate; silver fluoride; N-acetylglycine at 80℃; for 18h; Overall yield = 65 %;
...Expand
4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

4-bromo-3,5-dimethylbenzoic acid
7697-32-7

4-bromo-3,5-dimethylbenzoic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 22h; Reflux;98%
With water; sodium hydroxide In ethanol at 120℃; for 12h; Sealed tube;
With water; sodium hydroxide at 95℃; for 17h;
isopropylboronic acid
80041-89-0

isopropylboronic acid

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

4-isopropyl-3,5-dimethylbenzonitrile

4-isopropyl-3,5-dimethylbenzonitrile

Conditions
ConditionsYield
With potassium phosphate monohydrate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; C20H34O3P2 In toluene at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;96%
2-(3,4,5-trifluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
827614-70-0

2-(3,4,5-trifluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

3',4',5'-trifluoro-2,6-dimethyl-[1,1'-biphenyl]-4-carbonitrile

3',4',5'-trifluoro-2,6-dimethyl-[1,1'-biphenyl]-4-carbonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 85℃; Inert atmosphere;89.2%
mesitylboronic acid
5980-97-2

mesitylboronic acid

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

3,5-dimethyl-4-(2,4',6'-trimethylphenyl)-benzonitrile
76410-97-4

3,5-dimethyl-4-(2,4',6'-trimethylphenyl)-benzonitrile

Conditions
ConditionsYield
With BI-DIME; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere;88%
potassium tert-butyl N-[(difluoroboranyl)methyl]carbamate

potassium tert-butyl N-[(difluoroboranyl)methyl]carbamate

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

(4-cyano-2,6-dimethylbenzyl)carbamic acid tert-butyl ester
1618647-92-9

(4-cyano-2,6-dimethylbenzyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
With methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); caesium carbonate In 1,4-dioxane; water at 110℃; for 16h; Inert atmosphere;86%
4-(diphenylamino)phenylboronic pinacol ester
267221-88-5

4-(diphenylamino)phenylboronic pinacol ester

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

C27H22N2

C27H22N2

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 85℃; for 24h; Inert atmosphere;84%
4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-3,9'-dicarbazole

9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-3,9'-dicarbazole

C39H27N3

C39H27N3

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 85℃; for 24h; Inert atmosphere;79%
9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole
785051-54-9

9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

C27H20N2

C27H20N2

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 85℃; for 18h; Inert atmosphere;78.1%
4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Conditions
ConditionsYield
Stage #1: 4-bromo-3,5-dimethyl benzonitrile With n-butyllithium In tetrahydrofuran; hexane at -100℃; for 1.41667h;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -100 - 20℃;		77%
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -100 °C / Inert atmosphere
1.2: 12 h / -100 - 23 °C / Inert atmosphere
2.1: hydrogenchloride / water; tetrahydrofuran; hexane / 1 h / 23 °C / pH 2 / Inert atmosphere
View Scheme
10-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-10H-phenoxazine

10-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-10H-phenoxazine

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

C27H20N2O

C27H20N2O

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 85℃; for 24h; Inert atmosphere;77%
4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

ethyl (S)-3-((tert-butoxycarbonyl)amino)-3-(2-fluoro-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

ethyl (S)-3-((tert-butoxycarbonyl)amino)-3-(2-fluoro-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

ethyl (S)-3-((tert-butoxycarbonyl)amino)-3-(4'-cyano-4-fluoro-2',5,6'-trimethyl-[1,1'-biphenyl]-3-yl)propanoate

ethyl (S)-3-((tert-butoxycarbonyl)amino)-3-(4'-cyano-4-fluoro-2',5,6'-trimethyl-[1,1'-biphenyl]-3-yl)propanoate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 110℃; for 2h; Inert atmosphere;70%
10-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenoxazine

10-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenoxazine

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

C27H20N2O

C27H20N2O

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 85℃; for 24h; Inert atmosphere;69%
4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile

3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 100℃; Inert atmosphere;65%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 100℃; Inert atmosphere;65%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 90 - 100℃; for 24h; Inert atmosphere;57%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 90 - 100℃; for 24h; Inert atmosphere;57%
4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester
93267-04-0

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-cyano-2,6-dimethylphenyl)propanoate
1227311-10-5

methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-cyano-2,6-dimethylphenyl)propanoate

Conditions
ConditionsYield
Stage #1: N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester With iodine; zinc In N,N-dimethyl-formamide at 20℃; for 0.666667h; Inert atmosphere;
Stage #2: 4-bromo-3,5-dimethyl benzonitrile With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In N,N-dimethyl-formamide at 50℃; Temperature;		50%
Stage #1: N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester With iodine; zinc In N,N-dimethyl acetamide at 21 - 29℃; Inert atmosphere;
Stage #2: 4-bromo-3,5-dimethyl benzonitrile; tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine In N,N-dimethyl acetamide at 35 - 70℃; Product distribution / selectivity; Inert atmosphere;
4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

3,5-dimethyl-4-formylbenzonitrile
157870-16-1

3,5-dimethyl-4-formylbenzonitrile

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane for 1h; Cooling with ether-dry ice;47%
4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

3,5-dimethyl-4-hydroxybenzonitrile
4198-90-7

3,5-dimethyl-4-hydroxybenzonitrile

Conditions
ConditionsYield
With oxygen; triethylamine; sodium iodide In acetonitrile at 32℃; for 24h; Schlenk technique; UV-irradiation;42%
4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene
349666-24-6

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene

3,5-dimethyl-4-(pyren-1-yl)benzonitrile

3,5-dimethyl-4-(pyren-1-yl)benzonitrile

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In toluene for 20h; Suzuki cross-coupling; Heating;28%
4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

4-bromo-3,5-bis(bromomethyl)benzonitrile

4-bromo-3,5-bis(bromomethyl)benzonitrile

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane at 20℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox;25%
5-(tributylstannyl)-[1,2,4]triazolo[1,5-a]pyridine
1332076-55-7

5-(tributylstannyl)-[1,2,4]triazolo[1,5-a]pyridine

4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

3,5-dimethyl-4-{[1,2,4]triazolo[1,5-a]pyridin-5-yl}benzonitrile

3,5-dimethyl-4-{[1,2,4]triazolo[1,5-a]pyridin-5-yl}benzonitrile

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 120℃; for 0.333333h; Stille Cross-Coupling (Migita-Kosugi-Stille Coupling); Inert atmosphere; Sealed tube; Microwave irradiation;20%
4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

4-bromo-N-hydroxy-3,5-dimethyl-benzamidine
1458656-36-4

4-bromo-N-hydroxy-3,5-dimethyl-benzamidine

Conditions
ConditionsYield
With hydroxylamine hydrochloride; triethylamine In ethanol for 4h; Reflux;
4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

3-(4-bromo-3,5-dimethyl-phenyl)-5-methyl-[1,2,4]oxadiazole
1458656-37-5

3-(4-bromo-3,5-dimethyl-phenyl)-5-methyl-[1,2,4]oxadiazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / Reflux
2: 2,4,6-trimethyl-pyridine / 4 h / 20 - 120 °C
View Scheme
4-bromo-3,5-dimethyl benzonitrile
75344-77-3

4-bromo-3,5-dimethyl benzonitrile

3-(4-bromo-3,5-dimethyl-phenyl)-5-(2-hydroxy-prop-2-yl)-[1,2,4]oxadiazole
1458656-41-1

3-(4-bromo-3,5-dimethyl-phenyl)-5-(2-hydroxy-prop-2-yl)-[1,2,4]oxadiazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / Reflux
2.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C
2.2: 20 - 110 °C
View Scheme

4-Bromo-3,5-dimethyl benzonitrile Specification

The 4-Bromo-3,5-dimethyl benzonitrile with CAS registry number of 75344-77-3 is also called 4-Bromo-3,5-dimethylbenzonitrile. Its molecular formula is C9H8BrN, and its molecular weight is 210.07.

Physical properties about this chemical are: (1) ACD/LogP: 3.54; (2) # of Rule of 5 Violations: 0; (3) ACD/LogD (pH 5.5): 3; (4) ACD/LogD (pH 7.4): 3; (5) ACD/BCF (pH 5.5): 202; (6) ACD/BCF (pH 7.4): 202; (7) ACD/KOC (pH 5.5): 1557; (8) ACD/KOC (pH 7.4): 1557; (9) #H bond acceptors: 1; (10) #H bond donors: 0; (11) #Freely Rotating Bonds: 0; (12) Polar Surface Area: 23.79 Å2; (13) Index of Refraction: 1.579; (14) Molar Refractivity: 48.287 cm3; (15) Molar Volume: 145.305 cm3; (16) Polarizability: 19.143×10-24 cm3; (17) Surface Tension: 47.085 dyne/cm; (18) Density: 1.446 g/cm3; (19) Flash Point: 129.822 °C; (20) Enthalpy of Vaporization: 53.046 kJ/mol; (21) Boiling Point: 291.049 °C at 760 mmHg; (22) Vapour Pressure: 0.002 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1) SMILES: Cc1cc(cc(c1Br)C)C#N;
(2) InChI: InChI=1/C9H8BrN/c1-6-3-8(5-11)4-7(2)9(6)10/h3-4H,1-2H3;
(3) InChIKey: AVXHSMPHQGFXRG-UHFFFAOYAH;
(4) Std. InChI: InChI=1S/C9H8BrN/c1-6-3-8(5-11)4-7(2)9(6)10/h3-4H,1-2H3;
(5) Std. InChIKey: AVXHSMPHQGFXRG-UHFFFAOYSA-N

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