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39478-78-9

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39478-78-9 Usage

Chemical Properties

clear yellow to brown liquid after melting

Check Digit Verification of cas no

The CAS Registry Mumber 39478-78-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,9,4,7 and 8 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 39478-78:
(7*3)+(6*9)+(5*4)+(4*7)+(3*8)+(2*7)+(1*8)=169
169 % 10 = 9
So 39478-78-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H8BrN/c1-5-2-3-6(8)4-7(5)9/h2-4H,9H2,1H3

39478-78-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Bromo-2-methylaniline

1.2 Other means of identification

Product number -
Other names 4-bromo-o-toluidine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:39478-78-9 SDS

39478-78-9Synthetic route

4-bromo-2-nitrotoluene
60956-26-5

4-bromo-2-nitrotoluene

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

Conditions
ConditionsYield
With tin(II) chloride dihdyrate In ethyl acetate at 0℃; for 4h; Reflux;97%
With stannous chloride hydrate In ethyl acetate at 30℃;93%
With iron; ammonium chloride for 48h; Heating;92%
para-bromotoluene
106-38-7

para-bromotoluene

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

Conditions
ConditionsYield
With CH5NO3S*CHF3O3S; iron(II) sulfate In water; acetonitrile at 20℃; for 16h;71%
hydrogenchloride
7647-01-0

hydrogenchloride

4-bromo-2-nitrotoluene
60956-26-5

4-bromo-2-nitrotoluene

tin

tin

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

4-Methyl-3-nitroanilin
119-32-4

4-Methyl-3-nitroanilin

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: H2SO4; NaNO2
1.2: 57.5 percent / CuBr
2.1: 84.5 percent / Fe; CH3COOH
View Scheme
4-bromo-2-nitrotoluene
60956-26-5

4-bromo-2-nitrotoluene

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

Conditions
ConditionsYield
With ammonium chloride In ethanol; water
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

5-bromo-2-methyl aniline hydrochloride

5-bromo-2-methyl aniline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane for 3h;100%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

2,5-hexanedione
110-13-4

2,5-hexanedione

1-(5-bromo-2-methyl-phenyl)-2,5-dimethyl-pyrrole
1157455-13-4

1-(5-bromo-2-methyl-phenyl)-2,5-dimethyl-pyrrole

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 24h; Reflux;100%
hydrogenchloride In ethanol; water for 18h; Reflux;60%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

5-azido-2-methylbenzeneamine

5-azido-2-methylbenzeneamine

Conditions
ConditionsYield
With copper(l) iodide; sodium azide; sodium L-ascorbate; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane In ethanol for 0.5h; Heating;99%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

N-(5-bromo-2-methylphenyl)-2,2,2-trifluoroacetamide
338451-90-4

N-(5-bromo-2-methylphenyl)-2,2,2-trifluoroacetamide

Conditions
ConditionsYield
With triethylamine In dichloromethane for 1h;99%
In dichloromethane at 0℃; for 1h;76%
In dichloromethane at 20℃; for 1h;9.3 g
In dichloromethane at 20℃; for 1h;
3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

5-{4-(3-aminophenyl)-[1,2,3]triazol-1-yl}-2-methylphenylamine

5-{4-(3-aminophenyl)-[1,2,3]triazol-1-yl}-2-methylphenylamine

Conditions
ConditionsYield
With sodium azide; trans-N,N'-dimethylcyclohexane-1,2-diamine; sodium L-ascorbate; copper(l) iodide In dimethyl sulfoxide at 70℃; for 12h;98%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

tert-butyl (5-bromo-2-methylphenyl)carbamate

tert-butyl (5-bromo-2-methylphenyl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;98%
Stage #1: 5-bromo-2-methylaniline With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.416667h;
Stage #2: di-tert-butyl dicarbonate In N,N-dimethyl-formamide at 0 - 40℃; for 22h;
In tetrahydrofuran at 75℃; for 12h;
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

N-(5-bromo-2-methylphenyl)iminodiacetic acid diethyl ester
1190891-69-0

N-(5-bromo-2-methylphenyl)iminodiacetic acid diethyl ester

Conditions
ConditionsYield
96%
n-propanesulfonyl chloride
10147-36-1

n-propanesulfonyl chloride

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

N-(5-bromo-2-methylphenyl)propane-1-sulfonamide

N-(5-bromo-2-methylphenyl)propane-1-sulfonamide

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 20℃; for 16h;96%
With pyridine; dmap In dichloromethane at 20℃; for 40h; Inert atmosphere;96%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

C7H7N5O2

C7H7N5O2

C11H11BrN4O2

C11H11BrN4O2

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 120℃; for 24h;94.8%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

allyl bromide
106-95-6

allyl bromide

N,N-diallyl-5-bromo-2-methylaniline
1332626-19-3

N,N-diallyl-5-bromo-2-methylaniline

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 6h; Inert atmosphere;94%
N-(tert-butoxycarbonyl)sarcosine
13734-36-6

N-(tert-butoxycarbonyl)sarcosine

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

tert-butyl 2-(5-bromo-2-methylphenylamino)-2-oxoethyl(methyl)carbamate
1172620-97-1

tert-butyl 2-(5-bromo-2-methylphenylamino)-2-oxoethyl(methyl)carbamate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 15h;92%
(2-{[4-chloro-2-(methoxycarbonyl)phenyl]amino}-2-oxoethoxy)acetic acid
1103929-71-0

(2-{[4-chloro-2-(methoxycarbonyl)phenyl]amino}-2-oxoethoxy)acetic acid

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

methyl 2-[({2-[(5-bromo-2-methylphenyl)amino]-2-oxoethoxy}acetyl)amino]-5-chlorobenzoate
1190222-29-7

methyl 2-[({2-[(5-bromo-2-methylphenyl)amino]-2-oxoethoxy}acetyl)amino]-5-chlorobenzoate

Conditions
ConditionsYield
Stage #1: (2-{[4-chloro-2-(methoxycarbonyl)phenyl]amino}-2-oxoethoxy)acetic acid With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: 5-bromo-2-methylaniline In N,N-dimethyl acetamide at 0 - 20℃;
92%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

7-chloro-2-morpholino-N-(pyridin-2-ylmethyl)quinazolin-4-amine

7-chloro-2-morpholino-N-(pyridin-2-ylmethyl)quinazolin-4-amine

7-(3-amino-4-methylphenyl)-2-morpholino-N-(pyridin-2-ylmethyl)quinazolin-4-amine

7-(3-amino-4-methylphenyl)-2-morpholino-N-(pyridin-2-ylmethyl)quinazolin-4-amine

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methylaniline With magnesium; ethylene dibromide In tetrahydrofuran at 60 - 80℃; for 0.25h; Inert atmosphere;
Stage #2: 7-chloro-2-morpholino-N-(pyridin-2-ylmethyl)quinazolin-4-amine With bis(triphenylphosphine)nickel(II) chloride In tetrahydrofuran at 60℃; for 3h; Kumada Cross-Coupling; Inert atmosphere;
91%
methyl 2-phenyl-2-(2-tosylhydrazono)acetate
18793-81-2

methyl 2-phenyl-2-(2-tosylhydrazono)acetate

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

methyl 2-((5-bromo-2-methylphenyl)amino)-2-phenylacetate

methyl 2-((5-bromo-2-methylphenyl)amino)-2-phenylacetate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 24h; Irradiation;87%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

6-bromo-1H-indazole
79762-54-2

6-bromo-1H-indazole

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methylaniline With sodium tetrafluoroborate; sodium nitrite
Stage #2: With 18-crown-6 ether; potassium acetate In chloroform
85%
Stage #1: 5-bromo-2-methylaniline With potassium acetate; acetic anhydride In chloroform at 60 - 65℃; for 0.5h;
Stage #2: With potassium acetate; isopentyl nitrite In chloroform at 60℃; for 15h;
Stage #3: With hydrogenchloride In methanol; water at 60℃; for 2h;
51%
Stage #1: 5-bromo-2-methylaniline With tetrafluoroboric acid; sodium nitrite In water at 0℃;
Stage #2: With 18-crown-6 ether; potassium acetate In chloroform at 20℃; Further stages.;
Multi-step reaction with 2 steps
1: tetrafluoroboric acid; sodium nitrite / water / 0.5 h / 0 - 20 °C
2: 18-crown-6 ether; potassium acetate / chloroform / 2 h / 20 °C
View Scheme
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

acryloyl chloride
814-68-6

acryloyl chloride

N-(5-bromo-2-methylphenyl)acrylamide

N-(5-bromo-2-methylphenyl)acrylamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -78 - 20℃;85%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

acetic anhydride
108-24-7

acetic anhydride

4'-bromo-2'-methylacetanilide
24106-05-6

4'-bromo-2'-methylacetanilide

Conditions
ConditionsYield
In benzene for 3.5h;84.4%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

dicyanozinc
557-21-1

dicyanozinc

5-cyano-2-methylaniline
60710-80-7

5-cyano-2-methylaniline

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; for 2h;84%
(Z)-(2,3-dibromoprop-1-en-1-yl)benzene
23970-90-3, 96725-21-2, 21003-54-3

(Z)-(2,3-dibromoprop-1-en-1-yl)benzene

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

N-(5-bromo-2-methylphenyl)-N-[(Z)-2-bromo-3-phenylprop-2-enyl]amine
1380159-20-5

N-(5-bromo-2-methylphenyl)-N-[(Z)-2-bromo-3-phenylprop-2-enyl]amine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h;84%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

phenylboronic acid
98-80-6

phenylboronic acid

4-methyl-[1,1'-biphenyl]-3-amine
80938-67-6

4-methyl-[1,1'-biphenyl]-3-amine

Conditions
ConditionsYield
With potassium carbonate In water at 70℃; for 2h; Suzuki Coupling; Inert atmosphere;82%
With potassium carbonate In water at 70℃; for 2h; Suzuki Coupling; Inert atmosphere;81%
With potassium carbonate In water at 70℃; for 2h; Suzuki Coupling; Inert atmosphere; Green chemistry;80%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water for 5h; Reflux; Inert atmosphere;
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

acetic anhydride
108-24-7

acetic anhydride

isopentyl nitrite
110-46-3

isopentyl nitrite

1-(6-bromo-1H-indazol-1-yl)ethanone

1-(6-bromo-1H-indazol-1-yl)ethanone

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methylaniline; acetic anhydride In chloroform at 0 - 5℃;
Stage #2: acetic anhydride; isopentyl nitrite With potassium acetate In chloroform Heating / reflux;
Stage #3: With sodium hydrogencarbonate In chloroform; water pH=7;
81%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

ethanolamine
141-43-5

ethanolamine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

N1-(5-bromo-2-methylphenyl)-N2-(2-hydroxyethyl)glycinamide
1146412-41-0

N1-(5-bromo-2-methylphenyl)-N2-(2-hydroxyethyl)glycinamide

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methylaniline; chloroacetyl chloride With potassium carbonate In tetrahydrofuran; water at 5 - 20℃; for 1.25h;
Stage #2: ethanolamine In tetrahydrofuran at 5 - 50℃; Product distribution / selectivity;
81%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

2-Nitrobenzenesulfonyl chloride
1694-92-4

2-Nitrobenzenesulfonyl chloride

N-(5-bromo-2-methylphenyl)-2-nitrobenzenesulfonamide
1023210-61-8

N-(5-bromo-2-methylphenyl)-2-nitrobenzenesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 3h;81%
CYANAMID
420-04-2

CYANAMID

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

5-bromo-2-methylphenylguanidine nitrate
1206604-19-4

5-bromo-2-methylphenylguanidine nitrate

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methylaniline With nitric acid In methanol at 60℃; for 0.5h;
Stage #2: CYANAMID In methanol; water for 6h; Reflux;
79.9%
2-bromo-1-cyclopropylethan-1-one
69267-75-0

2-bromo-1-cyclopropylethan-1-one

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

2-((5-bromo-2-methylphenyl)amino)-1-cyclopropylethan-1-one

2-((5-bromo-2-methylphenyl)amino)-1-cyclopropylethan-1-one

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine at 100℃; for 15h;78.4%
Stage #1: 5-bromo-2-methylaniline With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 2-bromo-1-cyclopropylethan-1-one In N,N-dimethyl-formamide at 60℃; for 3h;
45%
2,6-Diacetylpyridine
1129-30-2

2,6-Diacetylpyridine

5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

2,6-bis-[1-(5-bromo-2-methylphenylimino)-ethyl]-pyridine

2,6-bis-[1-(5-bromo-2-methylphenylimino)-ethyl]-pyridine

Conditions
ConditionsYield
toluene-4-sulfonic acid In toluene for 72h; Heating / reflux;78%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

N-(5-bromo-2-methylphenyl)methanesulfonamide

N-(5-bromo-2-methylphenyl)methanesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 2h;78%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

5-bromo-2-methyl-phenylhydrazine hydrochloride

5-bromo-2-methyl-phenylhydrazine hydrochloride

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methylaniline With hydrogenchloride; sodium nitrite at 0℃;
Stage #2: With hydrogenchloride; tin(ll) chloride at 0℃; for 1h;
75%
5-bromo-2-methylaniline
39478-78-9

5-bromo-2-methylaniline

sodium nitrite
7632-00-0

sodium nitrite

5-bromo-2-methyl-phenylhydrazine hydrochloride

5-bromo-2-methyl-phenylhydrazine hydrochloride

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methylaniline; sodium nitrite With hydrogenchloride In water at 0℃; for 0.5h;
Stage #2: With hydrogenchloride; tin(ll) chloride In water at 0℃; for 1.83333h;
Stage #3: With hydrogenchloride; sodium hydroxide more than 3 stages;
75%

39478-78-9Relevant articles and documents

-

Chardonnens,Buchs

, p. 872,876 (1946)

-

Method for preparing halogenated aniline from halogenated nitrobenzene through catalytic hydrogenation

-

Paragraph 0051-0053, (2017/07/22)

The invention discloses a method for preparing halogenated aniline from halogenated nitrobenzene through catalytic hydrogenation. The method comprises the following steps: in a reaction kettle, performing liquid phase catalytic hydrogenation reaction to halogenated nitrobenzene under the action of a sulfur-doped carbon material loaded noble metal catalyst, to obtain halogenated aniline shown in the formula (II), wherein the loading quantity of noble metal in the sulfur-doped carbon material loaded noble metal catalyst is 0.1-5wt%. In the method, the catalyst has good stability, the hydrogenation halogen removal side effect can be effectively inhibited under the condition of having no added halogen removal inhibitor, and the product selectivity is high.

Direct and practical synthesis of primary anilines through iron-catalyzed C-H bond amination

Legnani, Luca,Cerai, Gabriele Prina,Morandi, Bill

, p. 8162 - 8165 (2018/05/22)

The direct C-H amination of arenes is an important strategy to streamline the discovery and preparation of functional molecules. Herein, we report an operationally simple arene C-H amination reaction that, in contrast to most literature precedent, affords directly the synthetically versatile primary aniline products without relying on protecting group manipulations. Inexpensive Fe(II)-sulfate serves as a convenient catalyst for the transformation. The reaction tolerates a wide scope of arenes, including structurally complex drugs. Importantly, the arene substrates are used as limiting reagents in the transformation. This operationally simple transformation should considerably accelerate the discovery of medicines and functional molecules.

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