2-Hydroxy-5-nitrobenzyl bromide supplier

Name
2-HYDROXY-5-NITROBENZYL BROMIDE
EINECS 212-248-9
CAS No. 772-33-8
Article Data3
CAS DataBase
Density 1.795 g/cm³
Solubility
Melting Point 144-149 °C
Formula C₇H₆BrNO₃
Boiling Point 383 °C at 760 mmHg
Molecular Weight 232.034
Flash Point 185.5 °C
Transport Information UN 3261 8/PG 2
Appearance Beige to yellow crystalline powder
Safety 26-36/37/39-45
Risk Codes 34
Molecular Structure
Hazard Symbols C
Synonyms o-Cresol, alpha-bromo-4-nitro-;alpha-Bromo-4-nitro-o-cresol;2-(Bromomethyl)-4-nitrophenol;a-Bromo-4-nitro-o-cresol;Koshland's Reagent;
PSA 66.05000
LogP 2.71850

Synthetic route

: 2973-19-5
2-hydroxy-5-nitrobenzyl chloride

: 772-33-8
Koshlands reagent I

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid at 70 - 80℃;

5-nitro-2-oxy-benzyl acetate: 5-nitro-2-oxy-benzyl acetate

: 772-33-8
Koshlands reagent I

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid at 70 - 80℃;

: 883715-40-0
2-(2-methyl-4-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

: 772-33-8
Koshlands reagent I

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile / 2 h / 90 °C / Inert atmosphere 2: dihydrogen peroxide; water / 20 °C View Scheme

: 1030832-68-8
2-(2-(bromomethyl)-4-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

A: 76-09-5
2,3-dimethyl-2,3-butane diol

B: 772-33-8
Koshlands reagent I

C: 11113-50-1
boric acid

Conditions

Conditions	Yield
With water; dihydrogen peroxide at 20℃; Kinetics;

...Expand

: 7149-70-4
2-bromo-5-nitrotoluene

: 772-33-8
Koshlands reagent I

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 48 h / 85 °C / Inert atmosphere 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile / 2 h / 90 °C / Inert atmosphere 3: dihydrogen peroxide; water / 20 °C View Scheme

: 772-33-8
Koshlands reagent I

: 2-Hydroxy-5-nitro-benzyl hexamethylenetetramine Hydrobromide

Conditions

Conditions	Yield
With hexamethylenetetramine In chloroform	100%

: 33342-99-3, 160751-58-6, 160751-59-7
(+/-)-2-methyl-1-phenylpyrrolidine

: 772-33-8
Koshlands reagent I

: 2-(4-(2-methylpyrrolidin-1-yl)benzyl)-4-nitrophenol

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In dichloromethane at 20℃; for 24h; Inert atmosphere;	99%

: 4096-20-2
N-phenyl piperidine

: 772-33-8
Koshlands reagent I

: 4-nitro-2-(4-(piperidin-1-yl)benzyl)phenol

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In dichloromethane at 20℃; for 24h; Inert atmosphere;	99%

: 479-59-4
julolidine

: 772-33-8
Koshlands reagent I

: 4-nitro-2-((2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)methyl)phenol

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In dichloromethane at 20℃; for 24h; Inert atmosphere;	99%

: 772-33-8
Koshlands reagent I

: 91-66-7
N,N-diethylaniline

: 2-(4-(diethylamino)benzyl)-4-nitrophenol

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In dichloromethane at 20℃; for 24h; Inert atmosphere;	99%

: 772-33-8
Koshlands reagent I

: 2217-07-4
N,N-dipropylaniline

: 2-(4-(dipropylamino)benzyl)-4-nitrophenol

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In dichloromethane at 20℃; for 24h; Inert atmosphere;	99%

: 54104-82-4
1-p-tolylpyrrolidine

: 772-33-8
Koshlands reagent I

: 2-(5-methyl-2-(pyrrolidin-1-yl)benzyl)-4-nitrophenol

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In dichloromethane at 20℃; for 24h; Inert atmosphere;	99%

: 772-33-8
Koshlands reagent I

: 25364-44-7
N-(2,4,6-trimethylphenyl)imidazole

: 950595-40-1
3-(2-methylene-4-nitrophenol)-1-(2,4,6-trimethylphenyl)imidazolium bromide

Conditions

Conditions	Yield
In toluene for 18h; Reflux;	98.5%
In toluene for 18h; Reflux; Inert atmosphere;	91%

: 2290-65-5
trimethylsilyl isothiocyanate

: 772-33-8
Koshlands reagent I

: 4-nitro-2-thiocyanatomethyl-phenol

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h;	98%

: 772-33-8
Koshlands reagent I

: 2-(azidomethyl)-4-nitrophenol

Conditions

Conditions	Yield
With sodium azide In water; acetonitrile at 0 - 20℃; for 3h; Inert atmosphere;	98%
With triethylamine In acetonitrile for 3h; Heating;	64%
With sodium azide In N,N-dimethyl-formamide at 0 - 20℃; for 16h;
With sodium azide In water; acetone at 20℃; for 1h;

: 4787-76-2
1-(2-methoxyphenyl)pyrrolidine

: 772-33-8
Koshlands reagent I

: 2-(3-methoxy-4-(pyrrolidin-1-yl)benzyl)-4-nitrophenol

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In dichloromethane at 20℃; for 24h; Inert atmosphere;	96%

: 772-33-8
Koshlands reagent I

: 104856-81-7
diphenyl (prop-2-yn-1-yl)phosphine oxide

: ((1-(2-hydroxy-5-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methyl)diphenylphosphine oxide

Conditions

Conditions	Yield
With sodium azide; bromotris(triphenylphosphine)copper(I) In water; dimethyl sulfoxide at 110℃; under 760.051 Torr; for 0.183333h; Huisgen Cycloaddition; Microwave irradiation; Green chemistry; regioselective reaction;	95.2%

: 772-33-8
Koshlands reagent I

: 75-50-3
trimethylamine

: (2-hydroxy-5-nitrobenzyl)trimethylquaternary ammonium bromide

Conditions

Conditions	Yield
In acetone at 20℃; for 1h;	95%

: 772-33-8
Koshlands reagent I

: 1204-28-0
trimellitic anhydride acid chloride

: 1,3-dioxo-1,2-dihydro-2-benzofuran-5-carboxylic acid 2-bromomethyl-4-nitrophenyl ester

Conditions

Conditions	Yield
With pyridine at 0 - 20℃; for 4h;	94%

: 772-33-8
Koshlands reagent I

: 638-29-9
n-valeryl chloride

: 133238-87-6
2-(n-butyl)-5-nitrobenzofuran

Conditions

Conditions	Yield
Stage #1: Koshlands reagent I With triphenylphosphine In dichloromethane for 1h; Reflux; Stage #2: n-valeryl chloride With triethylamine In dichloromethane for 3h; Reflux;	94%

: 772-33-8
Koshlands reagent I

: 107-21-1
ethylene glycol

: 2-(2-hydroxy-5-nirtobenzyloxy)ethanol

Conditions

Conditions	Yield
at 60℃; for 5h;	93%

: 772-33-8
Koshlands reagent I

: 36080-67-8
4,13-diazadibenzo-18-crown-6

: N,N'-bis(2-hydroxy-5-nitrobenzyl)-4,13-diazadibenzo-18-crown-6

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran 1.) 0 deg C, 8 h, 2.) reflux, 4 h;	93%

: 4096-21-3
N-phenylpyrrolidine

: 772-33-8
Koshlands reagent I

: 4-nitro-2-(4-(pyrrolidin-1-yl)benzyl)phenol

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In dichloromethane at 20℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere;	93%

: 41378-30-7
1-(2-methylphenyl)pyrrolidine

: 772-33-8
Koshlands reagent I

: 2-(3-methyl-4-(pyrrolidin-1-yl)benzyl)-4-nitrophenol

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In dichloromethane at 20℃; for 24h; Inert atmosphere;	93%

: 772-33-8
Koshlands reagent I

: 95-13-6
1-indene

: 8-nitro-4b,10,10a,11-tetrahydroindeno[1,2-b]chromene

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In dichloromethane at 20℃; for 24h;	92%

: 772-33-8
Koshlands reagent I

: 62402-15-7
N-(2-pyridylmethyl)-N’-(2-hydroxyethyl)ethylenediamine

: C24H27N5O7

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 24h; Inert atmosphere;	91.4%

: 772-33-8
Koshlands reagent I

: 66943-05-3
1,4,7,10-tetraoxa-15-azacyclopentadecane

: 79566-00-0
N-(2-hydroxy-5-nitrobenzyl)-aza-15-crown-5

Conditions

Conditions	Yield
	91%

: 772-33-8
Koshlands reagent I

: C18H16N2

: (+)-N-(2-hydroxy-5-nitro-benzyl)-1,2,3,4-tetrahydro-1,1'-bisisoquinoline

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 50℃;	91%

: 772-33-8
Koshlands reagent I

: C18H16N2

: C25H21N3O3

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 50℃; Inert atmosphere;	91%

: 772-33-8
Koshlands reagent I

: 121-45-9
phosphorous acid trimethyl ester

: 84713-52-0
(2-Hydroxy-5-nitro-benzyl)-phosphonic acid dimethyl ester

Conditions

Conditions	Yield
In acetone for 0.25h;	90%
at 80 - 100℃; for 0.5h;

: 772-33-8
Koshlands reagent I

: 1-isopropoxyoctahydro-[1,3,2]diazaphospholo[1,5-a]pyridine

: 1-(2-hydroxy-5-nitrobenzyl)octahydro-[1,3,2]diazaphospholo[1,5-a]pyridine-1-oxide

Conditions

Conditions	Yield
With cerium(III) chloride heptahydrate In tetrahydrofuran at 20 - 60℃; for 3.25h; Michaelis-Arbuzov Synthesis; Inert atmosphere; Green chemistry;	90%

: 772-33-8
Koshlands reagent I

: 121-69-7
N,N-dimethyl-aniline

: 2-(4-(dimethylamino)benzyl)-4-nitrophenol

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In dichloromethane at 20℃; for 24h; Inert atmosphere;	90%

: 33941-15-0
1-aza-18-crown-6

: 772-33-8
Koshlands reagent I

: 79592-90-8
N-(2-hydroxy-5-nitrobenzyl)-aza-18-crown-6

Conditions

Conditions	Yield
	89%

: 772-33-8
Koshlands reagent I

: 17356-08-0
thiourea

: 129426-10-4
2-[(2-hydroxy-5-nitrophenyl)methyl]isothiourea

Conditions

Conditions	Yield
In ethanol at 20℃; for 2h;	89%

: 824-21-5
N-methylindoline

: 772-33-8
Koshlands reagent I

: 2-((1-methylindolin-5-yl)methyl)-4-nitrophenol

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In dichloromethane at 20℃; for 24h; Inert atmosphere;	89%

2-Hydroxy-5-nitrobenzyl bromide Specification

The Phenol,2-(bromomethyl)-4-nitro- with CAS registry number of 772-33-8 is also known as 2-Hydroxy-5-nitrobenzyl bromide. The IUPAC name is 2-(Bromomethyl)-4-nitrophenol. Its EINECS registry number is 212-248-9. In addition, the formula is C₇H₆BrNO₃ and the molecular weight is 232.03. This chemical is a beige to yellow crystalline powder that may destroy living tissue on contact. It should be sealed in cool, dry place away from oxidants.

Physical properties about Phenol,2-(bromomethyl)-4-nitro- are: (1)ACD/LogP: 2.27; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.19; (4)ACD/LogD (pH 7.4): 1.02; (5)ACD/BCF (pH 5.5): 25.75; (6)ACD/BCF (pH 7.4): 1.74; (7)ACD/KOC (pH 5.5): 336.74; (8)ACD/KOC (pH 7.4): 22.75; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.653; (13)Molar Refractivity: 47.32 cm³; (14)Molar Volume: 129.1 cm³; (15)Surface Tension: 64.9 dyne/cm; (16)Density: 1.795 g/cm³; (17)Flash Point: 185.5 °C; (18)Enthalpy of Vaporization: 65.62 kJ/mol; (19)Boiling Point: 383 °C at 760 mmHg; (20)Vapour Pressure: 2.05E-06 mmHg at 25 °C.

Uses of Phenol,2-(bromomethyl)-4-nitro-: it is used to produce 2-hydroxy-5-nitrobenzylcyanide by reaction with lithium cyanide. The reaction occurs with solvents tetrahydrofuran, dimethylformamide and other condition of heating for 3 hours. The yield is about 72%.

Phenol,2-(bromomethyl)-4-nitro- is used to produce 2-hydroxy-5-nitrobenzylcyanide by reaction with lithium cyanide.

When you are using this chemical, please be cautious about it. As a chemical, it causes burns. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])CBr)O
2. InChI: InChI=1S/C7H6BrNO3/c8-4-5-3-6(9(11)12)1-2-7(5)10/h1-3,10H,4H2
3. InChIKey: KFDPCYZHENQOBV-UHFFFAOYSA-N

Product Name

2-HYDROXY-5-NITROBENZYL BROMIDE

Synthetic route

2-Hydroxy-5-nitrobenzyl bromide Specification

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