Methyl 2-bromomethyl-3-nitrobenzoate supplier

Name
Methyl 2-bromomethyl-3-nitrobenzoate
EINECS 619-354-8
CAS No. 98475-07-1
Article Data64
CAS DataBase
Density 1.624 g/cm³
Solubility
Melting Point 72-74 °C
Formula C₉H₈BrNO₄
Boiling Point 370.9 °C at 760 mmHg
Molecular Weight 274.071
Flash Point 178.1 °C
Transport Information
Appearance pale yellow solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-(Bromomethyl)-3-nitrobenzoicacid methyl ester;Methyl 2-(bromomethyl)-3-nitrobenzoate;
PSA 72.12000
LogP 2.79950

Synthetic route

: 59382-59-1
2-methyl-3-nitro-benzoic acid methyl ester

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

Conditions

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane Reflux;	100%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane for 16h; Heating;	98%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In acetic acid methyl ester at 57℃; for 18h;	98%

N-bromo-succinimide (NBS): N-bromo-succinimide (NBS)

: 62621-09-4
methyl 2-methyl-4-nitrobenzoate

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

Conditions

Conditions	Yield
With azobisisobutyronitrile In tetrachloromethane; hexane; dichloromethane	98%

: 60-29-7
diethyl ether

: 59382-59-1
2-methyl-3-nitro-benzoic acid methyl ester

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

Conditions

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane	88.3%

: 3-nitro-2-[(triphenyl-λ5-phosphanylidene)-methyl]-benzoic acid methyl ester

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CH2Cl2 2: benzoyl peroxide; bromine / CCl4 / 46 h / Irradiation; heating View Scheme

: N-bromosuccinamide

: 59382-59-1
2-methyl-3-nitro-benzoic acid methyl ester

: 94-36-0
dibenzoyl peroxide

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

Conditions

Conditions	Yield
In tetrachloromethane; ethyl acetate

...Expand

: 109-69-3
n-Butyl chloride

: 59382-59-1
2-methyl-3-nitro-benzoic acid methyl ester

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

Conditions

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane; cyclohexane

: 1975-50-4
2-methyl-3-nitrobenzic acid

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / 5 h / Reflux 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / Reflux 1.2: Reflux 2.1: bromine / tetrachloromethane / 20 °C View Scheme
Multi-step reaction with 2 steps 1: bis(trichloromethyl) carbonate / N,N-dimethyl-formamide / 6 h / Reflux 2: N-Bromosuccinimide; dibenzoyl peroxide / 8 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / 24 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / benzene / 24 h / Inert atmosphere; Reflux View Scheme

: 74-89-5
methylamine

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 682757-52-4
2-methyl-4-nitroisoindolin-1-one

Conditions

Conditions	Yield
In tetrahydrofuran; water at 20℃; for 18h; Inert atmosphere;	100%
In tetrahydrofuran; water at 20 - 60℃; for 8h;	91.9%
In methanol at 20℃; for 3h;	50%

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 827026-45-9
3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions

Conditions	Yield
Stage #1: rac-α-aminoglutarimide hydrochloride With triethylamine In dimethyl sulfoxide for 0.166667h; Inert atmosphere; Stage #2: 2-bromomethyl-3-nitro-benzoic acid methyl ester In dimethyl sulfoxide at 50 - 55℃; for 12.3333h; Inert atmosphere;	99.73%
With sodium carbonate at 100℃; for 0.75h; Reagent/catalyst; Temperature; Inert atmosphere;	98.5%
With sodium carbonate In acetonitrile at 70℃; for 8h; Solvent; Reagent/catalyst; Temperature;	98.8%

: 603-35-0
triphenylphosphine

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: (2-carbomethoxy-6-nitrobenzyl)triphenylphosphonium bromide

Conditions

Conditions	Yield
In chloroform for 1h; Heating;	99%
In chloroform for 1.5h; Reflux;

: 2393-23-9
4-methoxy-benzylamine

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 2-(4-methoxybenzyl)-4-nitroisoindolin-1-one

Conditions

Conditions	Yield
In tetrahydrofuran at 50℃; for 24h; Inert atmosphere;	99%

: 107-10-8
propylamine

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 4-nitro-2-propyl-2,3-dihydroisoindol-1-one

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 5h; Inert atmosphere;	97%

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 366452-97-3
4-nitro-2,3-dihydro-1H-isoindol-1-one

Conditions

Conditions	Yield
With ammonium hydroxide at 90℃; for 2h;	96.04%
With ammonia In methanol at 20℃; for 2.5h;	90%
With ammonia In methanol at 20℃; for 2h;	81%

: 62-53-3
aniline

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 4-nitro-2-phenylisoindolin-1-one

Conditions

Conditions	Yield
at 40℃; for 0.0833333h;	96.03%

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 2353-44-8
(+/-)-α-aminoglutarimide

: 827026-45-9
3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 3h; Reflux;	96%
Stage #1: 2-bromomethyl-3-nitro-benzoic acid methyl ester; (+/-)-α-aminoglutarimide With sodium carbonate In acetonitrile at 5℃; Inert atmosphere; Reflux; Large scale; Stage #2: With hydrogenchloride In water at 20 - 62℃; for 4h; pH=< 6; Large scale;	79.5%
With triethylamine In N,N-dimethyl-formamide at 25 - 100℃; for 7h; Inert atmosphere;
With potassium hydrogencarbonate In acetonitrile Reflux;
With triethylamine In N,N-dimethyl-formamide at 75℃; for 20h;

: 100-46-9
benzylamine

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 1630974-73-0
2-benzyl-4-nitro-2,3-dihydroisoindol-1-one

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 5h; Inert atmosphere;	95%

: 52099-72-6
1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 1090902-91-2
2-(3-isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-3-nitro-benzoic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 2h;	94%

: 106-49-0
p-toluidine

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 1630974-71-8
2-(p-tolyl)-4-nitro-2,3-dihydroisoindol-1-one

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 5h; Inert atmosphere;	94%

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 2-[[(Amino)(imino)methyl]thiomethyl]-3-nitrobenzoic acid, methyl ester, hydrobromide

Conditions

Conditions	Yield
With thiourea In methanol; ethyl acetate	93%
With thiourea In methanol

: (+)-9-amino-5-(4-methoxybenzyl)-2-oxa-5-azaspiro[3.5]nonan-6-one

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: (+)-5-(4-methoxybenzyl)-9-(4-nitro-1-oxoisoindolin-2-yl)-2-oxa-5-azaspiro[3.5]nonan-6-one

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 75℃; for 20h; Inert atmosphere;	93%

: (-)-9-amino-5-(4-methoxybenzyl)-2-oxa-5-azaspiro[3.5]nonan-6-one

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: (-)-5-(4-methoxybenzyl)-9-(4-nitro-1-oxoisoindolin-2-yl)-2-oxa-5-azaspiro[3.5]nonan-6-one

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 75℃; for 20h; Inert atmosphere;	93%

: (S)-methyl 4,5-diamino-5-oxopentanoate hydrochloride

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: (S)-methyl 5-amino-4-(4-nitro-1-oxoisoindolin-2-yl)-5-oxopentanoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 22℃; for 17h;	93%

: 106-47-8
4-chloro-aniline

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 1630974-72-9
2-(4-chlorophenyl)-4-nitro-2,3-dihydroisoindol-1-one

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 5h; Inert atmosphere;	90%

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 825655-17-2
2-(azidomethyl)-3-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With sodium azide In DMF (N,N-dimethyl-formamide); water	89.6%
With sodium azide In DMF (N,N-dimethyl-formamide); water	89.6%

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 21568-87-6
2-aminocaprolactam

: 4-nitro-2-[(3S)-2-oxoazepan-3-yl]isoindoline-1-one

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 50℃; for 18h;	89%

: 109-85-3
2-methoxyethylamine

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 1381925-34-3
2-(2-methoxyethyl)-4-nitro-2,3-dihydro-isoindol-1-one

Conditions

Conditions	Yield
In toluene for 1h; Product distribution / selectivity; Reflux;	88%

: 696-40-2
3-iodobenzylamine

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 958888-81-8
2-(3-iodobenzyl)-4-nitroisoindolin-1-one

Conditions

Conditions	Yield
With triethylamine In metahnol at 20℃; Reflux;	87%

: 6525-53-7, 16422-27-8, 40149-68-6
glutamic acid dimethyl ether

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 827026-43-7
2-(4-nitro-1-oxo-1,3-dihydroisoindol-2-yl)glutaric acid dimethyl ester

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 45℃; for 16h; Reagent/catalyst; Solvent;	86.3%
With sodium hydrogencarbonate In acetonitrile Heating / reflux;	78%

: 35320-23-1
(R)-2-aminopropan-1-ol

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 1381925-26-3
2-((R)-2-hydroxy-1-methyl-ethyl)-4-nitro-2,3-dihydroisoindol-1-one

Conditions

Conditions	Yield
In toluene at 20 - 50℃; for 24h; Product distribution / selectivity;	86%

: 6258-60-2
p-methoxybenzylmercaptan

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: methyl 2-(((4-methoxybenzyl)thio)methyl)-3-nitrobenzoate

Conditions

Conditions	Yield
Stage #1: p-methoxybenzylmercaptan With triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 2-bromomethyl-3-nitro-benzoic acid methyl ester In dichloromethane at 20℃;	86%

: (S)-tert-butyl 4,5-diamino-5-oxopentanoate hydrochloride

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: C17H21N3O6

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 75℃; Inert atmosphere;	83%

: 3-amino(piperidine-3,5,5-d3)-2,6-dione

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 1620016-92-3
3-(4-nitro-1-oxoisoindolin-2-yl)(piperidine-3,5,5-d3)-2,6-dione

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl acetamide at 20℃; for 18h;	81%

: C12H15(2)HN2O3*ClH

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: C20H18(2)HN3O6

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 75℃; Inert atmosphere;	81%

: 17083-25-9
2-amino-3-tert-butoxypropionic acid

: 98475-07-1
2-bromomethyl-3-nitro-benzoic acid methyl ester

: 827026-45-9
3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions

Conditions	Yield
Stage #1: 2-amino-3-tert-butoxypropionic acid; 2-bromomethyl-3-nitro-benzoic acid methyl ester With sodium hydrogencarbonate In acetonitrile at 5 - 20℃; Reflux; Stage #2: With hydrogenchloride In water at 58 - 62℃; for 4.16667h; pH=< 6; Temperature; Time;	79.5%

Methyl 2-bromomethyl-3-nitrobenzoate Specification

The Benzoic acid,2-(bromomethyl)-3-nitro-, methyl ester is an organic compound with the formula C₉H₈BrNO₄. The IUPAC name of this chemical is methyl 2-(bromomethyl)-3-nitrobenzoate. With the CAS registry number 98475-07-1, it is also named as 2-(Bromomethyl)-3-nitrobenzoic acid methyl ester.

Physical properties about Benzoic acid,2-(bromomethyl)-3-nitro-, methyl ester are: (1)ACD/LogP: 2.52; (2)ACD/LogD (pH 5.5): 2.52; (3)ACD/LogD (pH 7.4): 2.52; (4)ACD/BCF (pH 5.5): 48.39; (5)ACD/BCF (pH 7.4): 48.39; (6)ACD/KOC (pH 5.5): 559.18; (7)ACD/KOC (pH 7.4): 559.18; (8)#H bond acceptors: 5; (9)#Freely Rotating Bonds: 4; (10)Polar Surface Area: 72.12 Å²; (11)Index of Refraction: 1.593; (12)Molar Refractivity: 57.21 cm³; (13)Molar Volume: 168.6 cm³; (14)Polarizability: 22.68×10^-24cm³; (15)Surface Tension: 53.6 dyne/cm; (16)Density: 1.624 g/cm³; (17)Flash Point: 178.1 °C; (18)Enthalpy of Vaporization: 61.78 kJ/mol; (19)Boiling Point: 370.9 °C at 760 mmHg; (20)Vapour Pressure: 1.07E-05 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: BrCc1c(cccc1[N+]([O-])=O)C(=O)OC
(2)InChI: InChI=1/C9H8BrNO4/c1-15-9(12)6-3-2-4-8(11(13)14)7(6)5-10/h2-4H,5H2,1H3
(3)InChIKey: FCGIVHSBEKGQMZ-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C9H8BrNO4/c1-15-9(12)6-3-2-4-8(11(13)14)7(6)5-10/h2-4H,5H2,1H3
(5)Std. InChIKey: FCGIVHSBEKGQMZ-UHFFFAOYSA-N

Product Name

Methyl 2-bromomethyl-3-nitrobenzoate

Synthetic route

Methyl 2-bromomethyl-3-nitrobenzoate Specification

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