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2-Bromoaniline

HCID 11992
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Basic information

CAS
615-36-1
Standard SMILES
Nc1ccccc1Br
InChIKey
AOPBDRUWRLBSDB-UHFFFAOYSA-N
Molecular formula
C6H6BrN
Average molar mass
172.02 g/mol
Monoisotopic mass
170.96836

Names & identifiers

Preferred name
2-Bromoaniline
IUPAC
2-bromoaniline
English name
2-Bromoaniline
Molecular formula
C6H6BrN
Molecular weight
172.02

Names & synonyms

2-BROMOANILINE615-36-1o-BromoanilineBenzenamine, 2-bromo-Aniline, o-bromo-o-AminobromobenzeneVTP98DS78ENSC-7086DTXSID5060645RefChem:85845DTXCID0043054210-421-3
Show more names
2-Bromoanilines1-Amino-2-bromobenzene2-BromoaniLBROMOANILINE(2-)AKOS BBS-000036502-bromo-benzenamin
2-bromobenzenamine2-bromophenylamine2-bromioaniline2-bromaniline2-bromo-anilineortho-bromoanilineMFCD00007632aniline, 2-bromo-

Database identifiers

CAS
615-36-1
PubChem CID
11992
DTXSID
DTXSID5060645
UNII
VTP98DS78E
EC Number
210-421-3
Nikkaji
J94.957D

Properties

Computed structural properties

XLogP
2.1
Topological polar surface area
26 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
8
Formal charge
0
Complexity
74.9

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amines, Aromatic
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP2.11
Vapor Pressure0.04 [mmHg]
Physical DescriptionBrown solid; mp = 27-32 deg C; [Alfa Aesar MSDS]

Physicochemical properties

Melting point
24 · 24-28 °C (lit.)
Boiling point
229 °C · 229 °C (lit.)
Density
1.52 g/mL · 1.52 g/mL at 25 °C (lit.)
refractive index
1.617 · 1.617-1.619
Flash point
230 °F · >230 °F
storage temp.
2 · 2-8°C
solubility
0.949 g/l · 0.949g/l
pka

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H302 (96.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P262, P264, P270, P273, P280, P301+P317, P302+P352, P316, P319, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 53 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: Benzenamine, 2-bromo-

REACH registered substance: 2-bromoaniline (EC: 210-421-3)

2-Bromoaniline: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA skin and strong eye irritant; May induce methemoglobinemia; Harmful by ingestion and inhalation; Toxic by skin absorption; Prolonged or repeated exposure may cause organ injury; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (96.2%)

Toxicology

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

Safety data

F
8-23
PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationBenzenamine, 2-bromo-: ACTIVE
Applications · 3 items

DescriptionO-bromoaniline, m-bromoaniline and p-bromoaniline corresponds to the three isomers of bromoaniline. All of them three are toxic with its toxicity being more severe than chloroanilines. It can be all via percutaneous absorption, being hemolytic and able to cause bladder cancer. It is mainly used for dye raw materials, such as azo dyes, quinazoline dyes and so on. Heating together with glycerol, concentrated sulfuric acid and o-bromonitrobenzene can generate 8-bromoquinoline. The preparation of the three isomers is as follows: Take the corresponding nitroaniline as raw material, have it reacted with sodium nitrite in sulfuric acid, leading to the formation of diazonium salt, followed by reaction with hydrobromic acid under the action of cuprous bromide, leading to the formation of nitrobromobenzene, further subjecting to iron powder reaction in the bromic acid to generate the above three isomers. Take benzene as raw material, under the action of iron powder, have it reacted with bromine to generate bromobenzene. It is then reacted with mixed acid (the mixture of sulfuric acid and nitric acid) to generate o-nitrobenzene and p-nitro bromobenzene (orthoaccounts of 35%; paraaccounts of 65%), so that the two are separated, followed by the same process as method one to generate o-bromoaniline and p-bromoaniline. Take bromoacetanilide as raw material, put it into sodium hydroxide solution; apply water vapor reflux to obtain the bromoaniline.

UsesOrganic synthesis intermediates

Uses2-Bromoaniline is used as a corrosion inhibitor, emulsifying and antiseptic agents. It is used in the rubber industry, e.g. diphenylguanidines, phenylenediamines mercaptobenzothiazoles, aniline ketones and etc.

Upstream & downstream products

Upstream raw materials

2-Nitroaniline

Downstream products

Related reactions

167 records
New reaction record
HRID 510 reaction equation
HRID 510As reactant750 AstraZeneca ELN dataset
HRID 9479 reaction equation
HRID 9479As reactantuspto-grants-2006_08
HRID 14422 reaction equation
HRID 14422As reactantuspto-grants-2010_06
HRID 50792 reaction equation
HRID 50792As reactantuspto-grants-2004_03
HRID 80486 reaction equation
HRID 80486As reactantuspto-grants-2014_09
HRID 82945 reaction equation
HRID 82945As reactantuspto-grants-2014_09
HRID 83981 reaction equation
HRID 83981As reactantuspto-grants-2014_09
HRID 142375 reaction equation
HRID 142375As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
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2.53 · 2.53(at 25℃)
form
Liquid After Melting
color
Clear yellow to red-brown
Water Solubility
Insoluble in water.
BRN
742062 · 742062
InChI
1S/C6H6BrN/c7-5-3-1-2-4-6(5)8/h1-4H,8H2
InChIKey
AOPBDRUWRLBSDB-UHFFFAOYSA-N
SMILES
Nc1ccccc1Br
CAS DataBase Reference
615 · 615-36-1(CAS DataBase Reference)
FDA UNII
98 DS78E · VTP98DS78E
NIST Chemistry Reference
2 · Benzenamine, 2-bromo-(615-36-1)
EPA Substance Registry System
2 · Benzenamine, 2-bromo- (615-36-1)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
6 · GHS06,GHS09
Signal word
Danger
Hazard statements
301 · H301+H311+H331-H315-H319-H411
Precautionary statements
501 · P501-P261-P273-P270-P271-P264-P280-P391-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405
PPE
2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes
T,Xn
Risk Statements
23 · 23/24/25-33-52/53-36/37/38-20/21/22-24/25
Safety Statements
36 · 36/37-45-61-36/37/39-26
RIDADR
2811 · UN 2811 6.1/PG 3
WGK Germany
3 · 3
F
8 · 8-23
Hazard Note
Toxic
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
III
HS Code
29214210 · 29214210
Storage Class
10 · 10 - Combustible liquids
Hazard Classifications
4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1STOT RE 2
REACH Registrations
Active
tsca
TSCA listed
ridadr
UN 2811 6.1/PG 3
hs_code
29214210
risk_code
23/24/25-33-52/53-36/37/38-20/21/22-24/25
Signal word
Danger
Symbol(GHS)
GHS06,GHS09
hazard_code
T,Xn
hazard_note
Toxic
safety_code
36/37-45-61-36/37/39-26
hazard_class
6.1
Storage Class
10 - Combustible liquids
packing_group
III
Hazard statements
H301+H311+H331-H315-H319-H411
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1STOT RE 2
Precautionary statements
P501-P261-P273-P270-P271-P264-P280-P391-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405
8-BromoquinolineDimidium bromideOndansetron2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl1,2-Dibromobenzene2'-BromoacetanilideTryptophol2-Bromophenylhydrazine hydrochloride12H- [1] benzothieno [2,3-a] carbazoleIndolo[3,2,1-jk]carbazole6-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one4-(2-Bromo-phenyl)-piperazine-1-carboxylic acid tert-butyl esterN-(tert-Butoxycarbonyl)-2-bromoaniline2-Pyridin-2-yl-1H-indole2-Aminostyrene