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52-51-7

Basic Information
CAS No.: 52-51-7
Name: 1,3-Propanediol,2-bromo-2-nitro-
Molecular Structure:
Molecular Structure of 52-51-7 (1,3-Propanediol,2-bromo-2-nitro-)
Formula: C3 H6BrNO4
Molecular Weight: 199.98
Synonyms: 2-Bromo-2-nitro-1,3-propanediol;2-Bromo-2-nitropropan-1,3-diol;2-Bromo-2-nitropropane-1,3-diol;2-Nitro-2-bromo-1,3-propanediol;Bioban;Bronidiol;Bronocot;Bronopol;Bronotak;Canguard 409;Myacide AS;Myacide AS Plus;Myacide PharmaBP;N 25 (antimicrobial);NSC 141021;Nalco 92RU093;Preventol P 100;Protectol BN 98;Protectol BN 99;Ultra-Fresh SAB;
EINECS: 200-143-0
Density: 2.018 g/cm3
Melting Point: 130- 133°C
Boiling Point: 358 °C at 760 mmHg
Flash Point: 170.3 °C
Solubility: 25 g/100 mL (22 °C) in water
Appearance: off-white crystalline powder
Hazard Symbols: HarmfulXn, DangerousN
Risk Codes: 21/22-37/38-41-50
Safety: 26-37/39-61
Transport Information: UN 3241 4.1/PG 3
PSA: 86.28000
LogP: -0.13790
Synthetic route

Sodium; 3-hydroxy-2-[(Z)-hydroxyimino]-propionate

52-51-7

2-bromo-2-nitro-1,3-propanediol

Conditions
ConditionsYield
With bromine In diethyl ether at 0℃; for 0.5h;88.6%
50-00-0

formaldehyd

75-52-5

nitromethane

464-10-8

bromopicrin

52-51-7

2-bromo-2-nitro-1,3-propanediol

Conditions
ConditionsYield
With sodium hydroxide In water at 44 - 55℃; pH=5.3 - 7.2; Product distribution / selectivity;76.8%
50-00-0

formaldehyd

563-70-2

bromonitromethane

52-51-7

2-bromo-2-nitro-1,3-propanediol

126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

52-51-7

2-bromo-2-nitro-1,3-propanediol

Conditions
ConditionsYield
With alkali hypobromite und nachfolgender Zusatz von Brom;
126-11-4

2-hydroxymethyl-2-nitro-propane-1,3-diol

bromo solution

bromo solution

bromine

bromine

A

52-51-7

2-bromo-2-nitro-1,3-propanediol

B

464-10-8

bromopicrin

C

potassium salt of bromodinitromethane

potassium salt of bromodinitromethane

50-00-0

formaldehyd

(+-)-1--cyclohexanol

(+-)-1--cyclohexanol

52-51-7

2-bromo-2-nitro-1,3-propanediol

Conditions
ConditionsYield
With sodium hydroxide
sodium compound of β-nitro-trimethylene glycol

sodium compound of β-nitro-trimethylene glycol

52-51-7

2-bromo-2-nitro-1,3-propanediol

Conditions
ConditionsYield
With chloroform; bromine
sodium compound of 2-nitro-propanediol-(1.3)

sodium compound of 2-nitro-propanediol-(1.3)

52-51-7

2-bromo-2-nitro-1,3-propanediol

Conditions
ConditionsYield
With bromine

5-bromo-2-(2-methylpropyl)-5-nitro-1,3,2-dioxaborinane

52-51-7

2-bromo-2-nitro-1,3-propanediol

Conditions
ConditionsYield
With water; oxygen
52-51-7

2-bromo-2-nitro-1,3-propanediol

A

150-60-7

dibenzyl disulphide

B

1092975-49-9

2,3-bis(hydroxymethyl)-2-,3-dinitro-1,4-butanediol

Conditions
ConditionsYield
With sodium; phenylmethanethiol In methanol for 1h;A 99%
B 48%
52-51-7

2-bromo-2-nitro-1,3-propanediol

75-07-0

acetaldehyde

53983-00-9

5-bromo-2-methyl-5-nitro-1,3-dioxane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In water; benzene85%
52-51-7

2-bromo-2-nitro-1,3-propanediol

77-76-9

2,2-dimethoxy-propane

60766-57-6

2,2-dimethyl-5-bromo-5-nitro-1,3-dioxane

Conditions
ConditionsYield
With [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid at 20℃; for 48h;82%
With camphor-10-sulfonic acid at 20℃; for 72h; Inert atmosphere;75.3%
50-00-0

formaldehyd

52-51-7

2-bromo-2-nitro-1,3-propanediol

75-64-9

tert-butylamine

261508-04-7

1,3-di(tert-butyl)-5-bromo-5-nitro-1,3-diazacyclohexane

Conditions
ConditionsYield
In methanol; water at 20℃; for 48h; Condensation; cyclization;81%
52-51-7

2-bromo-2-nitro-1,3-propanediol

67-64-1

acetone

60766-57-6

2,2-dimethyl-5-bromo-5-nitro-1,3-dioxane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 120℃; for 24h;73%
With chloroform; sulfuric acid
50-00-0

formaldehyd

52-51-7

2-bromo-2-nitro-1,3-propanediol

30007-47-7

bronidox

Conditions
ConditionsYield
With sulfuric acid; hydrogen bromide In water at 95℃; for 1h;69%

(5-O-nitro-1,4:3,6-dianhydro-D-sorbit-2-yl) phosphorodichloridate

52-51-7

2-bromo-2-nitro-1,3-propanediol

1225453-43-9

5-bromo-2-(5-O-nitro-1,4:3,6-dianhydro-D-glucit-2-yloxy)-5-nitro-2-oxo-1,3,2λ5-dioxaphosphorinane

Conditions
ConditionsYield
With pyridine In acetonitrile at 15 - 30℃; for 23.5h;68%
52-51-7

2-bromo-2-nitro-1,3-propanediol

95093-83-7

diisobutyl ester of isobutylboronic acid

5-bromo-2-(2-methylpropyl)-5-nitro-1,3,2-dioxaborinane

Conditions
ConditionsYield
In benzene68%
52-51-7

2-bromo-2-nitro-1,3-propanediol

122-52-1

triethyl phosphite

C7H16NO7P

Conditions
ConditionsYield
In toluene Michaelis-Arbuzov Synthesis; Reflux;67%
52-51-7

2-bromo-2-nitro-1,3-propanediol

86623-97-4

4-bromophenyl carbamidophosphoric acid dichloride

N-bromophenyl-N'-[5-bromo-5-nitro-2-oxido-1,3,2-dioxaphosphorinane-2-yl]urea

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; toluene at 0 - 20℃; for 7h;62%
52-51-7

2-bromo-2-nitro-1,3-propanediol

101252-13-5

N-4-methylphenylureidophosphoryl dichloride

1-(5-bromo-5-nitro-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-3-p-tolyl-urea

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; toluene at 0 - 20℃;61%
676-97-1

methylphosphonic acid dichloroanhydride

52-51-7

2-bromo-2-nitro-1,3-propanediol

5-bromo-nitro-2-methyl-2-oxo-1,3,2-dioxaphosphorinane

Conditions
ConditionsYield
In 1,4-dioxane at 50℃; for 3h; Product distribution; reactions of derivatives;60%
In 1,4-dioxane at 50℃; for 3h;60%
777-52-6

1-dichlorophosphoryloxy-4-nitro-benzene

52-51-7

2-bromo-2-nitro-1,3-propanediol

75386-09-3

5-bromo-5-nitro-2-p-nitrophenoxy-2oxo-1,3,2-dioxaphosphorinane

Conditions
ConditionsYield
In 1,4-dioxane at 50℃; for 3h;60%
52-51-7

2-bromo-2-nitro-1,3-propanediol

4797-12-0

4-chlorophenyl-carbamidophosphoric acid dichloride

1-(5-bromo-5-nitro-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-3-(4-chloro-phenyl)-urea

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; toluene at 0 - 20℃;60%
52-51-7

2-bromo-2-nitro-1,3-propanediol

41018-19-3

2,4-dimethylphenyl carbamidophosphoric acid dichloride

1-(5-bromo-5-nitro-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-3-(2,4-dimethyl-phenyl)-urea

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; toluene at 0 - 20℃;58%
52-51-7

2-bromo-2-nitro-1,3-propanediol

770-12-7

O-phenyl phosphorodichloridate

75386-07-1

5-bromo-5-nitro-2-phenoxy-2-oxo-1,3,2-dioxaphosphorinane

Conditions
ConditionsYield
In 1,4-dioxane at 50℃; for 3h;56%
52-51-7

2-bromo-2-nitro-1,3-propanediol

603964-78-9

C8H8Cl3N2O2P

1-(5-bromo-5-nitro-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-3-(2-chloromethyl-phenyl)-urea

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; toluene at 0 - 20℃;56%
52-51-7

2-bromo-2-nitro-1,3-propanediol

4797-20-0

[1]naphthylcarbamoyl-amidophosphoryl chloride

1-(5-bromo-5-nitro-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-3-naphthalen-1-yl-urea

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; toluene at 0 - 20℃;53%
52-51-7

2-bromo-2-nitro-1,3-propanediol

4797-10-8

phenylcarbamidophosphoric acid dichloride

1-(5-bromo-5-nitro-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-3-phenyl-urea

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; toluene at 0 - 20℃;52%
52-51-7

2-bromo-2-nitro-1,3-propanediol

878-17-1

4-methylphenyl phosphorodichloridate

75386-08-2

5-Bromo-5-nitro-2-p-tolyloxy-[1,3,2]dioxaphosphinane 2-oxide

Conditions
ConditionsYield
In 1,4-dioxane at 50℃; for 3h;49%
52-51-7

2-bromo-2-nitro-1,3-propanediol

603964-77-8

C7H13Cl2N2O2P

1-(5-bromo-5-nitro-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-3-cyclohexyl-urea

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; toluene at 0 - 20℃;48%
52-51-7

2-bromo-2-nitro-1,3-propanediol

940-18-1

m-Tolyl dichlorophosphate

75401-02-4

5-Bromo-5-nitro-2-m-tolyloxy-[1,3,2]dioxaphosphinane 2-oxide

Conditions
ConditionsYield
In 1,4-dioxane at 50℃; for 3h;42%
127-88-8

N,N-di(2-chloroethyl)amidophosphoric acid dichloride

52-51-7

2-bromo-2-nitro-1,3-propanediol

5-bromo-5-nitro-2-bis(2-chloroethyl)amino-1,3,2-dioxaphosphorinane 2-oxide

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃; for 4h;42%
13417-49-7

5,6-dihydro-2H-pyran-3-carbaldehyde

52-51-7

2-bromo-2-nitro-1,3-propanediol

133609-60-6

5-Brom-5-nitro-2-(5',6'-dihydro-2'H-pyranyl)-1,3-dioxan

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Heating;40.3%
52-51-7

2-bromo-2-nitro-1,3-propanediol

60766-57-6

2,2-dimethyl-5-bromo-5-nitro-1,3-dioxane

Conditions
ConditionsYield
With trifluoroborane diethyl ether; sodium hydrogencarbonate In hexane; acetone40%
52-51-7

2-bromo-2-nitro-1,3-propanediol

3576-20-3

2,2,2-trichloro-1,3-dimethyl-1,3,2-diazaphosphetidin-4-one

2-chlor-1,3-dimethyl-7-brom-7-nitro-1,3-diaza-5,9-dioxa-5λ5-phosphaspiro<3.5>nonan-4-on

Conditions
ConditionsYield
In dichloromethane for 4h;38%
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Chemistry

Molecular Structure of Bronopol (CAS NO.52-51-7): 

IUPAC Name: 2-bromo-2-nitropropane-1,3-diol 
Empirical Formula: C3H6BrNO4 
Molecular Weight: 199.988 
Index of Refraction:  1.574 
Surface Tension:  74.1 dyne/cm 
Density:  2.018 g/cm3 
Flash Point: 170.3 °C 
Enthalpy of Vaporization:  69.86 kJ/mol 
Boiling Point: 358 °C at 760 mmHg 
Vapour Pressure: 1.45E-06 mmHg at 25°C 
Synonyms:1,3-Propanediol, 2-bromo-2-nitro- ; 2-Bromo-1-nitro-1,3-propanediol ; 2-bromo-2-nitro-3-propanediol ; 2-Bromo-2-nitropropan-1,3-diol ; 2-Nitro-2-bromo-1,3-propanediol ; 3-Propanediol,2-bromo-2-nitro-1 ; beta-Bromo-beta-nitrotrimethyleneglycol

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 250mg/kg (250mg/kg)   "Pesticide Index," Frear, E.H., ed., State College, PA, College Science Pub., 1969Vol. 5, Pg. 30, 1976.
mouse LD50 intraperitoneal 15500ug/kg (15.5mg/kg)   Khimiko-Farmatsevticheskii Zhurnal. Chemical Pharmaceutical Journal. For English translation, see PCJOAU. Vol. 11(1), Pg. 73, 1977.
mouse LD50 intravenous 48mg/kg (48mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 680, 1977.
mouse LD50 oral 270mg/kg (270mg/kg)   Pesticide Manual. Vol. 9, Pg. 103, 1991.
mouse LD50 skin 4750mg/kg (4750mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 680, 1977.
mouse LD50 subcutaneous 116mg/kg (116mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 680, 1977.
rat LC50 inhalation > 5gm/m3/6H (5000mg/m3)   Pesticide Manual. Vol. 9, Pg. 103, 1991.
rat LD50 intraperitoneal 26mg/kg (26mg/kg)   Journal of the Society of Cosmetic Chemists. Vol. 29, Pg. 3, 1978.
rat LD50 intravenous 37400ug/kg (37.4mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 680, 1977.
rat LD50 oral 180mg/kg (180mg/kg)   "Pesticide Index," Frear, E.H., ed., State College, PA, College Science Pub., 1969Vol. 5, Pg. 30, 1976.
rat LD50 skin 1600mg/kg (1600mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A542, Pg. 1984,
rat LD50 subcutaneous 170mg/kg (170mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Kiso to Rinsho. Clinical Report. Vol. 8, Pg. 1029, 1974.

Safety Profile

Hazard Codes HarmfulXn,DangerousN
Risk Statements 21/22-37/38-41-50 
R21/22:Harmful in contact with skin and if swallowed. 
R37/38:Irritating to respiratory system and skin. 
R41:Risk of serious damage to the eyes. 
R50:Very toxic to aquatic organisms.
Safety Statements 26-37/39-61 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39:Wear suitable gloves and eye/face protection. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.

Specification

 Bronopol (CAS NO.52-51-7) is a white crystals,would burn easily,it may detonate under strong shock.While heated to decomposion evolving toxic gases. Toxic substances through skin absorption, inhalation or ingestion.

 Bronopol (CAS NO.52-51-7) is a killing bacterial agents,it can effectively control a variety of plant pathogenic bacteria.It is mainly used for cosmetics,leather preservation,widely used in water treatment, pharmaceutical, pesticides, cosmetics, detergent and other industries as preservatives and sterilizing agents, by the nitro-methane and formaldehyde , bromine reaction derived.Invested in the reactor measured nitro-methane, formaldehyde, water and ethanol, 40% liquid caustic soda was added dropwise under cooling at this time there is solid precipitation, and then dropping quantitative bromine, plus completion of mixing, vacuum steam out of part of the water and ethanol, after cooling, crystallization, filtration, drying advanced Bronopol, the yield of above 70%, content is about 93%.

 Bronopol (CAS NO.52-51-7) is a highly-toxic pesticide,burning will produce bromide and nitrogen oxides emitted toxic fumes.Besides should be stored and transported in low-temperature,drying environment. separately with oxidizing agents.Fire extinguishing agents water, carbon dioxide, dry powder, foam would be used if emergency.

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