Benzenamine, 2-bromo-6-chloro- supplier

Name
Benzenamine, 2-bromo-6-chloro-
EINECS
CAS No. 59772-49-5
Article Data8
CAS DataBase
Density 1.722 g/cm³
Solubility
Melting Point 57-58 °C(Solv: water (7732-18-5); ethanol (64-17-5))
Formula C₆H₅BrClN
Boiling Point 242.8 °C at 760 mmHg
Molecular Weight 206.469
Flash Point 100.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Bromo-6-chloroaniline;2-Bromo-6-chlorobenzenamine;
PSA 26.02000
LogP 3.26590

Synthetic route

: 93224-85-2
2-bromo-6-chlorobenzoic acid

: 59772-49-5
2-Chloro-6-bromoaniline

Conditions

Conditions	Yield
Stage #1: 2-bromo-6-chlorobenzoic acid With sulfuric acid at 60℃; for 1.5h; Stage #2: With sodium azide at 20℃; for 42h; Schmidt rearrangement; Stage #3: With ammonium hydroxide at 0℃;	92%

: 4-amino-3-bromo-5-chlorobenzenesulfonamide

: 59772-49-5
2-Chloro-6-bromoaniline

Conditions

Conditions	Yield
With sulfuric acid at 150℃; for 2h; Temperature;	85%

: 90493-87-1
2'-Chloro-6'-bromobenzanilide

: 59772-49-5
2-Chloro-6-bromoaniline

Conditions

Conditions	Yield
With sulfuric acid for 3h; Heating;	66%

: 615-36-1
2-bromoaniline

A: 59772-49-5
2-Chloro-6-bromoaniline

B: 873-38-1
4-chloro-2-bromoaniline

Conditions

Conditions	Yield
With N-chloro-succinimide; 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1S,2S)-2-(mesitylselanyl)-2,3-dihydro-1H-inden-1-yl)thiourea In chloroform-d1 at 0℃; for 18h; regioselective reaction;	A 40% B n/a

: 95-51-2
2-Chloroaniline

A: 59772-49-5
2-Chloro-6-bromoaniline

B: 38762-41-3
2-chloro-4-bromoaniline

Conditions

Conditions	Yield
With dihydrogen peroxide; ammonium bromide; acetic acid at 20℃; for 2.5h;
Stage #1: o-chloroaniline With dihydrogen peroxide; acetic acid; potassium bromide In water at 20℃; for 3h; Stage #2: With sodium hydrogencarbonate In diethyl ether; water regioselective reaction;

: 35758-75-9
N-(2-bromophenyl)hydroxylamine

: 59772-49-5
2-Chloro-6-bromoaniline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: NaHCO3 / diethyl ether; H2O / 1 h / T < 5 deg C; or in benzene 2: 71 percent / SOCl2 / diethyl ether / 1 h / T < 5 deg C 3: 66 percent / 70percent H2SO4 / 3 h / Heating View Scheme

: 90493-81-5
N-(2-Bromo-phenyl)-N-hydroxy-benzamide

: 59772-49-5
2-Chloro-6-bromoaniline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / SOCl2 / diethyl ether / 1 h / T < 5 deg C 2: 66 percent / 70percent H2SO4 / 3 h / Heating View Scheme

: 95-51-2
2-Chloroaniline

A: 59772-49-5
2-Chloro-6-bromoaniline

B: 874-18-0
2-chloro-4,6-dibromoaniline

C: 38762-41-3
2-chloro-4-bromoaniline

Conditions

Conditions	Yield
With bromine at 20 - 25℃; for 0.0333333h; pH=8.5 - 9; aq. buffer;

...Expand

: 63-74-1
sulfanilamide

: 59772-49-5
2-Chloro-6-bromoaniline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N-chloro-succinimide / tetrahydrofuran / 25 h / 40 °C 2: N-Bromosuccinimide / acetonitrile / 3 h / 20 °C 3: sulfuric acid / 2 h / 150 °C View Scheme

: 59772-49-5
2-Chloro-6-bromoaniline

: 59772-48-4
1-bromo-3-chloro-2-nitrobenzene

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 70℃; for 2h;	94%
With trifluoroacetyl peroxide In dichloromethane at -5 - 5℃; for 2h;	75%

: 59772-49-5
2-Chloro-6-bromoaniline

: 113893-08-6
benzo[b]thiophen-3-yl-3-boronic acid

: C14H10ClNS

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In ethanol; toluene for 4h; Reflux;	91%

: 59772-49-5
2-Chloro-6-bromoaniline

: benzofurane-3-ylboronic acid

: C14H10ClNO

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In ethanol; toluene for 4h; Reflux;	91%

: 1126425-82-8
3-chloro-4-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-N-(TIPS)pyrrole

: 59772-49-5
2-Chloro-6-bromoaniline

: 1126425-92-0
2-chloro-6-(4-chloro-1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 35℃; for 12h; Suzuki-Miyaura coupling; Inert atmosphere;	82%

: 59772-49-5
2-Chloro-6-bromoaniline

: 365564-11-0
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole

: 1126425-86-2
2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 35℃; for 12h; Suzuki-Miyaura coupling; Inert atmosphere;	82%

: 1152312-10-1
methyl (S)-2-((tert-butoxycarbonyl)amino)-5-(triethylsilyl)pent-4-ynoate

: 59772-49-5
2-Chloro-6-bromoaniline

: C23H35ClN2O4Si

Conditions

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); N-Methyldicyclohexylamine In 1,4-dioxane at 60℃; for 36h; Inert atmosphere; Sealed tube;	82%

: 59772-49-5
2-Chloro-6-bromoaniline

: 98-80-6
phenylboronic acid

: 76838-82-9
3-chloro-[1,1'-biphenyl]-2-amine

Conditions

Conditions	Yield
Stage #1: 2-bromo-6-chloroaniline; phenylboronic acid With potassium carbonate In 1,4-dioxane; water for 0.166667h; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water for 1h;	81.1%

: 59772-49-5
2-Chloro-6-bromoaniline

: 4688-76-0
2-Biphenylboronic acid

: C18H14ClN

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In ethanol; water; toluene at 100℃; for 15h;	80%

: 591-50-4
iodobenzene

: 59772-49-5
2-Chloro-6-bromoaniline

: C18H13BrClN

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 4h; Inert atmosphere; Reflux;	70%

: 59772-49-5
2-Chloro-6-bromoaniline

: potassium vinyltrifluoroborate

: 2-chloro-6-vinylaniline

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In tetrahydrofuran; water at 80℃; for 9h;	56%

: 59772-49-5
2-Chloro-6-bromoaniline

: 79-04-9
chloroacetyl chloride

: chloro-acetic acid-(2-bromo-6-chloro-anilide)

: 59772-49-5
2-Chloro-6-bromoaniline

: 100140-98-5
N,N-diethyl-glycine-(2-bromo-6-chloro-anilide)

: 59772-49-5
2-Chloro-6-bromoaniline

: methyl 2-vinyl-6-chloroaniline-N-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / tetrahydrofuran; water / 9 h / 80 °C 2: pyridine / dichloromethane / 0 - 25 °C View Scheme

: 59772-49-5
2-Chloro-6-bromoaniline

: methyl 7-chloro-indole-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / tetrahydrofuran; water / 9 h / 80 °C 2: pyridine / dichloromethane / 0 - 25 °C 3: bis(benzonitrile)palladium(II) dichloride; tert.-butylnitrite; oxygen / tert-butyl alcohol / 15 h / 70 °C / 760.05 Torr / Schlenk technique View Scheme

: 59772-49-5
2-Chloro-6-bromoaniline

: 53924-05-3
7-chloro-1H-indole

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / tetrahydrofuran; water / 9 h / 80 °C 2: pyridine / dichloromethane / 0 - 25 °C 3: bis(benzonitrile)palladium(II) dichloride; tert.-butylnitrite; oxygen / tert-butyl alcohol / 15 h / 70 °C / 760.05 Torr / Schlenk technique 4: potassium hydroxide / methanol / 1 h / Reflux View Scheme

Yield

Multi-step reaction with 4 steps
1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / tetrahydrofuran; water / 9 h / 80 °C
2: pyridine / dichloromethane / 0 - 25 °C
3: bis(benzonitrile)palladium(II) dichloride; tert.-butylnitrite; oxygen / tert-butyl alcohol / 15 h / 70 °C / 760.05 Torr / Schlenk technique
4: potassium hydroxide / methanol / 1 h / Reflux
View Scheme

: 59772-49-5
2-Chloro-6-bromoaniline

: 1073494-35-5
7-(o-tolyl)-1H-indole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / tetrahydrofuran; water / 9 h / 80 °C 2: pyridine / dichloromethane / 0 - 25 °C 3: bis(benzonitrile)palladium(II) dichloride; tert.-butylnitrite; oxygen / tert-butyl alcohol / 15 h / 70 °C / 760.05 Torr / Schlenk technique 4: potassium hydroxide / methanol / 1 h / Reflux 5: palladium diacetate; potassium phosphate; ruphos / tetrahydrofuran; toluene / 22 h / 100 °C / Schlenk technique; Inert atmosphere View Scheme

Yield

Multi-step reaction with 5 steps
1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / tetrahydrofuran; water / 9 h / 80 °C
2: pyridine / dichloromethane / 0 - 25 °C
3: bis(benzonitrile)palladium(II) dichloride; tert.-butylnitrite; oxygen / tert-butyl alcohol / 15 h / 70 °C / 760.05 Torr / Schlenk technique
4: potassium hydroxide / methanol / 1 h / Reflux
5: palladium diacetate; potassium phosphate; ruphos / tetrahydrofuran; toluene / 22 h / 100 °C / Schlenk technique; Inert atmosphere
View Scheme

: 59772-49-5
2-Chloro-6-bromoaniline

: C21H12ClNO

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / toluene; ethanol / 4 h / Reflux 2: triethylamine / 0 °C 3: trichlorophosphate / nitrobenzene / 12 h / 150 °C View Scheme

: 59772-49-5
2-Chloro-6-bromoaniline

C27H24BNO3: C27H24BNO3

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / toluene; ethanol / 4 h / Reflux 2: triethylamine / 0 °C 3: trichlorophosphate / nitrobenzene / 12 h / 150 °C 4: potassium acetate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / 1,4-dioxane / 12 h / Reflux View Scheme

: 59772-49-5
2-Chloro-6-bromoaniline

: C54H33N5S

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / toluene; ethanol / 4 h / Reflux 2: triethylamine / 0 °C 3: trichlorophosphate / nitrobenzene / 12 h / 150 °C 4: potassium acetate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / 1,4-dioxane / 12 h / Reflux 5: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 12 h / Reflux View Scheme

Yield

Multi-step reaction with 5 steps
1: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / toluene; ethanol / 4 h / Reflux
2: triethylamine / 0 °C
3: trichlorophosphate / nitrobenzene / 12 h / 150 °C
4: potassium acetate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / 1,4-dioxane / 12 h / Reflux
5: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 12 h / Reflux
View Scheme

: 59772-49-5
2-Chloro-6-bromoaniline

: C54H32N4S

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / toluene; ethanol / 4 h / Reflux 2: triethylamine / 0 °C 3: trichlorophosphate / nitrobenzene / 12 h / 150 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 12 h / Reflux 5: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 5 h / Reflux 6: tris-(dibenzylideneacetone)dipalladium(0); XPhos; potassium phosphate / 1,4-dioxane / 12 h / Reflux View Scheme

Yield

Multi-step reaction with 6 steps
1: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / toluene; ethanol / 4 h / Reflux
2: triethylamine / 0 °C
3: trichlorophosphate / nitrobenzene / 12 h / 150 °C
4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 12 h / Reflux
5: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 5 h / Reflux
6: tris-(dibenzylideneacetone)dipalladium(0); XPhos; potassium phosphate / 1,4-dioxane / 12 h / Reflux
View Scheme

Benzenamine, 2-bromo-6-chloro- Specification

The Benzenamine, 2-bromo-6-chloro-, with the CAS registry number of 59772-49-5, is also known as 2-Bromo-6-chlorobenzenamine. This chemical's molecular formula is C₆H₅BrClN and molecular weight is 206.4676. What's more, its systematic name is called 2-Bromo-6-chloroaniline.

Physical properties about Benzenamine, 2-bromo-6-chloro- are: (1)ACD/LogP: 3.12; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.12; (4)ACD/LogD (pH 7.4): 3.12; (5)ACD/BCF (pH 5.5): 137.73; (6)ACD/BCF (pH 7.4): 137.73; (7)ACD/KOC (pH 5.5): 1182.27; (8)ACD/KOC (pH 7.4): 1182.29; (9)#H bond acceptors: 1; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 26.02 Å²; (13)Index of Refraction: 1.638; (14)Molar Refractivity: 43.07 cm³; (15)Molar Volume: 119.8 cm³; (16)Surface Tension: 50.4 dyne/cm; (17)Density: 1.722 g/cm³; (18)Flash Point: 100.6 °C; (19)Enthalpy of Vaporization: 47.98 kJ/mol; (20)Boiling Point: 242.8 °C at 760 mmHg; (21)Vapour Pressure: 0.0333 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: Clc1cccc(Br)c1N
(2) InChI: InChI=1/C6H5BrClN/c7-4-2-1-3-5(8)6(4)9/h1-3H,9H2
(3) InChIKey: BIMSFWCFKDVSNO-UHFFFAOYAX

Product Name

Benzenamine, 2-bromo-6-chloro-

Synthetic route

Benzenamine, 2-bromo-6-chloro- Specification

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